Winchester County, VA Homes

/51
$419,000 Pending
- 4 Beds
- 2 Baths
- 2,408 Sq Ft
519 Whitacre St, Winchester, VA 22601

Ideally located within one of Winchester’s most desirable neighborhoods, Whittier Acres, and next to Winchester Medical Center, this spacious split-level home offers exceptional convenience paired with a rare sense of privacy in a quiet, established setting. Backing to mature trees, the backyard is a peaceful retreat where birds visit regularly and an established butterfly garden awaits its

Katie Landi Jordan Samson Properties

519 Whitacre St, Winchester, VA 22601
/17
$1,650 per month
- 2 Beds
- 1.5 Baths
- 1,100 Sq Ft
- Townhouse for Rent
26 B Jackson Ave, Winchester, VA 22601

Newly remodeled 2 bed 1.5 bath duplex unit in Winchester City! Fully fenced private backyard (fence currently being updated) and ample parking (4 spots per unit). New LVP flooring, stainless steel appliances and brand new in-unit laundry! Conveniently located near old towne Winchester, shopping, Rutherford Crossing, I81 and highway 7. Tour this charming, updated rental unit today!

Holly Graham Realty ONE Group Old Towne

26 B Jackson Ave, Winchester, VA 22601
/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 $533,641

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

2723 Windwood Dr, Winchester, VA 22601

/68
Est $402,286 Not Listed For Sale

3020 Papermill Rd, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 2,902 Sq Ft
- Built 1961
3020 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- 15% Above List Price
- $121/SF
- 68 Days On Market
Last Sold Price $349,900

Last Listing Agent Dave Spence RE/MAX

/25
$399,990 New Construction
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
201 Monteith Dr, Winchester, VA 22601

End Of Row Townhome With 1 Car Garage & Rear Deck! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end of row home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height, range

DRB Homes Builder

201 Monteith Dr, Winchester, VA 22601
/20

$1,457 - $1,835 per month

Peppertree VA

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.

221 Peppertree Ln, Winchester, VA 22601
/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 $558,764

Last Listing Agent Dave Spence RE/MAX Roots

2307 Stoneridge Rd, Winchester, VA 22601

/29
Est $319,594 Not Listed For Sale

3141 Papermill Rd, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,183 Sq Ft
- Built 1950
3141 Papermill Rd, Winchester, VA 22601

Last Sold Summary
- 5% Above List Price
- $258/SF
- 10 Days On Market
Last Sold Price $305,000

Last Listing Agent Dalton Stem LPT Realty, LLC

/17
$389,990 New Construction
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

***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*Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large

Brittany Newman DRB Group Realty, LLC

TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
/51
$3,100 per month
- 4 Beds
- 3.5 Baths
- 3,164 Sq Ft
- House for Rent
2013 Taylor Grace Ct, Winchester, VA 22601

**Beautiful Brick-Front Colonial for Rent – Spacious, Finished Walk-Up Basement, Fenced Yard** Well-maintained brick-front home located in an established neighborhood with convenient access to Downtown Winchester, Apple Blossom Mall, shopping, restaurants, parks, and commuter routes. Impressive curb appeal with a large driveway accommodating 4+ vehicles and an oversized 2-car garage featuring

John Ginty Samson Properties

2013 Taylor Grace Ct, Winchester, VA 22601
/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 $368,068

Last Listing Agent Dan Whitacre Colony Realty

520 N Loudoun St, Winchester, VA 22601

/20
Est $305,116 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
- 2% Above List Price
- $335/SF
- 11 Days On Market
Last Sold Price $300,000

Last Listing Agent Marcy Cantatore Atoka Properties | Middleburg Real Estate

/12
$80,000
- Land
- 0.13 Acre
- $615,385 per Acre
520 Highland Ave, Winchester, VA 22601

Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

Michael Sprague Samson Properties

520 Highland Ave, Winchester, VA 22601
/20

$1,525 - $2,010 per month

PEMBERTON

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

660 Pemberton Dr, Winchester, VA 22601
/50
$465,000 Sold Jul 10, 2025

350 Lanny Dr, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 2,371 Sq Ft
- Built 1967
Last Sold Summary
- $196/SF
- 22 Days On Market
Current Estimated Value $458,301

Last Listing Agent Sheila Pack RE/MAX Roots

350 Lanny Dr, Winchester, VA 22601

/37
Est $348,617 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
- 11% Above List Price
- $199/SF
- 11 Days On Market
Last Sold Price $315,000

Last Listing Agent Melissa Johnston ERA Oakcrest Realty, Inc.

/11
$80,000
- Land
- 0.08 Acre
- $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
/16
$1,500 per month
- 2 Beds
- 1 Bath
- 950 Sq Ft
- Townhouse for Rent
2 E Germain St, Winchester, VA 22601

Location! Walking distance from downtown walking mall and public transportation. 2 bedroom 1 bath apartment with hardwood flooring throughout living room and bedrooms. Property features a front porch, wash/dryer hookup and off street parking. Yard maintenance is included in rent. Requirements to qualify: 1) Minium annual household income $67K, 2) Good credit, and 3) Good landlord reference. $47

Courtney Spaid Crum Realty, Inc.

2 E Germain St, Winchester, VA 22601
/14
$460,000 Sold Aug 07, 2025

2620 Stonegate Dr, Winchester, VA 22601
- 5 Beds
- 3 Baths
- 2,974 Sq Ft
- Built 1995
Last Sold Summary
- $155/SF
- 10 Days On Market
Current Estimated Value $456,854

Last Listing Agent Anthony Adamovich Key Move Properties, LLC.

2620 Stonegate Dr, Winchester, VA 22601

/6
Est $305,568 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
- 11% Above List Price
- $273/SF
- 21 Days On Market
Last Sold Price $275,000

Last Listing Agent Brett Sowder RE/MAX

/2
$339,000 Coming Soon
- 3 Beds
- 1 Bath
- 1,699 Sq Ft
2956 Grace St, Winchester, VA 22601

Welcome to 2956 Grace Street — a 3-bedroom, 1-bath ranch-style home offering comfortable single-level living in Winchester, where a simple, functional layout and everyday ease come together. Inside, the home opens to a light-filled living area with hardwood floors that add warmth and character, creating a comfortable place to gather or unwind at the end of the day. The kitchen offers workspace

Carolyn Young Samson Properties

2956 Grace St, Winchester, VA 22601
/14
$2,200 per month
- 1 Bed
- 1 Bath
- 560 Sq Ft
- Condo for Rent
406 N Loudoun St Unit 1, Winchester, VA 22601

Property Id: 2365857 Cozy & Charming Downtown Apartment | Walkable | Full KitchenWelcome to your comfortable fully furnished home base in the heart of town! This bright, charming apartment blends classic architectural details with modern comfort—perfect for couples, solo travelers, or work trips.Step inside to find sun-filled living spaces, original trim and door frames

406 N Loudoun St Unit 1, Winchester, VA 22601
/2
$650,000 Sold Jul 10, 2025

19 E Boscawen St, Winchester, VA 22601
- 3 Beds
- 4 Baths
- 2,639 Sq Ft
- Built 1900
Last Sold Summary
- $246/SF
- 79 Days On Market
Current Estimated Value $499,546

Last Listing Agent Jen Moore ERA Oakcrest Realty, Inc.

19 E Boscawen St, Winchester, VA 22601

/24
Est $328,874 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
- 13% Above List Price
- $242/SF
- 5 Days On Market
Last Sold Price $290,000

Last Listing Agent Anna Fox NextHome Realty Select

/67
$375,000
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
707 E Cork St, Winchester, VA 22601

Make an offer! Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads,

Misty Weaver Samson Properties

707 E Cork St, Winchester, VA 22601
/11
$1,400 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
44 S Loudoun St Unit 9, Winchester, VA 22601

Charming 1 bedroom, 1 bathroom apartment located on the Historic Downtown walking mall, with access to all of the Shops, restaurants, museums, and more right out the front door! Just minutes from Shenandoah University, Apple Blossom Mall, and Winchester Medical Center. Parking for each unit.

