$439,900 Welcome home to this charming all-brick rancher, offering timeless appeal, beautiful hardwood floors throughout, and wonderful potential to make it your own! The inviting living room features a wood-burning fireplace, while the dining area provides a comfortable space for everyday meals and entertaining. The updated kitchen boasts granite countertops, and the remodeled bathroom adds a fresh, modern touch. Enjoy relaxing in the sun porch or entertaining outdoors on the stamped concrete patio, surrounded by gorgeous mature trees in the backyard. Replacement windows and architectural shingles, approximately nine years old, provide additional peace of mind. The walk-up attic offers exciting possibilities for additional living space, while the unfinished basement features a rough-in for a future bathroom and the opportunity to expand your finished living area. With three bedrooms, classic brick construction, and room to grow, this home is full of possibilities. Don't miss the opportunity to make it yours! 3 Beds ⋅ 1 Baths Welcome home to this charming all-brick rancher, offering timeless appeal, beautiful hardwood floors throughout, and wonderful potential to make it your own! The inviting living room features a wood-burning fireplace, while the dining area provides a comfortable space for everyday meals and entertaining. The updated kitchen boasts granite countertops, and the remodeled bathroom adds a fresh, modern touch. Enjoy relaxing in the sun porch or entertaining outdoors on the stamped concrete patio, surrounded by gorgeous mature trees in the backyard. Replacement windows and architectural shingles, approximately nine years old, provide additional peace of mind. The walk-up attic offers exciting possibilities for additional living space, while the unfinished basement features a rough-in for a future bathroom and the opportunity to expand your finished living area. With three bedrooms, classic brick construction, and room to grow, this home is full of possibilities. Don't miss the opportunity to make it yours! 411 Mosby St, Winchester Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:
$399,000 Welcome to this charming brick home located in the heart of Winchester! Filled with historic character, this home features beautiful hardwood floors throughout, spacious living areas, and oversized bedrooms. Enjoy relaxing on the covered front porch or entertaining on the covered back porch overlooking the large backyard. The home's timeless charm and generous room sizes offer a wonderful opportunity to make it your own. Conveniently located within walking distance to shops, restaurants, Shenandoah University, and all that downtown Winchester has to offer. A wonderful combination of historic charm, space, and location! 4 Beds ⋅ 2 Baths Welcome to this charming brick home located in the heart of Winchester! Filled with historic character, this home features beautiful hardwood floors throughout, spacious living areas, and oversized bedrooms. Enjoy relaxing on the covered front porch or entertaining on the covered back porch overlooking the large backyard. The home's timeless charm and generous room sizes offer a wonderful opportunity to make it your own. Conveniently located within walking distance to shops, restaurants, Shenandoah University, and all that downtown Winchester has to offer. A wonderful combination of historic charm, space, and location! 317 S Kent St, Winchester Listing courtesy of Realty ONE Group Old Towne. Contact:
$229,000 Affordable homeowership opportunity in city limits. This town home has been cared for by owner for 35 years. Just needs some TLC to make it your own style. Living & dining with hardwood flooring. Bright kitchen with pantry and all appliances to convey. Plenty of storage with coat closet, 2 utility closets & hall closet. Laundry with shelving and space for freezer or more cabinety. Both bedroooms have double wide closets with double doors. 2 Liquid solar walls are an 80's system of plastic wall panels with internal liquid heated by sun to heat room. Owner has maintained regular servicing for gas heat & central AC. Private back yard with fencing . Not a thoroughfare street. Located convenient to dining, schools, retail, parks & rec, Green Circle Trail, just minutes to Shenandoah Universiry, the medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 and 37. Call today for a private tour 2 Beds ⋅ 2 Baths Affordable homeowership opportunity in city limits. This town home has been cared for by owner for 35 years. Just needs some TLC to make it your own style. Living & dining with hardwood flooring. Bright kitchen with pantry and all appliances to convey. Plenty of storage with coat closet, 2 utility closets & hall closet. Laundry with shelving and space for freezer or more cabinety. Both bedroooms have double wide closets with double doors. 2 Liquid solar walls are an 80's system of plastic wall panels with internal liquid heated by sun to heat room. Owner has maintained regular servicing for gas heat & central AC. Private back yard with fencing . Not a thoroughfare street. Located convenient to dining, schools, retail, parks & rec, Green Circle Trail, just minutes to Shenandoah Universiry, the medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 and 37. Call today for a private tour 23 Jigsaw Pl, Winchester Listing courtesy of Coldwell Banker Elite. Contact:
