Winchester, KY homes for sale & real estate

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NEW 9 HRS AGO

ABOUT THIS HOME
Winchester, KY Homes for Sale
Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 21' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living space is a walk out basement with 8" poured concrete walls. 10'6" ceilings and 9 windows maintaining an airy, open space with plenty of natural lighting. Recessed LED ceiling lighting, full cat-6 wiring and knotty pine decorative doors installed in below grade area. Highlight is the 9'x14' ba

$384,900

4 beds4.5 baths— sq ft

3600 Crowe Ridge Rd, Winchester, KY 40391

2 laundry rooms • 2 kitchens • Panoramic views

NEW 14 HRS AGO

ABOUT THIS HOME
Winchester, KY Homes for Sale
Welcome to your next home in one of Clark County's most desirable neighborhoods—Shala Mar Estates! This beautifully updated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and modern convenience. Step into the expansive primary bedroom, a true retreat, complete with a stunning ensuite bathroom featuring a brand-new soaking tub and a separate tiled shower. The additional bedrooms are spacious and versatile, ideal for family, guests, or a home office. The heart of the home is the massive gourmet kitchen, showcasing new granite countertops, all-new stainless steel appliances, and a charming built-in coffee bar—perfect for slow mornings or entertaining guests.

$379,000

3 beds2 baths2,000 sq ft

133 Shala-mar Rue, Winchester, KY 40391

Soaking tub • Gourmet kitchen • Granite countertops

ABOUT THIS HOME
Winchester, KY Homes for Sale
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
Winchester, KY Homes for Sale
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

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 22 N Bloomfield Rd, Winchester, KY 40391, 3 beds, 2 baths

$318,000

3 beds2 baths1,913 sq ft

22 N Bloomfield Rd, 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 314 E Broadway St, Winchester, KY 40391, 3 beds, 1 bath

$229,000

3 beds1 bath1,188 sq ft

314 E Broadway St, 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 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 205 E Washington St, Winchester, KY 40391, 4 beds, 2.5 baths

$124,900

4 beds2.5 baths2,131 sq ft

205 E Washington 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 729 Wayland Dr, Winchester, KY 40391, 3 beds, 2 baths

$284,000

3 beds2 baths1,966 sq ft

729 Wayland Dr, 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 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

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Average home prices near Winchester, KY

Cities

Lexington homes for sale
$359,900
North Middletown homes for sale
$204,000
Richmond homes for sale
$315,000
Stanton homes for sale
$215,000
Clay City homes for sale
$159,500
Millersburg homes for sale
$179,900
Mount Sterling homes for sale
$300,000
Lexington-Fayette homes for sale
$359,900
Camargo homes for sale
$229,000
Paris homes for sale
$277,000
Sharpsburg homes for sale
$204,900

Zip Codes

40391 homes for sale
$319,900

Winchester, KY real estate trends

All Home Types trends in Winchester, KY

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$270,000

+21.3% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Winchester, KY

$270,000

+21.3%

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