287 total properties
Did you mean the neighborhood Winchester?
View 7919 Mt Sterling Road Winchester, KY MLS# 26012124
$595,000
4

Beds

3.1

Baths

3,431

Sq.Ft.

7919 Mt Sterling Road

Winchester, KY

Bluegrass
View 104 Bella Shae Way Winchester, KY MLS# 26000264
  • New Construction
1 of 10
$591,650
3

Beds

2.1

Baths

2,200

Sq.Ft.

104 Bella Shae Way

Winchester, KY

Bluegrass
View 529 Bullion Boulevard # 3B Winchester, KY MLS# 23015571
$575,000
Studio

Beds

0.0

Baths

529 Bullion Boulevard # 3B

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1025 Colby Road Winchester, KY MLS# 26005455
$575,000
Studio

Beds

0.0

Baths

1025 Colby Road

Winchester, KY

Bluegrass
View 108 Bella Shae Way Winchester, KY MLS# 26010352
$558,900
3

Beds

2.0

Baths

2,280

Sq.Ft.

108 Bella Shae Way

Winchester, KY

Bluegrass
View 1395 Two Mile Road Winchester, KY MLS# 23018854
$550,500
Studio

Beds

0.0

Baths

1395 Two Mile Road

Winchester, KY

Bluegrass
View 609 Bullion Boulevard # 3A Winchester, KY MLS# 23015569
$550,000
Studio

Beds

0.0

Baths

609 Bullion Boulevard # 3A

Winchester, KY

Bluegrass
View 107 Bella Shae Way Winchester, KY MLS# 24025578
  • New Construction
1 of 10
$550,000
3

Beds

2.1

Baths

2,200

Sq.Ft.

107 Bella Shae Way

Winchester, KY

Bluegrass
View 110 White Conkwright Road Winchester, KY MLS# 26007022
$550,000
5

Beds

3.0

Baths

3,102

Sq.Ft.

110 White Conkwright Road

Winchester, KY

Bluegrass
View 600 Boone Avenue Winchester, KY MLS# 26013378
  • Recently Listed
1 of 36
$549,900
4

Beds

3.2

Baths

4,173

Sq.Ft.

600 Boone Avenue

Winchester, KY

Bluegrass
View 146 Hawthorne Drive Winchester, KY MLS# 26010893
$539,900
5

Beds

3.1

Baths

2,711

Sq.Ft.

146 Hawthorne Drive

Winchester, KY

Bluegrass
View 220 Athens Boonsboro Road Winchester, KY MLS# 25012986
$531,000
5,012

Sq.Ft.

220 Athens Boonsboro Road

Winchester, KY

Bluegrass
View 35-37 Hays Street Winchester, KY MLS# 26002170
$515,000
1,440

Sq.Ft.

35-37 Hays Street

Winchester, KY

Bluegrass
View 935 Stoner-Ephesus Road Winchester, KY MLS# 26009385
$515,000
3

Beds

2.0

Baths

2,563

Sq.Ft.

935 Stoner-Ephesus Road

Winchester, KY

Bluegrass
View 1005 Early Drive Winchester, KY MLS# 20111871
$500,000
Studio

Beds

0.0

Baths

1005 Early Drive

Winchester, KY

Bluegrass
View 808 Bypass Road Winchester, KY MLS# 26008729
$500,000
1.0

Baths

5,054

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 16 Manor Drive Winchester, KY MLS# 26010312
$499,900
4

Beds

3.0

Baths

5,646

Sq.Ft.

16 Manor Drive

Winchester, KY

Bluegrass
View 182 Chardonnay Court Winchester, KY MLS# 26013305
  • Recently Listed
1 of 64
$499,000
5

Beds

2.1

Baths

3,097

Sq.Ft.

182 Chardonnay Court

Winchester, KY

Bluegrass
View 33-41 Winn Avenue Winchester, KY MLS# 25508043
$490,000
Studio

Beds

0.0

Baths

33-41 Winn Avenue

Winchester, KY

Bluegrass
View 414 Fairholme Way Winchester, KY MLS# 26011136
  • New Construction
1 of 38
OPEN HOUSE: Saturday 6/20 1:00 PM - 3:00 PM
$484,900
4

Beds

3.0

Baths

2,418

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

296

Estimated median home price

$274,700
Winchester KY Homes for Sale & Properties

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

Homes for Sale by Price in Winchester, KY

PriceCount
$0 - 100K30
$100K - 200K65
$200K - 300K73
$300K - 400K47
$400K - 500K18
$500K - 600K16
$600K - 700K10
$700K - 800K9
$800K - 900K2
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family175
Townhouse4
Condo0
Commercial13
Rental18
Lots and Land91
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/19/2026)

Information deemed reliable but not guaranteed.

Listing data provided courtesy of the Internet Data Exchange Program of Bluegrass REALTORS.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Bluegrass 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 used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 6/20/2026.