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Grocery Unit LOT G, Winchester
$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:

Grocery Ave Unit LOT G, Winchester
$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:

N Frederick Pike, Winchester
$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:

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:

1022 Heth Pl, Winchester
$1,239,000
4 Beds ⋅ 8 Baths
This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy. Inside, you will find a stunning kitchen with top-of-the-line appliances and pull-out drawers throughout the cabinets. The great room is a 2 story ceiling and fireplace leading to the deck and wet bar with ice machine and wine racks. The main level office has a full bath attached if you would like to use it as a main level bedroom. The living and dining rooms are open to each other leading to a sunroom off the deck. The primary bedroom as a gas fireplace, a balcony , 2 walk in closets and an updated spa like bathroom. The second bedroom has it's own bath and the 3rd and 4th bedrooms share a full bath with updated tile and floors. The basement also has a fireplace, a full bath, exercise room and plenty of storage. The pool room (in the basement leading to the pool) has a refrigerator, storage for towels and a 1/2 bath. The 3 car garage has a ton of storage, as the original kitchen cabinets are on the wall...This home is truly a showcase!

1022 Heth Pl, Winchester

Listing courtesy of Samson Properties. Contact:

699 Front Royal Pike, Winchester
$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:

Lot 7 and 4035 Cedar Creek Grade, Winchester
$1,164,000
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:

Lot 1 Keval Gyan, 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.

Lot 1 Keval Gyan, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

1030 Breckinridge Ln, Winchester
$1,100,000
6 Beds ⋅ 6 Baths
Welcome to this inviting, beautifully maintained 6-bedroom, 4-full-bathroom, 2-half-bathroom all-brick home in the desirable Meadow Branch subdivision in Winchester, Virginia. Offering over 6,000 square feet of finished living space, this impressive residence combines generous room sizes, timeless construction, exceptional storage, and comfortable living spaces designed for both everyday life and entertaining. Set on approximately half a lot, the property features a welcoming U-shaped driveway, mature landscaping, and wonderful curb appeal. With no HOA, you have the freedom and flexibility to enjoy the property on your terms. Inside, the home offers an abundance of built-in cabinetry, custom closet storage, and storage solutions throughout, making it easy to keep even a large household organized. The spacious layout provides plenty of room for family, guests, work-from-home spaces, hobbies, and entertaining. The walk-out basement adds another valuable level of living and recreational space, with convenient access to the outdoors. With six bedrooms, four full bathrooms, and two half bathrooms, there is plenty of flexibility for a growing family or those who simply want room to spread out. Meticulously cared for and move-in ready, this substantial brick home offers the space, storage, privacy, and location that are increasingly hard to find. Enjoy the established beauty of Meadow Branch while being conveniently located in Winchester, with easy access to shopping, dining, schools, commuter routes, and all that the area has to offer. A rare opportunity to own a spacious, established home with exceptional storage and flexibility in one of Winchester's sought after communities.

1030 Breckinridge Ln, Winchester

Listing courtesy of Samson Properties. Contact:

1010 Breckinridge Ln, Winchester
$1,065,000
5 Beds ⋅ 6 Baths
Winchester’s established Meadow Branch neighborhood invites you to the first ever offering of 1010 Breckinridge Lane! A thoughtfully designed residence offering generous living space of over 5500sqft, refined architectural details which include a great room with stunning floor to ceiling windows receiving abundant natural light to create an open, inviting atmosphere, while fine trim work, custom built-ins, and carefully considered finishes give the home a sense of quality. At the center of the home, the modern kitchen combines custom white cabinetry, granite countertops, stainless-steel appliances, dual ovens, and ample workspace for everyday cooking and entertaining. The 5 bedroom 5.5 bath traditional floor plan provides both comfortable gathering areas and more intimate spaces for formal dining, working from home, or hosting large gatherings. The upper level is anchored by a spacious primary suite, while the main-level in-law suite offers comfortable accommodation for extended family, long-term guests, or those seeking single-level living. A full finished basement expands the home’s versatility with additional space for recreation, entertainment, fitness, hobbies, or private guest use. Outside, a large deck overlooks mature landscaping and connects to a terraced patio designed for outdoor dining and entertaining. Established trees create privacy while preserving the convenience of an in-town Winchester location. A three-car side load garage provides substantial parking, workshop, and storage capacity, completing a residence that balances comfort, privacy, and everyday functionality all on a private .71 acre lot.