$255,000 329 Fairview Ave is a two-story Winchester single-family home with a bright, window-lined sunroom and a classic covered front porch. Plank flooring runs through the main living areas, where soft neutral walls and generous windows keep each room filled with natural light. The kitchen pairs crisp white cabinetry with ample counter space, a dishwasher, and a built-in microwave above the range. Carpeted bedrooms provide comfortable retreats, and the bathrooms include a tub with a dark tile surround and a wood vanity set against black-and-white mosaic floor tile. Out back, a grassy yard leaves room to garden or unwind outdoors. 3 Beds ⋅ 2 Baths 329 Fairview Ave is a two-story Winchester single-family home with a bright, window-lined sunroom and a classic covered front porch. Plank flooring runs through the main living areas, where soft neutral walls and generous windows keep each room filled with natural light. The kitchen pairs crisp white cabinetry with ample counter space, a dishwasher, and a built-in microwave above the range. Carpeted bedrooms provide comfortable retreats, and the bathrooms include a tub with a dark tile surround and a wood vanity set against black-and-white mosaic floor tile. Out back, a grassy yard leaves room to garden or unwind outdoors. 329 Fairview Ave, Winchester Listing courtesy of Open Door Brokerage, LLC. Contact:
$289,900 SINGLE-FAMILY LIVING IN WINCHESTER WITHOUT THE BIG PRICE TAG! Welcome to 322 Highland Ave, an opportunity to get the space of a 4-bedroom detached home at an approachable price point. With four bedrooms and 2.5 baths, there’s room to spread out, work from home, create a guest room, or simply enjoy the flexibility that extra bedrooms provide. This home is a great option for buyers who have been searching for more space without stretching into the price range of many larger single-family homes in the area. More house. More bedrooms. More possibilities. Come see the value for yourself! 4 Beds ⋅ 3 Baths SINGLE-FAMILY LIVING IN WINCHESTER WITHOUT THE BIG PRICE TAG! Welcome to 322 Highland Ave, an opportunity to get the space of a 4-bedroom detached home at an approachable price point. With four bedrooms and 2.5 baths, there’s room to spread out, work from home, create a guest room, or simply enjoy the flexibility that extra bedrooms provide. This home is a great option for buyers who have been searching for more space without stretching into the price range of many larger single-family homes in the area. More house. More bedrooms. More possibilities. Come see the value for yourself! 322 Highland Ave, Winchester Listing courtesy of EXP Realty, LLC. Contact:
$335,000 Well maintained three story, all brick townhome located in the City of Winchester. This home is on a quiet street and conveniently located close to shopping and restaurants. There are hardwood floors throughout the main level consisting of the kitchen/dining area, living room, and half bath. There are two nice sized bedrooms and one full bath on the upper level, along with separate laundry. (Maytag washer and dryer purchased in 2024 convey with property) The lower level has a finished living space with electric baseboard heat and could be comfortably used as a family room, office, or additional bedroom. Directly off the finished lower level are a one car garage and storage area. (The new freezer located in garage also conveys) This townhome comes with plenty of parking, whether it is street parking in front, a private concrete driveway in the rear, or the rear loading garage. (Townhome is freshly painted throughout.) Townhomes in this subdivision rarely come to market, so don't wait! 2 Beds ⋅ 2 Baths Well maintained three story, all brick townhome located in the City of Winchester. This home is on a quiet street and conveniently located close to shopping and restaurants. There are hardwood floors throughout the main level consisting of the kitchen/dining area, living room, and half bath. There are two nice sized bedrooms and one full bath on the upper level, along with separate laundry. (Maytag washer and dryer purchased in 2024 convey with property) The lower level has a finished living space with electric baseboard heat and could be comfortably used as a family room, office, or additional bedroom. Directly off the finished lower level are a one car garage and storage area. (The new freezer located in garage also conveys) This townhome comes with plenty of parking, whether it is street parking in front, a private concrete driveway in the rear, or the rear loading garage. (Townhome is freshly painted throughout.) Townhomes in this subdivision rarely come to market, so don't wait! 2660 Daniel Ter, Winchester Listing courtesy of MarketPlace REALTY. Contact:
$299,900 Charming, cheerful, and filled with natural light, this inviting 3-bedroom, 1-bath rancher makes a delightful first impression. Fresh yellow siding, mature trees, blooming hydrangeas, and classic boxwoods create beautiful curb appeal, while convenient main-level living makes the home as practical as it is welcoming. Inside, gleaming hardwood floors and abundant sunlight lend warmth to every room. The beautifully updated bath features a walk-in shower, and the centrally located kitchen offers generous cabinetry and plenty of room for shared meals. Ideally situated between the formal living room and cozy den, the kitchen provides an easy flow for everyday living and entertaining. Rich wood walls and a wood stove give the den its distinctive character. Adding a special piece of Winchester history, the paneling was salvaged from the former Lee-Jackson Hotel banquet room. Downstairs, the climate-controlled, partially finished lower level offers wonderful possibilities for a recreation room, playroom, home gym, or office, along with ample workshop and storage space. A relaxing screened porch overlooks the spacious backyard with peonies and a cherry tree, creating a peaceful spot to enjoy the outdoors. Lovingly cared for by the same family since it was built, this sweet home has been recently painted throughout and features roof (July 2025), new HVAC system (July 2026), update bathroom (2024) and newer 20-year tilt in windows, and updated lighting. Whether you are searching for your first home or looking to downsize, this special property is well worth a visit. Schedule your tour today! 3 Beds ⋅ 1 Baths Charming, cheerful, and filled with natural light, this inviting 3-bedroom, 1-bath rancher makes a delightful first impression. Fresh yellow siding, mature trees, blooming hydrangeas, and classic boxwoods create beautiful curb appeal, while convenient main-level living makes the home as practical as it is welcoming. Inside, gleaming hardwood floors and abundant sunlight lend warmth to every room. The beautifully updated bath features a walk-in shower, and the centrally located kitchen offers generous cabinetry and plenty of room for shared meals. Ideally situated between the formal living room and cozy den, the kitchen provides an easy flow for everyday living and entertaining. Rich wood walls and a wood stove give the den its distinctive character. Adding a special piece of Winchester history, the paneling was salvaged from the former Lee-Jackson Hotel banquet room. Downstairs, the climate-controlled, partially finished lower level offers wonderful possibilities for a recreation room, playroom, home gym, or office, along with ample workshop and storage space. A relaxing screened porch overlooks the spacious backyard with peonies and a cherry tree, creating a peaceful spot to enjoy the outdoors. Lovingly cared for by the same family since it was built, this sweet home has been recently painted throughout and features roof (July 2025), new HVAC system (July 2026), update bathroom (2024) and newer 20-year tilt in windows, and updated lighting. Whether you are searching for your first home or looking to downsize, this special property is well worth a visit. Schedule your tour today! 1308 Commerce, Winchester Listing courtesy of Colony Realty. Contact:
$298,900 PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00. 2 Beds ⋅ 2 Baths PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00. 828 Woodland Ave, Winchester Listing courtesy of Samson Properties. Contact:
$299,900 Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck complete with durable vinyl railing. Step inside to a spacious main level with an easy, open flow between the living and dining areas. The living room is warm and welcoming, centered around a wood-burning fireplace with built-in cabinetry on both sides, the perfect spot to settle in on a cool evening. The adjoining galley-style kitchen offers plenty of functionality with the laundry conveniently located just off the kitchen. Beyond the dining area, the home gets even better with a large bonus sunroom, complete with additional built-ins and an entire wall of pantry storage. Whether you envision it as a casual gathering space, home office, hobby area, or simply a place to enjoy the extra room, this flexible space adds even more versatility to the home. Upstairs, new carpeting runs throughout, complemented by fresh paint in the entire home. The brand-new full bathroom features a tub/shower combination and new vanity, giving the space a crisp, updated feel. The best part? The major exterior work has already been done, the home is clean and move-in ready, and there's still plenty of opportunity to bring your own style to the interior. Priced competitively, 1013 Orchard Hill Dr offers an opportunity to enjoy a desirable Winchester setting, the freedom of no HOA, and a home where the important updates have already been taken care of. Come see it for yourself and imagine what you'll do with the rest! 3 Beds ⋅ 2 Baths Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck complete with durable vinyl railing. Step inside to a spacious main level with an easy, open flow between the living and dining areas. The living room is warm and welcoming, centered around a wood-burning