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Seize the chance to establish your business with this prime commercial office space at 650 Millwood Avenue in Winchester, VA. The first time this iconic property has been for sale in 40 years! This is an unparalleled opportunity to secure over 2,600 square feet of professional, highly versatile space featuring multiple private offices and dedicated meeting areas. The location is truly exceptional: situated directly next to Shenandoah University, the property offers incredible visibility on a major artery that sees a traffic count of around 30,000 cars per day. This prominent position is ideal for medical/professional services, financial firms, or any enterprise seeking maximum brand recognition. Crucially, the site includes convenient on-site parking for approximately 15 vehicles, guaranteeing easy access for every client and employee.

650 Millwood Ave, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: MarketPlace REALTY.

$1,014,300

Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and floor to ceiling windows cascading natural light throughout. The wrap around stairs will wrap around your heart with charm and the thrill to make this glorious mansion your own. Ideal as a single family residence but also zoned B1 for a bed and breakfast or upscale professional offices. Private parking in the rear is another downtown rarity. Includes carriage house. Outstanding residential, commercial, or mixed use investment opportunity, located in the heart of Winchester's Old Town!

6 Beds ⋅ 5 Baths

Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and floor to ceiling windows cascading natural light throughout. The wrap around stairs will wrap around your heart with charm and the thrill to make this glorious mansion your own. Ideal as a single family residence but also zoned B1 for a bed and breakfast or upscale professional offices. Private parking in the rear is another downtown rarity. Includes carriage house. Outstanding residential, commercial, or mixed use investment opportunity, located in the heart of Winchester's Old Town!

217 W Boscawen St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Samson Properties.

$1,000,000

18.18 Acres of B-2 Land. Close to Interstate, restaurant, hotels and retail. Utilities to site.

Front Royal Pike, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

Selling Office: Oakcrest Commercial Real Estate.

$1,000,000

Landmark, historic building for sale, Downtown Winchester, Virginia. Outstanding tenant history. Sold with 1st and 3rd floors leased, 2nd floor available for lease or end-user occupancy! A total of 7500 SF on three floors, located immediately adjacent to City Hall, across the street from public parking garage, and one block from Old Town Walking Mall and County municipal buildings. LOCATION LOCATION LOCATION. Iconically known as the Odd Fellows Building, built in 1930 and meticulously and historically restored for Class A office space with all modern amenities. Proforma GOI $100K+/annual. OPEX averages $20K/year (majority passed through to tenants via NNN fees). Ideal for owner-occupant wanting residual income, opportunity for growth, and a legacy investment. Two retail/office spaces on 1st floor, elevator to 2nd and 3rd floor office suites. Vaulted ceilings, massive, oversized windows, classic hardwood finishes, a true First Class building in meticulously cared-for condition. 2nd & 3rd floor residential conversion permitted under current zoning. See Agent Remarks for all recent upgrades, including NEW ROOF in 2023. Asking $1,299,000.

45 Boscawen St E, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Coldwell Banker Premier.

$999,990

Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederick County, the property combines peaceful rural living with convenient access to shopping, dining, and commuter routes. Custom built in 2020, this spacious residence offers approximately 4,800+ square feet of living space on the main level with 5 bedrooms and 4 bathrooms, office/exercise room, featuring generous living areas and a thoughtfully designed layout ideal for both everyday living, cooking, gatherings, and entertaining. The main level having wide hallways, spacious rooms, low ovens, comfort height toilets and front loading laundry makes this home handicap accessible. This one of a kind custom home built with low maintenance in mind. Situated on 10.41 unrestricted acres, the property provides plenty of room to enjoy the outdoors while maintaining privacy and flexibility for a variety of uses. A full unfinished basement with a bathroom rough-in, offers excellent potential for future expansion, allowing space for additional living areas, a recreation room, a home gym, or a workshop. Car enthusiasts and hobbyists will appreciate the 3-car attached garage along with a separate 2-car detached garage, providing abundant parking and storage. The property is also well suited for horse lovers, featuring fenced pasture and a run-in shed, making it ready for horses or other livestock. The property is set up for a homestead with blue berry and black berry bushes, fruit trees, 2 vegetable gardens, fenced pasture and backyard, and composting area. Enjoy the tranquility of country living while still being just a short drive from historic downtown Winchester, local shopping, dining, and outdoor recreation. With unrestricted acreage, equestrian potential, and modern construction, this property offers a rare opportunity for privacy, space, and convenience in the Shenandoah Valley. All sizes are approximate.

5 Beds ⋅ 4 Baths

Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederick County, the property combines peaceful rural living with convenient access to shopping, dining, and commuter routes. Custom built in 2020, this spacious residence offers approximately 4,800+ square feet of living space on the main level with 5 bedrooms and 4 bathrooms, office/exercise room, featuring generous living areas and a thoughtfully designed layout ideal for both everyday living, cooking, gatherings, and entertaining. The main level having wide hallways, spacious rooms, low ovens, comfort height toilets and front loading laundry makes this home handicap accessible. This one of a kind custom home built with low maintenance in mind. Situated on 10.41 unrestricted acres, the property provides plenty of room to enjoy the outdoors while maintaining privacy and flexibility for a variety of uses. A full unfinished basement with a bathroom rough-in, offers excellent potential for future expansion, allowing space for additional living areas, a recreation room, a home gym, or a workshop. Car enthusiasts and hobbyists will appreciate the 3-car attached garage along with a separate 2-car detached garage, providing abundant parking and storage. The property is also well suited for horse lovers, featuring fenced pasture and a run-in shed, making it ready for horses or other livestock. The property is set up for a homestead with blue berry and black berry bushes, fruit trees, 2 vegetable gardens, fenced pasture and backyard, and composting area. Enjoy the tranquility of country living while still being just a short drive from historic downtown Winchester, local shopping, dining, and outdoor recreation. With unrestricted acreage, equestrian potential, and modern construction, this property offers a rare opportunity for privacy, space, and convenience in the Shenandoah Valley. All sizes are approximate.

199 Laurel Grove Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: NextHome Realty Select.

$999,900

If you’re looking for a truly impressive property with unexpected benefits, welcome to 530 Laurel Grove Road. With nearly 6,000 finished square feet and five bedrooms and 5.5 baths, this home allows for easy gathering, relaxing, living, and entertaining—and includes a private in-law suite perfect for multi-generational living, guests, or rental potential. Ensconced in nature on 8.6 acres and surrounded by mature trees in a largely pastoral setting, this home offers peace and privacy, and the outdoor swimming pool and surrounding decks add another layer of enjoyment. You’ll also appreciate how this Winchester location gives you access to everything you love about town without living right in the city. The Colonial’s façade is brick and siding with a welcoming front porch just waiting for you to sit and enjoy the scenery or rock a while on the porch swing. Once you enter, you have two options. The right takes you to the all the main level features amidst pleasing neutral paint colors you’ll find throughout the home. A formal dining room allows for generous seating but also extra display cabinets and buffets. The kitchen has a bank of cabinets, long counters, and a four-seat island that includes the range. More informal dining sits adjacent, along with an inset, built-in desk space with cabinets. This shared space opens to a cheerful, whitewashed sunroom with a handsome wood ceiling, giving you natural views plus access to the deck and pool areas. Another side leads into a family room with a dramatic, vaulted wood ceiling, cozy corner fireplace, and lots of room for comfortable furniture. Back in the foyer, turn left through a door to find the convenient in-law suite, complete with a living room, kitchen and dining area, laundry and storage, and a spacious bedroom with attached full bath and walk-in closet. Private and accessible, it’s also available furnished, if desired. Upstairs houses the substantial owner’s suite with beautiful cherry hardwood floors and ample room for all your furniture. The ensuite features split vanities, beadboard wainscoting surrounding an appealing soaking tub, a walk-in shower, and water closet. A matching sitting room offers another pleasing, versatile space. Find three generous bedrooms and another two full baths on this floor. Downstairs is home to the fifth bedroom and attached full bath with an adjacent indoor, infrared sauna with chromotherapy benefits. A wood paneled den with hardwood floors and bar with a walk- out round out this level. Head outside and enjoy a large walkaround deck where seating and dining opportunities abound. Portions lead to the pool, hot tub, the backyard, and play areas. The home includes an attached two-car garage, but it’s a boon to have the detached, three-car garage, perfect for a workshop or car enthusiasts, or to utilize for additional storage. This home has been meticulously maintained and updated by only two owners and comes with multiple fuel sources to help with energy efficient heating and cooling. With space galore, comfort, privacy, and functionality, this is an amazing oasis near the city.

