Winchester County, VA Homes

/11
$80,000
- Land
- 3,484 Sq Ft
- $1,000,000 per Acre
24 N Pleasant Valley Rd, Winchester, VA 22601

Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

Michael Sprague Samson Properties

24 N Pleasant Valley Rd, Winchester, VA 22601
/20
Starting at $1,150 Plus Fees
- 1 - 2 Beds
800 Thomas Ct, Winchester, VA 22601

Now Leasing: 1 & 2 Bedroom Apartments Available Now! In-unit washer and dryerWater and garbage includedEnjoy a serene, peaceful settingDon't miss out—these are first come, first serve!

North Winchester Apartments

(540) 546-5335

800 Thomas Ct, 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

/19
Est $436,119

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
- 49 Days On Market

/22
$269,000
- Land
- 42,253 Sq Ft
- $277,320 per Acre
823 Armistead St, Winchester, VA 22601

*** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

Janet Flaherty Keller Williams Realty

823 Armistead St, Winchester, VA 22601
/22
$2,225 Per Month
- 3 Beds
- 1.5 Baths
- 1,260 Sq Ft
- Townhouse for Rent
314 E Piccadilly St, Winchester, VA 22601

Freshly updated and just two blocks from the Old Town Pedestrian Mall — this charming downtown duplex is the perfect blend of historic character and modern comfort. Recently renovated, this 3-bedroom, 1.5-bath home features gleaming hardwood floors, beautifully updated tile bathrooms, stainless steel appliances, abundant natural light, and timeless architectural details throughout. Enjoy relaxing

Jeanne Mezzatesta

Colony Realty

(540) 507-2501

314 E Piccadilly St, Winchester, VA 22601
/43
$385,000

Sold Feb 13, 2026

420 Russelcroft Rd, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,580 Sq Ft
- Built 1996
Last Sold Summary
- 4% Below List Price
- $244/SF
- 26 Days On Market
Current Estimated Value $388,291

Last Listing Agent Brian Yoder Realty ONE Group Old Towne

420 Russelcroft Rd, 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
- 651 Days On Market

/40
$399,990

New Construction $15K PRICE DROP 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 Pearson Smith Realty, LLC

1821 Harvest Dr, Winchester, VA 22601
/20
Starting at $1,600 Plus Fees
- Studio - 2 Beds
114 N Loudoun St, Winchester, VA 22601

Brand new fully furnished extended stay apartments in the heart of Old Town Winchester Virginia including all utilities, washer /dyer, high speed internet, free nightly and weekend parking ( 5pm to 8 am), keyless entry, 10' ceilings, exposed brick interior partitions and optional weekly cleaning.. More information can be found at themerchantsuites

(540) 486-2842

114 N Loudoun St, Winchester, VA 22601
/9
$110,000

Sold Sep 08, 2025

116-118 W Leicester St, Winchester, VA 22601
- Land
- 5,227 Sq Ft
- $916,667 per Acre
Last Sold Summary
- 309 Days On Market
Current Estimated Value $97,500

Last Listing Agent Kim Hurst MarketPlace REALTY

116-118 W Leicester St, Winchester, VA 22601

/5
Not Listed For Sale

378 National Ave, Winchester, VA 22601
- Studio
- 3,032 Sq Ft
- Built 1910
378 National Ave, Winchester, VA 22601

Last Sold Summary
- 17 Days On Market

/13
$275,000

$10K PRICE DROP Pending
- 3 Beds
- 1 Bath
- 1,404 Sq Ft
332 Opequon Ave, Winchester, VA 22601

Adorable ranch home ready for new owners! The home has a large family room for entertainment, a rear patio for outside relaxation, and a fully fenced yard. Laminate flooring throughout the home with carpet in the family room. The price has been increased to reflect recent upgrades, including a fully remodeled bathroom, refinished kitchen cabinets, new countertops, fresh interior paint throughout

Renee Waymire Samson Properties

332 Opequon Ave, Winchester, VA 22601
/10
$1,700 Per Month
- 1 Bed
- 1 Bath
- 9,518 Sq Ft
- Condo for Rent
44 S Loudoun St Unit 12, 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 entertainment. This inviting apartment features a spacious living room, an updated kitchen with newer cabinets and stainless steel appliances, convenient in-unit laundry, and one assigned parking space in a private lot. Enjoy

Brock Harris

Samson Properties

(540) 413-0384

44 S Loudoun St Unit 12, Winchester, VA 22601
/32
$400,000

Sold Oct 09, 2025

225 Parkway St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 2,256 Sq Ft
- Built 1928
Last Sold Summary
- $177/SF
- 13 Days On Market
Current Estimated Value $396,356

