Winchester County, VA Homes

/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
/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
/56
$545,000

Sold Nov 07, 2025

509 Marion St, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,691 Sq Ft
- Built 1992
Last Sold Summary
- $203/SF
- 3 Days On Market
Current Estimated Value $561,884

Last Listing Agent Mark Francis Real Broker LLC

509 Marion St, Winchester, VA 22601

/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

/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
/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
/2
$270,000

Sold Mar 20, 2026

407 van Fossen St, Winchester, VA 22601
- 2 Beds
- 1.5 Baths
- 954 Sq Ft
- Built 1956
Last Sold Summary
- 4% Below List Price
- $283/SF
- 7 Days On Market
Current Estimated Value $266,088

Last Listing Agent Michele Gibson Samson Properties

407 van Fossen St, Winchester, VA 22601

/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

/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
/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
/25
$215,000

Sold May 15, 2026

212 Shawnee Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 985 Sq Ft
- Built 1966
Last Sold Summary
- 14% Below List Price
- $218/SF
- 4 Days On Market
Current Estimated Value $244,521

Last Listing Agent Alexander Bracke Real Broker, LLC

212 Shawnee Ave, Winchester, VA 22601

/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
/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
/74
$340,000

Sold May 15, 2026

707 E Cork St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
- Built 1931
Last Sold Summary
- 7% Below List Price
- $202/SF
- 6 Days On Market
Current Estimated Value $345,454

Last Listing Agent Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

707 E Cork St, Winchester, VA 22601

/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

/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
/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
/29
$369,990

Sold Apr 28, 2026

213 Monteith Dr, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 3% Below List Price
- $207/SF
- 40 Days On Market
DRB Homes Village at Valor Crossing - Townhomes

213 Monteith Dr, Winchester, VA 22601

/34
Est $372,478

Not Listed For Sale

216 Monticello Square, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 2,436 Sq Ft
- Built 2010
216 Monticello Square, Winchester, VA 22602

Last Sold Summary
- 26 Days On Market
Last Listing Agent LESLIE WEBB Long & Foster Real Estate, 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
/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
/13
$275,000

Sold Jun 26, 2026

332 Opequon Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,404 Sq Ft
- Built 1979
Last Sold Summary
- 4% Below List Price
- $196/SF
- 24 Days On Market
Current Estimated Value $278,142

Last Listing Agent Renee Waymire Samson Properties

332 Opequon Ave, Winchester, VA 22601

/37
Est $431,170

Not Listed For Sale

222 E Piccadilly St, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 2,052 Sq Ft
- Built 2022
222 E Piccadilly St, Winchester, VA 22601

Last Sold Summary
- 595 Days On Market
Last Listing Agent Jason Aikens RE/MAX Roots

/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
/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
/25
$359,990

Sold Feb 17, 2026

230 Monteith Dr, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $202/SF
- 86 Days On Market
DRB Homes Village at Valor Crossing - Townhomes

230 Monteith Dr, Winchester, VA 22601

/20
Est $438,565

Not Listed For Sale

206 N Kent St, Winchester, VA 22601
- 2 Beds
- 4 Baths
- 2,160 Sq Ft
- Built 2022
206 N Kent St, Winchester, VA 22601

Last Sold Summary
- 0 Days On Market
Last Listing Agent Jason Aikens RE/MAX Roots

/41
$500,900
- 4 Beds
- 3 Baths
- 2,312 Sq Ft
609 Quartzite Cir, Winchester, VA 22601

Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides

Walther Vasquez Johnson

Samson Properties

609 Quartzite Cir, 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
/61
$580,000

Sold Dec 09, 2025

553 Bellview Ave, Winchester, VA 22601
- 5 Beds
- 2.5 Baths
- 2,386 Sq Ft
- Built 1978
Last Sold Summary
- $243/SF
- 2 Days On Market
Current Estimated Value $572,092

Last Listing Agent Dan Whitacre Colony Realty

553 Bellview Ave, Winchester, VA 22601

/45
Est $426,749

Not Listed For Sale

149 Biscane Ct, Winchester, VA 22602
- 3 Beds
- 3.5 Baths
- 2,250 Sq Ft
- Built 2018
149 Biscane Ct, Winchester, VA 22602

Last Sold Summary
- 3 Days On Market
Last Listing Agent Kara Koonce Weichert, REALTORS

/2
$175,000
- Land
- 16,117 Sq Ft
- $472,973 per Acre
719 Kennedy Dr, Winchester, VA 22601

Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

Frank Armstrong, IV

Colony Realty

719 Kennedy Dr, Winchester, VA 22601
/50
Starting at $1,862 Plus Fees
- 1 - 3 Beds
1864 Old Jube Square, Winchester, VA 22601

We've got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good

The Lofts at Jubal Square

1864 Old Jube Square, Winchester, VA 22601
/19
$275,000

Sold Jun 30, 2026

2956 Grace St, Winchester, VA 22601
- 4 Beds
- 1 Bath
- 1,699 Sq Ft
- Built 1950
Last Sold Summary
- 19% Below List Price
- $162/SF
- 57 Days On Market
Current Estimated Value $291,280

Last Listing Agent Carolyn Young Samson Properties

2956 Grace St, Winchester, VA 22601

/43
Est $376,830

Not Listed For Sale

230 Chestnut St, Winchester, VA 22601
- Studio
- 1,238 Sq Ft
- Built 1951
230 Chestnut St, Winchester, VA 22601

Last Sold Summary
- 4 Days On Market
Last Listing Agent Jeff Boppe Long & Foster Real Estate, Inc.

/37
$359,000
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
700 Green St, Winchester, VA 22601

You've been dreaming of main-level living, and this is IT! Check all your boxes:3 bedrooms2 full bathroomsOpen-concept family roomBeautifully updated kitchenSpacious kitchen islandPrimary suite with private bath, walk-in shower, and walk-in closetCharming front porch - perfect for morning coffee�� Roof replaced 2018Private back deckFenced

Jeanne Mezzatesta

Colony Realty

700 Green 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
/28
$309,000

Sold Aug 27, 2026

802 E Cork St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 1,996 Sq Ft
- Built 1930
Last Sold Summary
- 11% Below List Price
- $155/SF
- 87 Days On Market
Current Estimated Value $307,904

Last Listing Agent Jennifer Egen Samson Properties

802 E Cork St, Winchester, VA 22601

/36
Not Listed For Sale

912 S Braddock St, Winchester, VA 22601
- Studio
- 3,790 Sq Ft
- Built 1946
912 S Braddock St, Winchester, VA 22601

Last Sold Summary
- 42 Days On Market
Last Listing Agent Daniel Langberg Washington International Service Executives, LLC

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Winchester County, VA Homes

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