fireplace with built-in cabinetry on both sides, the perfect spot to settle in on a cool evening. The adjoining galley-style kitchen offers plenty of functionality with the laundry conveniently located just off the kitchen. Beyond the dining area, the home gets even better with a large bonus sunroom, complete with additional built-ins and an entire wall of pantry storage. Whether you envision it as a casual gathering space, home office, hobby area, or simply a place to enjoy the extra room, this flexible space adds even more versatility to the home. Upstairs, new carpeting runs throughout, complemented by fresh paint in the entire home. The brand-new full bathroom features a tub/shower combination and new vanity, giving the space a crisp, updated feel. The best part? The major exterior work has already been done, the home is clean and move-in ready, and there's still plenty of opportunity to bring your own style to the interior. Priced competitively, 1013 Orchard Hill Dr offers an opportunity to enjoy a desirable Winchester setting, the freedom of no HOA, and a home where the important updates have already been taken care of. Come see it for yourself and imagine what you'll do with the rest! 1013 Orchard Hill Dr, Winchester Listing courtesy of Realty ONE Group Old Towne. Contact:
$389,000 A RARE DOWNTOWN GEM IN THE HEART OF HISTORIC WINCHESTER! Discover the charm and convenience of this beautifully restored circa-1900 row house, ideally located just one block from Winchester’s iconic Walking Mall. Enjoy an exceptional walkable lifestyle with an array of restaurants, coffee shops, boutiques, and nightlife right outside your door - all with no HOA! Thoughtfully renovated from top to bottom, this home combines historic character with modern comfort, featuring updated plumbing and electrical systems, beautiful hardwood flooring, and a spacious gourmet kitchen with granite countertops and convenient direct access to the rear deck featuring a relatively new 6' privacy fence—perfect for outdoor dining, entertaining or simply relaxing after a long day. Additional highlights include a front-loading washer and dryer, ceramic tile bath, high-end window treatments, and a generous walk-in closet. The transformation continues outside, where the fully restored and freshly painted exterior has just been completed, including a newly painted metal roof, along with a freshly restained rear deck and front porch. Fresh interior paint throughout adds to the bright, polished presentation. Beautifully updated, exceptionally located, and full of character, this special downtown property is truly move-in ready and a must-see! Enjoy extra storage in the clean & dry cellar space featuring solid concrete floors. Contact the listing agent today for more info or your own private showing. 2 Beds ⋅ 1 Baths A RARE DOWNTOWN GEM IN THE HEART OF HISTORIC WINCHESTER! Discover the charm and convenience of this beautifully restored circa-1900 row house, ideally located just one block from Winchester’s iconic Walking Mall. Enjoy an exceptional walkable lifestyle with an array of restaurants, coffee shops, boutiques, and nightlife right outside your door - all with no HOA! Thoughtfully renovated from top to bottom, this home combines historic character with modern comfort, featuring updated plumbing and electrical systems, beautiful hardwood flooring, and a spacious gourmet kitchen with granite countertops and convenient direct access to the rear deck featuring a relatively new 6' privacy fence—perfect for outdoor dining, entertaining or simply relaxing after a long day. Additional highlights include a front-loading washer and dryer, ceramic tile bath, high-end window treatments, and a generous walk-in closet. The transformation continues outside, where the fully restored and freshly painted exterior has just been completed, including a newly painted metal roof, along with a freshly restained rear deck and front porch. Fresh interior paint throughout adds to the bright, polished presentation. Beautifully updated, exceptionally located, and full of character, this special downtown property is truly move-in ready and a must-see! Enjoy extra storage in the clean & dry cellar space featuring solid concrete floors. Contact the listing agent today for more info or your own private showing. 116 E Cork St, Winchester Listing courtesy of Keller Williams Realty. Contact:
