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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

3Active
$670,000
3 bd · 2 ba · 2,261 sqft
113 Bella Shae Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
3Active
$700,000
3 bd · 2 ba · 2,400 sqft
415 Alexis Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
Price Reduced37Active
$219,000
3 bd · 2 ba · 1,261 sqft
14 Cook Avenue, Winchester, KY
Janna L Smith · United Real Estate Bluegrass

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
Price Reduced32Active
$310,000
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
$325,000
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 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

August 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 32 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 19, 2026

Median sale price: $315,000$218,000–$595,000 typical range
Price per sq. ft.: $173
Sales: 37
Paid in cash: 32.4%

Homes on the market · MLS, as of Aug 30, 2026

Median list price: $319,900
Homes for sale: 111

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

Year-over-year: 14.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 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

Explore Winchester homes

By price

Homes Under $300K
Homes Under $400K
Homes Under $500K
Homes Under $600K
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By bedrooms

3 Bedroom Homes

Nearby areas

ZIP codes

40475 (295)
40509 (154)
40391 (114)
40515 (113)
40353 (84)
40511 (81)
40324 (79)
40502 (73)

Cities

Lexington (750)
Richmond (295)
Mount Sterling (83)
Georgetown (79)
Nicholasville (65)
Paris (48)
Stanton (39)
Carlisle (28)

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Nearby areas

ZIP codes

40475 (295)
40509 (154)
40391 (114)
40515 (113)
40353 (84)
40511 (81)
40324 (79)
40502 (73)

Cities

Lexington (750)
Richmond (295)
Mount Sterling (83)
Georgetown (79)
Nicholasville (65)
Paris (48)
Stanton (39)
Carlisle (28)

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

August 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 32 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 19, 2026

Median sale price: $315,000$218,000–$595,000 typical range
Price per sq. ft.: $173
Sales: 37
Paid in cash: 32.4%

Homes on the market · MLS, as of Aug 30, 2026

Median list price: $319,900
Homes for sale: 111

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

Year-over-year: 14.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,544 sq. ft.