207

Winchester, VA Homes for Sale under $500,000

Section Image Section Image
  • /54

    $409,000

    $21K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,376 Sq Ft

    115 Brockham Ct, Winchester, VA 22602

    Beautifully upgraded, like-new 3-bedroom, 2 full and 2 half bath townhouse with a 2-car garage offers 2,376 total finished square feet, a spacious floor plan, and abundant natural light throughout. Hardwood floors throughout main level. Living room features gas fireplace with ornate mantel, granite surround, and hearth. Spacious kitchen with granite countertops, large island with seating, and

    Punam Malik Samson Properties

    115 Brockham Ct, Winchester, VA 22602
  • /78

    $369,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    506 Grouse Dr, Winchester, VA 22602

    This property is nestled in a charming community, this stunning new construction home offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects the kitchen and

    Steve DuBrueler Coldwell Banker Premier

    506 Grouse Dr, Winchester, VA 22602
  • /27

    $484,900

    $14K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,511 Sq Ft

    106 Etnam St, Winchester, VA 22602

    Beautiful updated 3400 sqft home, ready for immediate move-in! Featuring a host of updates including a new roof, flooring,counters and more, this lovingly kept home has all the updates and space you need. The main floor has a wide open floor plan with bright living/kitchen areas, opening to a spacious deck, and the upstairs has 4 bedrooms and a large primary suite with walk-in closet. Downstairs

    Jacob Taylor Blue Valley Real Estate

    106 Etnam St, Winchester, VA 22602
  • /25

    $459,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,025 Sq Ft

    654 Treys Dr, Winchester, VA 22601

    Welcome to 654 Treys Drive - Great corner lot in Williamsburg Heights! No HOA! One story home built in 1986 on crawl space with 3 bedrooms and 2 baths. Gas heat, and electric air conditioning. Beautiful wood floors. Great room with cathedral ceiling. Glassed in sunroom for cozy evenings. Spacious 2-car garage perfect for additional storage. Sorry no home sale contingencies. Home inspection for

    Don Butler Virginia Property Group, Inc.

    654 Treys Dr, Winchester, VA 22601
  • /60

    $489,990

    New Construction $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,971 Sq Ft

    251 Rossmann Blvd, Winchester, VA 22602

    The home is vacant, move-in ready, with preselected upgrades and a one-year home warranty. Welcome tothis beautifully crafted new home by a respected local builder, offering almost 2,000 square feet ofthoughtfully designed living space in the desirable Sovereign Village community, with room to grow in theunfinished basement. The inviting, open-concept main level features a spacious

    Marisa Varley ERA Oakcrest Realty, Inc.

    251 Rossmann Blvd, Winchester, VA 22602
  • /39

    $314,900

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    105 Apache Trail, Winchester, VA 22602

    Welcome to 105 Apache Trail, a beautifully updated cabin in Shawneeland offering privacy, character, and flexibility for full time living, a weekend escape, or income potential. Set on a level wooded lot, this home features a floor to ceiling stone fireplace with wood burning stove, exposed beams, and warm, inviting finishes. The main level includes two bedrooms, a full bath with in-unit laundry,

    Kerem Demirci Coldwell Banker Realty

    105 Apache Trail, Winchester, VA 22602
  • /20

    $449,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,657+ Sq Ft

    CABRAL Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

    The Cabral, a 1,657 square foot two-story home, offers an open-concept design perfect for modern living. Featuring three bedrooms, two and a half bathrooms, a versatile loft, and a two-car garage, this home is ideal for families seeking both space and functionality. Upon entering through the front porch, you'll find a convenient first-floor powder room and coat closet in the foyer. The spacious

    D.R. Horton Builder
    137 Seminole Dr Unit 36203778, Winchester, VA 22602
  • /18

    $389,900

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,147 Sq Ft

    127 Inca Trail, Winchester, VA 22602

    Brand new split foyer home located in Shawnee Land subdivision, situated on a beautiful 0.34-acre wooded lot with mature trees. This home offers both privacy and accessibility. The thoughtfully designed floor plan features 3 bedrooms and 3 full bathrooms, including a spacious primary bedroom with a private bath and walk-in closet. Enjoy a bright kitchen with an island bar, stainless steel

    Faye Campbell Beltway Realty, LLC.