Last Listing Agent Tracy Jewell Samson Properties

225 Parkway St, Winchester, VA 22601

/3
Not Listed For Sale

2902 Valley Ave, Winchester, VA 22601
2902 Valley Ave, Winchester, VA 22601

Last Sold Summary
- 238 Days On Market

/19
$319,900

$19K PRICE DROP Under Contract
- 4 Beds
- 1 Bath
- 1,699 Sq Ft
2956 Grace St, Winchester, VA 22601

**Brand new carpet and paint on main level** Welcome to 2956 Grace Street, this 3-bedroom 1-bath ranch-style home offers a functional layout designed for everyday living, paired with the added benefit of a fullt equipped guest suite. Whether you are accomodating extended family, hosting long-term guests or exploring rental potential, this home provides flexibility to fit a variety of

Carolyn Young Samson Properties

2956 Grace St, Winchester, VA 22601
/20
Starting at $1,685 Plus Fees
- 2 - 3 Beds
2250 Sofia Way, Winchester, VA 22601

Cedar Hill Apartments offers well-appointed accommodations located in a convenient and relaxing environment. Only minutes away from Route 37, Route 11, and Jubal Early Drive, Cedar Hill apartments offers its tenants easy access to the Winchester Medical Center, Shenandoah University, loads of shopping and restaurants. Interior features include vaulted ceilings, gas fireplace, wood vanity

CEDAR HILL APARTMENTS

(540) 502-3991

2250 Sofia Way, Winchester, VA 22601
/24
$370,000

Sold Nov 14, 2025

613 Laurelwood Cir, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- Built 2025
Last Sold Summary
- 35 Days On Market
Last Listing Agent Dev Patel Samson Properties

613 Laurelwood Cir, Winchester, VA 22601

/37
Est $416,860

Not Listed For Sale

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

Last Sold Summary
- 741 Days On Market

/37
$420,000

Under Contract
- 4 Beds
- 2 Baths
- 2,100 Sq Ft
17 E Leicester St, Winchester, VA 22601

OPEN HOUSE CANCELED.....UNDER CONTRACT....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

Roger Lamborne MarketPlace REALTY

17 E Leicester St, Winchester, VA 22601
/7
$1,600 Per Month
- 1 Bed
- 1 Bath
- 2,124 Sq Ft
- Condo for Rent
619 S Cameron St Unit 2, Winchester, VA 22601

Charming apartment located in 2 family unit, walking distance to Old Town Winchester. Original hardwood floors, light and bright unit with washer and dryer in unit. Landlord pays water and sewer and tenant pays electric. Shared yard.

Brock Harris

Samson Properties

(540) 584-8644

619 S Cameron St Unit 2, Winchester, VA 22601
/51
$725,000

Sold Mar 23, 2026

806 Mahone Dr, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,442 Sq Ft
- Built 1999
Last Sold Summary
- 2% Below List Price
- $297/SF
- 1 Day On Market
Current Estimated Value $725,264

Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.

806 Mahone Dr, Winchester, VA 22601

/22
Not Listed For Sale

3144 Eton Place, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,916 Sq Ft
- Built 2024
3144 Eton Place, Winchester, VA 22601

Last Sold Summary
- 9 Days On Market

/47
$339,900

$30K PRICE DROP Under Contract
- 3 Beds
- 1.5 Baths
- 1,366 Sq Ft
517 Dunlap St, Winchester, VA 22601

Welcome to 517 Dunlap St — a beautifully renovated 3-bedroom, 1.5-bath home set on a nicely sized, fully fenced lot in the heart of Winchester, where modern updates meet everyday comfort and a backyard designed for making the most of every season, complete with your own private pool.The main level welcomes you with a bright and inviting layout, where the living and dining spaces flow

Carolyn Young Samson Properties

517 Dunlap St, Winchester, VA 22601
/20
Starting at $1,525 Plus Fees
- 1 - 3 Beds
221 Peppertree Ln, Winchester, VA 22601

Tastefully designed 1, 2 and 3 bedroom floor plans and richly landscaped surroundings make for a welcome sight to call your home. Located in the heart of Winchester, Peppertree offers the conveniences of city living in a park-like setting. Peppertree is in close proximity to shopping, restaurants, schools and Winchester Medical Center.

Peppertree VA

(540) 502-4841

221 Peppertree Ln, Winchester, VA 22601
/35
$469,990

Sold Jan 07, 2026

1829 Harvest Dr, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 1,920 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 2% Below List Price
- $245/SF
- 4 Days On Market
D.R. Horton Abrams Crossing at Meadow Branch

1829 Harvest Dr, Winchester, VA 22601

/15
Not Listed For Sale

634 Hemsworth Ln, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,916 Sq Ft
- Built 2025
634 Hemsworth Ln, Winchester, VA 22601

Last Sold Summary
- 14 Days On Market

/33
$455,000

$5K PRICE INCREASE
- 3 Beds
- 2.5 Baths
- 1,440 Sq Ft
310 Longview Ave, Winchester, VA 22601

THIS IS A MUST SEE! Huge price reduction from motivated seller. OPEN HOUSE THIS SUNDAY.Amazing, location, 3 years new property, located in short drive to everything, Winchester. This is an offering you don't want to miss out on. Its not often that a nearly new construction home with all the best of everything comes on the market. For starters theres No HOA .All the appliances and operating

Dave Milburn Coldwell Banker Realty

310 Longview Ave, Winchester, VA 22601
/20
Starting at $1,535 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
/34
$585,000

Sold Aug 07, 2025

720 Beehive Way, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,571 Sq Ft
- Built 2006
Last Sold Summary
- $228/SF
- 53 Days On Market
Current Estimated Value $573,622

Last Listing Agent Amy Emerson-Kerns Beltway Realty, LLC.

720 Beehive Way, Winchester, VA 22601

/15
Not Listed For Sale

632 Hemsworth Ln, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 1,927 Sq Ft
- Built 2025
632 Hemsworth Ln, Winchester, VA 22601

Last Sold Summary
- 26 Days On Market

/51
$390,000

$10K PRICE DROP
- 5 Beds
- 2 Baths
- 1,011 Sq Ft
605 Dunlap St, Winchester, VA 22601

Priced to reflect the need for some updating, this home offers opportunities and personalization while remaining move-in ready 1011sf total living space.This home is in very good shape. The sellers are selling this property completely As-IS. NO HOA Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible

Alexandra Brown Spring Hill Real Estate, LLC.

605 Dunlap St, Winchester, VA 22601
/11
$1,498 Plus Fees
- 2 Beds
- 1.5 Baths
- 1,047 Sq Ft
- Condo for Rent
1105 Franklin St, Winchester, VA 22601

Welcome to your new home in the charming city of Winchester, VA! This delightful property is perfectly situated near a vibrant selection of restaurants and department stores, making it easy to enjoy local dining and shopping experiences. For outdoor enthusiasts, Jim Barnett Park is within walking distance, offering a serene escape for leisure activities. Plus, Valley Health is just a quick

(540) 573-2162

1105 Franklin St, Winchester, VA 22601
/43
$420,000

Sold Nov 14, 2025

2808 Saratoga Dr, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 2,018 Sq Ft
- Built 2002
Last Sold Summary
- $208/SF
- 24 Days On Market
Current Estimated Value $437,820

Last Listing Agent Dave Spence RE/MAX Roots

2808 Saratoga Dr, Winchester, VA 22601

/15
Not Listed For Sale

623 Hemsworth Ln, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 2,074 Sq Ft
- Built 2025
623 Hemsworth Ln, Winchester, VA 22601

Last Sold Summary
- 85 Days On Market

/13
$325,000

Under Contract
- 3 Beds
- 2 Baths
- 1,465 Sq Ft
632 Watson Ave, Winchester, VA 22601

* Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features granite countertops, new stainless steel appliances, and new vinyl plank flooring. The bathrooms includes new vanities, faucet, tub, shower and new vinyl

Jennifer Sacco RE/MAX Roots

632 Watson Ave, Winchester, VA 22601
/9
$1,495 Plus Fees
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Condo for Rent
2640 Valley Ave Unit 1, Winchester, VA 22601

Property Id: 2608151If interested, please call, we do not respond to email or requests. 1 Bedroom 1 Bath 600 sqft. $1395/Month 1 Year Lease. All Utilities Included. First and Security Due at Signing. Stove, dishwasher, fridge, washer, and dryer provided inside unit. Individual Unit Central heat and air. No Smoking. No Pets.. Meticulously maintained, serious inquiries ONLY!

(540) 534-0993

2640 Valley Ave Unit 1, Winchester, VA 22601
/60
$400,000

Sold Aug 26, 2025

319 Beechcroft Rd, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 2,538 Sq Ft
- Built 1961
Last Sold Summary
- $158/SF
- 4 Days On Market
Current Estimated Value $390,197

Last Listing Agent Gidget Smallwood Coldwell Banker Premier

319 Beechcroft Rd, Winchester, VA 22601

/17
Not Listed For Sale

621 Hemsworth Ln, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,451 Sq Ft
- Built 2025
621 Hemsworth Ln, Winchester, VA 22601

Last Sold Summary
- 48 Days On Market

Showing Results 81 - 120, Page 3 of 18

Virginia Winchester County

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Winchester County, VA Homes

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