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Street View
$325,000
Monthly Est:$1,618
4 Beds
- 2 Baths
2 full baths
3,261sqft
443 S Maple St, Winchester, KY 40391
$325,000
$1,618/moEst:
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Single Family Residence
Built in 1905
$-- HOA
0.39 acre lot
$100/sq.ft
Description
Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.
- Houzeo last checked: 12 hours ago
- Listing updated: September 28, 2026 at 1:38 pm
- Listing Provided by: Terra Long (859) 707-7366 , Shane T Underwood | Keller Williams Commonwealth (859) 721-2121
- Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26008225

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1905
HOA Fees
-
Finished Area
3,261 sqft
Lot Size
0.39 acre lot
Basement Area
- sqft
MLS Name
Lexington Bluegrass AOR (Imagine) MLS
MLS Number
26008225
MLS Status
Active
Days on Market
175
Cumulative Days on Market
163

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 2
Interior
Cooling
Electric, None
Window Features
Blinds
Appliances
Dishwasher, Double Oven, Range, Refrigerator
Flooring
Carpet, Hardwood, Vinyl
Exterior Features
Awning(s)
Sewer
Public Sewer
Heating
Forced Air
Construction
Year Built
Year Built: 1905
Home type
Single Family Residence
Foundation Details
Stone
Construction Materials
Vinyl Siding
Roof
Shingle
Utilities & Energy
Laundry Features
Electric Dryer Hookup, Main Level, Washer Hookup
Fireplace Features
Living Room
Basement
Unfinished
Parking Features
Attached Garage, Basement, Driveway, Garage Door Opener, Garage Faces Side, Off Street
Water Source
Public
Other Features
Lot Features
Many Trees
Patio And Porch Features
Porch
Subdivision Name
Downtown
Price History
| Date | Event | Price |
|---|---|---|
09/28/2026 Source: | Price Decreased | $325,000 -4.41% $100/sqft |
06/08/2026 Source: | Price Decreased | $340,000 -2.86% $104/sqft |
04/18/2026 Source: | Listed for Sale | $350,000 $107/sqft |
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Based on information from the IMAGINE MLS® through Oct 09, 2026, 02:30PM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.
Advertising Broker: Donna Mink | Mink Realty









