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$375,000
3 Beds ⋅ 1 Baths
Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect for sewing, crafts, a workshop, or a home office. A unique bonus is the custom-built "catio" just off the back of the home, creating a safe outdoor retreat for your feline friends. Outside, enjoy a private backyard with mature landscaping and a detached one-car garage. Ideally located just minutes from Old Town Winchester, the Walking Mall, the Museum of the Shenandoah Valley, Winchester Medical Center, shopping, dining, and commuter routes, this home offers both convenience and charm. Major updates completed in 2016 include new windows, HVAC, roof, driveway, and beautifully refinished hardwood floors. The home is served by public water and a private septic system.

805 Pennsylvania Ave, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
$400,000
2 Beds ⋅ 2 Baths
Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets, stainless steel appliances, and a built-in microwave. The primary bedroom has a walk-in closet and a private bathroom with a walk-in shower. You’ll also find main-level laundry, an attached one-car garage, a covered front porch, and a rear patio where you can relax outdoors. The HOA takes care of lawn maintenance and snow removal and provides access to the community clubhouse, gathering spaces, and sidewalks. Located close to Winchester Medical Center, shopping, restaurants, and historic downtown Winchester, this home offers comfort and convenience in a welcoming community.

1853 Rosser Ln, Winchester

Listing courtesy of Realty FC. Contact: (540) 931-0144
$375,000
3 Beds ⋅ 2 Baths
Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$435,000
3 Beds ⋅ 2 Baths
Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice rack & a tile backsplash. The primary suite includes a remodeled primary bath (2023). There is a cozy sun porch on the rear of the home. Enjoy your morning coffee on the inviting front porch or out on the rear deck. The partially finished basement offers a large recreation room with wood stove for all your favorite hobbies. There is also a spacious storage room for your holiday decor, etc. The fenced backyard has a fire pit perfect for cooler fall evenings. There is also a shed for storing your gardening tools.

338 Lanny Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$420,000
2 Beds ⋅ 2 Baths
Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level living just minutes from Historic Old Town Winchester. This beautifully maintained 2-bedroom, 2-bath ranch home showcases exceptional pride of ownership with beautiful hardwood flooring, soaring vaulted ceilings, and an open floor plan filled with natural light. The kitchen features a decorative ceramic tile backsplash, an updated Moen faucet, a new refrigerator, and a new microwave, combining style and functionality for the home chef. The spacious primary suite offers a relaxing retreat with a private en-suite bath and generous closet space. A second bedroom and full bathroom provide comfortable accommodations for family and guests. The inviting sunroom is bathed in natural light, creating the perfect space for morning coffee, reading, hobbies, or a home office. Additional updates include new gas fireplace logs, adding warmth and charm to the living area. Outside, you'll enjoy a beautifully landscaped garden that creates a peaceful setting for relaxing or entertaining. French drains have also been installed to enhance drainage and provide added peace of mind. Residents of Willow Lawn Cottages enjoy a friendly community atmosphere with convenient access to Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, Jim Barnett Park, the Museum of the Shenandoah Valley, and the Winchester Green Circle Trail. Shopping, dining, healthcare, and year-round events are just minutes away.

1826 Kershaw Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$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:

$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:

$545,000
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
$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
$370,000
2 Beds ⋅ 2 Baths
Beautifully maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ Community. The main-level features an open floor plan, vaulted ceiling, ceiling fan, gas fireplace, large concrete patio, and 1-car garage. 2026 updates include a new HVAC system. The primary suite offers a walk-in closet, private full bath, and laundry. Low maintenance living includes lawn and landscape care, snow and trash removal, allowing more time to enjoy the community’s clubhouse, exercise room, and scenic paths. Conveniently located near shopping, dining, and healthcare– Winchester Medical Center and close to local attractions like the galleries at the Museum of the Shenandoah Valley.

1845 Rosser Ln, Winchester

Listing courtesy of The Greene Realty Group. Contact: 8882785840
$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
$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
$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
$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
$328,500
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: