For Sale
Single family home for sale at 443 S Maple St, Winchester, KY 40391 | MLS# 26008225 | Listing updated on 2026-09-28
Photo 1 of Single family home for sale at 443 S Maple St, Winchester, KY 40391 | MLS# 26008225 | Listing updated on 2026-09-28
Photo 2 of Single family home for sale at 443 S Maple St, Winchester, KY 40391 | MLS# 26008225 | Listing updated on 2026-09-28
Photo 3 of Single family home for sale at 443 S Maple St, Winchester, KY 40391 | MLS# 26008225 | Listing updated on 2026-09-28
Photo 4 of Single family home for sale at 443 S Maple St, Winchester, KY 40391 | MLS# 26008225 | Listing updated on 2026-09-28
53+
Beds Icon

Street View

$325,000

Monthly Est:$1,618

  • Beds Icon4 Beds
  • Beds Icon
    2 Baths
  • Beds Icon3,261sqft

443 S Maple St, Winchester, KY 40391

$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 Lexington Bluegrass AOR (Imagine) MLS-KY

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Clark County

  • City

    Winchester

  • 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

DateEventPrice

09/28/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26008225

Price Decreased

$325,000 -4.41%

$100/sqft

06/08/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26008225

Price Decreased

$340,000 -2.86%

$104/sqft

04/18/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26008225

Listed for Sale

$350,000

$107/sqft

Nearby Homes

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.

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