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This building located at 435 N. Cameron Street in Winchester, Virginia, formerly housed the Winchester Rescue Mission. Architecturally, it is a two-story, brick commercial building featuring prominent display windows across the front. The brickwork was formerly painted a crisp white, contrasted by dark framing around the windows and doors. Presently, there is a hand painted mural that covers the entire front of the building and the south side. The building with approximately 7,292 SF on two floors is sited on a lot with land area of 0.17 +/- acres with approximately 50 feet of frontage on Cameron Street. There are approximately 14 rooms. The building was constructed in 1931. The property has served as a homeless shelter since it was purchased for the nonprofit in July 1973. In recent years, the shelter has provided emergency overnight lodging for men and women, alongside hot meals, spiritual counseling, and mental health services. The facility had provided approximately 60 beds for men and women. Because the shelter consistently ran out of beds at peak capacity, the operators had to turn away individuals daily and the organization broke ground and expanded their facilities at their new facility on 2655 Valley Avenue.

435 N Cameron St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$354,900

"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:

$699,000

If you are looking for space to spread out, look no further! This home offers 7 bedrooms and 5 full baths. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

7 Beds ⋅ 5 Baths

If you are looking for space to spread out, look no further! This home offers 7 bedrooms and 5 full baths. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$1,450,000

5900 sf of Old Town elegance located in the middle of the walking mall at the fountain. 2 floors of finished space that currently is used for retail on the mail level and a kitchen lab on the second floor. Two entrances from the front off of the walking mall and two entrances from the rear. Property included 10 parking spaces off of Indian Alley. Call broker for showing and further details.

Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$320,000

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

3 Beds ⋅ 2 Baths

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

1048 Woodland Ave, Winchester

Listing courtesy of Re/Max Roots. Contact:

$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:

$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:

$750,000

Rare Historical Winchester Investment Opportunity – Three Properties in One Location An outstanding investment opportunity awaits in the heart of Winchester City. This unique portfolio comprises three properties positioned along the same street, offering exceptional potential for developers, investors, or those seeking a landmark project for multi-unit rentals or commercial development. Both existing multi-unit buildings have a total of 5 units. The properties benefit from an approved site plan and historical planning approval, providing a valuable foundation for future development, subject to the necessary consents and any relevant conditions. With the convenience of city-center living on the doorstep, the site is ideally placed close to Winchester’s historic attractions, independent shops, restaurants, cafés, transport links, and highly regarded schools. Opportunities of this scale and location are rarely available. Whether considered as a strategic investment, a redevelopment project, or a long-term development opportunity, this is a compelling chance to secure three properties together in the historic heart of Winchester. Key features: • Three properties located on one street • Prime central Winchester location • Approved site plan • Historical planning approval • Strong investment and development potential • Close to shops, restaurants, schools, transport links, and historic landmarks • Rare opportunity to acquire the properties as one portfolio 3 Physical property addresses are 224 Sharp Street, 225 E. Boscowan Street, and 11 S East Lane Interested parties should make their own inquiries with Winchester City Council and obtain independent legal, planning, and financial advice before proceeding.

224 Sharp St, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

$615,000

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

5 Beds ⋅ 4 Baths

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

922 Wayne Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$409,000

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

3 Beds ⋅ 3 Baths

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

422 S Loudoun St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$1,100,000

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

6 Beds ⋅ 6 Baths

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

1030 Breckinridge Ln, Winchester

Listing courtesy of Samson Properties. Contact:

$747,000

Rare opportunity to own a historic landmark in the heart of Old Town Winchester’s iconic Walking Mall. This impressive three-story commercial building offers approximately 9,276 square feet and features two retail storefronts in one of the Shenandoah Valley’s most sought-after downtown locations. Both retail spaces are currently leased, providing immediate and reliable rental income for investors. With established tenants already in place, this property presents an excellent opportunity to acquire a performing asset in a premier downtown location while benefiting from existing cash flow. Positioned along the vibrant pedestrian mall, the property benefits from exceptional visibility, steady foot traffic, and exposure to the countless community events, festivals, dining destinations, and boutique shopping experiences that make Old Town Winchester a regional attraction. The versatile floor plan provides endless possibilities for retail, office, restaurant, studio, mixed-use, or investment opportunities. The building showcases attractive storefronts, large display windows, and multiple levels of usable space that can accommodate a variety of business needs. Upper floors offer additional opportunities for expansion, office suites, creative workspaces, storage, or redevelopment potential (subject to applicable approvals). Whether you're an investor seeking a premier downtown asset, an entrepreneur looking to establish a flagship location, or someone passionate about preserving a piece of Winchester's rich history, this is a truly exceptional offering. Prime location, historic character, and significant square footage combine to create a one-of-a-kind ownership opportunity in the center of Winchester's thriving Walking Mall district.

