241 total properties
Did you mean the neighborhood Winchester?
View 838 Bypass Road Winchester, KY MLS# 25015909
$614,900
2,906

Sq.Ft.

838 Bypass Road

Winchester, KY

Bluegrass
View 6595 Mt Sterling Road Winchester, KY MLS# 25507834
$609,900
5

Beds

4.0

Baths

4,515

Sq.Ft.

6595 Mt Sterling Road

Winchester, KY

Bluegrass
View 101 S Burns Avenue 1 # 1,2,3,4 Winchester, KY MLS# 25505825
$600,000
8

Beds

4.0

Baths

5,046

Sq.Ft.

101 S Burns Avenue 1 # 1,2,3,4

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
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 600 Boone Avenue Winchester, KY MLS# 25018239
$579,900
4

Beds

3.2

Baths

4,374

Sq.Ft.

600 Boone Avenue

Winchester, KY

Bluegrass
View 2100 Stoner-Ephesus Road Winchester, KY MLS# 26003590
$575,000
2

Beds

2.0

Baths

2,361

Sq.Ft.

2100 Stoner-Ephesus Road

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 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 33-41 Winn Avenue Winchester, KY MLS# 25508043
$550,000
Studio

Beds

0.0

Baths

33-41 Winn Avenue

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 125 Casa Landa Way Winchester, KY MLS# 25508316
$530,000
4

Beds

3.1

Baths

3,848

Sq.Ft.

125 Casa Landa Way

Winchester, KY

Bluegrass
View 808 Bypass Road Winchester, KY MLS# 25011326
$515,000
5,094

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 808 Bypass Road Winchester, KY MLS# 25015851
$515,000
2

Beds

1.1

Baths

5,054

Sq.Ft.

808 Bypass 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 265 S Highland Street Winchester, KY MLS# 26004961
  • Recently Listed
1 of 31
$505,000
8

Beds

4.0

Baths

5,058

Sq.Ft.

265 S Highland Street

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 595 Earlymeade Drive Winchester, KY MLS# 25506943
$499,000
5

Beds

3.1

Baths

3,823

Sq.Ft.

595 Earlymeade Drive

Winchester, KY

Bluegrass
View 414 Fairholme Way Winchester, KY MLS# 25505996
  • New Construction
1 of 45
OPEN HOUSE: Sunday 3/15 1:00 PM - 3:00 PM
$489,900
4

Beds

3.0

Baths

2,300

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25017324
$475,000
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25500168
$475,000
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

271

Estimated median home price

$275,700
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 - 100K31
$100K - 200K57
$200K - 300K64
$300K - 400K36
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family147
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land81
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/14/2026)

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 3/14/2026.