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PRICE IMPROVEMENT! Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

3 Beds ⋅ 2 Baths

PRICE IMPROVEMENT! Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

1048 Woodland Ave, Winchester

Listing courtesy of Re/Max Roots. Contact:

$699,000

HUGE BUYER INCENTIVES — $10,000 TOWARD CLOSING COSTS PLUS SELLER-PAID 1-POINT PERMANENT MORTGAGE RATE BUYDOWN! OFFERED AT $699,000 | 5 BEDROOMS | 3.5 BATHROOMS | 3,946 FINISHED SQ. FT. | 2-CAR GARAGE | BUILT IN 2019 Welcome to 110 Bentpath Court, a spacious Richmond American Colonial in the desirable Twin Lakes Overlook community of Winchester, Virginia. Offering nearly 4,000 square feet of finished living space across three levels, this beautiful home combines modern comfort, flexible living arrangements, and exceptional value in an established neighborhood of single-family homes. SPACIOUS MAIN LEVEL — DESIGNED FOR COMFORT AND ENTERTAINING The main level features generous living and entertaining spaces, a large modern kitchen with stainless steel appliances, contemporary finishes, and an inviting layout ideal for everyday living, working from home, and hosting family and friends. FIVE BEDROOMS ON THE UPPER LEVEL The upper level includes five bedrooms, including a spacious primary suite, offering plenty of room for family members, guests, and dedicated home-office space. APPROXIMATELY 1,000-SQ.-FT. FINISHED WALK-OUT LOWER LEVEL — IDEAL FOR MULTIGENERATIONAL LIVING A standout feature of this home is its expansive finished lower level, offering approximately 1,000 square feet of additional living space included in the home's total finished square footage. This versatile area includes a potential sixth bedroom (NTC), a full bathroom, a second kitchen/kitchenette, 2nd washer/dryer hook-up and a separate rear walk-out entrance. The flexible layout is ideal for extended-family living, overnight guests, recreation, a home office, or a private retreat—all while remaining part of the main residence. PRIVATE, TREE-LINED BACKYARD AND TWO-CAR GARAGE Situated on approximately 0.20 acre, the property features an attractive siding-and-stone exterior, an attached two-car garage, driveway parking, and a beautiful tree-lined backyard. Enjoy outdoor entertaining, gardening, or simply relaxing in a peaceful residential setting. DESIRABLE TWIN LAKES OVERLOOK LOCATION — CONVENIENT TO WINCHESTER AND NORTHERN VIRGINIA Enjoy the charm and tranquility of an established single-family-home neighborhood with convenient access to: Route 7 and Interstate 81 for regional commuting Winchester Medical Center and nearby healthcare services Historic Old Town Winchester, with restaurants, boutiques, shopping, and entertainment Jim Barnett Park and local recreational facilities Nearby lakes, parks, and the scenic Shenandoah Valley Shopping, groceries, schools, and everyday conveniences EXCEPTIONAL VALUE AT $699,000 — PLUS VALUABLE SELLER FINANCING INCENTIVES INCLUDING $10,000 TOWARD BUYER CLOSING COSTS PLUS UP TO ONE SELLER-PAID PERMANENT MORTGAGE DISCOUNT POINT TO HELP LOWER THE BUYER'S INTEREST RATE!

5 Beds ⋅ 4 Baths

HUGE BUYER INCENTIVES — $10,000 TOWARD CLOSING COSTS PLUS SELLER-PAID 1-POINT PERMANENT MORTGAGE RATE BUYDOWN! OFFERED AT $699,000 | 5 BEDROOMS | 3.5 BATHROOMS | 3,946 FINISHED SQ. FT. | 2-CAR GARAGE | BUILT IN 2019 Welcome to 110 Bentpath Court, a spacious Richmond American Colonial in the desirable Twin Lakes Overlook community of Winchester, Virginia. Offering nearly 4,000 square feet of finished living space across three levels, this beautiful home combines modern comfort, flexible living arrangements, and exceptional value in an established neighborhood of single-family homes. SPACIOUS MAIN LEVEL — DESIGNED FOR COMFORT AND ENTERTAINING The main level features generous living and entertaining spaces, a large modern kitchen with stainless steel appliances, contemporary finishes, and an inviting layout ideal for everyday living, working from home, and hosting family and friends. FIVE BEDROOMS ON THE UPPER LEVEL The upper level includes five bedrooms, including a spacious primary suite, offering plenty of room for family members, guests, and dedicated home-office space. APPROXIMATELY 1,000-SQ.-FT. FINISHED WALK-OUT LOWER LEVEL — IDEAL FOR MULTIGENERATIONAL LIVING A standout feature of this home is its expansive finished lower level, offering approximately 1,000 square feet of additional living space included in the home's total finished square footage. This versatile area includes a potential sixth bedroom (NTC), a full bathroom, a second kitchen/kitchenette, 2nd washer/dryer hook-up and a separate rear walk-out entrance. The flexible layout is ideal for extended-family living, overnight guests, recreation, a home office, or a private retreat—all while remaining part of the main residence. PRIVATE, TREE-LINED BACKYARD AND TWO-CAR GARAGE Situated on approximately 0.20 acre, the property features an attractive siding-and-stone exterior, an attached two-car garage, driveway parking, and a beautiful tree-lined backyard. Enjoy outdoor entertaining, gardening, or simply relaxing in a peaceful residential setting. DESIRABLE TWIN LAKES OVERLOOK LOCATION — CONVENIENT TO WINCHESTER AND NORTHERN VIRGINIA Enjoy the charm and tranquility of an established single-family-home neighborhood with convenient access to: Route 7 and Interstate 81 for regional commuting Winchester Medical Center and nearby healthcare services Historic Old Town Winchester, with restaurants, boutiques, shopping, and entertainment Jim Barnett Park and local recreational facilities Nearby lakes, parks, and the scenic Shenandoah Valley Shopping, groceries, schools, and everyday conveniences EXCEPTIONAL VALUE AT $699,000 — PLUS VALUABLE SELLER FINANCING INCENTIVES INCLUDING $10,000 TOWARD BUYER CLOSING COSTS PLUS UP TO ONE SELLER-PAID PERMANENT MORTGAGE DISCOUNT POINT TO HELP LOWER THE BUYER'S INTEREST RATE!

110 Bentpath Ct, Winchester

Listing courtesy of Realty Aspire. Contact:

$539,900

Fully Renovated Winchester-Area Retreat on 3.24 Acres with Two Garages! Rarely does a property come along that offers this combination of extensive renovations, usable acreage, incredible storage, multiple garages, and a peaceful established neighborhood, all just minutes from everything Winchester has to offer. Welcome to 127 Mountain View Rd, where quiet living meets modern convenience, and nearly everything has been thoughtfully updated for today's buyer. Inside, extensive updates include fresh paint, new LVP flooring, refinished hardwood floors, updated fixtures and lighting, and 2-inch recessed lighting. The luxury kitchen features a large 5-foot island, quartz countertops, stainless-steel appliances, and under-cabinet lighting, plus a convenient pop-up electrical outlet/device charger in the island. Major improvements provide exceptional peace of mind, including a new roof (2025), new Rheem HVAC system (2026), new baseboard heat (2026), new water heater (2026), and completely new septic system with tank, distribution box, and lines (2026). Newer windows add to the home's efficiency and appeal. Enjoy outdoor living on the freshly stained 48' x 12' deck, perfect for entertaining, grilling, or relaxing. The oversized attached garage offers abundant storage and features a new garage door and opener. A second 26' x 17' detached garage with its own basement provides exceptional workshop, hobby, equipment, and storage space. With the right vision, the detached structure offers a variety of opportunities. Fresh landscaping and a newly graded oversized driveway provide plenty of parking and a welcoming approach. Located just minutes from downtown Winchester, shopping, restaurants, the hospital, gyms, and schools. Enjoy a quiet neighborhood setting with an established community feel while remaining close to everything you need. Homes in this great neighborhood are a rarity, don't miss your opportunity to see this one. 3.24 acres | Extensive 2025–2026 updates | Luxury kitchen | Two garages | Workshop potential | New septic | New HVAC | New roof | Large deck | No HOA | Minutes to Winchester.

