Winchester County, VA Homes

/65
$389,990
- 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

Matthew Abregu

Keller Williams Realty

(540) 701-3590

317 Gray Ave, Winchester, VA 22601
/22
Starting at $1,495

Total Monthly Price
- 2 - 4 Beds
2260 Wilson Blvd, Winchester, VA 22601

Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

Blue Ridge Apartments

(844) 431-3204

2260 Wilson Blvd, Winchester, VA 22601
/22
$379,900 Sold Jul 10, 2025

1806 Kershaw Ln, Winchester, VA 22601
- 2 Beds
- 2 Baths
- 1,442 Sq Ft
- Built 2003
Last Sold Summary
- $263/SF
- 3 Days On Market
Current Estimated Value $384,643

Last Listing Agent Dan Whitacre Colony Realty

1806 Kershaw Ln, Winchester, VA 22601

/94
Est $896,378 Not Listed For Sale

102 S Stewart St, Winchester, VA 22601
- 7 Beds
- 3.5 Baths
- 5,049 Sq Ft
- Built 1900
102 S Stewart St, Winchester, VA 22601

Last Sold Summary
- 2% Above List Price
- $174/SF
- 11 Days On Market
- Last Sold Price $880,000
- Apr 30, 2025
Last Listing Agent John Scully Colony Realty

/20
$250,000
- 3 Beds
- 2 Baths
- 1,008 Sq Ft
514 Cather Ave, Winchester, VA 22601

Welcome to this home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers 3–4 bedroom options,

Paula Keiper

EXP Realty, LLC

(540) 452-9510

514 Cather Ave, Winchester, VA 22601
/14
$1,700 Per Month
- 1 Bed
- 1 Bath
- 9,518 Sq Ft
- Condo for Rent
44 S Loudoun St Unit 8, Winchester, VA 22601

Charming one-bedroom apartment in the heart of historic downtown Winchester! Located right on the Walking Mall, you’ll be surrounded by local shops, restaurants, and all the charm downtown living has to offer. This cozy apartment features a functional layout with plenty of storage space throughout. The bedroom includes an attached sunroom, perfect for a home office, reading nook, or extra lounge

Brock Harris

Samson Properties

(540) 505-0691

44 S Loudoun St Unit 8, Winchester, VA 22601
/68
$635,000 Sold Aug 01, 2025

800 Kennedy Dr, Winchester, VA 22601
- 5 Beds
- 4 Baths
- 2,639 Sq Ft
- Built 2009
Last Sold Summary
- $241/SF
- 22 Days On Market
Current Estimated Value $633,172

Last Listing Agent Cindy Greenya Keller Williams Realty

800 Kennedy Dr, Winchester, VA 22601

/53
Not Listed For Sale

525 N Cameron St, Winchester, VA 22601
- 5 Beds
- 2 Baths
- 1,694 Sq Ft
- Built 1920
525 N Cameron St, Winchester, VA 22601

Last Sold Summary
- $245/SF
- 24 Days On Market
- Last Sold Price $415,000
- Apr 25, 2025
Last Listing Agent Omni Casey Keller Williams Realty

/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

(540) 709-9357

719 Kennedy Dr, Winchester, VA 22601
/26
Starting at $1,272

Total Monthly Price
- 1 - 3 Beds
900-1024 N Braddock St, Winchester, VA 22601

Welcome to Fort Collier Terrace, an inviting community youll 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, youll find everything you need to feel right at home. Located near N Cameron Street and Martinsburg Pike, youre a stones throw away from the top dining,

Fort Collier Terrace

(540) 502-3449

900-1024 N Braddock St, Winchester, VA 22601
/47
$512,000 Sold Feb 27, 2026

216 Fairmont Ave, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 2,177 Sq Ft
- Built 1911
Last Sold Summary
- $235/SF
- 81 Days On Market
Current Estimated Value $515,512

Last Listing Agent Dave Spence RE/MAX Roots

216 Fairmont Ave, Winchester, VA 22601

/37
Est $441,236 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
- 9% Above List Price
- $197/SF
- 595 Days On Market
- Last Sold Price $404,900
- May 15, 2024
Last Listing Agent Jason Aikens RE/MAX

/22
$949,000 New Construction
- 4 Beds
- 3.5 Baths
- 2,546 Sq Ft
0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602

TO BE BUILT: Fauver and Browning Homes proudly presents The Tremont House—a masterfully designed modern residence that blurs the line between architecture and nature. Thoughtfully crafted to harmonize with its surroundings, this home offers a calm, refined living experience. Tucked at the end of a private cul-de-sac in desirable Fairway Estates, overlooking Winchester Country Club, the design

Jeanne Mezzatesta

Colony Realty

(540) 698-4119

0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602
/14
$2,200 Per Month
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
- Condo for Rent
104 S Loudoun St Unit 2, Winchester, VA 22601

Charming downtown living at it s best! Perfectly located directly on the Historic Downtown Walking Mall. This spacious 2 bedroom 2 bathroom condo features very own washer and dryer, stainless steel appliances, 2 assigned parking spots, HVAC and more. Shops, restaurants, museums, and more only steps from your front door. Check out convenient chic living today!

Brock Harris

Samson Properties

(540) 596-5993

104 S Loudoun St Unit 2, Winchester, VA 22601
/18
$330,000 Sold Jul 28, 2025

411 N Loudoun St Unit 104, Winchester, VA 22601
- 2 Beds
- 1.5 Baths
- 1,202 Sq Ft
- Built 1830
Last Sold Summary
- $275/SF
- 0 Days On Market
Last Listing Agent Lori Bales Keller Williams Realty

411 N Loudoun St Unit 104, Winchester, VA 22601

/20
Est $436,245 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
- 4% Below List Price
- $211/SF
- 0 Days On Market
- Last Sold Price $455,400
- Sep 29, 2023
Last Listing Agent Jason Aikens RE/MAX

/26
$349,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,784 Sq Ft
Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

OPEN HOUSE: Saturday - Sunday 12pm - 3pm Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' Trex deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

DRB Homes Builder

0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
/17
Starting at $500 Plus Fees
- 1 - 2 Beds
548 Brookfield Dr, Winchester, VA 22601

We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

Brookfield Corporate Apartments

(540) 546-5968

548 Brookfield Dr, Winchester, VA 22601
/2
$197,000 Sold May 15, 2025

414 Elm St, Winchester, VA 22601
- 2 Beds
- 1 Bath
- 915 Sq Ft
- Built 1960
Last Sold Summary
- $215/SF
- 1 Day On Market
Current Estimated Value $316,120

Last Listing Agent Aracely Rivera First Decision Realty LLC

414 Elm St, Winchester, VA 22601

/43
Est $391,732 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% Below List Price
- $330/SF
- 4 Days On Market
- Last Sold Price $409,000
- Jan 03, 2025
Last Listing Agent Jeff Boppe Long & Foster Real Estate, Inc.

/28
$369,990 Pending
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
213 Monteith Dr, Winchester, VA 22601

Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $12K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! Explore Winchester’s new luxury townhome

Brittany Newman DRB Group Realty, LLC

213 Monteith Dr, Winchester, VA 22601
/12
$1,350 Per Month
- 2 Beds
- 1 Bath
- 720 Sq Ft
- Townhouse for Rent
233 Kern St, Winchester, VA 22601

Downtown Winchester location, full of light and super cute! This 2 bed/1 bath duplex offers a private, fenced in backyard on the north side of town. Completely renovated in 2022. Available for immediate occupancy. Application fee $50 for everyone 18 or older, no pets, monthly income minimum of 3x the monthly rent, security deposit is $1350, no previous evictions, credit score 620+, no

Anna Fox

NextHome Realty Select

(540) 299-2935

233 Kern St, Winchester, VA 22601
/34
$412,000 Sold Jul 23, 2025

2320 Tower Ave, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 1,762 Sq Ft
- Built 2006
Last Sold Summary
- $234/SF
- 136 Days On Market
Current Estimated Value $393,018

Last Listing Agent Alex Adomako-Acheampong Samson Properties

2320 Tower Ave, 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
- $190/SF
- 42 Days On Market
- Last Sold Price $720,000
- Oct 26, 2023
Last Listing Agent Daniel Langberg Washington International Service Executives, LLC

/40
$349,000
- 4 Beds
- 2 Baths
- 1,996 Sq Ft
802 E Cork St, Winchester, VA 22601

Check out the Virtual Tour! Rich with character and steeped in history, this spacious vintage home sits proudly on a corner lot, offering timeless appeal with many original features still intact. From the moment you enter, you’ll appreciate the craftsmanship of a bygone era—complete with built-in bookshelves, a charming upper-level sleeping porch, and a traditional canning storage area in the

Jennifer Egen Samson Properties

802 E Cork St, Winchester, VA 22601
/6
Starting at $1,013 Plus Fees
- 1 - 3 Beds
570 N Cameron St, Winchester, VA 22601

Welcome to Zeropak Apartments at the heart of Winchester living. Located just steps from Old Town, Jim Barnett Park, cafes, events, and everyday essentials, Zeropak places you in one of Winchester's most connected and culturally rich neighborhoods. Rooted in the historic North End and surrounded by festivals, arts, and local flavor, this is where convenience meets character - and where community

ZeroPak Apartments

(540) 546-5767

570 N Cameron St, Winchester, VA 22601
/71
$1,025,000 Sold Aug 01, 2025

331 N Braddock St, Winchester, VA 22601
- 5 Beds
- 6 Baths
- 6,517 Sq Ft
- Built 1863
Last Sold Summary
- $157/SF
- 36 Days On Market
Last Listing Agent John Schroth Colony Realty

331 N Braddock St, Winchester, VA 22601

/49
Est $426,137 Not Listed For Sale

110 W Monmouth St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,728 Sq Ft
- Built 1900
110 W Monmouth St, Winchester, VA 22601

Last Sold Summary
- 5% Above List Price
- $234/SF
- 30 Days On Market
- Last Sold Price $405,000
- Jun 19, 2023
Last Listing Agent Angela Duncan MarketPlace REALTY

/47
$289,900 Pending
- 4 Beds
- 2.5 Baths
- 1,530 Sq Ft
2963 Sorrell Ct, Winchester, VA 22601

Location, location, location! Well-maintained 3-level townhome ideally situated for commuters with convenient access to Route 7 and I-81, and close proximity to shopping, dining, and schools. Ample parking available in both the front and rear of the home.This home features 4 bedrooms, 2 full baths, and 1 half bath with a convenient main-level entry. The kitchen was remodeled in 2020 and

Renzo Falla RE/MAX Real Estate Connections

2963 Sorrell Ct, 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

(540) 329-2681

23 Taft Ave Unit 3, Winchester, VA 22601
/43
$410,000 Sold Apr 20, 2026

1332 Ramseur Ln, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 2,648 Sq Ft
- Built 1994
Last Sold Summary
- 4% Below List Price
- $155/SF
- 16 Days On Market
Current Estimated Value $467,815

Last Listing Agent James King RE/MAX Roots

1332 Ramseur Ln, Winchester, VA 22601

/2
Est $263,818 Not Listed For Sale

127 S Euclid Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
- Built 1920
127 S Euclid Ave, Winchester, VA 22601

Last Sold Summary
- 39% Above List Price
- $170/SF
- 3 Days On Market
- Last Sold Price $190,000
- Jul 15, 2024
Last Listing Agent Carolina Mosquera Weichert Corporate

/40
$399,990 Pending
- 4 Beds
- 3.5 Baths
- 1,920 Sq Ft
1821 Harvest Dr, Winchester, VA 22601

1821 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA – ready to move in! Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, soft-close grey cabinets & drawers, and

Brooks Sears D R Horton Realty of Virginia LLC

1821 Harvest Dr, Winchester, VA 22601
/20
Starting at $1,575 Plus Fees
- 2 - 3 Beds
660 Pemberton Dr, Winchester, VA 22601

Pemberton Village Apartments in Winchester VA is located in the prestigious Meadow Branch subdivision near the intersection of Jubal Early Drive and Harvest Drive. It is a ten building, 120 unit community easily assessable from Interstate 81 or Route 37. Conveniently located near the Apple Blossom Mall, fitness centers, John Handley High School, and Valley Health Medical Center; Pemberton Village

PEMBERTON

(540) 502-4138

660 Pemberton Dr, Winchester, VA 22601
/60
$529,000 Sold Dec 04, 2025

121 N Washington St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 3,100 Sq Ft
- Built 1807
Last Sold Summary
- $171/SF
- 69 Days On Market
Current Estimated Value $524,170

Last Listing Agent M. Kelly Walker RE/MAX Roots

121 N Washington St, Winchester, VA 22601

/19
Est $434,950 Not Listed For Sale

204 N Kent St, Winchester, VA 22601
- 2 Beds
- 4 Baths
- 2,052 Sq Ft
- Built 2022
204 N Kent St, Winchester, VA 22601

Last Sold Summary
- 3% Above List Price
- $206/SF
- 49 Days On Market
- Last Sold Price $423,345
- Sep 20, 2023
Last Listing Agent Jason Aikens RE/MAX

/37
$420,000
- 4 Beds
- 2 Baths
- 2,100 Sq Ft
17 E Leicester St, Winchester, VA 22601

The perfect old town Winchester location and ready for you to move in......Classic brick “American Foursquare” house in Winchester’s historic district. . This well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front

Roger Lamborne MarketPlace REALTY

17 E Leicester St, Winchester, VA 22601
/12
$1,600 Per Month
- 2 Beds
- 1 Bath
- 1,300 Sq Ft
- House for Rent
228 Opequon Ave, Winchester, VA 22601

coming soon- pictures will be up later today

Frank Armstrong, IV

Colony Realty

(540) 766-5892

228 Opequon Ave, Winchester, VA 22601
/49
$675,000 Sold Apr 20, 2026

200 & 210 W Fairfax Ln, Winchester, VA 22601
- 5 Beds
- 3.5 Baths
- 3,294 Sq Ft
- Built 1928
Last Sold Summary
- $205/SF
- 3 Days On Market
Last Listing Agent John Schroth Colony Realty

200 & 210 W Fairfax Ln, Winchester, VA 22601

/37
Not Listed For Sale

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

Last Sold Summary
- $199/SF
- 651 Days On Market
- Last Sold Price $409,000
- Jun 14, 2024
Last Listing Agent Jason Aikens RE/MAX

Showing Results 41 - 80, Page 2 of 18

Virginia Winchester County

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Winchester County, VA Homes

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