5 Beds ⋅ 6 Baths

If you’re looking for a truly impressive property with unexpected benefits, welcome to 530 Laurel Grove Road. With nearly 6,000 finished square feet and five bedrooms and 5.5 baths, this home allows for easy gathering, relaxing, living, and entertaining—and includes a private in-law suite perfect for multi-generational living, guests, or rental potential. Ensconced in nature on 8.6 acres and surrounded by mature trees in a largely pastoral setting, this home offers peace and privacy, and the outdoor swimming pool and surrounding decks add another layer of enjoyment. You’ll also appreciate how this Winchester location gives you access to everything you love about town without living right in the city. The Colonial’s façade is brick and siding with a welcoming front porch just waiting for you to sit and enjoy the scenery or rock a while on the porch swing. Once you enter, you have two options. The right takes you to the all the main level features amidst pleasing neutral paint colors you’ll find throughout the home. A formal dining room allows for generous seating but also extra display cabinets and buffets. The kitchen has a bank of cabinets, long counters, and a four-seat island that includes the range. More informal dining sits adjacent, along with an inset, built-in desk space with cabinets. This shared space opens to a cheerful, whitewashed sunroom with a handsome wood ceiling, giving you natural views plus access to the deck and pool areas. Another side leads into a family room with a dramatic, vaulted wood ceiling, cozy corner fireplace, and lots of room for comfortable furniture. Back in the foyer, turn left through a door to find the convenient in-law suite, complete with a living room, kitchen and dining area, laundry and storage, and a spacious bedroom with attached full bath and walk-in closet. Private and accessible, it’s also available furnished, if desired. Upstairs houses the substantial owner’s suite with beautiful cherry hardwood floors and ample room for all your furniture. The ensuite features split vanities, beadboard wainscoting surrounding an appealing soaking tub, a walk-in shower, and water closet. A matching sitting room offers another pleasing, versatile space. Find three generous bedrooms and another two full baths on this floor. Downstairs is home to the fifth bedroom and attached full bath with an adjacent indoor, infrared sauna with chromotherapy benefits. A wood paneled den with hardwood floors and bar with a walk- out round out this level. Head outside and enjoy a large walkaround deck where seating and dining opportunities abound. Portions lead to the pool, hot tub, the backyard, and play areas. The home includes an attached two-car garage, but it’s a boon to have the detached, three-car garage, perfect for a workshop or car enthusiasts, or to utilize for additional storage. This home has been meticulously maintained and updated by only two owners and comes with multiple fuel sources to help with energy efficient heating and cooling. With space galore, comfort, privacy, and functionality, this is an amazing oasis near the city.

530 Laurel Grove Rd, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Colony Realty.

$985,000

Discover Your Private Estate: 9.83 Acres of Country Charm with Resort-Style Amenities. NO HOA! AND with ANOTHER Price Improvement! Step into the unexpected with this exceptional property, perfectly blending the tranquility of a country retreat with the convenience of being just minutes from town. The inviting entry to the front door welcomes you into a beautifully maintained home, featuring three finished levels, five bedrooms, and four and a half bath, with spaces for every generation to thrive. The heart of the home is the expansive, light-filled kitchen, boasting ample cabinetry and counter space, including pristine quartz countertops—ideal for entertaining or a quiet morning coffee while enjoying picturesque views. Flowing seamlessly from the formal dining to the casual family room, 3-season porch, and the brightest bonus room, this home offers flexibility for creating, entertaining, and relaxing. Summers are extended with your own heated, resurfaced Gunite pool and hot tub, complemented by a magnificent pavilion with a gas grill hookup, fridge, and bar—the ultimate host’s paradise. Added luxuries include a full finished basement with a 5th bedroom, full bath, laundry, changing room, and space for a pool table, providing direct access to the pool area. The property is complete with a fully outfitted, main-level in-law suite offering a private entrance, kitchen, bath, and deck. Additional structures include a detached garage with an unfinished upstairs (roughed-in for kitchen/bath) and a charming barn, perfect for hobbies, storage, or your own backyard farm. Embrace the good life with nearly 10 private acres offering lush forest for exploring and cleared areas for gardening. Modern comfort is ensured with three-zone HVAC and 24 solar panels to ease utility costs. Recent updates include a new roof (2024) on the house and garage, a renovated Family Room (2019), and a remodeled Primary Bath (2020). This is more than a home—it’s a lifestyle where getting back to nature is just moments from local markets, restaurants, and shopping. Come experience the magic of this truly special property.

5 Beds ⋅ 5 Baths

Discover Your Private Estate: 9.83 Acres of Country Charm with Resort-Style Amenities. NO HOA! AND with ANOTHER Price Improvement! Step into the unexpected with this exceptional property, perfectly blending the tranquility of a country retreat with the convenience of being just minutes from town. The inviting entry to the front door welcomes you into a beautifully maintained home, featuring three finished levels, five bedrooms, and four and a half bath, with spaces for every generation to thrive. The heart of the home is the expansive, light-filled kitchen, boasting ample cabinetry and counter space, including pristine quartz countertops—ideal for entertaining or a quiet morning coffee while enjoying picturesque views. Flowing seamlessly from the formal dining to the casual family room, 3-season porch, and the brightest bonus room, this home offers flexibility for creating, entertaining, and relaxing. Summers are extended with your own heated, resurfaced Gunite pool and hot tub, complemented by a magnificent pavilion with a gas grill hookup, fridge, and bar—the ultimate host’s paradise. Added luxuries include a full finished basement with a 5th bedroom, full bath, laundry, changing room, and space for a pool table, providing direct access to the pool area. The property is complete with a fully outfitted, main-level in-law suite offering a private entrance, kitchen, bath, and deck. Additional structures include a detached garage with an unfinished upstairs (roughed-in for kitchen/bath) and a charming barn, perfect for hobbies, storage, or your own backyard farm. Embrace the good life with nearly 10 private acres offering lush forest for exploring and cleared areas for gardening. Modern comfort is ensured with three-zone HVAC and 24 solar panels to ease utility costs. Recent updates include a new roof (2024) on the house and garage, a renovated Family Room (2019), and a remodeled Primary Bath (2020). This is more than a home—it’s a lifestyle where getting back to nature is just moments from local markets, restaurants, and shopping. Come experience the magic of this truly special property.

410 Valley View Dr, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Colony Realty.

$985,000

This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath • 6500 sq ft • Wet bar in primary suite • 3-car garage • No HOA • Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 7 bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal for an in-law suite. Just off the kitchen, the covered back deck offers the perfect space for entertaining. Inside, you’ll find a kitchen that doesn’t compromise with Jenn-Air appliances, solid cherry cabinetry, and an oversized walk-in pantry, making cooking a joy. Hardwood and tile floors flow throughout the main level, while the lower-level recreation room boasts durable waterproof laminate flooring. The expansive primary suite offers a double-sided gas fireplace and a private wet bar/coffee bar with a sink—ideal for unwinding after a long day. The bedroom-level laundry room is fully equipped with cabinetry and a utility sink for added convenience. A 3-car side entry garage includes a half bath. Modern comforts include multiple furnaces & heat pumps, central vacuum & intercom system, front yard irrigation, an intercom system, and no costly monthly HOA dues. Whether you are seeking multi-generational living or space for a large family, this home blends thoughtful design with timeless upgrades. Recent updates include a new roof (2023), attic HVAC serviced/replaced A coil (2024), basement HVAC replaced A Coil & condenser (2021), and a new water softener (2025). See the virtual tour attached to the listing! One-owner, custom home, thoughtfully built with added upgrades by the builder! One year Home warranty offered with acceptable offer.

7 Beds ⋅ 6 Baths

This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath • 6500 sq ft • Wet bar in primary suite • 3-car garage • No HOA • Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 7 bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal for an in-law suite. Just off the kitchen, the covered back deck offers the perfect space for entertaining. Inside, you’ll find a kitchen that doesn’t compromise with Jenn-Air appliances, solid cherry cabinetry, and an oversized walk-in pantry, making cooking a joy. Hardwood and tile floors flow throughout the main level, while the lower-level recreation room boasts durable waterproof laminate flooring. The expansive primary suite offers a double-sided gas fireplace and a private wet bar/coffee bar with a sink—ideal for unwinding after a long day. The bedroom-level laundry room is fully equipped with cabinetry and a utility sink for added convenience. A 3-car side entry garage includes a half bath. Modern comforts include multiple furnaces & heat pumps, central vacuum & intercom system, front yard irrigation, an intercom system, and no costly monthly HOA dues. Whether you are seeking multi-generational living or space for a large family, this home blends thoughtful design with timeless upgrades. Recent updates include a new roof (2023), attic HVAC serviced/replaced A coil (2024), basement HVAC replaced A Coil & condenser (2021), and a new water softener (2025). See the virtual tour attached to the listing! One-owner, custom home, thoughtfully built with added upgrades by the builder! One year Home warranty offered with acceptable offer.