4 Beds ⋅ 3 Baths

Fully Renovated Winchester-Area Retreat on 3.24 Acres with Two Garages! Rarely does a property come along that offers this combination of extensive renovations, usable acreage, incredible storage, multiple garages, and a peaceful established neighborhood, all just minutes from everything Winchester has to offer. Welcome to 127 Mountain View Rd, where quiet living meets modern convenience, and nearly everything has been thoughtfully updated for today's buyer. Inside, extensive updates include fresh paint, new LVP flooring, refinished hardwood floors, updated fixtures and lighting, and 2-inch recessed lighting. The luxury kitchen features a large 5-foot island, quartz countertops, stainless-steel appliances, and under-cabinet lighting, plus a convenient pop-up electrical outlet/device charger in the island. Major improvements provide exceptional peace of mind, including a new roof (2025), new Rheem HVAC system (2026), new baseboard heat (2026), new water heater (2026), and completely new septic system with tank, distribution box, and lines (2026). Newer windows add to the home's efficiency and appeal. Enjoy outdoor living on the freshly stained 48' x 12' deck, perfect for entertaining, grilling, or relaxing. The oversized attached garage offers abundant storage and features a new garage door and opener. A second 26' x 17' detached garage with its own basement provides exceptional workshop, hobby, equipment, and storage space. With the right vision, the detached structure offers a variety of opportunities. Fresh landscaping and a newly graded oversized driveway provide plenty of parking and a welcoming approach. Located just minutes from downtown Winchester, shopping, restaurants, the hospital, gyms, and schools. Enjoy a quiet neighborhood setting with an established community feel while remaining close to everything you need. Homes in this great neighborhood are a rarity, don't miss your opportunity to see this one. 3.24 acres | Extensive 2025–2026 updates | Luxury kitchen | Two garages | Workshop potential | New septic | New HVAC | New roof | Large deck | No HOA | Minutes to Winchester.

127 Mountain View Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$159,900

Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natural beauty. Step outside onto the screened-in porch and enjoy your morning coffee, unwind with a good book, or simply take in the sights and sounds of the surrounding woods. This peaceful setting offers a wonderful opportunity to slow down and enjoy nature while still having all the comfort you need. Whether you're searching for a weekend getaway, a cozy full-time residence, or an investment property with rental potential, this versatile cottage is full of possibilities. Newer upgrades include an electrical panel, UV light, and exterior and interior painting/siding. Won’t last long at this price point!

1 Beds ⋅ 1 Baths

Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natural beauty. Step outside onto the screened-in porch and enjoy your morning coffee, unwind with a good book, or simply take in the sights and sounds of the surrounding woods. This peaceful setting offers a wonderful opportunity to slow down and enjoy nature while still having all the comfort you need. Whether you're searching for a weekend getaway, a cozy full-time residence, or an investment property with rental potential, this versatile cottage is full of possibilities. Newer upgrades include an electrical panel, UV light, and exterior and interior painting/siding. Won’t last long at this price point!

305 Raccoon Dr, Winchester

Listing courtesy of Dandridge Realty Group, LLC. Contact:

$959,900

****MORE AFFORDABILITY! SELLER IS PAYING FOR A RATE BUY DOWN OR CLOSING COST ASSISTANCE ***** Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking mountainous backdrop. Built in 2019, this home boasts an impressive 3,317 square feet of meticulously designed living space, perfect for those who appreciate both elegance and functionality. The kitchen is a culinary dream, featuring high-end appliances including a built-in microwave, electric cooktop, and self-cleaning wall oven, all complemented by ample table space and a cozy eat-in area. Beautiful built-ins and walk-in closets provide both style and practicality, ensuring that every inch of this home is utilized to its fullest potential. The main level also features a thoughtfully designed entry-level bedroom and a luxurious bathroom with a walk-in shower, catering to convenience and comfort. Ascend to the upper levels to find two additional spacious bedrooms with its own spacious full bathroom, promising tranquility and relaxation. The fully finished basement offers endless possibilities, a forth bedroom or office with a full bathroom, daylight windows and walkout access to the serene outdoors, making it perfect for a home gym, media room, or additional living space. There is also an expansive storage area for all your needs. Outside, the property spans over 5 acres of beautifully cleared and landscaped grounds, providing a private oasis that backs to lush trees. Enjoy the tranquility of nature from your beautiful wrap-around porch, where you can unwind and soak in the stunning mountain views. The lower level offers a concrete area with a hot tub. There is a beautiful large detached 3 car garage for all of your cars, motorcycles or mowers. This home is not just a residence; it's a lifestyle. Experience the luxury of modern living in a serene mountain setting, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. With its exceptional features and prime location, this property is a rare gem that promises to be a cherished sanctuary for years to come. Generator hook up wired for electric outages and Outside water bib running hot and cold water for dog baths and other use. Also antenna and modens stay in the house ($500) Value. Come see it today!

4 Beds ⋅ 4 Baths

****MORE AFFORDABILITY! SELLER IS PAYING FOR A RATE BUY DOWN OR CLOSING COST ASSISTANCE ***** Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking mountainous backdrop. Built in 2019, this home boasts an impressive 3,317 square feet of meticulously designed living space, perfect for those who appreciate both elegance and functionality. The kitchen is a culinary dream, featuring high-end appliances including a built-in microwave, electric cooktop, and self-cleaning wall oven, all complemented by ample table space and a cozy eat-in area. Beautiful built-ins and walk-in closets provide both style and practicality, ensuring that every inch of this home is utilized to its fullest potential. The main level also features a thoughtfully designed entry-level bedroom and a luxurious bathroom with a walk-in shower, catering to convenience and comfort. Ascend to the upper levels to find two additional spacious bedrooms with its own spacious full bathroom, promising tranquility and relaxation. The fully finished basement offers endless possibilities, a forth bedroom or office with a full bathroom, daylight windows and walkout access to the serene outdoors, making it perfect for a home gym, media room, or additional living space. There is also an expansive storage area for all your needs. Outside, the property spans over 5 acres of beautifully cleared and landscaped grounds, providing a private oasis that backs to lush trees. Enjoy the tranquility of nature from your beautiful wrap-around porch, where you can unwind and soak in the stunning mountain views. The lower level offers a concrete area with a hot tub. There is a beautiful large detached 3 car garage for all of your cars, motorcycles or mowers. This home is not just a residence; it's a lifestyle. Experience the luxury of modern living in a serene mountain setting, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. With its exceptional features and prime location, this property is a rare gem that promises to be a cherished sanctuary for years to come. Generator hook up wired for electric outages and Outside water bib running hot and cold water for dog baths and other use. Also antenna and modens stay in the house ($500) Value. Come see it today!

236 Delmas Trl, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$295,000

A Little Vision. A Lot of Potential. Nearly an Acre to Make It Happen! Tucked away in the wooded surroundings of Shawneeland, this spacious property offers a rare opportunity to create something truly special. Whether you envision a peaceful mountain retreat, a full-time residence, or an investment property, the possibilities are yours to explore! Situated on a generous corner lot of nearly one acre, originally two separate parcels combined into one, this property offers exceptional space, privacy, and flexibility. With approximately 2,000+ square feet of finished living space and the potential for over 2,400 total square feet, there's plenty of room to bring your vision to life. Several major improvements have already been completed, including foundation repairs, roof, porch, HVAC, and well pump/bladder (2012), along with a hot water heater (2019). The expansive porch was framed with a future hot tub in mind, creating an exciting opportunity for an outdoor retreat. A walk-out basement and oversized attached two-car garage provide additional versatility for a workshop, hobbies, storage, or future improvements. Enjoy the serenity of a wooded setting while remaining approximately 15 miles from the shops, restaurants, and historic charm of downtown Winchester. Looking for a renovation project with potential? This could be the opportunity you've been waiting for! Bring your contractor, creativity, and imagination to transform this property into something extraordinary. NO HOA! Property may qualify for FHA 203(k) renovation financing, offering eligible buyers the opportunity to finance both the purchase and qualifying improvements. Contact the listing agent for additional details. Property is being sold strictly AS IS. An opportunity to create value and make this home uniquely yours!

