View 398 Pine Ridge Road Winchester, KY MLS# 25501136
$314,000
2

Beds

1.0

Baths

1,170

Sq.Ft.

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 25501259
$314,000
2

Beds

1.0

Baths

1,170

Sq.Ft.

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 211 Ashton Oak Way Winchester, KY MLS# 25501640
  • New Construction
1 of 10
$215,000
Studio

Beds

0.0

Baths

211 Ashton Oak Way

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 101 Royal Oak Drive Winchester, KY MLS# 25501641
$64,900
Studio

Beds

0.0

Baths

101 Royal Oak Drive

Winchester, KY

Bluegrass
View 102 Royal Oak Drive Winchester, KY MLS# 25501642
$64,900
Studio

Beds

0.0

Baths

102 Royal Oak Drive

Winchester, KY

Bluegrass
View 130 E Broadway Street Winchester, KY MLS# 25501480
$245,000
5

Beds

3.0

Baths

2,445

Sq.Ft.

130 E Broadway Street

Winchester, KY

Bluegrass
View 4590 Four Mile Road Winchester, KY MLS# 25501424
$168,000
Studio

Beds

0.0

Baths

4590 Four Mile Road

Winchester, KY

Bluegrass
View 4700 Four Mile Road Winchester, KY MLS# 25501428
$59,500
Studio

Beds

0.0

Baths

4700 Four Mile Road

Winchester, KY

Bluegrass
View 190 Privacy Lane Winchester, KY MLS# 25501332
$260,000
Studio

Beds

0.0

Baths

190 Privacy Lane

Winchester, KY

Bluegrass
View 117 4th Street Winchester, KY MLS# 25501219
$10,000
Studio

Beds

0.0

Baths

117 4th Street

Winchester, KY

Bluegrass
View 27 Ashland Avenue Winchester, KY MLS# 25501148
$188,900
3

Beds

2.0

Baths

1,653

Sq.Ft.

27 Ashland Avenue

Winchester, KY

Bluegrass
View 208 4th Street Winchester, KY MLS# 25501100
$140,000
2

Beds

1.0

Baths

1,254

Sq.Ft.

208 4th Street

Winchester, KY

Bluegrass
View 439 & 475 Old Muddy Creek Road Winchester, KY MLS# 25500904
$109,900
Studio

Beds

0.0

Baths

439 & 475 Old Muddy Creek Road

Winchester, KY

Bluegrass
View 12 Apache Trail Winchester, KY MLS# 25500706
$168,500
3

Beds

2.0

Baths

1,026

Sq.Ft.

12 Apache Trail

Winchester, KY

Bluegrass
View 23 1/2 Wheeler Avenue Winchester, KY MLS# 25500496
$375,000
8

Beds

4.0

Baths

3,706

Sq.Ft.

23 1/2 Wheeler Avenue

Winchester, KY

Bluegrass
View 103 Yorktowne Court Winchester, KY MLS# 25500573
$139,900
3

Beds

1.0

Baths

1,150

Sq.Ft.

103 Yorktowne Court

Winchester, KY

Bluegrass
View 3056 Irvine Road Winchester, KY MLS# 25500166
$299,000
Studio

Beds

0.0

Baths

3056 Irvine Road

Winchester, KY

Bluegrass
View 2996 Irvine Road Winchester, KY MLS# 25500167
$199,900
Studio

Beds

0.0

Baths

2996 Irvine Road

Winchester, KY

Bluegrass
View 206 Jett Drive Winchester, KY MLS# 24018286
  • New Construction
1 of 10
$369,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

206 Jett Drive

Winchester, KY

Bluegrass
View 2110 Athens Boonesboro Road Winchester, KY MLS# 25500014
$235,000
Studio

Beds

0.0

Baths

2110 Athens Boonesboro Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

276

Estimated median home price

$274,900
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 - 100K38
$100K - 200K55
$200K - 300K57
$300K - 400K41
$400K - 500K24
$500K - 600K11
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family142
Townhouse4
Condo0
Commercial12
Rental19
Lots and Land94
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms14

(Data as of 12/24/2025)

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 12/26/2025.