1020 Breckinridge Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Non Subscribing Office.

$960,000

Luxury custom home with a primary bedroom on the main floor. 5 partially wooded acres with an in-ground saltwater pool, upper-level Trex decks, screened porch, outdoor fireplace, and attached side-entry 4-car garage. Designed for entertaining and multi-generational living, this 5-bedroom, 4.5-bath home offers upscale finishes throughout plus a fully finished walkout basement with a second kitchen, additional living space, and gas fireplace. The gourmet kitchen features commercial-grade KitchenAid stainless steel appliances, Omega custom cabinetry, granite countertops, tile backsplash, center island, pantries, trash compactor, and hardwood flooring. Main-level primary suite includes heated bathroom floors and direct access to the rear deck overlooking the peaceful wooded setting. Additional features include two laundry rooms, upper-level loft area, Jack & Jill bathroom, and two gas fireplaces. Outdoor living truly sets this property apart with extensive landscaping, covered front porch, lower-level covered concrete patio, fenced pool area, chicken coop, storage shed, paved front walkway, expanded fencing, and updated Trex deck stairs, handrails, and railings. Major updates include new roof and cupola 2026 with transferable 21-year warranty through Modern Renovations (buyer must transfer within 60 days of closing), main-level HVAC and basement heat pump replaced 2024, pool pump replaced 2025, septic pumped 2024, septic pump replaced 2020, and gas water heater 2019. New garage door openers, w/battery back up. Most windows, doors, and Masonite siding have also been replaced. Pool area was renovated in 2016 with saltwater system, new liner and steps, plus the addition of the poolside deck and outdoor fireplace. New tile and sinks added in both upper-level bathrooms. Conveyances include 85” wide screen TV, universal weight machine, elliptical machine, 55” smart TV in workout room, Bose exterior speakers, pool furniture, robotic vacuums, pool cover/solar cover, work benches and cabinets, and two wall fans. Central vacuum conveys “as is.”

5 Beds ⋅ 5 Baths

Luxury custom home with a primary bedroom on the main floor. 5 partially wooded acres with an in-ground saltwater pool, upper-level Trex decks, screened porch, outdoor fireplace, and attached side-entry 4-car garage. Designed for entertaining and multi-generational living, this 5-bedroom, 4.5-bath home offers upscale finishes throughout plus a fully finished walkout basement with a second kitchen, additional living space, and gas fireplace. The gourmet kitchen features commercial-grade KitchenAid stainless steel appliances, Omega custom cabinetry, granite countertops, tile backsplash, center island, pantries, trash compactor, and hardwood flooring. Main-level primary suite includes heated bathroom floors and direct access to the rear deck overlooking the peaceful wooded setting. Additional features include two laundry rooms, upper-level loft area, Jack & Jill bathroom, and two gas fireplaces. Outdoor living truly sets this property apart with extensive landscaping, covered front porch, lower-level covered concrete patio, fenced pool area, chicken coop, storage shed, paved front walkway, expanded fencing, and updated Trex deck stairs, handrails, and railings. Major updates include new roof and cupola 2026 with transferable 21-year warranty through Modern Renovations (buyer must transfer within 60 days of closing), main-level HVAC and basement heat pump replaced 2024, pool pump replaced 2025, septic pumped 2024, septic pump replaced 2020, and gas water heater 2019. New garage door openers, w/battery back up. Most windows, doors, and Masonite siding have also been replaced. Pool area was renovated in 2016 with saltwater system, new liner and steps, plus the addition of the poolside deck and outdoor fireplace. New tile and sinks added in both upper-level bathrooms. Conveyances include 85” wide screen TV, universal weight machine, elliptical machine, 55” smart TV in workout room, Bose exterior speakers, pool furniture, robotic vacuums, pool cover/solar cover, work benches and cabinets, and two wall fans. Central vacuum conveys “as is.”

128 Babbs Run Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Realty FC.

$935,000

156,58 acres minutes from Winchester, VA! Opportunities like this are hard to find—expansive land with fields, woods, and a creek, ready for your vision of a farm, estate, or peaceful retreat. Approximately half of the property could be farmed. Prime land opportunity in the Winchester area featuring a desirable mix of open fields, mature wooded acreage, and a scenic creek running through the property. An existing home conveys and is being sold as-is, with the primary value in the land and its future potential. An additional perc site is currently being filed with the county, offering increased flexibility for building and development. This property is well-suited for builders, investors, or those looking to create a custom estate. With its blend of usable pasture and natural landscape, the property also presents an excellent opportunity to establish a working farm, a vineyard or create a charming farmette, with options for livestock and or horses. Ideal for those seeking privacy, recreational use, or a peaceful rural lifestyle. Conveniently located just 15 minutes from numerous shopping, dining, and entertainment options in historic Winchester, VA. Other destinations for outdoor activities include, only 15 minutes from golfing at Rock Harbor. Outdoor, 30 minutes to Cacapon State Park in West Virginia, offering extensive mountain biking trails, hiking, swimming, kayaking, fishing and camping. 2 hours to Canaan Valley/Timberline for skiing in WV and approximately 1 hour 15 minutes from Dulles International Airport—80 miles from Washington, DC, 1112 Stony Hill Rd., offers the perfect balance of seclusion and accessibility. **AGENT MUST ACCOMPANY BUYER ** MUST HAVE APPOINTMENT TO TOUR PROPERTY. LIVESTOCK ON PROPERTY CURRENTLY. PLEASE ENSURE THAT GATE IS CLOSED AFTER ENTERING AND LEAVING PROPERTY AS WELL AS ANY ELECTRIC FENCING. Professional photos and drone video to be added after 4/4. 24 hour notice required to see interior of home. Currently Tenant occupied. *Dog in the home" No drive-bys. Must have 4x4 capability to navigate road. OFFERS DUE NO LATER THAN 9PM 4/6/26. OWNER RESERVES RIGHT TO REVIEW ALL OFFERS AS RECEIVED.

3 Beds ⋅ 2 Baths

156,58 acres minutes from Winchester, VA! Opportunities like this are hard to find—expansive land with fields, woods, and a creek, ready for your vision of a farm, estate, or peaceful retreat. Approximately half of the property could be farmed. Prime land opportunity in the Winchester area featuring a desirable mix of open fields, mature wooded acreage, and a scenic creek running through the property. An existing home conveys and is being sold as-is, with the primary value in the land and its future potential. An additional perc site is currently being filed with the county, offering increased flexibility for building and development. This property is well-suited for builders, investors, or those looking to create a custom estate. With its blend of usable pasture and natural landscape, the property also presents an excellent opportunity to establish a working farm, a vineyard or create a charming farmette, with options for livestock and or horses. Ideal for those seeking privacy, recreational use, or a peaceful rural lifestyle. Conveniently located just 15 minutes from numerous shopping, dining, and entertainment options in historic Winchester, VA. Other destinations for outdoor activities include, only 15 minutes from golfing at Rock Harbor. Outdoor, 30 minutes to Cacapon State Park in West Virginia, offering extensive mountain biking trails, hiking, swimming, kayaking, fishing and camping. 2 hours to Canaan Valley/Timberline for skiing in WV and approximately 1 hour 15 minutes from Dulles International Airport—80 miles from Washington, DC, 1112 Stony Hill Rd., offers the perfect balance of seclusion and accessibility. **AGENT MUST ACCOMPANY BUYER ** MUST HAVE APPOINTMENT TO TOUR PROPERTY. LIVESTOCK ON PROPERTY CURRENTLY. PLEASE ENSURE THAT GATE IS CLOSED AFTER ENTERING AND LEAVING PROPERTY AS WELL AS ANY ELECTRIC FENCING. Professional photos and drone video to be added after 4/4. 24 hour notice required to see interior of home. Currently Tenant occupied. *Dog in the home" No drive-bys. Must have 4x4 capability to navigate road. OFFERS DUE NO LATER THAN 9PM 4/6/26. OWNER RESERVES RIGHT TO REVIEW ALL OFFERS AS RECEIVED.

1112 Stony Hill Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

$929,900

Very private community (2 five acre wooded lots) can not be seen from road. Close to town with wooded lots setting off of main road with private lane (TO BE PAVED UPON COMPLETION OF HOMES). This home boosts one level living with 3,100 sq. ft. of open floor plan with so many features others would call them upgrades! Brick front with cement siding on three sides. Large concrete front porch with concrete lead walk. No HOA. Builders upgrades: hardwood entire main floor (except baths and laundry to be tile), stained Early American HW. Covered/screened deck and attached open deck off back! Two double door walk out basement exits with patio across entire back. See this builders standard features.

3 Beds ⋅ 3 Baths

Very private community (2 five acre wooded lots) can not be seen from road. Close to town with wooded lots setting off of main road with private lane (TO BE PAVED UPON COMPLETION OF HOMES). This home boosts one level living with 3,100 sq. ft. of open floor plan with so many features others would call them upgrades! Brick front with cement siding on three sides. Large concrete front porch with concrete lead walk. No HOA. Builders upgrades: hardwood entire main floor (except baths and laundry to be tile), stained Early American HW. Covered/screened deck and attached open deck off back! Two double door walk out basement exits with patio across entire back. See this builders standard features.

