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Prime Commercial Investment Opportunity – Frederick County, VA Strategically located near the intersection of Interstate 81 and Virginia Bypass 37, this unique offering presents a rare opportunity to acquire two well-maintained commercial buildings plus additional development acreage in a high-demand corridor. Property Highlights: • 180 Prosperity Drive: • 13,500 SF | Built in 2004 | Zoned B-3 • 190 Prosperity Drive: • 18,000 SF | Built in 2007 | Zoned B-3 • Total Building Area: 31,500 SF across 3.83 acres • Zoning: All existing structures zoned B-3 • Site Features: Ample off-street parking, convenient dock door access Additional Land Included: • 8.86 Acres Zoned B-2 • Total Land Area: 12.7 Acres (Buildings + B-2 Parcel) • B-2 Approved Uses: Self-storage, distribution warehouses, car washes, new car dealerships, hotels, restaurants, and more Financials: • Net Operating Income (NOI): $326,000 • Detailed Financials & Rent Roll: Available upon execution of NDA 📞 Contact Broker for further details and to schedule a site visit.

180-190 Prosperity Dr, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$4,990,000

Rutherford Crossing is a two-tenant NNN retail strip center at 105-109 Market Street in Winchester, VA, anchored by corporate Starbucks (S&P: BBB+) with 10% rent step-ups every five years, alongside V Nails & Spas on a lease running through 2035. The offering delivers approximately $330,000 in stabilized NOI with true triple net structure and minimal landlord responsibilities, making it a clean, passive addition to any retail investment portfolio. The property sits within Rutherford Crossing, an approximately 600,000 SF power center along the growing I-81 corridor, surrounded by national credit anchors and steady daily traffic that drive consistent consumer draw. Winchester continues to see strong population and retail growth, giving this asset the location fundamentals and co-tenancy strength that long-term investors look for.

105 Market St, Winchester

Listing courtesy of CapStar Properties. Contact:

$4,000,000

Aviator Business Center consists of 3 completed buildings with an aggregate finished floor area of approximately 9,660 SF. This valuable property is sited on 5.85 acres within the heart of the Winchester Regional Airport. There are seven (7) undeveloped site plan approved lots. Each hypothetical lot is not subdivided into recordable lots. This provides the new owner flexibility in designing future building sizes. There is a current MAI appraisal in file dated May 2025 for $4 million. The appraisal is provided in the attached documents.

112 Aviator Pl, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$4,000,000

19 Acres, Prime Commercial or FLEX Development Opportunity! Zoned B2, General Commercial. Major commuter corridor to Northern VA, adjacent to Airport Business Park, FBI Records Center, Navy Federal Credit Union headquarters, and new One Logistics Park. Also #1 commuter route to Northern VA! Excellent visibility, flat topo, and dual access on Victory Lane and Independence! Sale includes 14.06 acres and adjacent 5 acre parcel. All 19 acres sold as a whole. Public utilities to site! Asking $4M.

368 Victory Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$3,500,000

Be sure to see the video and 3D tour to fully explore this property! Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term Rental + Development Lots! br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals. For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership. The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals. The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional. Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,500,000

Be Sure to View the Video and 3D Tour to Fully Experience this Stunning Property **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals. For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership. The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals. The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional. Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

3 Beds ⋅ 4 Baths

Be Sure to View the Video and 3D Tour to Fully Experience this Stunning Property **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals. For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership. The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals. The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional. Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

450 Green Spring Rd, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,500,000

Be sure to see the video and 3D tour to fully explore this property! Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term Rental + Development Lots! br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals. For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership. The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals. The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional. Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

3 Beds ⋅ 4 Baths

Be sure to see the video and 3D tour to fully explore this property! Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term Rental + Development Lots! br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals. For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership. The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals. The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional. Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

450 Green Spring Rd, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,250,000

Here is the opportunity to own a piece of history! The hottest spot in Winchester/Frederick County. The 20,386+/- SF building started out as a furniture warehouse that served the area for many years. In 2005 it was converted to a Restaurant that is now the most popular dining and entertainment destination in the area. In addition to the famous “pub” area, the restaurant includes a more formal dining area with a piano bar, tons of outdoor seating, Banquet and events area on upper level, outdoor covered desk/bar and the most popular feature, “The Jam Rock Boat.” That’s right, an actual boat was hauled in and permanently installed to provide an area for bands to use as a stage. This is a major draw on Friday and Saturday nights when the best local bands entertain the crowds. Just steps from the Old Town Walking Mall and adjacent to the historic Wyndham/George Washington Hotel. Well-established turn-key business that includes all fixtures, equipment, and real estate. Owner wants to retire but will assist with transition after purchase. Seasoned, well-trained managers and staff will stay. Winchester is seeing incredible growth. This is an opportunity to ride the expansion which will be seen in the coming years. CPA prepared financials available to qualified buyers. Non-disclosure Agreement required. Owner financing available with acceptable down payment.

125 E Piccadilly St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$3,250,000

Rare opportunity to own a 22,320 sq. ft. indoor sports and entertainment facility situated on 3 acres with Industrial zoning. Formerly a youth development center, the building features two gymnasiums, a theater area, multiple kitchens with dining spaces, and several large restroom areas. The flexible layout supports single-tenant or multi-tenant use, making it ideal for recreational, institutional, or commercial operations. The property also offers extensive on-site parking and excellent potential for adaptive reuse. Unique large-scale facility with a wide range of possible uses.

3 Battaile Dr, Winchester

Listing courtesy of Commercial Specialists. Contact:

$3,200,000

Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities, with previous concept plans by Greenway Engineering that included options such as a retail strip center with a drive-through end cap and medical office buildings. The area’s strong demand for affordable housing also presents an excellent residential development opportunity. With thousands of daily commuters traveling from West Virginia into Virginia along this corridor, the site benefits from consistent, high-volume traffic flow. This is a rare chance to bring a high-impact commercial or mixed-use project to one of Winchester’s most dynamic and growing areas. Photos may be virtually staged

Northwestern Pike, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,200,000

Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities, with previous concept plans by Greenway Engineering that included options such as a retail strip center with a drive-through end cap and medical office buildings. The area’s strong demand for affordable housing also presents an excellent residential development opportunity. With thousands of daily commuters traveling from West Virginia into Virginia along this corridor, the site benefits from consistent, high-volume traffic flow. This is a rare chance to bring a high-impact commercial or mixed-use project to one of Winchester’s most dynamic and growing areas. Photos may be virtually staged

Northwestern Pike, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$3,200,000

472 Mccubbin Rd, Winchester

Listing courtesy of TTR Sotheby's International Realty. Contact:

$3,175,000

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

6 Beds ⋅ 7 Baths

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

730 Merrimans Ln, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$3,025,000

27.09 +/- acres in the direct path of Light Industrial-Zoned land. The subject property is in the comprehensive plan to be zoned Light Industrial for warehousing, distribution, self-storage warehousing or light manufacturing. The 27.09 +/- acre site has excellent proximity and access to US 11, Route 37. and I-81. The property provides location, visibility, and exposure. All utilities are available. The site is ideally located in the southern portion of the Winchester area known as the Kernstown submarket. There is the possibility of railroad access on the western boundary of the subject property. The site will provide connection to Shady Elm Road and the Valley Innovation Park (Peterson Cos) which is scheduled to begin construction in 2026.

Renaissance Dr, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$3,025,000

27.09 +/- acres in the direct path of Light Industrial-Zoned land. The subject property is in the comprehensive plan to be zoned Light Industrial for warehousing, distribution, self-storage warehousing or light manufacturing. The 27.09 +/- acre site has excellent proximity and access to US 11, Route 37. and I-81. The property provides location, visibility, and exposure. All utilities are available. The site is ideally located in the southern portion of the Winchester area known as the Kernstown submarket. There is the possibility of railroad access on the western boundary of the subject property. The site will provide connection to Shady Elm Road and the Valley Innovation Park (Peterson Cos) which is scheduled to begin construction in 2026.

