4 Bedroom Homes in Winchester, KY

Save search

3 beds New construction With a pool

Hide Map

24 Listings

Map

4 Bedroom Homes in Winchester, KY

24 Listings

23

24 listings

4 Bedroom Homes in Winchester, KY

Hide Map

24 Listings

Map

4 Bedroom Homes in Winchester, KY

24 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

23

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$225,000

4 bd · 2 ba · 1,400 sqft

522 Acadia Way, Winchester, KY

Tyler I Back · The Brokerage

46Active

$1,400,000

4 bd · 4 ba · 5,613 sqft

1400 Craig Crossing, Winchester, KY

Ken Ritter · Coldwell Banker McMahan

Price Reduced27Active

$280,000

4 bd · 2 ba · 1,752 sqft

198 Hilltop Drive, Winchester, KY

Stephanie Hacker · Kentucky Residential Real Estate, LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced12Active

$250,000

4 bd · 2 ba · 1,996 sqft

59 Hillcrest Drive, Winchester, KY

Dylan Langdon · The Agency

47Active

$484,900

4 bd · 3 ba · 2,381 sqft

410 Fairholme Way, Winchester, KY

Morgan Withrow · The Brokerage

74Active

$489,000

4 bd · 4 ba · 3,584 sqft

1137 Lafayette Boulevard, Winchester, KY

Brittany Nester · RO&CO Real Estate

110Active

$724,889

4 bd · 5 ba · 4,255 sqft

132 Lana Lane, Winchester, KY

Rebecca J Harvey · Napier Realtors

40Active

$410,000

4 bd · 2 ba · 2,435 sqft

406 Lynnway Drive, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

31Active

$300,000

4 bd · 2 ba · 2,479 sqft

224 W Hickman Street, Winchester, KY

Bob Sophiea · eXp Realty, LLC

Price Reduced40Active

$295,000

4 bd · 3 ba · 1,970 sqft

428 Waycross Drive, Winchester, KY

Wayne Elkins · RE/MAX Creative Realty

Price Reduced55Active

$395,000

4 bd · 2 ba · 3,306 sqft

351 Boone Avenue, Winchester, KY

James Woodrum · RE/MAX Creative, Winchester

Price Reduced41Active

$225,000

4 bd · 1 ba · 1,609 sqft

120 Windsor Drive, Winchester, KY

Cathie Witt-Pyle · Keller Williams Commonwealth

Price Reduced64Active

$379,000

4 bd · 3 ba · 1,978 sqft

107 Hibiscus Lane, Winchester, KY

Christa Joynt · Keller Williams Commonwealth

Price Reduced30Active

$299,900

4 bd · 3 ba · 1,840 sqft

209 Connie Lane, Winchester, KY

Mila J Ensor · Ensor Real Estate, LLC

Price Reduced36Active

$519,900

4 bd · 5 ba · 4,173 sqft

600 Boone Avenue, Winchester, KY

Holly L Goeing · The Agency

3Active

$645,000

4 bd · 3 ba · 2,526 sqft

106 Bella Shae Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

4Active

$635,000

4 bd · 3 ba · 2,537 sqft

422 Alexis Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

9Active

$785,000

4 bd · 3 ba · 2,476 sqft

425 Alexis Way, Winchester, KY

Shane T Underwood · Keller Williams Commonwealth

59Active

$499,900

4 bd · 3 ba · 5,646 sqft

16 Manor Drive, Winchester, KY

Zella B Rosenthal · Tom Goebel & Company

Price Reduced32Active

$320,000

4 bd · 3 ba · 2,310 sqft

38 N Burns Avenue Street, Winchester, KY

Trina Penn · RE/MAX Creative Realty

Price Reduced14Active

$165,000

4 bd · 3 ba · 3,462 sqft

229 S Highland Street, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced57Active

$340,000

4 bd · 2 ba · 3,261 sqft

443 S Maple Street, Winchester, KY

Terra Long · Keller Williams Commonwealth

Price Reduced84Active

$649,000

4 bd · 3 ba · 4,928 sqft

186 Chardonnay Court, Winchester, KY

Brenda H Sipes · WEICHERT REALTORS - ABG Properties

Price Reduced50Active

$419,900

4 bd · 3 ba · 1,500 sqft

240 Athens Boonesboro Road, Winchester, KY

Darrell Tackett · Dream Maker Realty, 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

July 2026 · This period is still settling

Selling at 99.6% of asking price

Sales here are closing essentially at asking. MLS · 50 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 14, 2026

Median sale price: $241,250$196,175–$368,750 typical range
Price per sq. ft.: $160
Sales: 28
Paid in cash: 57.1%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $319,900
Homes for sale: 113

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

Year-over-year: -3.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 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

July 2026 · This period is still settling

Selling at 99.6% of asking price

Sales here are closing essentially at asking. MLS · 50 sales · as of Jul 31, 2026

Homes that sold · County records, as of Jul 14, 2026

Median sale price: $241,250$196,175–$368,750 typical range
Price per sq. ft.: $160
Sales: 28
Paid in cash: 57.1%

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $319,900
Homes for sale: 113

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

Year-over-year: -3.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 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 Jul 14, 2026

Homes on the market · MLS, as of Jul 21, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 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 Jul 14, 2026

Homes on the market · MLS, as of Jul 21, 2026

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026