14-16 S Loudoun St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$385,000

Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing stores, and professional services allows you to start or end your day at a plethora of local store fronts only steps from your home. Being only 2 years young allows the comfort of practically a new home in impeccable condition. Two car garage, front porch, and a recreation room greet you on the ground floor. Main level modern kitchen complemented by soft close cabinets and stunning countertops transitioning to the spacious living room with immense amount of natural light and back porch for morning coffee or evening happy hour. Condo association takes care of lawn maintenance and snow removal.

3 Beds ⋅ 3 Baths

Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing stores, and professional services allows you to start or end your day at a plethora of local store fronts only steps from your home. Being only 2 years young allows the comfort of practically a new home in impeccable condition. Two car garage, front porch, and a recreation room greet you on the ground floor. Main level modern kitchen complemented by soft close cabinets and stunning countertops transitioning to the spacious living room with immense amount of natural light and back porch for morning coffee or evening happy hour. Condo association takes care of lawn maintenance and snow removal.

3135 Eton Pl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$274,000

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

3 Beds ⋅ 2 Baths

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

519 Virginia Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$450,000

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

4 Beds ⋅ 2 Baths

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

501 Fox Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$425,000

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

3 Beds ⋅ 2 Baths

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

413 Superior Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$299,900

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

3 Beds ⋅ 1 Baths

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

12 N Purcell Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$625,000

Historic office building located just south of the Old Town Walking Mall and the Government and Judicial Center. The 3,618 sq ft property includes two finished floors that create a continuous flow for business operations and an aesthetically pleasing workspace. The rear of the building features a two level outside porch with ceiling fan for relaxing. The building has an unfinished walkout basement, offering a value-add opportunity to the new owner. The fully floored attic provides additional storage. Additional features include 7 office spaces, a conference room, 2 restrooms, and a kitchenette. Two designated parking spaces are in the rear of the property, plus street parking. Great location for an attorney, architect, engineer, real estate, title company, counseling, etc.

407 S Loudoun St, Winchester

Listing courtesy of Commercial Specialists. Contact:

$350,000

This large two-story home seamlessly blends the timeless character of the 1930s with the modern updates today’s buyers appreciate. A classic covered front porch welcomes you home and offers the perfect place to enjoy your morning coffee or relax at the end of the day. Inside, classsic hardwood floors, high ceilings, elegant crown and baseboard molding, and stunning original built-in cabinetry between the living and formal dining rooms showcase the home’s historic charm. Thoughtful updates provide added comfort and convenience, including a renovated kitchen, updated bathrooms, bedroom-level laundry, new windows (2023), a new water heater (2023), and a new roof (2024). Situated on one of the larger lots in the neighborhood, this property also offers incredible outdoor potential. With convenient a convenient shared drive to the rear of the home where there’s plenty of room to add a garage, oversized workshop, or storage shed while still maintaining a spacious backyard for entertaining, gardening, or simply relaxing outdoors. Full of character, thoughtfully updated, and ideally located near all that Old Town Winchester has to offer, this special home is one you won’t want to miss!

4 Beds ⋅ 2 Baths

This large two-story home seamlessly blends the timeless character of the 1930s with the modern updates today’s buyers appreciate. A classic covered front porch welcomes you home and offers the perfect place to enjoy your morning coffee or relax at the end of the day. Inside, classsic hardwood floors, high ceilings, elegant crown and baseboard molding, and stunning original built-in cabinetry between the living and formal dining rooms showcase the home’s historic charm. Thoughtful updates provide added comfort and convenience, including a renovated kitchen, updated bathrooms, bedroom-level laundry, new windows (2023), a new water heater (2023), and a new roof (2024). Situated on one of the larger lots in the neighborhood, this property also offers incredible outdoor potential. With convenient a convenient shared drive to the rear of the home where there’s plenty of room to add a garage, oversized workshop, or storage shed while still maintaining a spacious backyard for entertaining, gardening, or simply relaxing outdoors. Full of character, thoughtfully updated, and ideally located near all that Old Town Winchester has to offer, this special home is one you won’t want to miss!

1008 S Cameron St, Winchester

Listing courtesy of Redfin Corporation. Contact:

$439,900

Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopping, schools, the hospital, and other everyday amenities, this home combines a prime location with thoughtful updates. Inside, you'll find two recently remodeled bathrooms featuring modern finished and stylish upgrades. The functional layout provides comfortable living spaces perfect for everyday life. The basement has also been professionally waterproofed, and the existing waterproofing warranty will transfer to the new owner, providing added peace of mind. Step outside to enjoy the fully fenced backyard, offering privacy and plenty of space for children, pets, or entertaining. The extensive hardscaping creates a beautiful, low-maintenance outdoor retreat, while the paver driveway adds outstanding curb appeal. An above-ground pool provides the perfect place to cool off on warm summer days, and the storage shed offers ample space for lawn equipment, tools, and seasonal items. Move-in ready and conveniently located, this home offers the perfect blend of comfort, style. and accessibility. Don't miss your opportunity to make it yours-schedule your private showing today!

3 Beds ⋅ 2 Baths

Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopping, schools, the hospital, and other everyday amenities, this home combines a prime location with thoughtful updates. Inside, you'll find two recently remodeled bathrooms featuring modern finished and stylish upgrades. The functional layout provides comfortable living spaces perfect for everyday life. The basement has also been professionally waterproofed, and the existing waterproofing warranty will transfer to the new owner, providing added peace of mind. Step outside to enjoy the fully fenced backyard, offering privacy and plenty of space for children, pets, or entertaining. The extensive hardscaping creates a beautiful, low-maintenance outdoor retreat, while the paver driveway adds outstanding curb appeal. An above-ground pool provides the perfect place to cool off on warm summer days, and the storage shed offers ample space for lawn equipment, tools, and seasonal items. Move-in ready and conveniently located, this home offers the perfect blend of comfort, style. and accessibility. Don't miss your opportunity to make it yours-schedule your private showing today!

153 Fox Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$385,000

Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

2 Beds ⋅ 2 Baths

Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

1853 Rosser Ln, Winchester

Listing courtesy of Realty FC. Contact:

$625,000

Roof 2017 - Water Heater 2017 - HVAC 2023. Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including elegant formal living and dining rooms ideal for entertaining. The heart of the home features an inviting open-concept kitchen and family room, creating the perfect space for everyday living and gathering with family and friends. A bright and airy sunroom provides the perfect spot to relax while overlooking the backyard. The finished basement offers exceptional flexibility with abundant space for a recreation room, home theater, fitness area, office, or guest suite. A spacious 2-car garage provides plenty of storage and convenience. Ideally situated in a prime location close to shopping, dining, schools, commuter routes, and all that Winchester has to offer, this impressive home combines space, convenience, and timeless appeal. If you're searching for a move-in-ready home with generous living areas and an unbeatable location, 1529 Dalton Place is one you won't want to miss. All sizes are approximate.

4 Beds ⋅ 4 Baths

Roof 2017 - Water Heater 2017 - HVAC 2023. Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including elegant formal living and dining rooms ideal for entertaining. The heart of the home features an inviting open-concept kitchen and family room, creating the perfect space for everyday living and gathering with family and friends. A bright and airy sunroom provides the perfect spot to relax while overlooking the backyard. The finished basement offers exceptional flexibility with abundant space for a recreation room, home theater, fitness area, office, or guest suite. A spacious 2-car garage provides plenty of storage and convenience. Ideally situated in a prime location close to shopping, dining, schools, commuter routes, and all that Winchester has to offer, this impressive home combines space, convenience, and timeless appeal. If you're searching for a move-in-ready home with generous living areas and an unbeatable location, 1529 Dalton Place is one you won't want to miss. All sizes are approximate.

1529 Dalton Pl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$1,495,000

Great Warehouse in the City of Winchester, approximately 13,000 sq. ft., Great Space for all Your needs!

567 N Cameron St, Winchester

Listing courtesy of Compass. Contact:

$399,000

Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a charming community park, this home is ideally located just minutes from Winchester Medical Center, the Museum of the Shenandoah Valley, and Old Town Winchester's restaurants, shops, and entertainment.

4 Beds ⋅ 2 Baths

Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a charming community park, this home is ideally located just minutes from Winchester Medical Center, the Museum of the Shenandoah Valley, and Old Town Winchester's restaurants, shops, and entertainment.

1310 Whittier Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$267,000

1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room for sleeping or work-from-home use. Outdoors, a covered front porch offers a shaded sitting area, a rear deck extends the usable outdoor space, and a fully fenced backyard defines the grounds for outdoor activities. Clean interior finishes complete this well-maintained residence with practical amenities throughout every room.. Included 100-Day Home Warranty with buyer activation

3 Beds ⋅ 1 Baths

1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room for sleeping or work-from-home use. Outdoors, a covered front porch offers a shaded sitting area, a rear deck extends the usable outdoor space, and a fully fenced backyard defines the grounds for outdoor activities. Clean interior finishes complete this well-maintained residence with practical amenities throughout every room.. Included 100-Day Home Warranty with buyer activation

1314 S Braddock St, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact:

$675,000

Position your business in the heart of Winchester's premier retail corridor. This highly visible commercial outparcel offers an outstanding opportunity for retail, restaurant, medical, financial, or service-oriented development in one of the region's strongest shopping destinations. Located just off South Pleasant Valley Road with immediate access to Interstate 81, the property is surrounded by major national retailers including Lowe's, Walmart, Kohl's, Home Depot, Apple Blossom Mall, and numerous restaurants, hotels, and service businesses, creating exceptional consumer traffic throughout the day. The property sits within Winchester's primary retail trade area, drawing customers from the Shenandoah Valley, Northern Virginia, West Virginia, and Maryland. Current operating drive-thru. Property Highlights Prime 0.57-acre commercial outparcel Zoned CM-1 allowing a wide variety of commercial uses. Utilities available with water and sewer connections. Excellent access from Patsy Cline Boulevard and South Pleasant Valley Road. Minutes from I-81 interchange. Surrounded by established national retailers and restaurants. Strong daytime employment and regional consumer base. Ideal for: Quick-service or fast-casual restaurant Coffee shop Medical or dental office Financial institution Retail showroom Professional office Convenience retail Specialty retail Whether you're developing a flagship retail location, constructing a freestanding commercial building, or creating a custom build-to-suit opportunity, this site offers the visibility, accessibility, and surrounding retail synergy needed for long-term success.

535 Patsy Cline Blvd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$600,000

This charming Colonial home, built in 1952, exudes warmth and character, making it a perfect retreat. Nestled in the heart of the City of Winchester, this residence features three spacious bedrooms and one and a half bathrooms, ideal for comfortable living. Step inside to discover beautiful hardwood floors that flow throughout, complemented by a traditional floor plan that invites gatherings in the formal dining room. The upgraded countertops and butler's pantry in the kitchen enhance functionality, while the cozy fireplace adds a touch of elegance to the living space. The home boasts a well-designed attic and a convenient basement laundry area, ensuring ample storage and practicality. Outside, the extensive hardscape and outbuilding provide versatile outdoor space for relaxation or hobbies. Located in a vibrant community, residents enjoy easy access to local parks, perfect for leisurely strolls or picnics. The neighborhood is known for its friendly atmosphere and community events, fostering a sense of belonging. Excellent schools are just a stone's throw away, making this location ideal for those seeking quality education options. With on-street parking and a generous lot size, this property balances convenience and comfort. Experience the charm of this delightful home and the welcoming community that surrounds it.

3 Beds ⋅ 2 Baths

This charming Colonial home, built in 1952, exudes warmth and character, making it a perfect retreat. Nestled in the heart of the City of Winchester, this residence features three spacious bedrooms and one and a half bathrooms, ideal for comfortable living. Step inside to discover beautiful hardwood floors that flow throughout, complemented by a traditional floor plan that invites gatherings in the formal dining room. The upgraded countertops and butler's pantry in the kitchen enhance functionality, while the cozy fireplace adds a touch of elegance to the living space. The home boasts a well-designed attic and a convenient basement laundry area, ensuring ample storage and practicality. Outside, the extensive hardscape and outbuilding provide versatile outdoor space for relaxation or hobbies. Located in a vibrant community, residents enjoy easy access to local parks, perfect for leisurely strolls or picnics. The neighborhood is known for its friendly atmosphere and community events, fostering a sense of belonging. Excellent schools are just a stone's throw away, making this location ideal for those seeking quality education options. With on-street parking and a generous lot size, this property balances convenience and comfort. Experience the charm of this delightful home and the welcoming community that surrounds it.

1311 Handley Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$249,000

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

1 Beds ⋅ 1 Baths

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

135 S Kent St Unit 202, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$569,000

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

4 Beds ⋅ 4 Baths

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

687 Woodland Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,175,000

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

6 Beds ⋅ 7 Baths

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

730 Merrimans Ln, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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