382

Winchester, VA Homes for Sale

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  • /23

    $399,855 New Construction

    • 4 Beds
    • 3.5 Baths
    • 1,658 Sq Ft

    210 Monteith Dr, Winchester, VA 22601

    OPEN HOUSE: Friday - Sunday 1pm - 3pm Beautiful open concept living 3 level townhome with Lower Level Walkout and Bedroom! The Bedford II 3 level interior town home with a box bay window with 1 car garage featuring 4 Bedrooms and 3.5 Baths and 1,658 square feet. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the spacious lower-level

    DRB Homes Builder
    210 Monteith Dr, Winchester, VA 22601
  • /42

    $503,929 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,181 Sq Ft

    116 Keystone, Winchester, VA 22603

    Embrace the Vera 30-F2 – Homesite 1097 at Hiatt Pointe—a two-car, front-load garage END UNIT VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa

    Shannon L Bray Pearson Smith Realty, LLC

    116 Keystone, Winchester, VA 22603
  • /5

    $422,539 New Construction

    • 4 Beds
    • 3.5 Baths
    • 1,658 Sq Ft

    201 Monteith Dr, Winchester, VA 22601

    OPEN HOUSE: Friday - Sunday 1pm - 3pm End Of Row Townhome With 1 Car Garage, Lower Level Bedroom & Rear Deck! MOVE-IN READY! The Bedford II 3 level with 1 car garage featuring 4 Bedrooms and 3.5 Baths and 1,658 square feet. The front door with the electronic Smart Home Technology package leads directly into the spacious lower-level recreation room with 9 ft. ceilings. The foyer with luxury vinyl

    DRB Homes Builder
    201 Monteith Dr, Winchester, VA 22601
  • /22

    $899,999 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,320 Sq Ft

    Melody Plan at Abrams Pointe, Winchester, VA 22602

    The open, inviting layout of the ranch-style Melody plan makes entertaining easy. Inside, you'll find an expansive great room, a generous dining room and a well-appointed kitchen featuring a center island and roomy walk-in pantry. An elegant owner's suite boasts an oversized walk-in closet and private bath, and two additional bedrooms invite rest and relaxation. A laundry, mudroom and second full

    Richmond American Homes Builder
    101 Abrams Pointe Blvd Unit 37822593, Winchester, VA 22602
  • /44

    $492,669 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,187 Sq Ft

    114 Keystone, Winchester, VA 22603

    Embrace the Vera 30-F2 – Homesite 1096 at Hiatt Pointe—a two-car, front-load garage VILLA HOME with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel

    Shannon L Bray Pearson Smith Realty, LLC

    114 Keystone, Winchester, VA 22603
  • /37

    $215,000

    • Land
    • 10.77 Acres
    • $19,963 per Acre

    0 Brush Creek Rd Unit LotWP002, Winchester, VA 22603

    This land is located north of Winchester in the Cross Junction area of the county. Part of what was once a much larger family farm, and on the market for the first time since the 1950's. Access is secured via extensive road frontage on paved and state-maintained Brush Creek Road. A terrific location for your next country home. An electricity service line is already running on the property, making

    Chad Pangle Whitetail Properties Real Estate

    0 Brush Creek Rd Unit LotWP002, Winchester, VA 22603
  • /60

    $395,000

    • 3 Beds
    • 1 Bath
    • 1,582 Sq Ft

    859 Brush Creek Rd, Winchester, VA 22603

    This rustic home on acreage is located north of Winchester in the Cross Junction area of the county. On the market for the first time since the 1950’s the home features 3 bedrooms, 1 bathroom, and nearly 1600 +/- square feet of living space. Access is secured via extensive road frontage on paved and state maintained Brush Creek Road. Electricity, well, and septic are already installed

    Chad Pangle Whitetail Properties Real Estate, LLC

    859 Brush Creek Rd, Winchester, VA 22603
  • /66

    $1,200,000

    • Land
    • 124 Acres
    • $9,677 per Acre

    0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603

    Here’s a piece of pristine land on the market for the first time since the late 70’s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family-owned and operated for decades. It is a mix of mostly flat hay ground and wooded acreage that stretches to the top