125 Split Ridge Ln, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Realty ONE Group Old Towne.

$929,200

Bring your horses!! Nestled on a picturesque 7+ acre lot, this luxurious estate is within 5 minutes from downtown Winchester, offering the perfect blend of privacy, space, and convenience. This property includes a 2-stall barn with electricity and multiple paddocks! Opportunities like this are rare—enjoy the tranquility of country living while remaining in one of the area’s most desirable and accessible locations. Inside, hardwood floors flow throughout the home, beginning with a grand entrance and impressive foyer that sets the tone. The main level features a formal dining room, a private office with elegant French doors, and a spacious family room centered around a cozy gas fireplace. The kitchen is designed for both function and gathering, complete with granite countertops, a large peninsula, and a charming breakfast nook overlooking the property. The first-floor primary suite provides a true retreat, featuring French doors leading outside, a wet bar, two large walk-in closets, and a luxurious en-suite bath with dual vanities, a soaking tub, and a walk-in shower. Upstairs offers exceptional space and flexibility with 3 additional bedrooms and multiple flex spaces and storage options. One bedroom features a walk-in closet and full bath, making it the perfect guest suite. The other bedrooms all offer ample closet space and share a jack and jill bathroom. A light and bright flex room is highlighted by skylights. Another smaller room can be used for a second office or storage closet. A large bonus room over the garage offers an abundance of finished space. Enjoy beautiful sunsets and pasture views, with a barn complete with electricity, multiple fenced enclosures and plenty of yard space for entertaining friends and family. With expansive acreage, privacy, and a highly sought-after location so close to town, this property is a rare opportunity to own a beautiful estate without sacrificing convenience to amenities.

6 Beds ⋅ 4 Baths

Bring your horses!! Nestled on a picturesque 7+ acre lot, this luxurious estate is within 5 minutes from downtown Winchester, offering the perfect blend of privacy, space, and convenience. This property includes a 2-stall barn with electricity and multiple paddocks! Opportunities like this are rare—enjoy the tranquility of country living while remaining in one of the area’s most desirable and accessible locations. Inside, hardwood floors flow throughout the home, beginning with a grand entrance and impressive foyer that sets the tone. The main level features a formal dining room, a private office with elegant French doors, and a spacious family room centered around a cozy gas fireplace. The kitchen is designed for both function and gathering, complete with granite countertops, a large peninsula, and a charming breakfast nook overlooking the property. The first-floor primary suite provides a true retreat, featuring French doors leading outside, a wet bar, two large walk-in closets, and a luxurious en-suite bath with dual vanities, a soaking tub, and a walk-in shower. Upstairs offers exceptional space and flexibility with 3 additional bedrooms and multiple flex spaces and storage options. One bedroom features a walk-in closet and full bath, making it the perfect guest suite. The other bedrooms all offer ample closet space and share a jack and jill bathroom. A light and bright flex room is highlighted by skylights. Another smaller room can be used for a second office or storage closet. A large bonus room over the garage offers an abundance of finished space. Enjoy beautiful sunsets and pasture views, with a barn complete with electricity, multiple fenced enclosures and plenty of yard space for entertaining friends and family. With expansive acreage, privacy, and a highly sought-after location so close to town, this property is a rare opportunity to own a beautiful estate without sacrificing convenience to amenities.

240 Glendobbin Rd, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Non Subscribing Office.

$925,000

A PRIVATE CUSTOM-BUILT ESTATE SURROUNDED BY NATURE — WITH YOUR OWN RESORT-STYLE POOL! Set on an extraordinary 6.44 private acres, this exquisite custom-built residence offers nearly 4,700 square feet of beautifully finished living space across three levels, combining luxurious indoor living with an incredible outdoor setting. Tucked away among the trees, this is the kind of property where you can step outside, take a swim in your private in-ground pool, lounge poolside, enjoy the screened deck, gather around a campfire, play yard games, or simply sit beneath the stars and enjoy the peace and privacy of nature. Inside, the home is equally impressive. The main-level primary suite is a true retreat, featuring a vaulted ceiling, ceiling fan, fireplace, striking accent wall crafted from flooring, and direct access to the expansive screened deck. Two walk-in closets provide exceptional storage, while the spa-like primary bath features a double vanity, soaking tub with a mounted electric fireplace, and an oversized walk-in shower with dual shower heads and a built-in bench. A spacious main-level laundry room offers abundant cabinetry and shelving, while a second full bath with a walk-in shower adds convenience. The fifth main-level bedroom provides the perfect flexibility for a home office, study, or guest room. At the heart of the home, the gourmet kitchen opens seamlessly to the spectacular two-story family room, creating an ideal space for everyday living and entertaining. The kitchen features a large island with breakfast bar, high-end range with hood, gas cooking, backsplash extending to the ceiling, and a bright breakfast nook. The sun-filled family room showcases a dramatic two-story stone fireplace and opens directly onto the screened deck. And what a screened deck it is! Stretching nearly the entire length of the home, this expansive outdoor living space features two ceiling fans and overlooks the sprawling backyard and custom in-ground pool. Imagine morning coffee surrounded by the sounds of nature, summer evenings entertaining friends, or relaxing poolside without ever leaving the comfort of home. Retractable screen doors at both the front entry and garage entry add another thoughtful custom touch. Beautiful custom railings lead to the upper level, where you'll find three generously sized bedrooms, each with a ceiling fan. One bedroom offers direct access to a large bonus room that can easily serve as a craft room, playroom, additional storage, or whatever best fits your needs. A full upper-level bathroom includes a tub/shower combination. The finished lower level provides even more living and entertaining space with a large recreation room, another impressive stone fireplace, built-in shelving, and a fun "secret" closet tucked beneath the stairs. The rec room walks out to the rear patio, creating an easy connection to the incredible outdoor spaces. An additional unfinished room provides tremendous storage or workshop potential, with 10-foot ceilings offering exceptional versatility. Outside, the property continues to impress. A huge circular driveway provides an abundance of parking for family and guests and leads to the attached two-car garage. A custom-built shed provides ideal storage for pool equipment, lawn and yard equipment, a tractor, and more. With 6.44 acres to explore, there is room for outdoor games, campfires, gardening, stargazing, and creating memories for years to come. This is far more than a house — it is a private retreat, entertainer's dream, and everyday escape, offering the rare combination of custom luxury, expansive living space, a spectacular pool, and 6.44 acres of privacy and natural beauty. Come experience the setting, the craftsmanship, and the lifestyle for yourself.

5 Beds ⋅ 3 Baths

A PRIVATE CUSTOM-BUILT ESTATE SURROUNDED BY NATURE — WITH YOUR OWN RESORT-STYLE POOL! Set on an extraordinary 6.44 private acres, this exquisite custom-built residence offers nearly 4,700 square feet of beautifully finished living space across three levels, combining luxurious indoor living with an incredible outdoor setting. Tucked away among the trees, this is the kind of property where you can step outside, take a swim in your private in-ground pool, lounge poolside, enjoy the screened deck, gather around a campfire, play yard games, or simply sit beneath the stars and enjoy the peace and privacy of nature. Inside, the home is equally impressive. The main-level primary suite is a true retreat, featuring a vaulted ceiling, ceiling fan, fireplace, striking accent wall crafted from flooring, and direct access to the expansive screened deck. Two walk-in closets provide exceptional storage, while the spa-like primary bath features a double vanity, soaking tub with a mounted electric fireplace, and an oversized walk-in shower with dual shower heads and a built-in bench. A spacious main-level laundry room offers abundant cabinetry and shelving, while a second full bath with a walk-in shower adds convenience. The fifth main-level bedroom provides the perfect flexibility for a home office, study, or guest room. At the heart of the home, the gourmet kitchen opens seamlessly to the spectacular two-story family room, creating an ideal space for everyday living and entertaining. The kitchen features a large island with breakfast bar, high-end range with hood, gas cooking, backsplash extending to the ceiling, and a bright breakfast nook. The sun-filled family room showcases a dramatic two-story stone fireplace and opens directly onto the screened deck. And what a screened deck it is! Stretching nearly the entire length of the home, this expansive outdoor living space features two ceiling fans and overlooks the sprawling backyard and custom in-ground pool. Imagine morning coffee surrounded by the sounds of nature, summer evenings entertaining friends, or relaxing poolside without ever leaving the comfort of home. Retractable screen doors at both the front entry and garage entry add another thoughtful custom touch. Beautiful custom railings lead to the upper level, where you'll find three generously sized bedrooms, each with a ceiling fan. One bedroom offers direct access to a large bonus room that can easily serve as a craft room, playroom, additional storage, or whatever best fits your needs. A full upper-level bathroom includes a tub/shower combination. The finished lower level provides even more living and entertaining space with a large recreation room, another impressive stone fireplace, built-in shelving, and a fun "secret" closet tucked beneath the stairs. The rec room walks out to the rear patio, creating an easy connection to the incredible outdoor spaces. An additional unfinished room provides tremendous storage or workshop potential, with 10-foot ceilings offering exceptional versatility. Outside, the property continues to impress. A huge circular driveway provides an abundance of parking for family and guests and leads to the attached two-car garage. A custom-built shed provides ideal storage for pool equipment, lawn and yard equipment, a tractor, and more. With 6.44 acres to explore, there is room for outdoor games, campfires, gardening, stargazing, and creating memories for years to come. This is far more than a house — it is a private retreat, entertainer's dream, and everyday escape, offering the rare combination of custom luxury, expansive living space, a spectacular pool, and 6.44 acres of privacy and natural beauty. Come experience the setting, the craftsmanship, and the lifestyle for yourself.

