Winchester, VA Homes

/17
$289,000
- 3 Beds
- 1 Bath
- 1,338 Sq Ft
980 Greenwood Rd, Winchester, VA 22602

Perfectly positioned on the east side of town, this home is just minutes from local shopping, excellent schools, and major commuter routes. Inside, you’re welcomed by hardwood floors that flow throughout the living room and bedrooms. The cabinet-packed kitchen overlooks a cozy dining area and provides access to a bright four-season room — the perfect spot for morning coffee or relaxing before

Brock Harris

Samson Properties

(540) 792-3667

980 Greenwood Rd, Winchester, VA 22602
/40
Starting at $1,522

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

(540) 508-8339

121 Fay St, Winchester, VA 22602
/56
$612,225

Sold Mar 25, 2026

119 Hydrangea Way, Winchester, VA 22602
- 4 Beds
- 3 Baths
- 2,865 Sq Ft
- Built 2025
Last Sold Summary
- $214/SF
- 210 Days On Market
Last Listing Agent Brooks Sears Pearson Smith Realty, LLC

119 Hydrangea Way, Winchester, VA 22602

/70
Est $611,834

Not Listed For Sale

104 Quigley Ct, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 3,078 Sq Ft
- Built 2004
104 Quigley Ct, Winchester, VA 22602

Last Sold Summary
- 0 Days On Market

/45
$89,500

$21K PRICE DROP
- 3 Beds
- 2 Baths
- 1,495 Sq Ft
135 Gregory Place, Winchester, VA 22603

This 2018-built manufactured ranch-style home is move-in ready and well maintained for its new owner. The home offers an open floor plan featuring a spacious kitchen with abundant countertop space, a large pantry, and a dining area that flows into the main living space. The living room provides plenty of open space for comfortable everyday living, and the home also includes a dedicated laundry

Diego Abregu

Keller Williams Realty

(540) 329-2535

135 Gregory Place, Winchester, VA 22603
/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

(540) 516-4753

44 S Loudoun St Unit 9, Winchester, VA 22601
/57
$630,000

Sold Jul 03, 2025

716 S Washington St, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,774 Sq Ft
- Built 1865
Last Sold Summary
- $227/SF
- 28 Days On Market
Current Estimated Value $624,976

Last Listing Agent Lisa Alberti Pearson Smith Realty, LLC

716 S Washington St, Winchester, VA 22601

/45
Est $380,208

Not Listed For Sale

200 Dogwood Rd, Winchester, VA 22602
- 3 Beds
- 1.5 Baths
- 1,104 Sq Ft
- Built 1967
200 Dogwood Rd, Winchester, VA 22602

Last Sold Summary
- 5 Days On Market

/3
$429,000

$16K PRICE DROP
- 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.

Carlos Soares

Samson Properties

(540) 253-3199

623 Smithfield Ave, Winchester, VA 22601
/40
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 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

(540) 502-3449

900-1024 N Braddock St, Winchester, VA 22601
/65
$670,000

Sold Feb 03, 2026

521 Hidden Valley Ln, Winchester, VA 22603
- 3 Beds
- 4 Baths
- 2,973 Sq Ft
- Built 2001
Last Sold Summary
- 2% Above List Price
- $225/SF
- 10 Days On Market
Current Estimated Value $656,409

Last Listing Agent Kaitlyn Behr Samson Properties

521 Hidden Valley Ln, Winchester, VA 22603

/13
Est $344,422

Not Listed For Sale

107 Cardinal Ln, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,160 Sq Ft
- Built 1967
107 Cardinal Ln, Winchester, VA 22602

Last Sold Summary
- 4 Days On Market

/7
$369,000

Coming Soon
- 3 Beds
- 2.5 Baths
- 1,737 Sq Ft
614 Sherlock Trace, Winchester, VA 22601

**Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home

Carlos Soares

Samson Properties

(540) 517-6899

614 Sherlock Trace, 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

(540) 386-1044

2256 Roosevelt Blvd, Winchester, VA 22601
/67
$620,000

Sold Aug 07, 2025

162 Darby Dr, Winchester, VA 22602
- 4 Beds
- 4 Baths
- 2,760 Sq Ft
- Built 2002
Last Sold Summary
- $225/SF
- 19 Days On Market
Current Estimated Value $637,261

Last Listing Agent Michael Elias Century 21 Redwood Realty

162 Darby Dr, Winchester, VA 22602

/40
Est $288,030

Not Listed For Sale

123 Pingley Ln, Winchester, VA 22602
- 2 Beds
- 1 Bath
- 1,276 Sq Ft
- Built 1920
123 Pingley Ln, Winchester, VA 22602

Last Sold Summary
- 246 Days On Market

/30
$280,000

$15K PRICE DROP Under Contract
- 2 Beds
- 2 Baths
- 864 Sq Ft
704 Watson Ave, Winchester, VA 22601

Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for

Carlos Soares

Samson Properties

(540) 530-4023

704 Watson Ave, Winchester, VA 22601
/22
Starting at $1,420

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
/38
$621,490

Sold Nov 18, 2025

123 Hydrangea Way, Winchester, VA 22602
- 4 Beds
- 3 Baths
- 1,748 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $356/SF
- 19 Days On Market
D.R. Horton Willow Run

123 Hydrangea Way, Winchester, VA 22602

/47
Est $366,881

Not Listed For Sale

312 Bryarly Rd, Winchester, VA 22603
- 3 Beds
- 2 Baths
- 2,730 Sq Ft
- Built 1966
312 Bryarly Rd, Winchester, VA 22603

Last Sold Summary
- 9 Days On Market

/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

(540) 530-3068

821,829,839, and 851 Fox Dr, Winchester, VA 22603
/14
$1,250 Per Month
- 1 Bed
- 1 Bath
- 750 Sq Ft
- House for Rent
448 N Loudoun St Unit C, Winchester, VA 22601

