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Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting gorgeous original hardwood floors, a convenient main-level half bath, a spacious formal dining room, and a warm living room anchored by a cozy wood-burning fireplace. The efficient kitchen offers a brand-new stove, plenty of storage and prep space, and a dedicated pantry for ultimate organization. The entire home has been freshly painted inside, with brand-new carpet installed across the stairs and bedrooms—including the large primary bedroom upstairs. Head downstairs to find a full, finished basement that provides additional living space, an abundance of extra storage, and a dedicated laundry area. Major mechanical updates offer complete peace of mind, including an all-brick exterior, a newer roof, newer HVAC, and newer windows throughout. Step outside to your private oasis—an extensive patio framed by beautiful mature trees that backs directly to the scenic Park Place Park, offering an extended backyard feel and peaceful views with no rear neighbors. Complete with a large storage shed to easily house all of your tools, lawn equipment, or outdoor gear. Conveniently located near shopping, dining, walking trails, and major commuter routes. Come see this home and schedule your private tour today!

812 Appleseed Ct, Winchester

Listing courtesy of Realty FC. Contact:

$339,900

Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

1847 Melvor Ln, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$375,000

265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

265 Mcdonald Rd, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact:

$317,265

Seller Credit of $3000! Use it for a buydown to lower your payment!! See Flyer in docs NEW PHOTOS! Landscaping done! Professional cleaning done! New Flooring in bedrooms! Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. A brand new roof and pressure tank! The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

Seller Credit of $3000! Use it for a buydown to lower your payment!! See Flyer in docs NEW PHOTOS! Landscaping done! Professional cleaning done! New Flooring in bedrooms! Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. A brand new roof and pressure tank! The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

148 Doe Trl, Winchester

Listing courtesy of Keller Williams Realty Advantage. Contact:

$289,900

Spacious three-level townhome in a desirable Winchester community, conveniently located near Sunnyside and Old Town Winchester! Offering generously sized bedrooms, three and a half baths, and flexible living space across three levels, this home has room for everyone. The main level features a comfortable family room, dining area, kitchen, and convenient powder room, with access to the spacious rear deck overlooking mature trees and HOA owned property. The private wooded setting creates a peaceful outdoor oasis, perfect for relaxing, grilling, or entertaining. Upstairs, you'll find two spacious bedrooms, each with its own full bath, providing excellent privacy and comfort. The finished basement adds even more versatility with a large recreation room, additional bonus/bedroom space, and a full bathroom. Whether used for guests, a home office, hobbies, or recreation, the lower level offers valuable additional living space. Enjoy the best of both convenience and tranquility, with a private, tree-lined setting while being just minutes from Sunnyside, Old Town Winchester, shopping, dining, parks, and commuter routes. A wonderful opportunity to enjoy spacious townhome living in a great location with flexible space and a private backyard setting.

Spacious three-level townhome in a desirable Winchester community, conveniently located near Sunnyside and Old Town Winchester! Offering generously sized bedrooms, three and a half baths, and flexible living space across three levels, this home has room for everyone. The main level features a comfortable family room, dining area, kitchen, and convenient powder room, with access to the spacious rear deck overlooking mature trees and HOA owned property. The private wooded setting creates a peaceful outdoor oasis, perfect for relaxing, grilling, or entertaining. Upstairs, you'll find two spacious bedrooms, each with its own full bath, providing excellent privacy and comfort. The finished basement adds even more versatility with a large recreation room, additional bonus/bedroom space, and a full bathroom. Whether used for guests, a home office, hobbies, or recreation, the lower level offers valuable additional living space. Enjoy the best of both convenience and tranquility, with a private, tree-lined setting while being just minutes from Sunnyside, Old Town Winchester, shopping, dining, parks, and commuter routes. A wonderful opportunity to enjoy spacious townhome living in a great location with flexible space and a private backyard setting.

114 Tudor Dr, Winchester

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

$364,900

"Come On Down To Cidermill" Beautiful 3 bedroom, 2 1/2 bath duplex style townhome at end of street! All 3 bedrooms on upper level. Spacious family room, large eat in kitchen and back deck with stairs down to the yard. Large laundry room on basement level. One car garage and spacious driveway. Conveniently located in Winchester City. Home has just been remolded with the following: All new LVP flooring throughout, freshly painted on the inside, front door painted, garage door painted, shutters painted, handrail out front painted, deck remodeled, fresh mulch, bushes trimmed, new stainless-steel appliances and a new HVAC system! Hurry this one won't last long!

"Come On Down To Cidermill" Beautiful 3 bedroom, 2 1/2 bath duplex style townhome at end of street! All 3 bedrooms on upper level. Spacious family room, large eat in kitchen and back deck with stairs down to the yard. Large laundry room on basement level. One car garage and spacious driveway. Conveniently located in Winchester City. Home has just been remolded with the following: All new LVP flooring throughout, freshly painted on the inside, front door painted, garage door painted, shutters painted, handrail out front painted, deck remodeled, fresh mulch, bushes trimmed, new stainless-steel appliances and a new HVAC system! Hurry this one won't last long!

1957 Cidermill Ln, Winchester

Listing courtesy of Samson Properties. Contact:

$277,000

Nestled in the charming Copperfield neighborhood, this delightful townhouse offers a perfect blend of comfort and convenience. Built in 2002, this well-maintained home features 2 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and everyday living. With 1,868 square feet of thoughtfully designed interiors, you'll find a cozy atmosphere that invites you to unwind. The inviting layout includes a versatile basement, perfect for a home office, gym, or additional storage. The exterior boasts classic vinyl siding, enhancing the home's curb appeal while ensuring durability. Enjoy the ease of parking with two dedicated spaces in the nearby lot, making coming home a breeze. Copperfield is more than just a location; it's a vibrant community. Residents appreciate the nearby trails and parks, perfect for leisurely strolls or weekend picnics. Local shops and dining options are just a short drive away, offering a variety of choices to satisfy every palate. The neighborhood is known for its friendly atmosphere, making it easy to connect with neighbors and enjoy community events. This townhouse is not just a place to live; it's a place to thrive. Experience the warmth of Copperfield and make this charming residence your new home. Don't miss the opportunity to embrace a lifestyle filled with comfort and convenience in this inviting community!

2 Beds ⋅ 3 Baths

Nestled in the charming Copperfield neighborhood, this delightful townhouse offers a perfect blend of comfort and convenience. Built in 2002, this well-maintained home features 2 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and everyday living. With 1,868 square feet of thoughtfully designed interiors, you'll find a cozy atmosphere that invites you to unwind. The inviting layout includes a versatile basement, perfect for a home office, gym, or additional storage. The exterior boasts classic vinyl siding, enhancing the home's curb appeal while ensuring durability. Enjoy the ease of parking with two dedicated spaces in the nearby lot, making coming home a breeze. Copperfield is more than just a location; it's a vibrant community. Residents appreciate the nearby trails and parks, perfect for leisurely strolls or weekend picnics. Local shops and dining options are just a short drive away, offering a variety of choices to satisfy every palate. The neighborhood is known for its friendly atmosphere, making it easy to connect with neighbors and enjoy community events. This townhouse is not just a place to live; it's a place to thrive. Experience the warmth of Copperfield and make this charming residence your new home. Don't miss the opportunity to embrace a lifestyle filled with comfort and convenience in this inviting community!

323 Copperfield Ln, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$300,000

Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own. The main-level living design provides easy access throughout the home, making this property a great fit for first-time buyers, downsizers, or anyone looking for a manageable home without stairs. The level lot offers space for outdoor enjoyment, gardening, entertaining, or future improvements. With three bedrooms, a full bath, and a manageable footprint, this home offers an excellent opportunity for a buyer looking for affordability and convenience. Bring your vision and add your personal touches to create the home you've been looking for.

3 Beds ⋅ 1 Baths

Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own. The main-level living design provides easy access throughout the home, making this property a great fit for first-time buyers, downsizers, or anyone looking for a manageable home without stairs. The level lot offers space for outdoor enjoyment, gardening, entertaining, or future improvements. With three bedrooms, a full bath, and a manageable footprint, this home offers an excellent opportunity for a buyer looking for affordability and convenience. Bring your vision and add your personal touches to create the home you've been looking for.

111 Haven Ter, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

$335,000

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!

