View 424 Highland Avenue Winchester, VA MLS# VAWI2010002
  • Recently Listed with Virtual Tour
1 of 51
$279,000
2

Beds

1.0

Baths

759

Sq.Ft.

424 Highland Avenue

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 720 Panther Drive Winchester, VA MLS# VAFV2039676
  • New Construction
1 of 6
$350,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

720 Panther Drive

Winchester, VA

Bright
Courtesy of PRESLEE REAL ESTATE
View 115 Dogwood Trail Winchester, VA MLS# VAFV2039682
  • Recently Listed
1 of 21
$359,017
3

Beds

2.1

Baths

1,660

Sq.Ft.

115 Dogwood Trail

Winchester, VA

Bright
Courtesy of Bowie - Weichert, Realtors - Blue Ribbon
The time to sell is now! THE TIME TO SELL IS NOW!
View 234 Monteith Drive Winchester, VA MLS# VAWI2009986
  • Recently Listed with Virtual Tour
1 of 25
$399,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

234 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 433-435 Bryarly Road Winchester, VA MLS# VAFV2039646
$325,000
4

Beds

0.0

Baths

433-435 Bryarly Road

Winchester, VA

Bright
Courtesy of MINT REALTY
View Homesite 25 Williamson Road Winchester, VA MLS# VAFV2039652
  • Recently Listed with Virtual Tour
1 of 22
OPEN HOUSE: Thursday 2/26 12:00 PM - 3:00 PM
$552,990
3

Beds

2.0

Baths

2,476

Sq.Ft.

Homesite 25 Williamson Road

Winchester, VA

Bright
Courtesy of NEW HOME STAR VIRGINIA, LLC
View 117 Whipp Drive Winchester, VA MLS# VAFV2039662
  • Recently Listed
1 of 41
$489,000
4

Beds

2.1

Baths

2,076

Sq.Ft.

117 Whipp Drive

Winchester, VA

Bright
Courtesy of CAMBRIDGE PREMIER REALTY, LLC.
View 104 Keystone # HOMESITE 1092 Winchester, VA MLS# VAFV2039664
  • Recently Listed with Virtual Tour
1 of 49
$452,719
3

Beds

2.1

Baths

2,191

Sq.Ft.

104 Keystone # HOMESITE 1092

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 632 Watson Avenue Winchester, VA MLS# VAWI2009994
$224,900
3

Beds

2.0

Baths

1,621

Sq.Ft.

632 Watson Avenue

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 101 Sovereign Court Winchester, VA MLS# VAFV2038648
$595,000
4

Beds

2.1

Baths

3,462

Sq.Ft.

101 Sovereign Court

Winchester, VA

Bright
Courtesy of EXP REALTY, LLC
View 105 Parkside Drive Winchester, VA MLS# VAFV2039526
$269,900
2

Beds

1.1

Baths

1,385

Sq.Ft.

105 Parkside Drive

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 215 Cochise Trail Winchester, VA MLS# VAFV2039592
$410,000
3

Beds

2.1

Baths

1,608

Sq.Ft.

215 Cochise Trail

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 320 Bethel Grange Road Winchester, VA MLS# VAFV2039596
$199,900
3

Beds

1.0

Baths

1,032

Sq.Ft.

320 Bethel Grange Road

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 105 Castaway Winchester, VA MLS# VAFV2039606
  • Recently Listed
1 of 27
$374,990
3

Beds

2.1

Baths

1,784

Sq.Ft.

105 Castaway

Winchester, VA

Bright
Courtesy of BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
View 1917 Harvest Drive Winchester, VA MLS# VAWI2009976
  • Recently Listed with Virtual Tour
1 of 58
$549,900
4

Beds

2.1

Baths

2,234

Sq.Ft.

1917 Harvest Drive

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 540 Monticello Street Winchester, VA MLS# VAWI2009974
$605,000
7

Beds

0.0

Baths

540 Monticello Street

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 2643 Middle Road Winchester, VA MLS# VAWI2009924
  • Recently Listed
1 of 45
$500,000
4

Beds

3.1

Baths

2,524

Sq.Ft.

2643 Middle Road

Winchester, VA

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 108 Senseny Glen Drive Winchester, VA MLS# VAFV2039554
  • Recently Listed
1 of 28
OPEN HOUSE: Saturday 2/28 2:00 PM - 4:00 PM
$423,000
3

Beds

2.0

Baths

1,397

Sq.Ft.

108 Senseny Glen Drive

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 431 Jefferson Street Winchester, VA MLS# VAWI2009944
$419,900
3

Beds

1.1

Baths

1,632

Sq.Ft.

431 Jefferson Street

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 188 Marquis Court Winchester, VA MLS# VAFV2039520
  • Recently Listed
1 of 42
$699,900
4

Beds

3.1

Baths

2,110

Sq.Ft.

188 Marquis Court

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.

About Winchester

Listings in Winchester, VA

485

Estimated median home price

$439,990
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 - 100K44
$100K - 200K19
$200K - 300K44
$300K - 400K98
$400K - 500K87
$500K - 600K57
$600K - 700K38
$700K - 800K15
$800K - 900K11
$900K - 1M14
$1M - Max58

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family251
Townhouse52
Condo27
Commercial45
Rental139
Lots and Land103
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 2/25/2026)

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 2/26/2026.

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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