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Winchester, KY Homes for Sale — Page 5 | Realty.com

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Homes for Sale in Winchester, KY

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18 of 114 Listings

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18 of 114 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced30Active
$325,000
5 bd · 4 ba · 4,456 sqft
410 W Lexington Avenue, Winchester, KY
Tracy M Ison · Bluegrass Home Group
Price Reduced116Active
$1,595,000
3 bd · 3 ba · 4,518 sqft
3166 Colby Road, Winchester, KY
Alyssa M Boley · Coldwell Banker McMahan
Price Reduced33Active
$435,000
3 bd · 2 ba · 1,680 sqft
287 Logan Lick Road, Winchester, KY
Dale Hatton · Dream Maker Realty, LLC

Price Reduced51Active
$399,900
3 bd · 3 ba · 2,288.72 sqft
20 Edgewood Drive, Winchester, KY
Libby VanMeter · Marshall Lane Real Estate - Lexington
49Active
$445,500
3 bd · 3 ba · 2,961 sqft
42 Mockingbird Valley Road, Winchester, KY
Markus Cross · McCallie Real Estate
Price Reduced32Active
$320,000
4 bd · 3 ba · 2,310 sqft
38 N Burns Avenue Street, Winchester, KY
Trina Penn · RE/MAX Creative Realty
68Active
$2,750,000
8 bd · 8 ba · 13,433 sqft
4664 Lexington Road, Winchester, KY
Adam Boardman · Block + Lot Real Estate
Price Reduced55Active
$515,000
3 bd · 2 ba · 2,563 sqft
935 Stoner-Ephesus Road, Winchester, KY
Timothy Saylor · Threshold Real Estate Services
20Active
$316,900
3 bd · 3 ba · 1,858 sqft
200 Dubuy Drive, Winchester, KY
Wayne Elkins · RE/MAX Creative Realty
Price Reduced14Active
$165,000
4 bd · 3 ba · 3,462 sqft
229 S Highland Street, Winchester, KY
Michelle R Blackburn · RE/MAX Creative, Winchester
Price Reduced57Active
$340,000
4 bd · 2 ba · 3,261 sqft
443 S Maple Street, Winchester, KY
Terra Long · Keller Williams Commonwealth
Price Reduced54Active
$155,900
1 bd · 2 ba · 1,056 sqft
101 Alabama Street, Winchester, KY
A. Rebecca Woods · Woods Realty Group
Price Reduced18Active
$490,000
5 bd · 3 ba · 3,102 sqft
110 White Conkwright Road, Winchester, KY
Philip PJ Elder · Omega Real Estate Brokerage LLC
Price Reduced84Active
$649,000
4 bd · 3 ba · 4,928 sqft
186 Chardonnay Court, Winchester, KY
Brenda H Sipes · WEICHERT REALTORS - ABG Properties
Price Reduced22Active
$134,900
2 bd · 1 ba · 986 sqft
174 Cook Avenue, Winchester, KY
A. Rebecca Woods · Woods Realty Group
Price Reduced42Active
$124,000
2 bd · 2 ba · 1,360 sqft
404 Mount Vernon Drive, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC
Price Reduced49Active
$165,000
2 bd · 2 ba · 1,202 sqft
1494 Amster Grove Rd. Road, Winchester, KY
Libby VanMeter · Marshall Lane Real Estate - Lexington
Price Reduced97Active
$2,999,000
6 bd · 5 ba · 3,693 sqft
3049 Ironworks Road, Winchester, KY
Zova M Rothchild · Keller Williams Legacy Group

1…4 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.

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

By feature

New construction
With a pool

Nearby areas

ZIP codes

40475 (269)
40509 (154)
40324 (130)
40356 (128)
40391 (115)
40515 (100)
40511 (78)
40353 (72)

Cities

Lexington (760)
Richmond (269)
Georgetown (130)
Nicholasville (128)
Mt Sterling (71)
Paris (45)
Stanton (36)
Berea (26)

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

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.

Nearby areas

ZIP codes

40475 (269)
40509 (154)
40324 (130)
40356 (128)
40391 (115)
40515 (100)
40511 (78)
40353 (72)

Cities

Lexington (760)
Richmond (269)
Georgetown (130)
Nicholasville (128)
Mt Sterling (71)
Paris (45)
Stanton (36)
Berea (26)