    127 Inca Trail, Winchester, VA 22602
  • /45

    $260,000

    • 2 Beds
    • 1 Bath
    • 997 Sq Ft

    108 Martin Dr, Winchester, VA 22602

    Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large windows that let in plenty

    Heloisa Amar Samson Properties

    108 Martin Dr, Winchester, VA 22602
  • /64

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 2,180 Sq Ft

    706 S Cameron St, Winchester, VA 22601

    Claim your spot in the heart of the city with this authentic 1866 gem, perfectly positioned to enjoy everything downtown Winchester has to offer. Proudly displaying its Winchester Historic Building plaque, this home is just steps from the vibrant local dining scene, boutique shopping, parks, and schools. It’s a rare find that pairs 19th-century soul with modern reliability, featuring the coveted

    Dan Whitacre Colony Realty

    706 S Cameron St, Winchester, VA 22601
  • /28

    $485,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,953 Sq Ft

    PINE Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

    The Pine is a 1,953 square foot open concept home, offering four bedrooms, two and a half bathrooms and a two-car garage. A foyer with a powder room and coat closet greets you as you enter this home. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for

    D.R. Horton Builder
    137 Seminole Dr Unit 36203779, Winchester, VA 22602
  • /35

    $399,900

    New Construction $10K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    211 Inca Trail, Winchester, VA 22602

    Nearing completion! Premium Finishes: Enjoy a builder-upgraded interior featuring gleaming hardwood floors throughout the entire home (including all bedrooms) and elegant tile in all bathrooms.Gourmet Kitchen: Equipped with upgraded cabinetry, sleek granite countertops, a central island, and a sunny breakfast nook.Modern Layout: An airy, open floor plan connects the family room to a

    Jim Thomson Realty ONE Group Old Towne

    211 Inca Trail, Winchester, VA 22602
  • /17

    $449,990

    New Construction $3K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,657 Sq Ft

    136 Wappinger Terrace, Winchester, VA 22602

    Step into 1,657 square feet of well-designed living space in the Cabral, featuring 3 spacious bedrooms, 2.5 bathrooms, and a flexible loft upstairs—perfect for a home office, playroom, or additional lounge area. This home showcases a charming white siding exterior with stone accents, while the interior boasts sleek white kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

    D.R. Horton Builder
    136 Wappinger Terrace, Winchester, VA 22602
  • /6

    $370,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    1845 Rosser Ln, Winchester, VA 22601

    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, largeconcrete patio, and 1-car garage. 2026 updates include a new HVAC system. The primary suite offers awalk-in closet, private full bath, and laundry. Low maintenance living includes lawn and

    Derek Greene The Greene Realty Group

    1845 Rosser Ln, Winchester, VA 22601
  • /54

    $439,990

    $10K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,239 Sq Ft

    142 Sequoia Dr, Winchester, VA 22602

    Some homes check the boxes. Others quietly stand apart the moment you pull up. This one does that. Not because it tries to impress, but because the setting, the layout, and the way the house sits on the land just make sense. Start with the lot. It’s a premium double-sized end-unit lot, something you simply don’t see often in townhouse communities. The home sits at the edge of the

    Alexander Bracke Real Broker, LLC

    142 Sequoia Dr, Winchester, VA 22602
  • /2

    $200,000

    • 1 Bed
    • 1 Bath

    5737 N Frederick Pike, Winchester, VA 22603

    4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable.Sold As Is With

    Tracy Link Coldwell Banker Premier

    5737 N Frederick Pike, Winchester, VA 22603
  • /39

    $315,000

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft

    126 Marple Rd, Winchester, VA 22603

    Charming Cape Cod-style home located at 126 Marple Rd in the desirable north end of Winchester! This well-maintained 3-bedroom, 1.5-bath home offers timeless character, functional living space, and a convenient commuter-friendly location. The main level features a bedroom with a 1/2 bath, a living room, a dining room, and a kitchen. Upstairs, you’ll find additional bedrooms with a shared

    RoxAnn Grimes RE/MAX Roots

    126 Marple Rd, Winchester, VA 22603
  • /36

    $360,000

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    302 Wentworth Dr, Winchester, VA 22601

    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

    Heloisa Amar Samson Properties

    302 Wentworth Dr, Winchester, VA 22601
  • /32

    $415,000

    $14K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft

    118 1/2 E Cork St, Winchester, VA 22601

    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

    Janet Flaherty Keller Williams Realty

    118 1/2 E Cork St, Winchester, VA 22601
  • /44

    $389,690

    New Construction $26K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft

    110 Sequoia Dr, Winchester, VA 22602

    Don't miss this fantastic Adams end-unit townhome with included deck, washer and dryer, and blinds! The Adams offers 4 bedrooms, 3.5 baths, and a 1-car garage spread across three levels with a total of 1,889 square feet. The main level features 9-foot ceilings, luxury vinyl plank flooring, white cabinets with quartz countertops, and stainless steel appliances by Whirlpool. With all the smart home

    Victoria Clark D R Horton Realty of Virginia LLC

    110 Sequoia Dr, Winchester, VA 22602
  • /25

    $429,900

    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft

    112 Hites St, Winchester, VA 22602

    This beautiful home features two primary suites, one on each level, offering flexibility and convenience. The upper-level primary suite includes a versatile flex space, perfect for a home office, nursery, or sitting area. Freshly painted and featuring wood floors throughout, the home is move-in ready.Additional highlights include an attached one-car garage and a desirable location in

    Rolando Sabogal First Decision Realty LLC

    112 Hites St, Winchester, VA 22602
  • /42

    $415,000

    $15K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,806 Sq Ft

    133 Woodrow Rd, Winchester, VA 22602

    Set on the east side of Winchester in Carlisle Heights, this inviting 3 bedroom, 3 full bath split foyer offers style, function, and a commuter-friendly location just minutes from Route 7. Inside, you’ll find a bright, open feel with easy-care flooring flowing through the main living spaces and bedrooms. The kitchen has been tastefully refreshed with crisp white cabinets, stainless steel

    Kevin Pringle Samson Properties

    133 Woodrow Rd, Winchester, VA 22602
  • /34

    $377,400

    $23K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,986 Sq Ft

    107 Tye Ct, Winchester, VA 22602

    PRICE REDUCED ! Why wait for new construction when the upgrades are already done for you? This move-in ready home just became even more affordable while offering the upgrades today's buyers are looking for. Enjoy the recently added spacious deck overlooking the fenced backyard, perfect for entertaining, pets, play, or simply relaxing after a long day. Built in 2023 and offering the feel of nearly

    Robin Gebhardt EXP Realty, LLC

    107 Tye Ct, Winchester, VA 22602
  • /70

    $410,000

    • 4 Beds
    • 3.5 Baths
    • 1,568 Sq Ft

    112 Ashley Dr, Winchester, VA 22602

    This well-maintained residence combines comfort, functionality, and convenience. The main level features an inviting open-concept layout filled with natural light—perfect for everyday living and entertaining. The spacious kitchen offers ample counter space, abundant cabinetry, and direct access to the rear deck, making indoor-outdoor living seamless.Upstairs, the primary suite includes a

    Martha Sanchez Spring Hill Real Estate, LLC.

    112 Ashley Dr, Winchester, VA 22602
  • /39

    $498,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,023 Sq Ft

    39 Rossmann Blvd, Winchester, VA 22602

    To be built-choose your colors and upgrades! Photos are similar and include upgrades. Beautifully crafted new home by a respected local builder, offering over 2,000 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and entertaining, that

    Marisa Varley ERA Oakcrest Realty, Inc.

    39 Rossmann Blvd, Winchester, VA 22602
  • /25

    $399,900

    New Construction
    • 3 Beds
    • 3 Baths
    • 1,914 Sq Ft

    208 Beaver Trail, Winchester, VA 22602

    95% completed and ready!Stunning 3BR/3BA home on 0.33+ acre lot with public water & available Xfinity internet. Easy entrance access. Open floor plan features vaulted family room & kitchen. Upgraded kitchen boasts Bonus Granite Island & premium cabinets. Luxury finishes include hardwood throughout the entire main floor, stairs & bedrooms, plus tile in all baths. Huge value: Almost 2,000 sq ft

    Jim Thomson Realty ONE Group Old Towne

    208 Beaver Trail, Winchester, VA 22602
  • /15

    $435,000

    • 5 Beds
    • 4 Baths
    • 2,014 Sq Ft

    122 Cherry Hill Cir, Winchester, VA 22602

    Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

    Jen Moore ERA Oakcrest Realty, Inc.

    122 Cherry Hill Cir, Winchester, VA 22602
  • /22

    $309,900

    New Construction $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,032 Sq Ft

    429 Bluebird Trail, Winchester, VA 22602

    Seller open to purchasers closing costs. It is done and ready for you! New Home Private Retreat with Views & Premium Upgrades Nestled on over half an acre with views and open 3 acre lots to the rear, this new home offers the high-end feel you want at an affordable price point. The interior boasts an open-concept design with a private primary suite separated from the guest bedrooms. Quality shines

    Jim Thomson Realty ONE Group Old Towne

    429 Bluebird Trail, Winchester, VA 22602
  • /40

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft

    225 Fox Dr, Winchester, VA 22601

    Welcome to 225 Fox Dr.! A very well maintained all brick ranch rambler. Has a fully updated kitchen with stainless steel appliances, quartz countertops, updated cabinetry with an induction oven. Very spacious open concept living room, good size bedrooms and hard flooring all around. The basement has plenty of potential and has recently been updated. The home offers paid off solar panels an EV

    Elber Olivo First Decision Realty LLC

    225 Fox Dr, Winchester, VA 22601
  • /40

    $399,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,251 Sq Ft

    709 Ross St, Winchester, VA 22601

    ***BACK ON THE MARKET, NO FAULT OF SELLER***NEW AND READY TO MOVE IN!!!BRAND NEW 3 BEDROOM, 2.5 BATH COLONIAL! NO HOA FEES AND NO HOA RULES!Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into the spacious kitchen

    Donna Anderson Samson Properties

    709 Ross St, Winchester, VA 22601
  • /27

    $429,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,168 Sq Ft

    FREEPORT DUPLEX Plan at Willow Run - Duplexes, Winchester, VA 22601

    Looking for a beautiful home that meets all your needs? Look no further than the Freeport! This stunning 1,492 square foot residence features three bedrooms, two baths, and a convenient two-car garage, all designed with your active adult lifestyle in mind. As you step into the foyer, you are greeted by the open-concept kitchen and living area with plenty of space for cooking, dining, and

    D.R. Horton Builder
    105 Trellis View Ln Unit 36406838, Winchester, VA 22601
  • /34

    $369,900

    • 2 Beds
    • 2 Baths
    • 1,219 Sq Ft

    1856 Melvor Ln, Winchester, VA 22601

    Welcome to 1856 Melvor Lane in Winchester! This charming one-level home is nestled on a corner lot in a desirable 55+ community and offers the perfect blend of comfort, convenience, and low-maintenance living. Featuring 2 bedrooms, 2 full baths, and an airy open floor plan with cathedral ceilings, the home is designed for both everyday living and easy entertaining. Recent improvements include

    Natasha Roberts Realty ONE Group Old Towne

    1856 Melvor Ln, Winchester, VA 22601
  • /7

    $489,900

    • 3 Beds
    • 2 Baths
    • 2,429 Sq Ft

    305 Amherst St, Winchester, VA 22601

    Downtown Winchester, circa 1926 foursquare. Kitchen addition, 3 bedrooms and two full baths. Walk Up attic, full basement , great yard.

    John Schroth Colony Realty

    305 Amherst St, Winchester, VA 22601
  • /23

    $449,990

    New Construction $1K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft

    124 Trellis View Ln, Winchester, VA 22602

    Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen, ideal for

    D.R. Horton Builder
    124 Trellis View Ln, Winchester, VA 22602
  • /52

    $240,000

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,173 Sq Ft

    127 8 Brookland Terrace Unit 8, Winchester, VA 22602

    Fantastic location! This spacious second-floor condo offers vaulted ceilings, generously sized rooms, and a bright, open feel throughout. Enjoy relaxing on the private deck overlooking the common area and mature trees. The floor plan features a large living room, separate dining room, two spacious bedrooms, and two full bathrooms. The primary suite includes a private bath, a large closet, and

    Meghan Pachas Realty ONE Group Old Towne

    127 8 Brookland Terrace Unit 8, Winchester, VA 22602
  • /26

    $349,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    156 Geronimo Trail, Winchester, VA 22602

    Welcome to your own private retreat in Shawneeland, where wooded surroundings, community amenities, and comfortable one-level living come together just minutes from Winchester. Tucked among mature trees on a beautifully landscaped lot, this 3-bedroom, 2-bath ranch offers the perfect blend of privacy, character, and move-in-ready comfort. The fully fenced front yard creates a peaceful outdoor

    Traci Shoberg Samson Properties

    156 Geronimo Trail, Winchester, VA 22602
  • /21

    $354,990

    New Construction $35K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 1,784 Sq Ft

    218 Monteith Dr, Winchester, VA 22601

    End of Row Townhome With All Three Finished Levels! This three level end of row townhome features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height. The first level includes a private finished recreation room and

    DRB Homes Builder
    218 Monteith Dr, Winchester, VA 22601
  • /38

    $449,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft

    1819 Reese Ct, Winchester, VA 22601

    1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

    D.R. Horton Builder
    1819 Reese Ct, Winchester, VA 22601
  • /30

    $349,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    616 Cardinal Dr, Winchester, VA 22602

    Nestled in the serene Wilde Acres community, this exquisite split foyer home, built in 2024, offers a harmonious blend of modern luxury and inviting comfort. With three spacious bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining, making it the perfect sanctuary for those who appreciate the finer things in life. Step inside to discover a thoughtfully

    Brett Shankle Samson Properties

    616 Cardinal Dr, Winchester, VA 22602
  • /34

    $363,900

    $1K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,050 Sq Ft

    621 Patterson Ave, Winchester, VA 22601

    Enchanting Cape Cod in an ideal in‐town location, this home has a welcoming ease to it, offering 3–4 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, light‐filled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainless‐steel appliances. In 2021, the home

    LESLIE WEBB Long & Foster Real Estate, Inc.

    621 Patterson Ave, Winchester, VA 22601

Showing Results 81 - 120, Page 3 of 6

How to Buy a Home How to Finance a Home How to Sell a Home