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314 N Braddock St, Winchester
$1,250,000
Located in the heart of the historic downtown district, this versatile B1-zoned property offers a rare blend of immediate income and long-term upside. The building features approximately 7,000 SF of office space complemented by 2,000 SF of ground-level shop, supported by 12 on-site parking spaces, important in the urban core. Beyond its current use, the property presents exceptional redevelopment potential, it could be conversion to nine residential units on a single floor and the ability to add up to two additional stories, creating a total of 27 residential units. Ideal for investors or developers seeking a high-visibility downtown location with historic character, flexible zoning, and significant value-add potential.

314 N Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

Lot 7 Cedar Creek Grade, Winchester
$689,000
The seller has made a significant price adjustment to better align the property with current market conditions, creating an outstanding opportunity for buyers. With the new pricing, this property offers exceptional value and is positioned for serious consideration. If you've previously considered this property, now is the time to take another look. ** House and 5+ acres also offered for sale. Reference MLS# VAFV2045418 Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved Conditional Use Permit. 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. An exceptional opportunity for agricultural use, a private estate, or a thoughtfully planned preservation property in one of the Shenandoah Valley’s most sought-after locations.

Lot 7 Cedar Creek Grade, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Northwestern Pike, Winchester
$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:

832 Winder Ct, Winchester
$465,000
3 Beds ⋅ 2 Baths
Listed below recent appraised value. All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, and new carpet in all bedrooms. Tile flooring has been thoughtfully retained in the kitchen, entry, and guest bath. Recessed lighting has been added to the main living area, along with multiple updated light fixtures, creating a bright and welcoming feel. The kitchen features a breakfast nook with a bay window and now includes custom built pantry storage, while the living room has been enhanced with a custom built-in with integrated lighting. A former bar area was removed and replaced with a large storage closet, significantly improving functionality. The primary bathroom has been fully gutted and completely redesigned, featuring a modern walk-in shower, contemporary fixtures, and an aging-in-place–friendly layout with grab bars and improved accessibility. The sunroom has been reconfigured for better flow, with the original sliding doors removed, a new cased opening added, and HVAC extended to the space, allowing it to be enjoyed year-round. A rear deck extends the living space outdoors. Exterior improvements include over $10,000 in rear landscaping designed to buffer Meadow Branch Avenue, featuring Crepe Myrtles, Emerald Green Arborvitae, and Hollies. A crawlspace fan/radon-style ventilation system has also been installed. Situated on a cul-de-sac and conveniently located near hospitals, shopping, dining, fitness facilities, walking trails, coffee shops, and Old Town Winchester. HOA covers lawn maintenance, snow removal, pool, and tennis courts. Not a 55+ community. Homes offering this level of care, thoughtful upgrades, and low-maintenance living in this location are rarely available.

832 Winder Ct, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

To Be Built-Homesite 18 Williamson Road, Winchester
$598,990
3 Beds ⋅ 2 Baths
TO BE BUILT – This home has not been constructed yet. Photos are of a similar model and may show optional features. Appointment at model home – 154 Williamson Rd. Price reflects base price plus options. Estimated delivery timeline is approximately 6–7 months. The Drexel offers generous living space in a beautifully designed ranch home featuring 3 bedrooms and 3 bathrooms, with approximately 3,213 finished square feet. A standout feature is the optional basement bedroom with a full bath, providing the perfect space for guests, extended family, or added privacy. This home is designed for convenient main-level living, including a private owner’s suite with a walk-in closet and en-suite bathroom, two additional full bathrooms on the main level, and a 2-car garage. A versatile flex room can easily function as a home office, formal dining room, or den, adapting to your lifestyle. At the heart of the Drexel is a spacious open-concept family room that flows seamlessly into the kitchen and breakfast nook, creating an inviting space for everyday living and entertaining. Outdoor living is just as appealing, with an included covered deck—perfect for relaxing or hosting while enjoying the outdoors.

To Be Built-Homesite 18 Williamson Road, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

TO BE BUILT - To Be Built Williamson Rd, Winchester
$529,990
3 Beds ⋅ 2 Baths
THIS IS A TO-BE-BUILT HOME THAT CAN BE BUILT ON ANY AVAILABLE HOMESITE. If the homesite shown is no longer available, we have other homesites to choose from. The Avalon is a stunning 3-bedroom, 2-bath single-family home offering up to 2,538 square feet of thoughtfully designed living space, with the option to add a 4th bedroom in the finished lower level. Designed for comfortable main-level living, the Avalon features an open-concept floor plan that brings together a spacious great room, bright and airy kitchen, and welcoming breakfast area. The main level includes three bedrooms and two full baths, with the flexibility to transform one of the bedrooms into a versatile flex space—perfect for a home office or den. Personalize the Avalon to fit your lifestyle with available options such as a sunroom, finished basement with an additional bedroom, and three-car garage. Make the Avalon truly your own by choosing your homesite, finishes, and options to create a home that fits your lifestyle.

TO BE BUILT - To Be Built Williamson Rd, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

403 Keval Gyan Way, Winchester
$950,000
3 Beds ⋅ 3 Baths
Four months build time from contract. 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 Permitted and built time 4 months. 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 perfect for grilling and sunbathing. The Ultimate Future Lower Level Retreat: basement opening onto a full-length concrete patio that spans the entire back of the house, 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. Full side deck and associated patio are optional

403 Keval Gyan Way, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Lot 11 Keval Gyan, Winchester
$899,900
3 Beds ⋅ 2 Baths
Four months build time from contract. 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 (new PIN OAK model); 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 2,488 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 perfect for grilling and sunbathing. 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.

Lot 11 Keval Gyan, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Lot 10 Desant, Winchester
$849,900
5 Beds ⋅ 3 Baths
Four month build time from contract. 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 a large family living in this immaculate, brand-new residence, meticulously designed with a flowing over 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. Rich, stained Early American hardwood flooring flows seamlessly across the entire home, 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 perfect for grilling and sunbathing. 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.

Lot 10 Desant, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

121 Keval Gyan Way, Winchester
$1,150,000
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:

Renaissance Dr, Winchester
$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:

Renaissance Dr, Winchester
$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:

108 Martin Dr, Winchester
$260,000
2 Beds ⋅ 1 Baths
Attention investors! Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large windows that let in plenty of natural light. A roomy laundry area provides additional functionality and leads directly to the backyard. This move-in ready home makes it the perfect property either for the seasoned investor or someone just starting to build their investment portfolio. Tenant in place, lease through 7/19/2027.

108 Martin Dr, Winchester

Listing courtesy of Samson Properties. Contact:

Northwestern Pike, Winchester
$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:

White Pine Ln, Winchester
$54,900
BUILD YOUR HOME ON 3 WOODED ACRES IN FREDERICK COUNTY. If you have been searching for land with room to spread out, privacy and no HOA, this 3 acre wooded parcel offers an opportunity to bring your plans to life. A 3 bedroom septic certification is already in place, providing an important step toward planning your future home. Enjoy a peaceful natural setting with mountain views while remaining within reach of Winchester and area conveniences. Zoned RA and offering approximately 3 acres, the property provides space for a private homesite and outdoor living surrounded by nature. Whether you are planning to build now or looking for land for the future, this is an opportunity to secure acreage in Frederick County at an attractive price. Property Highlights: 3 ACRES
 NO HOA
 3 BEDROOM SEPTIC CERTIFICATION
 WOODED SETTING
 MOUNTAIN VIEWS
 FREDERICK COUNTY Bring your builder and explore the possibilities.

White Pine Ln, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

125 Cheshire Ct, Winchester
$415,000
4 Beds ⋅ 4 Baths
Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-sac on the east side of Winchester. Conveniently located to Rt 7 and I-81 and historic downtown Winchester. The 3-level townhouse backs to a wooded tree area and has a fenced rear yard. New luxury vinyl floor installed in majority of the home. As you enter, you will be welcomed into a large foyer with hardwood floors. The entry level (main level) offers a large bedroom, full bath, family room, coat closet, and two storage closets. From the family room your eye is drawn to the spacious fenced yard. On the upper level 1 you will find a gourmet kitchen with a large island, stainless steel appliances, and granite countertops. The kitchen offers a large eating area. A deck with stairs to the yard adjoins the kitchen. Off the kitchen is an oversized sun-filled living area with an electric fireplace. The upper level 2 offers the primary bedroom and bath and 2 large bedrooms and full bath. Laundry room is conveniently located on the upper level.

125 Cheshire Ct, Winchester

Listing courtesy of Re/Max Roots. Contact:

115 Stetson St, Winchester
$799,900
3 Beds ⋅ 3 Baths
No HOA and Completely Finished!!! Great opportunity to own this brand-new, move-in ready ranch home situated on 2.82 beautiful acres! Conveniently located near shopping and commuter routes to Winchester, Martinsburg, and Northern Virginia, this home offers the perfect blend of privacy and accessibility. Designed with an open-concept layout and a desirable split-bedroom floor plan, the home features striking front board and batten siding that creates exceptional curb appeal. The spacious primary suite includes a large walk-in closet and a luxurious 6-foot walk-in shower with Glass Surround. A private main-level office provides the ideal space for working from home. The chef's kitchen is thoughtfully appointed with quartz countertops, tile backsplash, a large center island, stainless steel appliances including double ovens, and quality cabinetry with soft-close drawers and doors. The bright sunroom fills the home with natural light, while luxury vinyl plank flooring extends throughout much of the main level. A convenient laundry room with utility sink adds everyday functionality. The enormous unfinished basement is already plumbed for a future bathroom, and the HVAC system is sized to accommodate a finished lower level, offering outstanding expansion potential. Additional features include a two-car side-entry garage, covered front porch with a concrete sidewalk, rear patio, and a beautiful lot enhanced by mature hardwood trees. Don't miss your chance to own this exceptional new home!

115 Stetson St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

1049 Laurel Grove Rd, Winchester
$749,900
3 Beds ⋅ 3 Baths
This property delivers an exceptional mix of seclusion, comfort, and natural beauty. This custom-built 3-bedroom, 3-bath home rests on a private, wooded lot with sweeping mountain views, offering a tranquil atmosphere while remaining close to everyday amenities. The main-level primary suite serves as a peaceful retreat, featuring an elegant walk-in shower and a soothing soaking tub. Two additional main-floor bedrooms provide generous space and storage, paired with an updated full hall bath. Rich hardwood floors, a welcoming fireplace, and a bright sunroom that opens to the patio create a warm, cohesive flow throughout the main living areas. The kitchen is highlighted by granite countertops, ample cabinetry, and abundant natural light. The walk-out basement enhances the home’s flexibility, offering space ideal for a family room, office, gym, or guest accommodations, complete with a full bath. An enclosed breezeway leads to the oversized garage, a standout feature with exceptional storage capacity, workshop potential, and room for equipment or multiple vehicles. The usable, unrestricted acreage is another major advantage—perfect for animals, gardening, outbuildings, or simply enjoying wide-open space without limitations. This is a true nature-filled haven paired with convenient access to shopping, dining, and schools. Homes offering this combination of privacy, functional land, and an oversized garage are hard to find. Schedule your tour today!

1049 Laurel Grove Rd, Winchester

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

180-190 Prosperity Dr, Winchester
$7,200,000
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:

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