Historic Homes in Winchester, KY.  Homes for Sale built prior to 1940.

Included below are Historic Homes for sale in Winchester Kentucky Neighborhoods and Subdivisions. If you would like more information on any of these Historic Homes on the Winchester real estate market, just click the "Request More Information" button when viewing the details of that property. We can provide you with disclosures, past sales history, dates and prices of homes recently sold nearby, and more.

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Historic Homes inWinchester Kentucky February 6, 2023
12
Listed
57
Avg. DOM
$104.91
Avg. $ / Sq.Ft.
$220,000
Med. List Price
12 Properties
$469,900
Neighborhood: Thomson Addition
4
Beds
3
Baths
3,236
Sq.Ft.
1911
Year Built
3
Days on Site
23001909
MLS
This timeless ranch home located in the heart of Winchester has the perfect combination of original early 1900s charm and modern updates. As you make your way through the main level you'll notice...
$254,900
Neighborhood: Burns Addition
4
Beds
2
Baths
3,299
Sq.Ft.
1895
Year Built
18
Days on Site
23000588
MLS
Imagine coming home to this historic 1800's home, with grand features like hardwood floors, tall ceilings, large rooms, working gas fireplaces, handcrafted staircase, handcrafted baseboards, and a...
Pending
141 Alabama St Winchester,  KY 40391
$70,000
Neighborhood: South Park Addition
4
Beds
2
Baths
2,122
Sq.Ft.
1940
Year Built
26
Days on Site
23000689
MLS
Attention investors and home flippers, here's a great potential investment opportunity. This property has a full apartment on each floor both containing a living room, kitchen, full bath and 2...
$225,000
Neighborhood: Hickman Addition
3
Beds
2
Baths
2,200
Sq.Ft.
1923
Year Built
26
Days on Site
23000723
MLS
Here's an opportunity to own a colonial style home in an older, established neighborhood within a 10-15 minute walk to Winchester's historic downtown! Many upgrades have been done over the years to...
Pending
46 Hughes Ave Winchester,  KY 40391
$29,000
Neighborhood: Downtown
2
Beds
1
Baths
679
Sq.Ft.
1940
Year Built
29
Days on Site
23000469
MLS
Here is that affordable flip house you have been looking for! 2 bed 1 bath canvas waiting to be revived by you! House needs complete remodel! Mostly gutted already. Sold AS-IS!! What you see is what...
$155,000
Neighborhood: Lincoln Park
4
Beds
1
Baths
1,596
Sq.Ft.
1940
Year Built
60
Days on Site
22026155
MLS
A beautiful newly renovated large brick home on a double lot with 4 bedrooms located in Lincoln Park waiting for you near downtown Winchester. Contact us today for viewing!
$320,000
Neighborhood: Downtown
4
Beds
2
Baths
3,436
Sq.Ft.
1920
Year Built
62
Days on Site
22026063
MLS
A beautiful classic American home in the heart of Winchester is on the market for the first time in over forty years! The front porch welcomes you home, your next step takes you into an open foyer...
Pending
322 S Burns Ave Winchester,  KY 40391
$269,900
Neighborhood: Downtown
3
Beds
2F11/2
Baths
1,991
Sq.Ft.
1940
Year Built
63
Days on Site
22026004
MLS
Beautiful 1.5 story home in the heart of Winchester. Lovingly remodeled. Minutes from the library and park. Short drive to Lexington. The open concept flows from the front door to the family room,...
$165,001
Neighborhood: Victory Heights
3
Beds
2
Baths
2,607
Sq.Ft.
1940
Year Built
64
Days on Site
22025939
MLS
Craftsman Style 1.5 story home situated on 4 residential lots. Offering over 2600 sq ft of living space. Home features 3 bedrooms and 2 full baths. Other features include formal living room, formal...
Pending
116 Alabama St Winchester,  KY 40391
$214,900
Neighborhood: Downtown
4
Beds
2
Baths
1,626
Sq.Ft.
1940
Year Built
98
Days on Site
22023984
MLS
Eloquently renovated. This house has so much to offer. No area in this home has been left untouched. From the quartz countertops to the custom staircase. Beautiful, uniform flooring, and great...
$585,000
Neighborhood: Rural
4
Beds
2F11/2
Baths
3,020
Sq.Ft.
1918
Year Built
113
Days on Site
22007571
MLS
This updated home and 2 acres are being offered for $585,000. Survey will be completed by seller prior to closing Additional acres are available. The Home was gutted and redone with an addition in...
4
Beds
2
Baths
1,498
Sq.Ft.
1940
Year Built
137
Days on Site
22021269
MLS
This historic home is the best of both worlds. Enjoy your private country setting, but also just minutes to town. This home includes four bedrooms, two bathrooms, new laminate flooring, and a covered...