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:

$169,900

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:

$295,000

**Investor & Fixer-Upper Special Endless Potential on Nearly 1 Acre!** Calling all visionaries, weekend warriors, and Airbnb hosts! This secluded retreat in Shawneeland is your chance to create the mountain getaway, rental, or private homestead you've been dreaming of customized entirely to your style. Offering an estimated 2,000+ sq ft of finished living space with the potential for over 2,400 total sq ft, this home has great bones to build on: new foundation repairs, porch, roof, HVAC, and well pump/bladder (all 2012), hot water heater (2019), and washer/dryer (2016). The spacious porch was even framed with a hot tub in mind just add your finishing touches! A walk-out basement leads to an oversized attached 2-car garage, offering great flexibility for storage, a workshop, or extra living space. Set on a corner lot that was once two separate parcels and is now combined into just shy of 1 acre, this is one of the largest lots you'll find in Shawneeland with room to roam and privacy to spare. And despite the tranquil, wooded setting, you're only about 15 miles from historic, charming downtown Winchester, a destination growing fast in popularity. Bring your tools, your creativity, and your vision, this one is priced for opportunity and sold strictly As Is. No HOA Home is eligable for a FHA 203K loan. Contact agent for details.

2 Beds ⋅ 3 Baths

**Investor & Fixer-Upper Special Endless Potential on Nearly 1 Acre!** Calling all visionaries, weekend warriors, and Airbnb hosts! This secluded retreat in Shawneeland is your chance to create the mountain getaway, rental, or private homestead you've been dreaming of customized entirely to your style. Offering an estimated 2,000+ sq ft of finished living space with the potential for over 2,400 total sq ft, this home has great bones to build on: new foundation repairs, porch, roof, HVAC, and well pump/bladder (all 2012), hot water heater (2019), and washer/dryer (2016). The spacious porch was even framed with a hot tub in mind just add your finishing touches! A walk-out basement leads to an oversized attached 2-car garage, offering great flexibility for storage, a workshop, or extra living space. Set on a corner lot that was once two separate parcels and is now combined into just shy of 1 acre, this is one of the largest lots you'll find in Shawneeland with room to roam and privacy to spare. And despite the tranquil, wooded setting, you're only about 15 miles from historic, charming downtown Winchester, a destination growing fast in popularity. Bring your tools, your creativity, and your vision, this one is priced for opportunity and sold strictly As Is. No HOA Home is eligable for a FHA 203K loan. Contact agent for details.

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:

$385,000

Coming soon in Winchester! Welcome to this beautifully maintained 3-bedroom, 2-bath brick rambler in a convenient location. This move-in-ready home offers comfortable one-level living and features an updated kitchen with quartz countertops and stainless steel appliances, updated bathrooms, attractive flooring throughout, and a detached side-entry garage. The current owner has carefully maintained the property, making it ready for its next owner to enjoy. Conveniently located near shopping, dining, commuter routes, and everyday amenities. Professional photos and showing availability coming soon!

Coming soon in Winchester! Welcome to this beautifully maintained 3-bedroom, 2-bath brick rambler in a convenient location. This move-in-ready home offers comfortable one-level living and features an updated kitchen with quartz countertops and stainless steel appliances, updated bathrooms, attractive flooring throughout, and a detached side-entry garage. The current owner has carefully maintained the property, making it ready for its next owner to enjoy. Conveniently located near shopping, dining, commuter routes, and everyday amenities. Professional photos and showing availability coming soon!

108 Williamson Rd, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact:

$334,000

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!

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:

$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!

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:

$349,900

Major Price Reduction $30k Bring all Offers. Motivated Seller. Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

Major Price Reduction $30k Bring all Offers. Motivated Seller. Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless steel appliances, including a refrigerator, dishwasher, microwave, and stove, making meal prep a delight. A generous size family room just off the kitchen. Enjoy the convenience of main-floor laundry and a partially finished basement, perfect for a cozy retreat on gameday, or even possible 3rd bedroom, & couple extra rooms for storage. The attic could also add potential living space.(possible 4th) The inviting outdoor space is ideal for relaxation, Brand New Garage while the driveway provides ample off-street parking. Nestled in a vibrant community, residents benefit from nearby parks, excellent schools, Shenandoah University and convenient public services. Experience the warmth of neighborhood gatherings and the charm of local shops. This home is not just a place to live; it's a place to thrive. Embrace the lifestyle you've been dreaming of!

