Refine Search
Map
Sort by
$1,724,000
Beautifully restored and fully modernized mixed-use building in the heart of historic Winchester. This exceptional offering includes a fully leased commercial building with three strong-credit tenants, a valuable adjacent parking lot approved for future mixed-use development, and a third floor ready for residential conversion. Located just one block from the historic Old Town Winchester Walking Mall, this legacy investment property offers more than 9,300 square feet of space with the first and second floors completely renovated and occupied. The third floor presents an outstanding value-add opportunity for apartment development, with potential eligibility for Historic Tax Credits. The property is also located within an Enterprise Zone, providing access to additional grant and incentive programs. The sale includes the adjacent parking lot (Tax ID 173-01-E-1), which is approved for multifamily development or can continue to serve as a highly desirable dedicated parking facility for tenants and customers. Current net operating income exceeds $80,000 annually, providing immediate cash flow with significant upside potential. Recent capital improvements include a metal roof, new HVAC systems, and modern tenant build-outs throughout the building. This unique asset offers a diversified income stream with retail and office tenants in place, while creating future opportunities for residential development on both the third floor and the adjacent parking lot. Ideal for a 1031 exchange buyer or investor seeking stable income, long-term appreciation, and redevelopment potential in one of the Shenandoah Valley's most desirable downtown locations. Conveniently located one block from the Braddock Street Parking Garage. Rarely does an opportunity of this caliber become available in Downtown Winchester. Contact the listing agent to schedule a private showing.

48 W Boscawen, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$1,350,000
Prime Medical Condo suite for Sale; located adjacent to the Winchester Medical Center. 6,200 Square Feet total with 4,580 square feet immediately available. 1,620 square feet is being leased, with another year on the lease. Building is in excellent condition, fully updated and easy to maintain. Prominent and highly visible location and ample parking. Few landlord responsibilities. Huge growth market! Priced at $1,350,000. Also available for lease.

142 Linden Dr Unit #106, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$487,900
Circa 1920 office building in downtown Winchester. Currently used as a lawyer's office, but could easily be an office-and-residential space or a single-family home. Off-street parking.

124 S Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

$339,000
Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath. The properties are deeded separately as two parcels (tax #193-01-T-9 & 193-01-T-8) , providing added flexibility for future investment strategies. All occupied units are currently rented on month-to-month leases, offering the new owner maximum flexibility to adjust rents, renovate, or continue operating as investment properties. As of the listing date, one unit is vacant, presenting an immediate opportunity to place a new tenant at market rent or occupy the property. Prospective buyers are welcome to drive by and walk the exterior of the properties. Interior showings are by appointment only. Whether you're looking to expand your rental portfolio or invest in a property with immediate income potential and future upside, this is a rare opportunity within Winchester City limits.

211, 213-215 E Clifford St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$182,000
2 Beds ⋅ 2 Baths
Newly remodeled 2-level townhouse located in a quiet, established neighborhood! This move-in ready home features a bright, sun-filled kitchen with a spacious eat-in dining area, two generously sized bedrooms, and 1.5 bathrooms. Enjoy the convenience of one assigned parking space directly in front of the home, plus a guest parking pass for unmarked spaces. Relax on the private rear deck or take a short, less than 5-minute walk to Frederick Douglass Park. Additional conveniences include central A/C and an in-unit washer and dryer. Recent updates include: New dishwasher New stove New microwave New kitchen faucet New toilets in both bathrooms New bathroom faucets New upstairs carpet New quartz kitchen countertops Major systems have also been updated: Updated refridgerator with added water line Washer and dryer are less than 3 years old HVAC system and water heater are less than 5 years old Whether you're looking for your next home or an excellent investment opportunity, this property offers great value and rental potential. Property is being sold As-Is. Home inspection is for informational purposes only. *Conventional Loan and Cash only. FHA does not qualify for this property*

313 Avon Ct, Winchester

Listing courtesy of AMN Realty, LLC.. Contact:

