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 October 6, 2022
17
Listed
61
Avg. DOM
$109.10
Avg. $ / Sq.Ft.
$230,000
Med. List Price
17 Properties
Page 1 of 2
$149,000
Neighborhood: Stuarts Addition
3
Beds
2
Baths
1,655
Sq.Ft.
1940
Year Built
8
Days on Site
22021436
MLS
Got paint? Looking for a home with upside remodeling potential in a great location? Welcome to College St in Winchester, KY just across the street from the newly refurbished Fort Freeman Park and...
Open 10/8
420 Schoolhouse Ln Winchester, KY 40391
$194,900
Neighborhood: Rural
3
Beds
1
Baths
1,228
Sq.Ft.
1900
Year Built
11
Days on Site
22021369
MLS
NEW PRICE!! This House Qualifies For 100% Financing! Gorgeous Fully Renovated Ranch Home In The Country With A Big Fully Fenced Backyard, Expansive Deck, Front Wrap-Around Porch And A Wood Burning...
$319,900
Neighborhood: Rural
5
Beds
2F11/2
Baths
2,520
Sq.Ft.
1940
Year Built
13
Days on Site
22021321
MLS
This home should check a LOT of your boxes! This is YOUR chance to enjoy the serenity and privacy of living in the country, yet less than 5 miles from Winchester! Sit on the screened-in front porch...
$234,900
Neighborhood: Hickman Addition
4
Beds
1F11/2
Baths
2,170
Sq.Ft.
1940
Year Built
14
Days on Site
22021227
MLS
Don't miss this beautiful and charming Craftsman style home, just a short walk to College Park Gym, Pool and the Park. The classic style wrap-around covered front porch is perfect for starting your...
4
Beds
2
Baths
1,498
Sq.Ft.
1940
Year Built
14
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...
Pending
13 Euclid Ave Winchester, KY 40391
$52,000
Neighborhood: Witherspoon
2
Beds
2
Baths
1,893
Sq.Ft.
1917
Year Built
17
Days on Site
22020973
MLS
COMP USE ONLY - Estate Sale
Pending
505 Colby Rd Winchester, KY 40391
$359,900
Neighborhood: Colby Hills
3
Beds
2F11/2
Baths
2,677
Sq.Ft.
1900
Year Built
23
Days on Site
22020532
MLS
The charm of this fully renovated 1900's house is breathtaking. This home offers a primary bedroom with attached dressing room and full bath. Upstairs holds two large bedrooms and a full bath. The...
$199,900
Neighborhood: Lane Addition
3
Beds
1
Baths
1,309
Sq.Ft.
1940
Year Built
29
Days on Site
22020132
MLS
Absolutely charming three bedroom corner lot home screams NEW NEW NEW. New addition, new flooring, new roof, new water heater, new HVAC system, new fixtures, fresh paint. Get the message?...
Pending
306 W Lexington Ave Winchester, KY 40391
$138,000
Neighborhood: Downtown
5
Beds
1F11/2
Baths
2,744
Sq.Ft.
1935
Year Built
45
Days on Site
22018839
MLS
There is much potential in this property. This could be a wonderful family home or rental property. It includes 3 bedrooms, one full and one half bath, kitchen, and a large living room on the...
Pending
107 Jefferson St Winchester, KY 40391
$149,900
Neighborhood: Downtown
2
Beds
1
Baths
3,280
Sq.Ft.
1918
Year Built
53
Days on Site
22018257
MLS
Built circa 1918, this home is a spacious slice of Winchesters past, present & future. This house is a downtown, walkable treasure that is sure to make a wonderful home for its next generation of...
$261,900
Neighborhood: Burns Addition
4
Beds
2
Baths
3,299
Sq.Ft.
1895
Year Built
73
Days on Site
22016460
MLS
Elegant older 3 story home built in the late 1800's. Close to downtown and two blocks from College Park. Large rooms, with bedroom and bath on first level. Three bedrooms and one bath, plus a...
Pending
209 W Hickman St Winchester, KY 40391
$120,000
Neighborhood: Burns Addition
4
Beds
1F11/2
Baths
1,629
Sq.Ft.
1940
Year Built
91
Days on Site
22014948
MLS
Do you love older homes? Here is your chance to own one that won't bust your budget located in the heart of Winchester near College Park and downtown. This stucco-sided home offers an inviting front...