218 Babbs Mountain Rd, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Realty ONE Group Old Towne.

$925,000

For comp purposes only.

5 Beds ⋅ 3 Baths

For comp purposes only.

413 N Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Colony Realty.

$919,000

Fully Leased Commercial Building, Multi Tenant, Excellent Condition! Located in Winchester City with outstanding commercial visibility and access. Almost 4800 SF. Fully modernized. Fully leased with three excellent credit tenants! NOI is $65K. Two long term tenants and one new lease. Great parking. Ideal 1031 investment. Priced below assessed value. Approx. 7% CAP.

47 W Jubal Early Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Oakcrest Commercial Real Estate.

$915,000

Nestled on an expansive 20.54-acre lot, this stunning ranch-style home, built in 2023, offers a harmonious blend of luxury and comfort. The exterior showcases a sophisticated combination of HardiPlank, masonry, and stone, creating a timeless appeal that invites you to explore the beauty within. Step inside to discover an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for both entertaining and everyday living. The gourmet kitchen is a chef's dream, featuring upgraded countertops, a spacious island, and stainless-steel appliances, including a built-in microwave, gas range, refrigerator and dishwasher. The adjacent dining area and family room, complete with a cozy gas/propane stone fireplace, create an inviting atmosphere for gatherings or quiet evenings at home. This residence home three well-appointed bedrooms, including a primary suite with a luxurious walk-in closet and an en-suite bathroom featuring a walk-in shower. There is also an additional large room that is currently an epic sewing room, but it could also function as an office, library, playroom, exercise or even a guest bedroom if needed. Thoughtful details such as recessed lighting, pocket doors, built-ins, and ceiling fans enhance the home's warmth and functionality. An attic with a fan provides comfort throughout the seasons. The main floor laundry adds convenience to your daily routine, while the expansive outdoor spaces including a full front porch and rear patio offer endless possibilities. Enjoy the tranquility of your partly wooded surroundings, perfect for nature enthusiasts or those seeking a private retreat. The cleared areas are ideal for outdoor activities, whether it's hunting, gardening, or simply enjoying the abundant wildlife and scenic vistas of your rolling, open and wooded views. With no restrictions, the potential for future enhancements and personalized uses are limitless. This home is not just a residence; it's a lifestyle. Experience the serenity of country living while being just a short drive from urban conveniences. Subdivision may be possible; confirm with the county.

3 Beds ⋅ 3 Baths

Nestled on an expansive 20.54-acre lot, this stunning ranch-style home, built in 2023, offers a harmonious blend of luxury and comfort. The exterior showcases a sophisticated combination of HardiPlank, masonry, and stone, creating a timeless appeal that invites you to explore the beauty within. Step inside to discover an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for both entertaining and everyday living. The gourmet kitchen is a chef's dream, featuring upgraded countertops, a spacious island, and stainless-steel appliances, including a built-in microwave, gas range, refrigerator and dishwasher. The adjacent dining area and family room, complete with a cozy gas/propane stone fireplace, create an inviting atmosphere for gatherings or quiet evenings at home. This residence home three well-appointed bedrooms, including a primary suite with a luxurious walk-in closet and an en-suite bathroom featuring a walk-in shower. There is also an additional large room that is currently an epic sewing room, but it could also function as an office, library, playroom, exercise or even a guest bedroom if needed. Thoughtful details such as recessed lighting, pocket doors, built-ins, and ceiling fans enhance the home's warmth and functionality. An attic with a fan provides comfort throughout the seasons. The main floor laundry adds convenience to your daily routine, while the expansive outdoor spaces including a full front porch and rear patio offer endless possibilities. Enjoy the tranquility of your partly wooded surroundings, perfect for nature enthusiasts or those seeking a private retreat. The cleared areas are ideal for outdoor activities, whether it's hunting, gardening, or simply enjoying the abundant wildlife and scenic vistas of your rolling, open and wooded views. With no restrictions, the potential for future enhancements and personalized uses are limitless. This home is not just a residence; it's a lifestyle. Experience the serenity of country living while being just a short drive from urban conveniences. Subdivision may be possible; confirm with the county.

3328 Millwood Pike, Winchester

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

Selling Office: RE/MAX Real Estate Connections.

$905,264

Main Level Living in Raven Pointe on one of 9 lots left! The ever-popular Tracey model with a side load 3-car garage. Home features a flexible floorpan that allows for maximum customization. Home features include large, open kitchen, vaulted ceilings in the living room (12'+), an adjacent sunroom, covered porch with Trex decking, tile showers in all baths and much more. This is a customizable plan and build. Buyers can choose any tile, appliances, cabinets, lighting they like. Basement is large with many finishing options available. Raven Pointe features very low HOA fees ($80 annually) and close proximity to Winchester, the Winchester Country Club and shopping areas (Costco a mile away). Currently, there are homes to walk and tour (already sold). Come see the difference from a custom builder.

4 Beds ⋅ 3 Baths

Main Level Living in Raven Pointe on one of 9 lots left! The ever-popular Tracey model with a side load 3-car garage. Home features a flexible floorpan that allows for maximum customization. Home features include large, open kitchen, vaulted ceilings in the living room (12'+), an adjacent sunroom, covered porch with Trex decking, tile showers in all baths and much more. This is a customizable plan and build. Buyers can choose any tile, appliances, cabinets, lighting they like. Basement is large with many finishing options available. Raven Pointe features very low HOA fees ($80 annually) and close proximity to Winchester, the Winchester Country Club and shopping areas (Costco a mile away). Currently, there are homes to walk and tour (already sold). Come see the difference from a custom builder.

219 Taggart Dr, Winchester

Listing courtesy of Merrifield Realty, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$900,000

Striking modern farmhouse-style home built in 2009, set on 15.14 private acres. Offering 2,475 finished square feet above grade plus 540 finished square feet on the lower level, for over 3,000 total finished square feet. This 3-bedroom, 4.5-bath home features two fireplaces, hardwood flooring, a heat pump with central air, and a composition gable roof. The wraparound covered porch adds inviting year-round outdoor living space, while the dramatic gable rooflines and tall accent windows give the home standout curb appeal. A partial basement offers additional storage or expansion potential. Room to roam, room to build, and room to breathe — all within reach of Winchester.

3 Beds ⋅ 5 Baths

Striking modern farmhouse-style home built in 2009, set on 15.14 private acres. Offering 2,475 finished square feet above grade plus 540 finished square feet on the lower level, for over 3,000 total finished square feet. This 3-bedroom, 4.5-bath home features two fireplaces, hardwood flooring, a heat pump with central air, and a composition gable roof. The wraparound covered porch adds inviting year-round outdoor living space, while the dramatic gable rooflines and tall accent windows give the home standout curb appeal. A partial basement offers additional storage or expansion potential. Room to roam, room to build, and room to breathe — all within reach of Winchester.

2630 Hunting Ridge Rd, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Realty ONE Group Old Towne.

$900,000

Welcome to this 11.41-acre mostly wooded property just minutes from town! This 2x6 custom-framed insulated log home with impressive 10-inch split logs offers the character of a true log home with added energy efficiency. Featuring 3 bedrooms and 3.5 baths, the home has been meticulously maintained and shows beautifully. The main level includes a spacious primary suite with private access to the TimberTech deck, overlooking peaceful wooded views. The family room offers cathedral ceilings and a striking stone fireplace, creating a warm, inviting atmosphere. The kitchen features hickory cabinetry, granite countertops, and generous prep space. A well-appointed main-level laundry room includes granite surfaces and ample cabinetry for storage and functionality. The finished lower level provides two additional bedrooms and bathrooms, radiant floor heat, a second wood-burning fireplace (piped for propane), a granite island/bar, and a mini refrigerator—ideal for guests, entertaining, or extended living arrangements. Extensive updates and maintenance include a heat pump approximately 5 years old, main boiler components replaced in 2020, water softener, septic pumped every three years, French drains, and gutter guards. Outdoor features include a paved walkway, paver patio, Timber Tech decking, and a 3-car garage. Road maintenance agreement is $500 annually. A rare opportunity to own acreage, privacy, and quality log construction just minutes from Winchester conveniences. The owner uses Xfinity for internet services. Check out our 3-D tour attached to this listing!

3 Beds ⋅ 4 Baths

Welcome to this 11.41-acre mostly wooded property just minutes from town! This 2x6 custom-framed insulated log home with impressive 10-inch split logs offers the character of a true log home with added energy efficiency. Featuring 3 bedrooms and 3.5 baths, the home has been meticulously maintained and shows beautifully. The main level includes a spacious primary suite with private access to the TimberTech deck, overlooking peaceful wooded views. The family room offers cathedral ceilings and a striking stone fireplace, creating a warm, inviting atmosphere. The kitchen features hickory cabinetry, granite countertops, and generous prep space. A well-appointed main-level laundry room includes granite surfaces and ample cabinetry for storage and functionality. The finished lower level provides two additional bedrooms and bathrooms, radiant floor heat, a second wood-burning fireplace (piped for propane), a granite island/bar, and a mini refrigerator—ideal for guests, entertaining, or extended living arrangements. Extensive updates and maintenance include a heat pump approximately 5 years old, main boiler components replaced in 2020, water softener, septic pumped every three years, French drains, and gutter guards. Outdoor features include a paved walkway, paver patio, Timber Tech decking, and a 3-car garage. Road maintenance agreement is $500 annually. A rare opportunity to own acreage, privacy, and quality log construction just minutes from Winchester conveniences. The owner uses Xfinity for internet services. Check out our 3-D tour attached to this listing!

181 Signal Ridge Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Compass.

$900,000

Stunning 4 Bed / 3.5 Bath Chalet on 3.26 Acres with Over 6,300 Sq Ft — Minutes from Winchester This exceptional chalet-style home offers over 6,300 sq ft of living space on a private, partially wooded 3.26-acre lot just minutes from Winchester. Designed to capture mountain views, the home features soaring cathedral ceilings, a striking stone fireplace, and walls of windows that flood the great room with natural light. A second-story loft with a family room overlooks the main-level great room, adding to the home’s open, airy feel. Hardwood floors run throughout the main level, which opens to a spacious wrap-around deck—perfect for entertaining or simply enjoying the views. The primary suite is also on the main level and features a jetted tub and a walk-in closet. A main-level laundry room adds everyday convenience. The gourmet kitchen offers an island, breakfast bar, new dishwasher, and microwave, while the main-level den includes a built-in bench with extra storage. The finished walk-out basement is ideal for guests or multi-generational living, complete with a wet bar, kitchenette, second entrance, sink, and refrigerator. You’ll also find a spacious main-level workshop with shiplap walls and a large sink—perfect for hobbies or projects. Additional features include an oversized 2-car garage, Culligan water softener, pressure tank, sump pump with new grinder pump, Aqua PEX plumbing, solid oak doors on the main level, 2x6 exterior walls with extra insulation, and durable HardiePlank siding. The chimney has been regularly maintained. Recent updates include: Roof (2024), Main-level HVAC (2025), Septic pumped (2025), Brine tank replaced (2025), Back deck (2022), Gazebo (2025), Microwave (2025), Whole house painted (2025), Fresh landscaping (2025), Shed (2025), & Washer & dryer (2025). This is a rare opportunity to own a spacious, well-maintained mountain-view home with privacy, quality construction, and extensive updates—just a short drive from Winchester. Check out our 3-D Tour link attached to the listing!

4 Beds ⋅ 4 Baths

Stunning 4 Bed / 3.5 Bath Chalet on 3.26 Acres with Over 6,300 Sq Ft — Minutes from Winchester This exceptional chalet-style home offers over 6,300 sq ft of living space on a private, partially wooded 3.26-acre lot just minutes from Winchester. Designed to capture mountain views, the home features soaring cathedral ceilings, a striking stone fireplace, and walls of windows that flood the great room with natural light. A second-story loft with a family room overlooks the main-level great room, adding to the home’s open, airy feel. Hardwood floors run throughout the main level, which opens to a spacious wrap-around deck—perfect for entertaining or simply enjoying the views. The primary suite is also on the main level and features a jetted tub and a walk-in closet. A main-level laundry room adds everyday convenience. The gourmet kitchen offers an island, breakfast bar, new dishwasher, and microwave, while the main-level den includes a built-in bench with extra storage. The finished walk-out basement is ideal for guests or multi-generational living, complete with a wet bar, kitchenette, second entrance, sink, and refrigerator. You’ll also find a spacious main-level workshop with shiplap walls and a large sink—perfect for hobbies or projects. Additional features include an oversized 2-car garage, Culligan water softener, pressure tank, sump pump with new grinder pump, Aqua PEX plumbing, solid oak doors on the main level, 2x6 exterior walls with extra insulation, and durable HardiePlank siding. The chimney has been regularly maintained. Recent updates include: Roof (2024), Main-level HVAC (2025), Septic pumped (2025), Brine tank replaced (2025), Back deck (2022), Gazebo (2025), Microwave (2025), Whole house painted (2025), Fresh landscaping (2025), Shed (2025), & Washer & dryer (2025). This is a rare opportunity to own a spacious, well-maintained mountain-view home with privacy, quality construction, and extensive updates—just a short drive from Winchester. Check out our 3-D Tour link attached to the listing!

189 Babbs Mountain Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: RE/MAX Real Estate Connections.

$900,000

Extensively renovated in 2024 and privately situated on a peaceful 2.7-acre cul-de-sac lot, this stunning brick home offers a rare opportunity to own acreage, privacy, and high-end upgrades just minutes from Winchester amenities. Surrounded by mature trees and free from HOA restrictions, the property delivers an estate-like setting with modern finishes throughout. The entire home has been thoughtfully updated with new flooring throughout, including herringbone-pattern hardwoods and tile, fresh paint on walls, ceilings, and trim, upgraded interior doors and hardware, and added recessed lighting for a clean, modern feel. The welcoming entry features new railings, stair treads, and a custom carpet runner. The redesigned kitchen is a true centerpiece, showcasing new cabinetry and hardware (including mudroom storage), Café stainless steel appliances, quartz countertops, recessed lighting, and statement island pendant, ideal for everyday living and entertaining. The adjacent laundry room has been fully upgraded with new cabinetry, countertops, ceramic tile flooring, washer and dryer, and sink. Formal dining is enhanced by a chandelier and wall sconces, while the screened porch offers tiled flooring and a ceiling fan, perfect for enjoying the private wooded surroundings. A main-level office provides flexible work-from-home space. The updated powder room features porcelain tile flooring, vanity, mirror, and fixtures. Upstairs, the primary suite has been completely reimagined with a redesigned bathroom layout with a custom barn door entry and features a fully tiled walk-in shower, new floor and shower tile, double vanity, lighting fixtures, chandelier, and brick veneer accent wall. The primary bedroom includes updated lighting and custom closet shelving. A secondary full bath offers new ceramic tile flooring, double vanity, and fixtures, while the additional bedrooms feature new light fixtures and ceiling fans. A full unfinished basement presents a valuable opportunity for future expansion—ideal for additional living space, a home gym, media room, or guest suite—allowing buyers to customize the home to their needs and build equity over time. This property stands out for its exceptional renovation quality, land value, and long-term flexibility, offering privacy, modern comfort, and space that cannot be replicated in newer developments—a truly turnkey opportunity for buyers seeking upgraded living on acreage in a desirable Winchester location.

4 Beds ⋅ 3 Baths

Extensively renovated in 2024 and privately situated on a peaceful 2.7-acre cul-de-sac lot, this stunning brick home offers a rare opportunity to own acreage, privacy, and high-end upgrades just minutes from Winchester amenities. Surrounded by mature trees and free from HOA restrictions, the property delivers an estate-like setting with modern finishes throughout. The entire home has been thoughtfully updated with new flooring throughout, including herringbone-pattern hardwoods and tile, fresh paint on walls, ceilings, and trim, upgraded interior doors and hardware, and added recessed lighting for a clean, modern feel. The welcoming entry features new railings, stair treads, and a custom carpet runner. The redesigned kitchen is a true centerpiece, showcasing new cabinetry and hardware (including mudroom storage), Café stainless steel appliances, quartz countertops, recessed lighting, and statement island pendant, ideal for everyday living and entertaining. The adjacent laundry room has been fully upgraded with new cabinetry, countertops, ceramic tile flooring, washer and dryer, and sink. Formal dining is enhanced by a chandelier and wall sconces, while the screened porch offers tiled flooring and a ceiling fan, perfect for enjoying the private wooded surroundings. A main-level office provides flexible work-from-home space. The updated powder room features porcelain tile flooring, vanity, mirror, and fixtures. Upstairs, the primary suite has been completely reimagined with a redesigned bathroom layout with a custom barn door entry and features a fully tiled walk-in shower, new floor and shower tile, double vanity, lighting fixtures, chandelier, and brick veneer accent wall. The primary bedroom includes updated lighting and custom closet shelving. A secondary full bath offers new ceramic tile flooring, double vanity, and fixtures, while the additional bedrooms feature new light fixtures and ceiling fans. A full unfinished basement presents a valuable opportunity for future expansion—ideal for additional living space, a home gym, media room, or guest suite—allowing buyers to customize the home to their needs and build equity over time. This property stands out for its exceptional renovation quality, land value, and long-term flexibility, offering privacy, modern comfort, and space that cannot be replicated in newer developments—a truly turnkey opportunity for buyers seeking upgraded living on acreage in a desirable Winchester location.

247 Mcguire Rd, Winchester

Listing courtesy of Weichert Realtors - Blue Ribbon. Contact:

Selling Office: Fathom Realty.

$899,900

Privacy and beauty surround this gorgeous 5-bedroom, 4.5-bath home on three finished levels. You’ll love the open layout, generous storage, and spacious finished basement perfect for movie nights or guests. Step outside to your private retreat — a deck and patio ideal for entertaining or simply enjoying the peaceful wooded setting. Oversized garage, great location (under 15 minutes to Winchester Medical Center, 10 minutes to Route 37). Additional 5 acres available to make 10 Acres of privacy for $899,900

5 Beds ⋅ 6 Baths

Privacy and beauty surround this gorgeous 5-bedroom, 4.5-bath home on three finished levels. You’ll love the open layout, generous storage, and spacious finished basement perfect for movie nights or guests. Step outside to your private retreat — a deck and patio ideal for entertaining or simply enjoying the peaceful wooded setting. Oversized garage, great location (under 15 minutes to Winchester Medical Center, 10 minutes to Route 37). Additional 5 acres available to make 10 Acres of privacy for $899,900

280 Graystone Ln, Winchester

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

Selling Office: ERA Oakcrest Realty, Inc..

$899,900

Very private community (2 five acre wooded lots) can not be seen from road. Close to town with wooded lots setting off of main road with private lane (TO BE PAVED UPON COMPLETION OF HOMES). This home boosts one level living with 3,100 sq. ft. of open floor plan with so many features others would call them upgrades! Brick front with cement siding on three sides. Large concrete front porch with concrete lead walk. No HOA. Builders upgrades: hardwood entire main floor (except baths and laundry to be tile), stained Early American HW. Covered/screened deck and attached open deck off back! Two double door walk out basement exits with patio across entire back. See this builders standard features.

3 Beds ⋅ 3 Baths

Very private community (2 five acre wooded lots) can not be seen from road. Close to town with wooded lots setting off of main road with private lane (TO BE PAVED UPON COMPLETION OF HOMES). This home boosts one level living with 3,100 sq. ft. of open floor plan with so many features others would call them upgrades! Brick front with cement siding on three sides. Large concrete front porch with concrete lead walk. No HOA. Builders upgrades: hardwood entire main floor (except baths and laundry to be tile), stained Early American HW. Covered/screened deck and attached open deck off back! Two double door walk out basement exits with patio across entire back. See this builders standard features.

115 Split Ridge Ln, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$890,000

**All offers due 4/15/2026 12:00pm** Tucked away on a quiet drive in Winchester, VA, this stunning Colonial-style home blends timeless charm with modern comfort on over 18 acres of serene, private land. Perfect for anyone seeking peace, space, and a true connection to nature, this property offers an exceptional lifestyle both inside and out. Step inside to a warm, inviting interior featuring rich hardwood floors on the main level and brand-new carpeting throughout the upper level. The open foyer is flanked by a private office and a formal living room, creating an elegant first impression. The heart of the home is the spacious, country-style kitchen, complete with: center island for culinary creativity and generous table space for casual dining. Step down into the grand great room and sunroom. The expansive great room features a raised-hearth brick fireplace perfect for cozy evenings and the sunroom shows off the picturesque views. A formal dining room connects effortlessly to the formal living room, offering an ideal layout for gatherings and celebrations. On the upper level, the luxurious primary suite offers a walk-in closet and a spa-like bath with a jetted tub and walk-in shower. Additional bedrooms are generously sized, providing comfort and room for all. The unfinished walk-up basement offers endless potential, already equipped with a brick fireplace for a future recreation or relaxation space. For horse lovers, this property is a rare find. It includes: 2 fenced pastures, 2 run-in sheds, 2 troughs and ample acreage for riding, grazing, or expansion. The level, private lot is ideal for gardening, outdoor entertaining, or simply enjoying the sweeping views of the surrounding pastureland. A charming wrap-around porch invites you to savor morning coffee or unwind at sunset. This home is more than a residence—it’s a retreat. Enjoy the tranquility of country living while remaining just a short drive from local amenities. With space, privacy, and endless possibilities, this remarkable property offers a lifestyle that feels like a getaway every day. Don't delay to schedule your private showing of this remarkable property. Please NOTE: the entrance way from Airport Rd. is a blind entrance, it is safer to enter via Sorrel Ln. Follow the directionals....see you there.

1 Baths

**All offers due 4/15/2026 12:00pm** Tucked away on a quiet drive in Winchester, VA, this stunning Colonial-style home blends timeless charm with modern comfort on over 18 acres of serene, private land. Perfect for anyone seeking peace, space, and a true connection to nature, this property offers an exceptional lifestyle both inside and out. Step inside to a warm, inviting interior featuring rich hardwood floors on the main level and brand-new carpeting throughout the upper level. The open foyer is flanked by a private office and a formal living room, creating an elegant first impression. The heart of the home is the spacious, country-style kitchen, complete with: center island for culinary creativity and generous table space for casual dining. Step down into the grand great room and sunroom. The expansive great room features a raised-hearth brick fireplace perfect for cozy evenings and the sunroom shows off the picturesque views. A formal dining room connects effortlessly to the formal living room, offering an ideal layout for gatherings and celebrations. On the upper level, the luxurious primary suite offers a walk-in closet and a spa-like bath with a jetted tub and walk-in shower. Additional bedrooms are generously sized, providing comfort and room for all. The unfinished walk-up basement offers endless potential, already equipped with a brick fireplace for a future recreation or relaxation space. For horse lovers, this property is a rare find. It includes: 2 fenced pastures, 2 run-in sheds, 2 troughs and ample acreage for riding, grazing, or expansion. The level, private lot is ideal for gardening, outdoor entertaining, or simply enjoying the sweeping views of the surrounding pastureland. A charming wrap-around porch invites you to savor morning coffee or unwind at sunset. This home is more than a residence—it’s a retreat. Enjoy the tranquility of country living while remaining just a short drive from local amenities. With space, privacy, and endless possibilities, this remarkable property offers a lifestyle that feels like a getaway every day. Don't delay to schedule your private showing of this remarkable property. Please NOTE: the entrance way from Airport Rd. is a blind entrance, it is safer to enter via Sorrel Ln. Follow the directionals....see you there.

1681 Airport Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Coldwell Banker Premier.

$890,000

Welcome home to a perfect blend of space, serenity, and style. This exceptional property offers 5 private acres of rolling land, partially fenced and backing to mature woods, creating your own personal retreat just minutes from historic downtown Winchester, Valley Health Medical Center, local wineries, and commuter routes. Step inside to a bright and welcoming open floor plan, where gatherings come naturally. The heart of the home is a huge gourmet kitchen, featuring gleaming quartz countertops and seamless flow into a cheerful sunroom and a sprawling composite deck—ideal for everyday living and entertaining. The main level is thoughtfully designed for comfort and convenience, featuring a cozy family room with a coffered ceiling and a striking stone fireplace, a private office/den, and a main-floor bedroom with its own ensuite bath—perfect for guests or multi-generational living. Upstairs, escape to your spacious primary suite, a true sanctuary featuring a spa-like bathroom with a freestanding tub, a separate shower, dual vanities, and an impressively massive walk-in closet. Two additional bedrooms enjoy the privacy of their own ensuites—one includes a flexible bonus space for an office, nursery, or sitting area. A fourth bedroom and a hall bath complete this level. The finished lower level is your entertainment haven, complete with a large, versatile room ready to become your home gym, rec room, theater, or more—the possibilities are endless. A full bath and ample storage complete this flexible space. Don’t miss your opportunity to make this peaceful, well-appointed property your new home. Schedule your private Tour today!