Renaissance Dr, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$2,599,000

This upscale custom home blends clean, modern comfort with rustic charm—and does it sublimely with nearly 5,000 finished square feet on one level, including a separate in-law suite. Resting on 5.38 pastoral acres, the handsome façade includes charming details like exposed beams, stonework, classic exterior barn lighting, a metal roof, and a grand covered porch with stunning details that preview the craftsmanship inside. The entry welcomes you to a great room with some delineations for the dining and kitchen areas. Plank hardwood floors, high ceilings, and pleasing neutral colors combine with fetching built-ins, exposed beams, and lighting that create an environment that’s cozy, elegant, and inviting. The dining area to the left has a handy built-in bar and wine cooler. The roomy kitchen is a chef’s dream with its pristine white cabinetry, upscale appliances, and a four-seat wooden island with a quartz countertop that matches the rest of the kitchen counters and backsplash. The crown jewel is the main living area with its luxurious lounge space, anchoring stone fireplace, and beams overhead, adding to the seamless ease of this floorplan. The main home has three bedrooms and 3.5 baths, along with a sizeable laundry room with counterspace and storage galore plus another room perfectly suited for a den, library, or office. The bedrooms are thoughtfully designed, all with attached baths, and the owner’s suite can only be described as resplendent. With its location on one end of the home, the suite provides picturesque views of the outdoors not only from the generous bedroom itself, but also in the bright sitting area, offset by glass barn doors. In addition to a deluxe walk-in closet, the ensuite offers a stylish double vanity, standalone soaking tub, and walk-in shower. The in-law suite is separated by a breezeway with its own entrance and contains the same high-end features in terms of floors, color scheme, and vibe. The common area is both practical and comforting with natural light in the kitchen, dining, and living rooms, the latter getting a dose of ambiance from the stone fireplace. A large bedroom and attached bath sit adjacent, along with a laundry room, and a screened-in porch overlooks the backyard. And let’s talk about the attractive pool and patio area. It’s the icing on the cake—spacious with covered and open seating and dining and a rectangular heated pool at its center. An pool house provides a bar/kitchenette and entertainment center (with TV!) with a pull-out awning for extra shade plus a half-bath and changing room. The area is fenced and landscaped as thoughtfully as the rest of the home and surrounded by lush lawn with a backdrop of mature hardwoods, making for an idyllic setting. There’s also a three-car garage (with bonus room), and a separate outbuilding to use as you like that are both fully heated and cooled. Built with craft and care three years ago, this is arguably the best lot in Frederick County, and with a Winchester address, it’s close to amenities and main arteries, while still offering a quiet, private enclave that is seriously swoon-worthy.

4 Beds ⋅ 6 Baths

This upscale custom home blends clean, modern comfort with rustic charm—and does it sublimely with nearly 5,000 finished square feet on one level, including a separate in-law suite. Resting on 5.38 pastoral acres, the handsome façade includes charming details like exposed beams, stonework, classic exterior barn lighting, a metal roof, and a grand covered porch with stunning details that preview the craftsmanship inside. The entry welcomes you to a great room with some delineations for the dining and kitchen areas. Plank hardwood floors, high ceilings, and pleasing neutral colors combine with fetching built-ins, exposed beams, and lighting that create an environment that’s cozy, elegant, and inviting. The dining area to the left has a handy built-in bar and wine cooler. The roomy kitchen is a chef’s dream with its pristine white cabinetry, upscale appliances, and a four-seat wooden island with a quartz countertop that matches the rest of the kitchen counters and backsplash. The crown jewel is the main living area with its luxurious lounge space, anchoring stone fireplace, and beams overhead, adding to the seamless ease of this floorplan. The main home has three bedrooms and 3.5 baths, along with a sizeable laundry room with counterspace and storage galore plus another room perfectly suited for a den, library, or office. The bedrooms are thoughtfully designed, all with attached baths, and the owner’s suite can only be described as resplendent. With its location on one end of the home, the suite provides picturesque views of the outdoors not only from the generous bedroom itself, but also in the bright sitting area, offset by glass barn doors. In addition to a deluxe walk-in closet, the ensuite offers a stylish double vanity, standalone soaking tub, and walk-in shower. The in-law suite is separated by a breezeway with its own entrance and contains the same high-end features in terms of floors, color scheme, and vibe. The common area is both practical and comforting with natural light in the kitchen, dining, and living rooms, the latter getting a dose of ambiance from the stone fireplace. A large bedroom and attached bath sit adjacent, along with a laundry room, and a screened-in porch overlooks the backyard. And let’s talk about the attractive pool and patio area. It’s the icing on the cake—spacious with covered and open seating and dining and a rectangular heated pool at its center. An pool house provides a bar/kitchenette and entertainment center (with TV!) with a pull-out awning for extra shade plus a half-bath and changing room. The area is fenced and landscaped as thoughtfully as the rest of the home and surrounded by lush lawn with a backdrop of mature hardwoods, making for an idyllic setting. There’s also a three-car garage (with bonus room), and a separate outbuilding to use as you like that are both fully heated and cooled. Built with craft and care three years ago, this is arguably the best lot in Frederick County, and with a Winchester address, it’s close to amenities and main arteries, while still offering a quiet, private enclave that is seriously swoon-worthy.

144 Robinson Dr, Winchester

Listing courtesy of Colony Realty. Contact:

$2,525,100

8.86 Acres of undeveloped commercial land zoned B-2 with excellent US 37 future signage visibility, exposure, and location. All utilities available for connection. Approved uses include self-storage warehouses, distribution warehouses, car washes, new car dealerships, hotels and restaurants.

Kavanaugh Dr, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$2,525,100

8.86 Acres of undeveloped commercial land zoned B-2 with excellent US 37 future signage visibility, exposure, and location. All utilities available for connection. Approved uses include self-storage warehouses, distribution warehouses, car washes, new car dealerships, hotels and restaurants.

Kavanaugh Dr, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$2,286,000

5.08 Acres zoned B-2 in Rutherford Crossing shopping center. Owner will consider subdivision of the property. Directly across from Lowes and Target and next to Spring Hill Marriot Hotel and Suites and FEMA call center. Ideal for hotels, restaurants, office buildings, retail, etc... John Schroth and John Scully, owners are licensed Realtors in the state of Virginia.

Market Street, Winchester

Listing courtesy of Colony Realty. Contact:

$2,286,000

5.08 Acres zoned from B-2 in Rutherford Crossing shopping center. Owner will consider subdivision of the property. Directly across from Lowes and Target and next to Spring Hill Marriot Hotel and Suites and FEMA Call Center. Ideal for hotels, restaurants, office buildings, retail, etc... John Schroth and John Scully, owners, are licensed Realtors in the state of Virginia.

Market St., Winchester

Listing courtesy of Colony Realty. Contact:

$2,200,000

Privately sited on 6.11 acres just outside Winchester, 261 Merrifield Lane pairs classic Georgian architecture with extensive recent improvements throughout its approximately 6,343 sq. ft. of living space. A tree-lined approach and circular drive introduce this all-brick estate, where hardwood floors, substantial millwork, multiple fireplaces, a paneled library with built-ins and bar, formal living and dining rooms, sunroom and expansive gathering spaces create a home of remarkable character. Recent updates include new windows, refinished hardwood flooring, extensive interior painting and wall restoration, updated lighting and high-end plumbing fixtures, refreshed guest baths, landscape and drainage improvements, patio work and a completely renovated primary bath with new flooring, tile, tub, shower, cabinetry, counters, lighting and fixtures. The kitchen offers custom cabinetry, center island and paneled appliances, while the finished lower level provides additional recreation and entertaining space. A private apartment above the three-car garage includes its own entrance, living area, kitchenette, bedroom, full bath and laundry—ideal for flexible guest or extended-stay accommodations. Mature grounds provide exceptional privacy while remaining minutes from Winchester's historic district, Winchester Medical Center, the Museum of the Shenandoah Valley and major commuter routes

5 Beds ⋅ 6 Baths

Privately sited on 6.11 acres just outside Winchester, 261 Merrifield Lane pairs classic Georgian architecture with extensive recent improvements throughout its approximately 6,343 sq. ft. of living space. A tree-lined approach and circular drive introduce this all-brick estate, where hardwood floors, substantial millwork, multiple fireplaces, a paneled library with built-ins and bar, formal living and dining rooms, sunroom and expansive gathering spaces create a home of remarkable character. Recent updates include new windows, refinished hardwood flooring, extensive interior painting and wall restoration, updated lighting and high-end plumbing fixtures, refreshed guest baths, landscape and drainage improvements, patio work and a completely renovated primary bath with new flooring, tile, tub, shower, cabinetry, counters, lighting and fixtures. The kitchen offers custom cabinetry, center island and paneled appliances, while the finished lower level provides additional recreation and entertaining space. A private apartment above the three-car garage includes its own entrance, living area, kitchenette, bedroom, full bath and laundry—ideal for flexible guest or extended-stay accommodations. Mature grounds provide exceptional privacy while remaining minutes from Winchester's historic district, Winchester Medical Center, the Museum of the Shenandoah Valley and major commuter routes

261 Merrifield Ln, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. 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:

$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:

$1,975,000

Professional Office Space For Sale. This building was the former Winchester City Schools Administrative Building. There are two floors plus a basement. There are 5,670 SF on each of two floors. Located only blocks from the Loudoun Street Walking Mall. Basement office space available. Presently the building is fully leased. There are 16 on-street parking spaces.

12 N Washington St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$1,950,000

5.26 Acres of Interstate/Commercial Land SALE Available, Frederick County, VA, Exit 317. Besides Taco Bell, across from new hotel, surrounded by commercial, connects to Crown Lane for traffic light access! Excellent visibility on Martinsburg Pike (43k+ AADT VDOT '25). Ideal for restaurant, fast food, grocery, auto parts retailer, auto repair. Strong potential for rezoning for increased commercial uses. Over 700' road frontage. Offered for sale, 5.26 acres for $1,950,000. Subdivision considered. Currently zoned to allow multiple flex uses and restaurants. Rezoning would open multiple more commercial uses such as hotel, retail center, offices.

153 Welltown Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$1,950,000

5.26 Acres of Interstate/Commercial Land SALE Available, Frederick County, VA, Exit 317. Besides Taco Bell, across from new hotel, surrounded by commercial, connects to Crown Lane for traffic light access! Excellent visibility on Martinsburg Pike (43K+ AADT VDOT '25). Ideal for restaurant, fast food, grocery, auto parts retailer, auto repair. Strong potential for rezoning for increased commercial uses. Over 700' road frontage. Offered for sale, 5.26 acres for $1.8M. Subdivision considered and currently zoned to allow multiple flex uses and restaurants. Rezoning would open multiple more commercial uses such as hotel, retail center, offices.

153 Welltown Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$1,800,000

4.93 acres with great interstate exposure. End of cul de sac. Owners have proposed platt showing parcel subdivided into 4 parcels

Sulky, Winchester

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

$1,724,000

Beautifully restored and fully modernized mixed-use building in the heart of historic Winchester. This exceptional offering includes a fully leased commercial building with three strong-credit tenants, a valuable adjacent parking lot approved for future mixed-use development, and a third floor ready for residential conversion. Located just one block from the historic Old Town Winchester Walking Mall, this legacy investment property offers more than 9,300 square feet of space with the first and second floors completely renovated and occupied. The third floor presents an outstanding value-add opportunity for apartment development, with potential eligibility for Historic Tax Credits. The property is also located within an Enterprise Zone, providing access to additional grant and incentive programs. The sale includes the adjacent parking lot (Tax ID 173-01-E-1), which is approved for multifamily development or can continue to serve as a highly desirable dedicated parking facility for tenants and customers. Current net operating income exceeds $80,000 annually, providing immediate cash flow with significant upside potential. Recent capital improvements include a metal roof, new HVAC systems, and modern tenant build-outs throughout the building. This unique asset offers a diversified income stream with retail and office tenants in place, while creating future opportunities for residential development on both the third floor and the adjacent parking lot. Ideal for a 1031 exchange buyer or investor seeking stable income, long-term appreciation, and redevelopment potential in one of the Shenandoah Valley's most desirable downtown locations. Conveniently located one block from the Braddock Street Parking Garage. Rarely does an opportunity of this caliber become available in Downtown Winchester. Contact the listing agent to schedule a private showing.

48 W Boscawen, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$1,650,000

Built in 1774, before America was America, this remarkable 31-acre estate has stood through the birth of a nation, and today it's ready for its next chapter. This is history you can live in, a piece of the past, built for the life you're living now. Hardwood floors run throughout, and the spacious kitchen opens effortlessly into the family room and dining space, the kind of layout that makes everyday living and entertaining equally easy, with direct access to either the back patio or covered side porch. Four bedrooms include a primary suite with its own private & covered porch overlooking the 31.74 acres and pond, a quiet spot to start or end the day. Additional flexible bonus rooms offer options for guest space, an office, or extra bedrooms as needed, alongside 3 full and 2 half baths across. A 3-car attached garage adds everyday convenience. Outside, the property opens into 31.74 sweeping, scenic acres. A picturesque pond anchors the grounds, a substantial 100' x 50' barn with its own electric service offers exceptional storage or workshop space, ready for hobby farming, equipment, or a creative studio of your own. Just 15 minutes to downtown Winchester and minutes from local attractions like the Museum of the Shenandoah Valley, with Washington, DC only 84 miles away, this is countryside living with the city still within reach. A rare chance to own a true piece of American history, lived in, loved, and ready for its next 250 years.