    Chad Pangle Whitetail Properties Real Estate

    0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603
  • /41

    $77,700

    • Land
    • 6.09 Acres
    • $12,759 per Acre

    440 Iris Ln, Winchester, VA 22602

    Owner Financing Available! (see details below)Enjoy breathtaking, unrivaled views of the Shenandoah Valley below from this ridgetop property on Little North Mountain.Property Overview:Address: 440 Iris Lane, Winchester, VA 22602Size: 6.09 AcresKey Features:Gorgeous Sunset Valley ViewsTwo Lots in One Build on Both or Split Off!Extensive Road

    Robert Scott AcreTown.com

    440 Iris Ln, Winchester, VA 22602
  • /23

    $168,000

    • Land
    • 10 Acres
    • $16,800 per Acre

    0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602

    Enjoy rural living and fun on this building lot in the Long Ridge Estates community. This prime building lot is located off of Gough Road in the High View Manor area of the county. This parcel has a septic certification letter on record with the county health department for a four-bedroom septic system. Access is secured via a 50 ft deeded access easement, which has already been installed and

    Chad Pangle Whitetail Properties Real Estate

    0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602
  • /48

    $550,000

    • 3 Beds
    • 1.5 Baths
    • 2,177 Sq Ft

    216 Fairmont Ave, Winchester, VA 22601

    Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your

    Dave Spence RE/MAX Roots

    216 Fairmont Ave, Winchester, VA 22601
  • /46

    $599,900

    • 3 Beds
    • 2 Baths
    • 1,946 Sq Ft

    289 Westview Dr, Winchester, VA 22603

    Welcome to your private contemporary retreat at 289 Westview Drive in Winchester, VA! This truly exceptional property offers the ultimate escape, situated on over 13 magnificent acres with gorgeous mature trees, stunning views, and unparalleled peace and quiet. Step inside the sun-filled main level, featuring an open layout that seamlessly connects the living room, dining room, and kitchen.

    Dan Whitacre Colony Realty

    289 Westview Dr, Winchester, VA 22603
  • /46

    $569,000

    • 4 Beds
    • 2.5 Baths
    • 2,275 Sq Ft

    326 Lehigh Dr, Winchester, VA 22602

    Welcome to 326 Lehigh Drive, a stunning, like-new home in a prime Winchester location—a pristine, only 2-year-old residence that feels brand new! This beautiful 4-bedroom, 2.5-bathroom home boasts exceptional high-end finishes and a modern, desirable design throughout. The interior showcases an airy open-concept layout and a stylish neutral color palette that allows any decorating style to

    Dan Whitacre Colony Realty

    326 Lehigh Dr, Winchester, VA 22602
  • /62

    $579,990

    • 4 Beds
    • 3.5 Baths
    • 3,132 Sq Ft

    308 Lehigh Dr, Winchester, VA 22602

    Welcome to 308 Lehigh Drive — where space, style, and comfort all come together.The main level opens with a chef’s kitchen built to impress — gas cooktop, built-in wall oven and microwave, butler’s pantry, upgraded counters, and absolutely tons of cabinet space! The large morning room off the kitchen is bright and open, featuring a large sliding glass door that leads to the backyard — perfect

    Sean Smith Real Broker, LLC

    308 Lehigh Dr, Winchester, VA 22602
  • /62

    $599,900

    • 5 Beds
    • 3.5 Baths
    • 5,298 Sq Ft

    212 Fairfield Dr, Winchester, VA 22602

    Welcome to 212 Fairfield Drive, a sprawling, all-brick rancher offering an incredible amount of space and comfort in a highly sought-after Winchester location. This home is a commuter's dream, providing easy access to I-81 and other major commuter routes all while offering a peaceful, private retreat. The main level is designed for both entertaining and daily living, featuring a formal dining

    Dan Whitacre Colony Realty

    212 Fairfield Dr, Winchester, VA 22602
  • /48

    $545,000

    • 5 Beds
    • 4 Baths
    • 2,288 Sq Ft

    144 Morning Glory Dr, Winchester, VA 22602

    Extraordinary 5-Bedroom Home with Pool and Dual Kitchens in Winchester This exceptional 5-bedroom, 3.5-bathroom home — complete with a private office — offers comfort, functionality, and modern elegance. Thoughtfully designed for both everyday living and relaxed entertaining, this residence features two fully renovated kitchens (one on the main level and one in the walkout basement), perfect for

    Julieta Russell Keller Williams Realty Dulles

    144 Morning Glory Dr, Winchester, VA 22602
  • /59

    $635,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 4,632 Sq Ft

    930 Wayne Dr, Winchester, VA 22601

    Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy fireplace. To the right, you’ll find a spectacular