$429,900 Fantastic location, classic brick charm, and plenty of space! This well-located brick rambler offers easy access to Route 50, Route 37, and I-81, while being just minutes from Valley Health. A long driveway, carport, concrete patio, and large, level backyard provide plenty of outdoor space and convenience. Inside, you’re welcomed by a light and bright living room featuring beautiful hardwood floors and a cozy fireplace. The kitchen opens directly to the dining room, creating a functional layout for everyday living and entertaining. The fully finished basement adds even more versatility, featuring two bedrooms, a spacious den with a second fireplace, and a kitchenette. Whether used for guests, extended living space, a home office, or recreation, the lower level offers plenty of possibilities. With a convenient location, generous yard, multiple living spaces, and a flexible finished basement, this home is ready to make your own! 5 Beds ⋅ 2 Baths Fantastic location, classic brick charm, and plenty of space! This well-located brick rambler offers easy access to Route 50, Route 37, and I-81, while being just minutes from Valley Health. A long driveway, carport, concrete patio, and large, level backyard provide plenty of outdoor space and convenience. Inside, you’re welcomed by a light and bright living room featuring beautiful hardwood floors and a cozy fireplace. The kitchen opens directly to the dining room, creating a functional layout for everyday living and entertaining. The fully finished basement adds even more versatility, featuring two bedrooms, a spacious den with a second fireplace, and a kitchenette. Whether used for guests, extended living space, a home office, or recreation, the lower level offers plenty of possibilities. With a convenient location, generous yard, multiple living spaces, and a flexible finished basement, this home is ready to make your own! 337 George St, Winchester Listing courtesy of Samson Properties. Contact:
$299,900 Enjoy downtown Winchester living with plenty of flexibility! This 4-bedroom, 2.5-bath townhome offers a functional layout in a convenient location close to restaurants, shopping, schools, Handley games, and all that downtown Winchester has to offer. The main level features a comfortable living area, kitchen with eat-in space, and access to a beautiful Trex deck overlooking the fully fenced backyard. Upstairs, you'll find three bedrooms and a full bath. The finished walk-out lower level adds even more versatility with a fourth bedroom, full bath, and laundry area. Step outside to a stamped concrete patio and fenced yard with storage shed. With multiple outdoor living spaces, off-street parking, and an incredibly convenient location, this home offers plenty of possibilities inside and out. 4 Beds ⋅ 3 Baths Enjoy downtown Winchester living with plenty of flexibility! This 4-bedroom, 2.5-bath townhome offers a functional layout in a convenient location close to restaurants, shopping, schools, Handley games, and all that downtown Winchester has to offer. The main level features a comfortable living area, kitchen with eat-in space, and access to a beautiful Trex deck overlooking the fully fenced backyard. Upstairs, you'll find three bedrooms and a full bath. The finished walk-out lower level adds even more versatility with a fourth bedroom, full bath, and laundry area. Step outside to a stamped concrete patio and fenced yard with storage shed. With multiple outdoor living spaces, off-street parking, and an incredibly convenient location, this home offers plenty of possibilities inside and out. 1 E Hart St, Winchester Listing courtesy of Realty ONE Group Old Towne. Contact:
$284,900 Enjoy the convenience of downtown Winchester living in this charming 2-bedroom, 2-bath townhome, ideally located within walking distance of restaurants, shopping, school games and more. The main level features a comfortable living area and an eat-in kitchen with doors leading to a beautiful Trex deck, perfect for morning coffee, grilling or relaxing at the end of the day. Upstairs, both bedrooms offer their own en-suite baths, with the primary bedroom also featuring a walk-in closet. The finished basement adds valuable bonus space with plenty of flexibility for a rec room, home gym, office or additional living area. From there, walk out to a beautiful stamped concrete patio and fully fenced backyard with a storage shed. With two great outdoor living spaces, a finished lower level and a location that makes it easy to enjoy everything downtown Winchester has to offer, this townhome packs a lot into a convenient footprint. 2 Beds ⋅ 3 Baths Enjoy the convenience of downtown Winchester living in this charming 2-bedroom, 2-bath townhome, ideally located within walking distance of restaurants, shopping, school games and more. The main level features a comfortable living area and an eat-in kitchen with doors leading to a beautiful Trex deck, perfect for morning coffee, grilling or relaxing at the end of the day. Upstairs, both bedrooms offer their own en-suite baths, with the primary bedroom also featuring a walk-in closet. The finished basement adds valuable bonus space with plenty of flexibility for a rec room, home gym, office or additional living area. From there, walk out to a beautiful stamped concrete patio and fully fenced backyard with a storage shed. With two great outdoor living spaces, a finished lower level and a location that makes it easy to enjoy everything downtown Winchester has to offer, this townhome packs a lot into a convenient footprint. 5 E Hart St, Winchester Listing courtesy of Realty ONE Group Old Towne. Contact:
$305,500 Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic home. 3 Beds ⋅ 2 Baths Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic home. 3 S Euclid Ave, Winchester Listing courtesy of Main Street Realty. Contact:
