Homes with Pools for Sale in Winchester, KY

198 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

$110,000

— beds— baths— sq ft

1185 Craig Crossing Rd, Winchester, KY 40391

2.06 acre lot • Listed 1112 days

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

$150,000

— beds— baths— sq ft

125 Knox Ct, Winchester, KY 40391

2.11 acre lot • Listed 1122 days

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

$150,000

— beds— baths— sq ft

120 Knox Ct, Winchester, KY 40391

2.16 acre lot • Listed 1122 days

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms. The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite bathroom. The kitchen includes a convenient pantry and flows seamlessly into the living and dining areas, ideal for entertaining or everyday comfort. A separate utility room adds extra functionality, and the 2-car garage provides ample storage. Enjoy the outdoors from the inviting front porch or take advan

$380,000

3 beds2 baths1,677 sq ft

230 Evergreen Dr, Winchester, KY 40391

Walk-in closet • Convenient pantry • Ensuite bathroom

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks road and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center Drive and near large sign. For more information, give us a call!

$799,900

— beds— baths— sq ft

1600 Ironworks Rd, Winchester, KY 40391

13.19 acre lot • Listed 266 days

Property at 529 Bullion Blvd Unit 3B, Winchester, KY 40391

$775,000

— beds— baths— sq ft

529 Bullion Blvd Unit 3B, Winchester, KY 40391

Property at 205 Codella Dr, Winchester, KY 40391

$650,000

— beds— baths— sq ft

205 Codella Dr, Winchester, KY 40391

Property at 800 Interstate Dr, Winchester, KY 40391

$270,000

— beds— baths— sq ft

800 Interstate Dr, Winchester, KY 40391

Property at 145 Codella Dr, Winchester, KY 40391

$400,000

— beds— baths— sq ft

145 Codella Dr, Winchester, KY 40391

Property at 529 Bullion Blvd Unit 3A, Winchester, KY 40391

$775,000

— beds— baths— sq ft

529 Bullion Blvd Unit 3A, Winchester, KY 40391

Property at 155 April Way, Winchester, KY 40391

$1,350,000

— beds— baths— sq ft

155 April Way, Winchester, KY 40391

Property at 130 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

130 Duclair Dr, Winchester, KY 40391

Property at 150 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

150 Duclair Dr, Winchester, KY 40391

Property at 100 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

100 Duclair Dr, Winchester, KY 40391

Property at 160 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

160 Duclair Dr, Winchester, KY 40391

Property at 120 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

120 Duclair Dr, Winchester, KY 40391

Property at 200 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

200 Duclair Dr, Winchester, KY 40391

Property at 230 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

230 Duclair Dr, Winchester, KY 40391

Property at 255 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

255 Duclair Dr, Winchester, KY 40391

Property at 139 Jacob Ct, Winchester, KY 40391

$110,000

— beds— baths— sq ft

139 Jacob Ct, Winchester, KY 40391

Property at 260 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

260 Duclair Dr, Winchester, KY 40391

Property at 250 Duclair Dr, Winchester, KY 40391

$110,000

— beds— baths— sq ft

250 Duclair Dr, Winchester, KY 40391

Property at 270 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

270 Duclair Dr, Winchester, KY 40391

Property at 135 Jacob Ct, Winchester, KY 40391

$110,000

— beds— baths— sq ft

135 Jacob Ct, Winchester, KY 40391

Property at 125 Jacob Ct, Winchester, KY 40391

$110,000

— beds— baths— sq ft

125 Jacob Ct, Winchester, KY 40391

Property at 115 Jacob Ct, Winchester, KY 40391

$110,000

— beds— baths— sq ft

115 Jacob Ct, Winchester, KY 40391

Property at 225 Jacob Ct, Winchester, KY 40391

$100,000

— beds— baths— sq ft

225 Jacob Ct, Winchester, KY 40391

Property at 165 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

165 Duclair Dr, Winchester, KY 40391

Property at 155 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

155 Duclair Dr, Winchester, KY 40391

Property at 111 Jacob Ct, Winchester, KY 40391

$100,000

— beds— baths— sq ft

111 Jacob Ct, Winchester, KY 40391

Property at 215 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

215 Duclair Dr, Winchester, KY 40391

Property at 169 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

169 Duclair Dr, Winchester, KY 40391

Property at 129 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

129 Duclair Dr, Winchester, KY 40391

Property at 115 Duclair Dr, Winchester, KY 40391

$100,000

— beds— baths— sq ft

115 Duclair Dr, Winchester, KY 40391

Viewing page 5 of 5

Homes with Pools for Sale in Winchester

There are currently 198 homes with pools for sale in Winchester at a median listing price of $265K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 56 days. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 17 homes have been sold in Winchester. In addition to houses in Winchester, there were also 0 condos, 4 townhouses, and 5 multi-family units for sale in Winchester last month. Winchester is a minimally walkable city in Kentucky with a Walk Score of 36. Winchester is home to approximately 17,893 people and 8,688 jobs. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. Our Winchester real estate stats and trends will give you more information about home buying and selling trends in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Winchester, KY

Zip Codes

40391 homes for sale

Nearby Cities

Nearby Cities with Homes with Pools

More to explore in Winchester, KY

How to buy a house in Winchester, KY

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Kentucky

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.