1414 S Braddock St, Winchester

Listing courtesy of Long & Foster Real Estate, 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:

$335,000

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!

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:

$354,900

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.

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:

$364,999

Welcome to this bright and inviting end-unit townhome in Winchester! Additional windows fill the home with natural light, while the open layout creates an easy flow between the kitchen and living spaces, perfect for everyday living and entertaining. The kitchen features stainless steel appliances, and upstairs you’ll enjoy the convenience of laundry on the bedroom level. The walk-in level includes a rough-in for an additional bathroom, offering flexibility for future use. Outside, enjoy one of the largest backyards in the townhome section of the community, fully fenced and ready for pets, entertaining, or relaxing. Perfect for commuters with convenient access to Route 522 and I-81, while just minutes from Downtown Winchester’s Walking Mall, shopping, restaurants, breweries, and nearby walking trails. This end unit offers the space, location, and convenience you’ve been looking for!

Welcome to this bright and inviting end-unit townhome in Winchester! Additional windows fill the home with natural light, while the open layout creates an easy flow between the kitchen and living spaces, perfect for everyday living and entertaining. The kitchen features stainless steel appliances, and upstairs you’ll enjoy the convenience of laundry on the bedroom level. The walk-in level includes a rough-in for an additional bathroom, offering flexibility for future use. Outside, enjoy one of the largest backyards in the townhome section of the community, fully fenced and ready for pets, entertaining, or relaxing. Perfect for commuters with convenient access to Route 522 and I-81, while just minutes from Downtown Winchester’s Walking Mall, shopping, restaurants, breweries, and nearby walking trails. This end unit offers the space, location, and convenience you’ve been looking for!

100 Stribling Way, Winchester

Listing courtesy of Samson Properties. Contact:

$369,990

***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. Home with backing to trees for added privacy and peaceful views. This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone!

***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. Home with backing to trees for added privacy and peaceful views. This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone!

229 Monteith Dr, Winchester

Listing courtesy of DRB Group Realty, LLC. Contact:

$245,000

Roof replaced in 2020. Water heater: 2026. NEW PRICE! Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs offers two generously sized bedrooms with ample closet space and a full bath. Step outside to the Trex deck and manageable backyard, perfect for relaxing or entertaining. Off-street parking for two vehicles is a rare bonus in this downtown location. Whether you're a first-time buyer, downsizer, or investor, this home offers comfort, convenience, and an excellent location with easy access to I-81 and Northern Virginia. Enjoy everything Winchester has to offer, including the vibrant Old Town district, locally owned restaurants and boutiques, breweries, cultural attractions, and historic landmarks. Schedule your private showing today! All sizes are approximate.

Roof replaced in 2020. Water heater: 2026. NEW PRICE! Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs offers two generously sized bedrooms with ample closet space and a full bath. Step outside to the Trex deck and manageable backyard, perfect for relaxing or entertaining. Off-street parking for two vehicles is a rare bonus in this downtown location. Whether you're a first-time buyer, downsizer, or investor, this home offers comfort, convenience, and an excellent location with easy access to I-81 and Northern Virginia. Enjoy everything Winchester has to offer, including the vibrant Old Town district, locally owned restaurants and boutiques, breweries, cultural attractions, and historic landmarks. Schedule your private showing today! All sizes are approximate.

103 E Germain St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$359,990

***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone!*Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone!*Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

237 Monteith Dr, Winchester

Listing courtesy of DRB Group Realty, LLC. Contact:

$220,000

Great investment opportunity for this centrally located rambler! Just minutes from Route 7 and I-81, this property offers convenient access to shopping, restaurants, and everyday amenities. The current tenant is under lease through 11/13/26, providing immediate rental income for an investor. With some sweat equity and a few updates, there is potential to increase the rental income significantly. Looking for a home of your own? This property could also be a great opportunity for a first-time homebuyer looking to build equity and make it their own. The home features LVP flooring throughout and a spacious, flat yard with plenty of room to enjoy the outdoors. Whether you're looking to add to your investment portfolio or find a home with room to grow, this one is worth a look!

