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Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll find a practical and inviting layout featuring 3 bedrooms, 1.5 bathrooms, a spacious kitchen, separate living and dining areas, main-level laundry, and additional storage space. Recent updates add extra peace of mind, including an HVAC system fully serviced in 2020 (serviced condenser unit 2026) and a roof recoated in 2021. Outside, the home offers valuable city-living features, including off-street parking and usable outdoor space for relaxing, gardening, pets, or entertaining. The surrounding streetscape is also seeing meaningful improvements, with the street being repaved, sidewalks redone, and new trees expected to be planted along the street. Whether you are searching for a primary residence, a Winchester-area home base, or a potential investment property, this home offers a strong combination of location, utility, and opportunity in an established Winchester neighborhood with quick access to major roadways and the surrounding Shenandoah Valley. Seller offering up to $2,500 towards painting with acceptable offer.

3 Beds ⋅ 2 Baths

Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll find a practical and inviting layout featuring 3 bedrooms, 1.5 bathrooms, a spacious kitchen, separate living and dining areas, main-level laundry, and additional storage space. Recent updates add extra peace of mind, including an HVAC system fully serviced in 2020 (serviced condenser unit 2026) and a roof recoated in 2021. Outside, the home offers valuable city-living features, including off-street parking and usable outdoor space for relaxing, gardening, pets, or entertaining. The surrounding streetscape is also seeing meaningful improvements, with the street being repaved, sidewalks redone, and new trees expected to be planted along the street. Whether you are searching for a primary residence, a Winchester-area home base, or a potential investment property, this home offers a strong combination of location, utility, and opportunity in an established Winchester neighborhood with quick access to major roadways and the surrounding Shenandoah Valley. Seller offering up to $2,500 towards painting with acceptable offer.

307 E Piccadilly St, Winchester

Listing courtesy of HoneyWay. Contact:

$2,200,000

OakCrest Commercial is pleased to present the opportunity to acquire an industrial property located at 205 Brick Kiln Road in Winchester, Virginia. The property consists of approximately 24,753 ± square feet situated on 1.2 acres and benefits from rare M-2 zoning near the Winchester City/Frederick County line. The asset is offered for sale at $2,200,000. The building is configured into three suites totaling approximately 24,753 ± SF, with one suite currently vacant. The available suite comprises approximately 11,600 ± SF and features a functional industrial/flex layout, including approximately 1,800 ± SF of office/mezzanine and 9,800 ± SF of warehouse space. The space includes loading, 3-phase power, and on-site parking, making it well suited for contractor, service, light production, or distribution users. The property currently generates $92,499.96 in-place NOI, reflecting income from the two occupied suites. The vacant suite is not contributing income at this time but represents a near-term lease-up opportunity. Upon stabilization, assuming lease-up at the current asking rent of $8,691 per month on a triple net basis, the property is projected to generate $196,791.96 in NOI. This offering presents an opportunity to acquire an asset with current cash flow and meaningful upside through lease-up, with flexibility for both investors and potential owner-users.

205 Brick Kiln Rd, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$374,900

This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door. The home looks bright and beautiful from the inside and out. The bathrooms have also gotten a modern makeover, complete with touch mirrors that add a touch of luxury. This one's a must-see!

3 Beds ⋅ 2 Baths

This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door. The home looks bright and beautiful from the inside and out. The bathrooms have also gotten a modern makeover, complete with touch mirrors that add a touch of luxury. This one's a must-see!

711 E Cork St, Winchester

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

$499,990

This stunning twin/semi‑detached home is ready for move in and located within the desirable 55+ gated community, Hiatt Pointe at Snowden Bridge. Designed for effortless main‑level living, the home features both a primary and secondary bedroom on the first floor—perfect for comfort and convenience. An open floor plan seamlessly connects the family room and kitchen, creating an inviting space ideal for both entertaining and quiet evenings at home. The kitchen shines with a spacious island, gourmet stainless steel appliances, white cabinets and elegant quartz countertops. Thoughtful design continues throughout, with abundant natural light and modern finishes. The second level offers a private third bedroom and a full bath, ideal for guests or additional living space. At the rear of the home, relax and unwind on the serene screened‑in porch. Residents enjoy exceptional community amenities, including a sparkling outdoor pool, fitness center, and tennis courts—all within a secure, gated setting. Experience a lifestyle centered on comfort, connection, and convenience at Hiatt Pointe. Your dream home awaits. Ask about Builder incentives!

