294 total properties
Did you mean the neighborhood Winchester?
View 12 Pocahontas Trail Winchester, KY MLS# 26012275
  • Recently Listed
1 of 21
$249,900
3

Beds

2.0

Baths

1,064

Sq.Ft.

12 Pocahontas Trail

Winchester, KY

Bluegrass
View 599 BLT Way Winchester, KY MLS# 26012007
  • Recently Listed
1 of 57
$1,599,900
20,252

Sq.Ft.

599 BLT Way

Winchester, KY

Bluegrass
View 7300 Old Boonesboro Road Winchester, KY MLS# 26012036
$785,000
4

Beds

3.0

Baths

3,311

Sq.Ft.

7300 Old Boonesboro Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 133 Bay Hill Drive Winchester, KY MLS# 26012064
  • Recently Listed
1 of 24
$280,000
4

Beds

3.1

Baths

3,276

Sq.Ft.

133 Bay Hill Drive

Winchester, KY

Bluegrass
View 23 Wheeler Avenue Winchester, KY MLS# 26011905
  • Recently Listed
1 of 51
$400,000
8

Beds

5.0

Baths

4,687

Sq.Ft.

23 Wheeler Avenue

Winchester, KY

Bluegrass
View 125 Kittison Drive Winchester, KY MLS# 26011953
  • Recently Listed
1 of 22
$239,000
3

Beds

1.0

Baths

1,100

Sq.Ft.

125 Kittison Drive

Winchester, KY

Bluegrass
View 0 Fairholme Way Winchester, KY MLS# 26011689
  • Recently Listed
1 of 3
$399,000
Studio

Beds

0.0

Baths

0 Fairholme Way

Winchester, KY

Bluegrass
View 4578 Combs Ferry Road Winchester, KY MLS# 26011707
  • Recently Listed
1 of 48
$1,750,000
3

Beds

2.0

Baths

1,860

Sq.Ft.

4578 Combs Ferry Road

Winchester, KY

Bluegrass
View 116 Sturbridge Lane Winchester, KY MLS# 26011782
  • Recently Listed
1 of 37
$279,000
3

Beds

2.0

Baths

1,260

Sq.Ft.

116 Sturbridge Lane

Winchester, KY

Bluegrass
View 3166 Colby Road Winchester, KY MLS# 26011538
  • Recently Listed
1 of 120
$1,695,000
3

Beds

2.1

Baths

4,518

Sq.Ft.

3166 Colby Road

Winchester, KY

Bluegrass
View 6595 Mt Sterling Road Winchester, KY MLS# 26011548
  • Recently Listed
1 of 65
$609,900
5

Beds

4.0

Baths

4,515

Sq.Ft.

6595 Mt Sterling Road

Winchester, KY

Bluegrass
View 225 Buffalo Trace Winchester, KY MLS# 26011564
  • Recently Listed
1 of 24
$199,900
3

Beds

2.0

Baths

915

Sq.Ft.

225 Buffalo Trace

Winchester, KY

Bluegrass
View 316 Maryland Avenue Winchester, KY MLS# 26011496
  • Recently Listed
1 of 25
$255,000
3

Beds

2.0

Baths

1,809

Sq.Ft.

316 Maryland Avenue

Winchester, KY

Bluegrass
View 13 Lakeview Drive Winchester, KY MLS# 26011497
  • Recently Listed
1 of 39
$315,000
3

Beds

2.0

Baths

1,932

Sq.Ft.

13 Lakeview Drive

Winchester, KY

Bluegrass
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$124,500
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

Winchester, KY

Bluegrass
View 106 Bella Shae Way Winchester, KY MLS# 24025577
  • New Construction
1 of 3
$645,000
4

Beds

2.1

Baths

2,526

Sq.Ft.

106 Bella Shae Way

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 111 Bella Shae Way Winchester, KY MLS# 24025579
  • New Construction
1 of 3
$825,000
3

Beds

2.1

Baths

2,995

Sq.Ft.

111 Bella Shae Way

Winchester, KY

Bluegrass
View 113 Bella Shae Way Winchester, KY MLS# 24025580
  • New Construction
1 of 3
$670,000
3

Beds

2.0

Baths

2,261

Sq.Ft.

113 Bella Shae Way

Winchester, KY

Bluegrass
View 414 Alexis Way Winchester, KY MLS# 24025581
  • New Construction
1 of 22
$665,000
3

Beds

2.1

Baths

2,643

Sq.Ft.

414 Alexis Way

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

291

Estimated median home price

$275,000
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 - 100K29
$100K - 200K65
$200K - 300K73
$300K - 400K41
$400K - 500K18
$500K - 600K14
$600K - 700K11
$700K - 800K11
$800K - 900K2
$900K - 1M4
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family171
Townhouse4
Condo0
Commercial13
Rental19
Lots and Land90
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/10/2026)

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 6/10/2026.