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Lot 7 and 4035 Cedar Creek Grade, Winchester

Incredible opportunity to own a farm home in one of the most desirable locations in the Winchester/Shenandoah Valley area! The Sellers prefer to sell the home with the adjacent 64+ acres, but are open to selling the home by itself with a very strong offer (see MLS listing - VAFV2045418). Enjoy beautiful views and open space within minutes of Downtown Winchester, a truly rare opportunity! The home is currently being used as a meeting center, and many upgrades have already been done. Four years ago, the HVAC was replaced, plumbing was updated, windows and water heater replaced. Purchase this home/parcel with the adjacent parcel and enjoy almost 70 acres of beautiful land and Cedar Creek Grade road frontage. Lot 7 is protected by a conservation easement and has 1 Dwelling Unit available - cannot be subdivided. The home on the smaller parcel currently has 4 bedrooms and 2 baths. The parcel is separated from the adjacent barn (not included in the sale) by a stone wall and has a very small easement allowing access to the property with the barn. There is a 2nd easement that connects the rear of the property to Chandra Lane, giving 2 possibilities for a driveway. There is no driveway currently installed. Surrounded by nearby vineyards, farmers markets, and a wedding venue within a half mile, the location offers strong agritourism appeal. Enjoy gorgeous views and a peaceful rural setting, all while being just 10–15 minutes from downtown Winchester, grocery stores, and Winchester Medical Center. This is truly a very unique opportunity!

4 Beds ⋅ 1 Baths

Incredible opportunity to own a farm home in one of the most desirable locations in the Winchester/Shenandoah Valley area! The Sellers prefer to sell the home with the adjacent 64+ acres, but are open to selling the home by itself with a very strong offer (see MLS listing - VAFV2045418). Enjoy beautiful views and open space within minutes of Downtown Winchester, a truly rare opportunity! The home is currently being used as a meeting center, and many upgrades have already been done. Four years ago, the HVAC was replaced, plumbing was updated, windows and water heater replaced. Purchase this home/parcel with the adjacent parcel and enjoy almost 70 acres of beautiful land and Cedar Creek Grade road frontage. Lot 7 is protected by a conservation easement and has 1 Dwelling Unit available - cannot be subdivided. The home on the smaller parcel currently has 4 bedrooms and 2 baths. The parcel is separated from the adjacent barn (not included in the sale) by a stone wall and has a very small easement allowing access to the property with the barn. There is a 2nd easement that connects the rear of the property to Chandra Lane, giving 2 possibilities for a driveway. There is no driveway currently installed. Surrounded by nearby vineyards, farmers markets, and a wedding venue within a half mile, the location offers strong agritourism appeal. Enjoy gorgeous views and a peaceful rural setting, all while being just 10–15 minutes from downtown Winchester, grocery stores, and Winchester Medical Center. This is truly a very unique opportunity!

Lot 7 and 4035 Cedar Creek Grade, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$1,490,000

Privately nestled on five wooded acres just minutes from historic Winchester, this extensively renovated modern farmhouse offers more than 7,500 square feet of finished living space across three distinct finished living areas, providing exceptional flexibility for multi-generational living, extended family, guests or those seeking dedicated private space. The main residence combines exposed wood beams, hardwood floors, abundant natural light and polished finishes with generous living and entertaining spaces. Expansive country and mountain views are framed from the upper deck and dining room through a wall of windows and exposed beams. The finished walk-out lower level creates a second private living area with its own full kitchen, offering additional flexibility and separation. Completed in 2025, the approximately 1,700-square-foot attached ADU provides a third fully finished living area with a separate entrance and its own living room, dining room, full kitchen, two bedrooms with en-suite baths and a half bath. Beneath the ADU, approximately 1,861 square feet of unfinished basement space provides substantial storage and future potential. A custom-designed office overlooks the pool and surrounding grounds, offering a dedicated work-from-home space with views of the property. Outdoor living is centered around the heated in-ground saltwater pool, large deck, patio and fire-pit area, complemented by extensive hardscaping for entertaining, dining and relaxing. The five-acre grounds combine mature woods, landscaped areas and open spaces with an established collection of fruit trees and berry bushes, including fig, cherry, pear, persimmon, peach, plum and blackberry. A finished 15' x 15' outbuilding with LVP flooring and a mini-split provides additional flexible space for an office, studio, gym or hobby room. The attached two-car garage features custom cabinetry, while the paved driveway offers ample parking. Major improvements include the 2025 ADU addition, Andersen replacement windows, main-level HVAC replaced in 2024, upper-level HVAC replaced in 2025, and updates to the roof, siding, pool equipment and more. With three finished living areas, substantial additional unfinished space, five private acres, mountain and country views, a heated saltwater pool and multiple flexible work and entertaining spaces, this distinctive property offers space and privacy while remaining conveniently located near Winchester and within walking distance of Valerie Hill Vineyard & Winery.

