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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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Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

3 Bedroom Homes in Winchester, KY

64 listings

3 Bedroom Homes in Winchester, KY

3 Bedroom Homes in Winchester, KY

24 of 64 Listings

3 Bedroom Homes in Winchester, KY

24 of 64 Listings

New45

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

Active

$299,900

3 bd · 2 ba · 1,444 sqft

8 Monroe Avenue, Winchester, KY

Robyn R Bradley · Woods Realty Group

Open house Sun, Oct 4 · 2:00 PM65Active

$769,900

3 bd · 3 ba · 2,200 sqft

330 Spencer Lane, Winchester, KY

Libby VanMeter · Marshall Lane Real Estate - Lexington

Price Reduced47Active

$445,500

3 bd · 3 ba · 2,961 sqft

42 Mockingbird Valley Road, Winchester, KY

Markus Cross · McCallie Real Estate

Price Reduced18Active

$169,000

3 bd · 1 ba · 1,046 sqft

175 Magnolia Street, Winchester, KY

A. Rebecca Woods · Woods Realty Group

$285,000

3 bd · 2 ba · 1,780 sqft

19 Victory Avenue, Winchester, KY

Daniel Poe · Re/Max Creative Realty - Mountain Legacy Group

$204,900

3 bd · 1 ba · 1,128 sqft

38 MacKay Avenue, Winchester, KY

Nena Honaker · Tom Goebel & Company

$1,125,000

3 bd · 4 ba · 3,672 sqft

2100 Irvine Road 40391, Winchester, KY

Lucy Martin Jenkins · United Real Estate Bluegrass

Open house Wed, Oct 7 · 12:00 PM34Active

$225,000

3 bd · 1 ba · 2,244 sqft

326 W Lexington Avenue, Winchester, KY

Jonathan Noel · Noel Auctioneers and Real Estate Advisors

Price Reduced46Active

$229,000

3 bd · 1 ba · 1,050 sqft

30 Virginia Avenue, Winchester, KY

Brenda H Sipes · WEICHERT REALTORS - ABG Properties

$215,000

3 bd · 1 ba · 1,134 sqft

14 Shelley Drive, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

$225,000

3 bd · 2 ba · 1,737 sqft

600 College Street, Winchester, KY

Ally Robertson · The Brokerage

$5,495,000

3 bd · 4 ba · 5,800 sqft

5825 Combs Ferry Road, Winchester, KY

Mike J Morrison · Bluegrass Sotheby's International Realty

$304,900

3 bd · 3 ba · 1,904 sqft

335 Newcastle Lane, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

$243,500

3 bd · 3 ba · 1,856 sqft

102 Quail Ridge Road, Winchester, KY

Tracey Goebel · Tom Goebel & Company

$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

$1,500,000

3 bd · 2 ba · 1,860 sqft

4578 Combs Ferry Road, Winchester, KY

Joshua A Davis · The Agency

$225,000

3 bd · 3 ba · 1,522 sqft

115 Quail Ridge Road, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

$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 Reduced29Active

$139,000

3 bd · 1 ba · 1,842 sqft

5 S Burns Avenue, Winchester, KY

Tirza Howard · The Howard Realty Co

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

$350,000

3 bd · 3 ba · 2,592 sqft

135 E Broadway Street, Winchester, KY

Dale Hatton · Dream Maker Realty, LLC

1 2 3

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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.

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Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #221881

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.