Winchester, VA Homes

/54
$610,000

$20K PRICE DROP
- 4 Beds
- 3.5 Baths
- 4,120 Sq Ft
211 Flanagan Dr, Winchester, VA 22602

Pictures coming soon. Prime Location in Raven Wing!This beautiful Colonial home offers the perfect combination of comfort, convenience, and modern updates. Located in the desirable Raven Wing community, you'll enjoy easy access to schools, shopping, restaurants, and commuter routes.Recent improvements include a new roof (2025), hot water heater (3 years old), sump pump (1.5 years old),

Ned Stock

Berkshire Hathaway HomeServices PenFed Realty

211 Flanagan Dr, Winchester, VA 22602
/50
Starting at $1,862 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

1864 Old Jube Square, 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 $685,780

Last Listing Agent Kaitlyn Behr Samson Properties

521 Hidden Valley Ln, Winchester, VA 22603

/36
Est $408,279

Not Listed For Sale

100 Candlewick Dr, Winchester, VA 22602
- 2 Beds
- 2 Baths
- 1,664 Sq Ft
- Built 2001
100 Candlewick Dr, Winchester, VA 22602

Last Sold Summary
- 42 Days On Market
Last Listing Agent Mark Francis ICON Real Estate, LLC

/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

719 Kennedy Dr, Winchester, VA 22601
/22
$1,800 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

Jeanne Mezzatesta

Colony Realty

314 E Piccadilly St, 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

/46
Est $418,253

Not Listed For Sale

133 Woodrow Rd, Winchester, VA 22602
- 3 Beds
- 3 Baths
- 1,806 Sq Ft
- Built 1998
133 Woodrow Rd, Winchester, VA 22602

Last Sold Summary
- 51 Days On Market
Last Listing Agent Angie Ordonez NextHome Realty Select

/17
$125,000
- 1 Bed
- 1 Bath
- 624 Sq Ft
415 Puma Trail, Winchester, VA 22602

Ranch cabin-style home nestled in the woods on a private 1⁄2-acre lot. Featuring 1-bedroom, additional room but not technically a bedroom, and 1 full bath, this property offers endless potential as a full-time residence, weekend retreat, or investment opportunity. Enjoy the tranquility of the wooded surroundings while remaining conveniently located just 25 minutes from Winchester. The home is

Ken Evans

RE/MAX Real Estate Connections

415 Puma Trail, Winchester, VA 22602
/50
Starting at $1,700 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

2351 Quinn Ct, 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 $561,884

Last Listing Agent Mark Francis Real Broker LLC

509 Marion St, Winchester, VA 22601

/36
Est $389,025

Not Listed For Sale

110 Hill Valley Dr, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 1,489 Sq Ft
- Built 2000
110 Hill Valley Dr, Winchester, VA 22602

Last Sold Summary
- 164 Days On Market
Last Listing Agent Sheila Pack RE/MAX Roots

/37
$359,000
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
700 Green St, Winchester, VA 22601

You've been dreaming of main-level living, and this is IT! Check all your boxes:3 bedrooms2 full bathroomsOpen-concept family roomBeautifully updated kitchenSpacious kitchen islandPrimary suite with private bath, walk-in shower, and walk-in closetCharming front porch - perfect for morning coffee�� Roof replaced 2018Private back deckFenced

Jeanne Mezzatesta

Colony Realty

700 Green St, 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

44 S Loudoun St Unit 12, Winchester, VA 22601
/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 $255,495

Last Listing Agent Nancy Tessman EXP Realty, LLC

136 Parkside Dr, Winchester, VA 22602

/29
Est $305,563

Not Listed For Sale

509 Braeburn Dr, Winchester, VA 22601
- 2 Beds
- 2.5 Baths
- 1,534 Sq Ft
- Built 1999
509 Braeburn Dr, Winchester, VA 22601

Last Sold Summary
- 7 Days On Market
Last Listing Agent Jen Richards Samson Properties

/47
$405,000

$20K PRICE DROP Under Contract
- 4 Beds
- 2 Baths
- 2,572 Sq Ft
145 Wilkins Dr, Winchester, VA 22602

PRICE DROP! Rare Opportunity on Winchester's East Side with a LOWER-LEVEL IN-LAW SUITE! NEW ROOF (2026) AND NEW BOILER (2025)Welcome home to this spacious 4-bedroom, 2-bath beauty offering a warm, inviting layout and thoughtful updates throughout! The main level features a generous living room, dining room, and a bright kitchen with stainless steel appliances, plus three bedrooms and a

Jeanne Mezzatesta

Colony Realty

145 Wilkins Dr, Winchester, VA 22602
/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

2260 Wilson Blvd, 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 $266,088

Last Listing Agent Michele Gibson Samson Properties

407 van Fossen St, Winchester, VA 22601

/61
Est $684,393

Not Listed For Sale

560 Fair Ln, Winchester, VA 22603
- 3 Beds
- 2.5 Baths
- 2,491 Sq Ft
- Built 1999
560 Fair Ln, Winchester, VA 22603

Last Sold Summary
- 6 Days On Market
Last Listing Agent Mark Laing Keller Williams Realty

/51
$499,900
- 3 Beds
- 3 Baths
- 1,564 Sq Ft
510 S Cameron St, Winchester, VA 22601

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special.Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to

Brock Harris

Samson Properties

510 S Cameron St, Winchester, VA 22601
/7
$1,800 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

619 S Cameron 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 $806,417

Last Listing Agent Tanner Pack RE/MAX Roots

162 Janes Way, Winchester, VA 22602

/62
Est $690,902

Not Listed For Sale

400 Great Mountain Ln, Winchester, VA 22602
- 2 Beds
- 2 Baths
- 1,600 Sq Ft
- Built 2001
400 Great Mountain Ln, Winchester, VA 22602

Last Sold Summary
- 146 Days On Market
Last Listing Agent Leah Clowser RE/MAX Roots

/35
$329,999

$7K PRICE DROP Under Contract
- 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

David Peña

Corcoran McEnearney

124 Worsham Terrace, Winchester, VA 22602
/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 Extended Stay Apartments

548 Brookfield Dr, Winchester, VA 22601
/22
$119,000

Sold Jul 16, 2026

1280 Bobcat Trail, Winchester, VA 22602
- Land
- 10 Acres
- $11,900 per Acre
Last Sold Summary
- 25 Days On Market
Current Estimated Value $163,000

Last Listing Agent Kristin Crosby Samson Properties

1280 Bobcat Trail, Winchester, VA 22602

/34
Est $372,478

Not Listed For Sale

216 Monticello Square, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 2,436 Sq Ft
- Built 2010
216 Monticello Square, Winchester, VA 22602

Last Sold Summary
- 26 Days On Market
Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

/58
$799,900

New Construction
- 3 Beds
- 2.5 Baths
- 2,304 Sq Ft
115 Stetson St, Winchester, VA 22603

No HOA and Completely Finished!!! Great opportunity to own this brand-new, move-in ready ranch home situated on 2.82 beautiful acres! Conveniently located near shopping and commuter routes to Winchester, Martinsburg, and Northern Virginia, this home offers the perfect blend of privacy and accessibility.Designed with an open-concept layout and a desirable split-bedroom floor plan, the home

Brett Sowder

RE/MAX Roots

115 Stetson St, Winchester, VA 22603
/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

2256 Roosevelt Blvd, Winchester, VA 22601
/40
$398,190

Sold May 04, 2026

1821 Harvest Dr, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 1,920 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $207/SF
- 46 Days On Market
Last Listing Agent Brooks Sears Pearson Smith Realty, LLC

1821 Harvest Dr, Winchester, VA 22601

/65
Est $406,658

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
Last Listing Agent Jeffrey Konrady Realty ONE Group Old Towne

/39
$595,390

New Construction
- 3 Beds
- 3 Baths
- 3,200 Sq Ft
116 Magpie Ln, Winchester, VA 22603

NEW BUILD, move in ready single-family home at Hiatt Pointe, 55+ community at Snowden Bridge by Van Metre Homes! The Sierra 39-F2 at Hiatt Pointe is stunning! This home offers 3 bedrooms, 3 full bathrooms, a 2-car front load garage, a finished basement and much more! As you enter the home you are greeted with 9' ceilings, luxury vinyl plank flooring, recessed lighting throughout, programmable

Kerry Wysong

Long & Foster Real Estate, Inc.

116 Magpie Ln, Winchester, VA 22603
/33
Starting at $1,850 Plus Fees
- 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)

110 Bulmer Loop, Winchester, VA 22602
/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 $244,521

Last Listing Agent Alexander Bracke Real Broker, LLC

212 Shawnee Ave, Winchester, VA 22601

/26
Not Listed For Sale

916 N Frederick Pike, Winchester, VA 22603
- 1 Bed
- 1 Bath
- 1,023 Sq Ft
- Built 1941
916 N Frederick Pike, Winchester, VA 22603

Last Sold Summary
- 76 Days On Market
Last Listing Agent Kaitlyn Behr Samson Properties

/23
$795,600

New Construction Pending
- 3 Beds
- 2.5 Baths
- 2,102 Sq Ft
111 Babbs Mountain Rd, Winchester, VA 22603

Modern Elegance on 1.6 Acres – To Be Built! Experience contemporary living at its finest with this stunning 3-bedroom, 2.5-bathroom home, expertly designed by Fauver and Browning Homes. Nestled on 1.6 scenic acres just outside Winchester, this home offers breathtaking views of the rolling meadows leading to Apple Pie Ridge. Spanning 2,102 sq. ft., this home blends modern design with thoughtful

Jeanne Mezzatesta

Colony Realty

111 Babbs Mountain Rd, Winchester, VA 22603
/13
$1,700 Plus Fees
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
- House for Rent
223 Baker St, Winchester, VA 22601

Property Id: 1770094 Available October 1st. This well-maintained 2-bedroom, 1-bath home offers approximately 1,200 sq. ft. of living space plus a spacious upstairs bonus/flex room that works well as a home office, den, additional living area, or other flexible-use space. The home features hardwood flooring and updated LVP, abundant natural light, an updated kitchen with stainless

223 Baker 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 $345,454

Last Listing Agent Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

707 E Cork St, Winchester, VA 22601

/37
Est $431,170

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
Last Listing Agent Jason Aikens RE/MAX Roots

Showing Results 41 - 80, Page 2 of 18

Virginia Winchester County

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Winchester, VA Homes

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