6 Beds ⋅ 7 Baths

Privately nestled on five wooded acres just minutes from historic Winchester, this extensively renovated modern farmhouse offers more than 7,500 square feet of finished living space across three distinct finished living areas, providing exceptional flexibility for multi-generational living, extended family, guests or those seeking dedicated private space. The main residence combines exposed wood beams, hardwood floors, abundant natural light and polished finishes with generous living and entertaining spaces. Expansive country and mountain views are framed from the upper deck and dining room through a wall of windows and exposed beams. The finished walk-out lower level creates a second private living area with its own full kitchen, offering additional flexibility and separation. Completed in 2025, the approximately 1,700-square-foot attached ADU provides a third fully finished living area with a separate entrance and its own living room, dining room, full kitchen, two bedrooms with en-suite baths and a half bath. Beneath the ADU, approximately 1,861 square feet of unfinished basement space provides substantial storage and future potential. A custom-designed office overlooks the pool and surrounding grounds, offering a dedicated work-from-home space with views of the property. Outdoor living is centered around the heated in-ground saltwater pool, large deck, patio and fire-pit area, complemented by extensive hardscaping for entertaining, dining and relaxing. The five-acre grounds combine mature woods, landscaped areas and open spaces with an established collection of fruit trees and berry bushes, including fig, cherry, pear, persimmon, peach, plum and blackberry. A finished 15' x 15' outbuilding with LVP flooring and a mini-split provides additional flexible space for an office, studio, gym or hobby room. The attached two-car garage features custom cabinetry, while the paved driveway offers ample parking. Major improvements include the 2025 ADU addition, Andersen replacement windows, main-level HVAC replaced in 2024, upper-level HVAC replaced in 2025, and updates to the roof, siding, pool equipment and more. With three finished living areas, substantial additional unfinished space, five private acres, mountain and country views, a heated saltwater pool and multiple flexible work and entertaining spaces, this distinctive property offers space and privacy while remaining conveniently located near Winchester and within walking distance of Valerie Hill Vineyard & Winery.

199 Oak Hill Dr, Stephens City

Listing courtesy of Re/Max Roots. Contact:

$1,035,000

MAIN LEVEL LIVING in an Idyllic Setting - Welcome to Stonymeade ! -2 acre Home Site in Winchester Virginia Base price shown is for the Boxwood MAIN LEVEL Owners Suite FLOORPLAN and we have many other plans including those with first floor primary suites, farmhouse kitchens, and multi-generational options. All homes include exceptional standard features including 10' main level ceilings, Hardwood floors, upgraded cabinetry and countertops, extensive trim package, and HardiePlank exterior. Plans are ready to be customized! DECORATED MODEL HOME located at 156 Covey Lane Winchester Va Open SATURDAYS and SUNDAYS from 11am to 5pm Call Sales Manager for Appointment

4 Beds ⋅ 4 Baths

MAIN LEVEL LIVING in an Idyllic Setting - Welcome to Stonymeade ! -2 acre Home Site in Winchester Virginia Base price shown is for the Boxwood MAIN LEVEL Owners Suite FLOORPLAN and we have many other plans including those with first floor primary suites, farmhouse kitchens, and multi-generational options. All homes include exceptional standard features including 10' main level ceilings, Hardwood floors, upgraded cabinetry and countertops, extensive trim package, and HardiePlank exterior. Plans are ready to be customized! DECORATED MODEL HOME located at 156 Covey Lane Winchester Va Open SATURDAYS and SUNDAYS from 11am to 5pm Call Sales Manager for Appointment

Lot 60 Gravenstein, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$1,400,000

Just over 20 acres zoned M1 with direct access to Rt 11 and within a 3 miles from interstate 81. Property has well maintained large brick rancher and detached 2 bay work shop.

2673 Martinsburg Pike, Stephenson

Listing courtesy of Re/Max Roots. Contact:

$1,050,000

Privately nestled at the end of a cul-de-sac, this exceptional custom-built estate offers privacy, craftsmanship, and sophisticated living on 6.65 acres surrounded by mature trees in a beautiful park-like setting. Built by the current owner with thoughtful attention to detail, this four-bedroom, five-full-bath residence offers an impressive blend of elegance, comfort, and versatility. A covered front porch welcomes you into a gracious interior featuring a turned staircase, Red Oak hardwood floors, and a formal dining room with crown molding and a charming bay window. The gourmet kitchen is designed for both everyday living and entertaining, featuring abundant solid-wood cabinetry with dovetail drawers, a large work island, desk area, double ovens, full-size refrigerator and freezer, gas drop-in cooktop, porcelain flooring, and under-cabinet lighting. The adjoining breakfast area opens to a scenic rear deck, while the family room features a gas fireplace. The main level includes a den which could become a main level guest suite. Upstairs, two spacious bedrooms share a Jack-and-Jill bath, a bedroom with ensuite, while the enormous Primary Suite offers a luxurious bath, custom walk-in closet with solid-wood organization, and access to a private covered balcony. The fourth-floor provides exceptional flexibility for a private office, studio, playroom, or additional living space. The partially finished basement features a large Great Room, a guest suite, and abundant unfinished storage. A three-car side-load garage adds convenience. Outdoor living is exceptional with a new DuxxBak composite deck, covered patio below, under-deck LED Edison-style lighting, and outdoor speakers controlled by Apple AirPlay. Additional highlights include Brazilian Cherry flooring in the office, six-zone HVAC, Ethernet/coax wiring throughout, dual-floor laundry hookups, surround-sound wiring, LeafFilter gutter protection with transferable lifetime warranty, hot-water circulation pump, RainSoft Reverse Osmosis and water softener systems, and plumbed air-compressor lines to the garage and basement. A truly distinctive property offering privacy, quality, and remarkable flexibility.

5 Beds ⋅ 5 Baths

Privately nestled at the end of a cul-de-sac, this exceptional custom-built estate offers privacy, craftsmanship, and sophisticated living on 6.65 acres surrounded by mature trees in a beautiful park-like setting. Built by the current owner with thoughtful attention to detail, this four-bedroom, five-full-bath residence offers an impressive blend of elegance, comfort, and versatility. A covered front porch welcomes you into a gracious interior featuring a turned staircase, Red Oak hardwood floors, and a formal dining room with crown molding and a charming bay window. The gourmet kitchen is designed for both everyday living and entertaining, featuring abundant solid-wood cabinetry with dovetail drawers, a large work island, desk area, double ovens, full-size refrigerator and freezer, gas drop-in cooktop, porcelain flooring, and under-cabinet lighting. The adjoining breakfast area opens to a scenic rear deck, while the family room features a gas fireplace. The main level includes a den which could become a main level guest suite. Upstairs, two spacious bedrooms share a Jack-and-Jill bath, a bedroom with ensuite, while the enormous Primary Suite offers a luxurious bath, custom walk-in closet with solid-wood organization, and access to a private covered balcony. The fourth-floor provides exceptional flexibility for a private office, studio, playroom, or additional living space. The partially finished basement features a large Great Room, a guest suite, and abundant unfinished storage. A three-car side-load garage adds convenience. Outdoor living is exceptional with a new DuxxBak composite deck, covered patio below, under-deck LED Edison-style lighting, and outdoor speakers controlled by Apple AirPlay. Additional highlights include Brazilian Cherry flooring in the office, six-zone HVAC, Ethernet/coax wiring throughout, dual-floor laundry hookups, surround-sound wiring, LeafFilter gutter protection with transferable lifetime warranty, hot-water circulation pump, RainSoft Reverse Osmosis and water softener systems, and plumbed air-compressor lines to the garage and basement. A truly distinctive property offering privacy, quality, and remarkable flexibility.

300 Clearview Dr, Clear Brook

Listing courtesy of RE/MAX Roots. Contact:

$1,350,000

Breathtaking mountain views, extensive renovations, and an exceptional detached garage and workshop! Enjoy panoramic 360-degree views of the Blue Ridge and Allegheny Mountains from this beautifully remodeled home, set on two landscaped acres with a newly paved driveway. Remodeled in 2025, the home showcases high-end finishes and thoughtful upgrades throughout, while a remarkable detached building completed in 2026 adds approximately 1,200 square feet of finished flex space to more than 3,500 square feet of total finished space. Inside the home, you'll find all-new American Woodmark cabinetry throughout, granite countertops, and Monogram stainless steel appliances. The family room features an elegant coffered ceiling and a custom coffee and wine bar with additional cabinetry, creating an inviting space for everyday living and entertaining. Additional improvements include luxury vinyl plank flooring, a sliding glass door, a new front door, and a new garage door. The newly constructed 2,800-square-foot detached building offers an impressive combination of finished flex space, garage capacity, and workshop functionality. The approximately 1,200-square-foot finished area includes two separate rooms, bathroom facilities, a sink, refrigerator, water softener, and additional cabinetry. Whether you envision guest accommodations, a private home office, studio, fitness area, or hobby space, this versatile area offers a wealth of possibilities. The building also features an oversized three-car garage with extensive LED lighting and dedicated EV charging service, providing generous room for vehicles, equipment, and storage. An adjoining 650-square-foot workshop includes a half bath, extensive built-in custom cabinetry, and dedicated 240V electrical service. Fully heated and air-conditioned, the workshop is ready for year-round projects, woodworking, automotive work, or other hobbies. For added functionality, the entire building is wired for generator service and equipped with a transfer switch for backup power. With breathtaking mountain scenery, extensive interior updates, a newly paved driveway, and a remarkable detached building offering finished flex space, garage capacity, and a fully equipped workshop, this property presents a unique opportunity to enjoy space, versatility, and modern convenience in a beautiful setting. Be sure to explore the attached 3-D tour!

4 Beds ⋅ 4 Baths

Breathtaking mountain views, extensive renovations, and an exceptional detached garage and workshop! Enjoy panoramic 360-degree views of the Blue Ridge and Allegheny Mountains from this beautifully remodeled home, set on two landscaped acres with a newly paved driveway. Remodeled in 2025, the home showcases high-end finishes and thoughtful upgrades throughout, while a remarkable detached building completed in 2026 adds approximately 1,200 square feet of finished flex space to more than 3,500 square feet of total finished space. Inside the home, you'll find all-new American Woodmark cabinetry throughout, granite countertops, and Monogram stainless steel appliances. The family room features an elegant coffered ceiling and a custom coffee and wine bar with additional cabinetry, creating an inviting space for everyday living and entertaining. Additional improvements include luxury vinyl plank flooring, a sliding glass door, a new front door, and a new garage door. The newly constructed 2,800-square-foot detached building offers an impressive combination of finished flex space, garage capacity, and workshop functionality. The approximately 1,200-square-foot finished area includes two separate rooms, bathroom facilities, a sink, refrigerator, water softener, and additional cabinetry. Whether you envision guest accommodations, a private home office, studio, fitness area, or hobby space, this versatile area offers a wealth of possibilities. The building also features an oversized three-car garage with extensive LED lighting and dedicated EV charging service, providing generous room for vehicles, equipment, and storage. An adjoining 650-square-foot workshop includes a half bath, extensive built-in custom cabinetry, and dedicated 240V electrical service. Fully heated and air-conditioned, the workshop is ready for year-round projects, woodworking, automotive work, or other hobbies. For added functionality, the entire building is wired for generator service and equipped with a transfer switch for backup power. With breathtaking mountain scenery, extensive interior updates, a newly paved driveway, and a remarkable detached building offering finished flex space, garage capacity, and a fully equipped workshop, this property presents a unique opportunity to enjoy space, versatility, and modern convenience in a beautiful setting. Be sure to explore the attached 3-D tour!

111 Pomme Cir, Stephens City

Listing courtesy of RE/MAX Roots. Contact:

$1,250,000

Welcome to the renowned and historic Barclays Run Farm located northwest of Winchester in the Gore area of the county. On the market for the first time in over 50 years so don’t miss your chance to own this one of a kind farm. Expansive acreage that stretches from Sinking Spring Lane to the base of Great North Mountain. This one of a kind offering features road frontage on Sinking Spring Lane of more than 4400 ft and creek frontage along a bubbling mountain stream of over 3000 ft. A spring fed pond adds to the beauty and character of this farm. Modern fencing divides up the high quality well managed livestock pastures and allows for grazing rotations. The fully restored circa 1700’s cottage features 2 bedrooms, 1 bathroom, over 960 square feet of living space, and a wrap-around covered porch. Elite panoramic views of the surrounding countryside can be seen from the higher elevations of the farm year round. Prime hunting opportunities for deer, turkey, bear, and small game. Conveniently located only minutes from US-50 Northwestern Pike. Protected from development by the Virginia Outdoors Foundation and a Wetlands Conservation Easement. Adjacent to the Potomac Appalachian Trail Club and Girl Scouts of Shawnee lands, both of which are in conservation easements. Hikers and walkers will enjoy the scenic Tuscarora Trail which runs through the upper part of this land. Zoned Rural Areas (RA) and a terrific location for your next country home and/or farming operation. A short drive from all the amenities and attractions Winchester has to offer. Only 2 hours from Washington DC, our nation's capital!