2 Beds ⋅ 3 Baths

A Little Vision. A Lot of Potential. Nearly an Acre to Make It Happen! Tucked away in the wooded surroundings of Shawneeland, this spacious property offers a rare opportunity to create something truly special. Whether you envision a peaceful mountain retreat, a full-time residence, or an investment property, the possibilities are yours to explore! Situated on a generous corner lot of nearly one acre, originally two separate parcels combined into one, this property offers exceptional space, privacy, and flexibility. With approximately 2,000+ square feet of finished living space and the potential for over 2,400 total square feet, there's plenty of room to bring your vision to life. Several major improvements have already been completed, including foundation repairs, roof, porch, HVAC, and well pump/bladder (2012), along with a hot water heater (2019). The expansive porch was framed with a future hot tub in mind, creating an exciting opportunity for an outdoor retreat. A walk-out basement and oversized attached two-car garage provide additional versatility for a workshop, hobbies, storage, or future improvements. Enjoy the serenity of a wooded setting while remaining approximately 15 miles from the shops, restaurants, and historic charm of downtown Winchester. Looking for a renovation project with potential? This could be the opportunity you've been waiting for! Bring your contractor, creativity, and imagination to transform this property into something extraordinary. NO HOA! Property may qualify for FHA 203(k) renovation financing, offering eligible buyers the opportunity to finance both the purchase and qualifying improvements. Contact the listing agent for additional details. Property is being sold strictly AS IS. An opportunity to create value and make this home uniquely yours!

159 Aspen Trl Trl, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

$280,000

Located in the desirable Shawneeland community, this freshly updated three bedroom home is situated on a great corner lot with scenic views and plenty of possibilities to make it your own. The home features an updated kitchen, breakfast area, along with a detached two story garage/shed offering additional parking and storage. Step outside and enjoy relaxing evenings on the deck while taking in peaceful surroundings. Shawneeland offers an array of community amenities, including fishing, private access, playgrounds, and a four-hole golf course. With it's spacious lot, thoughtful updates, versatile outdoor space, and inviting setting, this quaint home is ready for it's next owner to make it their very own.

3 Beds ⋅ 1 Baths

Located in the desirable Shawneeland community, this freshly updated three bedroom home is situated on a great corner lot with scenic views and plenty of possibilities to make it your own. The home features an updated kitchen, breakfast area, along with a detached two story garage/shed offering additional parking and storage. Step outside and enjoy relaxing evenings on the deck while taking in peaceful surroundings. Shawneeland offers an array of community amenities, including fishing, private access, playgrounds, and a four-hole golf course. With it's spacious lot, thoughtful updates, versatile outdoor space, and inviting setting, this quaint home is ready for it's next owner to make it their very own.

700 Tomahawk Trl, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$300,600

Nestled in the charming Wilde Acres community, this delightful Colonial home offers a perfect blend of comfort and style. Built in 2009, this residence features 3 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and daily living. The inviting layout encompasses 1,680 sq. ft. of thoughtfully designed living space, ideal for both entertaining and quiet evenings at home. Enjoy the serene outdoor setting on a generous 0.65-acre lot, perfect for gardening or outdoor activities. The detached garage and driveway provide convenient parking options. Inside, the home boasts a warm ambiance, ready for your personal touch. Experience the tranquility of Wilde Acres while being just a short drive from local amenities. This home is not just a place to live; it's a place to thrive. Don't miss the opportunity to make it yours!

3 Beds ⋅ 3 Baths

Nestled in the charming Wilde Acres community, this delightful Colonial home offers a perfect blend of comfort and style. Built in 2009, this residence features 3 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and daily living. The inviting layout encompasses 1,680 sq. ft. of thoughtfully designed living space, ideal for both entertaining and quiet evenings at home. Enjoy the serene outdoor setting on a generous 0.65-acre lot, perfect for gardening or outdoor activities. The detached garage and driveway provide convenient parking options. Inside, the home boasts a warm ambiance, ready for your personal touch. Experience the tranquility of Wilde Acres while being just a short drive from local amenities. This home is not just a place to live; it's a place to thrive. Don't miss the opportunity to make it yours!

308 Fawn Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$659,900

Discover the possibilities at 531 Cedar Grove Road! Situated on 9.79 acres just minutes from Winchester, this distinctive property combines the charm and character of a historic farmhouse with the space and versatility of a working farm. The home offers a welcoming country atmosphere, traditional farmhouse appeal, and an opportunity to enjoy peaceful rural living while remaining convenient to town. Outside, you'll find an approximately 2,400-square-foot barn with three stalls, an established farm market building, workshop, greenhouse/storage space, orchard, garden area, and several additional outbuildings. The farm market features separate electric service, counters, shelving, and refrigeration, providing an excellent starting point for a variety of agricultural pursuits. Whether you're looking to establish a working farm, create your own homestead, or simply enjoy the beauty and freedom of nearly 10 acres, this property offers an incredible opportunity to make it your own. Buyer to verify intended uses with Frederick County. Highlights Approximately 9.79 acres Historic farmhouse 2,400± sq ft barn with 3 stalls Separate farm market building Orchard & garden area Multiple outbuildings Workshop Greenhouse/storage Convenient Winchester location

2 Beds ⋅ 1 Baths

Discover the possibilities at 531 Cedar Grove Road! Situated on 9.79 acres just minutes from Winchester, this distinctive property combines the charm and character of a historic farmhouse with the space and versatility of a working farm. The home offers a welcoming country atmosphere, traditional farmhouse appeal, and an opportunity to enjoy peaceful rural living while remaining convenient to town. Outside, you'll find an approximately 2,400-square-foot barn with three stalls, an established farm market building, workshop, greenhouse/storage space, orchard, garden area, and several additional outbuildings. The farm market features separate electric service, counters, shelving, and refrigeration, providing an excellent starting point for a variety of agricultural pursuits. Whether you're looking to establish a working farm, create your own homestead, or simply enjoy the beauty and freedom of nearly 10 acres, this property offers an incredible opportunity to make it your own. Buyer to verify intended uses with Frederick County. Highlights Approximately 9.79 acres Historic farmhouse 2,400± sq ft barn with 3 stalls Separate farm market building Orchard & garden area Multiple outbuildings Workshop Greenhouse/storage Convenient Winchester location

531 Cedar Grove Rd, Winchester

Listing courtesy of Virginia Real Estate. Contact:

$299,900

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey!

2 Beds ⋅ 2 Baths

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey!

2519 Hockman Ave, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

$645,000

Come and discover this impressive beauty where easy main-level living meets exceptional indoor-outdoor entertaining. This beautifully appointed Cape Cod offers the convenience of a spacious main-level primary suite, while the heart of the home flows seamlessly from the well-appointed kitchen to a covered rear porch overlooking the sparkling inground pool and hot tub. With ceiling fans and a TV, the covered porch is an inviting gathering space for morning coffee, lazy summer afternoons, or movie night—truly an extension of the home all year long. Inside, the main level offers an ideal blend of an open floorplan and defined rooms with gleaming hardwood floors, soaring ceilings, crown molding, beautiful fresh paint, and an abundance of natural light. The kitchen features generous cabinet storage and prep space,a gas cook top, double ovens, built in microwave, a center island, and breakfast nook with direct access to the covered porch and expansive patio & pool area, making indoor-outdoor entertaining effortless. From the kitchen flow into the spacious living room with charming built-ins to find a warm and inviting place to relax and watch TV while being part of the action. This home also has a formal dining and living room (currently used as office) that flank the welcoming and generously sized foyer. The large main-level primary suite offers a private retreat with a relaxing en-suite bath featuring a soaking tub, step in shower, and huge walk-in closet. The main level is also home to laundry room and gorgeous powder room. Upstairs, three generously sized bedrooms share a full bath, providing comfortable accommodations for family and guests along with a loft area perfect as play area or reading nook. The versatile lower level expands the living space with ceramic tile throughout, a spacious recreation area, full bath, and finished room with closet that could serve as a fifth bedroom, home office, guest space, gym, media room, or game room. Outside, the covered rear porch, expansive patio, inground pool, and hot tub create a backyard designed for enjoying home to the fullest. The inviting front porch adds another charming outdoor space, perfect for morning coffee or winding down at the end of the day. A two-car garage, newer roof (2025), two-zone HVAC, and desirable corner-lot setting add to the home's appeal. Meaningful updates include new pool cover (3 years old), pool pump (2 years old) and brand new sand filter. Located in the quiet, Oakdale Crossing neighborhood, this home offers convenient access to Jim Barnett Park, Shenandoah University, Schools, Costco, Apple Blossom Mall, Winchester Country Club, and everyday amenities. Whether you're looking for the ease of main-level living, a comfortable home for entertaining, or your own private backyard retreat, 200 Fairfield Drive offers a wonderful combination of comfort, convenience, and lifestyle.