2 Beds ⋅ 1 Baths

Great investment opportunity for this centrally located rambler! Just minutes from Route 7 and I-81, this property offers convenient access to shopping, restaurants, and everyday amenities. The current tenant is under lease through 11/13/26, providing immediate rental income for an investor. With some sweat equity and a few updates, there is potential to increase the rental income significantly. Looking for a home of your own? This property could also be a great opportunity for a first-time homebuyer looking to build equity and make it their own. The home features LVP flooring throughout and a spacious, flat yard with plenty of room to enjoy the outdoors. Whether you're looking to add to your investment portfolio or find a home with room to grow, this one is worth a look!

187 Valley Mill Rd, Winchester

Listing courtesy of Samson Properties. Contact:

$364,900

NO HOA-City of Winchester on cul-de-sac with a spacious yard that feels like a private oasis.Charming and inviting townhome offering an unusual and versatile four-level floor plan with wonderful indoor and outdoor living spaces! The main level features a welcoming living room with a beautiful bay window, fireplace and built-in shelving, along with a dining room accented by crown molding and chair rail. A convenient closet provides additional storage for china and linens. The updated kitchen offers Corian countertops and includes a refrigerator, dishwasher, disposal, built in microwave and range. A half bath completes the main level. (a chairlift from the first level to the second level can remain with the property or removed) The second level offers three comfortable bedrooms and a full bath that has been updated. The first lower level expands the living space with a finished recreation room featuring built-ins, plus separate laundry area and half bath. Step outside to enjoy the beautifully landscaped rear yard—an unusually generous outdoor space for a townhome. The spacious deck is perfect for relaxing, entertaining or enjoying the surrounding greenery, with convenient access from the lower level recreation room. There is access from the front yard via steps on the side of the home leading to the deck providing both access to the lower level recreation room and deck. Additional steps from the deck lead down to the lush backyard. The lowest level is unfinished and provides a small workshop area, abundant storage and a walkout to the lush rear yard at ground level. An exceptional opportunity to enjoy the space and flexibility of a four level townhome complimented by a wonderfully private and expansive outdoor setting. Additional items of note: New roof 2025, new heat pump 2025, new hot water heater 2026, full bath remodeled 2024, new clothes dryer, 2024, new refrigerator 2020, Exterior painted 2017, windows replaced-2015 (most but not living room bay), kitchen remodeled,2015, wood walkway built on the side of the house, 2015 and additional insulation in attic, 2015

NO HOA-City of Winchester on cul-de-sac with a spacious yard that feels like a private oasis.Charming and inviting townhome offering an unusual and versatile four-level floor plan with wonderful indoor and outdoor living spaces! The main level features a welcoming living room with a beautiful bay window, fireplace and built-in shelving, along with a dining room accented by crown molding and chair rail. A convenient closet provides additional storage for china and linens. The updated kitchen offers Corian countertops and includes a refrigerator, dishwasher, disposal, built in microwave and range. A half bath completes the main level. (a chairlift from the first level to the second level can remain with the property or removed) The second level offers three comfortable bedrooms and a full bath that has been updated. The first lower level expands the living space with a finished recreation room featuring built-ins, plus separate laundry area and half bath. Step outside to enjoy the beautifully landscaped rear yard—an unusually generous outdoor space for a townhome. The spacious deck is perfect for relaxing, entertaining or enjoying the surrounding greenery, with convenient access from the lower level recreation room. There is access from the front yard via steps on the side of the home leading to the deck providing both access to the lower level recreation room and deck. Additional steps from the deck lead down to the lush backyard. The lowest level is unfinished and provides a small workshop area, abundant storage and a walkout to the lush rear yard at ground level. An exceptional opportunity to enjoy the space and flexibility of a four level townhome complimented by a wonderfully private and expansive outdoor setting. Additional items of note: New roof 2025, new heat pump 2025, new hot water heater 2026, full bath remodeled 2024, new clothes dryer, 2024, new refrigerator 2020, Exterior painted 2017, windows replaced-2015 (most but not living room bay), kitchen remodeled,2015, wood walkway built on the side of the house, 2015 and additional insulation in attic, 2015

802 Appleseed Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$339,000

Great Commuter Location in Brookland Manor!! 3 level townhome features 3 bedrooms, 2 full baths, 2 half baths, one car garage, master suite with full bath (shower and soaking tub) and walk-in closet, family room on lower level, large living room and kitchen on main level. 50-year shingles installed in 2022, new air handler in 2025. Seller is listing both for sale or lease.