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Winchester, VA Open Houses

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  • /2

    $449,000 Open Sun 2PM - 4:30PM

    • 4 Beds
    • 4.5 Baths
    • 1,913 Sq Ft

    315 National Ave, Winchester, VA 22601

    Fully reimagined for modern living while preserving its timeless charm, this stunning 1910 home in the heart of Downtown Winchester offers the perfect blend of character, luxury, and value. Completely renovated from top to bottom, every detail has been thoughtfully updated—delivering the feel of new construction within a classic architectural setting.This spacious residence features 4

    Agent Photo

    Carlos Soares

    Samson Properties

    (540) 787-2197

    315 National Ave, Winchester, VA 22601
  • /40

    $445,000 Open Sat 2PM - 4PM

    • 5 Beds
    • 3 Baths
    • 1,917 Sq Ft

    623 Smithfield Ave, Winchester, VA 22601

    Spacious split-foyer home in the heart of Winchester featuring 5 bedrooms and 3 full bathrooms, plus a versatile bonus room in the basement ideal for a variety of uses. Well-maintained and located in a convenient neighborhood with no HOA.

    Agent Photo

    Carlos Soares

    Samson Properties

    (540) 253-3199

    623 Smithfield Ave, Winchester, VA 22601
  • /30

    $295,000 Open Fri 11AM - 12:45PM

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    704 Watson Ave, Winchester, VA 22601

    Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for

    Agent Photo

    Carlos Soares

    Samson Properties

    (540) 530-4023

    704 Watson Ave, Winchester, VA 22601
  • /65

    $389,990 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 1,536 Sq Ft

    317 Gray Ave, Winchester, VA 22601

    Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

    Agent Photo

    Matthew Abregu

    Keller Williams Realty

    (540) 701-3590

    317 Gray Ave, Winchester, VA 22601
  • /17

    $489,000 Open Sun 12PM - 3PM

    • 3 Beds
    • 1.5 Baths
    • 1,698 Sq Ft

    312 W Cecil St, Winchester, VA 22601

    Don’t miss your chance to live on sought-after W. Cecil in this charming, beautifully maintained historic home, just a few blocks from the walking mall. Light-filled and inviting, this home welcomes you with a classic covered front porch and warm hardwood floors that set the tone for the character throughout. The cozy living room features a recently converted gas fireplace, lovely built-ins, and

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    (540) 405-6463

    312 W Cecil St, Winchester, VA 22601
  • /3

    $799,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,331 Sq Ft

    123 Stetson St, Winchester, VA 22603

    Don’t miss this incredible opportunity to own a brand-new ranch home set on 2.66 beautiful acres, conveniently located near shopping and commuter routes to Winchester, Martinsburg, and Northern Virginia and approximately 10 minutes from the Winchester Medical Center. This thoughtfully designed home features an open-concept layout with a desirable split-bedroom design, offering both comfort and

    Agent Photo

    Brett Sowder

    RE/MAX Roots

    (540) 619-5465

    123 Stetson St, Winchester, VA 22603
  • /37

    $399,500 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft

    1033 Sunnyside Dr, Winchester, VA 22603

    Welcome to 1033 Sunnyside Drive, a beautifully renovated bungalow tucked away on a quiet street just minutes from historic downtown Winchester. This charming home blends classic character with modern upgrades, creating a warm and inviting place to call home.Start your day on the inviting 9’ x 11’ tiled front porch, complete with new railings and stairs, the perfect spot for morning coffee or

    Tien Dao Redfin Corporation

    1033 Sunnyside Dr, Winchester, VA 22603
  • /74

    $364,900 Open Fri 4PM - 5:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    707 E Cork St, Winchester, VA 22601

    Charming Colonial in Winchester, VA 3 Bedrooms | 2.5 Baths with additional rooms Step into timeless charm with this beautifully maintained Colonial featuring gleaming hardwood floors throughout, including a stunning custom square inlay design that adds character you simply won’t find in today’s homes.The home offers two full baths full of personality — one with a beautifully tiled shower and

    Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

    707 E Cork St, Winchester, VA 22601
  • /47

    $875,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 5.5 Baths
    • 5,054 Sq Ft

    125 Skyjes Ln, Winchester, VA 22602

    Custom-built Craftsman designed with comfort, flexibility, and intergenerational living in mind! This thoughtfully designed home, on 2 acres, welcomes you with an oversized family room featuring soaring 12-foot ceilings and an electric fireplace with a gas line already in place. A separate formal dining room with a stunning wall of windows creates the perfect setting for gatherings and holiday

    Angie Bresnahan Pearson Smith Realty, LLC

    125 Skyjes Ln, Winchester, VA 22602
  • /57

    $645,000 Open Fri 4PM - 6PM

    • 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
  • /65

    $585,000 Open Sun 2PM - 4PM

    • 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
  • /28

    $329,000 Open Sat 3PM - 5PM

    • 2 Beds
    • 1 Bath
    • 1,132 Sq Ft

    419 Stone Meadow Ct, Winchester, VA 22601

    Tucked away on a quiet cul-de-sac in the desirable Stonecrest Village community, 419 Stone Meadow Court offers a perfect blend of comfort, style, and convenience. Built in 1997 and thoughtfully maintained by its single in-residence owner, this charming home features easy one-level living with a spacious, light-filled layout ideal for both everyday living and entertaining. Recent updates include

    Alice Shank Samson Properties

    419 Stone Meadow Ct, Winchester, VA 22601
  • /48

    $559,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,279 Sq Ft

    104 Wagtail Ln, Winchester, VA 22603

    Welcome to the Vale at Hiatt Pointe—a brand-new 2025 end-unit villa that is ready for immediate move-in. This beautifully upgraded two-car front-load garage home features three bedrooms, two full baths, and one half bath, offering the perfect blend of style, comfort, and convenience.Enjoy peace of mind with remaining builder warranties, plus the upcoming 1-year builder walkthrough, adding

    Kathrin Donovan Keller Williams Realty

    104 Wagtail Ln, Winchester, VA 22603
  • /15

    $89,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft

    411 Eckard Cir, Winchester, VA 22602

    Welcome to this beautifully maintained, move-in-ready 2022 ranch-style manufactured home, thoughtfully cared for by its original owner. The open floor plan features a spacious kitchen with abundant countertop space that flows seamlessly into the dining area, great for everyday living and entertaining. Just off the kitchen, the inviting living room creates a comfortable setting to relax and

    Steven Koleno BEYCOME BROKERAGE REALTY LLC

    411 Eckard Cir, Winchester, VA 22602
  • /44

    $1,200,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 5,426 Sq Ft

    410 Valley View Dr, Winchester, VA 22603

    Discover Your Private Estate: 9.83 Acres of Country Charm with Resort-Style Amenities. NO HOA! Step into the unexpected with this exceptional property, perfectly blending the tranquility of a country retreat with the convenience of being just minutes from town. The inviting entry to the front door welcomes you into a beautifully maintained home, featuring three finished levels, five bedrooms, and

    Brenda Miller Berkshire Hathaway HomeServices PenFed Realty

    410 Valley View Dr, Winchester, VA 22603
  • /39

    $535,000 Open Sat 12PM - 2PM

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

    105 Lenore Ln, Winchester, VA 22602

    Welcome to this better-than-new former model home, built in 2024 and thoughtfully upgraded throughout—Offering the ideal blend of style, space, and value, this move-in ready home features an open-concept layout, 10' ceilings, a beautifully upgraded kitchen with modern finishes, and spacious living areas designed for both everyday comfort and entertaining. Generously sized bedrooms and

    Kelly Vornadore New Dimensions Realty Group LLC

    105 Lenore Ln, Winchester, VA 22602
  • /80

    $655,000 Open Sun 1PM - 3PM

    • 3,546 Sq Ft

    113 Edgar Ln, Winchester, VA 22602

    Welcome to 113 Edgar Lane in the heart of Winchester, VA—where modern design meets everyday comfort in this beautifully crafted 2023 home. Offering 4 spacious bedrooms and 2.5 baths, this nearly new residence is thoughtfully upgraded throughout and ready to impress.Step inside to discover a bright, open floor plan filled with natural light, creating an inviting and airy atmosphere from the

    Lynna Hall Pearson Smith Realty, LLC

    113 Edgar Ln, Winchester, VA 22602
  • /61

    $695,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 3,399 Sq Ft

    108 Nevermore Dr, Winchester, VA 22602

    OPEN SAT AND SUN 1-3 PM Welcome to 108 Nevermore Drive, nestled in the sought-after Raven Oaks community of Winchester, where comfort, energy efficiency, and thoughtful design come together seamlessly. From the moment you arrive, this home welcomes you with a sense of space and possibility. Inside, the open-concept main level flows effortlessly through the family room, gourmet kitchen, and a

    Mike Dotterweich RE/MAX Gateway, LLC

    108 Nevermore Dr, Winchester, VA 22602
  • /45

    $385,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    540 Eagle Place, Winchester, VA 22601

    Great opportunity for a rental investment! This well-maintained one-level rancher is tucked away in a quiet cul-de-sac, offering both convenience and long-term potential. With its prime location within walking distance to the university and easy access to Route 81, downtown, and the Apple Blossom Mall, this property is ideal for investors or owner-occupants alike. Inside, you’ll find easy,

    Camryn Jeremiah NextHome Realty Select

    540 Eagle Place, Winchester, VA 22601
  • /55

    $585,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    308 Ridge Ave, Winchester, VA 22601

    Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry

    John Scully Colony Realty

    308 Ridge Ave, Winchester, VA 22601
  • /62

    $715,000 Open Sat 11:30AM - 2:30PM

    • 2 Beds
    • 3 Baths
    • 4,808 Sq Ft

    121 Windrow Ct, Winchester, VA 22602

    Exquisite Home In Frederick County VA. This Custom Built Ranch Style Home Is The Perfect One Level Living Home, With Over 5,000 Finished Square Feet Of Living Space. The Open Living Concept Offers 9+ Foot Ceilings, High Loft Ceiling With Custom Wooden Decorative Beams And Floor To Ceiling Fireplace In Main Living Room With Decorative Wood Trim And Mantle, Kitchen To Living Room Space With Full

    Tracy Link Coldwell Banker Premier

    121 Windrow Ct, Winchester, VA 22602
  • /46

    $435,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    25 W Southwerk St, Winchester, VA 22601

    ***OPEN HOUSE THIS SATURDAY, APRIL 18th, FROM 11-1pm!!!***Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home

    Dan Whitacre Colony Realty

    25 W Southwerk St, Winchester, VA 22601
  • /28

    $399,000 Open Sun 1PM - 4PM

    • 3 Beds
    • 1 Bath
    • 2,683 Sq Ft

    307 Fox Run Ln, Winchester, VA 22602

    Wake up to breathtaking views of the Shenandoah Valley every day in this peaceful, beautifully renovated cottage. Completely updated in 2024, the home blends modern amenities with warm, inviting charm.The bright, open living space features a vaulted ceiling and abundant natural light, creating an airy, welcoming atmosphere. The living room showcases large windows, custom built-ins, and a

    Karen Sparks Corcoran McEnearney

    307 Fox Run Ln, Winchester, VA 22602
  • /46

    $550,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,837 Sq Ft

    1317 Caroline St, Winchester, VA 22601

    ***OPEN HOUSE THIS SUNDAY, APRIL 19th, FROM 12-2pm!!!***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

    Dan Whitacre Colony Realty

    1317 Caroline St, Winchester, VA 22601
  • /51

    $489,999 Open Sat 10:30AM - 12:30PM

    • 3 Beds
    • 3 Baths
    • 2,483 Sq Ft

    3466 Middle Rd, Winchester, VA 22602

    Welcome to a private retreat where timeless charm meets peaceful mountain beauty. Set on 0.59 acres of fully fenced, professionally landscaped grounds, this all-brick hillside home offers breathtaking views of the Blue Ridge Mountains along a quiet stretch of Middle Road. Inside, sunlight pours through expansive living spaces, creating a warm and inviting atmosphere. The open-concept design flows

    LESLIE WEBB Long & Foster Real Estate, Inc.

    3466 Middle Rd, Winchester, VA 22602
  • /53

    $609,990 Open Sat 12PM - 3PM

    • 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 kitchen,

    Brooks Sears D R Horton Realty of Virginia LLC

    121 Scented Rose Way, Winchester, VA 22602
  • /47

    $599,990 Open Sat 12PM - 3PM

    • 4 Beds
    • 3 Baths
    • 2,865 Sq Ft

    117 Scented Rose Way, Winchester, VA 22602

    Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 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 kitchen opens to a large great room with two windows that let in

    Brooks Sears D R Horton Realty of Virginia LLC

    117 Scented Rose Way, Winchester, VA 22602
  • /23

    $780,000 Open Fri 4PM - 6PM

    • 3,476 Sq Ft

    230 Tranquil Wood Ln, Winchester, VA 22602

    NO HOA! APRIL-MAY READY TO MOVE IN! Are you in search of a spacious, one-level living home that combines privacy and the freedom of no HOA restrictions? Your search ends here—introducing Tranquil Wood Ln showcasing the exquisite Dogwood Model! Inspired by the tree it draws its name from, this charming residence is a true masterpiece, reflecting the superior craftsmanship of the acclaimed Water

    Monique Rodriguez Pearson Smith Realty LLC

    230 Tranquil Wood Ln, Winchester, VA 22602
  • /64

    $374,900 Open Sat 11AM - 2PM

    • 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
  • /5

    $499,900 Open House 4/25

    • 4 Beds
    • 3.5 Baths
    • 2,782 Sq Ft

    203 Alpine Meadow Rd, Winchester, VA 22602

    Located on a quiet cul-de-sac within the established and highly sought-after Apple Ridge neighborhood on the desirable east side of Winchester, this 4-bedroom, 3.5-bathroom colonial offers a spacious and open floor plan with significant recent improvements! The prime location provides quick access to Route 7 and I-81, making it an ideal choice for commuters! The exterior features a covered front

    Charles Witt Nova Home Hunters Realty

    203 Alpine Meadow Rd, Winchester, VA 22602
  • /29

    $335,000 Open House 4/25

    • 3 Beds
    • 4 Baths
    • 1,336 Sq Ft

    120 Worsham Terrace, Winchester, VA 22602

    This beautifully maintained 3 level townhome is a great place to call home. Perfectly situated at the back of the subdivision, you get the benefits of the community while enjoying the quiet surroundings. Enjoy the toddler playground and the walking/running trail just steps from your door. This home is also the perfect commuter location less than a mile from Route 7 and Interstate 81. Only minutes

    Marielle Thoburn Keller Williams Realty

    120 Worsham Terrace, Winchester, VA 22602

Home Trends in Winchester, VA

Housing Trends

Median Sale Price
$415,000
Median Single Family Sale Price
$450,000
Median Townhouse Sale Price
$399,990
Median 2 Bedroom Sale Price
$259,000
Average Price Per Sq Ft
$209
Number of Homes for Sale
288
Last 12 months Home Sales
1,201
Months of Supply
2.90
Median List Price
$430,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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