2 Beds ⋅ 1 Baths

Welcome to the renowned and historic Barclays Run Farm located northwest of Winchester in the Gore area of the county. On the market for the first time in over 50 years so don’t miss your chance to own this one of a kind farm. Expansive acreage that stretches from Sinking Spring Lane to the base of Great North Mountain. This one of a kind offering features road frontage on Sinking Spring Lane of more than 4400 ft and creek frontage along a bubbling mountain stream of over 3000 ft. A spring fed pond adds to the beauty and character of this farm. Modern fencing divides up the high quality well managed livestock pastures and allows for grazing rotations. The fully restored circa 1700’s cottage features 2 bedrooms, 1 bathroom, over 960 square feet of living space, and a wrap-around covered porch. Elite panoramic views of the surrounding countryside can be seen from the higher elevations of the farm year round. Prime hunting opportunities for deer, turkey, bear, and small game. Conveniently located only minutes from US-50 Northwestern Pike. Protected from development by the Virginia Outdoors Foundation and a Wetlands Conservation Easement. Adjacent to the Potomac Appalachian Trail Club and Girl Scouts of Shawnee lands, both of which are in conservation easements. Hikers and walkers will enjoy the scenic Tuscarora Trail which runs through the upper part of this land. Zoned Rural Areas (RA) and a terrific location for your next country home and/or farming operation. A short drive from all the amenities and attractions Winchester has to offer. Only 2 hours from Washington DC, our nation's capital!

251 Barclays Run Ln, Gore

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

$1,250,000

So many opportunities available with this commercial property. Traffic Counts: Hopewell Road: 4,500; Ik-81: 29,000; Route 11: 8,400. Allowed Uses: Landscape & Horticultural Services, Offices and Storage Facilities for Building Construction Contractors, Heavy Construction Contractors & Special Trade Contractors, Food, Beverage, and Tobacco Manufacturing excluding Seafood Product Preparation and Packaging and Animal Slaughtering and Processing, Textile Products and Textile Mill Products, Apparel Manufacturing, Veneer, Plywood, and Engineered Wood Product Manufacturing, Furniture and Related Production Manufacturing, Converted Paper Product Manufacturing, Printing, Publishing and Allied Industries, Pharmaceutical and Medicine Manufacturing, Plastics and Rubber Products Manufacturing including Footwear Manufacturing, Miscellaneous Manufacturing, Concrete Block and Brick and Related Products, Fabricated Metal Products Manufacturing, excluding Coating, Engraving and Allied Services, Ammunition (except for small arms), Ordnance and Accessories, Machinery Manufacturing and Computer and Electrical Product Manufacturing, Electrical Equipment, Appliance & component manufacturing, storage batteries and primary battery manufacturing, transportation Equipment manufacturing, self-service storage facilities, Truck or fleet maintenance facilities, Wholesale Trade, Food Services, Restaurants and other eating places, Truck, Utility Trailer, and RV Rental and Leasing, General Automotive, Motorcycle and Truck Repair, Services and Parking, Machinery Cleaning, Technical and Trade Schools, Linen Supply & Dry cleaning and Laundry Services except Coin Operated Laundries and more. Taxes and Tax Assessments are approximate as property is in Land Use. This parcel can also be purchased with 32.918 acres for an additional $3,500,000

Hopewell, Clear Brook

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

$1,130,000

Priced well below market value for a quick sale, this extraordinary 34-acre retreat offers a rare combination of natural beauty, privacy, versatility, and exceptional value. Surrounded by rolling meadows, serene woodlands, and picturesque mountain views, the property features a stunning log home, a separate guest cottage, multiple outbuildings, and thoughtfully designed spaces for entertaining, recreation, farming, or a home-based business. The main residence welcomes you with an inviting open floor plan, soaring vaulted ceilings, gleaming hardwood floors, and an abundance of natural light. A magnificent stone masonry fireplace creates a warm and impressive focal point for the main living area. Relax on the covered front porch while enjoying peaceful sunsets, or step onto the expansive rear deck for morning coffee, outdoor dining, and panoramic views of the surrounding countryside. The thoughtfully designed split-bedroom floor plan provides privacy and comfort. The spacious primary suite serves as a peaceful sanctuary and features a beautifully remodeled, spa-inspired bathroom with a walk-in shower. Two additional bedrooms offer convenient access to another remodeled full bathroom. The finished walk-out lower level is ideal for recreation and everyday living. It includes a large family room with luxury vinyl plank flooring and a cozy wood stove, two versatile bonus rooms that may be used as guest rooms, offices, hobby rooms, or fitness spaces, as well as a third full bathroom and laundry area. A separately constructed guest cottage offers approximately 1,300 square feet of additional living and entertaining space. The cottage features a spacious great room warmed by a wood stove, a fully equipped kitchen, a comfortable bedroom, and a full bathroom. Wraparound wood decks provide the perfect setting for guests to enjoy fresh air, sunrise and sunset views, and the peaceful natural surroundings. The cottage is ideal for extended family, overnight visitors, retreats, or private gatherings. The detached workshop and adjoining flexible bonus room offer endless possibilities. The space may be transformed into a large dining or event area, studio, organized workshop, storage facility, or home-business headquarters. A chicken coop brings the charm of country living to life, providing an opportunity to gather fresh eggs and enjoy caring for animals. Additional outbuildings offer generous space for equipment, hobbies, agricultural use, and storage. A covered outdoor pavilion with bench seating and an outdoor kitchen creates an exceptional setting for entertaining, celebrations, and family gatherings. The owner has invested more than $500,000 in constructing, remodeling, and completing improvements throughout the main residence, guest cottage, workshop, sheds, pavilion, and surrounding property. Despite its peaceful country setting, the property is conveniently located approximately 10 minutes from I-81 and 20 minutes from the shops, restaurants, and attractions of downtown Strasburg. Here, the convenience of modern living meets the tranquility of a private countryside getaway. Furniture in the guest cottage, the tractor, and farming equipment convey with the property. Come experience the beauty, versatility, and remarkable value of this exceptional 34-acre retreat.