4 Beds ⋅ 4 Baths

Come and discover this impressive beauty where easy main-level living meets exceptional indoor-outdoor entertaining. This beautifully appointed Cape Cod offers the convenience of a spacious main-level primary suite, while the heart of the home flows seamlessly from the well-appointed kitchen to a covered rear porch overlooking the sparkling inground pool and hot tub. With ceiling fans and a TV, the covered porch is an inviting gathering space for morning coffee, lazy summer afternoons, or movie night—truly an extension of the home all year long. Inside, the main level offers an ideal blend of an open floorplan and defined rooms with gleaming hardwood floors, soaring ceilings, crown molding, beautiful fresh paint, and an abundance of natural light. The kitchen features generous cabinet storage and prep space,a gas cook top, double ovens, built in microwave, a center island, and breakfast nook with direct access to the covered porch and expansive patio & pool area, making indoor-outdoor entertaining effortless. From the kitchen flow into the spacious living room with charming built-ins to find a warm and inviting place to relax and watch TV while being part of the action. This home also has a formal dining and living room (currently used as office) that flank the welcoming and generously sized foyer. The large main-level primary suite offers a private retreat with a relaxing en-suite bath featuring a soaking tub, step in shower, and huge walk-in closet. The main level is also home to laundry room and gorgeous powder room. Upstairs, three generously sized bedrooms share a full bath, providing comfortable accommodations for family and guests along with a loft area perfect as play area or reading nook. The versatile lower level expands the living space with ceramic tile throughout, a spacious recreation area, full bath, and finished room with closet that could serve as a fifth bedroom, home office, guest space, gym, media room, or game room. Outside, the covered rear porch, expansive patio, inground pool, and hot tub create a backyard designed for enjoying home to the fullest. The inviting front porch adds another charming outdoor space, perfect for morning coffee or winding down at the end of the day. A two-car garage, newer roof (2025), two-zone HVAC, and desirable corner-lot setting add to the home's appeal. Meaningful updates include new pool cover (3 years old), pool pump (2 years old) and brand new sand filter. Located in the quiet, Oakdale Crossing neighborhood, this home offers convenient access to Jim Barnett Park, Shenandoah University, Schools, Costco, Apple Blossom Mall, Winchester Country Club, and everyday amenities. Whether you're looking for the ease of main-level living, a comfortable home for entertaining, or your own private backyard retreat, 200 Fairfield Drive offers a wonderful combination of comfort, convenience, and lifestyle.

200 Fairfield Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$597,000

Welcome to this beautifully maintained home in the established Stonebrook Farms community, perfectly situated on a quiet cul-de-sac and surrounded by mature trees and landscaping. This inviting home offers a spacious and versatile floor plan, including a main-level bedroom and full bath—ideal for guests, multigenerational living, or anyone needing convenient main-level accommodations. At the heart of the home is a large family room featuring a wood-burning fireplace, creating a warm and welcoming space for gathering with family and friends. The home has been lovingly cared for, with pride of ownership evident throughout. One of the home's standout features is the beautiful covered and screened-in back porch, offering the perfect place for morning coffee, outdoor dining, or relaxing at the end of the day while overlooking the peaceful and beautifully maintained backyard. With its desirable cul-de-sac setting, flexible main-level living space, spacious family room, and wonderful outdoor living area, this well-maintained Stonebrook Farms home is ready to welcome its next owners!

5 Beds ⋅ 3 Baths

Welcome to this beautifully maintained home in the established Stonebrook Farms community, perfectly situated on a quiet cul-de-sac and surrounded by mature trees and landscaping. This inviting home offers a spacious and versatile floor plan, including a main-level bedroom and full bath—ideal for guests, multigenerational living, or anyone needing convenient main-level accommodations. At the heart of the home is a large family room featuring a wood-burning fireplace, creating a warm and welcoming space for gathering with family and friends. The home has been lovingly cared for, with pride of ownership evident throughout. One of the home's standout features is the beautiful covered and screened-in back porch, offering the perfect place for morning coffee, outdoor dining, or relaxing at the end of the day while overlooking the peaceful and beautifully maintained backyard. With its desirable cul-de-sac setting, flexible main-level living space, spacious family room, and wonderful outdoor living area, this well-maintained Stonebrook Farms home is ready to welcome its next owners!

102 Forest Valley Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$250,000

Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to relax or entertain. Conveniently located near shopping, dining and everyday amenities, with quick access to I-81 from Winchester's east side—making it an excellent option for commuters. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home in the city, this bungalow is worth a look. Schedule your showing today!

2 Beds ⋅ 1 Baths

Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to relax or entertain. Conveniently located near shopping, dining and everyday amenities, with quick access to I-81 from Winchester's east side—making it an excellent option for commuters. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home in the city, this bungalow is worth a look. Schedule your showing today!

1125 Conway St, Winchester

Listing courtesy of NextHome Realty Select. Contact:

$625,000

**BACK ON THE MARKET THROUGH NO FAULT OF THE SELLER! A rare opportunity to own a truly special farmhouse in a picturesque country setting! Originally built in 1911 and lovingly maintained by the same family for generations, this charming home offers the perfect blend of historic character, thoughtful updates, and modern-day comfort. Situated on 2.75 beautiful acres, this property offers the charm and possibilities of a small farmette, complete with a wonderful barn, spacious detached garage, and breathtaking views of the surrounding countryside. Over the years, the home has been carefully maintained, updated, and expanded with an addition that provides valuable extra living space. One of its most desirable features is the flexible floor plan offering TWO primary suites - one conveniently located on the main level and another upstairs - ideal for a variety of living arrangements. From the inviting farmhouse character to the peaceful setting and panoramic views enjoyed from nearly every window, there is something truly special about this property. Whether you envision enjoying quiet mornings overlooking the countryside, creating your own small farmette, or simply having room to spread out and enjoy country living, this property offers so much to love. A home with history, heart, and a setting that's hard to find. Come experience it for yourself!

4 Beds ⋅ 4 Baths

**BACK ON THE MARKET THROUGH NO FAULT OF THE SELLER! A rare opportunity to own a truly special farmhouse in a picturesque country setting! Originally built in 1911 and lovingly maintained by the same family for generations, this charming home offers the perfect blend of historic character, thoughtful updates, and modern-day comfort. Situated on 2.75 beautiful acres, this property offers the charm and possibilities of a small farmette, complete with a wonderful barn, spacious detached garage, and breathtaking views of the surrounding countryside. Over the years, the home has been carefully maintained, updated, and expanded with an addition that provides valuable extra living space. One of its most desirable features is the flexible floor plan offering TWO primary suites - one conveniently located on the main level and another upstairs - ideal for a variety of living arrangements. From the inviting farmhouse character to the peaceful setting and panoramic views enjoyed from nearly every window, there is something truly special about this property. Whether you envision enjoying quiet mornings overlooking the countryside, creating your own small farmette, or simply having room to spread out and enjoy country living, this property offers so much to love. A home with history, heart, and a setting that's hard to find. Come experience it for yourself!

394 Old Baltimore Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$319,990

Welcome to this adorable 3-bedroom, 2-full-bath cottage rancher home located on the East side of Winchester with NO HOA! Offering approximately 1,024 finished square feet on a generous .30-acre level lot, this property presents an excellent opportunity for both homeowners and investors. The home features an oversized two-car detached garage, providing plenty of room for vehicles, storage, hobbies, or a workshop. With no HOA, you’ll enjoy added flexibility and freedom to make the property your own. Custom updated bathrooms, Updated kitchen with stainless appliances, front porch & back patio! All this for an affordable price!

3 Beds ⋅ 2 Baths

Welcome to this adorable 3-bedroom, 2-full-bath cottage rancher home located on the East side of Winchester with NO HOA! Offering approximately 1,024 finished square feet on a generous .30-acre level lot, this property presents an excellent opportunity for both homeowners and investors. The home features an oversized two-car detached garage, providing plenty of room for vehicles, storage, hobbies, or a workshop. With no HOA, you’ll enjoy added flexibility and freedom to make the property your own. Custom updated bathrooms, Updated kitchen with stainless appliances, front porch & back patio! All this for an affordable price!

182 Mason St, Winchester

Listing courtesy of Young & Associates. Contact:

$340,000

Welcome home to this charming 3-bedroom, 2-bath house nestled on .32 acres, where comfortable living spaces and inviting outdoor areas come together to create a place that truly feels like home. The main level offers two bedrooms and a full bath, along with both a formal living room and an open family room, giving you plenty of space for quiet evenings, everyday living, and time spent with family and friends. The eat-in kitchen provides a welcoming spot to gather and flows into an enclosed porch. From the porch, step onto the deck overlooking the patio and backyard, where mature trees add shade, character, and a peaceful backdrop for outdoor entertaining or relaxing at the end of the day. Upstairs, the primary suite offers a private retreat all its own, complete with a full bathroom and a spacious sitting area/flex space that can easily be tailored to your needs. Whether you envision a home office, dressing area, reading nook, or cozy lounge this space is sure to please. With its flexible floor plan, multiple gathering spaces, private primary suite, and seamless connection to the outdoors, this home offers the space and versatility to settle in, make it your own, and enjoy for years to come.

3 Beds ⋅ 2 Baths

Welcome home to this charming 3-bedroom, 2-bath house nestled on .32 acres, where comfortable living spaces and inviting outdoor areas come together to create a place that truly feels like home. The main level offers two bedrooms and a full bath, along with both a formal living room and an open family room, giving you plenty of space for quiet evenings, everyday living, and time spent with family and friends. The eat-in kitchen provides a welcoming spot to gather and flows into an enclosed porch. From the porch, step onto the deck overlooking the patio and backyard, where mature trees add shade, character, and a peaceful backdrop for outdoor entertaining or relaxing at the end of the day. Upstairs, the primary suite offers a private retreat all its own, complete with a full bathroom and a spacious sitting area/flex space that can easily be tailored to your needs. Whether you envision a home office, dressing area, reading nook, or cozy lounge this space is sure to please. With its flexible floor plan, multiple gathering spaces, private primary suite, and seamless connection to the outdoors, this home offers the space and versatility to settle in, make it your own, and enjoy for years to come.

1077 Carpers Dr, Winchester

Listing courtesy of Burch Real Estate Group, LLC. Contact:

$659,900

Space, style, and room to live your best life come together in this 4-bedroom, 4.5-bath, 3-level Colonial in desirable Oakdale Crossing. With flexible spaces, great indoor-outdoor living, and a location close to everything Winchester has to offer, this home is ready for whatever comes next. The main level features an open, inviting flow between the kitchen, breakfast room, and family room, where a gas fireplace creates the perfect spot to unwind. The kitchen offers granite countertops, while the dining room, living room, and dedicated office give you plenty of flexibility for everyday life. Crown molding and hardwood floors adds a polished touch throughout the main level. Upstairs, the spacious primary suite is your private retreat, complete with a large bath featuring double sinks, a soaking tub, shower and walk-in closet. Two additional bedrooms share a full bath, while a fourth bedroom offers its own en-suite bathroom—ideal for guests or anyone who wants extra privacy. The conveniently located upper-level laundry room makes laundry day a whole lot easier. The walkout lower level is where the fun happens! A huge recreation room with a second gas fireplace gives you space for movie nights, game days, or your favorite hobbies; plus there is an exercise room. A full bathroom with walk-in shower adds even more flexibility. Step outside through the walkout level to the patio and enjoy views of the large backyard—perfect for relaxing, entertaining, or letting your outdoor space become whatever you want it to be or head up to the TimberTech deck for outdoor dining, morning coffee, or summer gatherings. With shopping, restaurants, schools, and Winchester Country Club all nearby, you'll have convenience without giving up the space and privacy of a larger home. Come see how easily this home can fit the way you live today—and all the possibilities ahead. Plus no HOA!!

4 Beds ⋅ 5 Baths

Space, style, and room to live your best life come together in this 4-bedroom, 4.5-bath, 3-level Colonial in desirable Oakdale Crossing. With flexible spaces, great indoor-outdoor living, and a location close to everything Winchester has to offer, this home is ready for whatever comes next. The main level features an open, inviting flow between the kitchen, breakfast room, and family room, where a gas fireplace creates the perfect spot to unwind. The kitchen offers granite countertops, while the dining room, living room, and dedicated office give you plenty of flexibility for everyday life. Crown molding and hardwood floors adds a polished touch throughout the main level. Upstairs, the spacious primary suite is your private retreat, complete with a large bath featuring double sinks, a soaking tub, shower and walk-in closet. Two additional bedrooms share a full bath, while a fourth bedroom offers its own en-suite bathroom—ideal for guests or anyone who wants extra privacy. The conveniently located upper-level laundry room makes laundry day a whole lot easier. The walkout lower level is where the fun happens! A huge recreation room with a second gas fireplace gives you space for movie nights, game days, or your favorite hobbies; plus there is an exercise room. A full bathroom with walk-in shower adds even more flexibility. Step outside through the walkout level to the patio and enjoy views of the large backyard—perfect for relaxing, entertaining, or letting your outdoor space become whatever you want it to be or head up to the TimberTech deck for outdoor dining, morning coffee, or summer gatherings. With shopping, restaurants, schools, and Winchester Country Club all nearby, you'll have convenience without giving up the space and privacy of a larger home. Come see how easily this home can fit the way you live today—and all the possibilities ahead. Plus no HOA!!

291 Huntersridge Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$439,000

LOWER YOUR MONTHLY PAYMENT FOR THE FIRST TWO YEARS! Seller is offering a credit that may be applied toward a 2,1 temporary interest rate buydown with an acceptable offer and approved financing. A 2,1 buydown provides an interest rate 2% below the note rate during the first year and 1% below the note rate during the second year, before returning to the full note rate in year three. Offer is subject to seller approval, loan program eligibility, lender requirements, and applicable contribution limits. NEWER HOME • NO HOA • WALK-OUT BASEMENT • MOVE-IN READY Discover a fresh opportunity at 114 Meadow Way! Built in 2021 and beautifully maintained, this 3-bedroom, 2.5-bath home combines the benefits of newer construction with a peaceful Winchester setting—and NO HOA. Step inside to a light-filled, open floor plan designed for today's lifestyle. The kitchen is the heart of the home, featuring crisp white cabinetry, quartz countertops, stainless steel appliances and a center island overlooking the living and dining areas—perfect for everyday living and entertaining. Upstairs, you'll find comfortable bedroom spaces and a well-designed primary suite, while the home's approximately 900-square-foot unfinished walk-out basement offers exciting possibilities for future expansion. Imagine a recreation room, home gym, office, hobby space or additional living area customized to your needs.* Outside, enjoy the composite deck, wooded surroundings and the convenience of an attached two-car garage. With approximately 1,711 finished square feet, newer construction, private well and septic, no HOA and substantial unfinished lower-level space, 114 Meadow Way offers something increasingly difficult to find in the Winchester market.

3 Beds ⋅ 3 Baths

LOWER YOUR MONTHLY PAYMENT FOR THE FIRST TWO YEARS! Seller is offering a credit that may be applied toward a 2,1 temporary interest rate buydown with an acceptable offer and approved financing. A 2,1 buydown provides an interest rate 2% below the note rate during the first year and 1% below the note rate during the second year, before returning to the full note rate in year three. Offer is subject to seller approval, loan program eligibility, lender requirements, and applicable contribution limits. NEWER HOME • NO HOA • WALK-OUT BASEMENT • MOVE-IN READY Discover a fresh opportunity at 114 Meadow Way! Built in 2021 and beautifully maintained, this 3-bedroom, 2.5-bath home combines the benefits of newer construction with a peaceful Winchester setting—and NO HOA. Step inside to a light-filled, open floor plan designed for today's lifestyle. The kitchen is the heart of the home, featuring crisp white cabinetry, quartz countertops, stainless steel appliances and a center island overlooking the living and dining areas—perfect for everyday living and entertaining. Upstairs, you'll find comfortable bedroom spaces and a well-designed primary suite, while the home's approximately 900-square-foot unfinished walk-out basement offers exciting possibilities for future expansion. Imagine a recreation room, home gym, office, hobby space or additional living area customized to your needs.* Outside, enjoy the composite deck, wooded surroundings and the convenience of an attached two-car garage. With approximately 1,711 finished square feet, newer construction, private well and septic, no HOA and substantial unfinished lower-level space, 114 Meadow Way offers something increasingly difficult to find in the Winchester market.

114 Meadow Way, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$615,000

Timeless brick-front style, three finished levels, and room for whatever comes next. At 922 Wayne Drive in the City of Winchester, an open kitchen and living area make it easy to gather, while a dedicated office, separate music room, and formal dining room give you spaces of their own. A two-story foyer sets the tone, with 9-foot ceilings on both the main and upper levels. On the main floor, bamboo flooring, fresh paint, and new crown molding complement the living room fireplace with new gas logs. New sliding glass doors open to a newly built deck with stairs to the yard, an easy spot to take dinner outside. Just off the kitchen, a mudroom with built-in seating and storage connects to the attached two-car garage. Upstairs, four bedrooms and a dedicated laundry room keep everyday routines on one level. New oak hardwood runs from the staircase through the landing, hallway, and primary suite, including its double-sided walk-in closet. The updated primary bath features app-controlled heated flooring. The hall bath has also been updated, and the other three bedrooms have new carpeting. The laundry room includes waterproof luxury vinyl tile, cabinetry, a folding counter, and a high-efficiency washer and dryer. Nearly 1,000 finished square feet on the lower level add a spacious recreation room with a separate entry, a full bath, and an additional laundry hookup. A separate finished bonus room without legal bedroom egress offers space for hobbies, exercise, or storage. Fresh paint and new carpeting give the level a fresh finish. Behind the scenes, upgrades include a Carrier HVAC system with a variable-speed inverter compressor, R-52 attic insulation, and a Tamko Titan architectural shingle roof rated for 50 years. The garage features insulated doors and smartphone controls. With approximately 3,700 finished square feet across three levels, 5 bedrooms, and 3.5 baths, this Winchester City home offers flexible spaces for everyday living, entertaining, and whatever comes next.

5 Beds ⋅ 4 Baths

Timeless brick-front style, three finished levels, and room for whatever comes next. At 922 Wayne Drive in the City of Winchester, an open kitchen and living area make it easy to gather, while a dedicated office, separate music room, and formal dining room give you spaces of their own. A two-story foyer sets the tone, with 9-foot ceilings on both the main and upper levels. On the main floor, bamboo flooring, fresh paint, and new crown molding complement the living room fireplace with new gas logs. New sliding glass doors open to a newly built deck with stairs to the yard, an easy spot to take dinner outside. Just off the kitchen, a mudroom with built-in seating and storage connects to the attached two-car garage. Upstairs, four bedrooms and a dedicated laundry room keep everyday routines on one level. New oak hardwood runs from the staircase through the landing, hallway, and primary suite, including its double-sided walk-in closet. The updated primary bath features app-controlled heated flooring. The hall bath has also been updated, and the other three bedrooms have new carpeting. The laundry room includes waterproof luxury vinyl tile, cabinetry, a folding counter, and a high-efficiency washer and dryer. Nearly 1,000 finished square feet on the lower level add a spacious recreation room with a separate entry, a full bath, and an additional laundry hookup. A separate finished bonus room without legal bedroom egress offers space for hobbies, exercise, or storage. Fresh paint and new carpeting give the level a fresh finish. Behind the scenes, upgrades include a Carrier HVAC system with a variable-speed inverter compressor, R-52 attic insulation, and a Tamko Titan architectural shingle roof rated for 50 years. The garage features insulated doors and smartphone controls. With approximately 3,700 finished square feet across three levels, 5 bedrooms, and 3.5 baths, this Winchester City home offers flexible spaces for everyday living, entertaining, and whatever comes next.

922 Wayne Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$409,000

PRICED BELOW RECENT APPRAISED VALUE. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level washer/dryer. The second level of the home offers a sitting area, primary bedroom with its own half bath and two addtional bedrooms with a shared bathroom. Accessed by the third bedroom, the attic offers a blank canvas and could be easily transformed into a secondary living area, home office, or a recreation and fitness room. Wide plank pine flooring remains throughout most of the home along with many traditional fiixtures. Recent improvements include a new gourmet kitchen with SS appliances, hvac, water heater, exterior clapboard cedar siding replaced where needed and new tile floors in the kitchen, main level bath and utility room. Step outside to the quaint backyard which offers an oasis for relaxation, play and gardening. The location of the home can't be beat. Just a few blocks to the pedestrian mall, one can experience a plethora of dining options, coffee shops, boutique stores, galleries and local social activities.

3 Beds ⋅ 3 Baths

PRICED BELOW RECENT APPRAISED VALUE. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level washer/dryer. The second level of the home offers a sitting area, primary bedroom with its own half bath and two addtional bedrooms with a shared bathroom. Accessed by the third bedroom, the attic offers a blank canvas and could be easily transformed into a secondary living area, home office, or a recreation and fitness room. Wide plank pine flooring remains throughout most of the home along with many traditional fiixtures. Recent improvements include a new gourmet kitchen with SS appliances, hvac, water heater, exterior clapboard cedar siding replaced where needed and new tile floors in the kitchen, main level bath and utility room. Step outside to the quaint backyard which offers an oasis for relaxation, play and gardening. The location of the home can't be beat. Just a few blocks to the pedestrian mall, one can experience a plethora of dining options, coffee shops, boutique stores, galleries and local social activities.

422 S Loudoun St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$1,100,000

Welcome to this inviting, beautifully maintained 6-bedroom, 4-full-bathroom, 2-half-bathroom all-brick home in the desirable Meadow Branch subdivision in Winchester, Virginia. Offering over 6,000 square feet of finished living space, this impressive residence combines generous room sizes, timeless construction, exceptional storage, and comfortable living spaces designed for both everyday life and entertaining. Set on approximately half a lot, the property features a welcoming U-shaped driveway, mature landscaping, and wonderful curb appeal. With no HOA, you have the freedom and flexibility to enjoy the property on your terms. Inside, the home offers an abundance of built-in cabinetry, custom closet storage, and storage solutions throughout, making it easy to keep even a large household organized. The spacious layout provides plenty of room for family, guests, work-from-home spaces, hobbies, and entertaining. The walk-out basement adds another valuable level of living and recreational space, with convenient access to the outdoors. With six bedrooms, four full bathrooms, and two half bathrooms, there is plenty of flexibility for a growing family or those who simply want room to spread out. Meticulously cared for and move-in ready, this substantial brick home offers the space, storage, privacy, and location that are increasingly hard to find. Enjoy the established beauty of Meadow Branch while being conveniently located in Winchester, with easy access to shopping, dining, schools, commuter routes, and all that the area has to offer. A rare opportunity to own a spacious, established home with exceptional storage and flexibility in one of Winchester's sought after communities.

6 Beds ⋅ 6 Baths

Welcome to this inviting, beautifully maintained 6-bedroom, 4-full-bathroom, 2-half-bathroom all-brick home in the desirable Meadow Branch subdivision in Winchester, Virginia. Offering over 6,000 square feet of finished living space, this impressive residence combines generous room sizes, timeless construction, exceptional storage, and comfortable living spaces designed for both everyday life and entertaining. Set on approximately half a lot, the property features a welcoming U-shaped driveway, mature landscaping, and wonderful curb appeal. With no HOA, you have the freedom and flexibility to enjoy the property on your terms. Inside, the home offers an abundance of built-in cabinetry, custom closet storage, and storage solutions throughout, making it easy to keep even a large household organized. The spacious layout provides plenty of room for family, guests, work-from-home spaces, hobbies, and entertaining. The walk-out basement adds another valuable level of living and recreational space, with convenient access to the outdoors. With six bedrooms, four full bathrooms, and two half bathrooms, there is plenty of flexibility for a growing family or those who simply want room to spread out. Meticulously cared for and move-in ready, this substantial brick home offers the space, storage, privacy, and location that are increasingly hard to find. Enjoy the established beauty of Meadow Branch while being conveniently located in Winchester, with easy access to shopping, dining, schools, commuter routes, and all that the area has to offer. A rare opportunity to own a spacious, established home with exceptional storage and flexibility in one of Winchester's sought after communities.

