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Winchester KY Homes for Sale

Displayed below, and updated from the MLS every 15 minutes, are homes for sale in Winchester, which is located in Clark County.

A quick, 20-minute drive from Lexington can find you amidst spectacular scenery in the city of Winchester. The Kentucky River and historic Howard’s Creek Nature and Heritage Preserve offer a glimpse of the natural wonder of Winchester. And a scenic walk through historic downtown Winchester shows its small-town wonder, with easy access to antique shops, locally owned restaurants, rich architecture and the Bluegrass Heritage Museum. Throughout the year, you can also enjoy annual festivals like the Daniel Boone Pioneer Festival and the Beer Cheese Festival, amongst others. Like it’s gingery soft drink – Ale-8-One – Winchester is a one-of-a-kind treasure you can only find in the Bluegrass.

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Winchester April 25, 2019
94
Listed
73
Avg. DOM
$104.90
Avg. $ / Sq.Ft.
$199,950
Med. List Price
94 Properties Found. Showing 1-12
Sort By:
430 Pretty Run Road
Winchester, KY 40391
430 Pretty Run Road Winchester, KY 40391
1 of 30
$995,000 ( $200,000 )
Subdivision: Rural
BEDS
4
BATHS
3
SQ.FT.
4,767
BUILT
1850
ON SITE
108Days
MLS
1716087
Gorgeous historic home with Clark County location, within 20 minute drive to Lexington! Situated on 15 acres surrounded by a horse farm, this home features beautiful hardwood floors, 4 bedrooms, 3...
3565 Paris Road
Winchester, KY 40391
3565 Paris Road Winchester, KY 40391
1 of 63
$985,000
Subdivision: Rural
BEDS
6
BATHS
4
SQ.FT.
7,600
BUILT
1878
ON SITE
132Days
MLS
1827554
This stately 1878 brick Victorian home, known as Rotherwood, is located in Clark County. Listed by the Heritage Council as a Kentucky Landmark, this magnificent home presides over 25 beautiful...
1080 Cole Road
Winchester, KY 40391
1080 Cole Road Winchester, KY 40391
1 of 88
$849,000
Subdivision: Rural
BEDS
3
BATHS
2
SQ.FT.
1,454
BUILT
1990
ON SITE
20Days
MLS
1906947
Bring your horses!! And your cows, goats, sheep, and alpacas! And your fishing poles, hiking boots and your 4 wheelers! No restrictions! This sprawling 242 acre completely fenced farm can be yours...
509 Combs Ferry Road
Winchester, KY 40391
509 Combs Ferry Road Winchester, KY 40391
1 of 37
$699,000
Subdivision: Rural
BEDS
4
BATHS
5
SQ.FT.
3,889
BUILT
2004
ON SITE
8Days
MLS
1906558
Country Living close to Downtown Lexington, Hamburg, Winchester and major interstates. 1-1/2 story Executive Home for rent, sale or lease,located on 5 acres. Beautifully appointed - granite counter...
390 Lillies Ferry
Winchester, KY 40391
390 Lillies Ferry Winchester, KY 40391
1 of 74
$639,000
Subdivision: Rural
BEDS
4
BATHS
3
SQ.FT.
3,618
BUILT
1995
ON SITE
42Days
MLS
1905223
Enjoy quiet country living in this modern log home that provides spectacular views at all angles. Rolling property boasts 2 ponds on the property with creek. Currently recreational us for land,...
702 S Maple
Winchester, KY 40391
702 S Maple Winchester, KY 40391
1 of 88
$529,900
Subdivision: Downtown
BEDS
5
BATHS
4
SQ.FT.
3,680
BUILT
2005
ON SITE
8Days
MLS
1907730
Location, Location, Location!! Close to downtown, bypass, and Winchester Country Club. Situated on a quiet cul-de-sac this beautiful two-story brick home with recently updated back yard oasis will...
5227 Lexington Road
Winchester, KY 40391
5227 Lexington Road Winchester, KY 40391
1 of 63
$499,000
Subdivision: Rural
BEDS
4
BATHS
5
SQ.FT.
4,049
BUILT
1981
ON SITE
233Days
MLS
1812087
This home on 4.25 acres is the perfect combination of GREAT LOCATION and GREAT LIVING SPACES INSIDE and OUT! Located just over the Clark Co line, you can be in Hamburg in less than 15 minutes and in...
108 Hidden Grove Lane
Winchester, KY 40391
108 Hidden Grove Lane Winchester, KY 40391
1 of 48
$437,500
Subdivision: Rural
BEDS
5
BATHS
4
SQ.FT.
3,763
BUILT
N/A
ON SITE
25Days
MLS
1822117
Kentucky Riverfront Retreat! Idyllic home with many upgrades and recent remodeling. 5 Bedrooms, 3 1/2 baths, custom kitchen with high grade appliances, large utility/mudroom with dog washing station....
315 The Woods
Winchester, KY 40391
315 The Woods Winchester, KY 40391
1 of 17
$431,000
Subdivision: Stoneybrook
BEDS
5
BATHS
4
SQ.FT.
3,876
BUILT
1995
ON SITE
94Days
MLS
1901406
The owner of this house custom designed and had it built. First floor master, built-ins located in bonus room bedrooms and throughout the house, 2 utility rooms, one on the first floor and one in...
3720 McClure Road
Winchester, KY 40391
3720 McClure Road Winchester, KY 40391
1 of 63
$409,900
Subdivision: Rural
BEDS
6
BATHS
3
SQ.FT.
3,850
BUILT
1970
ON SITE
1Day
MLS
1908432
You will find this house located in the heart of Kentucky Bluegrass and just minutes from the Hamburg area of Lexington. In 2017 this house had a total remodel. See the Seller's Disclosure for more...
1000 McClure Road
Winchester, KY 40391
1000 McClure Road Winchester, KY 40391
1 of 93
$399,900
Subdivision: Rural
BEDS
4
BATHS
4
SQ.FT.
4,776
BUILT
1989
ON SITE
51Days
MLS
1903975
Location, Location, Location (McClure Road) Well maintained Custom brick ranch on 5 ACRES with a oversized 2 car garage and a full finished basement with two rooms that could be bed #5 and #6 if...
1400 Gay Evans Road
Winchester, KY 40391
1400 Gay Evans Road Winchester, KY 40391
1 of 79
$399,900 ( $10,000 )
Subdivision: Rural
BEDS
5
BATHS
4
SQ.FT.
3,800
BUILT
2004
ON SITE
45Days
MLS
1904803
Detached garage/workshop! Bring your toys! Location! This home is close to I-64 and and minutes to Lexington. This brick ranch sits on roughly 3 acres in Clark County and offers 4 bedrooms on the...
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