Winchester County, VA Homes

/32
$449,000
- 4 Beds
- 4.5 Baths
- 1,913 Sq Ft
315 National Ave, Winchester, VA 22601

Fully reimagined for modern living while preserving its timeless charm, this stunning 1910 home in the heart of Downtown Winchester offers the perfect blend of character, luxury, and value. Completely renovated from top to bottom, every detail has been thoughtfully updated—delivering the feel of new construction within a classic architectural setting.This spacious residence features 4

Carlos Soares

Samson Properties

(540) 787-2197

315 National Ave, Winchester, VA 22601
/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

(434) 443-7642

230 Spring St, 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

/80
Est $441,402

Not Listed For Sale

2820 Baldwin St, Winchester, VA 22601
- 5 Beds
- 3 Baths
- 3,128 Sq Ft
- Built 1965
2820 Baldwin St, Winchester, VA 22601

Last Sold Summary
- 9 Days On Market

/30
$326,000

$1K PRICE INCREASE Under Contract
- 4 Beds
- 2 Baths
- 1,273 Sq Ft
629 National Ave, Winchester, VA 22601

Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island

Walther Vasquez Johnson

Samson Properties

(540) 889-0898

629 National Ave, Winchester, VA 22601
/13
$1,500 Per Month
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- House for Rent
21 S Stewart St Unit 2, Winchester, VA 22601

2 Bedroom Apartment for Rent – Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or

Frank Armstrong, IV

Colony Realty

(540) 534-4239

21 S Stewart St Unit 2, 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

/39
Est $533,783

Not Listed For Sale

2938 S Pleasant Valley Rd, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,376 Sq Ft
- Built 1960
2938 S Pleasant Valley Rd, Winchester, VA 22601

Last Sold Summary
- 3 Days On Market

/24
$255,000

$10K PRICE DROP Under Contract
- 2 Beds
- 1.5 Baths
- 1,068 Sq Ft
103 E Germain St, Winchester, VA 22601

Welcome home to 103 E Germain St, a rare end-of-row townhouse combining the historic elegance of downtown Winchester with the modern ease of late-80s construction. Whether you are a first-time buyer looking for a move-in ready home or a savvy investor looking for a high-demand rental with excellent yield potential, this property ticks every single box. Flooded with natural light, the main level

Jodi Cilley

Realty ONE Group Old Towne

(540) 924-1926

103 E Germain St, Winchester, VA 22601
/38
Starting at $1,837 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

(540) 502-3204

424 Ridgewood Ln, 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 $267,880

Last Listing Agent Michele Gibson Samson Properties

407 van Fossen St, Winchester, VA 22601

/31
Est $328,653

Not Listed For Sale

2617 Cornerstone Cir, Winchester, VA 22601
- 2 Beds
- 1.5 Baths
- 1,012 Sq Ft
- Built 1997
2617 Cornerstone Cir, Winchester, VA 22601

Last Sold Summary
- 55 Days On Market

/65
$379,900

$10K PRICE DROP Under Contract
- 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
/8
$1,600 Per Month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
619 S Cameron St Unit 1, 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) 235-5717

619 S Cameron St Unit 1, Winchester, VA 22601
/48
$335,200

Sold Jul 25, 2025

128 Fox Dr, Winchester, VA 22601
- 4 Beds
- 3 Baths
- 2,606 Sq Ft
- Built 1961
Last Sold Summary
- $129/SF
- 25 Days On Market
Current Estimated Value $337,702

Last Listing Agent MJ Frazier Serhant

128 Fox Dr, Winchester, VA 22601

/60
Est $570,972

Not Listed For Sale

2411 Windwood Dr, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,564 Sq Ft
- Built 2002
2411 Windwood Dr, Winchester, VA 22601

Last Sold Summary
- 2 Days On Market

/13
$274,999
- 2 Beds
- 2.5 Baths
- 1,080 Sq Ft
206 Kimberly Way, Winchester, VA 22601

Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and

Frank Armstrong, IV

Colony Realty

(540) 516-5187

206 Kimberly Way, Winchester, VA 22601
/46
Starting at $1,745 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

(540) 546-6430

1981 Randolph Place, 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 $296,548

Last Listing Agent Alexander Bracke Real Broker, LLC

212 Shawnee Ave, Winchester, VA 22601

/38
Est $323,432

Not Listed For Sale

111 Montague Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,172 Sq Ft
- Built 1955
111 Montague Ave, Winchester, VA 22601

Last Sold Summary
- 3 Days On Market

/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
/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
/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 $361,812

Last Listing Agent Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

707 E Cork St, Winchester, VA 22601

/67
Est $486,561

Not Listed For Sale

435 Mosby St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 1,604 Sq Ft
- Built 1956
435 Mosby St, Winchester, VA 22601

Last Sold Summary
- 0 Days On Market

/2
$337,000

Coming Soon
- 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 living level

David Peña

Corcoran McEnearney

(540) 730-1775

124 Worsham Terrace, Winchester, VA 22602
/50
Starting at $1,875 Plus Fees
- 1 - 2 Beds
2351 Quinn Ct, Winchester, VA 22601

This new mixed-use community is centrally located in Winchester with quick access to Routes 522 and I-81. Designed for modern, convenient living, Carl's Corner features three residential buildings and a standalone commercial complex.The community offers 18 one-bedroom and 60 two-bedroom apartments, all within walking distance of shopping centers and just minutes from restaurants and

CARLS CORNER RESIDENTIAL

(540) 773-2474

2351 Quinn Ct, 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

/37
Est $287,505

Not Listed For Sale

353 Shawnee Ave, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
- Built 1983
353 Shawnee Ave, Winchester, VA 22601

Last Sold Summary
- 24 Days On Market

/3
$425,000

$20K 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
/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
/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

/69
Est $493,518

Not Listed For Sale

256 Parkway St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 2,028 Sq Ft
- Built 1940
256 Parkway St, Winchester, VA 22601

Last Sold Summary
- 3 Days On Market

/7
$369,000
- 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
/50
Starting at $1,863 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

(540) 837-6802

1864 Old Jube Square, 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 $574,203

Last Listing Agent Dan Whitacre Colony Realty

553 Bellview Ave, Winchester, VA 22601

/28
Est $421,206

Not Listed For Sale

1203 Valley Ave, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 2,001 Sq Ft
- Built 1920
1203 Valley Ave, Winchester, VA 22601

Last Sold Summary

/4
$289,900

Coming Soon
- 2 Beds
- 1 Bath
- 1,458 Sq Ft
102 N Purcell Ave, Winchester, VA 22601

Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 565-5107

102 N Purcell Ave, 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
/73
$497,000

Sold Aug 25, 2025

903 Crestview Terrace, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 3,204 Sq Ft
- Built 2006
Last Sold Summary
- $155/SF
- 64 Days On Market
Current Estimated Value $558,508

Last Listing Agent MARIA STRIBLING CENTURY 21 New Millennium

903 Crestview Terrace, Winchester, VA 22601

/47
Est $379,846

Not Listed For Sale

675 National Ave, Winchester, VA 22601
- 4 Beds
- 1.5 Baths
- 1,824 Sq Ft
- Built 1941
675 National Ave, Winchester, VA 22601

Last Sold Summary
- 22 Days On Market

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Virginia Winchester County

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