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Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a home built in 1825, this unique property is just a short stroll to Winchester's favorite restaurants, boutique shopping, coffee shops, museums, and downtown events. Renovated in 2021, the condo offers stylish updates while preserving its historic character. The kitchen features quartz countertops, stainless steel appliances, a new refrigerator, and a new island with an integrated sink that creates the perfect gathering space. Fresh paint, modern lighting, a beautifully updated bathroom, and a built-in bookcase add to the home's appeal. The exposed brick fireplace serves as a striking architectural feature, adding warmth and character to the living room. (Fireplace is decorative only.) Whether you're looking for your own place in the heart of downtown or an investment opportunity, this low-maintenance condo offers the best of both worlds; historic charm, modern finishes, and an unbeatable location where you can leave the car behind and enjoy everything Winchester has to offer.

1 Beds ⋅ 1 Baths

Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a home built in 1825, this unique property is just a short stroll to Winchester's favorite restaurants, boutique shopping, coffee shops, museums, and downtown events. Renovated in 2021, the condo offers stylish updates while preserving its historic character. The kitchen features quartz countertops, stainless steel appliances, a new refrigerator, and a new island with an integrated sink that creates the perfect gathering space. Fresh paint, modern lighting, a beautifully updated bathroom, and a built-in bookcase add to the home's appeal. The exposed brick fireplace serves as a striking architectural feature, adding warmth and character to the living room. (Fireplace is decorative only.) Whether you're looking for your own place in the heart of downtown or an investment opportunity, this low-maintenance condo offers the best of both worlds; historic charm, modern finishes, and an unbeatable location where you can leave the car behind and enjoy everything Winchester has to offer.

135 S Kent St Unit 202, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$329,900

FABULOUS PRICE REDUCTION!!! Why wait to build? This beautifully finished, move-in-ready home offers all the benefits of new construction without the wait. Offering modern style, quality craftsmanship, and low-maintenance living a short distance from Winchester this new home is nestled on a beautiful lot in Wilde Acres. This thoughtfully designed 3-bedroom, 2-bath home features an open floor plan with luxury vinyl plank flooring and today’s most sought-after finishes. The spacious kitchen is the heart of the home, showcasing granite countertops, a large peninsula, stainless steel appliances, white shaker cabinetry, and black fixtures. The primary suite offers a private bath with granite countertops and a walk-in shower, while two additional bedrooms provide space for family, guests, or a home office. The finished lower-level family room offers flexible living space for entertaining, recreation, or remote work, and the oversized garage provides great storage. Enjoy the peace and privacy of mountain living with convenient access to Mountain Falls Park, featuring a lake, playground, picnic area, and outdoor recreation. Move-in ready and thoughtfully finished throughout, this home offers the perfect blend of comfort, style and value. Some photos virtually staged. Owner/agent.

3 Beds ⋅ 2 Baths

FABULOUS PRICE REDUCTION!!! Why wait to build? This beautifully finished, move-in-ready home offers all the benefits of new construction without the wait. Offering modern style, quality craftsmanship, and low-maintenance living a short distance from Winchester this new home is nestled on a beautiful lot in Wilde Acres. This thoughtfully designed 3-bedroom, 2-bath home features an open floor plan with luxury vinyl plank flooring and today’s most sought-after finishes. The spacious kitchen is the heart of the home, showcasing granite countertops, a large peninsula, stainless steel appliances, white shaker cabinetry, and black fixtures. The primary suite offers a private bath with granite countertops and a walk-in shower, while two additional bedrooms provide space for family, guests, or a home office. The finished lower-level family room offers flexible living space for entertaining, recreation, or remote work, and the oversized garage provides great storage. Enjoy the peace and privacy of mountain living with convenient access to Mountain Falls Park, featuring a lake, playground, picnic area, and outdoor recreation. Move-in ready and thoughtfully finished throughout, this home offers the perfect blend of comfort, style and value. Some photos virtually staged. Owner/agent.

503 Grouse, Winchester

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

$569,000

ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA! Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas fireplace. The spacious gourmet kitchen offers granite countertops, stainless steel appliances, generous pantry space and a large breakfast area that flows easily into the dining and living spaces—perfect for everyday living and entertaining. One of this home's standout features is its main-level living potential. The primary suite is conveniently located on the main floor with a private bath and walk-in closet, while a second main-level bedroom and nearby full bath provide exceptional flexibility for guests, a home office or additional living space. Main-level laundry with a utility sink adds even more convenience. Upstairs, you'll discover a private and versatile living area with its own main-level entrance, sitting/living space, two additional bedrooms and a full bath—creating an ideal setup for extended stays, guests, work-from-home needs or anyone wanting additional privacy and separation. And there's even more! The detached two-car garage includes additional finished living space above, complete with a bedroom, full bath and kitchen/living area—opening the door to an incredible variety of possibilities. Outside, enjoy multiple parking options with front and rear driveways, an attached covered carport, detached garage and additional street parking. All of this is tucked into an established Winchester neighborhood convenient to downtown Winchester, Route 7, shopping, dining, medical facilities and major commuter routes. All brick. Four full baths. Two main-level bedrooms. Flexible living spaces. Detached garage. No HOA. This isn't your typical Winchester home—come see just how many possibilities 687 Woodland Avenue has to offer.

4 Beds ⋅ 4 Baths

ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA! Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas fireplace. The spacious gourmet kitchen offers granite countertops, stainless steel appliances, generous pantry space and a large breakfast area that flows easily into the dining and living spaces—perfect for everyday living and entertaining. One of this home's standout features is its main-level living potential. The primary suite is conveniently located on the main floor with a private bath and walk-in closet, while a second main-level bedroom and nearby full bath provide exceptional flexibility for guests, a home office or additional living space. Main-level laundry with a utility sink adds even more convenience. Upstairs, you'll discover a private and versatile living area with its own main-level entrance, sitting/living space, two additional bedrooms and a full bath—creating an ideal setup for extended stays, guests, work-from-home needs or anyone wanting additional privacy and separation. And there's even more! The detached two-car garage includes additional finished living space above, complete with a bedroom, full bath and kitchen/living area—opening the door to an incredible variety of possibilities. Outside, enjoy multiple parking options with front and rear driveways, an attached covered carport, detached garage and additional street parking. All of this is tucked into an established Winchester neighborhood convenient to downtown Winchester, Route 7, shopping, dining, medical facilities and major commuter routes. All brick. Four full baths. Two main-level bedrooms. Flexible living spaces. Detached garage. No HOA. This isn't your typical Winchester home—come see just how many possibilities 687 Woodland Avenue has to offer.

