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Colonial Homes for Sale in Winchester, VA

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  • /64

    $374,900 New Construction

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

    506 Grouse Dr, Winchester, VA 22602

    Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025,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

    Steve DuBrueler Coldwell Banker Premier

    506 Grouse Dr, Winchester, VA 22602
  • /27

    $399,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    211 Inca Trail, Winchester, VA 22602

    4-28-26 To be completion early May. Painted and hardwoods finished! Cabinets next. Getting close.Current Shawneeland Inventory208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail103 Tonto Trail123 Killbuck Trail116 Pinto TrailPremium Finishes: Enjoy a builder-upgraded interior featuring gleaming hardwood floors throughout the entire home (including

    Jim Thomson Realty ONE Group Old Towne

    211 Inca Trail, Winchester, VA 22602
  • /40

    $399,900 New Construction

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

    709 Ross St, Winchester, VA 22601

    ***PRICE REDUCTION***NEW AND READY TO MOVE IN!!!BRAND NEW 3 BEDROOM, 2.5 BATH COLONIAL! NO HOA FEES AND NO SUBDIVISION 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 featuring an

    Donna Anderson Samson Properties

    709 Ross St, Winchester, VA 22601
  • /79

    $860,000

    • 5 Beds
    • 5.5 Baths
    • 6,256 Sq Ft

    150 Ewell Dr, Winchester, VA 22602

    Welcome to Equestrian Estates, a highly sought-after Winchester community with no HOA, where space, style, and flexibility come together beautifully. This stately 5-bedroom, 6-bath Colonial offers over 6,700 square feet of finished living space on nearly 3 private acres, creating the perfect setting for both everyday living and entertaining. The home was not available for showings over the past

    Sherry Santmyer Hunt Country Sotheby's International Realty

    150 Ewell Dr, Winchester, VA 22602
  • /40

    $421,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,277 Sq Ft

    422 S Loudoun St, Winchester, VA 22601

    Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level

    Dana Cloud Realty ONE Group Old Towne

    422 S Loudoun St, Winchester, VA 22601
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    $1,200,000

    • 4 Beds
    • 6 Baths
    • 3,877 Sq Ft

    1617 Merrimans Ln, Winchester, VA 22602

    Set on 7 picturesque acres, this exceptional property in Merrifield Estates offers space, comfort, and versatility both inside and out. The home, designed by Hilton Head architect Eric Moser and later built by Ritter Construction features 4 generously sized bedrooms and 4 full and 2 half bathrooms, with a well-designed layout that includes a main level primary suite, formal living room with

    John Scully Colony Realty

    1617 Merrimans Ln, Winchester, VA 22602
  • /11

    $699,900

    • Studio
    • 3,190 Sq Ft

    434 Fairmont Ave, Winchester, VA 22601

    ATTENTION ALL INVESTORS OR FUTURE LANDLORDS COME CHECKOUT THIS MULTI FAMILY 3 UNIT PROPERTY. IT CONSIST OF 2 HOUSES. EACH UNIT IS A 2 BED 1BATH EACH HAVE STOVE REFRIGERATOR MICROWAVE WASHER DRYER. CURRENTLY FULLY RENTED. SO NOW IS YOUR CHANCE TO OWN A TURNKEY RENTAL PROPERTY ALL WELL MAINTAINED WITH OFF STREET PARKING. CLOSE TO DOWNTOWN & SHOPPINGRESTRICTED SHOWINGS. NEW PIC'S COMING SOON.

    Richard Kozlowski Long & Foster Real Estate, Inc.

    434 Fairmont Ave, Winchester, VA 22601
  • /22

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft

    625 Watson Ave, Winchester, VA 22601

    Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features new cabinets, granite countertops, stainless steel appliances, a new sink and faucet, and vinyl plank flooring. The bathroom includes a new vanity, vanity

    Jennifer Sacco RE/MAX Roots

    625 Watson Ave, Winchester, VA 22601
  • /17

    $399,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    123 Killbuck Trail, Winchester, VA 22602

    Current Shawneeland Inventory208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail103 Tonto Trail123 Killbuck Trail116 Pinto TrailPremium 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,

    Jim Thomson Realty ONE Group Old Towne

    123 Killbuck Trail, Winchester, VA 22602
  • /94

    $950,000

    • 6 Beds
    • 4.5 Baths
    • 4,714 Sq Ft

    226 Summerfield Dr, Winchester, VA 22602

    Nestled in the charming and sought-after Raven Pointe neighborhood,adjacent to farmland yet 7 minutes from Old Town Winchester, thisstunning Colonial home offers a perfect blend of modern comfort andtimeless elegance. This spacious residence boasts 4,714 finishedsquare feet, providing ample room for both relaxation andentertainment. Front porch entrance greets guests with a