UTILITIES INCLUDED IN RENT. Water, sewer, trash and electric included. This 1 bed, 1 bath apartment features hardwood floors, in unit laundry, and historic charm. Located 4 blocks North of the Walking Mall in Downtown Winchester. The unit is on the 2nd floor, with the bedroom on the 3rd floor. Windows overlook N Loudoun St and offer loads of natural light on the main level. $50 application fee

Anna Fox

NextHome Realty Select

(540) 517-6815

448 N Loudoun St Unit C, 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 $548,333

Last Listing Agent Mark Francis Real Broker LLC

509 Marion St, Winchester, VA 22601

/32
Est $393,139

Not Listed For Sale

320 Adams Rd, Winchester, VA 22603
- 1 Bed
- 1 Bath
- 648 Sq Ft
- Built 2000
320 Adams Rd, Winchester, VA 22603

Last Sold Summary
- 45 Days On Market

/28
$349,900

Under Contract
- 3 Beds
- 1.5 Baths
- 1,890 Sq Ft
113 Christopher Dr, Winchester, VA 22601

Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 318-0527

113 Christopher Dr, Winchester, VA 22601
/4
$2,350

Total Monthly Price
- 4 Beds
- 3.5 Baths
- 1,920 Sq Ft
- Townhouse for Rent
501 Emily Ln, Winchester, VA 22602

For Rent – Winchester, VABeautiful home featuring 4 bedrooms and 3.5 bathrooms with approximately 1,920 sqft of living space. Offers spacious areas, great natural light, and a functional layout for everyday comfort.Located in a quiet neighborhood with easy access to shopping, dining, and major roads.

(540) 609-2918

501 Emily Ln, Winchester, VA 22602
/17
$256,000

Sold Apr 29, 2026

136 Parkside Dr, Winchester, VA 22602
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 1989
Last Sold Summary
- $229/SF
- 3 Days On Market
Current Estimated Value $253,640

Last Listing Agent Nancy Tessman EXP Realty, LLC

136 Parkside Dr, Winchester, VA 22602

/65
Est $397,066

Not Listed For Sale

205 Cobble Stone Dr, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 2,263 Sq Ft
- Built 2014
205 Cobble Stone Dr, Winchester, VA 22602

Last Sold Summary
- 6 Days On Market

/27
$330,000

Under Contract
- 3 Beds
- 4 Baths
- 1,920 Sq Ft
111 Ridge Ct, Winchester, VA 22603

Beautifully renovated townhome ideally located near the highly convenient Rt. 522N and Rt. 37 interchange, just minutes from Shenandoah University while tucked away in a quiet, small-townhome community.Brand new HVAC system! Step inside to discover a modern interior featuring luxury vinyl plank flooring throughout and stylishly remodeled bathrooms. The spacious kitchen is designed to impress

Lori Bales

Keller Williams Realty

(540) 572-7575

111 Ridge Ct, Winchester, VA 22603
/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
/26
$235,000

Sold Jun 16, 2025

164 Brookland Ct Unit 10, Winchester, VA 22602
- 2 Beds
- 2 Baths
- 1,173 Sq Ft
- Built 2003
Last Sold Summary
- $200/SF
- 14 Days On Market
Current Estimated Value $241,554

Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

164 Brookland Ct Unit 10, Winchester, VA 22602

/37
Est $427,192

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

/11
$61,900
- Land
- 30,056 Sq Ft
- $89,710 per Acre
Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602

Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 712-6303

Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602
/33
Starting at $1,550 Plus Fees
- 1 - 2 Beds
110 Bulmer Loop, Winchester, VA 22602

Our community is perfect for those who enjoy spending time outside living a healthy, lively lifestyle by using the walking trails, outdoor common areas, and dog park, as well as for those who appreciate a home that is a retreat from the business of everyday life. We are conveniently located a few short miles from Shenandoah University, I-81, Rt. 8 and Rt. 50 in Winchester, VA. Our apartments

Madison Village Apartments (Winchester)

(540) 306-5683

110 Bulmer Loop, Winchester, VA 22602
/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 $267,880

Last Listing Agent Michele Gibson Samson Properties

407 van Fossen St, Winchester, VA 22601

/14
Not Listed For Sale

0 Susquehanna Trail, Winchester, VA 22602
0 Susquehanna Trail, Winchester, VA 22602

Last Sold Summary
- 19 Days On Market

/23
$375,000
- 4 Beds
- 3 Baths
- 1,916 Sq Ft
317 N Kent St, Winchester, VA 22601

Step into a world of timeless elegance and modern luxury with this stunning Colonial residence, beautifully renovated in 2015 while preserving its historic charm. Nestled in a serene setting, this detached home offers a perfect blend of classic architecture and contemporary comforts, making it an ideal retreat for those seeking an exclusive lifestyle. As you enter, you are greeted by rich

Clark Smith

Samson Properties

(540) 530-4200

317 N Kent St, 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

(540) 596-5993

104 S Loudoun St Unit 2, Winchester, VA 22601
/61
$770,000

Sold Feb 25, 2026

162 Janes Way, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 4,461 Sq Ft
- Built 2001
Last Sold Summary
- $173/SF
- 77 Days On Market
Current Estimated Value $773,796

Last Listing Agent Tanner Pack RE/MAX Roots

162 Janes Way, Winchester, VA 22602

/20
Est $443,377

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

Showing Results 41 - 80, Page 2 of 18

Virginia Winchester County Winchester

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Winchester, VA Homes

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