5 Beds ⋅ 4 Baths

Priced well below market value for a quick sale, this extraordinary 34-acre retreat offers a rare combination of natural beauty, privacy, versatility, and exceptional value. Surrounded by rolling meadows, serene woodlands, and picturesque mountain views, the property features a stunning log home, a separate guest cottage, multiple outbuildings, and thoughtfully designed spaces for entertaining, recreation, farming, or a home-based business. The main residence welcomes you with an inviting open floor plan, soaring vaulted ceilings, gleaming hardwood floors, and an abundance of natural light. A magnificent stone masonry fireplace creates a warm and impressive focal point for the main living area. Relax on the covered front porch while enjoying peaceful sunsets, or step onto the expansive rear deck for morning coffee, outdoor dining, and panoramic views of the surrounding countryside. The thoughtfully designed split-bedroom floor plan provides privacy and comfort. The spacious primary suite serves as a peaceful sanctuary and features a beautifully remodeled, spa-inspired bathroom with a walk-in shower. Two additional bedrooms offer convenient access to another remodeled full bathroom. The finished walk-out lower level is ideal for recreation and everyday living. It includes a large family room with luxury vinyl plank flooring and a cozy wood stove, two versatile bonus rooms that may be used as guest rooms, offices, hobby rooms, or fitness spaces, as well as a third full bathroom and laundry area. A separately constructed guest cottage offers approximately 1,300 square feet of additional living and entertaining space. The cottage features a spacious great room warmed by a wood stove, a fully equipped kitchen, a comfortable bedroom, and a full bathroom. Wraparound wood decks provide the perfect setting for guests to enjoy fresh air, sunrise and sunset views, and the peaceful natural surroundings. The cottage is ideal for extended family, overnight visitors, retreats, or private gatherings. The detached workshop and adjoining flexible bonus room offer endless possibilities. The space may be transformed into a large dining or event area, studio, organized workshop, storage facility, or home-business headquarters. A chicken coop brings the charm of country living to life, providing an opportunity to gather fresh eggs and enjoy caring for animals. Additional outbuildings offer generous space for equipment, hobbies, agricultural use, and storage. A covered outdoor pavilion with bench seating and an outdoor kitchen creates an exceptional setting for entertaining, celebrations, and family gatherings. The owner has invested more than $500,000 in constructing, remodeling, and completing improvements throughout the main residence, guest cottage, workshop, sheds, pavilion, and surrounding property. Despite its peaceful country setting, the property is conveniently located approximately 10 minutes from I-81 and 20 minutes from the shops, restaurants, and attractions of downtown Strasburg. Here, the convenience of modern living meets the tranquility of a private countryside getaway. Furniture in the guest cottage, the tractor, and farming equipment convey with the property. Come experience the beauty, versatility, and remarkable value of this exceptional 34-acre retreat.

2121 S Pifer Rd, Star Tannery

Listing courtesy of Grace Home Realty & Investment. Contact:

$1,315,000

Opportunities like this are becoming increasingly difficult to find within the growing Winchester market. Strategically positioned along the Rt. 522 corridor, this 2.23-acre commercial property offers the ideal combination of visibility, accessibility, flexibility, and future potential. Surrounded by established medical facilities, national businesses, residential communities, and expanding commercial infrastructure, the property is well positioned for a wide range of development opportunities. Currently zoned B2 and RP, the site supports numerous commercial applications including hospitality, medical and professional offices, automotive-related services, personal service businesses, self-storage, and additional commercial uses. The property also presents future rezoning possibilities, providing long-term flexibility for investors and developers seeking to maximize the site’s potential. Located just minutes from Winchester Medical Center with immediate access to Highway 37 and Interstate 81, the property benefits from strong regional connectivity and consistent traffic exposure within Frederick County’s most active commercial corridors. Whether envisioned as a medical campus, hospitality site, professional office complex, or mixed commercial development, this property offers the location, infrastructure, and flexibility to support a wide range of future possibilities.

N Frederick Pike, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$1,200,000

Prime Corner Lot at Front Royal Pike & Airport Road - High-Visibility Winchester Location Positioned at one of Winchester's most traveled intersections, this corner lot offers exceptional visibility with a combined 19,800 vehicles passing daily. Located at the signalized intersection of Front Royal Pike (U.S. 522) and Airport Road, the site provides strong traffic flow, and strategic positioning within a rapidly developing commercial corridor. The property is currently zoned RP (Residential Performance), offering flexibility for future development opportunities subject to rezoning or special use approvals. Its corner configuration, frontage on two well-traveled roads, and proximity to major commercial activity make it an ideal candidate for retail, service, office, or mixed-use concepts. Whether for long-term investment or immediate planning, this site delivers the visibility, access, and growth potential that developers and businesses look for in the Winchester market.

699 Front Royal Pike, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$1,125,000

Welcome to the renowned and historic Barclays Run Farm located northwest of Winchester in the Gore area of the county. On the market for the first time in over 50 years so don’t miss your chance to own this one of a kind farm. Expansive acreage that stretches from Sinking Spring Lane to the base of Great North Mountain. This one of a kind offering features road frontage on Sinking Spring Lane of more than 4400 ft and creek frontage along a bubbling mountain stream of over 3000 ft. A spring fed pond adds to the beauty and character of this farm. Modern fencing divides up the high quality well managed livestock pastures and allows for grazing rotations. The fully restored circa 1700’s cottage features 2 bedrooms, 1 bathroom, over 960 square feet of living space, and a wrap-around covered porch. Elite panoramic views of the surrounding countryside can be seen from the higher elevations of the farm year round. Prime hunting opportunities for deer, turkey, bear, and small game. Conveniently located only minutes from US-50 Northwestern Pike. Protected from development by the Virginia Outdoors Foundation and a Wetlands Conservation Easement. Adjacent to the Potomac Appalachian Trail Club and Girl Scouts of Shawnee lands, both of which are in conservation easements. Hikers and walkers will enjoy the scenic Tuscarora Trail which runs through the upper part of this land. Zoned Rural Areas (RA) and a terrific location for your next country home and/or farming operation. A short drive from all the amenities and attractions Winchester has to offer. Only 2 hours from Washington DC, our nation's capital!

251 Barclays Run Ln, Gore

Listing courtesy of Whitetail Properties Real Estate, LLC. 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:

$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:

$1,150,000

Four months build time from contract. Foundation dug and construction to begin soon. To have finished basement. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 3,100 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck that wraps all the way around the side of the house.perfect for grilling (quick connect propane) and sunbathing. Walk-Out Access: The finished basement boasts convenient double-door walk-out access, opening onto a full-length concrete patio that spans under all decking, offering versatile entertainment possibilities. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community.

4 Beds ⋅ 4 Baths

Four months build time from contract. Foundation dug and construction to begin soon. To have finished basement. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate, brand-new residence, meticulously designed with a flowing 3,100 sq. ft. open floor plan. The builder has redefined "standard features," integrating premium elements throughout the home that others typically label as costly upgrades. Key Features & Elegant Finishes: Striking Curb Appeal: A distinguished full brick front complemented by durable cement siding creates a timeless exterior, highlighted by a large, welcoming concrete front porch and lead walk. Exquisite Main Level: Rich, stained Early American hardwood flooring flows seamlessly across the entire main level, excluding the elegant tiled bathrooms and laundry room, creating a warm, inviting atmosphere. Seamless Indoor/Outdoor Entertaining: Step through to your private outdoor oasis. A covered and screened deck provides an ideal spot for year-round relaxation, extending onto an attached open deck that wraps all the way around the side of the house.perfect for grilling (quick connect propane) and sunbathing. Walk-Out Access: The finished basement boasts convenient double-door walk-out access, opening onto a full-length concrete patio that spans under all decking, offering versatile entertainment possibilities. This exquisite home represents a unique blend of craftsmanship, luxury, and exclusivity. Don't miss the chance to claim your spot in this premier community.

121 Keval Gyan Way, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$1,400,000

Great highway exposure exposure to state route 37 the bypass around the West side of Winchester and and 5222 north or North Frederick Pike entrance at a signalized intersection

1667 N Frederick Pike, Winchester

Listing courtesy of Colony Realty. Contact:

$1,471,000

PRICE REDUCED!! We have a contract in Due Diligence! However, owner is still accepting good offers! Pad site G setting back from Senseny Road adjacent to the Orrick Commons Shopping Center is a prime site for a Grocery Store and the residents in the area are ANXIOUS to get a store to service their needs. Great location with easy access AND an entrance directly from a 55 and older community that is FULLY BUILD out with single family homes and an apartment building! Valley Health has a medical office just in front of the lots facing Senseny Road. This could be a excellent self-storage location, also. Near McDonalds and CVS Pharmacy. Lots of roof tops and high traffic count in the area midway between route 7 east (1 mile) and route 50 east (2 miles). Access to the lot from Greenwood and Senseny road in the Orrick Commons Center. 2 miles from Winchester City limits on Senseny Road at a lighted intersection. There are single family developments throughout the area of Greenwood and Senseny road areas with sale prices for homes starting in the $400,000.00 range! This intersection has two grade schools and a high school with 3 miles of the location. This is a great opportunity for a grocery store to gain support for the local community!

Grocery Unit LOT G, Winchester

Listing courtesy of Commercial Specialists. Contact:

$1,471,000

PRICE REDUCED!! Owners are looking for reasonable offers. Pad site G setting back from Senseny Road adjacent to the Orrick Commons Shopping Center. Great retail, restaurant, office location. ALSO SELF-STORAGE!!! Near McDonalds and CVS Pharmacy. Lots of roof tops and high traffic count in the area midway between route 7 east (1 mile)and route 50 east (2 miles). Access to the lot from Greenwood and Senseny road in the Orrick Commons Center. 2 miles from Winchester City limits on Senseny Road. Access to the 55 and older communities being constructed in the area, One multi-level apartments and 33 acres of single family and town homes beside the pad sites that is nearing built out. Apartment building now leasing units. This property calls out for self storage with not only the 55 and older community but new housing on Greenwood Road with $600,000 homes being build! The land is flat and ready to develop with utilities on site for hookup!

Grocery Ave Unit LOT G, Winchester

Listing courtesy of Commercial Specialists. Contact:

$1,300,000

Unlock the potential of a timeless landmark with the Wayside Inn, a historic gem nestled in the heart of Middletown, Virginia. This unique property not only boasts a rich history dating back to the 18th century but also offers 22 suites all with bathrooms, 3 bars (tavern, bourbon & Speakeasy, The RED HAT), huge entertaining space for events. This is a prime commercial opportunity with an expansive land for expansion. Just under 4 acres zoned B1. With 4 acres of commercially-zoned land at your disposal, envision the expansion possibilities that could elevate this historic landmark into a thriving hub of activity. Take advantage of the ample space to create a vibrant commercial district that complements the historic character of the Wayside Inn, making it a destination for locals and tourists alike. Situated in the picturesque Shenandoah Valley, the Wayside Inn offers a scenic backdrop that enhances the allure of any commercial venture. The expansive grounds provide ample room for outdoor amenities, gardens, or additional structures to further enhance the property's appeal. Benefit from the strategic location of Middletown, with easy access to major transportation routes. The Wayside Inn's proximity to popular attractions, historic sites, and a supportive local community makes it an ideal location for a successful and sustainable business venture. Don't miss the chance to own a piece of history with a promising future. The Wayside Inn presents a rare investment opportunity where historic charm meets commercial potential. Whether you're an entrepreneur seeking a unique venture or a developer with a vision, this property is your canvas to create something extraordinary. Seize the moment and transform the future of the Wayside Inn. Embrace the legacy, write the next chapter, and make this historic landmark a cornerstone of Middletown's thriving community. Fully running and doing great, we have changed management and its now positive cash flow. its prime for an owner occupant. call for details and appointments. Open to lease option and owner financing available. Kitchen and tavern are leased. Have grants applied for in the millions to renovate it. Have insurance claim coming for a new roof as well.

7783 Main St, Middletown

Listing courtesy of RE/MAX Allegiance. Contact:

$1,000,000

10 acres, Zoned B2/ Well located in fast-growing Channing Drive - Senseny Road corridor, east of Winchester. Lots of rooftops - Contiguous to newer elementary school. Water and sewer located at the property. Road frontage on three roads.

Channing Drive, Winchester

Listing courtesy of Colony Realty. Contact:

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