$330,000
3 Beds ⋅ 3 Baths
Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level living with additional space in the lower level. The bright and spacious living room serves as the centerpiece of the home, featuring a large bay window that fills the space with natural light. On the main level there are three bedrooms, a full bath, and a convenient half bath. The lower level offers interior access and includes a finished room and full bathroom, providing flexible space for a home office, recreation room, hobby area, or additional living space, while the unfinished portion offers excellent storage potential. Outside, enjoy a fully fenced backyard and a covered carport for one vehicle on a spacious lot. Recent updates include a freshly painted interior completed in June 2026 and the addition of a full bathroom in the lower level in 2022/2023 Ideally located with easy access to I-81, this property is approximately 10 minutes from Shenandoah University and just minutes from shopping, dining, and other everyday conveniences. Successfully maintained as a rental property for the past four years, this home presents an excellent opportunity for both owners and investors seeking a well-cared-for property in a convenient location.

101 Locust Ave, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$299,000
4 Beds ⋅ 3 Baths
Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many visions, this property is the ideal project for someone ready to create something extraordinary. The home was once configured with an upper‑level apartment, complete with a private entrance, back stairway, and space for a second kitchen and bath—perfect for multi‑generational living, rental income, or reimagining the entire second floor into a spacious primary suite. Updated vinyl, energy‑efficient windows and a durable metal roof provide a strong start for renovation. A walk‑up attic offers excellent storage and the potential to be finished for additional living space. The upper level could accommodate three full bathrooms, allowing for a highly functional and modern second floor once renovated. An unfinished basement with both interior access and a walk‑up exit is even more space for storage. New electrical and plumbing updates are needed giving the next owner the opportunity to modernize the home exactly to their taste. With its architectural pedigree, adaptable layout, and solid structural foundation, this property is a rare chance to bring a historic home back to life and create something truly special.

719 National Ave, Winchester

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

$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:

$320,000
4 Beds ⋅ 2 Baths
Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout. Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private second-floor balcony and a shared first-level patio, perfect for relaxing or gathering with friends and family. Whether you're searching for a primary residence, an owner-occupied investment, or a property with income potential, this home offers exceptional flexibility in a highly desirable location. Ideally situated in the heart of Winchester, you'll be just minutes from the popular Old Town Winchester Walking Mall, with convenient access to shopping, dining, entertainment, and local attractions. Don't miss this opportunity to own a distinctive property in one of Winchester's most sought-after locations

410 S Cameron St, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$499,900
4 Beds ⋅ 3 Baths
Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining. Step inside to find warm hardwood flooring, abundant natural light, and thoughtfully renovated spaces throughout. The updated kitchen serves as the centerpiece of the home, featuring a large island, pantry, recessed lighting, and a seamless connection to the dining area. Two charming brick fireplaces add character and create inviting spaces to gather with family and friends. The finished lower level provides even more room to spread out, complete with a spacious recreation area, built-in bar, full bathroom, garage access, and a separate exterior entrance. Whether you’re hosting game day, creating a home office, or setting up a guest retreat, this versatile space offers endless possibilities. Outside, enjoy a spacious backyard ideal for entertaining, gardening, or simply relaxing in your own private outdoor oasis. The welcoming front porch and mature neighborhood setting enhance the home’s curb appeal and charm. Ideally located near schools, parks, shopping, dining, and commuter routes, this move-in ready home offers modern updates, generous living space, and a prime location. Don’t miss the opportunity to make this Cedarmeade gem your next home.

110 Russellcroft Rd, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com
$329,900
3 Beds ⋅ 2 Baths
Charming, beautifully maintained all-brick ranch home at 936 Allen Drive! Built in 1965 by Kingsberry Homes using the sought-after Belden model, this special property has been lovingly cared for by one family since its construction and even includes the original architectural floor plans. Inside, the move-in-ready home offers stunning hardwood floors and an enclosed carport seamlessly converted into a spacious family room. The main-level layout features 3 bedrooms and 1.5 baths, including a fully renovated hallway bath with a modern walk-in shower. A full, unfinished basement provides massive storage potential, while the covered rear deck and patio overlook a beautifully landscaped backyard oasis. The sellers have recently invested in numerous proactive improvements, including completed foundation work, radon mitigation, electrical panel optimization, and recent HVAC service (supporting documentation available). Excellent location just minutes from historic downtown Winchester shops and dining, with effortless commuter access to Interstate 81 and Route 50 into Northern Virginia. A wonderful opportunity with important updates already addressed!

