Homes with Pools for Sale in Winchester, KY

202 homes

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NEW 24 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to settle in on a cold winter evening. The kitchen features stainless appliances including a double wall oven, ample cabinetry and abundant lighting with plenty of counterspace for cooking your favorite meals. In the primary bedroom is a cedar lined walk-in closet and a spacious and handicap accessible b

$349,900

3 beds3 baths2,821 sq ft

3622 Stamper Dr, Winchester, KY 40391

Double wall oven • Brick fireplace • Second kitchen

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
First time offered - in the same family since 1803! This 150-acre Clark County cattle farm is a rare blend of history, natural beauty, and potential. Fully fenced with an automatic watering system, four barns, two storage sheds, four ponds and a creek, this property is ready for livestock, agriculture, or outdoor pursuits. Two home sit on the property: a 2322 Sq. Ft. ranch with a 1371 Sq. Ft finished basement with 3 kitchens! Currently used used for short term rental income and a 1764 sq. ft. farmhouse. Both are well maintained but offer an opportunity for updating, adding your personal style while leveraging the farm's functionality and income potential

$3,100,000

3 beds3 baths3,693 sq ft

3049 Ironworks Rd, Winchester, KY 40391

Four barns • Fully fenced • 150 acre cattle farm

$248,000

3 beds2.5 baths1,342 sq ft

120 Jackson St, Winchester, KY 40391

Convenient locations • Thoughtful upgrades • 6,055 sq ft lot

OPEN SUN, 1PM TO 3PM3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
Welcome to this beautifully maintained 3-bedroom, 1-bath ranch offering 1,188 sqft of classic charm on a spacious 0.26-acre lot! This home blends timeless character with thoughtful updates, featuring an inviting single-level layout, bright living areas, well-sized bedrooms, and an updated kitchen with an added pantry for extra storage. Out back, enjoy an attached and enclosed sunroom perfect for morning coffee or year-round relaxation, along with a newly added patio ideal for stringing café lights, hosting gatherings, or enjoying warm summer nights around a cozy campfire. With charming curb appeal, expanded functional spaces, and a yard full of possibilities, this ranch-style gem is

$229,000

3 beds1 bath1,188 sq ft

314 E Broadway St, Winchester, KY 40391

Spacious lot • Updated kitchen • Newly added patio

NEW 29 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Winchester, KY:
Welcome to this beautiful Craftsman style house on a very large lot, with a beautiful backyard. The newly finished stunning original hardwood floors invite you into the living room and family/dining room. There are two functioning wood burning fireplaces one in the family/dining room and another one in the kitchen. The kitchen is updated with a large island, granite counter tops, stainless steel appliances and newer cabinets. In the first floor primary bedroom you have a walk in closet. The primary bath is updated with a walk in tile shower. The laundry area is around the corner and also has a pantry area. Upstairs are two large bedrooms and a full bath. There is an additional bonus room up

$318,000

3 beds2 baths1,913 sq ft

22 N Bloomfield Rd, Winchester, KY 40391

Large lot • Large island • Updated kitchen

Property at 117 Buffalo Trce, Winchester, KY 40391, 3 beds, 2 baths

$199,900

3 beds2 baths1,072 sq ft

117 Buffalo Trce, Winchester, KY 40391

Property at 443 Jameson Way, Winchester, KY 40391, 4 beds, 2 baths

$225,000

4 beds2 baths1,400 sq ft

443 Jameson Way, Winchester, KY 40391

Property at 19 Cherokee Ct, Winchester, KY 40391, 3 beds, 1 bath

$224,900

3 beds1 bath1,134 sq ft

19 Cherokee Ct, Winchester, KY 40391

Property at 208 Watercrest Way, Winchester, KY 40391, 3 beds, 2.5 baths

$255,000

3 beds2.5 baths1,416 sq ft

208 Watercrest Way, Winchester, KY 40391

Property at 6504 Combs Ferry Rd, Winchester, KY 40391, 5 beds, 3.5 baths

$425,000

5 beds3.5 baths2,564 sq ft

6504 Combs Ferry Rd, Winchester, KY 40391

Property at 670 Lillies Ferry Rd, Winchester, KY 40391, 3 beds, 2 baths

$489,000

3 beds2 baths2,053 sq ft

670 Lillies Ferry Rd, Winchester, KY 40391

Property at 1857 Ironworks Rd, Winchester, KY 40391, 5 beds, 2.5 baths

$420,000

5 beds2.5 baths2,924 sq ft

1857 Ironworks Rd, Winchester, KY 40391

Property at 214 S Burns Ave, Winchester, KY 40391, 4 beds, 1.5 baths

$318,500

4 beds1.5 baths2,170 sq ft

214 S Burns Ave, Winchester, KY 40391

Property at 246 Geronimo Ct, Winchester, KY 40391, 3 beds, 2 baths

$210,000

3 beds2 baths1,092 sq ft

246 Geronimo Ct, Winchester, KY 40391

Property at 41 7th St, Winchester, KY 40391, 3 beds, 2 baths

$190,000

3 beds2 baths1,116 sq ft

41 7th St, Winchester, KY 40391

Property at 595 Earlymeade Dr, Winchester, KY 40391, 5 beds, 3.5 baths

$499,000

5 beds3.5 baths3,823 sq ft

595 Earlymeade Dr, Winchester, KY 40391

Property at 205 E Washington St, Winchester, KY 40391, 4 beds, 2.5 baths

$130,000

4 beds2.5 baths2,131 sq ft

205 E Washington St, Winchester, KY 40391

Property at 357 Crescent Ave, Winchester, KY 40391, 3 beds, 1.5 baths

$255,000

3 beds1.5 baths2,188 sq ft

357 Crescent Ave, Winchester, KY 40391

Property at 1503 Schollsville Rd, Winchester, KY 40391, 5 beds, 3 baths

$475,000

5 beds3 baths3,718 sq ft

1503 Schollsville Rd, Winchester, KY 40391

Property at 4074 Ironworks Rd, Winchester, KY 40391, 3 beds, 1.5 baths

$309,000

3 beds1.5 baths1,356 sq ft

4074 Ironworks Rd, Winchester, KY 40391

Property at 3208 Ford Hampton Rd, Winchester, KY 40391, 2 beds, 1 bath

$147,000

2 beds1 bath807 sq ft

3208 Ford Hampton Rd, Winchester, KY 40391

Property at 21 Virginia Ave, Winchester, KY 40391, 3 beds, 2 baths

$260,000

3 beds2 baths1,749 sq ft

21 Virginia Ave, Winchester, KY 40391

Property at 6239 Old Boonesboro Rd, Winchester, KY 40391, 4 beds, 2 baths

$399,000

4 beds2 baths2,659 sq ft

6239 Old Boonesboro Rd, Winchester, KY 40391

Property at 114 Magnolia St, Winchester, KY 40391, 2 beds, 1 bath

$115,000

2 beds1 bath910 sq ft

114 Magnolia St, Winchester, KY 40391

Property at 720 Estes Dr, Winchester, KY 40391, 3 beds, 1 bath

$249,900

3 beds1 bath1,494 sq ft

720 Estes Dr, Winchester, KY 40391

Property at 101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391, 8 beds, 4 baths

$675,000

8 beds4 baths5,046 sq ft

101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

Property at 12 Linden Ave, Winchester, KY 40391, 3 beds, 2 baths

$240,000

3 beds2 baths— sq ft

12 Linden Ave, Winchester, KY 40391

Property at 245 Ecton Rd, Winchester, KY 40391, 3 beds, 1 bath

$209,900

3 beds1 bath1,074 sq ft

245 Ecton Rd, Winchester, KY 40391

Property at 3166 Colby Rd, Winchester, KY 40391, 3 beds, 2.5 baths

$1,889,000

3 beds2.5 baths4,518 sq ft

3166 Colby Rd, Winchester, KY 40391

Property at 8 Village Dr, Winchester, KY 40391, 3 beds, 2 baths

$295,000

3 beds2 baths1,979 sq ft

8 Village Dr, Winchester, KY 40391

Property at 5039 Combs Ferry Rd, Winchester, KY 40391, 5 beds, 4 baths

$2,495,000

5 beds4 baths6,284 sq ft

5039 Combs Ferry Rd, Winchester, KY 40391

Property at 174 Hidden Grove Ln, Winchester, KY 40391, 2 beds, 2 baths

$265,000

2 beds2 baths1,521 sq ft

174 Hidden Grove Ln, Winchester, KY 40391

Property at 414 Fairholme Way, Winchester, KY 40391, 4 beds, 3 baths

$499,900

4 beds3 baths2,300 sq ft

414 Fairholme Way, Winchester, KY 40391

Property at 221 S Highland St, Winchester, KY 40391, 5 beds, 3 baths

$257,500

5 beds3 baths3,007 sq ft

221 S Highland St, Winchester, KY 40391

Property at 222 Bracken Ct, Winchester, KY 40391, 3 beds, 2.5 baths

$269,000

3 beds2.5 baths1,456 sq ft

222 Bracken Ct, Winchester, KY 40391

Property at 225 Plantations Dr, Winchester, KY 40391, 3 beds, 2.5 baths

$364,900

3 beds2.5 baths3,868 sq ft

225 Plantations Dr, Winchester, KY 40391

Property at 729 Wayland Dr, Winchester, KY 40391, 3 beds, 2 baths

$289,000

3 beds2 baths1,966 sq ft

729 Wayland Dr, Winchester, KY 40391

Property at 146 Cook Ave, Winchester, KY 40391, 3 beds, 1 bath

$167,500

3 beds1 bath1,274 sq ft

146 Cook Ave, Winchester, KY 40391

Property at 300 Calmes Blvd, Winchester, KY 40391, 3 beds, 2.5 baths

$379,717

3 beds2.5 baths2,636 sq ft

300 Calmes Blvd, Winchester, KY 40391

Property at 1410 Dry Fork Creek Rd, Winchester, KY 40391, 3 beds, 2 baths

$485,000

3 beds2 baths1,064 sq ft

1410 Dry Fork Creek Rd, Winchester, KY 40391

Property at 1783 Gay Evans Rd, Winchester, KY 40391, 5 beds, 3.5 baths

$775,000

5 beds3.5 baths2,904 sq ft

1783 Gay Evans Rd, Winchester, KY 40391

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Homes with Pools for Sale in Winchester

There are currently 202 homes with pools for sale in Winchester at a median listing price of $259K. 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 70 days. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 19 homes have been sold in Winchester. In addition to houses in Winchester, there were also 0 condos, 4 townhouses, and 4 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.

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