434

Winchester, VA Homes for Sale

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  • /17

    $409,900

    New Construction $10K PRICE INCREASE
    • 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 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, sleek granite

    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
  • /20

    $154,650

    • Land
    • 12.9 Acres
    • $11,988 per Acre

    0 Hodges Lot 11 Ln, Winchester, VA 22603

    Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

    Chad Pangle Whitetail Properties Real Estate, LLC

    0 Hodges Lot 11 Ln, Winchester, VA 22603
  • /31

    $565,490

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,748 Sq Ft

    227 Hydrangea Way, Winchester, VA 22602

    Experience effortless living in our Willow Run Active Adult community! Our Bristol floorplan is a thoughtfully designed 1,748 sq. ft. ranch home, 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,

    D.R. Horton Builder
    227 Hydrangea Way, Winchester, VA 22602
  • /22

    $359,990

    New Construction Open Sun 12PM - 4PM $5K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,000 Sq Ft

    117 Boone Ct, Winchester, VA 22602

    MOVE IN READY at Rossum Crossing! The St. Paul Townhome offers THREE bedrooms, TWO and a half baths, and a private one-car garage. The main level features an open-concept layout, highlighted by a spacious family room that seamlessly connects to a modern kitchen. Enjoy the kitchen’s island, pantry closet, and cozy breakfast nook—perfect for everyday living. A powder room and access to a composite

    Holly Horne Poole New Home Star Virginia, LLC

    117 Boone Ct, Winchester, VA 22602
  • /52

    $399,990

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

    ADAMS Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

    The 1,889 sq. ft. Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite counter tops, stainless steel appliances, and recessed lighting in the kitchen. Create the rec room, home office or 4th bedroom of your dreams in the lower level bonus space! The Adams comes with a 12'x10' deck off the rear of the home, perfect for outdoor

    D.R. Horton Builder
    137 Seminole Dr Unit 36203787, Winchester, VA 22602
  • /8

    $574,990

    New Construction
    • 3 - 5 Beds
    • 2 - 4 Baths
    • 2,137+ Sq Ft

    Rembrandt Plan at Hiatt Pointe at Snowden Bridge - 55+ Single Family Homes Collection, Winchester, VA 22603

    The Rembrandt is thoughtfully designed to offer a seamless balance of private and communal spaces, all while prioritizing main-level living. A covered entryway gracefully welcomes you home, leading to a central gathering area encompassing the family room, kitchen, and dining area. The kitchen is a culinary enthusiast's haven, featuring a substantial center island, ample cabinetry, and a

    Brookfield Residential Builder
    105 Wagtail Ln Unit 36578844, Winchester, VA 22603
  • /11

    $624,880

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,658 Sq Ft

    159 Williamson Rd, Winchester, VA 22602

    Richmond American Homes Builder
    159 Williamson Rd, Winchester, VA 22602
  • /26

    $419,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,094 Sq Ft

    126 Swansong Place, Winchester, VA 22603

    Exceptional value for a 4‐bedroom END‐UNIT townhome—almost ready for summer move‐in! Brand‐new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible entry‐level bedroom with full bath, a bright open‐concept main

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    126 Swansong Place, Winchester, VA 22603
  • /101

    $915,000

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

    512 S Loudoun St, Winchester, VA 22601

    Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a two-story log cabin (the blue building) likely built with timber from Fort Loudoun) , gourmet emodeled kitchen with gas cooking,

    Roxanne Watts Coldwell Banker Realty

    512 S Loudoun St, Winchester, VA 22601
  • /21

    $379,900

    • 2 Beds
    • 1.5 Baths
    • 1,186 Sq Ft

    711 E Cork St, Winchester, VA 22601

    This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

    Marco Novillo Spring Hill Real Estate, LLC.

    711 E Cork St, Winchester, VA 22601
  • /8

    $18,000

    • Land
    • 14,810 Sq Ft
    • $52,941 per Acre

    0 Tonto Trail Unit VAFV2041946, Winchester, VA 22602

    Very nice flat lot on the corner of Killbuck and Tonto Trl. This property is located om hard surface roads Potential Building lot on .34 acres located on corner of Tonto Tr. See the Beautiful mountain views coming & going. Located in Shawneeland, a beautiful mountain community with many amenities, Large Park, playground, Picnic Pavilion area, Ball field, Beach area, fishing Ponds with streams,

    Sue Fincham Samson Properties

    0 Tonto Trail Unit VAFV2041946, Winchester, VA 22602
  • /55

    $424,999

    $25K PRICE DROP
    • 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
  • /2

    $3,200,000

    • Land
    • 451 Acres
    • $7,095 per Acre

    472 Mccubbin, Winchester, VA 22601

    Adrian Small TTR Sotheby's International Realty

    472 Mccubbin, Winchester, VA 22601
  • /69

    $679,900

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft

    5039 Wardensville Grade, Winchester, VA 22602

    Need space for you and yours PLUS more than enough garage space? Look no further! Nestled on nearly 5.5 private acres, this spacious and meticulously maintained 1- owner residence offers the perfect blend of rural serenity and modern convenience. Set well back from the road and framed by towering, mature trees, the property boasts a stunning backdrop of the rolling Blue Ridge Mountains in the

    Dan Whitacre Colony Realty

    5039 Wardensville Grade, Winchester, VA 22602
  • /37

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 1,532 Sq Ft

    117 Coralyrose Ct, Winchester, VA 22602

    4 Years Young and Move-In Ready! This beautifully maintained, like-new home is nestled in a small, private community on the desirable east side of Frederick County. Enjoy a convenient location with great proximately to I81 & Rt. 7 and just minutes from shopping, parks, and all that Downtown Winchester has to offer.Step outside to your peaceful backyard retreat—perfect for morning coffee or

    Vanessa Couture Samson Properties

    117 Coralyrose Ct, Winchester, VA 22602
  • /7

    $1,150,000

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,947 Sq Ft

    60 Gravenstein Ct, Winchester, VA 22602

    MAIN LEVEL LIVING in an Idyllic Setting - Welcome to Stonymeade ! -2 acre Home Site in Winchester Virginia Base price shown is for the Dogwood MAIN LEVEL LIVING FLOORPLAN and we have many other plans including those with first floor primary suites, farmhouse kitchens, and multi-generational options. All homes include exceptional standard features including 10' main level ceilings, Hardwood

    Daniel Boris Pearson Smith Realty, LLC

    60 Gravenstein Ct, 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
  • /31

    $899,900

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

    230 Conifer Ln, Winchester, VA 22602

    Perched on a picturesque knoll with sweeping mountain views, this thoughtfully designed modern farmhouse colonial offers the perfect balance of luxury, comfort, and peaceful country living—without sacrificing modern convenience. Built in 2018, this 4-bedroom, 3-bath home offers over 3,100 square feet of beautifully designed living space with 9-foot ceilings on all three levels, creating an open,

    Traci Shoberg Samson Properties

    230 Conifer Ln, Winchester, VA 22602
  • /3

    $3,200,000

    • Land
    • 13.05 Acres
    • $245,211 per Acre

    0 0 Northwestern Pike, Winchester, VA 22602

    Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities,

    Sarah Reynolds Keller Williams Realty

    0 0 Northwestern Pike, 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

    $20K PRICE DROP
    • 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
  • /6

    $584,900

    Open Sun 12PM - 2PM Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,344 Sq Ft

    219 Bentley Ave, Winchester, VA 22602

    219 Bentley Avenue — Coming Soon! Located in desirable Chapel Hill just outside of Winchester city limits, this one-owner home is being offered for sale for the very first time. Conveniently located near shopping, dining, schools, and commuter routes, this spacious three-level home offers the perfect blend of comfort, functionality, and opportunity.The main level features a cozy yet spacious

    Tiffany Hunter ERA Oakcrest Realty, Inc.

    219 Bentley Ave, Winchester, VA 22602
  • /73

    $469,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,703 Sq Ft

    231 Bentley Ave, Winchester, VA 22602

    Easy main-level living with bonus space when you need it—this one just works. A beautiful, covered front porch welcomes you into a foyer that opens to a comfortable living room centered around a gas fireplace with built-ins, creating a space that feels both open and inviting. Toward the rear of the home, the dining area is filled with natural light from well-placed windows. The kitchen is

    Natalie Langford ERA Oakcrest Realty, Inc.

    231 Bentley Ave, Winchester, VA 22602
  • /40

    $609,990

    New Construction $4K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 2,818 Sq Ft

    121 Scented Rose Way, Winchester, VA 22602

    Experience effortless living in our Willow Run Active Adult community! Our Bristol floorplan is a thoughtfully designed 1,748 sq. ft. ranch home, 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

    D.R. Horton Builder
    121 Scented Rose Way, Winchester, VA 22602
  • /39

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    102 Cromwell Ct, Winchester, VA 22602

    Welcome home to this beautifully maintained property tucked away on a quiet cul-de-sac! This inviting home offers a spacious 2-car garage, great curb appeal, and a functional layout designed for everyday living. Step outside onto the rear deck, perfect for relaxing, entertaining, or enjoying peaceful evenings outdoors. Pride of ownership is evident throughout, making this home truly move-in

    Julie Teets ERA Oakcrest Realty, Inc.

    102 Cromwell Ct, Winchester, VA 22602
  • /9

    $9,500

    • Land
    • 23,958 Sq Ft
    • $17,273 per Acre

    LOTS 8 & 9 Elk Trail, Winchester, VA 22602

    Great opportunity to own two beautiful wooded lots full of mature trees and plenty of privacy! These adjoining parcels offer a wonderful chance to connect with nature and enjoy peaceful surroundings. Located just about 30 minutes from downtown Winchester, you get the perfect mix of country calm and town convenience. Whether you’re thinking about outdoor fun, future plans, or simply an investment,

    Kristin Crosby Samson Properties

    LOTS 8 & 9 Elk Trail, Winchester, VA 22602
  • /96

    $1,049,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 3,100 Sq Ft

    2225 Cedar Grove Rd, Winchester, VA 22603

    5-9-26 BEAUTY DONE/READY! Pictures are of subject property.Seize a truly unique opportunity to own a brand-new, luxury estate set on over 7 acres of private, wooded land. While this stunning property sits at the entrance to the prestigious, upper-scale 15-lot Keplinger Estates community, it does not have HOA, offering unparalleled freedom and privacy.Tucked gracefully off the main road,

    Jim Thomson Realty ONE Group Old Towne

    2225 Cedar Grove Rd, Winchester, VA 22603
  • /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
  • /47

    $539,900

    $59K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,837 Sq Ft

    1317 Caroline St, Winchester, VA 22601

    Welcome to 1317 Caroline Street, a well-appointed brick rancher in a fantastic Winchester location that perfectly balances professional convenience with residential comfort. Situated just minutes from Winchester Medical Center and major commuter routes, this home offers an effortless transition from a busy day to a relaxing evening. This sense of ease begins the moment you step inside the main

    Dan Whitacre Colony Realty

    1317 Caroline St, Winchester, VA 22601
  • /22

    $389,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    HOMESITE 22 Shouner Ct, Winchester, VA 22602

    110 SHUONER Ct – Model Home | Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger Deck Beautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom. Home Highlights Open-concept main level –

    Jimmy Thomas New Home Star Virginia, LLC

    HOMESITE 22 Shouner Ct, Winchester, VA 22602
  • /4

    $320,000

    Open Sun 1PM - 3PM Coming Soon
    • 3 Beds
    • 1.5 Baths
    • 1,222 Sq Ft

    317 Fairview Ave, Winchester, VA 22601

    PICTURES COMING SOON. Fully Renovated SFH in Historic Winchester! Prime location. Just minutes from charming Historic Downtown Winchester featuring local shops, restaurants, entertainment, and more! Beautifully Updated throughout. This charming home offers bright, inviting living spaces with modern finishes and thoughtfully updates designed for comfortable everyday living. w Just Move Right In!

    Donna Lutkins Real Broker, LLC

    317 Fairview Ave, Winchester, VA 22601
  • /42

    $749,900

    • 3 Beds
    • 3 Baths
    • 2,112 Sq Ft

    1049 Laurel Grove Rd, Winchester, VA 22602

    Discover the perfect blend of privacy, comfort, and natural beauty in this custom-built 3-bedroom, 3-bath retreat, set on a private, wooded lot with expansive mountain views. From the moment you arrive, the property feels like a peaceful getaway—quiet, scenic, and surrounded by nature—yet still just minutes from everyday conveniences. The main-level primary suite offers a true escape with its

    LESLIE WEBB Long & Foster Real Estate, Inc.

    1049 Laurel Grove Rd, Winchester, VA 22602
  • /50

    $1,179,000

    • 4 Beds
    • 5 Baths
    • 4,920 Sq Ft

    1004 Heth Place, Winchester, VA 22601

    A Stunning Brick Colonial residence graced by meticulously manicured gardens and lush vegetation, cocooning the property in a tranquil and private ambiance. Offering an array of amenities, each of its three immaculately finished floors mirrors the care bestowed upon the surrounding gardens. Generously proportioned rooms bathed in natural light enhance the spacious open plan living areas,

    Kathryn Hallett Long & Foster Real Estate, Inc.

    1004 Heth Place, Winchester, VA 22601
  • /10

    $468,900

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft

    121 Travis Ct, Winchester, VA 22602

    Beautifully updated colonial in an established neighborhood just minutes from Winchester shopping, dining, and commuter routes! This spacious home features a newly remodeled kitchen with quartz countertops, freshly painted cabinetry, newer appliances, and plenty of space for cooking and gathering. Fresh paint throughout, refinished hardwood floors, and brand-new carpet give the home a bright,

    Donna Anderson Samson Properties

    121 Travis Ct, Winchester, VA 22602
  • /46

    $524,990

    New Construction $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    253 Rossmann Blvd, Winchester, VA 22602

    The home is vacant, move-in ready, and includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering almost 2,300 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

    Marisa Varley ERA Oakcrest Realty, Inc.

    253 Rossmann Blvd, Winchester, VA 22602
  • /52

    $574,900

    • 4 Beds
    • 2.5 Baths
    • 2,428 Sq Ft

    104 Monet Terrace, Winchester, VA 22602

    Located in an established cul-de-sac this 4 bedrooms, 2 1⁄2 bath, home has an unfinished basement. Also a deep two vehicle garage and storage building with a fenced yard and rear covered porch. The kitchen has Corian counters and loads of beautiful cabinets, an arch pass through, and hardwood floors. The house has crown molding, chair rail, wainscoting and hardwood floors throughout the main

    Janet Jackson MarketPlace REALTY

    104 Monet Terrace, Winchester, VA 22602
  • /77

    $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
  • /52

    $290,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    700 Tomahawk Trail, Winchester, VA 22602

    Welcome to this charming ranch-style home situated on a spacious .44-acre corner lot in the desirable Shawneeland community. Thoughtfully updated and well maintained, this home offers comfort, functionality, and modern touches throughout. The kitchen has been enhanced with a newly added pantry (2026) making everyday living and entertaining effortless. The primary bedroom features French doors

    Lindsey Gomes Real Broker, LLC

    700 Tomahawk Trail, Winchester, VA 22602
  • /69

    $605,000

    • Studio
    • 4,396 Sq Ft

    540 Monticello St, Winchester, VA 22601

    Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

    Laura King MarketPlace REALTY

    540 Monticello St, Winchester, VA 22601

Showing Results 281 - 320, Page 8 of 11

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