Brock Harris Samson Properties

44 S Loudoun St Unit 9, Winchester, VA 22601
/38
$449,990 Sold Sep 18, 2025

1823 Reese Ct, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $238/SF
- 6 Days On Market
D.R. Horton Abrams Crossing at Meadow Branch

1823 Reese Ct, Winchester, VA 22601

/21
Est $326,031 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
- $318/SF
- 9 Days On Market
Last Sold Price $324,500

Last Listing Agent Heloisa Amar Samson Properties

/43
$429,000 Pending
- 3 Beds
- 2 Baths
- 2,648 Sq Ft
1332 Ramseur Ln, Winchester, VA 22601

Welcome home to this rare find in the desirable Mews of Meadow Branch—an exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. This well-maintained home is in excellent condition and features rich hardwood floors flowing throughout, creating a warm and inviting atmosphere. The spacious primary bedroom includes a cozy fireplace, perfect for relaxing evenings at home. The

James King RE/MAX Roots

1332 Ramseur Ln, Winchester, VA 22601
/73
$1,700 per month
- 1 Bed
- 1 Bath
- 650 Sq Ft
- Condo for Rent
342 Fairmont Ave Apt Unit Comfortable In-Towner, Winchester, VA 22601

COMPLETELY FURNISHED RENTAL.Perfect for traveling professionals or students or those renovating or selling a home and are in limbo until the new home is ready. Cozy and stylish one bedroom apartment in the heart of downtown, historic Winchester. This completely furnished apartment has everything you need for a short or extended stay. Linens, pots, pans, plates, glasses, utensils,

342 Fairmont Ave Apt Unit Comfortable In-Towner, Winchester, VA 22601
/34
$265,000 Sold Sep 09, 2025

2301 Tower Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 960 Sq Ft
- Built 1989
Last Sold Summary
- $276/SF
- 90 Days On Market
Current Estimated Value $265,476

Last Listing Agent Clint Pierpoint NextHome Realty Select

2301 Tower Ave, Winchester, VA 22601

/40
Est $297,233 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
- 16% Above List Price
- $302/SF
- 0 Days On Market
Last Sold Price $257,000

Last Listing Agent Kathrin Donovan Keller Williams Realty

/49
$675,000 Pending
- 5 Beds
- 3.5 Baths
- 3,294 Sq Ft
200 & 210 W Fairfax Ln, Winchester, VA 22601

Nestled in the heart of Winchester's cherished historic district, this enchanting circa 1928 cottage blends timeless charm with exceptional opportunity. Rich in character and architectural detail, the home showcases the craftsmanship of a bygone era - warm hardwood floors, inviting living spaces, and distinctive period touches that create an atmosphere both welcoming and refined. The home's

John Schroth Colony Realty

200 & 210 W Fairfax Ln, Winchester, VA 22601
/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

104 S Loudoun St Unit 2, Winchester, VA 22601
/29
$350,000 Sold Jul 09, 2025

1109 Opequon Ave, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1978
Last Sold Summary
- $292/SF
- 4 Days On Market
Current Estimated Value $345,611

Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

1109 Opequon Ave, Winchester, VA 22601

/25
Est $371,109 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
- 5% Below List Price
- $340/SF
- 39 Days On Market
Last Sold Price $389,999

Last Listing Agent Joelle Graham Weichert Corporate

/17
$339,900
- 3 Beds
- 1 Bath
- 960 Sq Ft
2952 Grace St, Winchester, VA 22601

Charming one level, 3-bedroom, 1 full bath home conveniently located in the heart of Winchester. Recently remodeled with new flooring throughout, updated bathroom, and modern fixtures. Thoughtful updates make this home move-in ready and ideal for easy, single-level living. Close to shopping, dining, and commuter routes.

Carolina Mosquera Weichert, REALTORS

2952 Grace St, Winchester, VA 22601
/17
$1,350 per month
- 1 Bed
- 1.5 Baths
- 900 Sq Ft
- Condo for Rent
25 W Boscawen St Unit 3, Winchester, VA 22601

Located in beautiful downtown Winchester!Unit comes with upgraded electronic code locks for easy, keyless entry. Unit has 2 large bedrooms, each with a private bathroom, living room and kitchen, with laundry in-unit! Can be configured as a 2 bedroom or a 1 bed with a large home office!

25 W Boscawen St Unit 3, Winchester, VA 22601
/48
$574,900 Sold Oct 17, 2025

1629 Pondview Dr, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,602 Sq Ft
- Built 1995
Last Sold Summary
- $221/SF
- 83 Days On Market
Current Estimated Value $575,724

Last Listing Agent Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

1629 Pondview Dr, Winchester, VA 22601

/22
Est $295,334 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
- 4% Above List Price
- $299/SF
- 25 Days On Market
Last Sold Price $285,000

Last Listing Agent Susan Wathen EXP Realty, LLC

Showing Results 161 - 200, Page 5 of 18

Virginia Winchester County

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Winchester County, VA Homes

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