936 Allen Dr, Winchester

Listing courtesy of Dream Real Estate. Contact: 5408692964
$348,000
3 Beds ⋅ 2 Baths
Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on a desirable corner lot, the home features ample driveway parking and presents a variety of opportunities to suit your needs.

302 Wentworth Dr, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$295,000
3 Beds ⋅ 1 Baths
Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a well-maintained appearance. Whether you're looking to expand your investment portfolio or secure a future owner-occupied residence, this property presents a great opportunity. A tenant is currently in place through November 8, 2026, paying below market value, with potential for future rent increases. Enjoy immediate rental income and long-term upside in a sought-after location.

405 Shenandoah Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$359,900
3 Beds ⋅ 2 Baths
Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a seamless connection to the formal dining area—perfect for hosting friends and family. The kitchen is a standout feature, boasting granite countertops, stainless steel appliances, white cabinetry, and designer-inspired finishes that make both cooking and entertaining a pleasure. Each bedroom is generously sized with ample closet space, while the thoughtful layout provides comfort and functionality throughout. Outside, a private cement parking pad adds everyday convenience. Packed with charm, natural light, and updates you'll love, Gray Avenue is the perfect place to call home.

601 Gray Ave, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$554,900
2 Beds ⋅ 3 Baths
Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury. Unit 105 features an open-concept floor plan with soaring ceilings, rich architectural details, and abundant natural light. The gourmet kitchen is equipped with stainless steel appliances, gas cooking, granite countertops, and a spacious island perfect for entertaining. A cozy library with fireplace, elegant living spaces, and a convenient main-level powder room add to the home's charm and functionality. Upstairs, the spacious primary suite offers a spa-inspired custom shower, and double vanity. A generous second bedroom and full bath with soaking tub provide comfort for guests or family. Additional highlights include a covered porch, dedicated parking space, detached private garage, and beautifully maintained common grounds. Originally the site of Fort Loudoun and later a historic girls' school dating to the 1830s, The Fort offers a truly unique living experience steeped in local history. Enjoy walkable access to Winchester's finest restaurants, shops, breweries, museums, and local attractions while residing in one of the city's most iconic addresses.

411 N Loudoun St Unit #105, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$425,000
3 Beds ⋅ 3 Baths
***4.25% INTEREST RATE AVAILABLE*** Located in the heart of Winchester’s Historic District, this remarkable property offers a rare opportunity to own a piece of the city’s rich architectural heritage just moments from vibrant Old Town Winchester. Blending timeless character with flexible living options, the home showcases classic historic charm paired with thoughtful updates that support today’s lifestyle. Inside the main residence, you’ll find warm hardwood flooring, detailed millwork, built-in features, and inviting fireplaces that highlight the home’s original craftsmanship. Spacious living and dining areas provide an ideal setting for both everyday living and entertaining. The layout offers functional flow, with well-proportioned rooms and abundant natural light throughout. Upstairs, generously sized bedrooms provide comfortable retreats, including a primary suite with its own private bath. Additional bedrooms and a second full bath ensure convenience and flexibility for guests or family. On the main level, a versatile bonus space offers options for a home office, reading nook, or mudroom, along with practical features such as laundry and a powder room. Adding to the property’s appeal is a separate secondary structure with its own address, offering valuable additional finished space ideal for guests, studio use, or potential income-producing opportunities. Behind it, multiple outbuildings provide exceptional storage, workshop potential, or future redevelopment possibilities. Outdoor amenities include off-street parking and a generous rear yard setting that enhances both privacy and usability. The property’s zoning allows for a variety of residential and potential mixed-use opportunities, offering flexibility rarely found in a historic setting. With its unbeatable location, architectural charm, and multi-structure versatility, this unique offering presents endless possibilities for homeowners, investors, or those seeking a distinctive property in one of Winchester’s most desirable historic neighborhoods. THIS HOME IS ALSO AVAILABLE FOR RENT!

