# 443 S Maple Street, Winchester, KY 40391 > **TL;DR:** 4bd/2ba single family, $325,000 ($100/sqft), built 1905, 3,261 sqft. > Fireplace, Hardwood, A/C, 1-car garage. Est. $1,738/mo. Listed 196 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $325,000 | | Price/sqft | $100 | | Bedrooms | 4 | | Bathrooms | 2 full | | Square Feet | 3,261 | | Year Built | 1905 | | Lot Size | 16,988 sqft (0.39 acres) | | Stories | 2 | | Garage | 1-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 196 | ## Why This Home Stands Out - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,643 | | Estimated Insurance | $95 | | **Total** | **$1,738** | ## Nearby Schools - **Elementary:** Shearer - **Middle:** Robert Campbell - **High:** GRC ## Key Amenities - Fireplace - Hardwood - A/C - 1-car garage ## Property Highlights - Built in 1905 - 0.39 acre lot - 2 stories - Fireplace ## Description ### Agent 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. ## Location - **Address:** 443 S Maple Street, Winchester, KY 40391 - **County:** Clark - **Neighborhood:** Downtown - **Coordinates:** 37.987174, -84.182295 - **Google Maps:** https://www.google.com/maps?q=37.987174,-84.182295 ## Listing Agent - **Name:** Terra Long - **Brokerage:** Keller Williams Commonwealth - **Broker Phone:** (859) 721-2121 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/443-S-Maple-St_Winchester_KY_40391_M33932-97118?f=listhub&s=LBARKY&m=26008225&c=propsimple) ## Photos ![443 S Maple Street - Photo 1](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f428619081r.jpg) ![443 S Maple Street - Photo 2](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f878110205r.jpg) ![443 S Maple Street - Photo 3](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f493783700r.jpg) ![443 S Maple Street - Photo 4](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f4275224172r.jpg) ![443 S Maple Street - Photo 5](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3933117175r.jpg) ![443 S Maple Street - Photo 6](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3026447590r.jpg) ![443 S Maple Street - Photo 7](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2595168680r.jpg) ![443 S Maple Street - Photo 8](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2632359794r.jpg) ![443 S Maple Street - Photo 9](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2822652314r.jpg) ![443 S Maple Street - Photo 10](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f137470375r.jpg) ![443 S Maple Street - Photo 11](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3001835242r.jpg) ![443 S Maple Street - Photo 12](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f664760870r.jpg) ![443 S Maple Street - Photo 13](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3813423169r.jpg) ![443 S Maple Street - Photo 14](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1975617076r.jpg) ![443 S Maple Street - Photo 15](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1521736675r.jpg) ![443 S Maple Street - Photo 16](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f4063521666r.jpg) ![443 S Maple Street - Photo 17](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2193128543r.jpg) ![443 S Maple Street - Photo 18](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2779495511r.jpg) ![443 S Maple Street - Photo 19](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3463395666r.jpg) ![443 S Maple Street - Photo 20](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3764052624r.jpg) ![443 S Maple Street - Photo 21](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2731474740r.jpg) ![443 S Maple Street - Photo 22](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1274960527r.jpg) ![443 S Maple Street - Photo 23](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2402448453r.jpg) ![443 S Maple Street - Photo 24](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3963009880r.jpg) ![443 S Maple Street - Photo 25](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1442728632r.jpg) ![443 S Maple Street - Photo 26](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2606847507r.jpg) ![443 S Maple Street - Photo 27](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1232355376r.jpg) ![443 S Maple Street - Photo 28](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1440622242r.jpg) ![443 S Maple Street - Photo 29](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1666590992r.jpg) ![443 S Maple Street - Photo 30](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2173913767r.jpg) ![443 S Maple Street - Photo 31](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f4245299720r.jpg) ![443 S Maple Street - Photo 32](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3123986267r.jpg) ![443 S Maple Street - Photo 33](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f487844258r.jpg) ![443 S Maple Street - Photo 34](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2897571449r.jpg) ![443 S Maple Street - Photo 35](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3336001685r.jpg) ![443 S Maple Street - Photo 36](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2051327045r.jpg) ![443 S Maple Street - Photo 37](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f659700696r.jpg) ![443 S Maple Street - Photo 38](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f639742103r.jpg) ![443 S Maple Street - Photo 39](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2523822721r.jpg) ![443 S Maple Street - Photo 40](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1353298893r.jpg) ![443 S Maple Street - Photo 41](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2278453350r.jpg) ![443 S Maple Street - Photo 42](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f154137138r.jpg) ![443 S Maple Street - Photo 43](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f181061550r.jpg) ![443 S Maple Street - Photo 44](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f4252803267r.jpg) ![443 S Maple Street - Photo 45](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f4102545171r.jpg) ![443 S Maple Street - Photo 46](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3409338598r.jpg) ![443 S Maple Street - Photo 47](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2736438684r.jpg) ![443 S Maple Street - Photo 48](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1141957074r.jpg) ![443 S Maple Street - Photo 49](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f422505918r.jpg) ![443 S Maple Street - Photo 50](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1649145334r.jpg) ![443 S Maple Street - Photo 51](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3467375659r.jpg) ![443 S Maple Street - Photo 52](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1177749756r.jpg) ![443 S Maple Street - Photo 53](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2916893568r.jpg) ![443 S Maple Street - Photo 54](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2755728696r.jpg) ![443 S Maple Street - Photo 55](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f2147529073r.jpg) ![443 S Maple Street - Photo 56](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f1824668532r.jpg) ![443 S Maple Street - Photo 57](http://lh.rdcpix.com/b030c858876b5a00c7dc63a947218396l-f3729426564r.jpg) --- **MLS#:** 26008225 | **Updated:** 2026-10-22 **Source:** listhub *Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/443-s-maple-street-winchester-ky-40391-c77b89184ebc4e8684a656f7aca800ef) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/443-s-maple-street-winchester-ky-40391-c77b89184ebc4e8684a656f7aca800ef#listing", "url": "https://staging.propertysimple.ai/listing/443-s-maple-street-winchester-ky-40391-c77b89184ebc4e8684a656f7aca800ef", "name": "443 S Maple Street, Winchester, KY 40391", "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. 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