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3 Bedroom Homes in Winchester, KY

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24 of 70 Listings

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24 of 70 Listings

Price Reduced29

3 Bedroom Homes in Winchester, KY — Page 2

70 listings

3 Bedroom Homes in Winchester, KY

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24 of 70 Listings

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3 Bedroom Homes in Winchester, KY

24 of 70 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced29

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$220,000

3 bd · 2 ba · 1,737 sqft

600 College Street, Winchester, KY

Ally Robertson · The Brokerage

48Active

$304,900

3 bd · 3 ba · 1,904 sqft

335 Newcastle Lane, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

Price Reduced22Active

$239,000

3 bd · 3 ba · 1,856 sqft

102 Quail Ridge Road, Winchester, KY

Tracey Goebel · Tom Goebel & Company

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

46Active

$475,000

3 bd · 2 ba · 2,174 sqft

625 Pine Ridge Road, Winchester, KY

Tonya Morrow · KY Local

48Active

$1,500,000

3 bd · 2 ba · 1,860 sqft

4578 Combs Ferry Road, Winchester, KY

Joshua A Davis · The Agency

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

Price Reduced60Active

$248,900

3 bd · 1 ba · 2,249 sqft

11304 Irvine Road, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

Price Reduced64Active

$349,900

3 bd · 3 ba · 1,846 sqft

420 Calmes Boulevard, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

19Active

$350,000

3 bd · 3 ba · 2,592 sqft

135 E Broadway Street, Winchester, KY

Dale Hatton · Dream Maker Realty, LLC

Price Reduced31Active

$275,000

3 bd · 2 ba · 1,512 sqft

4305 Old Boonesboro Road, Winchester, KY

Brenda H Sipes · WEICHERT REALTORS - ABG Properties

Price Reduced25Active

$159,000

3 bd · 1 ba · 1,249 sqft

209 E Washington Street, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced18Active

$355,000

3 bd · 2 ba · 1,990 sqft

11 Stoney Brook Drive 1, Winchester, KY

Garry H Milton · Milton and Associates Real Estate

Price Reduced60Active

$229,900

3 bd · 1 ba · 1,272 sqft

119 Tower Lane, Winchester, KY

Shawna Wever · Wever Realty LLC

40Active

$244,000

3 bd · 2 ba · 1,692 sqft

54 Locust Drive, Winchester, KY

Natalie Avant · Berkshire Hathaway HomeServices Foster Realtors

Price Reduced24Active

$219,900

3 bd · 1 ba · 1,100 sqft

125 Kittison Drive, Winchester, KY

Kathryn M Cheuvront · Coldwell Banker McMahan

65Active

$359,900

3 bd · 2 ba · 2,269 sqft

15 Moundale Avenue, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

28Active

$365,900

3 bd · 2 ba · 1,558 sqft

204 Jett Drive, Winchester, KY

Mila J Ensor · Ensor Real Estate, LLC

Price Reduced23Active

$205,000

3 bd · 2 ba · 1,319 sqft

3 Nunnelly Court, Winchester, KY

Yasir Ahmed · Black Mountain Realty

24Active

$365,900

3 bd · 2 ba · 1,635 sqft

206 Jett Drive, Winchester, KY

Mila J Ensor · Ensor Real Estate, LLC

Price Reduced32Active

$160,000

3 bd · 1 ba · 1,173 sqft

24 Spring Street, Winchester, KY

Jason L Szaks · EXIT Town & Country Realtors

Price Reduced56Active

$249,000

3 bd · 3 ba · 1,664 sqft

127 Bay Hill Drive, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

Price Reduced36Active

$78,500

3 bd · 1 ba · 1,152 sqft

16 Denny Avenue, Winchester, KY

Robin Trimble · HomeFirst Real Estate

1 2 3

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

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.

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.