687 Woodland Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,175,000

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

6 Beds ⋅ 7 Baths

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm and contemporary convenience across 8,593 finished square feet, featuring 6 bedrooms, 5 full baths, and 2 half baths. The heart of the residence is the original 1765 portion, which stands as a museum-quality testament to early American craftsmanship. It showcases meticulously preserved original flooring, windows, doors, period hardware, stately mantles, and staircase. As the estate evolved, a first major addition was seamlessly introduced in 1940, followed by a second grand addition in 2000. True to the property's legacy of excellence, the 1940 wing underwent a major, high-end renovation in 2019 to ensure flawless modern style. Yet, behind the historic craftsmanship lies a completely modernized infrastructure: the entire home boasts fully updated plumbing, electrical, and central heating and A/C. Step outside to find your own secluded sanctuary, complete with a natural spring and a picturesque pond. This is a living piece of art, offering the perfect synergy of historical beauty, absolute privacy, and contemporary convenience. For additional information, full ownership history starting in 1735 and comprehensive renovation highlights please view the accompanying documents. Schedule your private tour to experience this once-in-a-lifetime legacy property. See accompanying files for full Historical Lineage starting in 1735, and details about the architecture and features.

730 Merrimans Ln, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$369,990

Main-level living at its best in Hiatt Pointe at Snowden Bridge—a gated 55+ active adult community. This low-maintenance villa features a primary bedroom and laundry on the entry level, a screened rear porch, and a one-car garage. Upstairs offers two spacious bedrooms with walk-in closets and a full bath, plus a finished storage area! Enjoy a stylish kitchen with quartz counters, stainless steel appliances, and white elegant cabinetry. Resort-style amenities include pickleball and bocce courts, clubhouse, fitness and yoga studios, outdoor kitchen, pool and hot tub—plus snow removal, trash, and recycling included. Ask about builder incentives today!

3 Beds ⋅ 3 Baths

Main-level living at its best in Hiatt Pointe at Snowden Bridge—a gated 55+ active adult community. This low-maintenance villa features a primary bedroom and laundry on the entry level, a screened rear porch, and a one-car garage. Upstairs offers two spacious bedrooms with walk-in closets and a full bath, plus a finished storage area! Enjoy a stylish kitchen with quartz counters, stainless steel appliances, and white elegant cabinetry. Resort-style amenities include pickleball and bocce courts, clubhouse, fitness and yoga studios, outdoor kitchen, pool and hot tub—plus snow removal, trash, and recycling included. Ask about builder incentives today!

404 Granite Ridge Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

$244,900

SELLER INCENTIVE! Seller is offering a credit of up to 3% of the purchase price toward a qualified buyer’s 2-1 temporary interest rate buydown, subject to lender approval and program guidelines. This is a great opportunity for qualified buyers to reduce their interest rate during the first two years of homeownership. Discover the charm of Parkplace Condominiums, where comfort meets convenience in a vibrant community. This inviting 2-bedroom, 2-bathroom unit features modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven, making meal prep a delight. Enjoy the ease of in-unit laundry with washer and dryer hookups, ensuring your daily routines are seamless. Nestled in a friendly neighborhood, residents benefit from well-maintained grounds with included lawn care, snow removal, and trash services. The community is close to local parks, perfect for leisurely strolls or weekend picnics. Excellent schools are just a stone's throw away, providing quality education options for all ages. With a strong sense of community and convenient access to public services, Parkplace is more than just a home; it's a place to create lasting memories. Experience the warmth and comfort of this lovely unit, where every detail is designed for your enjoyment.

2 Beds ⋅ 2 Baths

SELLER INCENTIVE! Seller is offering a credit of up to 3% of the purchase price toward a qualified buyer’s 2-1 temporary interest rate buydown, subject to lender approval and program guidelines. This is a great opportunity for qualified buyers to reduce their interest rate during the first two years of homeownership. Discover the charm of Parkplace Condominiums, where comfort meets convenience in a vibrant community. This inviting 2-bedroom, 2-bathroom unit features modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven, making meal prep a delight. Enjoy the ease of in-unit laundry with washer and dryer hookups, ensuring your daily routines are seamless. Nestled in a friendly neighborhood, residents benefit from well-maintained grounds with included lawn care, snow removal, and trash services. The community is close to local parks, perfect for leisurely strolls or weekend picnics. Excellent schools are just a stone's throw away, providing quality education options for all ages. With a strong sense of community and convenient access to public services, Parkplace is more than just a home; it's a place to create lasting memories. Experience the warmth and comfort of this lovely unit, where every detail is designed for your enjoyment.

136 Brookland Ct Unit 6, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$1,800,000

4.93 acres with great interstate exposure. End of cul de sac. Owners have proposed platt showing parcel subdivided into 4 parcels

Sulky, Winchester

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

$1,239,000

This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy. Inside, you will find a stunning kitchen with top-of-the-line appliances and pull-out drawers throughout the cabinets. The great room is a 2 story ceiling and fireplace leading to the deck and wet bar with ice machine and wine racks. The main level office has a full bath attached if you would like to use it as a main level bedroom. The living and dining rooms are open to each other leading to a sunroom off the deck. The primary bedroom as a gas fireplace, a balcony , 2 walk in closets and an updated spa like bathroom. The second bedroom has it's own bath and the 3rd and 4th bedrooms share a full bath with updated tile and floors. The basement also has a fireplace, a full bath, exercise room and plenty of storage. The pool room (in the basement leading to the pool) has a refrigerator, storage for towels and a 1/2 bath. The 3 car garage has a ton of storage, as the original kitchen cabinets are on the wall...This home is truly a showcase!

