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Winchester, KY Homes for Sale — Page 2 | Realty.com

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3 beds New construction With a pool

Homes for Sale in Winchester, KY

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24 of 117 Listings

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24 of 117 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

26Active
$249,900
3 bd · 2 ba · 1,492 sqft
317 Vanover Way, Winchester, KY
Austina Bruton · Rector Hayden Realtors
Price Reduced29Active
$275,000
3 bd · 2 ba · 1,500 sqft
103 Southern Court, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
40Active
$498,000
4 bd · 3 ba · 2,496 sqft
1780 Stoner-Ephesus Road, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC

Price Reduced29Active
$139,000
3 bd · 1 ba · 1,842 sqft
5 S Burns Avenue, Winchester, KY
Tirza Howard · The Howard Realty Co
24Active
$199,900
2 bd · 1 ba · 1,149 sqft
287 Ecton Rd, Winchester, KY
Vicky Kamousi · Metro Realty
Price Reduced60Active
$248,900
3 bd · 1 ba · 2,249 sqft
11304 Irvine Road, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC
Price Reduced64Active
$349,900
3 bd · 3 ba · 1,846 sqft
420 Calmes Boulevard, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
19Active
$350,000
3 bd · 3 ba · 2,592 sqft
135 E Broadway Street, Winchester, KY
Dale Hatton · Dream Maker Realty, LLC
Price Reduced31Active
$275,000
3 bd · 2 ba · 1,512 sqft
4305 Old Boonesboro Road, Winchester, KY
Brenda H Sipes · WEICHERT REALTORS - ABG Properties
25Active
$165,000
3 bd · 1 ba · 1,249 sqft
209 E Washington Street, Winchester, KY
Michelle R Blackburn · RE/MAX Creative, Winchester
Price Reduced24Active
$189,900
3 bd · 2 ba · 915 sqft
225 Buffalo Trace, Winchester, KY
Tyler I Back · The Brokerage
Price Reduced18Active
$355,000
3 bd · 2 ba · 1,990 sqft
11 Stoney Brook Drive 1, Winchester, KY
Garry H Milton · Milton and Associates Real Estate
Price Reduced60Active
$229,900
3 bd · 1 ba · 1,272 sqft
119 Tower Lane, Winchester, KY
Shawna Wever · Wever Realty LLC
23Active
$225,000
4 bd · 2 ba · 1,400 sqft
522 Acadia Way, Winchester, KY
Tyler I Back · The Brokerage
40Active
$244,000
3 bd · 2 ba · 1,692 sqft
54 Locust Drive, Winchester, KY
Natalie Avant · Berkshire Hathaway HomeServices Foster Realtors
63Active
$785,000
5 bd · 3 ba · 4,676 sqft
217 Wades Mill Road, Winchester, KY
Michelle R Blackburn · RE/MAX Creative, Winchester
21Active
$135,000
2 bd · 1 ba · 807 sqft
3208 Ford Hampton Road, Winchester, KY
Bob Sophiea · eXp Realty, LLC
50Active
$639,000
5 bd · 4 ba · 5,011 sqft
104 Teal Lane, Winchester, KY
The Gooch Team - Kristy Gooch · RE/MAX Elite Realty
46Active
$1,400,000
4 bd · 4 ba · 5,613 sqft
1400 Craig Crossing, Winchester, KY
Ken Ritter · Coldwell Banker McMahan
26Active
$234,900
3 bd · 2 ba · 1,904 sqft
528 Estes Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
Price Reduced27Active
$275,000
4 bd · 2 ba · 1,752 sqft
198 Hilltop Drive, Winchester, KY
Stephanie Hacker · Kentucky Residential Real Estate, LLC
65Active
$359,900
3 bd · 2 ba · 2,269 sqft
15 Moundale Avenue, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
Price Reduced24Active
$219,900
3 bd · 1 ba · 1,100 sqft
125 Kittison Drive, Winchester, KY
Kathryn M Cheuvront · Coldwell Banker McMahan
Price Reduced12Active
$249,000
4 bd · 2 ba · 1,996 sqft
59 Hillcrest Drive, Winchester, KY
Dylan Langdon · The Agency

1 2 3…5

Listing data & MLS disclosures

Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively 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. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.
Metro Search (Greater Louisville Association of REALTORS): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this web site comes in part from the IDX Program of GLAR\Metro Search,Inc. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Information is deemed reliable but not guaranteed, .
Listing information ©2026 Greater Louisville AOR® and Metro Search, Inc. All Rights Reserved. Last Updated: 2026-09-03 15:14:55 UTC

Winchester housing market

July 2026 · This period is still settling

Selling at 99.6% of asking price

Sales here are closing essentially at asking. MLS · 50 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 14, 2026

Median sale price: $241,250$196,175–$368,750 typical range
Price per sq. ft.: $160
Sales: 28
Paid in cash: 57.1%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $319,900
Homes for sale: 113

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: -0.7%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,544 sq. ft.

Winchester, KY community profile

Population: 19,583
Median income: $57,052
Housing units: 9,262
People per sq. mi.: 81.2
Area: 241.2 sq. mi.

Source: HJN community data

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX information is provided exclusively 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. Real estate listings held by IDX brokerage firms other than Realty.com, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.
Metro Search (Greater Louisville Association of REALTORS): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this web site comes in part from the IDX Program of GLAR\Metro Search,Inc. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Information is deemed reliable but not guaranteed, .
Listing information ©2026 Greater Louisville AOR® and Metro Search, Inc. All Rights Reserved. Last Updated: 2026-09-03 15:14:55 UTC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Co-ops

By feature

New construction
With a pool

Nearby areas

ZIP codes

40475 (277)
40509 (155)
40391 (116)
40324 (112)
40356 (112)
40515 (109)
40511 (80)
40353 (72)

Cities

Lexington (779)
Richmond (277)
Georgetown (112)
Nicholasville (112)
Mt Sterling (71)
Paris (43)
Stanton (38)
Berea (32)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Winchester, KY community profile

Population: 19,583
Median income: $57,052
Housing units: 9,262
People per sq. mi.: 81.2
Area: 241.2 sq. mi.

Source: HJN community data

Nearby areas

ZIP codes

40475 (277)
40509 (155)
40391 (116)
40324 (112)
40356 (112)
40515 (109)
40511 (80)
40353 (72)

Cities

Lexington (779)
Richmond (277)
Georgetown (112)
Nicholasville (112)
Mt Sterling (71)
Paris (43)
Stanton (38)
Berea (32)

Winchester housing market

July 2026 · This period is still settling

Selling at 99.6% of asking price

Sales here are closing essentially at asking. MLS · 50 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 14, 2026

Median sale price: $241,250$196,175–$368,750 typical range
Price per sq. ft.: $160
Sales: 28
Paid in cash: 57.1%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $319,900
Homes for sale: 113

Price trend · Assessor repeat sales, as of Jul 31, 2026

Year-over-year: -0.7%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

Median home size: 1,544 sq. ft.