443 S Maple St Winchester, KY 40391
Estimated payment $1,995/month
Highlights
- Living Room with Fireplace
- Wood Flooring
- No HOA
- Vaulted Ceiling
- Main Floor Primary Bedroom
- Neighborhood Views
About This Home
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.
Home Details
Home Type
- Single Family
Year Built
- Built in 1905
Lot Details
- 16,988 Sq Ft Lot
- Many Trees
Parking
- 1 Car Attached Garage
- Basement Garage
- Side Facing Garage
- Garage Door Opener
- Driveway
- Off-Street Parking
Home Design
- Stone Foundation
- Shingle Roof
- Vinyl Siding
Interior Spaces
- 3,261 Sq Ft Home
- 2-Story Property
- Vaulted Ceiling
- Blinds
- Living Room with Fireplace
- 3 Fireplaces
- Dining Room
- Den with Fireplace
- First Floor Utility Room
- Utility Room
- Neighborhood Views
- Attic Access Panel
- Unfinished Basement
Kitchen
- Double Oven
- Dishwasher
Flooring
- Wood
- Carpet
- Vinyl
Bedrooms and Bathrooms
- 4 Bedrooms
- Primary Bedroom on Main
- Bathroom on Main Level
- 2 Full Bathrooms
Laundry
- Laundry on main level
- Washer and Electric Dryer Hookup
Outdoor Features
- Covered Patio or Porch
- Awning
Schools
- Shearer Elementary School
- Robert Campbell Middle School
- Grc High School
Utilities
- Forced Air Heating System
Community Details
- No Home Owners Association
- Downtown Subdivision
Listing and Financial Details
- Assessor Parcel Number 054-2018-001-00
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $1,912 | $199,000 | $40,000 | $159,000 |
| 2024 | $1,287 | $175,000 | $40,000 | $135,000 |
| 2023 | $1,260 | $175,000 | $0 | $0 |
| 2022 | $1,325 | $175,000 | $0 | $0 |
| 2021 | $1,321 | $175,000 | $0 | $0 |
| 2020 | $1,336 | $175,000 | $0 | $0 |
| 2019 | $1,342 | $175,000 | $0 | $0 |
| 2018 | $1,343 | $175,000 | $0 | $0 |
| 2017 | $1,348 | $175,000 | $0 | $0 |
| 2016 | $202 | $175,000 | $0 | $0 |
| 2015 | $1,327 | $175,000 | $0 | $0 |
| 2013 | -- | $139,000 | $0 | $0 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 06/08/2026 06/08/26 | Price Changed | $340,000 | -2.9% | $104 / Sq Ft |
| 04/18/2026 04/18/26 | For Sale | $350,000 | -- | $107 / Sq Ft |
Source: ImagineMLS (Bluegrass REALTORS®)
MLS Number: 26008225
APN: 054-2018-00100
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Ask me questions while you tour the home.