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Winchester, KY Homes for Sale | Realty.com

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Homes for Sale in Winchester, KY

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24 of 113 Listings

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24 of 113 Listings

Price Reduced64

Homes for Sale in Winchester, KY

Hide Map

24 of 113 Listings

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Homes for Sale in Winchester, KY

24 of 113 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced64

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$369,900

4 bd · 3 ba · 1,978 sqft

107 Hibiscus Lane, Winchester, KY

Christa Joynt · Keller Williams Commonwealth

29Active

$229,900

4 bd · 2 ba · 1,905 sqft

54 Burton Avenue, Winchester, KY

W Patrick Arvin · Keller Williams Commonwealth

New28Active

$415,000

3 bd · 3 ba · 2,270 sqft

301 Baker Court, Winchester, KY

Tracey Goebel · Tom Goebel & Company

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced32Active

$295,000

4 bd · 3 ba · 2,310 sqft

38 N Burns Avenue Street, Winchester, KY

Trina Penn · RE/MAX Creative Realty

New105Active

$645,000

6 bd · 5 ba · 5,124 sqft

124 Gadwall Lane, Winchester, KY

Lacy S Hatton · RE/MAX Elite Lexington

New7Active

$895,000

4 bd · 4 ba · 3,480 sqft

130 Duclair Drive, Winchester, KY

John L Wilson · Bluegrass Properties Group

51Active

$480,000

4 bd · 3 ba · 2,204 sqft

1924 Wades Mill Road, Winchester, KY

Kimberly B Brunson · Hunter Real Estate

Price Reduced36Active

$58,500

3 bd · 1 ba · 1,152 sqft

16 Denny Avenue, Winchester, KY

Robin Trimble · HomeFirst Real Estate

27Active

$124,000

2 bd · 1 ba · 784 sqft

356 Hill Street, Winchester, KY

Dalis Alvarez · GSP Homes

Open house Sun, Nov 15 · 2:00 PM29Active

$310,000

3 bd · 3 ba · 1,673 sqft

14 Lisle Lane, Winchester, KY

Chris B Campbell · United Real Estate Bluegrass

Price Reduced60Active

$248,900

3 bd · 1 ba · 2,249 sqft

11304 Irvine Road, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

22Active

$50,000

2 bd · 1 ba · 980 sqft

224 Wexford Drive, Winchester, KY

Danielle Despard · In House Real Estate

47Active

$365,000

3 bd · 3 ba · 2,784 sqft

735 Schollsville Road, Winchester, KY

Edgar Saborit · Lifstyl Real Estate

58Active

$439,500

3 bd · 3 ba · 2,961 sqft

42 Mockingbird Valley Road, Winchester, KY

Markus Cross · FC Tucker Bluegrass

34Active

$219,000

3 bd · 2 ba · 1,297 sqft

13 Long Avenue, Winchester, KY

Kathryn M Cheuvront · Coldwell Banker McMahan

60Active

$540,000

5 bd · 3 ba · 3,488 sqft

843 Ford Hampton Road, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced68Active

$2,500,000

8 bd · 8 ba · 13,433 sqft

4664 Lexington Road, Winchester, KY

Adam Boardman · Block + Lot Homes

26Active

$249,900

3 bd · 2 ba · 1,492 sqft

317 Vanover Way, Winchester, KY

Austina Bruton · Rector Hayden Realtors

50Active

$380,000

3 bd · 2 ba · 1,922 sqft

31 Casa Landa Way, Winchester, KY

Christine E McDonald · FC Tucker Bluegrass

Price Reduced40Active

$560,000

3 bd · 2 ba · 1,878 sqft

1515 Sewell Shop Road, Winchester, KY

Jason Townsend · Kentucky Residential Real Estate, LLC

51Active

$165,000

2 bd · 2 ba · 1,537 sqft

1494 Amster Grove Road, Winchester, KY

Libby VanMeter · Keller Williams Legacy Group

103Active

$525,000

6 bd · 5 ba · 5,552 sqft

705 W Lexington Avenue, Winchester, KY

Richard E Rogers · Rogers Realty, LLC

27Active

$260,000

3 bd · 2 ba · 1,500 sqft

103 Southern Court, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced13Active

$192,400

3 bd · 1 ba · 1,272 sqft

520 College Street, Winchester, KY

Chelsea Morguson · McCallie Real Estate

1 2…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
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By bedrooms

3 Bedroom Homes

Nearby areas

ZIP codes

40475 (297)
40509 (157)
40356 (138)
40324 (129)
40391 (112)
40515 (109)
40353 (90)
40511 (87)

Cities

Lexington (780)
Richmond (297)
Nicholasville (138)
Georgetown (129)
Mount Sterling (89)
Paris (54)
Irvine (43)
Stanton (32)

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 (297)
40509 (157)
40356 (138)
40324 (129)
40391 (112)
40515 (109)
40353 (90)
40511 (87)

Cities

Lexington (780)
Richmond (297)
Nicholasville (138)
Georgetown (129)
Mount Sterling (89)
Paris (54)
Irvine (43)
Stanton (32)

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.