3 Beds ⋅ 3 Baths

This stunning twin/semi‑detached home is ready for move in and located within the desirable 55+ gated community, Hiatt Pointe at Snowden Bridge. Designed for effortless main‑level living, the home features both a primary and secondary bedroom on the first floor—perfect for comfort and convenience. An open floor plan seamlessly connects the family room and kitchen, creating an inviting space ideal for both entertaining and quiet evenings at home. The kitchen shines with a spacious island, gourmet stainless steel appliances, white cabinets and elegant quartz countertops. Thoughtful design continues throughout, with abundant natural light and modern finishes. The second level offers a private third bedroom and a full bath, ideal for guests or additional living space. At the rear of the home, relax and unwind on the serene screened‑in porch. Residents enjoy exceptional community amenities, including a sparkling outdoor pool, fitness center, and tennis courts—all within a secure, gated setting. Experience a lifestyle centered on comfort, connection, and convenience at Hiatt Pointe. Your dream home awaits. Ask about Builder incentives!

108 Zinnia Ln, Winchester

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

$384,990

Move‑in ready and designed for the life you want to live. Enjoy effortless main‑level living in Hiatt Pointe at Snowden Bridge, a gated 55+ active adult community where comfort meets connection. This low‑maintenance villa offers a serene primary suite and laundry on the entry level, a screened rear porch for relaxing mornings and evenings, and a one‑car garage for everyday convenience. Upstairs, two generous bedrooms with walk‑in closets, a full bath, and a dedicated office provide the perfect space for guests, hobbies, or quiet pursuits. The heart of the home is a stylish kitchen with quartz countertops, stainless steel appliances, and elegant cabinetry—ideal for casual meals or entertaining. Step outside your door to enjoy resort‑style amenities including pickleball and bocce courts, a clubhouse, fitness and yoga studios, outdoor kitchen, pool, and hot tub. Snow removal, trash, and recycling are all included—so you can spend more time enjoying life, not maintaining it. Ask about builder incentives today!

3 Beds ⋅ 3 Baths

Move‑in ready and designed for the life you want to live. Enjoy effortless main‑level living in Hiatt Pointe at Snowden Bridge, a gated 55+ active adult community where comfort meets connection. This low‑maintenance villa offers a serene primary suite and laundry on the entry level, a screened rear porch for relaxing mornings and evenings, and a one‑car garage for everyday convenience. Upstairs, two generous bedrooms with walk‑in closets, a full bath, and a dedicated office provide the perfect space for guests, hobbies, or quiet pursuits. The heart of the home is a stylish kitchen with quartz countertops, stainless steel appliances, and elegant cabinetry—ideal for casual meals or entertaining. Step outside your door to enjoy resort‑style amenities including pickleball and bocce courts, a clubhouse, fitness and yoga studios, outdoor kitchen, pool, and hot tub. Snow removal, trash, and recycling are all included—so you can spend more time enjoying life, not maintaining it. Ask about builder incentives today!

111 Heirloom Way, Winchester

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

$199,900

Searching for the ideal place to build your dream home? This awesome 5.39 acre parcel delivers stunning views and a convenient location just minutes from town. Situated right off Rt 50 with easy access to Rt 37 and Interstate 81, you’ll be close to gas stations, restaurants, shopping, the hospital, and so much more—offering the perfect blend of peaceful country living and everyday convenience. The seller has completed the perc test and the 4 bedroom approved cert letter is uploaded in the documents!

Tbd (0) Cather Lane, Winchester

Listing courtesy of Preslee Real Estate. Contact:

$374,990

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

3 Beds ⋅ 3 Baths

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

105 Heirloom Way, Winchester

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

$131,500

Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting. A charming pond adds to the beauty and character of this land. Stellar views of the surrounding countryside are attainable with some tree clearing. This property features mildly sloping topography and a wet weather stream. Remote, fully wooded, and zoned Rural Areas (RA). No covenants, no restrictions, and no HOA! Enjoy hiking, camping, and recreation of all types on this land. A short drive from all the amenities and attractions Winchester has to offer. ***Additional adjoining acreage available for purchase. See aerials for details.***

Hodges, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$94,050

Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting. A charming pond adds to the beauty and character of this land. Stellar views of the surrounding countryside are attainable with some tree clearing. This property features mildly sloping topography and a wet weather stream. Remote, fully wooded, and zoned Rural Areas (RA). No covenants, no restrictions, and no HOA! Enjoy hiking, camping, and recreation of all types on this land. A short drive from all the amenities and attractions Winchester has to offer. ***Additional adjoining acreage available for purchase. See aerials for details.***

