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 May 25, 2022
14
Listed
43
Avg. DOM
$96.34
Avg. $ / Sq.Ft.
$176,000
Med. List Price
14 Properties
Page 1 of 2
$184,000
Neighborhood: Victory Heights
3
Beds
2
Baths
2,607
Sq.Ft.
1940
Year Built
6
Days on Site
22010414
MLS
Plenty of space inside and out of this home on .52 acres convenient to everything in Winchester. Home offers 3 bedrooms, 2 full baths, hardwood floors, large family room with woodburning fireplace,...
$289,900
Neighborhood: Downtown
4
Beds
2
Baths
3,402
Sq.Ft.
1902
Year Built
21
Days on Site
22008982
MLS
This is an Estate, Selling AS IS, inspections welcome, in love with yesterday year, you can return to a quieter and gentler place with this American Colonial, hardwood floors, high ceilings,...
Under Contract
227 W Hickman St Winchester, KY 40391
$199,900
Neighborhood: Hickman Addition
3
Beds
2
Baths
2,053
Sq.Ft.
1940
Year Built
24
Days on Site
22008647
MLS
This all brick cottage has all you need. Three bedroom with 2 full baths. Original hard wood floors. Very Convenient location within walking distance to downtown College park/pool and our...
Under Contract
139 Franklin Ave Winchester, KY 40391
$169,500
Neighborhood: Fairview
2
Beds
1
Baths
1,052
Sq.Ft.
1940
Year Built
27
Days on Site
22008387
MLS
Hurry to check out this quaint 2BR/1BA brick home sitting on beautifully landscaped property! With attention to detail evident on all sides, perhaps your favorite will be the completely fenced and...
$114,500
Neighborhood: Downtown
3
Beds
2
Baths
1,810
Sq.Ft.
1930
Year Built
30
Days on Site
22005620
MLS
Property sold as-isBest for cash buyers, will consider conventional. All information provided is to the best of seller's knowledge, all buyers and agents should exercise due diligence and verify all...
$650,000
Neighborhood: Rural
4
Beds
2F11/2
Baths
3,020
Sq.Ft.
1918
Year Built
34
Days on Site
22007571
MLS
This updated home and 2 acres are being offered for $650,000. Survey will be completed by seller prior to closing Additional acres are available. The Home was gutted and redone with an addition in...
Pending
82-84 Brink Ave Winchester, KY 40391
$170,000
Neighborhood: Downtown
3
Beds
2F11/2
Baths
2,451
Sq.Ft.
1930
Year Built
34
Days on Site
22007804
MLS
A house that can be beautiful with some TLC, this house will not go FHA/VA, needs much love, large lot, 2.32 acres as per PVA, buyer and agents to satisfy themselves as to the size of property and...
$250,000
Neighborhood: Burns Addition
4
Beds
2
Baths
3,180
Sq.Ft.
1940
Year Built
34
Days on Site
22007829
MLS
Charming 1940's craftsman in downtown historic district Winchester with a great front porch! Don't miss out on this spacious 3180 sq. ft. 4 bed, 2 bath home! Great hardwood floors, so much storage...
Pending
204 Boone Ave Winchester, KY 40391
$265,000
Neighborhood: Thomson Addition
3
Beds
1F11/2
Baths
2,870
Sq.Ft.
1920
Year Built
34
Days on Site
22007855
MLS
This is your opportunity to own a beautiful two-story, hip-roofed brick American Four Square style home believed to be built in the 1920's Original hardwoods throughout, three sets of solid wood...
Pending
352 Boone Ave Winchester, KY 40391
$67,500
Neighborhood: Thomson Addition
4
Beds
2
Baths
1,681
Sq.Ft.
1930
Year Built
35
Days on Site
22007736
MLS
***Highest and Best Offers Requested*** Seller has received multiple offers for this home and requests each buyer submit their Highest and Best offer. Offers are due by Monday April 25 at 3 pm in the...
Pending
306 W Hickman St Winchester, KY 40391
$182,000
Neighborhood: Downtown
3
Beds
2
Baths
1,550
Sq.Ft.
1940
Year Built
48
Days on Site
22006674
MLS
This All American bungalow style home is fully renovated, with original hardwood floors throughout, and comes with 3 bedrooms and 2 full bathrooms, with a Large living room that opens to the dining...
$115,000
Neighborhood: Witherspoon
4
Beds
2
Baths
2,453
Sq.Ft.
1920
Year Built
70
Days on Site
22004857
MLS
RARE FIND FLIP DEAL!! Location location location! You can't find this type of deal anymore!! Easily make two duplex rent $1000 each or short term rental! Fully gutted and plan approved by bank ARV...