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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Rentals
Commercial

118 listings

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118 listings

Homes for Sale in Winchester, KY

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24 of 118 Listings

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24 of 118 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced35

Active

$299,900

5 bd · 2 ba · 2,082 sqft

128 Cherokee Drive, Winchester, KY

Tyler A Hurst · Oak & Acre

New38Active

$519,900

5 bd · 3 ba · 2,200 sqft

7440 Bybee Road, Winchester, KY

Jessica Pelfrey · WEICHERT REALTORS - Ford Brothers

New22Active

$280,000

4 bd · 3 ba · 1,967 sqft

127 Lindberg Avenue, Winchester, KY

Wayne Elkins · RE/MAX Creative Realty

64Active

$439,900

3 bd · 2 ba · 2,276 sqft

119 Winterberry Circle, Winchester, KY

Courtney Ann Mangold · The Agency

Price Reduced25Active

$219,900

3 bd · 2 ba · 1,904 sqft

528 Estes Drive, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

38Active

$299,900

3 bd · 2 ba · 1,648 sqft

314 Botts Court, Winchester, KY

Edgar Saborit · Lifstyl Real Estate

Price ReducedActive

$255,000

3 bd · 3 ba · 2,260 sqft

209 Boone Avenue, Winchester, KY

Todd Hyatt · Lois Ann Disponett Real Est

Price ReducedActive

$155,900

1 bd · 2 ba · 1,056 sqft

101 Alabama Street, Winchester, KY

A. Rebecca Woods · Woods Realty Group

58Active

$484,900

4 bd · 3 ba · 2,381 sqft

410 Fairholme Way, Winchester, KY

Morgan Withrow · The Brokerage

6Active

$462,738

3 bd · 2 ba · 1,806 sqft

230 Evergreen Drive, Winchester, KY

Rex Hall · United Real Estate Bluegrass

6Active

$457,900

4 bd · 3 ba · 1,986 sqft

200 Evergreen Drive, Winchester, KY

Rex Hall · United Real Estate Bluegrass

6Active

$469,925

3 bd · 2 ba · 1,855 sqft

225 Evergreen Drive, Winchester, KY

Rex Hall · United Real Estate Bluegrass

54Active

$250,000

3 bd · 2 ba · 1,893 sqft

13 Euclid Avenue, Winchester, KY

Robin S Jones · Keller Williams Legacy Group

6Active

$513,600

3 bd · 2 ba · 2,268 sqft

220 Evergreen Drive, Winchester, KY

Rex Hall · United Real Estate Bluegrass

22Active

$617,000

3 bd · 4 ba · 4,848 sqft

131 Teal Lane, Winchester, KY

Rony Jo Ballou · Power House Realty

38Active

$424,500

5 bd · 4 ba · 3,674 sqft

323 Skylark Drive, Winchester, KY

Tracey Goebel · Tom Goebel & Company

Price ReducedActive

$325,000

4 bd · 2 ba · 3,261 sqft

443 S Maple Street, Winchester, KY

Terra Long · Keller Williams Commonwealth

46Active

$325,000

5 bd · 3 ba · 3,378 sqft

25 W Hickman Street, Winchester, KY

Christina Bucher · Keller Williams Legacy Group

Price Reduced21Active

$99,500

2 bd · 2 ba · 924 sqft

563 Constitution Drive, Winchester, KY

Jason Townsend · Kentucky Residential Real Estate, LLC

Open house Sun, Oct 25 · 2:00 PM45Active

$279,900

3 bd · 3 ba · 2,779 sqft

121 Bay Hill Drive, Winchester, KY

Kimberly C Dice · eXp Realty, LLC

60Active

$255,000

3 bd · 1 ba · 1,135 sqft

26 Holiday Road, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

29Active

$221,000

3 bd · 2 ba · 1,665 sqft

106 Quail Ridge Road, Winchester, KY

Mila J Ensor · Ensor Real Estate, LLC

23Active

$199,500

3 bd · 1 ba · 1,193 sqft

214 Center Drive, Winchester, KY

Lukas Owens · The Brokerage

90Active

$4,895,000

3 bd · 4 ba · 5,800 sqft

5825 Combs Ferry Road, Winchester, KY

Mike J Morrison · Bluegrass Sotheby's International Realty

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

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 (298)
40509 (153)
40391 (118)
40515 (109)
40324 (97)
40356 (89)
40353 (88)
40511 (86)

Cities

Lexington (784)
Richmond (298)
Georgetown (97)
Nicholasville (89)
Mount Sterling

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

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 (298)
40509 (153)
40391 (118)
40515 (109)
40324 (97)
40356 (89)
40353 (88)
40511 (86)

Cities

Lexington (784)
Richmond (298)
Georgetown (97)
Nicholasville (89)
Mount Sterling

(87)

Paris (54)

Irvine (34)

Stanton (32)

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, 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.

Winchester, KY Homes for Sale | Realty.com