Winchester, VA Homes

/51
$499,900
- 3 Beds
- 3 Baths
- 1,564 Sq Ft
510 S Cameron St, Winchester, VA 22601

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special.Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to

Brock Harris

Samson Properties

510 S Cameron St, Winchester, VA 22601
Explore Winchester
/74
Starting at $1,700 Plus Fees
- 1 - 4 Beds
230 Spring St, Winchester, VA 22601

Modern designs, elegant finishes, and the most desirable amenities await you at the area's newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

The Local

230 Spring St, Winchester, VA 22601
/4
$190,000

Sold Nov 25, 2025

303 Barrington Ln, Winchester, VA 22601
- 2 Beds
- 1 Bath
- 894 Sq Ft
- Built 1994
Last Sold Summary
- $213/SF
- 86 Days On Market
Current Estimated Value $203,777

Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

303 Barrington Ln, Winchester, VA 22601

/70
Est $698,572

Not Listed For Sale

113 Pangborne Ct, Winchester, VA 22602
- 4 Beds
- 4.5 Baths
- 4,395 Sq Ft
- Built 2018
113 Pangborne Ct, Winchester, VA 22602

Last Sold Summary
- 144 Days On Market
Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

/35
$329,999

$7K PRICE DROP Under Contract
- 3 Beds
- 4 Baths
- 1,320 Sq Ft
124 Worsham Terrace, Winchester, VA 22602

Welcome to this beautifully maintained townhouse that offers the perfect blend of comfort, style, and convenience. Boasting an attractive full brick-front exterior with classic black shutters, this home offers timeless curb appeal and a welcoming first impression. The private driveway, attached one-car garage, and well-maintained landscaping add both functionality and charm.The main

David Peña

Corcoran McEnearney

124 Worsham Terrace, Winchester, VA 22602
/8
$1,450 Per Month
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- Townhouse for Rent
2256 Roosevelt Blvd, Winchester, VA 22601

Very spacious 2-bedroom, 1-bathroom townhouse offering comfortable living in a well-maintained setting. Features include a rear entrance leading to a private porch area and convenient parking. Shared laundry facilities are located within the complex. Ideally situated near shopping, restaurants, and Shenandoah University. Tenant pays all utilities. No smoking, no pets, and no vaping permitted.

Frank Armstrong, IV

Colony Realty

2256 Roosevelt Blvd, Winchester, VA 22601
/51
$425,000

Sold Jun 10, 2026

104 Van Buren Place, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 1,714 Sq Ft
- Built 1990
Last Sold Summary
- 1% Above List Price
- $248/SF
- 6 Days On Market
Current Estimated Value $419,535

Last Listing Agent Leah Marabella Realty ONE Group Old Towne

104 Van Buren Place, Winchester, VA 22602

/74
Est $568,978

Not Listed For Sale

292 Fortress Dr, Winchester, VA 22603
- 5 Beds
- 3.5 Baths
- 3,360 Sq Ft
- Built 2009
292 Fortress Dr, Winchester, VA 22603

Last Sold Summary
- 4 Days On Market
Last Listing Agent Deborah Matthews ERA Oakcrest Realty, Inc.

/39
$399,000

$46K PRICE DROP Under Contract
- 6 Beds
- 3 Baths
- 1,917 Sq Ft
623 Smithfield Ave, Winchester, VA 22601

Spacious split-foyer home in the heart of Winchester featuring 6 bedrooms and 3 full bathrooms,. Well-maintained and located in a convenient neighborhood with no HOA.PRICE REDUCED TO SELL!