Hodges, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$89,550

Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting. Stellar views of the surrounding countryside are attainable with some tree clearing. This property features mildly sloping topography and a wet weather stream. Remote, fully wooded, and zoned Rural Areas (RA). No covenants, no restrictions, and no HOA! Enjoy hiking, camping, and recreation of all types on this land. A short drive from all the amenities and attractions Winchester has to offer. ***Additional adjoining acreage available for purchase. See aerials for details.***

Hodges, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$599,950

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

446 N Loudoun St, Winchester

Listing courtesy of Homes By Owner, Inc.. Contact:

$599,950

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

5 Beds ⋅ 2 Baths

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

446 N Loudoun St, Winchester

Listing courtesy of Homes By Owner, Inc.. Contact:

$2,200,000

Set on 21.5 acres just minutes from downtown Winchester, this 5-bedroom home offers over 5,800 finished square feet with a blend of space, functionality, and outdoor living in a highly convenient location. Combining usable land, thoughtful improvements, and indoor and outdoor entertaining spaces, this property offers a rare opportunity close to town amenities. While a neighboring property's drive is visible in the distance, it is not shared and is not subject to any easement. The generous separation between homes offers the flexibility to further enhance privacy with fencing, landscaping, or a custom tree line while maintaining the property's open, expansive setting. The main living areas feature an open flow between the kitchen and living room, highlighted by a fireplace and a custom kitchen with Mennonite-built cabinetry, stainless steel appliances, gas cooking, and a generous pantry. A fully finished basement with a second fireplace provides additional space for recreation, guests, or multi-generational living. Outdoor living includes an in-ground pool with hot tub, a 16'x27' covered patio with outdoor kitchen featuring a sink, grill, and refrigerator, a 16'x12' pergola, outdoor fireplace, detached pool house, and an additional covered hot tub area. The property also features a private stocked pond and a 24'x36' barn equipped with two stalls, wash bay, tack room, second-story hay loft, hot/cold water, and electric, making it suitable for equestrian or hobby use. An 18'x20' wood shed with outdoor wood stove adds additional utility. Additional features include a 1,270 sq ft three-car garage with 10'x8' doors, propane heat on the main level, heat pump on the upper level, outdoor wood stove capable of heating the entire home, gas water heater, and a new water heater installed in 2026. Conveniently located within approximately 5 miles of downtown Winchester, enjoy nearby shopping, dining, entertainment, Jim Barnett Park, Trails at the Museum of the Shenandoah Valley, and Rose Hill Park within walking distance. Above-ground hot tub, propane tank, and outbuildings convey AS-IS. Washer and dryer do not convey. *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

5 Beds ⋅ 5 Baths

Set on 21.5 acres just minutes from downtown Winchester, this 5-bedroom home offers over 5,800 finished square feet with a blend of space, functionality, and outdoor living in a highly convenient location. Combining usable land, thoughtful improvements, and indoor and outdoor entertaining spaces, this property offers a rare opportunity close to town amenities. While a neighboring property's drive is visible in the distance, it is not shared and is not subject to any easement. The generous separation between homes offers the flexibility to further enhance privacy with fencing, landscaping, or a custom tree line while maintaining the property's open, expansive setting. The main living areas feature an open flow between the kitchen and living room, highlighted by a fireplace and a custom kitchen with Mennonite-built cabinetry, stainless steel appliances, gas cooking, and a generous pantry. A fully finished basement with a second fireplace provides additional space for recreation, guests, or multi-generational living. Outdoor living includes an in-ground pool with hot tub, a 16'x27' covered patio with outdoor kitchen featuring a sink, grill, and refrigerator, a 16'x12' pergola, outdoor fireplace, detached pool house, and an additional covered hot tub area. The property also features a private stocked pond and a 24'x36' barn equipped with two stalls, wash bay, tack room, second-story hay loft, hot/cold water, and electric, making it suitable for equestrian or hobby use. An 18'x20' wood shed with outdoor wood stove adds additional utility. Additional features include a 1,270 sq ft three-car garage with 10'x8' doors, propane heat on the main level, heat pump on the upper level, outdoor wood stove capable of heating the entire home, gas water heater, and a new water heater installed in 2026. Conveniently located within approximately 5 miles of downtown Winchester, enjoy nearby shopping, dining, entertainment, Jim Barnett Park, Trails at the Museum of the Shenandoah Valley, and Rose Hill Park within walking distance. Above-ground hot tub, propane tank, and outbuildings convey AS-IS. Washer and dryer do not convey. *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

2230 Jones Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$280,000

Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018. Motivated seller!!!

