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$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
Welcome to easy living at 1856 Melvor Lane! Perfectly positioned on a desirable corner lot in a welcoming 55+ community, this beautifully updated one-level home offers the ideal combination of comfort, style, and low-maintenance living. Step inside to discover an airy open floor plan enhanced by soaring cathedral ceilings and abundant natural light. Thoughtful updates—including luxury vinyl plank flooring throughout most of the home, granite countertops, a stylish tile backsplash, updated lighting, fresh interior paint, and professional cleaning—create a move-in ready space you'll appreciate from the moment you arrive. The spacious kitchen offers generous cabinet and countertop space, making meal preparation and entertaining a breeze. The primary suite features a walk-in closet and private bath, while the second bedroom provides flexible space for guests, a home office, hobby room, or den. Beyond the front door, enjoy sidewalks throughout the community that invite leisurely walks and easy access to the community center, where residents gather for activities and social events throughout the year. Lawn care and snow removal are included through the HOA, allowing you more time to enjoy the things you love and less time worrying about outdoor maintenance. Ideally located just minutes from shopping, dining, Winchester Medical Center, and historic downtown Winchester, this well-maintained home offers the perfect balance of convenience, comfort, and community.

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

$539,900
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

$339,000
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

$359,000
3 Beds 2 Baths
Price Reduced $15,000! Highly Motivated Seller! Welcome to this meticulously maintained, 3 bedroom, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Kitchen and downstairs bathroom to be painted. Property Highlights: 3 bedrooms on main level of home. Wonderful natural lighting throughout. Expansive Basement: 75% finished lower level with carpet offers endless possibilities for a rec room, gym, or home office. The remaining 25% provides excellent storage space and a dedicated workshop area. Recent Upgrades: Complete peace of mind with a new HVAC system (2019), a brand-new water heater (2025), and newer energy-efficient windows throughout. Outdoor Oasis: Relax on your covered back patio overlooking a massive backyard that borders Buffalo Lick Run. Perfect for watching local wildlife! Includes a handy storage shed. Perks & Location: No HOA fees (and city trash pickup is included!). Walk to the scenic paths at Weaver Park, and enjoy prime shopping and dining less than a mile away. Don't miss out on this city gem with a country feel—schedule your tour today!

328 Longview Ave, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com

$339,900
2 Beds 2 Baths
"Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with a large wood burning fireplace, two new windows, a new storm door, new LVP flooring, new baseboard heaters, new window A/C unit and remodeled full bathroom off of it. Both bedrooms have gorgeous, refinished hardwood floors that continue down the hall area and into a living room and dining room. Hallway bathroom has new LVP flooring, new window, new toilet and tile around the tub/shower. Large laundry room with new LVP flooring, new baseboard heater and new window. Huge deck out back with new floorboards, new top railings and new step/concrete pad down to the yard. Two great sized sheds (One with new doors). New HVAC, new thermostat and new water heater! Both Crawl Spaces have new insulation, new moisture barriers and new entrance doors. Roof was replaced in October of 2019. Chimney was inspected, cleaned and repaired as recommended so it's ready for you to enjoy! New switches, receptacles, smoke detectors, doorknobs and light fixtures throughout the home. Home has been power washed and fresh mulch put down. Agent/Owner

420 E Pall Mall St, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$760,000
5 Beds 5 Baths
Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrance—complete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty of room for everyone. Enjoy the outdoors from your beautifully landscaped yard with space to garden, entertain, or relax. A two-car garage and extended driveway provide ample parking. Conveniently located just minutes to downtown Winchester, parks, shopping, dining, and commuter routes—this home offers the space and versatility you've been searching for. Schedule your private showing today!

769 Seldon Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$525,000
4 Beds 3 Baths
Improved Price!! Welcome to this spacious and well-maintained home in the desirable Meadow Branch South community. Offering over 3,300 square feet, this 4-bedroom, 2.5-bath home provides the perfect blend of space, comfort, and thoughtful updates. The main level features an updated kitchen, ideal for both everyday living and entertaining, along with multiple living areas that offer flexibility for today’s lifestyle. Natural light fills the home, highlighted by a transom window and recently replaced front and back doors that add both style and functionality. Upstairs, you’ll find generously sized bedrooms, including a spacious primary suite featuring double walk-in closets and a private bath with a soaking tub and separate walk-in shower—a perfect retreat at the end of the day. The unfinished basement provides excellent potential for future expansion, storage, or customization to fit your needs. Major systems have been updated, including a roof just 2 years old and a heat pump less than 2 years old, and brand new hot water heater, offering peace of mind for years to come. Enjoy the outdoors in the flat backyard, complete with a large deck that was recently stained, making it ready for relaxing or entertaining in the warmer months. Overall, this home is in great condition and move-in ready, with the opportunity to add your own finishing touches. Conveniently located near shopping, dining, and commuter routes, this is one you won’t want to miss!

938 Wayne Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$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

$575,000
6 Beds 4 Baths
Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful original hardwood floors, tall ceilings, fireplace, 4 season sunroom, and a stunning staircase that adds timeless character. 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 rear unit is already leased to a reliable tenant, providing immediate cash flow. The entire home can easily be converted back to one large living space with the removal of drywall over two doorways. The new roof and gutters were installed in 2024 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

$575,000
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 rear unit is already leased to a reliable tenant, providing immediate cash flow. 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

$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: