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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 January 22, 2021
44
Listed
104
Avg. DOM
$125.05
Avg. $ / Sq.Ft.
$264,500
Med. List Price
44 Properties
Page 1 of 4
$997,500
Subdivision: Rural
5
Beds
4
Baths
6,369
Sq.Ft.
1960
Year Built
85
Days on Site
20022226
MLS
Stunning Federal Flemish brick ranch on 23 +/- gently rolling acres convenient to I-64. Turn on the tree-lined driveway to circular drive. Custom foyer w/leaded glass, marble floors & transoms. 8...
$695,000
Subdivision: Rural
3
Beds
2
Baths
1,454
Sq.Ft.
1990
Year Built
658
Days on Site
1906947
MLS
Bring your cows, goats, sheep, and alpacas! And your fishing poles, hiking boots and your 4 wheelers! No restrictions! This sprawling 204 +/- acre completely fenced farm can be yours today! The...
$514,900
Subdivision: Fairway Villa
5
Beds
3F11/2
Baths
3,680
Sq.Ft.
2005
Year Built
130
Days on Site
20019134
MLS
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 a beautiful back yard oasis will win...
$500,000
Subdivision: Witherspoon
4
Beds
4
Baths
5,083
Sq.Ft.
1906
Year Built
79
Days on Site
20023062
MLS
Stunning turn of the century home loaded w/ character. The first floor features an expansive foyer w/hardwood floors, stunning chandelier valued at over $12,000, & fireplace; library with coffered...
$499,500
Subdivision: Fairway Villa
6
Beds
4F11/2
Baths
5,256
Sq.Ft.
2000
Year Built
111
Days on Site
20020602
MLS
Back on the market and with a reduced price! A custom built home on a cul-de-sac in one of Winchester's small exclusive neighborhoods. Close to downtown and the Winchester Country Club. This...
$499,000
Subdivision: The Ridings
3
Beds
2F11/2
Baths
2,732
Sq.Ft.
1991
Year Built
75
Days on Site
20023303
MLS
You know before you open the door, this stately 2-story brick home is move-in ready. From the 5-Sereine Acres, mature tree lined drive and landscaping, airy sunroom, oversized deck outside to the...
$479,000
Subdivision: Rural
3
Beds
3
Baths
2,872
Sq.Ft.
2018
Year Built
170
Days on Site
20016108
MLS
Are you looking for your forever home in the country? This could be it! This meticulously maintained (smoke free and pet free) custom home was built in 2018 with special attention to every small...
$475,000
Subdivision: Thomson Addition
4
Beds
3
Baths
5,516
Sq.Ft.
1954
Year Built
137
Days on Site
1920763
MLS
Relax and enjoy on the serene back screened-in porch. Walk to Winchester's charming downtown to shop, dine or antique. Spacious and elegantly appointed home featuring formal and informal rooms for...
$469,000
Subdivision: Rural
3
Beds
2F11/2
Baths
3,158
Sq.Ft.
1964
Year Built
39
Days on Site
20024947
MLS
This property is located in one of Clark County's most beautiful areas. Conveniently located near Winchester and Paris, you can access I-64 at exit 96 in just a few minutes. The tri-level with an...
Under Contract
437 Lynnway Drive Winchester, KY 40391
$409,900
Subdivision: Stoneybrook
4
Beds
2F11/2
Baths
4,584
Sq.Ft.
1991
Year Built
45
Days on Site
20025068
MLS
Don't miss out on this spacious 4 bedroom all brick home with a walkout finished basement located on a large corner lot. The interior features 4 fireplaces(Living, family, great room & owners suite),...
$399,900
Subdivision: Fairholme Estates
4
Beds
3F11/2
Baths
2,433
Sq.Ft.
2016
Year Built
51
Days on Site
20024831
MLS
WOW! Come see this spacious 4 bedroom/4 bath, move in ready home on .44 acres with a full walk out basement ready for your finishing touches! The basement has a framed potential 5th bedroom and...
$398,900
Subdivision: Stoneybrook
5
Beds
3F11/2
Baths
3,501
Sq.Ft.
1996
Year Built
5
Days on Site
20100881
MLS
The owners pride shows throughout this immaculate home. As you enter through the front door the gleaming hardwoods and the pristine crown moldings exemplify the quality of the condition of the house....