Homes Under $600K in Winchester, KY

Hide Map

24 of 92 Listings

Map

24 of 92 Listings

New32

92 listings

Homes Under $600K in Winchester, KY

Hide Map

24 of 92 Listings

Map

Homes Under $600K in Winchester, KY

24 of 92 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

New32

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$367,700

4 bd · 2 ba · 1,825 sqft

107 S Burns Avenue, Winchester, KY

Lauren Lewis · Christies International Real Estate Bluegrass

New33Active

$335,000

3 bd · 2 ba · 1,836 sqft

2550 Kiddville Road, Winchester, KY

Monique Gamble · The Real Estate Co - W Liberty

45Active

$299,900

3 bd · 2 ba · 1,444 sqft

8 Monroe Avenue, Winchester, KY

Robyn R Bradley · Woods Realty Group

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

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

Price Reduced22Active

$134,900

2 bd · 1 ba · 986 sqft

174 Cook Avenue, Winchester, KY

A. Rebecca Woods · Woods Realty Group

42Active

$285,000

3 bd · 2 ba · 1,780 sqft

19 Victory Avenue, Winchester, KY

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

23Active

$204,900

3 bd · 1 ba · 1,128 sqft

38 MacKay Avenue, Winchester, KY

Nena Honaker · Tom Goebel & Company

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

26Active

$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

54Active

$375,000

4 bd · 2 ba · 1,828 sqft

609 W Barlow Drive, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

48Active

$304,900

3 bd · 3 ba · 1,904 sqft

335 Newcastle Lane, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

22Active

$243,500

3 bd · 3 ba · 1,856 sqft

102 Quail Ridge Road, Winchester, KY

Tracey Goebel · Tom Goebel & Company

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

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

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

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.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winchester housing market

Homes that sold · County records, as of Aug 19, 2026

Homes on the market · MLS, as of Aug 30, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Winchester, KY community profile

Explore Winchester homes

Your local brokerage

Listing data & MLS disclosures

Winchester, KY community profile

Winchester housing market

Homes that sold · County records, as of Aug 19, 2026

Homes on the market · MLS, as of Aug 30, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026