    Elizabeth Flood Keller Williams Realty

    930 Wayne Dr, Winchester, VA 22601
  • /42

    $498,900

    • 4 Beds
    • 3.5 Baths
    • 3,884 Sq Ft

    700 Crow Dr, Winchester, VA 22602

    Welcome to 700 Crow Drive, situated in the beautiful Wilde Acres subdivision in Frederick County, VA. This lovingly cared for and well-maintained three-level colonial home offers four bedrooms and three and a half baths, showcasing both space and style throughout. Priced below the tax assessment, this home presents an incredible opportunity for its next owners. The owners have truly loved this

    Deisi Hernandez Fairfax Realty Select

    700 Crow Dr, Winchester, VA 22602
  • /45

    $515,900

    • 3 Beds
    • 2.5 Baths
    • 2,444 Sq Ft

    339 Lanny Dr, Winchester, VA 22601

    Right off of Amherst St. in sought after Whittier Acres, we are proud to present 339 Lanny Drive. This home is solid brick and sits on a fenced park-like .4 acre lot. Everything about this 2.716 square foot home will be appreciated and it is completely move-in ready. In 2024, just about everthing was replaced. In 2025 the new owner did even further improvements. The list is long: New roof,

    Lisette Turner Century 21 Redwood Realty

    339 Lanny Dr, Winchester, VA 22601
  • /115

    $499,999

    • 5 Beds
    • 3 Baths
    • 2,080 Sq Ft

    419 Summit Ave, Winchester, VA 22601

    Welcome Home!This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment.With 5

    Waqas Abbasi Lifestyle Realty, LLC.

    419 Summit Ave, Winchester, VA 22601
  • /32

    $540,000

    • 3 Beds
    • 2 Baths
    • 1,829 Sq Ft

    105 Lenore Ln, Winchester, VA 22602

    Former Richmond American model home — Exceptionally maintained with top-tier builder upgrades and designer detail. This one-level, 3-bedroom, 2-bath home spans 1,829 square feet and showcases the quality and design you’d expect from a builder’s showcase property.High ceilings and an open layout create a bright, spacious feel throughout. The kitchen features upgraded cabinetry, quartz

    Barton Chasler Realty ONE Group Old Towne

    105 Lenore Ln, Winchester, VA 22602
  • /45

    $499,900

    • 4 Beds
    • 4 Baths
    • 3,359 Sq Ft

    227 Miller St, Winchester, VA 22601

    Charming Downtown Winchester Home with Four Finished Levels. Welcome to 227 Miller Street, where timeless character and abundant living space come together in the heart of downtown Winchester. This inviting 4-bedroom, 4-bathroom home offers four fully finished levels that radiate warmth, comfort, and a true sense of home. Step onto the spacious covered front porch, a perfect spot to enjoy your

    Leah Marabella Realty ONE Group Old Towne

    227 Miller St, Winchester, VA 22601
  • /61

    $524,000

    • 4 Beds
    • 2.5 Baths
    • 2,098 Sq Ft

    129 Old Wagon Rd, Winchester, VA 22602

    "Outstanding On Old Wagon" This 4 bedroom, 2 1/2 bath colonial style home sits in a cul-de-sac in the highly desirable Pioneer Heights Neighborhood. This home has had a ton of upgrades over the years! Gorgeous, updated custom kitchen with Frigidaire Gallery Appliances, custom built cabinets with pull out shelves, extra depth cabinet over the refrigerator, Corian Quartz Countertops, large

    Matt Kilmer Samson Properties

    129 Old Wagon Rd, Winchester, VA 22602
  • /42

    $499,900

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    420 W Cork St, Winchester, VA 22601

    Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is

    Dan Whitacre Colony Realty

    420 W Cork St, Winchester, VA 22601
  • /56

    $489,999

    • 3 Beds
    • 2.5 Baths
    • 2,412 Sq Ft

    109 Shelby Ct, Winchester, VA 22602

    Welcome to this beautiful colonial home in the sought-after Chapel Hill community. Set on a flat, quarter-acre lot, it pairs a fully fenced, beautifully landscaped backyard with the convenience of a two-car garage. Inside, the main level is warm and welcoming: a separate dining room for gatherings and a bright family room anchored by a gas fireplace and plenty of natural light.The kitchen

    Omar Khatib DMV Realty, INC.

    109 Shelby Ct, Winchester, VA 22602
  • /44

    $549,990

    • 4 Beds
    • 2.5 Baths
    • 2,534 Sq Ft

    121 Raven Oaks Dr, Winchester, VA 22602

    Motivated Seller!!! HUGE UNFINISHED BASEMENT! Immaculately maintained, this like-new home offers the space, style, and modern features you deserve! One standout is the large unfinished basement -clean, open, and already equipped with rough plumbing for a future bathroom. Whether you envision extra storage, a spacious in-law suite, or the ultimate entertainment retreat, the possibilities are

    Rachel Lowell Trowbridge Realty Corporation

    121 Raven Oaks Dr, Winchester, VA 22602
  • /94

    $545,000

    • 4 Beds
    • 3.5 Baths
    • 2,976 Sq Ft

    2812 Ridgetop Ct, Winchester, VA 22601

    HUGE PRICE IMPROVEMENT! Welcome to this beautiful "picture perfect" brick front 4-bedroom, 3.5-bath home in the desirable Rolling Hills community of Winchester, VA. Perfectly located at the end of a cul-de-sac in an established (and sought after) neighborhood, this one-owner property has been meticulously maintained and is ready for its next chapter.Inside, you’ll find a spacious and inviting

    Sara Duncan RE/MAX Distinctive Real Estate

    2812 Ridgetop Ct, Winchester, VA 22601
  • /60

    $519,000

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

    121 N Washington St, Winchester, VA 22601

    A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet kitchen with brand new state of art appliances includes wine fridge, drawer style microwave, and pot filler. Formal living/dining room(s). Extras include den, office(s), nooks, and 3rd floor bonus room (perfect for kid's getaway). Laundry hook-ups on both main level and 2nd level. This home has been

    M. Kelly Walker RE/MAX Roots

    121 N Washington St, Winchester, VA 22601
  • /42

    $479,900

    • 3 Beds
    • 2.5 Baths
    • 1,976 Sq Ft

    703 National Ave, Winchester, VA 22601

    Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enhance its curb appeal. Inside, you’ll find brand-new bathrooms with updated lighting, vanities,

    Jennifer Sacco RE/MAX Roots

    703 National Ave, Winchester, VA 22601
  • /53

    $555,000

    • 4 Beds
    • 2.5 Baths
    • 3,490 Sq Ft

    120 Armstrong Place, Winchester, VA 22602

    Your opportunity to live next to the Golf course/Winchester Country Club in Fairway Estates! Spacious brick rancher with a finished basement and a 2-car garage. 2 gas fireplaces and 1 wood burning.Many updates to include: Roof 2021, HVAC's 2018, furnace serviced annually, water heater 2010, sump pump 2015, sunroom roof 2024, leaf filters & gutters, new garage door 2023, new smoke detectors

    Sheila Pack RE/MAX Roots

    120 Armstrong Place, Winchester, VA 22602
  • /65

    $524,000

    • 4 Beds
    • 2.5 Baths
    • 1,958 Sq Ft

    341 Warm Springs Rd, Winchester, VA 22603

    What a find! Gorgeous views with this 4BR 2.5BA Colonial situated on 1.22 acre lot. Features main level family room, living room, dining room and kitchen. Enjoy the screened in porch with hot tub; refreshing in ground pool with privacy fence. 2 car garage, basement for added comfort. Must see to appreciate!

    Toni Carone Long & Foster Real Estate, Inc.

    341 Warm Springs Rd, Winchester, VA 22603
  • /90

    $515,000

    • 3 Beds
    • 2.5 Baths
    • 1,984 Sq Ft

    2623 Middle Rd, Winchester, VA 22601

    Welcome home to 2623 Middle Rd! Now with a Virtual Tour of this beautiful home! Located near all that Winchester has to offer, Middle Rd is a lovely private oasis to come home to. With a myriad of upgrades including a gorgeous screened in back porch, this home offers many conveniences, a spacious layout and bedrooms, and plenty of room for entertainment, hobbies, and whatever you can dream of.

    Nicole Lewis Coldwell Banker Premier

    2623 Middle Rd, Winchester, VA 22601
  • /41

    $535,000

    • 3 Beds
    • 2 Baths
    • 2,517 Sq Ft

    101 Dutton Place, Winchester, VA 22601

    Seller Motivated! Welcome to 101 Dutton Place— Location, Location, Location! + One Level living! Nestled just inside the Frederick County line in the highly sought-after Merrimans Estates community. This beautifully maintained ranch-style home is ideally situated on a peaceful and meticulously landscaped 1.26-acre lot, minutes from WMC Hospital, downtown Winchester & major commuter routes! Step

    Lisa Behr Coldwell Banker Premier

    101 Dutton Place, Winchester, VA 22601
  • /114

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 1,798 Sq Ft

    720 S Kent St, Winchester, VA 22601

    Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods.Inside, you’ll find nearly 1,800 square feet of

    Krissy Cruse Pearson Smith Realty, LLC

    720 S Kent St, Winchester, VA 22601
  • /71

    $455,000

    • 3 Beds
    • 2.5 Baths
    • 2,012 Sq Ft

    4403 Back Mountain Rd, Winchester, VA 22602

    Nestled on two private wooded acres, 4403 Back Mountain Road in Winchester, VA offers a peaceful country retreat with no HOA or restrictions. Built in 2001, this traditional Colonial-style home features approximately 2,012 square feet of comfortable finished living space, including three bedrooms and two and a half baths . The walk-out basement provides excellent storage and potential for future

    RoxAnn Grimes RE/MAX Roots

    4403 Back Mountain Rd, Winchester, VA 22602
  • /51

    $430,000

    • 4 Beds
    • 2 Baths
    • 1,773 Sq Ft

    133 Cardinal Ln, Winchester, VA 22602

    Welcome to this well maintained and fully remodeled split foyer, tucked away in a private cul-de-sac setting. Located just minutes from route 7 and I-81, commuting will be a breeze. Brand new LVP flooring flow seamlessly across both levels, as does the neutral colors throughout. The spacious eat-in kitchen is the heart of the home-with white cabinetry, granite countertops, tile backsplash and

    Heloisa Amar Samson Properties

    133 Cardinal Ln, Winchester, VA 22602
  • /36

    $379,900

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    1243 N Frederick Pike, Winchester, VA 22603

    Welcome to 1243 N Frederick Pike, a charming all-brick ranch home where peaceful living meets ultimate accessibility. This beautiful property features three comfortable bedrooms and two full bathrooms, centered around a bright, spacious living room. You'll appreciate the low-maintenance elegance of hardwood floors that flow throughout the entire main level. Adding significant value is the

    Dan Whitacre Colony Realty

    1243 N Frederick Pike, Winchester, VA 22603
  • /41

    $410,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 2,250 Sq Ft

    114 Biscane Ct, Winchester, VA 22602

    Bright 3 Bedroom, 3.5 Bath Townhome Built by Van Metre. This 3 Level Home Shows Beautifully with 2250 sq ft of Living Space and 9ft Ceilings. The Main Level Features a Lovely Center Island Kitchen with Pantry, Brand New LVP Flooring (2024), Backsplash (2023), Microwave (2023), and Newer Fridge (2022). The Main Level also offers a Dining Room with a Breakfast Nook, Powder Room, and Large Living

    Kate Herzig EXP Realty, LLC

    114 Biscane Ct, Winchester, VA 22602
  • /25

    $384,000

    • 3 Beds
    • 1 Bath
    • 1,918 Sq Ft

    1327 Front Royal Pike, Winchester, VA 22602

    Don't miss this opportunity to own this wonderful, well maintained home. Just minutes from town, this home has hardwood floors throughout and a bright, sunny sunroom facing the spacious back yard. There is a huge shop in the back that would be prefect for the car enthusiast or for additional garage space. The woodstove in the basement rec room would save on heating costs and includes a cute art

    Katherine Solenberger Colony Realty

    1327 Front Royal Pike, Winchester, VA 22602
  • /60

    $815,000

    • 4 Beds
    • 3.5 Baths
    • 4,461 Sq Ft

    162 Janes Way, Winchester, VA 22602

    Discover this beautifully updated home on 5 private acres in the sought-after Brookneill Subdivision—just minutes from Winchester! The home includes numerous updates, including new hardwood floors through the living room, and stairs, new kitchen cabinets, countertops, sink, and appliances. Upstairs features two huge bedrooms with new carpet, the finished basement offers new luxury vinyl plank

    Tanner Pack RE/MAX Roots

    162 Janes Way, Winchester, VA 22602

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