4 Beds ⋅ 5 Baths

Built in 1774, before America was America, this remarkable 31-acre estate has stood through the birth of a nation, and today it's ready for its next chapter. This is history you can live in, a piece of the past, built for the life you're living now. Hardwood floors run throughout, and the spacious kitchen opens effortlessly into the family room and dining space, the kind of layout that makes everyday living and entertaining equally easy, with direct access to either the back patio or covered side porch. Four bedrooms include a primary suite with its own private & covered porch overlooking the 31.74 acres and pond, a quiet spot to start or end the day. Additional flexible bonus rooms offer options for guest space, an office, or extra bedrooms as needed, alongside 3 full and 2 half baths across. A 3-car attached garage adds everyday convenience. Outside, the property opens into 31.74 sweeping, scenic acres. A picturesque pond anchors the grounds, a substantial 100' x 50' barn with its own electric service offers exceptional storage or workshop space, ready for hobby farming, equipment, or a creative studio of your own. Just 15 minutes to downtown Winchester and minutes from local attractions like the Museum of the Shenandoah Valley, with Washington, DC only 84 miles away, this is countryside living with the city still within reach. A rare chance to own a true piece of American history, lived in, loved, and ready for its next 250 years.

582 Miller Rd, Winchester

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

310.87/- Acres Off Laurel Grove Rd, Winchester

$1,559,000

OUTSTANDING 310+/- ACRES IN WINCHESTER, VA – BEAUTIFUL VIEWS, EXCELLENT HUNTING, AND INCREDIBLE OPPORTUNITY! These two adjoining properties offer a rare opportunity to own approximately 310+/- acres in a beautiful and private setting just minutes from Winchester. With beautiful views, streams, wooded land, open land, approved perc sites, and excellent hunting opportunities, these properties offer endless possibilities for a dream home, cabin, recreational property, or private country estate. Tract 1: 152± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property features beautiful views, a cleared building site, an approved five-bedroom perc site, and electric has been run to the property, providing an excellent foundation for future development. Outdoor enthusiasts will appreciate the great hunting opportunities, with abundant wildlife including deer, turkey, and more. A stream flows through the property, adding to the natural beauty and creating a peaceful setting. An established road provides access into the property, with access from a deeded right-of-way off Laurel Grove Road. Located just 13 miles from Winchester and less than 9 miles from I-81 and Route 11, the property offers convenient access for commuting while maintaining a private, rural setting. Dulles International Airport is approximately 80 minutes away, with Washington, D.C. approximately 90 minutes away. Whether you're looking to build a home or cabin, enjoy great hunting, or create your own private getaway, this property offers an exceptional opportunity. Come and make this your next great adventure! Buyer is responsible for all due diligence regarding building suitability, permits, zoning, permitted uses, utilities, and any other intended use of the property. Tract 2: 158.43± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property features beautiful views, a cleared building site, an approved five-bedroom perc site, and electric is near to the property, providing an excellent foundation for future development. Outdoor enthusiasts will appreciate the great hunting opportunities, with abundant wildlife including deer, turkey, and more. A stream flows through the property, adding to the natural beauty and creating a peaceful setting. An established road provides access into the property, with access from a deeded right-of-way off Laurel Grove Road. Located just 13 miles from Winchester and less than 9 miles from I-81 and Route 11, the property offers convenient access for commuting while maintaining a private, rural setting. Dulles International Airport is approximately 80 minutes away, with Washington, D.C. approximately 90 minutes away. Whether you're looking to build a home or cabin, enjoy great hunting, or create your own private getaway, this property offers an exceptional opportunity. Come and make this your next great adventure! Buyer is responsible for all due diligence regarding building suitability, permits, zoning, permitted uses, utilities, potential utility projects, and any other intended use of the property. The property is crossed by existing power lines, and there may be a project to add an additional power line to the existing lines. At this time, the potential project has not been confirmed, and buyers should conduct their own due diligence regarding any proposed utility projects. This property will be offered at auction on Friday, October 16, 2026, at 1:00 PM. The list price in no way represents a minimum, starting, or acceptable bid. This property will be offered in a multi-parcel auction, giving buyers the flexibility to purchase Tract 1, Tract 2, or both tracts. Tract 1: 152.44+/- Acres Tract 2: 158.43+/- acres

310.87/- Acres Off Laurel Grove Rd, Winchester

Listing courtesy of Hurley Real Estate & Auctions. Contact: