5 Bedroom Homes in Winchester, KY

Show Map

8 Listings

Map

8 Listings

Price Reduced12Active

8 listings

5 Bedroom Homes in Winchester, KY

Show Map

8 Listings

Map

5 Bedroom Homes in Winchester, KY

8 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced12Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

$264,900

5 bd · 2 ba · 2,214 sqft

55 Hillcrest Drive, Winchester, KY

Nina Vanetten · RE/MAX Elite Lexington

63Active

$785,000

5 bd · 3 ba · 4,676 sqft

217 Wades Mill Road, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

50Active

$639,000

5 bd · 4 ba · 5,011 sqft

104 Teal Lane, Winchester, KY

The Gooch Team - Kristy Gooch · RE/MAX Elite Realty

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced72Active

$544,900

5 bd · 4 ba · 3,741 sqft

130 Winterberry Circle, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

82Active

$2,299,000

5 bd · 5 ba · 6,284 sqft

5039 Combs Ferry Road, Winchester, KY

Michael R Hilario · The Agency

Price Reduced35Active

$299,900

5 bd · 2 ba · 2,082 sqft

128 Cherokee Drive, Winchester, KY

Tyler A Hurst · Oak & Acre

Price Reduced30Active

$325,000

5 bd · 4 ba · 4,456 sqft

410 W Lexington Avenue, Winchester, KY

Tracy M Ison · Bluegrass Home Group

Price Reduced18Active

$490,000

5 bd · 3 ba · 3,102 sqft

110 White Conkwright Road, Winchester, KY

Philip PJ Elder · Omega Real Estate Brokerage LLC

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