1030 Breckinridge Ln, Winchester

Listing courtesy of Samson Properties. Contact:

$340,000

Welcome to this charming Winchester cottage tucked away on a quiet little side street just off Route 7! Set on nearly a full acre right in town, this property offers a rare combination of space and convenience. The .92 acre lot features a small stream on the property, adding a peaceful natural element to the setting. A path will need to be established to access the creek area, creating an opportunity to make the space your own. Offering 3 bedrooms and 2 full bathrooms, this inviting home features a spacious primary suite, comfortable living spaces, and a fully fenced backyard with a fire pit perfect for relaxing or entertaining. The kitchen is a equipped with upgraded appliances, including a new double oven and triple rack dishwasher, making everyday cooking and entertaining a breeze. The spacious primary suite offers a comfortable retreat with an updated bathroom featuring a beautiful tile shower and double shower heads! Several important updates have already been taken care of, including a newer roof and a brand-new HVAC system installed just weeks ago, an electric anode installation to water heater 2024, Culigan Sulfur Cleer System in 2025, and a new Goodman heat pump and air handler in 2026. An unfinished walkout basement provides additional storage space, while the fully fenced backyard offers room to enjoy the outdoors. Conveniently located just off Route 7, this home is close to shopping, dining, and everyday amenities, while offering an easy commute for those traveling in and around Winchester. A wonderful opportunity for a first-time homebuyer, downsizer, or anyone looking for a charming home in a convenient location with several major updates already completed. Come see all this home has to offer!

3 Beds ⋅ 2 Baths

Welcome to this charming Winchester cottage tucked away on a quiet little side street just off Route 7! Set on nearly a full acre right in town, this property offers a rare combination of space and convenience. The .92 acre lot features a small stream on the property, adding a peaceful natural element to the setting. A path will need to be established to access the creek area, creating an opportunity to make the space your own. Offering 3 bedrooms and 2 full bathrooms, this inviting home features a spacious primary suite, comfortable living spaces, and a fully fenced backyard with a fire pit perfect for relaxing or entertaining. The kitchen is a equipped with upgraded appliances, including a new double oven and triple rack dishwasher, making everyday cooking and entertaining a breeze. The spacious primary suite offers a comfortable retreat with an updated bathroom featuring a beautiful tile shower and double shower heads! Several important updates have already been taken care of, including a newer roof and a brand-new HVAC system installed just weeks ago, an electric anode installation to water heater 2024, Culigan Sulfur Cleer System in 2025, and a new Goodman heat pump and air handler in 2026. An unfinished walkout basement provides additional storage space, while the fully fenced backyard offers room to enjoy the outdoors. Conveniently located just off Route 7, this home is close to shopping, dining, and everyday amenities, while offering an easy commute for those traveling in and around Winchester. A wonderful opportunity for a first-time homebuyer, downsizer, or anyone looking for a charming home in a convenient location with several major updates already completed. Come see all this home has to offer!

197 Denny Ln, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$360,000

Nestled in the Shawneeland community, this delightful Colonial home, built in 2021, offers a perfect blend of modern comfort and timeless appeal. With three spacious bedrooms and two and a half bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover warm hardwood floors that flow throughout the main living areas, creating an inviting atmosphere. The heart of the home features a cozy breakfast area, perfect for morning gatherings or casual meals. The kitchen offers appliances, including an electric oven/range, refrigerator, microwave, and dishwasher, making meal prep a breeze. The primary suite is a true retreat, complete with an en-suite bathroom that offers both privacy and convenience. Additional bedrooms provide ample space for guests or a home office, catering to your lifestyle needs. The full, unfinished basement presents a blank canvas, ready for your personal touch—imagine a game room, home gym, or extra storage. With a walkout level, windows, and plumbing for a future bathroom, this space has great potential. Outside, the generous 0.32-acre lot offers plenty of room for outdoor activities or gardening, while the driveway provides convenient parking. Enjoy the tranquility of suburban living while being just a short drive from local amenities. This home is not just a place to live; it’s a place to create lasting memories. Don’t miss the opportunity to make it yours! PRICE ADJUSTMENT!!!! Schedule your appointment NOW!

3 Beds ⋅ 3 Baths

Nestled in the Shawneeland community, this delightful Colonial home, built in 2021, offers a perfect blend of modern comfort and timeless appeal. With three spacious bedrooms and two and a half bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover warm hardwood floors that flow throughout the main living areas, creating an inviting atmosphere. The heart of the home features a cozy breakfast area, perfect for morning gatherings or casual meals. The kitchen offers appliances, including an electric oven/range, refrigerator, microwave, and dishwasher, making meal prep a breeze. The primary suite is a true retreat, complete with an en-suite bathroom that offers both privacy and convenience. Additional bedrooms provide ample space for guests or a home office, catering to your lifestyle needs. The full, unfinished basement presents a blank canvas, ready for your personal touch—imagine a game room, home gym, or extra storage. With a walkout level, windows, and plumbing for a future bathroom, this space has great potential. Outside, the generous 0.32-acre lot offers plenty of room for outdoor activities or gardening, while the driveway provides convenient parking. Enjoy the tranquility of suburban living while being just a short drive from local amenities. This home is not just a place to live; it’s a place to create lasting memories. Don’t miss the opportunity to make it yours! PRICE ADJUSTMENT!!!! Schedule your appointment NOW!

147 Doe Trl, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$475,000

Nestled in the charming Apple Ridge community, this delightful Colonial home offers a perfect blend of comfort and convenience. With 2,528 sq. ft. of living space, this residence features five spacious bedrooms and 2.5 bathrooms, ideal for creating lasting memories. The inviting layout is perfect for both relaxation and entertaining. Apple Ridge is known for its friendly atmosphere and vibrant community spirit. Enjoy leisurely strolls through nearby parks, where lush green spaces invite picnics and play. Convenient access to local amenities, shopping, and dining makes everyday life a breeze. The attached garage provides easy parking and storage solutions. With a lot size of 0.22 acres, there's ample outdoor space for gardening or enjoying the fresh air. This home is not just a place to live; it's a gateway to a warm and welcoming community. Experience the joy of living in Apple Ridge!

5 Beds ⋅ 3 Baths

Nestled in the charming Apple Ridge community, this delightful Colonial home offers a perfect blend of comfort and convenience. With 2,528 sq. ft. of living space, this residence features five spacious bedrooms and 2.5 bathrooms, ideal for creating lasting memories. The inviting layout is perfect for both relaxation and entertaining. Apple Ridge is known for its friendly atmosphere and vibrant community spirit. Enjoy leisurely strolls through nearby parks, where lush green spaces invite picnics and play. Convenient access to local amenities, shopping, and dining makes everyday life a breeze. The attached garage provides easy parking and storage solutions. With a lot size of 0.22 acres, there's ample outdoor space for gardening or enjoying the fresh air. This home is not just a place to live; it's a gateway to a warm and welcoming community. Experience the joy of living in Apple Ridge!

102 Primrose Pl, Winchester

Listing courtesy of Corcoran McEnearney. Contact:

$274,000

This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water heater installed in 2012 and the oil furnace is a newer model. This house currently is winterized and electricity shut off. (There is no lighting in the basement.)

3 Beds ⋅ 2 Baths

This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water heater installed in 2012 and the oil furnace is a newer model. This house currently is winterized and electricity shut off. (There is no lighting in the basement.)

519 Virginia Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$450,000

$450,000 4 bedrooms, 2 Full baths, (Price is negotiable!) 2,493 square feet living space with a full basement 501 Fox drive is strategically located 1.5 miles from the Valley Health Hospital, 1.4 miles from James Wood High School and one mile from the highway at Route 37. Talk about great location!….This four bedroom family home is on a perfect corner lot for added space. Recently renovated with Fresh paint throughout, New laminate flooring, New blinds, Updated bathroom that includes a new sink/cabinet and a new toilet, The bedrooms include new carpeting and new ceiling fans. The new renovations also include a brand new dishwasher and dryer. To add on to the list this property add's new backyard fencing and new all weather 10 X 12 storage unit. Dream house for the first time buyer, Don’t miss this opportunity!

