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.
For sale
Price cut: $10K (6/8)
$340,000
443 S Maple St, Winchester, KY 40391
4beds
3,261sqft
Single Family Residence
Built in 1905
0.39 Acres Lot
$327,100 Zestimate®
$104/sqft
$-- HOA
What's special
- 76 days |
- 952 |
- 55 |
Zillow last checked:
Listing updated:
Listed by:
Terra Long 859-707-7366,
Keller Williams Commonwealth,
Shane T Underwood 859-699-2969,
Keller Williams Commonwealth
Source: Imagine MLS,MLS#: 26008225
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: First
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Bedroom 4
- Level: Second
Bathroom 1
- Description: Full Bath
- Level: First
Bathroom 2
- Description: Full Bath
- Level: Second
Den
- Level: First
Dining room
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Other
- Description: Sun Room
- Level: First
Utility room
- Description: in closet by full bath
- Level: First
Heating
- Forced Air
Cooling
- Electric, None
Appliances
- Included: Double Oven, Dishwasher, Refrigerator, Range
- Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
Features
- Flooring: Carpet, Hardwood, Vinyl
- Windows: Blinds
- Basement: Unfinished
- Number of fireplaces: 3
- Fireplace features: Living Room, Den
Interior area
- Total structure area: 3,261
- Total interior livable area: 3,261 sqft
- Finished area above ground: 3,261
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Attached Garage, Basement, Driveway, Garage Door Opener, Off Street, Garage Faces Side
- Garage spaces: 1
- Has uncovered spaces: Yes
Features
- Levels: Two
- Exterior features: Awning(s)
- Fencing: None
- Has view: Yes
- View description: Neighborhood
Lot
- Size: 0.39 Acres
- Features: Many Trees
Details
- Parcel number: 054201800100
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Stone
- Roof: Shingle
Condition
- Year built: 1905
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Downtown
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $104/sqft
- Tax assessed value: $175,000
- Annual tax amount: $1,287
- Date on market: 4/18/2026
Estimated market value
$327,100
$311,000 - $343,000
$2,154/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/8/2026 | Price change | $340,000-2.9%$104/sqft |
Source:  Imagine MLS #26008225 Report a problem | ||
| 4/18/2026 | Listed for sale | $350,000$107/sqft |
Source: Imagine MLS #26008225 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $1,287 -2.9% | $175,000 |
| 2023 | $1,325 | $175,000 |
| 2022 | $1,325 +0.3% | $175,000 |
| 2021 | $1,321 -1.1% | $175,000 |
| 2020 | $1,336 +574.1% | $175,000 |
| 2019 | $198 | $175,000 |
| 2018 | $198 -1.2% | $175,000 |
| 2017 | $201 -0.5% | $175,000 |
| 2016 | $202 | $175,000 |
| 2015 | $202 -0.6% | $175,000 +25.9% |
| 2013 | $203 | $139,000 -33.1% |
| 2011 | -- | $207,700 |
| 2010 | -- | $207,700 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 40391
Nearby schools
GreatSchools rating
- 5/10Shearer Elementary SchoolGrades: K-4Distance: 0.7 mi
- 5/10Robert D Campbell Junior High SchoolGrades: 7-8Distance: 0.8 mi
- 5/10George Rogers Clark High SchoolGrades: 9-12Distance: 2.5 mi
Schools provided by the listing agent
- Elementary: Shearer
- Middle: Robert Campbell
- High: GRC
Source: Imagine MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Kentucky
- Clark County
- Winchester
- 40391
- 443 S Maple St
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