5 Beds ⋅ 7 Baths

Welcome home to a perfect blend of space, serenity, and style. This exceptional property offers 5 private acres of rolling land, partially fenced and backing to mature woods, creating your own personal retreat just minutes from historic downtown Winchester, Valley Health Medical Center, local wineries, and commuter routes. Step inside to a bright and welcoming open floor plan, where gatherings come naturally. The heart of the home is a huge gourmet kitchen, featuring gleaming quartz countertops and seamless flow into a cheerful sunroom and a sprawling composite deck—ideal for everyday living and entertaining. The main level is thoughtfully designed for comfort and convenience, featuring a cozy family room with a coffered ceiling and a striking stone fireplace, a private office/den, and a main-floor bedroom with its own ensuite bath—perfect for guests or multi-generational living. Upstairs, escape to your spacious primary suite, a true sanctuary featuring a spa-like bathroom with a freestanding tub, a separate shower, dual vanities, and an impressively massive walk-in closet. Two additional bedrooms enjoy the privacy of their own ensuites—one includes a flexible bonus space for an office, nursery, or sitting area. A fourth bedroom and a hall bath complete this level. The finished lower level is your entertainment haven, complete with a large, versatile room ready to become your home gym, rec room, theater, or more—the possibilities are endless. A full bath and ample storage complete this flexible space. Don’t miss your opportunity to make this peaceful, well-appointed property your new home. Schedule your private Tour today!

254 Whistlewood Ln, Winchester

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

Selling Office: River Fox Realty, LLC.

$890,000

Experience exceptional living in this stunning Colonial set on 5 partially wooded acres, offering beautiful mountain and meadow views. This home provides the perfect blend of privacy and convenience—tucked away in a peaceful setting yet just minutes from town amenities and Winchester Medical Center. Inside, the spacious open floor plan includes two primary suites, ideal for multi-generational living or added flexibility for guests. The layout flows effortlessly into the outdoor retreat, where a heated in-ground pool and spa with custom stamped concrete coping create the perfect space for relaxation and entertaining. Car enthusiasts and hobbyists will appreciate the 2-car attached garage along with an impressive 4-car detached garage, providing abundant space for vehicles, equipment, or workshop needs. The fully finished basement adds even more versatility, offering an additional bedroom, full bathroom, and generous living area that works well for guests, recreation, or a home office setup. With its combination of serene acreage, thoughtful features, and incredible indoor and outdoor living spaces, this property stands out as a truly exceptional opportunity.

6 Beds ⋅ 5 Baths

Experience exceptional living in this stunning Colonial set on 5 partially wooded acres, offering beautiful mountain and meadow views. This home provides the perfect blend of privacy and convenience—tucked away in a peaceful setting yet just minutes from town amenities and Winchester Medical Center. Inside, the spacious open floor plan includes two primary suites, ideal for multi-generational living or added flexibility for guests. The layout flows effortlessly into the outdoor retreat, where a heated in-ground pool and spa with custom stamped concrete coping create the perfect space for relaxation and entertaining. Car enthusiasts and hobbyists will appreciate the 2-car attached garage along with an impressive 4-car detached garage, providing abundant space for vehicles, equipment, or workshop needs. The fully finished basement adds even more versatility, offering an additional bedroom, full bathroom, and generous living area that works well for guests, recreation, or a home office setup. With its combination of serene acreage, thoughtful features, and incredible indoor and outdoor living spaces, this property stands out as a truly exceptional opportunity.

229 Soldiers Rest Ln, Winchester

Listing courtesy of Preslee Real Estate. Contact:

Selling Office: RE/MAX Roots.

$890,000

Carrington Homes Model Home for Sale. This stunning 5-bedroom, 4.5-bathroom home with Main Level Bedroom, built in 2025. Nestled on 2.66 acres, this residence offers a serene view of lush trees and woods, creating a peaceful backdrop for your everyday life. The heart of the home features a gourmet kitchen equipped with ENERGY STAR stainless steel appliances, including a double oven and built-in microwave, perfect for culinary enthusiasts. Enjoy the convenience of an upper-floor laundry and a spacious, fully finished basement with walkout stairs, ideal for entertaining or relaxation. Step outside to a beautifully designed deck, perfect for al fresco dining or morning coffee amidst nature. The property boasts a three-car garage and an asphalt driveway, ensuring ample parking for guests. With energy-efficient windows and security system, this home combines comfort with modern convenience. Experience an exclusive lifestyle where luxury meets tranquility.

5 Beds ⋅ 5 Baths

Carrington Homes Model Home for Sale. This stunning 5-bedroom, 4.5-bathroom home with Main Level Bedroom, built in 2025. Nestled on 2.66 acres, this residence offers a serene view of lush trees and woods, creating a peaceful backdrop for your everyday life. The heart of the home features a gourmet kitchen equipped with ENERGY STAR stainless steel appliances, including a double oven and built-in microwave, perfect for culinary enthusiasts. Enjoy the convenience of an upper-floor laundry and a spacious, fully finished basement with walkout stairs, ideal for entertaining or relaxation. Step outside to a beautifully designed deck, perfect for al fresco dining or morning coffee amidst nature. The property boasts a three-car garage and an asphalt driveway, ensuring ample parking for guests. With energy-efficient windows and security system, this home combines comfort with modern convenience. Experience an exclusive lifestyle where luxury meets tranquility.

206 Covey Ln, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Hunt Country Sotheby's International Realty.

$879,000

Another quality home crafted by KEE Construction, located just off Cedar Creek Grade in the Shenandoah Valley and just minutes from Winchester City. Situated on 5.11 picturesque acres in a peaceful rural setting in the heart of the Shenandoah Valley, this modern farmhouse-style home with craftsman influences offers the perfect blend of refined craftsmanship and comfortable country living. Featuring 2,400 square feet of thoughtfully designed living space, this custom-built home includes 3 spacious bedrooms, 2 1/2 baths, a dedicated office, and an open-concept great room filled with natural light.The striking exterior showcases dark vertical siding, warm wood accents, and inviting covered entry details that create exceptional curb appeal. Inside, you’ll find rich flooring, custom built-ins, floating wood shelves, and a cozy fireplace that anchors the heart of the home. A stunning kitchen with quality finishes flows seamlessly into the main living and dining areas, ideal for entertaining or everyday living. The unfinished basement provides endless possibilities for future expansion, recreation space, or storage. Enjoy quiet mornings and relaxing evenings from the covered patio overlooking the expansive property, while the attached 2-car garage adds everyday convenience. Adding to the property’s peaceful setting and scenic beauty, the land directly across the road is protected by a conservation easement, helping preserve the surrounding open space, natural landscape, and rural character for years to come. Click on upper left hand corner to view the virtual tour.

3 Beds ⋅ 3 Baths

Another quality home crafted by KEE Construction, located just off Cedar Creek Grade in the Shenandoah Valley and just minutes from Winchester City. Situated on 5.11 picturesque acres in a peaceful rural setting in the heart of the Shenandoah Valley, this modern farmhouse-style home with craftsman influences offers the perfect blend of refined craftsmanship and comfortable country living. Featuring 2,400 square feet of thoughtfully designed living space, this custom-built home includes 3 spacious bedrooms, 2 1/2 baths, a dedicated office, and an open-concept great room filled with natural light.The striking exterior showcases dark vertical siding, warm wood accents, and inviting covered entry details that create exceptional curb appeal. Inside, you’ll find rich flooring, custom built-ins, floating wood shelves, and a cozy fireplace that anchors the heart of the home. A stunning kitchen with quality finishes flows seamlessly into the main living and dining areas, ideal for entertaining or everyday living. The unfinished basement provides endless possibilities for future expansion, recreation space, or storage. Enjoy quiet mornings and relaxing evenings from the covered patio overlooking the expansive property, while the attached 2-car garage adds everyday convenience. Adding to the property’s peaceful setting and scenic beauty, the land directly across the road is protected by a conservation easement, helping preserve the surrounding open space, natural landscape, and rural character for years to come. Click on upper left hand corner to view the virtual tour.

122 Broomsedge, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

Selling Office: Coldwell Banker Premier.

$875,000

4 Beds ⋅ 3 Baths

517 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Colony Realty.

$862,500

14K SF Warehouse and Office Building for Sale, Winchester City, with Great Parking! Excellent, turn key condition property, ready for immediate occupancy! All block and masonry building, fully air conditioned (including warehouse), all mechanicals, electric, and plumbing in good condition! 1st floor consists of 5K SF of warehouse, 2K SF of finished open offices with kitchenette. 2nd floor is 7K of individual offices, reception area, and 2nd kitchenette. Warehouse, 1st floor offices, and 2nd floor offices, all have separate restrooms (ADA on 1st floor). Property comes with two private parking lots offering over 30+ parking spaces! Although the property has never flooded, financing may require flood insurance. We have already secured an excellent quote for only $3,395 per year. This is an EXCELLECT DEAL for under $72 PSF! CM1 zoning allows for contractors offices, church, daycare, fitness facility, wholesale business, light manufacturing/warehousing. One tenant occupies small, secured portion of building through 2026 offering $1275+/month income. Contact Agent today to schedule a showing!

225 E Pall Mall St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Long & Foster Real Estate, Inc..