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$379,900
2 Beds ⋅ 2 Baths
This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door. The home looks bright and beautiful from the inside and out. The bathrooms have also gotten a modern makeover, complete with touch mirrors that add a touch of luxury. This one's a must-see!

711 E Cork St, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact: 7038914520
$599,950
Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

446 N Loudoun St, Winchester

Listing courtesy of Homes By Owner, Inc.. Contact: 3013556104
$599,950
5 Beds ⋅ 2 Baths
Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking for 3-4 cars. Plus, dry basement storage available for tenant or landlord

446 N Loudoun St, Winchester

Listing courtesy of Homes By Owner, Inc.. Contact: 3013556104
$319,999
3 Beds ⋅ 1 Baths
Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort. Convenient one-level living throughout. Ideally situated just off Berryville Avenue, with quick access to shopping, dining, and major commuter routes, making it a great option for those traveling to Northern Virginia. Don’t miss this opportunity!

608 Dunlap St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$300,000
3 Beds ⋅ 3 Baths
Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

115 S Purcell Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$447,000
3 Beds ⋅ 3 Baths
Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring culinary excellence at every turn. Recessed lighting and elegant window treatments enhance the ambiance, creating a serene retreat. The exterior boasts tasteful features such as exterior lighting and a well-designed gutter system, while the expansive half-acre lot offers ample space for outdoor activities. Enjoy evenings on the spacious deck, perfect for al fresco dining or simply soaking in the tranquility of your surroundings. Additional highlights include an attached two-car garage with a front entry and convenient asphalt driveway, ensuring ease of access. Safety is paramount with smoke and carbon monoxide detectors installed throughout. This property is not just a home; it's a lifestyle of luxury and comfort, where every detail has been thoughtfully curated for your enjoyment. Embrace the opportunity to elevate your living experience in this exceptional residence.

310 Longview Ave, Winchester

Listing courtesy of Coldwell Banker Realty. Contact: 7034717220
$559,000
Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. Each Unit has 3 bedrooms and 1.5 baths. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The new roof and gutters were installed just last year and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!

1400 Valley Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$675,000
3 Beds ⋅ 3 Baths
100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025! This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic Winchester Award of Merit, this home showcases exceptional craftsmanship and dedication to preserving its character while delivering today’s comforts. Major improvements include all-new electrical, plumbing, and ductwork, along with professionally engineered structural reinforcements for long-term integrity and peace of mind. Inside, you’ll find two brand-new HVAC systems, energy-efficient windows and doors, and beautifully refinished original hardwood floors throughout. The designer kitchen features granite countertops and a custom slide-up serving window that opens to a stylish outdoor bar—perfect for entertaining. Bathrooms offer elegant tile finishes and a jetted tub for a spa-like retreat. Custom details such as barn doors, solid wood interior doors, and upgraded lighting elevate the home’s unique character. The exterior is equally impressive, featuring a custom front door, welcoming new front porch, vinyl privacy fencing, a freshly seeded backyard, and a slate patio accented with ambient string lighting. A cobblestone driveway provides two off-street parking spaces—an added luxury in this walkable downtown location. A rare opportunity to own a one-of-a-kind home that perfectly balances historic appeal, modern efficiency, and exceptional craftsmanship in one of Winchester’s most desirable neighborhoods.

112 W Germain St, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$199,900
NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about anyone building behind you. The lot sits, just outside of the historic district, making your building process significantly easier. This is a truly rare opportunity to purchase one of the last remaining lots in downtown Winchester. The Seller also has plans available to qualified buyers.

506 Fairmont Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$400,000
4 Beds ⋅ 2 Baths
Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

115 E Monmouth St, Winchester

Listing courtesy of Inmobiliaria De Las Casas LLC. Contact: 5713539363
$700,000
0.7230 Acres located at 2970 Valley Avenue featuring a former used car lot that will offer enough area to display for 30-40 cars. There is pubic water and sewer available. The used car lot does not have an office building. An office building would have to be built or a mobile office could be utilized. A new site plan will be required from the City of Winchester to operate a used car lot.

2970 Valley Ave, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$650,000
0.429 acres located at 2970 Valley Avenue. This site could be a used car lot that will offer enough area to display for 30 cars. There is a public water and sewer available. 2978 Valley Avenue presently features 5 rental units producing gross monthly revenue of approximately $4,000. The list price for purchase is $1,350000 for both properties with 1.15 acres. Both properties can be ground leased for $6,000/month.

2978 Valley Ave, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$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:

$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:

$175,000
Vacant Lot in Rolling Hills One of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer tap Fees have NOT been paid.

719 Kennedy Dr, Winchester

Listing courtesy of Colony Realty. Contact:

$499,900
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: 5407738475
$199,900

1415 Ramseur Ln, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$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 Avenue Unit #200, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$229,900
BACK ON THE MARKET — DOWNTOWN WINCHESTER INVESTMENT OPPORTUNITY Discover the potential of 109 S. Kent Street, a versatile two-story property ideally located just two blocks from the Old Town Walking Mall and one block from Winchester’s Government and Judicial Center. Situated in the B-1 Central Business District, the property offers multiple possibilities for an investor, owner-occupant, or redevelopment buyer. B-1 zoning permits residential space above a commercial use by right. Subject to City approval of a Conditional Use Permit, the property may also offer an opportunity for residential use on both floors. With approximately 1,779 square feet, full bathrooms on each level, off-street parking, and a highly walkable downtown location, the building presents an appealing value-add opportunity. Potential concepts include residential-over-commercial, a live-work arrangement, professional office space, or conversion to a multifamily residential property. Acquire a manageable downtown asset and develop a renovation plan that takes advantage of its location, flexible layout, and long-term potential. Contact John Fox with SVN Commercial Specialists for additional information, property details, or assistance evaluating the zoning and Conditional Use Permit process. All proposed uses and improvements are subject to independent verification and approval by the City of Winchester.

109 S Kent St, Winchester

Listing courtesy of Commercial Specialists. Contact:

$399,000
Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and Enterprise Zone. It qualifies for a $100K state grant along with special financing, tax rebates and other incentives to build. Buyer to verify all incentives. VERY FEW infill lots available and certainly not already site plan approved! One block from walking mall. Asking $449,000, price includes land, approved planning and zoning site plan with a building design, and floor layout by Design Concepts. Make Offer!

1 N Braddock St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$1,250,000
1.15 acres located at 2970 and 2978 Valley Avenue featuring a former used car lot that will offer enough area to display area for 30-40 cars. There is public water and sewer available. 2978 Valley Avenue features 5 rental units producing gross monthly revenue of approximately $4,000.00. The list price for purchase is $1,250,000 for both properties with 1.15 acres. The used car lot does not have an office building. An office building would have to be built or a mobile office could be utilized or use of the existing buildings could be a solution.

2970 Valley Ave, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$1,975,000
Professional Office Space For Sale. This building was the former Winchester City Schools Administrative Building. There are two floors plus a basement. There are 5,670 SF on each of two floors. Located only blocks from the Loudoun Street Walking Mall. Basement office space available. Presently the building is fully leased. There are 16 on-street parking spaces.

12 N Washington St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact: