Search Listings

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.

And, for your convenience, register for a free account to receive email alerts whenever new Winchester real estate listings come on the market that match your criteria.

Winchester November 27, 2021
66
Listed
59
Avg. DOM
$124.59
Avg. $ / Sq.Ft.
$194,700
Med. List Price
66 Properties
Page 1 of 6
Under Contract
490 Oil Springs Rd Winchester, KY 40391
$1,200,000
Subdivision: Rural
4
Beds
3
Baths
2,736
Sq.Ft.
2000
Year Built
180
Days on Site
20110329
MLS
Wow!! So many possibilities with this wonderful property of 97.9 Gorgeous Acres. There is a custom built main home with 4 Bedrooms and 3 Baths and a cozy cottage as well. Very nice interior roadways...
Under Contract
185 Sundown Ln Winchester, KY 40391
$1,049,000
Subdivision: Rural
5
Beds
6F31/2
Baths
6,580
Sq.Ft.
2000
Year Built
41
Days on Site
20122560
MLS
Stunning home on 7+/- acres less than 15 minutes to Hamburg. This lovely 1.5 story brick home has hardwood flooring throughout, tall ceilings ranging from 10'-16', finished basement, heated saltwater...
$774,900
Subdivision: Rural
3
Beds
3
Baths
2,744
Sq.Ft.
2014
Year Built
85
Days on Site
20119126
MLS
This Mike Childers Exclusive 1 story ranch on an unfinished walkout bsmt, sits on 22+ acres with breathtaking views complete w/ rustic barn. Once you enter the front entrance, the open flow of the...
Under Contract
2925 Combs Ferry Rd Winchester, KY 40391
$725,000
Subdivision: Rural
4
Beds
2F11/2
Baths
2,926
Sq.Ft.
2009
Year Built
46
Days on Site
20122142
MLS
Situated on 6 acres of Kentucky's finest rolling countryside, this custom one level masonry home features all the high end luxuries you are looking for. Enjoy the covered front porch with rocking...
$700,000
Subdivision: Rural
4
Beds
4F11/2
Baths
2,700
Sq.Ft.
2021
Year Built
134
Days on Site
20113969
MLS
Take a peek at this one! Proposed Construction! Break ground today on your new custom home! This 10-acre parcel is the perfect combination of a rural setting with city convenience. A short drive and...
3
Beds
3
Baths
3,132
Sq.Ft.
1967
Year Built
121
Days on Site
20115026
MLS
Your dream home has finally been listed! Bring your horses, your cattle, your goats, chickens, and, of course, your dogs and cats! And don't forget your fishing pole. A beautiful brick ranch home...
3
Beds
2F11/2
Baths
2,620
Sq.Ft.
1982
Year Built
55
Days on Site
20121484
MLS
Impressive view as you arrive at this home overlooking the countryside. Enjoy the sun coming up and the beautiful sunsets. You'll have all the comforts of home in this nice layout of a one level...
$475,000
Subdivision: Rural
3
Beds
2F11/2
Baths
2,294
Sq.Ft.
1964
Year Built
16
Days on Site
20124520
MLS
You don't want to miss this gorgeous 6.82 acre home located in one of the most desired locations. Wake up to a gorgeous 800 acre farm and a sunrise and sunset you are sure to love! Conveniently...
$437,000
Subdivision: Royal Oak Estates
3
Beds
2
Baths
1,998
Sq.Ft.
2022
Year Built
111
Days on Site
20116315
MLS
Proposed construction for a stunning three bed two bath ranch in Royal Oak Estates. This farmhouse design features tons of upgrades including granite countertops, tiled master shower, LVP flooring,...
Under Contract
1778 Elkin Station Rd Winchester, KY 40391
3
Beds
2F11/2
Baths
2,060
Sq.Ft.
2015
Year Built
43
Days on Site
20122187
MLS
Calling all nature lovers. Looking for a property that you can explore, hunt, swim, and enjoy the modern conveniences on then look no farther. This custom built ranch home is nestled on 8.86 acres...
3
Beds
2
Baths
2,470
Sq.Ft.
2012
Year Built
16
Days on Site
20124224
MLS
Are you looking for a one level home on fenced 5 acres in Clark County, not too far and not too close to Winchester & Mt. Sterling at 1480 White Turley Rd. This three bedroom, two bath features...
$375,000
Subdivision: Rural
3
Beds
2
Baths
1,800
Sq.Ft.
2007
Year Built
33
Days on Site
20123271
MLS
Beautiful 10 Acre farm with a beautiful pond. This is a desired location only minutes from town but still in the country. 3 Bedroom, 2 Full Bathrooms. New hardwood flooring 2014, HVAC 2014, hot...