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4 Beds
2 Baths
3,261 sqft

$325,000

443 S Maple Street, Winchester KY, 40391

Price per sqft$99.66
Built in1905
Property size3,261 sqft
Property typeResidential
Listed by Terra Long with Keller Williams Commonwealth

Overview

Active

Listed Apr 18, 2026

Updated 12 days ago

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.

$2,162/mo

Est. mortgage payment based on a $325,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
26008225

Interior Features

Bedrooms
4
Bathrooms
2
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.39 Acres

Other Property Details

Garage
Yes
View
Yes
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Listing Contact:  

The IDX display contains information sourced from the Bluegrass REALTORS® as of 9/29/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

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Data last updated on 9/29/2026 at 3:32 AM UTC

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