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Winchester, KY Homes for Sale — Page 3 | Realty.com

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Homes for Sale in Winchester, KY

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24 of 111 Listings

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24 of 111 Listings

Price Reduced26

Homes for Sale in Winchester, KY

Hide Map

24 of 111 Listings

Map

Homes for Sale in Winchester, KY

24 of 111 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced26

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$254,900

3 bd · 2 ba · 1,715 sqft

122 Sunset Heights, Winchester, KY

James Woodrum · RE/MAX Creative, Winchester

82Active

$2,299,000

5 bd · 4 ba · 6,284 sqft

5039 Combs Ferry Road, Winchester, KY

K Meredith Lane · Bluegrass Sotheby's International Realty

29Active

$289,900

3 bd · 2 ba · 1,254 sqft

47 Cherokee Court, Winchester, KY

Holly L Goeing · The Agency

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced36Active

$299,900

4 bd · 3 ba · 1,963 sqft

444 Wellington Way, Winchester, KY

Michael R Hilario · The Agency

37Active

$639,000

3 bd · 1 ba · 1,962 sqft

9930 Mount Sterling Road, Winchester, KY

Dale Hatton · Dream Maker Realty, LLC

70Active

$220,000

3 bd · 1 ba · 1,140 sqft

15 Maryland Avenue, Winchester, KY

Rachael Benezet · Bluegrass Properties Group

70Active

$265,000

5 bd · 4 ba · 1,714 sqft

109 5th Street, Winchester, KY

Ernesto Martinez · Guide Realty, Inc.

Price Reduced43Active

$359,900

4 bd · 2 ba · 2,352 sqft

107 S Burns Avenue, Winchester, KY

Lauren Lewis · Christies International Real Estate Bluegrass

Price Reduced22Active

$198,000

3 bd · 1 ba · 1,453 sqft

213 E Broadway Street, Winchester, KY

Nik Markovich · GSP Homes

63Active

$769,900

3 bd · 3 ba · 2,200 sqft

330 Spencer Lane, Winchester, KY

Libby VanMeter · Keller Williams Legacy Group

Price Reduced18Active

$169,000

3 bd · 1 ba · 1,046 sqft

175 Magnolia Street, Winchester, KY

A. Rebecca Woods · Woods Realty Group

23Active

$204,900

3 bd · 1 ba · 1,128 sqft

38 MacKay Avenue, Winchester, KY

Nena Honaker · Tom Goebel & Company

109Active

$1,125,000

3 bd · 4 ba · 3,672 sqft

2100 Irvine Road 40391, Winchester, KY

Lucy Martin Jenkins · United Real Estate Bluegrass

Price Reduced46Active

$229,000

3 bd · 1 ba · 1,050 sqft

30 Virginia Avenue, Winchester, KY

Brenda H Sipes · WEICHERT REALTORS - ABG Properties

54Active

$375,000

4 bd · 2 ba · 1,828 sqft

609 W Barlow Drive, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

48Active

$304,900

3 bd · 3 ba · 1,904 sqft

335 Newcastle Lane, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

Price Reduced43Active

$296,000

4 bd · 2 ba · 1,953 sqft

6 French Avenue, Winchester, KY

A. Rebecca Woods · Woods Realty Group

49Active

$1,500,000

3 bd · 2 ba · 1,860 sqft

4578 Combs Ferry Road, Winchester, KY

Joshua A Davis · The Agency

Price Reduced12Active

$264,900

5 bd · 2 ba · 2,214 sqft

55 Hillcrest Drive, Winchester, KY

Nina Vanetten · RE/MAX Elite Lexington

54Active

$390,000

4 bd · 1 ba · 2,063 sqft

7353 Ironworks Road, Winchester, KY

Nancy Smith · Rector Hayden Realtors

Price Reduced58Active

$74,950

2 bd · 1 ba · 825 sqft

1860 Ford Road, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

Price Reduced50Active

$399,900

4 bd · 3 ba · 1,500 sqft

240 Athens Boonesboro Road, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

Price Reduced33Active

$219,900

3 bd · 3 ba · 1,522 sqft

115 Quail Ridge Road, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced40Active

$488,000

4 bd · 3 ba · 2,496 sqft

1780 Stoner-Ephesus Road, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

1 2 3 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.