4 Beds ⋅ 8 Baths

This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy. Inside, you will find a stunning kitchen with top-of-the-line appliances and pull-out drawers throughout the cabinets. The great room is a 2 story ceiling and fireplace leading to the deck and wet bar with ice machine and wine racks. The main level office has a full bath attached if you would like to use it as a main level bedroom. The living and dining rooms are open to each other leading to a sunroom off the deck. The primary bedroom as a gas fireplace, a balcony , 2 walk in closets and an updated spa like bathroom. The second bedroom has it's own bath and the 3rd and 4th bedrooms share a full bath with updated tile and floors. The basement also has a fireplace, a full bath, exercise room and plenty of storage. The pool room (in the basement leading to the pool) has a refrigerator, storage for towels and a 1/2 bath. The 3 car garage has a ton of storage, as the original kitchen cabinets are on the wall...This home is truly a showcase!

1022 Heth Pl, Winchester

Listing courtesy of Samson Properties. Contact:

$339,500

SELLER OFFERING UP TO $8,000 TOWARD BUYER'S CLOSING COSTS WITH AN ACCEPTABLE OFFER! Brand-new construction, modern finishes, and community amenities! Welcome to this beautifully finished 3-bedroom, 2-bath split-level home in Mountain Falls Park, situated on a spacious 0.26-acre lot. Offering approximately 2,000 finished square feet, this move-in-ready home combines contemporary style with everyday functionality. A welcoming covered front porch sets the tone as you step inside to find luxury vinyl plank flooring throughout and a bright, modern feel. The kitchen features stainless steel appliances, stylish shaker-style cabinetry, and granite countertops, creating an attractive and functional space for everyday meals and entertaining. The primary bath also features granite countertops and a convenient stall shower, while all three bedrooms offer built-in closet shelving for added organization and storage. The lower level provides a spacious family room with plenty of room to relax, gather, or entertain, along with a dedicated laundry room. An oversized two-car garage measuring approximately 20'10" x 23'2" offers ample space for vehicles, storage, hobbies, or projects. Enjoy the added appeal of Mountain Falls Park community amenities, including a common area, lake, picnic area, playground, and more. With brand-new construction, modern finishes, a generous lot, and access to outdoor recreation, this home is an excellent opportunity for buyers seeking comfort, convenience, and a fresh start. Be sure to check out the attached property video!

3 Beds ⋅ 2 Baths

SELLER OFFERING UP TO $8,000 TOWARD BUYER'S CLOSING COSTS WITH AN ACCEPTABLE OFFER! Brand-new construction, modern finishes, and community amenities! Welcome to this beautifully finished 3-bedroom, 2-bath split-level home in Mountain Falls Park, situated on a spacious 0.26-acre lot. Offering approximately 2,000 finished square feet, this move-in-ready home combines contemporary style with everyday functionality. A welcoming covered front porch sets the tone as you step inside to find luxury vinyl plank flooring throughout and a bright, modern feel. The kitchen features stainless steel appliances, stylish shaker-style cabinetry, and granite countertops, creating an attractive and functional space for everyday meals and entertaining. The primary bath also features granite countertops and a convenient stall shower, while all three bedrooms offer built-in closet shelving for added organization and storage. The lower level provides a spacious family room with plenty of room to relax, gather, or entertain, along with a dedicated laundry room. An oversized two-car garage measuring approximately 20'10" x 23'2" offers ample space for vehicles, storage, hobbies, or projects. Enjoy the added appeal of Mountain Falls Park community amenities, including a common area, lake, picnic area, playground, and more. With brand-new construction, modern finishes, a generous lot, and access to outdoor recreation, this home is an excellent opportunity for buyers seeking comfort, convenience, and a fresh start. Be sure to check out the attached property video!

604 Gatling Dr, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$1,724,000

Beautifully restored and fully modernized mixed-use building in the heart of historic Winchester. This exceptional offering includes a fully leased commercial building with three strong-credit tenants, a valuable adjacent parking lot approved for future mixed-use development, and a third floor ready for residential conversion. Located just one block from the historic Old Town Winchester Walking Mall, this legacy investment property offers more than 9,300 square feet of space with the first and second floors completely renovated and occupied. The third floor presents an outstanding value-add opportunity for apartment development, with potential eligibility for Historic Tax Credits. The property is also located within an Enterprise Zone, providing access to additional grant and incentive programs. The sale includes the adjacent parking lot (Tax ID 173-01-E-1), which is approved for multifamily development or can continue to serve as a highly desirable dedicated parking facility for tenants and customers. Current net operating income exceeds $80,000 annually, providing immediate cash flow with significant upside potential. Recent capital improvements include a metal roof, new HVAC systems, and modern tenant build-outs throughout the building. This unique asset offers a diversified income stream with retail and office tenants in place, while creating future opportunities for residential development on both the third floor and the adjacent parking lot. Ideal for a 1031 exchange buyer or investor seeking stable income, long-term appreciation, and redevelopment potential in one of the Shenandoah Valley's most desirable downtown locations. Conveniently located one block from the Braddock Street Parking Garage. Rarely does an opportunity of this caliber become available in Downtown Winchester. Contact the listing agent to schedule a private showing.

48 W Boscawen, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$290,000

Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning insert, and laminate flooring throughout. Enjoy sun and shade from the comfortable deck and spacious yard with plenty of room for outdoor gatherings, gardening, or creating your own private oasis. The community features acres of greenspace, a large lake, several ponds, and playgrounds. Don't miss the opportunity to make this cozy retreat your own!

3 Beds ⋅ 2 Baths

Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning insert, and laminate flooring throughout. Enjoy sun and shade from the comfortable deck and spacious yard with plenty of room for outdoor gatherings, gardening, or creating your own private oasis. The community features acres of greenspace, a large lake, several ponds, and playgrounds. Don't miss the opportunity to make this cozy retreat your own!

132 Geronimo Trl, Winchester

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

$44,900

"Build Your Home On Henry" This beautiful 3-Acre lot is located in Mountain Falls Park. With mature trees you can enjoy your privacy. Enjoy the community lake, common area, playground and picnic area! Has a 3-bedroom perc. Bring your vision to life!

Henry Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$724,900

This home is where space, comfort and flexibility come together in a home designed to grow with you. Tucked away on a quiet dead-end street, this spacious home offers room to spread out while still feeling warm and inviting. A sought-after main-level owner’s suite makes everyday living easy, while the generous floor plan offers plenty of flexibility for guests, a home office, hobbies, or multigenerational living. With multiple living spaces and room for everyone to have a place of their own, this is the kind of home that adapts to your life—not the other way around. Whether you’re hosting a full house for the holidays, working from home, welcoming extended family, or simply craving more breathing room, you’ll appreciate just how much possibility this home offers. And with a whole-house generator, you’ll have the added peace of mind of knowing your home is prepared when the unexpected happens. Located with convenient access to commuter routes, shopping, dining, and everyday necessities, this home offers the space you’ve been searching for in a location that keeps you connected. If you’ve been waiting for a home with room for today and flexibility for whatever comes next, this one deserves a closer look. Home Warranty offered to qualified buyer! Updates: Fresh Paint throughout (2022), Full Kitchen Reno (2022), New main level/basement heat pump (2023), Upgraded Water Softener/Filtration System (2025), Automatic Garage Door Opener (2025), All new Toilets (2025), HVAC Maintenance every 6 months

5 Beds ⋅ 5 Baths

This home is where space, comfort and flexibility come together in a home designed to grow with you. Tucked away on a quiet dead-end street, this spacious home offers room to spread out while still feeling warm and inviting. A sought-after main-level owner’s suite makes everyday living easy, while the generous floor plan offers plenty of flexibility for guests, a home office, hobbies, or multigenerational living. With multiple living spaces and room for everyone to have a place of their own, this is the kind of home that adapts to your life—not the other way around. Whether you’re hosting a full house for the holidays, working from home, welcoming extended family, or simply craving more breathing room, you’ll appreciate just how much possibility this home offers. And with a whole-house generator, you’ll have the added peace of mind of knowing your home is prepared when the unexpected happens. Located with convenient access to commuter routes, shopping, dining, and everyday necessities, this home offers the space you’ve been searching for in a location that keeps you connected. If you’ve been waiting for a home with room for today and flexibility for whatever comes next, this one deserves a closer look. Home Warranty offered to qualified buyer! Updates: Fresh Paint throughout (2022), Full Kitchen Reno (2022), New main level/basement heat pump (2023), Upgraded Water Softener/Filtration System (2025), Automatic Garage Door Opener (2025), All new Toilets (2025), HVAC Maintenance every 6 months

136 Cahille Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$1,350,000

Prime Medical Condo suite for Sale; located adjacent to the Winchester Medical Center. 6,200 Square Feet total with 4,580 square feet immediately available. 1,620 square feet is being leased, with another year on the lease. Building is in excellent condition, fully updated and easy to maintain. Prominent and highly visible location and ample parking. Few landlord responsibilities. Huge growth market! Priced at $1,350,000. Also available for lease.

142 Linden Dr Unit 106, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$339,000

Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath. 215 Clifford street is being renovated with new windows, front door, subfloor, paint, kitchen counters and cabinets. This one will be ready for its new owner. The properties are deeded separately as two parcels (tax #193-01-T-9 & 193-01-T-8) , providing added flexibility for future investment strategies. All occupied units are currently rented on month-to-month leases, offering the new owner maximum flexibility to adjust rents, renovate, or continue operating as investment properties. As of the listing date, one unit is vacant, presenting an immediate opportunity to place a new tenant at market rent or occupy the property. Prospective buyers are welcome to drive by and walk the exterior of the properties. Interior showings are by appointment only. Whether you're looking to expand your rental portfolio or invest in a property with immediate income potential and future upside, this is a rare opportunity within Winchester City limits.

211 213-215 E Clifford St, Winchester

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

$399,000

Luxury upgrades and thoughtful custom features make this exceptional end-unit townhome a standout in the desirable Winchester Landing 55+ community. With over $80,000 in owner-added upgrades, this beautifully appointed residence offers 3 bedrooms, 2.5 baths, and the convenience of main-level living with premium finishes throughout. The spacious main-level primary suite provides a private retreat, featuring a luxurious bath with a walk-in shower, dual vanities, and a walk-in closet enhanced with custom-built organization systems. At the heart of the home, the gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, a large center island, gas cooking, and abundant workspace. The open-concept floor plan flows seamlessly into the dining and living areas, creating an inviting atmosphere for gathering with family and friends. Step outside to a backyard transformed into a private outdoor oasis. The screened porch overlooks professionally installed turf, vinyl fencing, landscape lighting, and a custom fire pit area, creating the perfect setting for relaxing or entertaining while enjoying a truly low-maintenance lifestyle. Modern smart-home technology has been thoughtfully integrated throughout the home, adding convenience, efficiency, and peace of mind. The attached garage is equally impressive, featuring epoxy-coated floors and wall protection systems that create a clean, polished, and highly functional space rarely found in townhome living. Meticulously maintained and move-in ready, this home offers one of the finest opportunities in Winchester Landing. Combining a premium end-unit location, sophisticated finishes, and more than $80,000 in upgrades, this is luxury low-maintenance living at its best. Schedule your private showing today.

3 Beds ⋅ 3 Baths

Luxury upgrades and thoughtful custom features make this exceptional end-unit townhome a standout in the desirable Winchester Landing 55+ community. With over $80,000 in owner-added upgrades, this beautifully appointed residence offers 3 bedrooms, 2.5 baths, and the convenience of main-level living with premium finishes throughout. The spacious main-level primary suite provides a private retreat, featuring a luxurious bath with a walk-in shower, dual vanities, and a walk-in closet enhanced with custom-built organization systems. At the heart of the home, the gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, a large center island, gas cooking, and abundant workspace. The open-concept floor plan flows seamlessly into the dining and living areas, creating an inviting atmosphere for gathering with family and friends. Step outside to a backyard transformed into a private outdoor oasis. The screened porch overlooks professionally installed turf, vinyl fencing, landscape lighting, and a custom fire pit area, creating the perfect setting for relaxing or entertaining while enjoying a truly low-maintenance lifestyle. Modern smart-home technology has been thoughtfully integrated throughout the home, adding convenience, efficiency, and peace of mind. The attached garage is equally impressive, featuring epoxy-coated floors and wall protection systems that create a clean, polished, and highly functional space rarely found in townhome living. Meticulously maintained and move-in ready, this home offers one of the finest opportunities in Winchester Landing. Combining a premium end-unit location, sophisticated finishes, and more than $80,000 in upgrades, this is luxury low-maintenance living at its best. Schedule your private showing today.

