Backup offers
$2,993 Closing Credit¹
#25003180, Listing Office: Marshall Lane Real Estate - Lexington
$259,000 List price
363 S Main St Winchester, KY 40391
$3,076
Closing credit¹
3 beds
2 full
0.5 acres
House
Property details
About 363 S Main St
Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle. With 2,142 square feet of living space, there's plenty of room for a growing family to spread out and feel right at home. You'll love the inviting layout, featuring a cozy loft area ideal for relaxing with a good book or creating a quiet retreat. Located just minutes from local schools, shops, and restaurants, this home provides unbeatable convenience in a welcoming community. Don't miss your chance to tour this beautifully maintained gem--schedule your showing today and see why 363 South Main Street could be your perfect next home!
Highlights
Home typeSingle Family Residence
HeatingNatural Gas
StatusActive
CoolingElectric
Lot size0.49 Acres
Year built1940
ParkingDriveway
MLS #25009250
Summary
- Full Bathrooms: 2
- Appliances: Dryer, Washer, Refrigerator, Range, Microwave, Dishwasher
- Flooring Type: Carpet, Tile, Hardwood
- Interior: Dining Area, Bedroom First Floor
- Total Bedroom Count: 3
- Parking: Driveway
- Exterior: Deck, Porch
- Heating: Natural Gas
- Cooling: Electric
- List Price: $259,000
- Annual Tax Amount: $1,374
- Tax Year: 2023
- Directions: From I-64, turn onto 627 Paris Road to Winchester, after 1.6 miles turn left onto W Lexington Avenue. Finally, turn right onto South Main and the home will be on your left after half a mile.
- Year Built: 1940
- Stories: 1
- Lot Size: 0.49 Acres
- MLS Number: 25009250
- Office Name: HomeLand Real Estate Inc
- Office Phone: (606) 356-3063
- Office Email: shannon@kyhomeland.com
The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Lexington-Bluegrass Association of Realtors Multiple Listing Service. Real estate listings held by IDX Brokerage firms other than this broker, are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX Brokers. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. © 2025 LBAR Multiple Listing Service. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 5/29/2025, 9:20:33 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Get an agent. Get a mortgage. Save big.¹
$259,000
363 S Main St
$3,076
closing credit¹
Sell your home with Rocket and save even more!
Seller rebate
0.5% sale price²
Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $139,500 | $1,374 |
| 2022 | $139,500 | $1,374 |
| 2021 | $139,500 | $1,370 |
| 2019 | $139,500 | $203 |
| 2018 | $139,500 | $203 |
History based on county public records data.
Nearby schools
3
Shearer Elementary School
Public District KG-4
0.7 mi
•244 E Broadway St
4
Justice Elementary School
Public District KG-4
1.5 mi
•350 Mount Sterling Rd
3
Conkwright Elementary School
Public District KG-4
1.6 mi
•360 Mount Sterling Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $29,082. Typical income of Winchester, KY residents is less than $<35k annually. The most common type of family is single, no kids. The most common level of education of people living in this area is high school diploma.
How much money do the neighbors make?
56%
<35k
37%
35k-100k
6%
100k-200k
1%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
What types of families live nearby?
41%
Single, No Kids
13%
Single, with Kids
29%
Married, No Kids
17%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
16%
<11 yrs old
8%
12-17 yrs old
20%
18-34 yrs old
42%
35-64 yrs old
14%
65+ yrs old
What do the neighbors do for fun?
Extreme Sports
Pro Wrestling
Figure Skating
Where do the neighbors shop?
Academy Sports & Outdoors
Wal-Mart
Kmart
Where do the neighbors go to eat?
Little Caesars
Sonic
Bob Evans
What do the neighbors drive?
Chevrolet
Oldsmobile
Buick
What do the neighbors listen to?
Country
Contemporary Inspirational- Oldies
All data provided by Home Junction and Claritas
Similar homes for sale
$3,147 Closing Credit¹
#25006079, Listing Office: Berkshire Hathaway HomeServices Foster Realtors
$3,384 Closing Credit¹
#25007670, Listing Office: Colwell Realty Professionals, Inc.
$3,384 Closing Credit¹
#25004895, Listing Office: Real Estate Appraisal Services
$2,666 Closing Credit¹
#25007615, Listing Office: Dream Maker Realty, LLC
Backup offers
$2,494 Closing Credit¹
#25003988, Listing Office: Woods Realty Group
$2,374 Closing Credit¹
#25010184, Listing Office: ERA Select Real Estate
$2,316 Closing Credit¹
#25010224, Listing Office: Rector Hayden Realtors
$2,968 Closing Credit¹
#25005267, Listing Office: Freedom Realty & Property Management
$3,266 Closing Credit¹
#25006738, Listing Office: RE/MAX Creative, Winchester
Frequently asked questions
Living in Winchester, KY
Winchester's transportation infrastructure supports both private and public transit options, with local bus services providing connectivity within the city. The community's layout offers areas that are pedestrian-friendly, encouraging walking and biking as viable modes of transport. Major roads and highways connect Winchester to neighboring cities and towns, facilitating easy travel for commuters. The city is also accessible by ride-sharing services, which complement the existing transportation options.
The community is served by a number of public schools, including elementary, middle, and high schools, as well as private educational institutions that offer additional choices for residents. Healthcare services in Winchester include a local hospital equipped with emergency and specialized care. The city also features a public library system that supports lifelong learning. Retail and dining options in Winchester reflect the local culture, with a variety of shops and restaurants that range from traditional to contemporary offerings.
Winchester is celebrated for its small-town charm and community-oriented atmosphere. The city prides itself on its rich history and cultural heritage, which is evident in its well-preserved downtown area and annual events that bring residents together. The community's character is further enhanced by local parks and recreational facilities that serve as gathering spots for families and friends.
Winchester's housing market offers a blend of architectural styles, with single-family homes being a significant part of the landscape. The area features a mix of modern, ranch-style, and colonial homes, reflecting the community's diverse architectural tastes. While the majority of the housing stock consists of single-family residences, there is also a selection of apartments and townhouses that cater to different lifestyle needs. The housing development in Winchester has seen various phases, with a notable number of properties dating back to the mid-20th century.
About 363 S Main St
The listing price of 363 S Main St property is $259,000.
The property 363 S Main St is a house located in Winchester, Kentucky, 40391.
Active Listing: 363 S Main St is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 363 S Main St are: Shearer Elementary School (GreatSchools Rating 3/10), Justice Elementary School (GreatSchools Rating 4/10), Conkwright Elementary School (GreatSchools Rating 3/10), Robert D. Campbell Junior High School (GreatSchools Rating 4/10), Edythe J. Hayes Middle School (GreatSchools Rating 8/10), McNabb Middle School (GreatSchools Rating 3/10), Phoenix Academy (GreatSchools Rating 1/10), George Rodgers Clark High School (GreatSchools Rating 4/10), Montgomery County High School (GreatSchools Rating 4/10).
According to the records, the last property tax for 2023 is $1,374 (source: MLS/based on county public records data).
The property at 363 S Main St has 3 bedrooms and 2 bathrooms.
The year of construction for 363 S Main St is 1940.
This home is located at 363 S Main St in Winchester, KY and zip code 40391. Features: 3 bedrooms, 2 bathrooms. It has been listed on Rocket Homes since May 5, 2025 and is currently priced at $259,000.
Over 5 listings were sold over their listed price in April 2025 in Winchester, KY. In the same period over 25 listings were sold below the listed price and 9 listings were sold for the listed price. The number of homes for sale in Winchester, KY increased by 17.2% between March and April 2025. In April 2025, listings were on the market for 59 days. During the same period, the median list price in this real estate market was $240,000.
From Rocket Homes Real Estate and based on county public records data.