$357,000 Some homes simply feel right the moment you arrive—and this charming Cape Cod in an ideal in‑town Winchester location is one of them. Offering 3–4 bedrooms and 2.5 bathrooms, the layout flows with an easy, everyday comfort. The main level features two convenient bedrooms, a bright and inviting living room, a dedicated dining area, and a renovated kitchen with new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh, including new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, updated receptacles/switches/covers, a new roof, and updated plumbing for added peace of mind. Upstairs, two additional rooms and a full bathroom provide flexible space—whether you envision a fourth bedroom, office, or bonus retreat. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and direct walkout access to the backyard, creating an ideal setting for a second living area, guest space, or recreation zone. Outdoors, a spacious deck and fully fenced backyard with privacy fencing offer a comfortable retreat perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this is just moments from downtown Winchester’s shopping, restaurants, and everyday conveniences. Schedule your tour today and experience the feeling for yourself. 4 Beds ⋅ 3 Baths Some homes simply feel right the moment you arrive—and this charming Cape Cod in an ideal in‑town Winchester location is one of them. Offering 3–4 bedrooms and 2.5 bathrooms, the layout flows with an easy, everyday comfort. The main level features two convenient bedrooms, a bright and inviting living room, a dedicated dining area, and a renovated kitchen with new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh, including new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, updated receptacles/switches/covers, a new roof, and updated plumbing for added peace of mind. Upstairs, two additional rooms and a full bathroom provide flexible space—whether you envision a fourth bedroom, office, or bonus retreat. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and direct walkout access to the backyard, creating an ideal setting for a second living area, guest space, or recreation zone. Outdoors, a spacious deck and fully fenced backyard with privacy fencing offer a comfortable retreat perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this is just moments from downtown Winchester’s shopping, restaurants, and everyday conveniences. Schedule your tour today and experience the feeling for yourself. 621 Patterson Ave, Winchester Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
$325,000 Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for. 3 Beds ⋅ 2 Baths Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for. 2817 Papermill Rd, Winchester Listing courtesy of Weichert, REALTORS. Contact:
$300,000 Classic Winchester charm awaits at 310 Bellview Avenue! This inviting Cape Cod combines character, convenience, and plenty of opportunity to make the space your own. Inside, you’ll find hardwood floors, comfortable living areas, two main-level bedrooms, a full bathroom, and an additional half bath upstairs. A full basement offers extra storage and future possibilities, while the detached one-car garage provides even more room for parking, hobbies, or equipment. Out back, the spacious yard gives you room to relax, garden, entertain, or create the outdoor space you’ve been envisioning. With shopping, dining, parks, and Winchester amenities nearby, this home is ready for its next chapter. 2 Beds ⋅ 1 Baths Classic Winchester charm awaits at 310 Bellview Avenue! This inviting Cape Cod combines character, convenience, and plenty of opportunity to make the space your own. Inside, you’ll find hardwood floors, comfortable living areas, two main-level bedrooms, a full bathroom, and an additional half bath upstairs. A full basement offers extra storage and future possibilities, while the detached one-car garage provides even more room for parking, hobbies, or equipment. Out back, the spacious yard gives you room to relax, garden, entertain, or create the outdoor space you’ve been envisioning. With shopping, dining, parks, and Winchester amenities nearby, this home is ready for its next chapter. 310 Bellview Ave, Winchester Listing courtesy of Keller Williams Realty. Contact:
$499,900 Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds. 3 Beds ⋅ 3 Baths Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds. 510 S Cameron St, Winchester Listing courtesy of Samson Properties. Contact:
