View 103 Castaway Place Winchester, VA MLS# VAFV2038396
  • Adult Community
1 of 29
$374,990
3

Beds

2.1

Baths

1,752

Sq.Ft.

103 Castaway Place

Winchester, VA

Bright
Courtesy of BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
View 166 Graywolf Trail Winchester, VA MLS# VAFV2038002
$374,900
4

Beds

3.0

Baths

1,840

Sq.Ft.

166 Graywolf Trail

Winchester, VA

Bright
Courtesy of EXP REALTY, LLC
View 217 Myrtle Avenue Winchester, VA MLS# VAWI2009772
$374,900
3

Beds

1.0

Baths

907

Sq.Ft.

217 Myrtle Avenue

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
The time to sell is now! THE TIME TO SELL IS NOW!
View 2431 Cedar Creek Grade Winchester, VA MLS# VAFV2033452
$370,000
3

Beds

1.1

Baths

1,036

Sq.Ft.

2431 Cedar Creek Grade

Winchester, VA

Bright
Courtesy of CEDAR CREEK REAL ESTATE
View 126 N Euclid Avenue Winchester, VA MLS# VAWI2009594
$370,000
4

Beds

3.0

Baths

1,868

Sq.Ft.

126 N Euclid Avenue

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
View 222 Monteith Drive Winchester, VA MLS# VAWI2009526
  • New Construction with Virtual Tour
1 of 27
$369,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

222 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 230 Monteith Drive Winchester, VA MLS# VAWI2009528
  • New Construction with Virtual Tour
1 of 23
OPEN HOUSE: Sunday 1/18 12:00 PM - 3:00 PM
$369,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

230 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View Lot 1 Tavistock Drive Winchester, VA MLS# VAFV2019074
$369,900
Studio

Beds

0.0

Baths

Lot 1 Tavistock Drive

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER
View 219 Shenandaoh Trail Winchester, VA MLS# VAFV2023792
  • New Construction
1 of 30
$369,900
3

Beds

2.1

Baths

1,660

Sq.Ft.

219 Shenandaoh Trail

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 222 Crestwood Lane Winchester, VA MLS# VAFV2037554
  • Adult Community
1 of 41
$369,000
2

Beds

2.0

Baths

1,260

Sq.Ft.

222 Crestwood Lane

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 508 Grouse Winchester, VA MLS# VAFV2036898
  • New Construction
1 of 63
$365,000
3

Beds

2.1

Baths

2,520

Sq.Ft.

508 Grouse

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER
View 127 Shirley Street Winchester, VA MLS# VAWI2009378
$365,000
4

Beds

2.0

Baths

1,780

Sq.Ft.

127 Shirley Street

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 323 Russelcroft Road Winchester, VA MLS# VAWI2009662
  • Recently Listed
1 of 40
OPEN HOUSE: Sunday 1/18 1:00 PM - 4:00 PM
$365,000
4

Beds

2.0

Baths

1,534

Sq.Ft.

323 Russelcroft Road

Winchester, VA

Bright
Courtesy of SPRING HILL REAL ESTATE, LLC.
View 701 Hickory Trail Winchester, VA MLS# VAFV2038814
  • Recently Listed
1 of 46
$365,000
3

Beds

2.1

Baths

1,660

Sq.Ft.

701 Hickory Trail

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP CAPITAL
View 1619 Tomahawk Trail Winchester, VA MLS# VAFV2038460
  • New Construction
1 of 19
$364,000
3

Beds

3.0

Baths

1,850

Sq.Ft.

1619 Tomahawk Trail

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 425 Bluebird Trail Winchester, VA MLS# VAFV2037504
  • New Construction
1 of 30
$360,000
3

Beds

2.0

Baths

1,276

Sq.Ft.

425 Bluebird Trail

Winchester, VA

Bright
Courtesy of PRESLEE REAL ESTATE
View 45 and 45 1/2 Race Street Winchester, VA MLS# VAWI2009612
$360,000
4

Beds

0.0

Baths

45 and 45 1/2 Race Street

Winchester, VA

Bright
Courtesy of CORCORAN MCENEARNEY
View 45 and 45 1/2 Race Street Winchester, VA MLS# VAWI2009722
$360,000
2

Beds

1.0

Baths

1,249

Sq.Ft.

45 and 45 1/2 Race Street

Winchester, VA

Bright
Courtesy of CORCORAN MCENEARNEY
View 113 Killbuck Trail Winchester, VA MLS# VAFV2038734
  • Recently Listed
1 of 43
$359,900
3

Beds

3.0

Baths

2,324

Sq.Ft.

113 Killbuck Trail

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER
View 2952 Grace Street Winchester, VA MLS# VAWI2009724
$359,900
3

Beds

1.0

Baths

960

Sq.Ft.

2952 Grace Street

Winchester, VA

Bright
Courtesy of Weichert Realtors - Reston/Herndon

About Winchester

Listings in Winchester, VA

459

Estimated median home price

$449,000
Winchester VA Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Virginia real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, VA.

Homes for Sale by Price in Winchester, VA

PriceCount
$0 - 100K50
$100K - 200K16
$200K - 300K40
$300K - 400K92
$400K - 500K77
$500K - 600K49
$600K - 700K41
$700K - 800K12
$800K - 900K12
$900K - 1M13
$1M - Max57

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family244
Townhouse49
Condo20
Commercial40
Rental144
Lots and Land101
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms0

(Data as of 1/16/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Harrisonburg-Rockingham Association of REALTORS. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers' personal, non-commercial use and may not be reproduced or redistribute. Its sole purpose is to be used for no other purpose than to identify prospective properties consumers may be interested in purchasing. p>

Data is updated as of 1/18/2026.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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