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 July 25, 2021
23
Listed
71
Avg. DOM
$91.82
Avg. $ / Sq.Ft.
$195,000
Med. List Price
23 Properties
Page 1 of 2
$335,000
Subdivision: Thomson Addition
6
Beds
3
Baths
3,749
Sq.Ft.
1920
Year Built
2
Days on Site
20114512
MLS
Spacious two story home nestled in the heart of Winchester, located on prestigious Maple Street. This location offers quick access to downtown for the many events and shows that are always taking...
Open 7/25
256 S Highland St Winchester, KY 40391
$229,900
Subdivision: Downtown
3
Beds
1F11/2
Baths
2,075
Sq.Ft.
1935
Year Built
9
Days on Site
20113991
MLS
Renovated South Highland Beauty! The Owners Have Put Their Heart Into This Home And It Shows. Every Detail Is Just Perfect. This 3 Bedroom 1 1/2 Bath Home Features Hardwood Floors; All New Light...
Pending
26 Vine St Winchester, KY 40391
$55,000
Subdivision: Downtown
2
Beds
1
Baths
1,059
Sq.Ft.
1940
Year Built
13
Days on Site
20113646
MLS
Inside pictures not provided. Tenant occupied...Attention Investors and First Time Homebuyers!!! This is a listing you do not want to miss!! This two bedroom one bath home with large yard is...
$1,175,000
Subdivision: Rural
6
Beds
3F11/2
Baths
7,600
Sq.Ft.
1878
Year Built
14
Days on Site
20113573
MLS
This stately Victorian Farmhouse lovingly known as Rotherwood boasts breathtaking countryside views at every turn and sits on over 25 acres! Built in 1887, this gracious estate has been exquisitely...
$131,000
Subdivision: Thomson Addition
4
Beds
2
Baths
1,680
Sq.Ft.
1940
Year Built
19
Days on Site
20107878
MLS
Lots of square footage at a great price. This is a very unique home with lots of room. Schedule your showing today
Under Contract
111 Kentucky St Winchester, KY 40391
$125,000
Subdivision: South Park Addition
4
Beds
2
Baths
1,764
Sq.Ft.
1940
Year Built
19
Days on Site
20113188
MLS
This spacious home is located in the heart of Winchester for convenient access to downtown, or I-64 and the Mountain Parkway. With 4 bedrooms, and 2 baths this could be a good fit for that growing...
Pending
420 S Main St Winchester, KY 40391
$49,900
Subdivision: Thomson Addition
2
Beds
1
Baths
1,340
Sq.Ft.
1935
Year Built
30
Days on Site
20112357
MLS
This conveniently located property has a large back yard and lots of potential. Bring your own HGTV ideals to revive this classic home. Can easily walk downtown or to the local market for a home...
$319,900
Subdivision: Thomson Addition
4
Beds
1F11/2
Baths
3,304
Sq.Ft.
1910
Year Built
32
Days on Site
20112194
MLS
Charm meets convince!! This home is over 3000 sqft home sitting on a huge lot on the historic Boone Avenue. The exterior features include a large covered front and back porch with a mature garden in...
$165,000
Subdivision: Downtown
2
Beds
2
Baths
1,490
Sq.Ft.
1940
Year Built
38
Days on Site
20111700
MLS
Charming and lovely older home with tall ceilings, in the city area. New Wintech windows on the main floor. Windows in basement not replaced. Two bedrooms and with third bedroom possible in the...
Pending
130 W Lexington Ave Winchester, KY 40391
$100,000
Subdivision: Downtown
4
Beds
3
Baths
3,418
Sq.Ft.
1930
Year Built
41
Days on Site
20111429
MLS
Great location. Downtown Winchester, KY. Home is uninhabitable. Bring offers.
Pending
118 Jefferson St Winchester, KY 40391
$115,500
Subdivision: Rural
4
Beds
2F11/2
Baths
2,125
Sq.Ft.
1890
Year Built
51
Days on Site
20110709
MLS
With all of the recent upgrades, this is a must see for yourself to appreciate the updates these sellers have made. From opening up the kitchen for a complete remodel, to the 1st level primary...
$143,000
Subdivision: Thomson Addition
3
Beds
1F11/2
Baths
1,597
Sq.Ft.
1940
Year Built
62
Days on Site
20109937
MLS
This home overflows with character and charm! It is definitely move-in ready featuring large rooms throughout including a HUGE primary suite with sitting room, closet and half-bath. This area also...