    Rebecca Sims Century 21 Redwood Realty

    226 Summerfield Dr, Winchester, VA 22602
  • /108

    $1,325,000

    • 5 Beds
    • 4.5 Baths
    • 4,100 Sq Ft

    100 Country Club Cir, Winchester, VA 22602

    This regal 1950s Colonial, named Eagle Gate, sits atop a knoll overlooking 6.34 pastoral acres on the east side of Winchester. This elegant home dazzles with nearly 4,000 finished square feet, three levels, five bedrooms, 4.5 baths, an expansive garage, a swimming pool, and renovations and updates that elevate the living experience to decadent. Majestic pillars are the hallmark of the handsome

    Dan Whitacre Colony Realty

    100 Country Club Cir, Winchester, VA 22602
  • /31

    $915,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 4,330 Sq Ft

    512 S Loudoun St, Winchester, VA 22601

    Pictures posted by May 08.. Distinctive home on the historic register, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester. Gorgeous inside and out. Fully renovated, 4 levels with a log cabin room (in the blue building), remodeled kitchen with gas cooking, large pantry, eat=in space by the window. All three full and two half baths

    Roxanne Watts Coldwell Banker Realty

    512 S Loudoun St, Winchester, VA 22601
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    $429,999

    • 4 Beds
    • 2.5 Baths
    • 2,850 Sq Ft

    1105 Henry Dr, Winchester, VA 22602

    Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring through out both levels (absolutely no carpet) that features 4 bedrooms and 2.5 baths situated on over a 1/2 acre (.61) of ground. Upon entering you will find an open floor plan that encompasses a large living room and dining room with canned lighting then pours into the large eat in kitchen (new appliances) that

    James Amick RE/MAX Roots

    1105 Henry Dr, Winchester, VA 22602
  • /22

    $625,000

    • 5 Beds
    • 2 Baths
    • 1,948 Sq Ft

    446 N Loudoun St, Winchester, VA 22601

    Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

    Lawrence Lessin Homes By Owner, Inc.

    446 N Loudoun St, Winchester, VA 22601
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    $899,900

    • 4 Beds
    • 3 Baths
    • 3,943 Sq Ft

    230 Conifer Ln, Winchester, VA 22602

    Stunning Modern Farmhouse Colonial with Breathtaking Mountain Views Welcome to this exceptional modern farmhouse colonial, perfectly positioned to capture sweeping mountain views—especially from the inviting front porch. Nestled on a picturesque knoll, the home overlooks a tranquil pond and a landscape dotted with beautiful, stately homes. Enjoy frequent wildlife sightings and the peaceful charm

    Traci Shoberg Samson Properties

    230 Conifer Ln, Winchester, VA 22602
  • /49

    $850,000 New Construction

    • 5 Beds
    • 3 Baths
    • 3,057 Sq Ft

    Lot 5 Keval Gyan Way, Winchester, VA 22603

    Model available to see! Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of a large family

    Jim Thomson Realty ONE Group Old Towne

    Lot 5 Keval Gyan Way, Winchester, VA 22603
  • /74

    $869,000

    • 5 Beds
    • 3.5 Baths
    • 3,800 Sq Ft

    107 Launchris Dr, Winchester, VA 22602

    Step into timeless elegance with this stately Colonial, set on nearly an acre of picturesque land. Blending classic charm with thoughtful modern upgrades, this home offers the perfect balance of comfort, space, and sophistication. The current owner has invested over $150,000 in upgrades since purchasing, including a fully renovated HVAC system with all-new ductwork and high-end components

    Laura White ERA Oakcrest Realty, Inc.

    107 Launchris Dr, Winchester, VA 22602
  • /50

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    129 Doonbeg Ct, Winchester, VA 22602

    ENJOY YOUR RETIREMENT! Newer, beautifully maintained 4-bedroom home with open floor plan and upgrades. On a pleasant cul-de-sac in Cottage Glen, an age 55-plus community that's convenient to I-81 and Rt. 37 and near restaurants, shopping, services, regional Medical Center and historic downtown Winchester. National publications and TV have hailed Winchester as a prime location for retirement.

    Teresa Strohmeyer ERA Oakcrest Realty, Inc.

    129 Doonbeg Ct, Winchester, VA 22602
  • /55

    $469,900

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    620 Crystal Ct, Winchester, VA 22601

    Back and better than EVER! New Sales Price!! Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly $20,000 under appraisal value!! Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready

    VAIBHAV AGARWAL Realty FC, LLC

    620 Crystal Ct, Winchester, VA 22601
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    $699,000

    • 4 Beds
    • 3.5 Baths
    • 3,120 Sq Ft

    256 Brookneil Dr, Winchester, VA 22602

    Step into something special at 256 Brookneil Dr—where space, privacy, and flexibility come together beautifully. Nestled on 2.1 wooded acres just minutes from Winchester, this property offers a peaceful retreat with the soothing sounds of nature all around. Whether you're sipping coffee on the deck or unwinding after a long day, the setting delivers the kind of tranquility that’s hard to find.

    Jacquelyn Sowers ERA Oakcrest Realty, Inc.

    256 Brookneil Dr, Winchester, VA 22602
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    $1,050,000

    • 4 Beds
    • 4 Baths
    • 5,069 Sq Ft

    1460 Pitcock Ln, Winchester, VA 22602

    Escape to Your Private Retreat – Just 10 Minutes from Winchester!Don’t miss the 3D tour attached to this listing! Welcome to a truly one-of-a-kind property offering 27.65 secluded acres across three parcels, complete with towering trees, a tranquil pond, and breathtaking natural surroundings. This charming log home is rich with character and history—originally relocated here in the 1960s,

    Sheila Pack RE/MAX Roots

    1460 Pitcock Ln, Winchester, VA 22602
  • /59

    $674,900

    • 4 Beds
    • 3.5 Baths
    • 3,924 Sq Ft

    146 Darby Dr, Winchester, VA 22602

    Beautiful brick-front home in sought-after Ravenwing offering three finished levels and exceptional space throughout! This 4-bedroom, 3.5-bath home features a welcoming main level with formal living and dining rooms, plus a cozy family room with a gas fireplace—perfect for relaxing or entertaining.Dual staircases lead to the expansive upper level, highlighted by two owner’s suites, each with

    Traci Shoberg Samson Properties

    146 Darby Dr, Winchester, VA 22602
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    $459,000

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft

    228 Cavalry Dr, Winchester, VA 22602

    Cul-de-sac setting, a front porch you’ll actually use, and a backyard designed to enjoy—this home makes everyday living easy. Located in Pioneer Heights on the east side of Winchester, this home offers a practical layout with thoughtful updates throughout. The kitchen is both functional and inviting with granite countertops, a 5-burner gas cooktop, stainless steel appliances, and an island for

    Natalie Langford ERA Oakcrest Realty, Inc.

    228 Cavalry Dr, Winchester, VA 22602
  • /65

    $585,000

    • 3 Beds
    • 3.5 Baths
    • 3,465 Sq Ft

    450 Fishel Rd, Winchester, VA 22602

    Welcome to this 3-bed, 3-and-a-half-bath all-brick estate offering the perfect blend of privacy, space, and convenience, set on 4 picturesque wooded acres just 15 minutes from Winchester and close to major commuter routes. The main level features a welcoming living room with a gas fireplace, a formal dining room, a spacious kitchen with Corian counters, and convenient first-floor laundry.

    Kristin Higy Dandridge Realty Group, LLC

    450 Fishel Rd, Winchester, VA 22602
  • /52

    $565,000

    • 4 Beds
    • 3.5 Baths
    • 2,989 Sq Ft

    1300 Caroline St, Winchester, VA 22601

    Welcome to 1300 Caroline Street—where timeless design meets everyday functionality in one of Winchester’s most convenient locations. Perfectly positioned on a spacious 0.31-acre corner lot, this beautifully maintained residence offers 4 bedrooms, 3.5 bathrooms, a finished basement, and a desirable 2-car side-load garage. The main level showcases a thoughtfully renovated kitchen featuring updated

    Lisa Behr Hunt Country Sotheby's International Realty

    1300 Caroline St, Winchester, VA 22601
  • /45

    $479,900 Open House 5/10

    • 3 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    703 S Loudoun St, Winchester, VA 22601

    Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood

    Kristin Crosby Samson Properties

    703 S Loudoun St, Winchester, VA 22601
  • /36

    $350,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    513 Pheasant Dr, Winchester, VA 22602

    Welcome to this newly built colonial in Wilde Acres situated on 1/4 acre lot nestled among the trees and surrounded by a wall made of native stone. Upon entry, enjoy the open living area and wood floors which make the space warm and comfortable. The galley kitchen offers ample counterspace and new stainless steel appliances. The convenient main level full bath also has hookup for stackable washer

    Ismael Carino MarketPlace REALTY

    513 Pheasant Dr, Winchester, VA 22602
  • /8

    $689,000

    • 4 Beds
    • 2.5 Baths
    • 3,108 Sq Ft

    1950 Melvor Ln, Winchester, VA 22601

    Step into this meticulously maintained colonial home, a testament to quality craftsmanship and thoughtful design by Richmond American Homes. Situated in the desirable Meadow Branch South neighborhood, this residence offers an exceptional living experience with a perfect balance of formal and casual spaces This home is situated in a vibrant community with easy access to major roads, shopping, and

    Kim Kroner Washington Dulles Real Estate Group

    1950 Melvor Ln, Winchester, VA 22601
  • /50

    $565,000 Open House 5/16

    • 4 Beds
    • 2.5 Baths
    • 3,414 Sq Ft

    3336 Hunting Ridge Rd, Winchester, VA 22603

    Colonial home 21 yrs young on 5 acres in Frederick county 4 bedroom 2 full baths with 1 half bath ., Whole house freshly painted in Jan/Feb 2025, laundry on main level with large pantry and large eat in kitchen with breakfast bar, granite countertops (new in Jan/Feb 2025) Family room formal dining room and living room (currently being used as a dining room) Large flat back yard with above ground

    Leslie Carter Carter Real Estate, Inc.

    3336 Hunting Ridge Rd, Winchester, VA 22603

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