113 Wertland Pl, Winchester

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

$289,000

NOT YOUR AVERAGE CONDO! If you’ve been waiting for something truly MOVE-IN READY, this beautifully renovated penthouse-level condo is the one you need to see! Completely renovated down to the studs, this 2-bedroom, 2-full-bath home has been thoughtfully redesigned with style, comfort, and quality in mind. From the moment you walk through the door, you’ll notice the difference—updated flooring, custom molding, neutral finishes, recessed lighting, and attention to detail throughout. The gorgeous kitchen features granite countertops, upgraded soft-close cabinetry, stainless steel appliances, and a clean, modern design that flows beautifully into the living space. A custom stone gas fireplace creates an impressive focal point and adds warmth and character you simply don’t expect to find at this price point. Both bedrooms offer great space, while two FULL bathrooms make the floor plan exceptionally functional. The updated baths continue the upscale feel, including a beautiful walk-in shower and stylish finishes. And here’s the best part—ALL THE WORK HAS ALREADY BEEN DONE! No outdated kitchen to replace. No flooring project waiting for you. No list of renovations to tackle after closing. Just move in, unpack, and enjoy! Located on the penthouse level with approximately 1,173 square feet, this home delivers the polished look and feel of a much more expensive property while offering the convenience of low-maintenance condo living. If you’ve been scrolling through condos that all seem to look the same, STOP SCROLLING. 110 Brookland Court #10 is different—and you’ll see it the minute you walk through the door.

2 Beds ⋅ 2 Baths

NOT YOUR AVERAGE CONDO! If you’ve been waiting for something truly MOVE-IN READY, this beautifully renovated penthouse-level condo is the one you need to see! Completely renovated down to the studs, this 2-bedroom, 2-full-bath home has been thoughtfully redesigned with style, comfort, and quality in mind. From the moment you walk through the door, you’ll notice the difference—updated flooring, custom molding, neutral finishes, recessed lighting, and attention to detail throughout. The gorgeous kitchen features granite countertops, upgraded soft-close cabinetry, stainless steel appliances, and a clean, modern design that flows beautifully into the living space. A custom stone gas fireplace creates an impressive focal point and adds warmth and character you simply don’t expect to find at this price point. Both bedrooms offer great space, while two FULL bathrooms make the floor plan exceptionally functional. The updated baths continue the upscale feel, including a beautiful walk-in shower and stylish finishes. And here’s the best part—ALL THE WORK HAS ALREADY BEEN DONE! No outdated kitchen to replace. No flooring project waiting for you. No list of renovations to tackle after closing. Just move in, unpack, and enjoy! Located on the penthouse level with approximately 1,173 square feet, this home delivers the polished look and feel of a much more expensive property while offering the convenience of low-maintenance condo living. If you’ve been scrolling through condos that all seem to look the same, STOP SCROLLING. 110 Brookland Court #10 is different—and you’ll see it the minute you walk through the door.

110 Brookland Court Unit 10, Winchester

Listing courtesy of Samson Properties. Contact:

$550,000

Modern craftsman home in one of Winchester’s newer communities. Easy access to RT 50 and I81, Shenandoah University, Jim Barnett Park, shopping, and restaurants. Old Town Winchester three miles away. This ranch home offers an open-floor concept with custom living upgrades. Dining room includes a coffee station/wet bar with a refrigerator and the living room has an electric fireplace with a great entertainment flow that carries onto the covered deck with stairs to the fenced-in backyard for added family fun. Finished garage with heating and cooling, recessed lighting, utility sink, and epoxy flooring makes for a great gym or multipurpose space. Master bedroom ensuite includes a bedroom-sized walk-in closet and added storage area. For an expanded living area, the full unfinished walkout basement with a full-size window and bathroom rough-in await your creative design. Other Upgrades include: Whole house water filtration system and water softener. Reverse osmosis faucet in the wet bar. LVP throughout the entire home. Adjustable Elfa-shelving in all of the closets. Smart home features allow you to control security features, garage, and thermostat from an app, including ADT alarm system and auto-lock doors; Ring cameras and doorbell; NEST thermostat; and MyQ garage door opener. Community amenities include a pool with pool house, a multipurpose court (basketball/ pickleball), two playgrounds, and a short trail.

3 Beds ⋅ 3 Baths

Modern craftsman home in one of Winchester’s newer communities. Easy access to RT 50 and I81, Shenandoah University, Jim Barnett Park, shopping, and restaurants. Old Town Winchester three miles away. This ranch home offers an open-floor concept with custom living upgrades. Dining room includes a coffee station/wet bar with a refrigerator and the living room has an electric fireplace with a great entertainment flow that carries onto the covered deck with stairs to the fenced-in backyard for added family fun. Finished garage with heating and cooling, recessed lighting, utility sink, and epoxy flooring makes for a great gym or multipurpose space. Master bedroom ensuite includes a bedroom-sized walk-in closet and added storage area. For an expanded living area, the full unfinished walkout basement with a full-size window and bathroom rough-in await your creative design. Other Upgrades include: Whole house water filtration system and water softener. Reverse osmosis faucet in the wet bar. LVP throughout the entire home. Adjustable Elfa-shelving in all of the closets. Smart home features allow you to control security features, garage, and thermostat from an app, including ADT alarm system and auto-lock doors; Ring cameras and doorbell; NEST thermostat; and MyQ garage door opener. Community amenities include a pool with pool house, a multipurpose court (basketball/ pickleball), two playgrounds, and a short trail.

140 Poe Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$549,990

The Hayden is a spacious two-story home offering 6 bedrooms, 4 bathrooms, and over 3,100 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. The main level features a versatile flex room off the foyer, ideal for a formal dining room, home office, or additional living space. The gourmet kitchen includes an oversized island with seating, a large pantry, and opens seamlessly to the dining area and expansive living room. A main-level bedroom with a full bathroom provides an ideal setup for guests or multi-generational living. Upstairs, the owner’s suite serves as a private retreat with a luxurious bath featuring a standing shower, private water closet, double vanity, and a spacious walk-in closet. The upper level also includes three additional bedrooms, a full bathroom, a walk-in laundry room, and a loft area for added flexibility. The finished walkout basement expands the home even further, offering an additional bedroom and full bathroom—perfect for guests, recreation, or private living quarters. Situated on a homesite backing to mature trees, this home provides added privacy and a peaceful setting. Quality craftsmanship and attention to detail shine throughout, along with a one-year builder’s warranty. Move - in ready! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

6 Beds ⋅ 4 Baths

The Hayden is a spacious two-story home offering 6 bedrooms, 4 bathrooms, and over 3,100 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. The main level features a versatile flex room off the foyer, ideal for a formal dining room, home office, or additional living space. The gourmet kitchen includes an oversized island with seating, a large pantry, and opens seamlessly to the dining area and expansive living room. A main-level bedroom with a full bathroom provides an ideal setup for guests or multi-generational living. Upstairs, the owner’s suite serves as a private retreat with a luxurious bath featuring a standing shower, private water closet, double vanity, and a spacious walk-in closet. The upper level also includes three additional bedrooms, a full bathroom, a walk-in laundry room, and a loft area for added flexibility. The finished walkout basement expands the home even further, offering an additional bedroom and full bathroom—perfect for guests, recreation, or private living quarters. Situated on a homesite backing to mature trees, this home provides added privacy and a peaceful setting. Quality craftsmanship and attention to detail shine throughout, along with a one-year builder’s warranty. Move - in ready! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

133 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

$899,000

Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

3 Beds ⋅ 4 Baths

Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

466 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

$784,900

This beautiful, well-cared-for home occupies a peaceful setting overlooking a lake and stream directly behind the house. The well-stocked lake has an easily accessible walking trail near the back of the house. The owners have painted the entire interior and added new lighting fixtures, blinds, and window treatments, all of which convey. The main-floor half bath has new wallpaper, a new vanity & tile floor. The newly modernized fireplace has tile & mantle & is wired for TV. The TVs convey. New washer and dryer in the laundry room and new shelving in the laundry closet. New hot water heater. The kitchen is a dream, including a double oven, a large cooktop, and an oversized island. The morning room overlooking the lake has beautiful sunrise views. A new refrigerator and microwave have been installed in the kitchen, along with a new pantry door and shelving. The lower living area bathroom has a new vanity and mirror. With the exception of furniture in the living room and a large table, all the remaining furniture comes with the house, including the bedrooms. This is nearly a "turnkey" value; just pack your clothes and move in. The furniture that is staying in the house was purchased in the last three years. Upstairs, there are four nice bedrooms and three full baths. One of the secondary bedrooms has an en suite that is perfect for in-laws or older children. Outside, the lower-level patio area features new landscaping and swings for enjoying the view. The deck has a new railing. The front yard shrubbery was also enhanced.

5 Beds ⋅ 5 Baths

This beautiful, well-cared-for home occupies a peaceful setting overlooking a lake and stream directly behind the house. The well-stocked lake has an easily accessible walking trail near the back of the house. The owners have painted the entire interior and added new lighting fixtures, blinds, and window treatments, all of which convey. The main-floor half bath has new wallpaper, a new vanity & tile floor. The newly modernized fireplace has tile & mantle & is wired for TV. The TVs convey. New washer and dryer in the laundry room and new shelving in the laundry closet. New hot water heater. The kitchen is a dream, including a double oven, a large cooktop, and an oversized island. The morning room overlooking the lake has beautiful sunrise views. A new refrigerator and microwave have been installed in the kitchen, along with a new pantry door and shelving. The lower living area bathroom has a new vanity and mirror. With the exception of furniture in the living room and a large table, all the remaining furniture comes with the house, including the bedrooms. This is nearly a "turnkey" value; just pack your clothes and move in. The furniture that is staying in the house was purchased in the last three years. Upstairs, there are four nice bedrooms and three full baths. One of the secondary bedrooms has an en suite that is perfect for in-laws or older children. Outside, the lower-level patio area features new landscaping and swings for enjoying the view. The deck has a new railing. The front yard shrubbery was also enhanced.

118 Aulee Ct, Winchester

Listing courtesy of George W. Glaize, Jr., Inc. REALTOR. Contact:

$590,000

Pictures coming soon. Prime Location in Raven Wing! This beautiful Colonial home offers the perfect combination of comfort, convenience, and modern updates. Located in the desirable Raven Wing community, you'll enjoy easy access to schools, shopping, restaurants, and commuter routes. Recent improvements include a new roof (2025), hot water heater (3 years old), sump pump (1.5 years old), and new dishwasher and stove, providing peace of mind for years to come. Inside, the home features 4 bedrooms and 3.5 bathrooms with an open floor plan designed for both everyday living and entertaining. The spacious family room includes a cozy gas fireplace, while the kitchen boasts upgraded cabinetry, granite countertops, and a bright breakfast area. Additional main-level features include formal dining and living rooms (or a home office), hardwood flooring, and ceramic tile flooring in all bathrooms. The spacious primary suite offers a large walk-in closet and a luxurious private bath. The fully finished basement provides a large recreation room, full bathroom, and abundant storage space. Enjoy outdoor living from the covered front and rear porches overlooking the large, fully fenced backyard, complete with a spacious patio and storage shed. High-speed internet is available. All measurements are approximate.

4 Beds ⋅ 4 Baths

Pictures coming soon. Prime Location in Raven Wing! This beautiful Colonial home offers the perfect combination of comfort, convenience, and modern updates. Located in the desirable Raven Wing community, you'll enjoy easy access to schools, shopping, restaurants, and commuter routes. Recent improvements include a new roof (2025), hot water heater (3 years old), sump pump (1.5 years old), and new dishwasher and stove, providing peace of mind for years to come. Inside, the home features 4 bedrooms and 3.5 bathrooms with an open floor plan designed for both everyday living and entertaining. The spacious family room includes a cozy gas fireplace, while the kitchen boasts upgraded cabinetry, granite countertops, and a bright breakfast area. Additional main-level features include formal dining and living rooms (or a home office), hardwood flooring, and ceramic tile flooring in all bathrooms. The spacious primary suite offers a large walk-in closet and a luxurious private bath. The fully finished basement provides a large recreation room, full bathroom, and abundant storage space. Enjoy outdoor living from the covered front and rear porches overlooking the large, fully fenced backyard, complete with a spacious patio and storage shed. High-speed internet is available. All measurements are approximate.

211 Flanagan Dr, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$675,000

MOTIVATED SELLERS!!! Sellers are offering $10,000 in closing costs with the right offer, to be used towards closing costs, points, etc. * Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home with ample space and lots of room for your dreams, then this is the home for you! Located on a quiet Cul-de-Sac, this beautiful brick home welcomes you with an impressive foyer and high ceilings. The first floor of this home houses a lovely kitchen with an ample great room, combination formal living/dining and a beautiful office/flex space with french doors. On the second floor you will find not one, but two en suite bedrooms, both quite sizeable, as are all the rooms in this lovely home. The primary suite hosts a large living space that was optioned when built, but set up to easily create an additional bedroom, if needed. The primary suite bathroom is a true sanctuary, bright, white and welcoming for your daily routine. With ample closet space, bright rooms and an additional bathroom to the two en suite bathrooms, the second floor is quite impressive. More space? OK! The basement has been completely finished with an additional full bathroom and flex room, bright recessed lighting and spacious with with walkout stairs. This home has been maintained beautifully and has a number of upgrades including, but not limited to, a full powder room remodel (2026), full basement finishing and bathroom (2025), laundry room remodel (2025), new decking (2025)... and more! With ample space for anything you can dream, whether hobbies or crafts, or entertaining friends and family, to game rooms and beyond, Norfolk Ct is waiting for you. Ideally located to commuter roads and a quick jaunt to downtown Winchester, the location is simply a bonus to all this beautiful home has to offer.

4 Beds ⋅ 5 Baths

MOTIVATED SELLERS!!! Sellers are offering $10,000 in closing costs with the right offer, to be used towards closing costs, points, etc. * Welcome home to Norfolk Ct!!! Oh my, where to begin? If you're looking for a turnkey home with ample space and lots of room for your dreams, then this is the home for you! Located on a quiet Cul-de-Sac, this beautiful brick home welcomes you with an impressive foyer and high ceilings. The first floor of this home houses a lovely kitchen with an ample great room, combination formal living/dining and a beautiful office/flex space with french doors. On the second floor you will find not one, but two en suite bedrooms, both quite sizeable, as are all the rooms in this lovely home. The primary suite hosts a large living space that was optioned when built, but set up to easily create an additional bedroom, if needed. The primary suite bathroom is a true sanctuary, bright, white and welcoming for your daily routine. With ample closet space, bright rooms and an additional bathroom to the two en suite bathrooms, the second floor is quite impressive. More space? OK! The basement has been completely finished with an additional full bathroom and flex room, bright recessed lighting and spacious with with walkout stairs. This home has been maintained beautifully and has a number of upgrades including, but not limited to, a full powder room remodel (2026), full basement finishing and bathroom (2025), laundry room remodel (2025), new decking (2025)... and more! With ample space for anything you can dream, whether hobbies or crafts, or entertaining friends and family, to game rooms and beyond, Norfolk Ct is waiting for you. Ideally located to commuter roads and a quick jaunt to downtown Winchester, the location is simply a bonus to all this beautiful home has to offer.

108 Norfolk Ct, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$4,000

.31 acre wooded lot on an incline. No septic or well tests have been done. Seller doesn't know if it's buildable. Drive by any time to show.

Fox Trl Unit LOT 1, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$6,000

Discover the perfect blend of privacy and nature with this beautiful wooded lot located on Panther Drive in the desirable Wilde Acres community. Offering approximately 0.252 acres, this property provides an excellent opportunity to build your dream home, vacation getaway, or weekend retreat surrounded by the peaceful beauty of the surrounding forest. Mature trees create a picturesque setting while providing natural privacy and a tranquil atmosphere. With road frontage already in place, accessing your future homesite is both convenient and practical. Whether you're looking to enjoy the sights and sounds of nature, create a relaxing escape from the hustle and bustle, or invest in land for the future, this property offers endless possibilities. Wilde Acres continues to attract those seeking a peaceful mountain lifestyle while remaining within approximately 20 to 25 minutes of downtown Winchester. Enjoy easy access to shopping, dining, healthcare through Valley Health, educational opportunities at Shenandoah University and Laurel Ridge Community College, major employers such as Amazon, and countless recreational amenities. Don't miss this opportunity to bring your vision to life in one of the area's most scenic and growing communities. Your future starts here on Panther Drive.

705 Panther Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$899,900

Exceptional All-Brick Custom Home with Panoramic Mountain Views! Nestled on a private 2-acre cul-de-sac lot in prestigious Butler Estates, this exceptional all-brick 4-bedroom, 4.5-bath custom home offers over three finished levels, timeless craftsmanship, and breathtaking Appalachian Mountain and pastoral views. A brand-new roof adds even more peace of mind. The main level features beautiful hardwood floors and an easy flow between the gourmet kitchen and spacious family room. The kitchen offers granite countertops, center island, propane cooktop, and reverse osmosis water filtration. The family room includes custom built-ins and a fireplace. A versatile front room can serve as a library, sitting area, playroom, second office, or additional entertaining space, while a dedicated home office provides a private workspace. Upstairs, the spacious primary suite features two walk-in closets, a private balcony with stunning views, and a spa-inspired bath with double vanities, jetted tub, and tiled walk-in shower. Three additional bedrooms include a private ensuite and Jack-and-Jill bath. The finished walkout lower level is perfect for entertaining with a recreation room, gas fireplace, media room, built-ins, wet bar, and electric fireplace. An exercise room, flexible fifth-bedroom space, and full bath complete the level. Media equipment and television convey. Enjoy outdoor living on the TimberTech deck and two brick patios surrounded by professionally landscaped grounds, invisible fencing, and spectacular views. Just 10 minutes from Winchester Medical Center and minutes from Route 37 and Interstate 81, this rare all-brick Butler Estates home offers privacy, incredible views, exceptional living space, and the convenience today's buyers are looking for.