3 Beds ⋅ 3 Baths

Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018. Motivated seller!!!

115 S Purcell Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$799,000

Escape the ordinary and come home to space, privacy, and beautiful mountain views at 230 Conifer Lane! Built in 2018 and situated on 2.26 acres with no HOA, this impressive 4-bedroom, 3-bath home offers nearly 4,000 finished square feet and the peaceful setting you’ve been searching for—all just a short drive from Winchester. Step inside to an open, inviting floor plan designed for both everyday living and entertaining. A main-level bedroom and full bath provide wonderful flexibility for guests, a home office, or additional living space. One of the highlights of this property is the connection to the outdoors. Relax on the screened porch, take in the mountain and wooded views, and enjoy having over two acres to garden, entertain, play, or simply appreciate the privacy and breathing room that can be hard to find. The partially finished walkout lower level adds even more possibilities with space for recreation, a home gym, hobby area, office, or future expansion. An oversized garage provides additional parking and storage. And country living doesn’t mean giving up modern convenience. High-speed fiber-optic internet makes working from home and streaming easy, while the owned solar panels add another valuable feature to this already impressive property. If you’ve been searching for a newer home with acreage, privacy, views, flexible living space, and no HOA—without being too far from Winchester—230 Conifer Lane deserves a closer look. **AND NOW** SAVE UP TO $870/MONTH YOUR FIRST YEAR! Seller-Paid 2-1 Buydown Enjoy payments based on a rate 2% lower the first year and 1% lower the second year. *with acceptable offer** Seller pays the buydown. You enjoy the savings. Come experience the setting for yourself. This is more than a home—it’s room to breathe.

4 Beds ⋅ 3 Baths

Escape the ordinary and come home to space, privacy, and beautiful mountain views at 230 Conifer Lane! Built in 2018 and situated on 2.26 acres with no HOA, this impressive 4-bedroom, 3-bath home offers nearly 4,000 finished square feet and the peaceful setting you’ve been searching for—all just a short drive from Winchester. Step inside to an open, inviting floor plan designed for both everyday living and entertaining. A main-level bedroom and full bath provide wonderful flexibility for guests, a home office, or additional living space. One of the highlights of this property is the connection to the outdoors. Relax on the screened porch, take in the mountain and wooded views, and enjoy having over two acres to garden, entertain, play, or simply appreciate the privacy and breathing room that can be hard to find. The partially finished walkout lower level adds even more possibilities with space for recreation, a home gym, hobby area, office, or future expansion. An oversized garage provides additional parking and storage. And country living doesn’t mean giving up modern convenience. High-speed fiber-optic internet makes working from home and streaming easy, while the owned solar panels add another valuable feature to this already impressive property. If you’ve been searching for a newer home with acreage, privacy, views, flexible living space, and no HOA—without being too far from Winchester—230 Conifer Lane deserves a closer look. **AND NOW** SAVE UP TO $870/MONTH YOUR FIRST YEAR! Seller-Paid 2-1 Buydown Enjoy payments based on a rate 2% lower the first year and 1% lower the second year. *with acceptable offer** Seller pays the buydown. You enjoy the savings. Come experience the setting for yourself. This is more than a home—it’s room to breathe.

230 Conifer Ln, Winchester

Listing courtesy of Samson Properties. Contact:

$89,500

*Price Improvement* Discover the perfect blend of privacy and natural beauty with this 5.49-acre parcel on Whispering Knolls Dr in Winchester, VA. Nestled among scenic country roads, this property offers a peaceful setting to build your dream home. Located approximately 6 miles from I-81, it provides a manageable commute while still offering the charm of rural living. Winchester Medical Center is less than 10 miles away, with farmers markets, dining, and shopping also within easy reach. Situated off a paved road, the property features an established driveway (in need of improvement), along with a completed survey and soil study for a 4 bedroom perc—saving you time as you plan your build. Whether you're ready to build now or simply looking for a serene piece of land to call your own, this property captures the beauty and simplicity of country living.

Whispering Knolls Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$420,000

Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in Frederick County, VA offers the perfect blend of modern updates and peaceful country living. Situated on a picturesque setting, the home has been thoughtfully renovated throughout, featuring updated finishes, refreshed interiors, and attention to detail in every room. Enjoy the convenience of a detached garage—ideal for parking, storage, or a workshop—and take in the natural beauty of your own private pond, creating a serene outdoor retreat perfect for relaxing or entertaining. With its quiet location and completely renovated with modern finishes and thoughtful upgrades throughout. The seller has chosen not to display interior photos

3 Beds ⋅ 2 Baths

Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in Frederick County, VA offers the perfect blend of modern updates and peaceful country living. Situated on a picturesque setting, the home has been thoughtfully renovated throughout, featuring updated finishes, refreshed interiors, and attention to detail in every room. Enjoy the convenience of a detached garage—ideal for parking, storage, or a workshop—and take in the natural beauty of your own private pond, creating a serene outdoor retreat perfect for relaxing or entertaining. With its quiet location and completely renovated with modern finishes and thoughtful upgrades throughout. The seller has chosen not to display interior photos

775 Pack Horse Rd, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$1,499,000

Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

821,829,839, and 851 Fox, Winchester

Listing courtesy of Coldwell Banker Realty. Contact:

$1,499,000

Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

821,829,839, and 851 Fox, Winchester

Listing courtesy of Coldwell Banker Realty. Contact:

$24,900

Imagine creating your own mountain getaway atop Great North Mountain. Tucked among the trees in Shawneeland, this just-under-half-acre lot offers a peaceful wooded setting, privacy, and the potential for beautiful westerly mountain views. The property includes a relatively level area that may offer possibilities for a future homesite. With thoughtful planning and clearing, envision a cozy cabin, mountain chalet, or full-time residence surrounded by the natural beauty of the mountain. Enjoy the feeling of being tucked away in the mountains while remaining approximately 20 minutes from Winchester, with hard-surface roads for most of the drive. A previous septic approval for a 4-bedroom Puraflo system, dated 2006, is available in the listing documents. Buyers should perform their own due diligence and verify current septic requirements, approvals, and building requirements with the appropriate county authorities. Whether you're dreaming of a weekend escape or a place to call home year-round, Bobcat Trl offers an opportunity to create your own retreat on Great North Mountain.

162 Bobcat Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$634,000

PRICE REDUCTION ALERT! This is your chance to own the private retreat buyers have been waiting for. Step into something special at 256 Brookneil Dr—where space, privacy, and flexibility come together beautifully. Nestled on 2.1 wooded acres just minutes from Winchester, this property offers a peaceful retreat with the soothing sounds of nature all around. Whether you're sipping coffee on the deck or unwinding after a long day, the setting delivers the kind of tranquility that’s hard to find. Inside, the home is designed with both comfort and versatility in mind. The spacious main living area welcomes you with an open layout, highlighted by a stunning double-sided fireplace that creates a warm, inviting flow between the family and living rooms. It’s the perfect space for gathering, relaxing, and making memories. One of the standout features is the private second-floor suite—complete with its own kitchen with stove, & refrigerator, full bath, and walk-out access to a secluded porch. Ideal for multi-generational living, guests, or this space gives you options that truly set this home apart. And let’s talk outdoor living—four decks off the kitchen plus a multi-level deck off the family room create endless opportunities for entertaining, enjoying the views, or simply soaking in the peaceful surroundings. Additional peace of mind comes with a new roof installed in 2021. Let’s schedule your private tour and see how this home fits your next chapter.

4 Beds ⋅ 4 Baths

PRICE REDUCTION ALERT! This is your chance to own the private retreat buyers have been waiting for. Step into something special at 256 Brookneil Dr—where space, privacy, and flexibility come together beautifully. Nestled on 2.1 wooded acres just minutes from Winchester, this property offers a peaceful retreat with the soothing sounds of nature all around. Whether you're sipping coffee on the deck or unwinding after a long day, the setting delivers the kind of tranquility that’s hard to find. Inside, the home is designed with both comfort and versatility in mind. The spacious main living area welcomes you with an open layout, highlighted by a stunning double-sided fireplace that creates a warm, inviting flow between the family and living rooms. It’s the perfect space for gathering, relaxing, and making memories. One of the standout features is the private second-floor suite—complete with its own kitchen with stove, & refrigerator, full bath, and walk-out access to a secluded porch. Ideal for multi-generational living, guests, or this space gives you options that truly set this home apart. And let’s talk outdoor living—four decks off the kitchen plus a multi-level deck off the family room create endless opportunities for entertaining, enjoying the views, or simply soaking in the peaceful surroundings. Additional peace of mind comes with a new roof installed in 2021. Let’s schedule your private tour and see how this home fits your next chapter.

256 Brookneil Dr, Winchester

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

$925,000

PLEASE NOTE THAT THERE IS AN ELECTRIC FENCE. PLEASE MAKE SURE IT'S CLOSED BEHIND YOU WHEN ENTERING AND EXITING PROPERTY. MUST HAVE AN APPOINTMENT AND BE ACCOMPANIED BY AN AGENT TO SEE THIS PROPERTY. A truly rare opportunity to own over 150 acres in Frederick Co., VA , just a few miles west of the scenic Shenandoah Valley—where rolling pasture, privacy, and possibility come together. 950 Stony Hill Rd. offers a stunning blend of open farmland and natural beauty. With significant portions of the land farmable, this property is perfectly suited for agricultural use, equestrian pursuits, or creating a remarkable private estate or multi-generational retreat. Development may be possible. Any Purchaser needs to do their own research for their desired use(s). Existing features include available electric and a former tenant house (not livable). This property is 15 minutes from Historic Old Town Winchester, featuring a wide array of shopping, dining and entertainment options. Year-round outdoor activity pursuits are possible on property or nearby, including, golfing, hiking, fishing, kayaking and even skiing within 2 to 2.5 hours. Must be accompanied by Agent and have appointment to tour property. Livestock on property. D0 NOT ENTER OLD TENANT HOUSE. IT'S NOT SAFE. ENTRY TO STUCTURE IS STRICTLY FORBIDDEN. Private property. No drive-bys.

950 Stony Hill Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$649,500

100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

3 Beds ⋅ 3 Baths

100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

112 W Germain St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$749,900

Looking for a home that gives you space, style, privacy, and the freedom to make it your own? Welcome to this stately Colonial set on nearly an acre of beautiful, private land—where timeless architecture meets the upgrades today's buyers want. The seller has invested more than $150,000 in improvements, including a fully renovated HVAC system with all-new ductwork and high-end components. The result?....Modern comfort, improved efficiency, and one less thing to worry about. Inside, the main level delivers the kind of flexibility that fits today's lifestyle. A private main-level primary suite with a beautifully updated en-suite bath creates a convenient retreat, while rich hardwood floors, an inviting living room, dining room, spacious family room, and dedicated private study provide space for everything from quiet work-from-home days to weekend gatherings. At the heart of the home, the gourmet kitchen combines style and function with an induction cooktop and plenty of room to cook, gather, and entertain. Upstairs, the possibilities really open up. A second expansive primary suite offers an ideal option for guests, a private retreat, or multi-generational living, while four additional generously sized bedrooms give you plenty of flexibility for bedrooms, a home office, fitness space, hobbies, or whatever your lifestyle demands. And if you’re looking for room to grow, you’ll find it here. A walk-up fourth-floor attic, partial unfinished basement, and abundant storage give you valuable space to customize now or finish down the road. Step outside and enjoy your own private escape. The beautifully designed paver patio and expansive deck create an incredible setting for morning coffee, summer dinners, or entertaining friends, while the new shed adds convenient storage for all your outdoor gear. Best of all? No HOA. Bring your vision, your style, and your plans—without the restrictions of an HOA. With nearly an acre of land, exceptional flexibility, significant recent upgrades, multiple living spaces, and no HOA, this is more than a beautifully maintained Colonial. It’s a home designed to grow with you—and a lifestyle you’ll love coming home to.

5 Beds ⋅ 4 Baths

Looking for a home that gives you space, style, privacy, and the freedom to make it your own? Welcome to this stately Colonial set on nearly an acre of beautiful, private land—where timeless architecture meets the upgrades today's buyers want. The seller has invested more than $150,000 in improvements, including a fully renovated HVAC system with all-new ductwork and high-end components. The result?....Modern comfort, improved efficiency, and one less thing to worry about. Inside, the main level delivers the kind of flexibility that fits today's lifestyle. A private main-level primary suite with a beautifully updated en-suite bath creates a convenient retreat, while rich hardwood floors, an inviting living room, dining room, spacious family room, and dedicated private study provide space for everything from quiet work-from-home days to weekend gatherings. At the heart of the home, the gourmet kitchen combines style and function with an induction cooktop and plenty of room to cook, gather, and entertain. Upstairs, the possibilities really open up. A second expansive primary suite offers an ideal option for guests, a private retreat, or multi-generational living, while four additional generously sized bedrooms give you plenty of flexibility for bedrooms, a home office, fitness space, hobbies, or whatever your lifestyle demands. And if you’re looking for room to grow, you’ll find it here. A walk-up fourth-floor attic, partial unfinished basement, and abundant storage give you valuable space to customize now or finish down the road. Step outside and enjoy your own private escape. The beautifully designed paver patio and expansive deck create an incredible setting for morning coffee, summer dinners, or entertaining friends, while the new shed adds convenient storage for all your outdoor gear. Best of all? No HOA. Bring your vision, your style, and your plans—without the restrictions of an HOA. With nearly an acre of land, exceptional flexibility, significant recent upgrades, multiple living spaces, and no HOA, this is more than a beautifully maintained Colonial. It’s a home designed to grow with you—and a lifestyle you’ll love coming home to.

107 Launchris Dr, Winchester

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

$1,182,695

7082 SF, Prime Office Available for Lease, Winchester, VA. Located in established business park, all brick construction, super clean and ready for Q3 occupancy! Large open office concepts with multiple executive offices. Large breakroom, multiple M/W bathrooms, and bright, welcoming lobby. TONS OF FREE PARKING! High speed internet, Enterprise Zone benefits! $12 PSF + $2.65 NNN (inclusive with condo dues). Also listed for sale, $1,182,694. Optional, additional 3K SF of offices available on separate 2nd floor for a total of 10K+ if needed!

252 Airport Unit 3, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$609,990

Experience effortless living in our Willow Run Active Adult community! Our Azalea floorplan is a thoughtfully designed 1,888 sq. ft. ranch home blending style and functionality in a single-level open layout. The moment you step inside the home, you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen, ideal for entertaining. The chef’s kitchen boasts stainless steel appliances, a walk-in pantry, and a breakfast bar. From the breakfast nook, step through the sliding glass door to a covered porch, perfect for outdoor gatherings or morning coffee. The main level also features three generously sized bedrooms and two modern bathrooms - including a serene owner’s suite with dual vanities, a tiled walk-in shower, and generously sized walk-in closet. Need space for visiting friends or family? The finished basement offers an additional 1,021 sq. ft. of a living space with a rec room, full bath, and bedroom – plus 700 sq. ft. of unfinished space for storage. Completed with a large laundry room, two-car garage, and a low-maintenance lifestyle, the Azalea offers comfort and convenience. Embrace one-story living and make The Azalea your perfect new home this November! *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

4 Beds ⋅ 3 Baths

Experience effortless living in our Willow Run Active Adult community! Our Azalea floorplan is a thoughtfully designed 1,888 sq. ft. ranch home blending style and functionality in a single-level open layout. The moment you step inside the home, you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen, ideal for entertaining. The chef’s kitchen boasts stainless steel appliances, a walk-in pantry, and a breakfast bar. From the breakfast nook, step through the sliding glass door to a covered porch, perfect for outdoor gatherings or morning coffee. The main level also features three generously sized bedrooms and two modern bathrooms - including a serene owner’s suite with dual vanities, a tiled walk-in shower, and generously sized walk-in closet. Need space for visiting friends or family? The finished basement offers an additional 1,021 sq. ft. of a living space with a rec room, full bath, and bedroom – plus 700 sq. ft. of unfinished space for storage. Completed with a large laundry room, two-car garage, and a low-maintenance lifestyle, the Azalea offers comfort and convenience. Embrace one-story living and make The Azalea your perfect new home this November! *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

232 Hydrangea Way, Winchester

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

$589,990

Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq. ft. ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in natural light. The chef’s kitchen boasts stainless steel appliances, a pantry, and generous amount of cabinets and counter top space. From the great room, step through the sliding glass door to a covered porch, perfect for outdoor gatherings or morning coffee. The main level also features three generously sized bedrooms and two modern bathrooms - including a serene owner’s suite with dual vanities, a tiled walk-in shower, and two large walk-in closets. Need space for visiting friends or family? The finished basement offers an additional 1,000sq. ft. of a living space with a rec room, full bath, and bedroom – plus a large unfinished space for storage. Completed with a large laundry room, two-car garage, and a low-maintenance lifestyle, the Clifton offers comfort and convenience. Embrace one-story living and make The Clifton your perfect new home this November! *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

4 Beds ⋅ 3 Baths

Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq. ft. ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in natural light. The chef’s kitchen boasts stainless steel appliances, a pantry, and generous amount of cabinets and counter top space. From the great room, step through the sliding glass door to a covered porch, perfect for outdoor gatherings or morning coffee. The main level also features three generously sized bedrooms and two modern bathrooms - including a serene owner’s suite with dual vanities, a tiled walk-in shower, and two large walk-in closets. Need space for visiting friends or family? The finished basement offers an additional 1,000sq. ft. of a living space with a rec room, full bath, and bedroom – plus a large unfinished space for storage. Completed with a large laundry room, two-car garage, and a low-maintenance lifestyle, the Clifton offers comfort and convenience. Embrace one-story living and make The Clifton your perfect new home this November! *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

239 Hydrangea Way, Winchester

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

$680,000

This stunning new construction home features a charming Craftsman and Farmhouse architectural style, set on a generous 5.15-acre lot with breathtaking mountain and wooded views. The open floor plan seamlessly connects the family room to a country-style kitchen, complete with a spacious island, pantry, and energy-efficient stainless steel appliances, including a double oven and built-in microwave. With three bedrooms and two full bathrooms, this residence offers ample space for comfortable living. The main floor laundry adds convenience, while the unfinished poured concrete basement provides potential for customization. Located in a vibrant community, residents enjoy access to excellent local schools, nearby parks, and essential public services. The attached side-entry garage enhances functionality, making this property a perfect blend of modern living and natural beauty. Don't miss the opportunity to make this exceptional home your own!

3 Beds ⋅ 2 Baths

This stunning new construction home features a charming Craftsman and Farmhouse architectural style, set on a generous 5.15-acre lot with breathtaking mountain and wooded views. The open floor plan seamlessly connects the family room to a country-style kitchen, complete with a spacious island, pantry, and energy-efficient stainless steel appliances, including a double oven and built-in microwave. With three bedrooms and two full bathrooms, this residence offers ample space for comfortable living. The main floor laundry adds convenience, while the unfinished poured concrete basement provides potential for customization. Located in a vibrant community, residents enjoy access to excellent local schools, nearby parks, and essential public services. The attached side-entry garage enhances functionality, making this property a perfect blend of modern living and natural beauty. Don't miss the opportunity to make this exceptional home your own!

Tumble Leaf Lane, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$799,900

No HOA!! Don’t miss this incredible opportunity to own a brand-new ranch home set on 2.66 beautiful acres, conveniently located near shopping and commuter routes to Winchester, Martinsburg, and Northern Virginia and approximately 10 minutes from the Winchester Medical Center. This thoughtfully designed home features an open-concept layout with a desirable split-bedroom design, offering both comfort and privacy. The charming exterior showcases board and batten siding for a distinctive look. Inside, the spacious primary suite includes a large walk-in closet and a luxurious 6-foot tile shower, while a private main-level office provides the perfect work-from-home space. The chef’s kitchen is equipped with quartz countertops, a center island, stainless steel appliances, and quality cabinetry with soft-close drawers and doors. A bright sunroom fills the home with natural light, and additional highlights include a main-level laundry room with utility sink, extensive luxury vinyl plank flooring, and an enormous unfinished basement already plumbed for a future bathroom with an HVAC system sized for finishing. The home also offers a two-car side-load garage, a covered front porch with a concrete sidewalk, and a scenic lot with mature hardwoods. Construction is underway and a similar model home nearby is available to tour. There is still time to select some colors and options. Photos are of a similar home and may include upgraded features.

3 Beds ⋅ 3 Baths

No HOA!! Don’t miss this incredible opportunity to own a brand-new ranch home set on 2.66 beautiful acres, conveniently located near shopping and commuter routes to Winchester, Martinsburg, and Northern Virginia and approximately 10 minutes from the Winchester Medical Center. This thoughtfully designed home features an open-concept layout with a desirable split-bedroom design, offering both comfort and privacy. The charming exterior showcases board and batten siding for a distinctive look. Inside, the spacious primary suite includes a large walk-in closet and a luxurious 6-foot tile shower, while a private main-level office provides the perfect work-from-home space. The chef’s kitchen is equipped with quartz countertops, a center island, stainless steel appliances, and quality cabinetry with soft-close drawers and doors. A bright sunroom fills the home with natural light, and additional highlights include a main-level laundry room with utility sink, extensive luxury vinyl plank flooring, and an enormous unfinished basement already plumbed for a future bathroom with an HVAC system sized for finishing. The home also offers a two-car side-load garage, a covered front porch with a concrete sidewalk, and a scenic lot with mature hardwoods. Construction is underway and a similar model home nearby is available to tour. There is still time to select some colors and options. Photos are of a similar home and may include upgraded features.

123 Stetson St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$7,900

Great opportunity to own two beautiful wooded lots full of mature trees and plenty of privacy! These adjoining parcels offer a wonderful chance to connect with nature and enjoy peaceful surroundings. Located just about 30 minutes from downtown Winchester, you get the perfect mix of country calm and town convenience. Whether you’re thinking about outdoor fun, future plans, or simply an investment, these lots have exciting potential!! Schedule your showing today.

LOTS 8 & 9 & Trl, Winchester

Listing courtesy of Samson Properties. Contact:

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