1010 Breckinridge Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

38 Rouss Ave, Winchester
$995,000
Yost Building Positioned in the heart of downtown, this distinguished office building—formerly the executive wing of F&M National—offers an outstanding opportunity for businesses seeking a prestigious and highly walkable location. Multiple suite sizes are available, making it ideal for professional firms, government-adjacent services, or organizations looking to establish a prominent presence in the city’s core. Situated adjacent to City Hall and steps from the Historic Walking Mall, this property provides unparalleled convenience for employees and clients alike. Within a quick walk, you’ll find the Frederick County Administrative Buildings, the Courthouse, and numerous public parking structures, ensuring seamless access for daily operations. With its prime location, flexible floorplan offerings, and proximity to key civic and commercial amenities, this downtown office building represents a rare opportunity to secure space in one of the most strategic and sought-after areas of the city. ALSO LISTED FOR LEASE

38 Rouss Ave, Winchester

Listing courtesy of Colony Realty. Contact:

3052 Valley Ave Unit 200, Winchester
$995,000
Prime office or retail space in Winchester’s Opequon Center featuring ample parking, snow removal, and landscaping services. These are condominium units with 2 separate spaces available: Suite 200 and Suite 201. This is an ideal situation for the owner/investor who occupies one unit for their office or business and leases the second unit as an income-producing investment. Suite 200 will soon be vacant, and Suite 201 is leased by One Source, Inc. which is a company providing human resource recruitment, background investigation, and identity verification services. These spaces are on the second floor with elevator service. Each of the two spaces has a floor area of approximately 2,500 SF. These condominiums are located in a professionally managed office and business park with reputable neighbors such as medical offices, a real estate firm, an orthodontist, and a physical therapist.

3052 Valley Ave Unit 200, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

236 Delmas Trl, Winchester
$984,900
4 Beds ⋅ 4 Baths
Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking mountainous backdrop. Built in 2019, this home boasts an impressive 3,317 square feet of meticulously designed living space, perfect for those who appreciate both elegance and functionality. The kitchen is a culinary dream, featuring high-end appliances including a built-in microwave, electric cooktop, and self-cleaning wall oven, all complemented by ample table space and a cozy eat-in area. Beautiful built-ins and walk-in closets provide both style and practicality, ensuring that every inch of this home is utilized to its fullest potential. The main level also features a thoughtfully designed entry-level bedroom and a luxurious bathroom with a walk-in shower, catering to convenience and comfort. Ascend to the upper levels to find two additional spacious bedrooms with its own spacious full bathroom, promising tranquility and relaxation. The fully finished basement offers endless possibilities, a forth bedroom or office with a full bathroom, daylight windows and walkout access to the serene outdoors, making it perfect for a home gym, media room, or additional living space. There is also an expansive storage area for all your needs. Outside, the property spans over 5 acres of beautifully cleared and landscaped grounds, providing a private oasis that backs to lush trees. Enjoy the tranquility of nature from your beautiful wrap-around porch, where you can unwind and soak in the stunning mountain views. The lower level offers a concrete area with a hot tub. There is a beautiful large detached 3 car garage for all of your cars, motorcycles or mowers. This home is not just a residence; it's a lifestyle. Experience the luxury of modern living in a serene mountain setting, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. With its exceptional features and prime location, this property is a rare gem that promises to be a cherished sanctuary for years to come. Generator hook up wired for electric outages and Outside water bib running hot and cold water for dog baths and other use. Come see it today!

236 Delmas Trl, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Lot 13 Keval Gyan, 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

Lot 13 Keval Gyan, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

950 Stony Hill Rd, Winchester
$925,000
PLEASE NOTE THAT THERE IS AN ELECTRIC FENCE. PLEASE MAKE SURE IT'S CLOSED BEHIND YOU WHEN ENTERING AND EXITING PROPERTY. MUST HAVE AN APPOINTMENT AND BE ACCOMPANIED BY AN AGENT TO SEE THIS PROPERTY. A truly rare opportunity to own over 150 acres in Frederick Co., VA , just a few miles west of the scenic Shenandoah Valley—where rolling pasture, privacy, and possibility come together. 950 Stony Hill Rd. offers a stunning blend of open farmland and natural beauty. With significant portions of the land farmable, this property is perfectly suited for agricultural use, equestrian pursuits, or creating a remarkable private estate or multi-generational retreat. Development may be possible. Any Purchaser needs to do their own research for their desired use(s). Existing features include available electric and a former tenant house (not livable). This property is 15 minutes from Historic Old Town Winchester, featuring a wide array of shopping, dining and entertainment options. Year-round outdoor activity pursuits are possible on property or nearby, including, golfing, hiking, fishing, kayaking and even skiing within 2 to 2.5 hours. Must be accompanied by Agent and have appointment to tour property. Livestock on property. D0 NOT ENTER OLD TENANT HOUSE. IT'S NOT SAFE. ENTRY TO STUCTURE IS STRICTLY FORBIDDEN. Private property. No drive-bys.

950 Stony Hill Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

144 Widener Dr, Winchester
$924,500
4 Beds ⋅ 5 Baths
Exceptional All-Brick Custom Home with Panoramic Mountain Views! Nestled on a private 2-acre cul-de-sac lot in prestigious Butler Estates, this exceptional all-brick 4-bedroom, 4.5-bath custom home offers over three finished levels, timeless craftsmanship, and breathtaking Appalachian Mountain and pastoral views. A brand-new roof adds even more peace of mind. The main level features beautiful hardwood floors and an easy flow between the gourmet kitchen and spacious family room. The kitchen offers granite countertops, center island, propane cooktop, and reverse osmosis water filtration. The family room includes custom built-ins and a fireplace. A versatile front room can serve as a library, sitting area, playroom, second office, or additional entertaining space, while a dedicated home office provides a private workspace. Upstairs, the spacious primary suite features two walk-in closets, a private balcony with stunning views, and a spa-inspired bath with double vanities, jetted tub, and tiled walk-in shower. Three additional bedrooms include a private ensuite and Jack-and-Jill bath. The finished walkout lower level is perfect for entertaining with a recreation room, gas fireplace, media room, built-ins, wet bar, and electric fireplace. An exercise room, flexible fifth-bedroom space, and full bath complete the level. Media equipment and television convey. Enjoy outdoor living on the TimberTech deck and two brick patios surrounded by professionally landscaped grounds, invisible fencing, and spectacular views. Just 10 minutes from Winchester Medical Center and minutes from Route 37 and Interstate 81, this rare all-brick Butler Estates home offers privacy, incredible views, exceptional living space, and the convenience today's buyers are looking for.

144 Widener Dr, Winchester

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

435 N Cameron St, Winchester
$900,000
This building located at 435 N. Cameron Street in Winchester, Virginia, formerly housed the Winchester Rescue Mission. Architecturally, it is a two-story, brick commercial building featuring prominent display windows across the front. The brickwork was formerly painted a crisp white, contrasted by dark framing around the windows and doors. Presently, there is a hand painted mural that covers the entire front of the building and the south side. The building with approximately 7,292 SF on two floors is sited on a lot with land area of 0.17 +/- acres with approximately 50 feet of frontage on Cameron Street. There are approximately 14 rooms. The building was constructed in 1931. The property has served as a homeless shelter since it was purchased for the nonprofit in July 1973. In recent years, the shelter has provided emergency overnight lodging for men and women, alongside hot meals, spiritual counseling, and mental health services. The facility had provided approximately 60 beds for men and women. Because the shelter consistently ran out of beds at peak capacity, the operators had to turn away individuals daily and the organization broke ground and expanded their facilities at their new facility on 2655 Valley Avenue.

435 N Cameron St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. 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:

466 Merrimans Ln, Winchester
$899,000
3 Beds ⋅ 4 Baths
Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom. The finished lower level provides outstanding flexibility with a large rec room, full kitchen, and full bath-ideas for guests, extended family, or entertaining. Outdoor living is a grand feature, with multiple brick patios and private spaces designed to take full advantage of the tranquil park setting. The property also has a unique barn for storage or a workshop. Recent improvements include a newer metal roof, while the expansive lot offers a rare sense of seclusion within the City limits. A truly unique property that combines timeless all-brick construction, modern renovations, and an unbeatable location near medical facilities, shopping, dining, downtown Winchester, and the Museum of the Shenandoah Valley.

466 Merrimans Ln, Winchester

Listing courtesy of Colony Realty. Contact:

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