4 Beds ⋅ 2 Baths

$450,000 4 bedrooms, 2 Full baths, (Price is negotiable!) 2,493 square feet living space with a full basement 501 Fox drive is strategically located 1.5 miles from the Valley Health Hospital, 1.4 miles from James Wood High School and one mile from the highway at Route 37. Talk about great location!….This four bedroom family home is on a perfect corner lot for added space. Recently renovated with Fresh paint throughout, New laminate flooring, New blinds, Updated bathroom that includes a new sink/cabinet and a new toilet, The bedrooms include new carpeting and new ceiling fans. The new renovations also include a brand new dishwasher and dryer. To add on to the list this property add's new backyard fencing and new all weather 10 X 12 storage unit. Dream house for the first time buyer, Don’t miss this opportunity!

501 Fox Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$425,000

SPECIAL FINANCING INCENTIVE! Qualified buyers may be eligible for a lender-paid 1-0 rate buydown, potentially saving approximately $270/month in principal and interest during the first year! Ask for details. Terms apply. PLUS, SELLERS ARE OFFERING A $5,000 CREDIT toward a mini-split OR closing cost assistance! Situated on 0.38 acres, this beautiful rancher features an expansive, level, fully fenced backyard shaded by gorgeous mature trees. A large rear deck incorporates a charming stock-tank plunge pool with liner and filtration system, perfect for relaxing and entertaining! Inside, you’ll find a beautifully renovated kitchen and a primary suite featuring a walk-in closet and remodeled en suite bathroom with walk-in shower. The lower level offers additional living and entertaining space, with over half the basement finished, a wet bar, and walk-up access to the backyard. Recent improvements include furnace and electrical upgrades, including an updated breaker panel wired for a backup generator (generator not included). Additional features include a carport, hallway bathroom heat lamp for those chilly fall nights, and high-speed internet.

3 Beds ⋅ 2 Baths

SPECIAL FINANCING INCENTIVE! Qualified buyers may be eligible for a lender-paid 1-0 rate buydown, potentially saving approximately $270/month in principal and interest during the first year! Ask for details. Terms apply. PLUS, SELLERS ARE OFFERING A $5,000 CREDIT toward a mini-split OR closing cost assistance! Situated on 0.38 acres, this beautiful rancher features an expansive, level, fully fenced backyard shaded by gorgeous mature trees. A large rear deck incorporates a charming stock-tank plunge pool with liner and filtration system, perfect for relaxing and entertaining! Inside, you’ll find a beautifully renovated kitchen and a primary suite featuring a walk-in closet and remodeled en suite bathroom with walk-in shower. The lower level offers additional living and entertaining space, with over half the basement finished, a wet bar, and walk-up access to the backyard. Recent improvements include furnace and electrical upgrades, including an updated breaker panel wired for a backup generator (generator not included). Additional features include a carport, hallway bathroom heat lamp for those chilly fall nights, and high-speed internet.

413 Superior Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$299,900

A wonderful home, lovingly cared for and ready for you! Situated in a great location, this home has so much to offer. Relax on the covered front porch before stepping inside to a bright and inviting main level featuring rich hardwood floors and a spacious eat-in kitchen with plentiful cabinet space. Two sizable bedrooms and a full bath round out the main floor for comfortable, easy living. The upper level serves as an expansive additional bedroom full of original charm, showcasing warm hardwood floors and classic wood-accented walls alongside custom built-in shelving, an integrated dresser, and a cedar-lined closet. This versatile space offers endless possibilities to suit your lifestyle—whether you want a private primary suite, home office, or hobby room. The full, unfinished basement offers massive storage capacity, laundry facilities, chairlift access, and a dedicated workshop space perfect for tools and DIY projects. Outside, the large, fully fenced backyard is a rare find for a city lot—giving you plenty of room to garden, host, or let pets play freely, as well as a shed for handy outdoor storage. All of this is situated just blocks from Jim Barnett Park and Daniel Morgan Middle School, with quick access to local shopping, dining, historic downtown Winchester, and major commuter routes.

3 Beds ⋅ 1 Baths

A wonderful home, lovingly cared for and ready for you! Situated in a great location, this home has so much to offer. Relax on the covered front porch before stepping inside to a bright and inviting main level featuring rich hardwood floors and a spacious eat-in kitchen with plentiful cabinet space. Two sizable bedrooms and a full bath round out the main floor for comfortable, easy living. The upper level serves as an expansive additional bedroom full of original charm, showcasing warm hardwood floors and classic wood-accented walls alongside custom built-in shelving, an integrated dresser, and a cedar-lined closet. This versatile space offers endless possibilities to suit your lifestyle—whether you want a private primary suite, home office, or hobby room. The full, unfinished basement offers massive storage capacity, laundry facilities, chairlift access, and a dedicated workshop space perfect for tools and DIY projects. Outside, the large, fully fenced backyard is a rare find for a city lot—giving you plenty of room to garden, host, or let pets play freely, as well as a shed for handy outdoor storage. All of this is situated just blocks from Jim Barnett Park and Daniel Morgan Middle School, with quick access to local shopping, dining, historic downtown Winchester, and major commuter routes.

12 N Purcell Ave, Winchester

Listing courtesy of Colony Realty. Contact:

600 Winchester Dr Unit LOT 17, Winchester

$359,000

Blue Ocean Modulars introduces The Laurel, a three-bedroom, two-full-bath ranch home to be built in the Wilde Acres subdivision of Frederick County. Nestled against a forested backdrop and built with high-quality workmanship, this residence showcases modern construction designed for durability, comfort, and long-term value. The home features Insul-Stud framing, a cutting-edge system that enhances insulation and significantly improves energy efficiency. From foundation to finishing details, every element reflects careful attention to design and build quality, making it a standout choice in Frederick County’s housing market. Wilde Acres is about 1/2 hour southwest of Winchester, Virginia, on the eastern face of Great North Mountain. Listing photos show a deck. This is an optional add-on feature.

3 Beds ⋅ 2 Baths

Blue Ocean Modulars introduces The Laurel, a three-bedroom, two-full-bath ranch home to be built in the Wilde Acres subdivision of Frederick County. Nestled against a forested backdrop and built with high-quality workmanship, this residence showcases modern construction designed for durability, comfort, and long-term value. The home features Insul-Stud framing, a cutting-edge system that enhances insulation and significantly improves energy efficiency. From foundation to finishing details, every element reflects careful attention to design and build quality, making it a standout choice in Frederick County’s housing market. Wilde Acres is about 1/2 hour southwest of Winchester, Virginia, on the eastern face of Great North Mountain. Listing photos show a deck. This is an optional add-on feature.

600 Winchester Dr Unit LOT 17, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$485,000

Welcome to 307 Canyon Road in Winchesters sought-after Senseny Glen community. This move-in-ready ranch style home offers open-concept main-level living boasting hardwood floors, plush carpet, a cozy gas fireplace, and an abundance of natural light throughout! The kitchen includes ample cabinetry and pantry storage, a large island for breakfast seating, all positioned perfectly with the dining and living areas. The thoughtful split bedroom layout features two spacious guest rooms with a full bath on one side, and a private primary suite on the other, complete with a generous ensuite full bath and dual walk-in closets. Upstairs, a finished bonus bedroom above the 2-car garage provides flexible space for living, home office, gym, or media room. Outside, enjoy a welcoming front porch and a private side patio just off the kitchen, perfect for quiet mornings or casual gatherings on this beautiful .29 acre corner lot. Ideally positioned for easy commuter access to Rte. 7, 81 & beyond. Meticulously maintained, and with many recent improvements, this is a wonderful opportunity in a superb location, schedule your private tour today!

4 Beds ⋅ 2 Baths

Welcome to 307 Canyon Road in Winchesters sought-after Senseny Glen community. This move-in-ready ranch style home offers open-concept main-level living boasting hardwood floors, plush carpet, a cozy gas fireplace, and an abundance of natural light throughout! The kitchen includes ample cabinetry and pantry storage, a large island for breakfast seating, all positioned perfectly with the dining and living areas. The thoughtful split bedroom layout features two spacious guest rooms with a full bath on one side, and a private primary suite on the other, complete with a generous ensuite full bath and dual walk-in closets. Upstairs, a finished bonus bedroom above the 2-car garage provides flexible space for living, home office, gym, or media room. Outside, enjoy a welcoming front porch and a private side patio just off the kitchen, perfect for quiet mornings or casual gatherings on this beautiful .29 acre corner lot. Ideally positioned for easy commuter access to Rte. 7, 81 & beyond. Meticulously maintained, and with many recent improvements, this is a wonderful opportunity in a superb location, schedule your private tour today!

307 Canyon Rd, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

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