4 Beds ⋅ 5 Baths

Exceptional All-Brick Custom Home with Panoramic Mountain Views! Nestled on a private 2-acre cul-de-sac lot in prestigious Butler Estates, this exceptional all-brick 4-bedroom, 4.5-bath custom home offers over three finished levels, timeless craftsmanship, and breathtaking Appalachian Mountain and pastoral views. A brand-new roof adds even more peace of mind. The main level features beautiful hardwood floors and an easy flow between the gourmet kitchen and spacious family room. The kitchen offers granite countertops, center island, propane cooktop, and reverse osmosis water filtration. The family room includes custom built-ins and a fireplace. A versatile front room can serve as a library, sitting area, playroom, second office, or additional entertaining space, while a dedicated home office provides a private workspace. Upstairs, the spacious primary suite features two walk-in closets, a private balcony with stunning views, and a spa-inspired bath with double vanities, jetted tub, and tiled walk-in shower. Three additional bedrooms include a private ensuite and Jack-and-Jill bath. The finished walkout lower level is perfect for entertaining with a recreation room, gas fireplace, media room, built-ins, wet bar, and electric fireplace. An exercise room, flexible fifth-bedroom space, and full bath complete the level. Media equipment and television convey. Enjoy outdoor living on the TimberTech deck and two brick patios surrounded by professionally landscaped grounds, invisible fencing, and spectacular views. Just 10 minutes from Winchester Medical Center and minutes from Route 37 and Interstate 81, this rare all-brick Butler Estates home offers privacy, incredible views, exceptional living space, and the convenience today's buyers are looking for.

144 Widener Dr, Winchester

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

$320,000

Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout. Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private second-floor balcony and a shared first-level patio, perfect for relaxing or gathering with friends and family. Whether you're searching for a primary residence, an owner-occupied investment, or a property with income potential, this home offers exceptional flexibility in a highly desirable location. Ideally situated in the heart of Winchester, you'll be just minutes from the popular Old Town Winchester Walking Mall, with convenient access to shopping, dining, entertainment, and local attractions. Don't miss this opportunity to own a distinctive property in one of Winchester's most sought-after locations

4 Beds ⋅ 2 Baths

Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout. Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private second-floor balcony and a shared first-level patio, perfect for relaxing or gathering with friends and family. Whether you're searching for a primary residence, an owner-occupied investment, or a property with income potential, this home offers exceptional flexibility in a highly desirable location. Ideally situated in the heart of Winchester, you'll be just minutes from the popular Old Town Winchester Walking Mall, with convenient access to shopping, dining, entertainment, and local attractions. Don't miss this opportunity to own a distinctive property in one of Winchester's most sought-after locations

410 S Cameron St, Winchester

Listing courtesy of Samson Properties. Contact:

$499,900

Welcome to 110 Russellcroft Road, a beautifully updated 4-bedroom, 3-full-bath ranch-style home in the established Cedarmeade community of Winchester, VA. Offering approximately 3,000 square feet of finished living space including the finished lower level, this home combines comfortable everyday living with the flexibility today's buyers are looking for. The main level features warm hardwood floors, abundant natural light, and an inviting layout centered around an updated kitchen with a large island, pantry, recessed lighting, and easy access to the dining area. Two brick fireplaces add timeless character and create welcoming spaces for gathering, relaxing, or entertaining. The finished lower level is where this home truly stands out, providing an expansive recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Use the additional space as a family room, home office, gym, media room, guest area, game room, or entertaining space—the possibilities are endless. Outside, the nearly half-acre lot provides plenty of room to enjoy the outdoors, with a spacious backyard, mature surroundings, and a welcoming front porch. The attached 2-car garage provides additional convenience and storage. Located in Cedarmeade within Winchester City, this home offers convenient access to schools, parks, shopping, dining, major commuter routes, and all that downtown Winchester has to offer. If you're searching for an updated Winchester, VA ranch home with 4 bedrooms, 3 full baths, a finished basement, substantial living space, and a generous lot, 110 Russellcroft Road deserves a look.

4 Beds ⋅ 3 Baths

Welcome to 110 Russellcroft Road, a beautifully updated 4-bedroom, 3-full-bath ranch-style home in the established Cedarmeade community of Winchester, VA. Offering approximately 3,000 square feet of finished living space including the finished lower level, this home combines comfortable everyday living with the flexibility today's buyers are looking for. The main level features warm hardwood floors, abundant natural light, and an inviting layout centered around an updated kitchen with a large island, pantry, recessed lighting, and easy access to the dining area. Two brick fireplaces add timeless character and create welcoming spaces for gathering, relaxing, or entertaining. The finished lower level is where this home truly stands out, providing an expansive recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Use the additional space as a family room, home office, gym, media room, guest area, game room, or entertaining space—the possibilities are endless. Outside, the nearly half-acre lot provides plenty of room to enjoy the outdoors, with a spacious backyard, mature surroundings, and a welcoming front porch. The attached 2-car garage provides additional convenience and storage. Located in Cedarmeade within Winchester City, this home offers convenient access to schools, parks, shopping, dining, major commuter routes, and all that downtown Winchester has to offer. If you're searching for an updated Winchester, VA ranch home with 4 bedrooms, 3 full baths, a finished basement, substantial living space, and a generous lot, 110 Russellcroft Road deserves a look.

110 Russellcroft Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$110,000

The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.42 lot C is wooded, has septic already installed, has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet and tranquility, and/or the new concept of a tiny home! Driveway is a little washed out so recommend 4 wheel drive or walk up from Pack Horse Road.

Pack Horse Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$89,000

The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 5 acre lot B is wooded, has an old cabin (do not enter and at one time had electric), has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet and tranquility, and/or the new concept of a tiny home! Driveway is a little washed out so recommend 4 wheel drive or walk up from Pack Horse Road.

Pack Horse Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

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