Carlos Soares

Samson Properties

623 Smithfield Ave, Winchester, VA 22601
/38
Starting at $1,712 Plus Fees
- 1 - 3 Beds
424 Ridgewood Ln, Winchester, VA 22601

Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

Denstock Meadow Branch LLC

424 Ridgewood Ln, Winchester, VA 22601
/57
$625,000

Sold Oct 31, 2025

101 Arthur Ln, Winchester, VA 22602
- 5 Beds
- 3.5 Baths
- 4,787 Sq Ft
- Built 2007
Last Sold Summary
- $131/SF
- 5 Days On Market
Current Estimated Value $653,576

Last Listing Agent Scotti Sellers Compass

101 Arthur Ln, Winchester, VA 22602

/46
Est $490,943

Not Listed For Sale

2876 Packer St, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,523 Sq Ft
- Built 2017
2876 Packer St, Winchester, VA 22601

Last Sold Summary
- 24 Days On Market
Last Listing Agent Kristina Towns Weichert Realtors - Blue Ribbon

/11
$1,499,000
- Land
- 2.45 Acres
- $611,837 per Acre
821,829,839, and 851 Fox Dr, Winchester, VA 22603

Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

Jim Shebest

Coldwell Banker Realty

821,829,839, and 851 Fox Dr, Winchester, VA 22603
/8
$1,600 Per Month
- 2 Beds
- 2 Baths
- 10,400 Sq Ft
- Condo for Rent
23 Taft Ave Unit 3, Winchester, VA 22601

One of the largest 2-bedroom, 2-bathroom apartments in Winchester! This spacious second-floor unit offers comfortable living in a convenient location close to shopping, restaurants, and Shenandoah University. The apartment features central air, a full-size washer and dryer, and a generous layout with plenty of living space. Step outside to enjoy a private porch, perfect for relaxing, sitting, or

Frank Armstrong, IV

Colony Realty

23 Taft Ave Unit 3, Winchester, VA 22601
/70
$535,000

Sold Jun 05, 2026

3691 Green Spring Rd, Winchester, VA 22603
- 4 Beds
- 2 Baths
- 1,612 Sq Ft
- Built 1970
Last Sold Summary
- 7% Above List Price
- $332/SF
- 1 Day On Market
Current Estimated Value $526,214

Last Listing Agent Bailey Cooper RE/MAX Gateway

3691 Green Spring Rd, Winchester, VA 22603

/34
Est $353,245

Not Listed For Sale

12 Montague Cir, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,530 Sq Ft
- Built 1971
12 Montague Cir, Winchester, VA 22601

Last Sold Summary
- 72 Days On Market
Last Listing Agent Jonathan Fleming Weichert Realtors - Blue Ribbon

/27
$439,000
- 3 Beds
- 2.5 Baths
- 1,711 Sq Ft
114 Meadow Way, Winchester, VA 22602

Discover the perfect blend of modern living and community charm in this stunning Colonial-style home located in the desirable High View Manor subdivision. Built in 2021, this meticulously maintained residence boasts an excellent condition, ensuring you can move in with peace of mind. The spacious layout is enhanced by thoughtful interior features, including ceiling fans for comfort and stylish

Lori Bales

Keller Williams Realty

114 Meadow Way, Winchester, VA 22602
/55
Starting at $1,667

Total Monthly Price
- 2 - 3 Beds
900-1024 N Braddock St, Winchester, VA 22601

Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home. Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

Fort Collier Terrace

900-1024 N Braddock St, Winchester, VA 22601
/20
$388,990

Sold Jul 29, 2026

110 Sioux Loop, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 6% Below List Price
- $206/SF
- 35 Days On Market
D.R. Horton Retreat at Winding Creek - Townhomes

110 Sioux Loop, Winchester, VA 22602

/33
Not Listed For Sale

566 N Loudoun St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 2,058 Sq Ft
- Built 1910
566 N Loudoun St, Winchester, VA 22601

Last Sold Summary
- 15 Days On Market
Last Listing Agent Dan Whitacre Colony Realty

/27
$359,900
- 3 Beds
- 2 Baths
- 1,743 Sq Ft
601 Gray Ave, Winchester, VA 22601

Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout.Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

Walther Vasquez Johnson

Samson Properties

601 Gray Ave, Winchester, VA 22601
/12
$1,500 Per Month
- 1 Bed
- 1 Bath
- 9,518 Sq Ft
- Condo for Rent
44 S Loudoun St Unit 7, Winchester, VA 22601

Historically charming one-bedroom apartment located on the famous downtown walking mall. Enjoy stylish living amongst shops, restaurants, museums, and parks. Only minutes to Winchester Medical Center, Shenandoah University and commuter routes

Brock Harris

Samson Properties

44 S Loudoun St Unit 7, Winchester, VA 22601
/15
$509,990

Sold Mar 11, 2026

108 Carnation Way, Winchester, VA 22603
- 3 Beds
- 2 Baths
- 2,050 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $249/SF
- 9 Days On Market
Brookfield Residential Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection

108 Carnation Way, Winchester, VA 22603

/87
Est $728,003

Not Listed For Sale

504 Old Fort Rd, Winchester, VA 22601
- 5 Beds
- 6 Baths
- 3,824 Sq Ft
- Built 2003
504 Old Fort Rd, Winchester, VA 22601

Last Sold Summary
- 74 Days On Market
Last Listing Agent Dallas Croft Samson Properties

/101
$879,900

Under Contract
- 5 Beds
- 4.5 Baths
- 3,898 Sq Ft
243 Summerfield Dr, Winchester, VA 22602

Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room with 20-foot ceilings, custom built-ins, a gas fireplace, and high windows featuring remote-controlled custom shades. The gourmet kitchen boasts granite countertops, soft-close cabinets, stainless steel appliances, double wall

Paul Gallagher

Colony Realty

243 Summerfield Dr, Winchester, VA 22602
/55
Starting at $1,222

Total Monthly Price
- 1 - 3 Beds
121 Fay St, Winchester, VA 22602

Live on your own terms with Fay Street Apartments. Find the comfort and convenience you crave among our one, two, and three-bedroom residences, on our well-kept premises, and in the nearby, city of Winchester, VA in the Shenandoah Valley. The property is conveniently located near top employers like Shenandoah University and Valley Health System. Our apartments open doors to a myriad of

Fay Street Apartments

121 Fay St, Winchester, VA 22602
/84
$618,000

Sold Jun 08, 2026

891 Payne Rd, Winchester, VA 22603
- 4 Beds
- 3.5 Baths
- 2,849 Sq Ft
- Built 1973
Last Sold Summary
- 12% Below List Price
- $217/SF
- 33 Days On Market
Current Estimated Value $638,103

Last Listing Agent Angela Duncan MarketPlace REALTY

891 Payne Rd, Winchester, VA 22603

/14
Est $233,905

Not Listed For Sale

223 Broad Ave, Winchester, VA 22602
- 3 Beds
- 1 Bath
- 868 Sq Ft
- Built 1959
223 Broad Ave, Winchester, VA 22602

Last Sold Summary
- 4 Days On Market
Last Listing Agent Stacey Mullins ERA Oakcrest Realty, Inc.

/43
$350,000

$10K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,230 Sq Ft
117 E Pall Mall St, Winchester, VA 22601

** Price improvement!** Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump

Becky Wallace

Pearson Smith Realty, LLC

117 E Pall Mall St, Winchester, VA 22601
/48
$2,200 Per Month
- 3 Beds
- 3 Baths
- 2,151 Sq Ft
- House for Rent
355 National Ave, Winchester, VA 22601

Available October 17 "Downtown Living" at 355 National Ave. 3 large bedrooms, 3 full bathrooms in the heart of Winchester City. Enjoy shops, bars, festivals, live music, farmers markets, breweries and restaurants a short walk from your spacious home with off street parking for 5+ cars and the convenience of a pull through driveway. With fenced yard and 3 outdoor covered porches, one of which is

Anna Fox

NextHome Realty Select

355 National Ave, Winchester, VA 22601
/11
$272,900

Sold Nov 13, 2025

852 Butler Ave, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,010 Sq Ft
- Built 1994
Last Sold Summary
- $270/SF
- 5 Days On Market
Current Estimated Value $295,417

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

852 Butler Ave, Winchester, VA 22601

/61
Est $639,585

Not Listed For Sale

215 Darby Dr, Winchester, VA 22602
- 4 Beds
- 4 Baths
- 3,262 Sq Ft
- Built 2004
215 Darby Dr, Winchester, VA 22602

Last Sold Summary
- 3 Days On Market
Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

/9
$689,000

$611K PRICE DROP
- Land
- 64.91 Acres
- $10,615 per Acre
Lot 7 Cedar Creek Grade, Winchester, VA

The seller has made a significant price adjustment to better align the property with current market conditions, creating an outstanding opportunity for buyers. With the new pricing, this property offers exceptional value and is positioned for serious consideration. If you've previously considered this property, now is the time to take another look. Rare opportunity to own 64+ scenic acres on the

Lori Bales

Keller Williams Realty

Lot 7 Cedar Creek Grade, Winchester, VA
/55
Starting at $1,685 Plus Fees
- 1 - 3 Beds
1981 Randolph Place, Winchester, VA 22601

Welcome to Stuart Hill Apartments — comfortable living in scenic Winchester, VA. Nestled in the picturesque Shenandoah Valley and just minutes from Historic Downtown Winchester, dining, shopping, Shenandoah University, and Winchester Medical Center, this well-maintained community offers spacious 1-, 2-, and 3-bedroom homes with full-size in-unit washers and dryers, generous closet space, and

Stuart Hill

1981 Randolph Place, Winchester, VA 22601
/42
$307,000

Sold Mar 26, 2026

140 Mccormick Cir Unit 302, Winchester, VA 22602
- 2 Beds
- 2 Baths
- 1,156 Sq Ft
- Built 2024
Last Sold Summary
- 3% Below List Price
- $266/SF
- 71 Days On Market
Last Listing Agent Karl Achstetter Keller Williams Realty

140 Mccormick Cir Unit 302, Winchester, VA 22602

/52
Est $579,537

Not Listed For Sale

224 Vine Ln, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 2,268 Sq Ft
- Built 1968
224 Vine Ln, Winchester, VA 22602

Last Sold Summary
- 28 Days On Market
Last Listing Agent Tracie Clawson ERA Oakcrest Realty, Inc.

/3
$339,000

$11K PRICE DROP
- Studio
- 1,654 Sq Ft
211, 213-215 E Clifford St, Winchester, VA 22601

Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath.The properties are deeded

Rhonda Shade

ERA Oakcrest Realty, Inc.

211, 213-215 E Clifford St, Winchester, VA 22601
/12
$1,900 Per Month
- 2 Beds
- 2 Baths
- 1,600 Sq Ft
- Condo for Rent
21 S Stewart St Unit 4, Winchester, VA 22601

Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

Frank Armstrong, IV

Colony Realty

21 S Stewart St Unit 4, Winchester, VA 22601
/69
$740,000

Sold Oct 29, 2025

170 Green Spring Rd, Winchester, VA 22603
- 4 Beds
- 4 Baths
- 2,740 Sq Ft
- Built 1999
Last Sold Summary
- $270/SF
- 13 Days On Market
Current Estimated Value $764,217

Last Listing Agent Kira Grubb Realty ONE Group Old Towne

170 Green Spring Rd, Winchester, VA 22603

/6
Est $391,920

Not Listed For Sale

110 Kingsland Ct, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 1,934 Sq Ft
- Built 1990
110 Kingsland Ct, Winchester, VA 22602

Last Sold Summary
- 0 Days On Market
Last Listing Agent Shane Bowman RE/MAX Roots

Showing Results 1 - 40, Page 1 of 18

Virginia Winchester County

Home Prices in Winchester, VA

The median home sale price in Winchester, VA is $415,000, up 2% year-over-year. Homes in Winchester sell in 45 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $415,000	Median Single Family Sale Price $449,945
Median Townhouse Sale Price $399,999	Median 2 Bedroom Sale Price $296,250
Median 1 Bedroom Sale Price $210,000	Average Price Per Sq Ft $205
Number of Homes for Sale 37,023	Last 12 months Home Sales 1,202
Months of Supply 4.00	Median List Price $430,000
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change 2%

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Winchester, VA Homes

Real Estate & Homes

Home Prices in Winchester, VA

Home Price Trends