703 S Loudoun St, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$3,250,000
Here is the opportunity to own a piece of history! The hottest spot in Winchester/Frederick County. The 20,386+/- SF building started out as a furniture warehouse that served the area for many years. In 2005 it was converted to a Restaurant that is now the most popular dining and entertainment destination in the area. In addition to the famous “pub” area, the restaurant includes a more formal dining area with a piano bar, tons of outdoor seating, Banquet and events area on upper level, outdoor covered desk/bar and the most popular feature, “The Jam Rock Boat.” That’s right, an actual boat was hauled in and permanently installed to provide an area for bands to use as a stage. This is a major draw on Friday and Saturday nights when the best local bands entertain the crowds. Just steps from the Old Town Walking Mall and adjacent to the historic Wyndham/George Washington Hotel. Well-established turn-key business that includes all fixtures, equipment, and real estate. Owner wants to retire but will assist with transition after purchase. Seasoned, well-trained managers and staff will stay. Winchester is seeing incredible growth. This is an opportunity to ride the expansion which will be seen in the coming years. CPA prepared financials available to qualified buyers. Non-disclosure Agreement required. Owner financing available with acceptable down payment.

125 E Piccadilly St, Winchester

Listing courtesy of Oakcrest Commercial Real Estate. Contact:

$1,150,000
5 Beds ⋅ 5 Baths
This home has a 2.25% VA Assumable Loan. There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important work has already been done. Over the past several years, the owners have invested extensively in both beauty and peace of mind, creating a home that is as practical as it is impressive. Imagine gathering friends and loved ones around the oversized island in the beautifully renovated kitchen. Quartz countertops, quality cabinetry, stainless steel appliances with gas cooking, and abundant workspace make this the kind of kitchen where holiday meals, birthday celebrations, and ordinary Tuesday dinners become lasting memories. Rich hardwood floors and updated finishes add warmth and sophistication throughout the main level, while formal and casual living spaces flow effortlessly together. Need a quiet place to work, create, or manage life's daily demands? A private office on the main level offers the flexibility today's lifestyles require. The private office is a space you'll actually look forward to spending time in, surrounded by windows that fill the room with natural light and create an inspiring setting for working from home or simply enjoying a quiet moment with a cup of coffee. Just beyond, the dramatic two-story family room serves as the heart of the home, with soaring ceilings and an open, airy feel that makes every gathering feel a little more special. Whether you're hosting a holiday celebration, cheering on your favorite team, or enjoying a cozy evening by the fire, this impressive space brings everyone together while still feeling warm and inviting. At day's end, retreat to what may become your favorite room in the house. The completely renovated primary bath is nothing short of breathtaking. With its freestanding soaking tub, frameless glass shower, elegant finishes, and designer-inspired style, it feels less like a bathroom and more like a luxury spa featured in the pages of an upscale magazine. Beyond the beauty, the major systems have been thoughtfully updated as well. The roof has been replaced and enhanced with new insulation and a solar fan. The furnace heat exchanger and blower assembly have been replaced and serviced, while the AC fan and motor have also been updated, giving future owners confidence and comfort for years to come. Most updates occurred in 2023. And then there's the walkout lower level. With 9-foot ceilings, newer luxury vinyl plank flooring, a guest room, additional office space, and an expansive recreation area, this level is ready for whatever your imagination can create. Golf simulator? Home theater? Craft studio? Fitness room? The possibilities are endless. Bright, open, and inviting, it extends directly to the concrete patio, with a portion tucked beneath the screened porch for cool shade on warm Virginia afternoons. Outside, you'll discover the kind of backyard that invites you to linger a little longer. Enjoy morning coffee or evening conversations on the screened porch with low-maintenance composite decking. The beautiful white vinyl fence creates a sense of privacy and charm, while mature landscaping provides a peaceful, park like setting just minutes from downtown Winchester, local parks, restaurants, shopping, and Winchester Medical Center. Completing the package is a spacious three-car garage and a rare financing opportunity that may be the ultimate bonus. Eligible VA buyers may have the opportunity to assume the seller's existing VA loan at an attractive 2.25% interest rate. Homes with this combination of location, updates, character, and opportunity do not come along often. The next chapter is ready to be written. All that's missing is you.

801 Armistead St, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$385,000
3 Beds ⋅ 1 Baths
Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow for indoor-outdoor living and entertaining. Three generously sized bedrooms provide ample closet space, while the unfinished basement offers abundant storage and endless potential for future expansion, a home gym, workshop, or recreation space. Step outside to enjoy the privacy of the fully fenced backyard—ideal for relaxing evenings, pets, gardening, or entertaining guests. Great investment opportunity, tenant in place until 7/14/2026.

540 Bellview Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$262,000
3 Beds ⋅ 2 Baths
Attention investors…24 month lease in place and new HVAC! Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or den. Upstairs you will find three bedrooms, full bathroom and laundry. Permitted on street parking.

321 N Kent St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$459,999
5 Beds ⋅ 3 Baths
Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious bedrooms and 3 full bathrooms, there’s room for everyone. Situated on a quarter-acre lot with no HOA, you'll enjoy privacy and freedom. The large deck and screened-in porch are perfect for outdoor dining, entertaining, or simply unwinding. Conveniently located close to shopping centers and restaurants — everything you need is just minutes away!

419 Summit Ave, Winchester

Listing courtesy of Lifestyle Realty, LLC.. Contact: 7034003356
$399,000
2 Beds ⋅ 2 Baths
PRICE REDUCED! BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing or just starting out, or even as an investment property. And there's no HOA! Replacement windows. Two wood-burning fireplaces. Large living room with a picture window. Formal dining room with a built-in cabinet. Primary bedroom with own bath has a walk-in shower. Central air and a whole house fan. The basement offers a large family room with a pool table, an office/den with built-ins, and a utility room. New vinyl plank flooring in kitchen. Tile floors in the bathrooms. New sinks and toilets. New tub/shower. Updated electric (1994). Public water. Has a 3-bedroom septic, according to health department records. Real estate and personal property sold as-is.

437 Beechcroft Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$899,000
Exceptional 2-acre level commercial parcel in a highly desirable area of Winchester offering strong visibility along a primary corridor into downtown. Ideally located just two blocks from Winchester Medical Center, this property sits in one of the most established and high-demand professional corridors in the city. The site features excellent road frontage and level topography, providing a versatile footprint suitable for a wide range of professional and service-based uses. Zoned RO-1 (Residential Office District), the property allows for a variety of low-intensity and compatible uses, including: Medical and dental offices Professional offices (legal, financial, administrative) Outpatient and clinical services Personal service establishments Limited residential use in conjunction with office use Other permitted low-impact uses under RO-1 zoning Additional uses permissible with conditional use permit, see city's RO1 zoning. RO-1 zoning is designed to support a professional office environment that integrates well with surrounding residential and institutional uses, making this an excellent fit for medical and professional users seeking proximity to the hospital corridor. With its close proximity to Winchester Medical Center, strong visibility, and flexible zoning, this parcel offers a rare combination of location and usability in one of Winchester’s most established commercial areas.

1625 Amherst St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$359,900
2 Beds ⋅ 2 Baths
Low-maintenance, one-level living in Winchester! Located on a corner lot in an established 55+ community, 1856 Melvor Lane offers 2 bedrooms, 2 full baths, an open floor plan, and thoughtful updates throughout. Cathedral ceilings and natural light give the main living area an open, airy feel, while luxury vinyl plank flooring extends through most of the home. Fresh interior paint and updated lighting create a clean, move-in-ready interior. The kitchen features granite countertops and a tile backsplash and flows easily into the dining and living areas—an efficient layout that makes everyday living simple and comfortable. The primary bedroom offers a walk-in closet and private full bath. The second bedroom and additional full bath add flexibility for guests, a home office, hobby space, or den. Outside, enjoy the extra breathing room of a corner lot without the upkeep of a large property. HOA-provided lawn care and snow removal help simplify exterior maintenance, and the community offers sidewalks, a neighborhood community center, and an active calendar of events available through the HOA. The location adds even more convenience, with shopping, restaurants, everyday services, Winchester Medical Center, and historic downtown Winchester all nearby. If you have been looking for an updated home with one-level living, manageable space, low-maintenance exterior living, and a convenient Winchester location, 1856 Melvor Lane is worth a closer look.

1856 Melvor Ln, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475
$269,000
*** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plan designed by Seller customized for this lot and optimized for cost effective construction. Closing on the lot may occur upon issuance of the Building Permit in Buyer’s name by the City of Winchester. ***This modern farmhouse style home includes 5,630 square feet of living space with 4+ bedrooms and 4 ½ bathrooms. Your cost could much less than what custom builders charge and provide you with home equity as you save on design and engineering fees, general contractor upcharges and overhead, and site expenses. This plan is not builder’s standard grade; it offers you high quality and upscale features that you’ll love! This may be the perfect opportunity for you to acquire a prime lot in the City of Winchester, Virginia, and build your dream home! Nestled in the established Meadows Branch neighborhood, one of Winchester’s most upscale developments of beautifully crafted homes, this spacious 0.97-acre lot backs to the protected Abrams Creek Wetlands Preserve and Winchester’s Green Circle Trail. Utilities are readily available, including natural gas and high-speed internet. Water and sewer provided by the City of Winchester are already stubbed to the property line, and the water and sewer tap fees have already been paid, for which Buyer would pay to Seller $20,800 for a 1” water supply line in addition to the purchase price. The lot is already prepped with clearing, fill, and avoidance of expensive excavation of limestone prevalent in Winchester. Located in an ideal setting for both peaceful relaxation in nature and an active lifestyle in the community, this lot is near the biking, running, and walking Green Circle Trail through the City of Winchester and the Abrams Creek Preserve pathway. This lot is in close proximity to Winchester’s Historic Old Town (1.9 miles), Shenandoah University (2.2 miles), Winchester Medical Center (1.6 miles), Museum of the Shenandoah Valley (1.7 miles), and numerous dining, shopping, work, and leisure options. Winchester is an ideal historic town that has a complete package of charm, friendliness, parks, museums, schools, and businesses. It perfectly blends the nostalgic lifestyles of the past with the modern conveniences of the present. As a growing community, and especially in this neighborhood, the rising real estate values make this property a great investment. Do not miss your chance to own this rare opportunity! This is your opportunity to create something truly special!

823 Armistead St, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$524,900
5 Beds ⋅ 4 Baths
Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family room, complemented by hardwood floors throughout the main living areas. The kitchen is equipped with stainless steel appliances, double ovens, and a center island—perfect for cooking and entertaining. Formal living and dining rooms offer plenty of space for gatherings, while large windows provide abundant natural light throughout the home. The walk-up basement includes a full bath, rec room, and a versatile 5th bedroom that can also serve as an office or playroom (no egress window). Outside, enjoy a stamped concrete patio and fully fenced rear yard. Located in a sidewalk-lined neighborhood with streetlights and a nearby playground, this home is just 5 minutes from downtown. A wonderful place to call home!

660 Beehive Way, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$399,900
2 Beds ⋅ 2 Baths
Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and thoughtfully curated modern finishes throughout. A welcoming front porch adds to the home's character and curb appeal, while inside, the gourmet kitchen features upgraded cabinetry, premium quartz countertops, stainless steel appliances, and sleek designer touches. The home also features an energy-efficient hybrid heat pump water heater, which uses approximately one-third the electricity of a traditional electric water heater, helping reduce utility costs while providing reliable hot water. Spa-like baths offer stunning tile work, custom cabinetry, and stylish lighting. One of the standout features of this home is the charming private rear patio—an ideal outdoor extension of the living space, perfect for entertaining, dining al fresco, or simply relaxing. The property also includes a dedicated assigned parking space that is pre-wired and EV charger ready, offering added convenience for modern living. A spacious unfinished dry basement provides exceptional storage space, an uncommon and highly desirable feature for downtown living, offering plenty of room for seasonal décor, bicycles, outdoor gear, and more. The monthly condo fee also includes exterior maintenance of common areas, snow removal, water & sewer service, adding value and helping simplify your monthly household expenses. Whether you are seeking a sophisticated primary residence, a lock-and-leave weekend retreat, or an investment opportunity, this move-in ready condo offers an exceptional combination of location, character, energy efficiency, storage, and modern upgrades that are difficult to duplicate. This is a wonderful opportunity to purchase pieces that complement the home's style and make moving in even easier. Please inquire for a list of available items and pricing. Schedule your private showing today and experience downtown Winchester living at its fines 🏡✨ Love the furnishings? Buy it furnished for $415000!

118 1/2 E Cork St, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$3,250,000
Rare opportunity to own a 22,320 sq. ft. indoor sports and entertainment facility situated on 3 acres with Industrial zoning. Formerly a youth development center, the building features two gymnasiums, a theater area, multiple kitchens with dining spaces, and several large restroom areas. The flexible layout supports single-tenant or multi-tenant use, making it ideal for recreational, institutional, or commercial operations. The property also offers extensive on-site parking and excellent potential for adaptive reuse. Unique large-scale facility with a wide range of possible uses.

3 Battaile Dr, Winchester

Listing courtesy of Commercial Specialists. Contact:

$329,000
3 Beds ⋅ 2 Baths
Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll find a practical and inviting layout featuring 3 bedrooms, 1.5 bathrooms, a spacious kitchen, separate living and dining areas, main-level laundry, and additional storage space. Recent updates add extra peace of mind, including an HVAC system installed in 2020 and a roof recoated in 2021. Outside, the home offers valuable city-living features, including off-street parking and usable outdoor space for relaxing, gardening, pets, or entertaining. The surrounding streetscape is also seeing meaningful improvements, with the street being repaved, sidewalks redone, and new trees expected to be planted along the street. Whether you are searching for a primary residence, a Winchester-area home base, or a potential investment property, this home offers a strong combination of location, utility, and opportunity in an established Winchester neighborhood with quick access to major roadways and the surrounding Shenandoah Valley. Seller offering up to $2,500 towards painting with acceptable offer.

307 E Piccadilly St, Winchester

Listing courtesy of HoneyWay. Contact: 5402149682
$1,179,000
4 Beds ⋅ 5 Baths
Stepping onto the Southern style covered front porc.h you enter the large foyer with a Schoenbek chandelier. There is a living room to the left which opens to a separate dining room with a hand painted blue and gold ceiling. The kitchen is eating size with granite counter and large island. Double doors lead to a small back porch and stairs to the patio. The first floor family room has a gas fireplace, built-in cabinets, a built-in window seat and two-story windows. The garden room has tile floor, built-in bookcases and windows on two sides overlook the rose garden and back yard. There is a powder room off the family room. The second floor has four bedrooms and three full baths. The master bedroom is very large with a three-sided fireplace and sitting area with tray ceilings. There is a large walk-in closet with custom built ins. The master bath has two separate vanities with vessel sinks. The generous shower is glass sided and there is a large spa tub with a Schoenbek chandlier. The bath has a tile floor and artistic tiles around the shower, spa tub and vanities. Two bedrooms share a jack and jill bath with each haviing it's own vanity.. All the bathrooms have marble counters. There is a library on this floor with built in bookcases which could be turned into a fifth bedroom. The upper hall has an overlook to the family room below. You enter the lower level from the kitchen and there is an exit from the recreation room onto the patio at the rear. There is a gas fireplace in the large family room with a wet bar and a generous adjoining area for activities. There is a gym with a wall of mirrors, an office, a large cedar closet, half bath and storage room. The entire house has crown molding, many shadow boxes, and 5" baseboards. All the walks, the driveway and the patio are done in architectual concrete. The rear yard has a waterfall, brick walls and extensive plantings. On the side of the home there is a large rose garden. The house has a security system; and also, the entire home is wired with speakers for music. The roof is less than 5 years old. The oven and microwave were new in 2025. Details about each room is found in documents. This home is within 5 minutes of Medical Center, Museum of the Shenandoah Valley and the Green Trail and within 10 minutes of Old Town Walking Mall, Shenandoah University and shopping, Note: one owner is licensed broker/real estate agent & other owner is licensed real estate agent

1004 Heth Pl, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484