Winchester, VA Homes

/6
$20,000
- Land
- 0.46 Acre
- $43,478 per Acre
Lot 102 Bow Wood Trail, Winchester, VA 22602

A Hidden Gem Waiting for YouNestled in the serene countryside of Winchester, Virginia, lies a great treed building lot on the lower side of Shawneeland. This picturesque piece of land offers the perfect blend of seclusion and convenience, making it an ideal location for building your dream home.Enjoy the tranquility and natural beauty of Shawneeland's private parks, perfect for relaxing

Rick Guthrie Keller Williams Realty

Lot 102 Bow Wood Trail, Winchester, VA 22602
/28
$399,900 Sold Jun 30, 2025

116 Ware Place, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,657 Sq Ft
- Built 1995
Last Sold Summary
- $241/SF
- 5 Days On Market
Current Estimated Value $409,318

Last Listing Agent Kristin Cobb Berkshire Hathaway HomeServices PenFed Realty

116 Ware Place, Winchester, VA 22602

/20
Est $309,418 Not Listed For Sale

3113 Papermill Rd, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 895 Sq Ft
- Built 1956
3113 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- 3% Above List Price
- $335/SF
- 11 Days On Market
Last Sold Price $300,000

Last Listing Agent Marcy Cantatore Atoka Properties | Middleburg Real Estate

/45
$450,000 Open Sat 11AM - 5PM
- 4 Beds
- 2.5 Baths
- 2,636 Sq Ft
100 Winns Cir, Winchester, VA 22602

Welcome home to Winns Circle! This is a fantastic opportunity for future homeowners to live in a bright, spacious home on the east side of Winchester, as the home is listed under the tax assessed value, as well as the most recently appraised value of $487,700 (completed 1/21/2026 and available to qualified buyers upon request) and the After Repair Value of $522, 700, as noted on the appraisal.

Nicole Lewis Coldwell Banker Premier

100 Winns Cir, Winchester, VA 22602
/47
$295,000 Sold Nov 03, 2025

2964 Grace St, Winchester, VA 22601
- 2 Beds
- 1 Bath
- 780 Sq Ft
- Built 1955
Last Sold Summary
- $378/SF
- 22 Days On Market
Current Estimated Value $295,149

Last Listing Agent Jane Norton United Real Estate Premier

2964 Grace St, Winchester, VA 22601

/37
Est $351,458 Not Listed For Sale

2905 First St, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,584 Sq Ft
- Built 1968
2905 First St, Winchester, VA 22601

Last Sold Summary
- 12% Above List Price
- $199/SF
- 11 Days On Market
Last Sold Price $315,000

Last Listing Agent Melissa Johnston ERA Oakcrest Realty, Inc.

/8
$1,095,000 Pending
- 4 Beds
- 3.5 Baths
- 3,707 Sq Ft
62 Gravenstein Ct, Winchester, VA 22602

Welcome to Stonymeade ! -2 acre Home Site in Winchester Virginia Base price shown is for the Huntwick Farm 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 floors, upgraded cabinetry and countertops, extensive trim

Daniel Boris Pearson Smith Realty, LLC

62 Gravenstein Ct, Winchester, VA 22602
/45
$500,000 Sold Oct 15, 2025

436 W Leicester St, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,592 Sq Ft
- Built 1925
Last Sold Summary
- $314/SF
Current Estimated Value $497,774

Last Listing Agent Jeanne Mezzatesta Colony Realty

436 W Leicester St, Winchester, VA 22601

/6
Est $288,547 Not Listed For Sale

3037 Papermill Rd, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
- Built 1960
3037 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- 5% Above List Price
- $273/SF
- 21 Days On Market
Last Sold Price $275,000

Last Listing Agent Brett Sowder RE/MAX

/12
$290,000
- 2 Beds
- 1 Bath
- 817 Sq Ft
580 York Ave, Winchester, VA 22601

Charming and completely updated! This beautiful home features a brand-new kitchen with new appliances, an updated bathroom, newly installed HVAC system, and a new water heater. Truly move-in ready and waiting for its next owner!

Yoselin Mejia The Vasquez Group LLC

580 York Ave, Winchester, VA 22601
/30
$329,400 Sold Aug 08, 2025

613 Watson Ave, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 1,668 Sq Ft
- Built 1946
Last Sold Summary
- $197/SF
- 4 Days On Market
Current Estimated Value $321,750

Last Listing Agent Teri Domanski Corcoran McEnearney

613 Watson Ave, Winchester, VA 22601

/24
Est $329,575 Not Listed For Sale

2959 S Pleasant Valley Rd, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,199 Sq Ft
- Built 1989
2959 S Pleasant Valley Rd, Winchester, VA 22601

Last Sold Summary
- 14% Above List Price
- $242/SF
- 5 Days On Market
Last Sold Price $290,000

Last Listing Agent Anna Fox NextHome Realty Select

/20
$439,900 Pending
- 3 Beds
- 3 Baths
- 1,935 Sq Ft
109 Glen Ridge Rd, Winchester, VA 22602

New construction! Pictures are if similar model. Conveniently located just minutes from town, this home offers comfort and style. With 3 bedrooms and 3 full baths, you will find many features such as beautiful hardwood floors throughout the main level, primary bedroom with walk in closet and bath with walk in shower, crown molding, granite counter top, 2 car garage and so much more! Don't miss

Pamela Russell CENTURY 21 New Millennium

109 Glen Ridge Rd, Winchester, VA 22602
/40
$449,990 Sold Aug 12, 2025

1827 Reese Ct, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 1,923 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $234/SF
- 6 Days On Market
D.R. Horton Abrams Crossing at Meadow Branch

1827 Reese Ct, Winchester, VA 22601

/21
Est $329,917 Not Listed For Sale

121 Summit Ave, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,020 Sq Ft
- Built 1981
121 Summit Ave, Winchester, VA 22601

Last Sold Summary
- 2% Above List Price
- $318/SF
- 9 Days On Market
Last Sold Price $324,500

Last Listing Agent Heloisa Amar Samson Properties

/25
$279,900
- 2 Beds
- 1 Bath
- 924 Sq Ft
111 Genesee Trail, Winchester, VA 22602

Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Front deck to be stained as soon as weather permits. Shawnee Land is in a sanitary

Jacquelyn Rizzari MarketPlace REALTY

111 Genesee Trail, Winchester, VA 22602
/13
$190,000 Sold Jan 02, 2026

163 Cabin Ln, Winchester, VA 22603
- 3 Beds
- 2 Baths
- 2,430 Sq Ft
- Built 1977
Last Sold Summary
- $78/SF
- 10 Days On Market
Current Estimated Value $288,667

Last Listing Agent Kerry Wysong Long & Foster Real Estate, Inc.

163 Cabin Ln, Winchester, VA 22603

/40
Est $295,594 Not Listed For Sale

2937 Grace St, Winchester, VA 22601
- 2 Beds
- 1 Bath
- 851 Sq Ft
- Built 1962
2937 Grace St, Winchester, VA 22601

Last Sold Summary
- 15% Above List Price
- $302/SF
- 0 Days On Market
Last Sold Price $257,000

Last Listing Agent Kathrin Donovan Keller Williams Realty

/51
$1,595,000
- Land
- 158.44 Acres
- $10,067 per Acre
158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602

Incredible opportunity to own 158.443 acres of pristine, private land in an exclusive 3-lot, 440-acre subdivision. This is the most secluded parcel of the three, offering unmatched 360-degree panoramic views and a level of privacy that’s increasingly rare—yet just 15 minutes from town. Tucked away from the lights and sounds of civilization, this property provides a peaceful, off-the-beaten-path

Nadeem Helfer Corcoran McEnearney

158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602
/36
$525,000 Sold Nov 14, 2025

2723 Windwood Dr, Winchester, VA 22601
- 3 Beds
- 3 Baths
- 2,726 Sq Ft
- Built 1999
Last Sold Summary
- $193/SF
- 38 Days On Market
Current Estimated Value $530,125

Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

2723 Windwood Dr, Winchester, VA 22601

/25
Est $381,684 Not Listed For Sale

2921 Second St, Winchester, VA 22601
- 4 Beds
- 3 Baths
- 1,147 Sq Ft
- Built 1955
2921 Second St, Winchester, VA 22601

Last Sold Summary
- 2% Below List Price
- $340/SF
- 39 Days On Market
Last Sold Price $389,999

Last Listing Agent Joelle Graham Weichert Corporate

/2
$549,990 New Construction
- 3 Beds
- 2 Baths
- 1,958 Sq Ft
118 Scented Rose Way, Winchester, VA 22602

The Dover by D.R. Horton offers 1,958 square feet of thoughtfully designed, single-level living with 3 bedrooms, 2 full baths, and a 2-car garage. A private flex room with LVP flooring sits just off the foyer – ideal for a home office or craft room. 9-foot ceilings lead into the open-concept kitchen, dining, and family room. The kitchen features quartz countertops, soft-close cabinet doors, a gas

Brooks Sears D R Horton Realty of Virginia LLC

118 Scented Rose Way, Winchester, VA 22602
/47
$555,000 Sold Dec 22, 2025

2307 Stoneridge Rd, Winchester, VA 22601
- 5 Beds
- 3.5 Baths
- 3,280 Sq Ft
- Built 2016
Last Sold Summary
- $169/SF
- 5 Days On Market
Current Estimated Value $556,931

Last Listing Agent Dave Spence RE/MAX Roots

2307 Stoneridge Rd, Winchester, VA 22601

/22
Est $298,222 Not Listed For Sale

313 Summit Ave, Winchester, VA 22601
- 2 Beds
- 1 Bath
- 954 Sq Ft
- Built 1951
313 Summit Ave, Winchester, VA 22601

Last Sold Summary
- 5% Above List Price
- $299/SF
- 25 Days On Market
Last Sold Price $285,000

Last Listing Agent Susan Wathen EXP Realty, LLC

/45
$405,990 Under Contract
- 3 Beds
- 2 Baths
- 1,763 Sq Ft
137 Woodrow Rd, Winchester, VA 22602

Welcome home to this spacious 3-bedroom, 2-bath split foyer with a finished lower level offering extra living space for a rec room, office, or guest area. Enjoy the added value of a rough-in for a future full bath and the convenience of a 1-car garage. This home is move in ready. The home has been freshly painted, lower level has new carpet, HVAC and Hot Water Heater replaced in 2023. New Roof

Pamela Baber Coldwell Banker Premier

137 Woodrow Rd, Winchester, VA 22602
/18
$454,990 Sold Aug 13, 2025

106 Manasquan Way, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 1,665 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $273/SF
- 13 Days On Market
D.R. Horton Retreat at Winding Creek - Single Family

106 Manasquan Way, Winchester, VA 22602

/29
Est $306,766 Not Listed For Sale

2917 First St, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,250 Sq Ft
- Built 1952
2917 First St, Winchester, VA 22601

Last Sold Summary
- 12% Above List Price
- $220/SF
- 90 Days On Market
Last Sold Price $275,000

Last Listing Agent James King RE/MAX

/45
$449,000 Coming Soon
- 3 Beds
- 2.5 Baths
- 1,904 Sq Ft
25 W Southwerk St, Winchester, VA 22601

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 offers the perfect balance of neighborhood tranquility and

Dan Whitacre Colony Realty

25 W Southwerk St, Winchester, VA 22601
/36
$390,000 Sold Aug 22, 2025

103 Sequoia Dr, Winchester, VA 22602
- 3 Beds
- 3.5 Baths
- 2,238 Sq Ft
- Built 2016
Last Sold Summary
- $174/SF
- 3 Days On Market
Current Estimated Value $397,507

Last Listing Agent Barton Chasler Realty ONE Group Old Towne

103 Sequoia Dr, Winchester, VA 22602

/31
Est $285,147 Not Listed For Sale

2944 Second St, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 850 Sq Ft
- Built 1953
2944 Second St, Winchester, VA 22601

Last Sold Summary
- 13% Above List Price
- $298/SF
- 126 Days On Market
Last Sold Price $253,300

Last Listing Agent Amira Wali Spring Hill Real Estate, LLC.

/33
$576,990 New Construction
- 3 Beds
- 2 Baths
- 1,865 Sq Ft
55 Hydrangea 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

55 Hydrangea Way, Winchester, VA 22602
/36
$370,000 Sold May 13, 2025

520 N Loudoun St, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,459 Sq Ft
- Built 1930
Last Sold Summary
- $254/SF
- 32 Days On Market
Current Estimated Value $367,766

Last Listing Agent Dan Whitacre Colony Realty

520 N Loudoun St, Winchester, VA 22601

/19
Est $326,135 Not Listed For Sale

2928 First St, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,472 Sq Ft
- Built 1972
2928 First St, Winchester, VA 22601

Last Sold Summary
- 23% Above List Price
- $180/SF
- 11 Days On Market
Last Sold Price $265,000

Last Listing Agent Kimberly Schroeder Long & Foster Real Estate, Inc.

/45
$509,990 Pending
- 4 Beds
- 3 Baths
- 2,168 Sq Ft
118 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 and finished loft. 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

118 Trellis View Ln, Winchester, VA 22602
/9
$95,000 Sold Aug 22, 2025

1114 Cedar Grove Rd, Winchester, VA 22603
- 1 Bed
- 1 Bath
- Built 1957
Last Sold Summary
- 84 Days On Market
Current Estimated Value $92,500

Last Listing Agent Dave Spence RE/MAX Roots

1114 Cedar Grove Rd, Winchester, VA 22603

/8
Est $243,912 Not Listed For Sale

521 Monticello St, Winchester, VA 22601
- 2 Beds
- 1.5 Baths
- 1,064 Sq Ft
- Built 1981
521 Monticello St, Winchester, VA 22601

Last Sold Summary
- 16% Above List Price
- $197/SF
- 4 Days On Market
Last Sold Price $210,000

Last Listing Agent Ned Stock BHHS PenFed (actual)

/12
$632,990 New Construction
- 3 Beds
- 2 Baths
- 3,056 Sq Ft
5 Williamson Rd, Winchester, VA 22602

Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites. The Drexel Floorplan is a spacious and versatile single-family home designed to suit a variety of lifestyles. With up to 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features

Dick Bryan New Home Star Virginia, LLC

5 Williamson Rd, Winchester, VA 22602
/2
$346,900 Sold Oct 14, 2025

111 Comanche Trail, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,422 Sq Ft
- Built 1992
Last Sold Summary
- $244/SF
- 2 Days On Market
Current Estimated Value $343,431

Last Listing Agent George Glaize George W. Glaize, Jr., Inc. REALTOR

111 Comanche Trail, Winchester, VA 22602

/22
Est $250,372 Not Listed For Sale

514 Armour Dale, Winchester, VA 22601
- 2 Beds
- 1 Bath
- 765 Sq Ft
- Built 1955
514 Armour Dale, Winchester, VA 22601

Last Sold Summary
- 1% Above List Price
- $325/SF
- 4 Days On Market
Last Sold Price $249,000

Last Listing Agent Katy Kidwell Burch Real Estate Group, LLC

/6
$8,500 Under Contract
- Land
- 0.26 Acre
- $32,692 per Acre
0 Lot 50 Cardinal Dr, Winchester, VA 22602

Affordable lot in Wilde Acres / Mountain Falls Park in Winchester, VA! This 0.26-acre lot is ready for your imagination — build a weekend getaway, future home, or simply enjoy your own slice of nature. Surrounded by beautiful mountain and wooded views, this peaceful lot offers the perfect retreat while still being just a short drive to downtown Winchester. New construction is happening throughout

Chris Roszko Colony Realty

0 Lot 50 Cardinal Dr, Winchester, VA 22602

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