$471,000 A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you can easily walkout to a huge concrete patio for a great family cookout and joyful huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secured... In the upper level of the house, you will find the masterbedroom with a masterbath, and a second bath for the 2 other bedroom. This property is minutes away from the Winchester Historic downtown and a short drive to Shenandoah University. This is a well kept property and is waiting for you to make it yours! Schedule your showing online and allow time since the seller has two little dogs to take care off when you go show it. There are video cameras at the property. 3 Beds ⋅ 3 Baths A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you can easily walkout to a huge concrete patio for a great family cookout and joyful huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secured... In the upper level of the house, you will find the masterbedroom with a masterbath, and a second bath for the 2 other bedroom. This property is minutes away from the Winchester Historic downtown and a short drive to Shenandoah University. This is a well kept property and is waiting for you to make it yours! Schedule your showing online and allow time since the seller has two little dogs to take care off when you go show it. There are video cameras at the property. 421 Longview Ave, Winchester Listing courtesy of Samson Properties. Contact:
$292,500 Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the home’s fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable additional storage and utility space. With its attractive updates, functional floor plan, outdoor space, storage shed, and convenient parking, 621 Watson Avenue is a standout opportunity in Winchester! Whether you're searching for a comfortable place to call home or a great investment property, this beautifully refreshed duplex is ready for its next owner. Schedule your tour on ShowingTime today and see why 621 Watson Avenue stands out! 3 Beds ⋅ 2 Baths Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the home’s fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable additional storage and utility space. With its attractive updates, functional floor plan, outdoor space, storage shed, and convenient parking, 621 Watson Avenue is a standout opportunity in Winchester! Whether you're searching for a comfortable place to call home or a great investment property, this beautifully refreshed duplex is ready for its next owner. Schedule your tour on ShowingTime today and see why 621 Watson Avenue stands out! 621 Watson Ave, Winchester Listing courtesy of Samson Properties. Contact:
$325,000 Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own! 4 Beds ⋅ 2 Baths Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own! 805 S Kent St, Winchester Listing courtesy of Weichert, REALTORS. Contact:
$359,000 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! 3 Beds ⋅ 2 Baths 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. 2 Beds ⋅ 2 Baths 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:
$409,000 Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully. 4 Beds ⋅ 1 Baths Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully. 322 E Piccadilly, Winchester Listing courtesy of Long & Foster Real Estate, 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! 3 Beds ⋅ 3 Baths "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:
$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! 3 Beds ⋅ 2 Baths 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:
$419,000 Larger than it appears, this beautiful 3‑bedroom, 2‑bathroom home sits on a convenient street just minutes from historic downtown Winchester. The location offers effortless access to main commuter roads, making daily travel smooth and stress‑free. It’s also close to Shenandoah University, adding even more appeal for investors, students, faculty, or anyone who values proximity to campus and city amenities. Inside, the layout provides exceptional flexibility — the home can function as two completely separate rentals, giving it true income‑producing capabilities while maintaining all the original details you provided. A nice deck extends your living space outdoors, overlooking a large, flat, fully fenced backyard perfect for relaxing, entertaining, or tenant use. This is a great opportunity in a prime Winchester location. Come take a look and see the potential for yourself. 3 Beds ⋅ 2 Baths Larger than it appears, this beautiful 3‑bedroom, 2‑bathroom home sits on a convenient street just minutes from historic downtown Winchester. The location offers effortless access to main commuter roads, making daily travel smooth and stress‑free. It’s also close to Shenandoah University, adding even more appeal for investors, students, faculty, or anyone who values proximity to campus and city amenities. Inside, the layout provides exceptional flexibility — the home can function as two completely separate rentals, giving it true income‑producing capabilities while maintaining all the original details you provided. A nice deck extends your living space outdoors, overlooking a large, flat, fully fenced backyard perfect for relaxing, entertaining, or tenant use. This is a great opportunity in a prime Winchester location. Come take a look and see the potential for yourself. 1412 S Loudoun St, Winchester Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
$299,900 This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey! 2 Beds ⋅ 2 Baths This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey! 2519 Hockman Ave, Winchester Listing courtesy of Link Realty Services LLC. Contact:
$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! 2 Beds ⋅ 2 Baths 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: