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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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15 of 111 Listings

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15 of 111 Listings

Price Reduced33

Homes for Sale in Winchester, KY

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15 of 111 Listings

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Homes for Sale in Winchester, KY

15 of 111 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced33

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$349,000

3 bd · 3 ba · 1,945 sqft

309 Gallahadion Court, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced16Active

$124,500

2 bd · 1 ba · 876 sqft

122 Callaway Street SE Callaway Street, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

22Active

$665,000

3 bd · 3 ba · 2,643 sqft

414 Alexis Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced35Active

$258,900

2 bd · 1 ba · 849 sqft

955 Right Angle Road, Winchester, KY

William Childers · WTC Realty LLC

3Active

$645,000

4 bd · 3 ba · 2,526 sqft

106 Bella Shae Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

3Active

$825,000

3 bd · 3 ba · 2,995 sqft

111 Bella Shae Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

4Active

$635,000

4 bd · 3 ba · 2,537 sqft

422 Alexis Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

4Active

$625,000

3 bd · 3 ba · 2,405 sqft

424 Alexis Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

9Active

$785,000

4 bd · 3 ba · 2,476 sqft

425 Alexis Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

10Active

$550,000

3 bd · 3 ba · 2,200 sqft

107 Bella Shae Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

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 Reduced116Active

$1,595,000

3 bd · 3 ba · 4,518 sqft

3166 Colby Road, Winchester, KY

Alyssa M Boley · Coldwell Banker McMahan

Price Reduced33Active

$425,000

3 bd · 2 ba · 1,680 sqft

287 Logan Lick Road, Winchester, KY

Dale Hatton · Dream Maker Realty, LLC

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
Homes Under $700K

By bedrooms

3 Bedroom Homes

Nearby areas

ZIP codes

40475 (300)
40509 (158)
40391 (111)
40515 (109)
40353 (92)
40511 (87)
40324 (73)
40517 (72)

Cities

Lexington (741)
Richmond (300)
Mount Sterling (91)
Georgetown (73)
Nicholasville (65)
Paris (54)
Irvine (42)
Stanton (39)

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

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.

Nearby areas

ZIP codes

40475 (300)
40509 (158)
40391 (111)
40515 (109)
40353 (92)
40511 (87)
40324 (73)
40517 (72)

Cities

Lexington (741)
Richmond (300)
Mount Sterling (91)
Georgetown (73)
Nicholasville (65)
Paris (54)
Irvine (42)
Stanton (39)

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.