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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 114 Listings

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24 of 114 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

New26Active
$215,000
3 bd · 1 ba · 1,134 sqft
14 Shelley Drive, Winchester, KY
Michelle R Blackburn · RE/MAX Creative, Winchester
29Active
$225,000
3 bd · 2 ba · 1,737 sqft
600 College Street, Winchester, KY
Ally Robertson · The Brokerage
Price Reduced21Active
$99,500
2 bd · 2 ba · 924 sqft
563 Constitution Drive, Winchester, KY
Jason Townsend · Kentucky Residential Real Estate, LLC

New54Active
$375,000
4 bd · 2 ba · 1,828 sqft
609 W Barlow Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
66Active
$775,000
6 bd · 4 ba · 3,789 sqft
1255 The Ridings, Winchester, KY
Lucy Martin Jenkins · United Real Estate Bluegrass
90Active
$5,495,000
3 bd · 4 ba · 5,800 sqft
5825 Combs Ferry Road, Winchester, KY
Mike J Morrison · Bluegrass Sotheby's International Realty
48Active
$304,900
3 bd · 3 ba · 1,904 sqft
335 Newcastle Lane, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
94Active
$675,000
4 bd · 4 ba · 2,659 sqft
1477 Sewell Shop Road, Winchester, KY
Jason Townsend · Kentucky Residential Real Estate, LLC
22Active
$243,500
3 bd · 3 ba · 1,856 sqft
102 Quail Ridge Road, Winchester, KY
Tracey Goebel · Tom Goebel & Company
27Active
$125,000
1 bd · 1 ba · 779 sqft
6590 Ironworks Road, Winchester, KY
Susan Baldwin · Threshold Real Estate Services
46Active
$475,000
3 bd · 2 ba · 2,174 sqft
625 Pine Ridge Road, Winchester, KY
Tonya Morrow · KY Local
Price Reduced37Active
$249,000
3 bd · 2 ba · 1,386 sqft
33 Bon-Haven Avenue, Winchester, KY
Erika Beatty · Plum Tree Realty
48Active
$1,500,000
3 bd · 2 ba · 1,860 sqft
4578 Combs Ferry Road, Winchester, KY
Joshua A Davis · The Agency
43Active
$319,900
4 bd · 2 ba · 1,953 sqft
6 French Avenue, Winchester, KY
A. Rebecca Woods · Woods Realty Group
Price Reduced58Active
$74,950
2 bd · 1 ba · 825 sqft
1860 Ford Road, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC
Price Reduced50Active
$419,900
4 bd · 3 ba · 1,500 sqft
240 Athens Boonesboro Road, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC
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 Reduced4Active
$155,000
2 bd · 1 ba · 1,472 sqft
13 Maryland Avenue, Winchester, KY
Clay David Sutherland · ERA Select Real Estate
33Active
$225,000
3 bd · 3 ba · 1,522 sqft
115 Quail Ridge Road, Winchester, KY
Michelle R Blackburn · RE/MAX Creative, Winchester
26Active
$249,900
3 bd · 2 ba · 1,492 sqft
317 Vanover Way, Winchester, KY
Austina Bruton · Rector Hayden Realtors
Price Reduced29Active
$275,000
3 bd · 2 ba · 1,500 sqft
103 Southern Court, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
40Active
$498,000
4 bd · 3 ba · 2,496 sqft
1780 Stoner-Ephesus Road, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC
29Active
$150,000
3 bd · 1 ba · 1,842 sqft
5 S Burns Avenue, Winchester, KY
Tirza Howard · The Howard Realty Co

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

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 (274)
40509 (156)
40356 (138)
40324 (131)
40391 (114)
40515 (110)
40511 (80)
40353 (74)

Cities

Lexington (789)
Richmond (274)
Nicholasville (138)
Georgetown (131)
Mt Sterling (73)
Paris (44)
Stanton (37)
Carlisle (27)

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

Nearby areas

ZIP codes

40475 (274)
40509 (156)
40356 (138)
40324 (131)
40391 (114)
40515 (110)
40511 (80)
40353 (74)

Cities

Lexington (789)
Richmond (274)
Nicholasville (138)
Georgetown (131)
Mt Sterling (73)
Paris (44)
Stanton (37)
Carlisle (27)

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.