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 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.
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 218 Monteith Drive Winchester, VA MLS# VAWI2009978
  • Recently Listed with Virtual Tour
1 of 24
$389,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

218 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 213 Woodrow Road Winchester, VA MLS# VAFV2039552
  • Recently Listed
1 of 50
$367,499
3

Beds

2.0

Baths

1,416

Sq.Ft.

213 Woodrow Road

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 221 Cobble Stone Drive Winchester, VA MLS# VAFV2039498
$435,000
4

Beds

3.1

Baths

2,413

Sq.Ft.

221 Cobble Stone Drive

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 128 Killbuck Trail Winchester, VA MLS# VAFV2039474
  • Recently Listed
1 of 52
$410,000
3

Beds

4.0

Baths

2,100

Sq.Ft.

128 Killbuck Trail

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 15.63 Acres, 52-2-B Winchester, VA MLS# VAFV2039232
$250,000
Studio

Beds

0.0

Baths

15.63 Acres, 52-2-B

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 19 W Germain Street Winchester, VA MLS# VAWI2009802
$337,000
3

Beds

1.1

Baths

1,280

Sq.Ft.

19 W Germain Street

Winchester, VA

Bright
Courtesy of COTTAGE STREET REALTY LLC
View 1821 Harvest Drive Winchester, VA MLS# VAWI2009960
  • Recently Listed
1 of 40
OPEN HOUSE: Saturday 2/28 1:00 PM - 3:00 PM
$399,990
4

Beds

3.1

Baths

1,920

Sq.Ft.

1821 Harvest Drive

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 1809 Harvest Drive Winchester, VA MLS# VAWI2009962
  • Recently Listed
1 of 40
$419,990
4

Beds

3.1

Baths

1,939

Sq.Ft.

1809 Harvest Drive

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 1813 Harvest Drive Winchester, VA MLS# VAWI2009964
  • Recently Listed
1 of 39
$419,990
4

Beds

3.1

Baths

1,920

Sq.Ft.

1813 Harvest Drive

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 109 Boone Court Winchester, VA MLS# VAFV2039494
  • Recently Listed
1 of 22
$389,880
3

Beds

2.2

Baths

1,989

Sq.Ft.

109 Boone Court

Winchester, VA

Bright
Courtesy of NEW HOME STAR VIRGINIA, LLC
View 376 Charles Street Winchester, VA MLS# VAWI2009942
$185,000
3

Beds

1.0

Baths

1,232

Sq.Ft.

376 Charles Street

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
View 25 W Southwerk Street Winchester, VA MLS# VAWI2009902
$449,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

25 W Southwerk Street

Winchester, VA

Bright
Courtesy of COLONY REALTY

About Winchester

Listings in Winchester, VA

486

Estimated median home price

$442,400
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 - 100K45
$100K - 200K21
$200K - 300K46
$300K - 400K92
$400K - 500K85
$500K - 600K57
$600K - 700K41
$700K - 800K14
$800K - 900K12
$900K - 1M14
$1M - Max59

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family250
Townhouse52
Condo24
Commercial46
Rental151
Lots and Land107
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms0

(Data as of 2/27/2026)

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 2/28/2026.

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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