Winchester, KY homes for sale & real estate

6 hours on Rocket

$3,858 Closing Credit¹

$324,900

4 beds • 2.5 baths

816 Stratton Ln, Winchester, KY 40391

#25012215, Listing office: Dream Maker Realty, LLC

1 day on Rocket

$4,720 Closing Credit¹

$397,500

3 beds • 4 baths

399 Stonecrest Rd, Winchester, KY 40391

#25012164, Listing office: HomeFirst Real Estate

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1 day on Rocket

$2,494 Closing Credit¹

$210,000

3 beds • 2 baths

2858 Ford Hampton Rd, Winchester, KY 40391

#25012156, Listing office: Dream Maker Realty, LLC

1 day on Rocket

$2,303 Closing Credit¹

$193,900

3 beds • 2 baths

507 Hidden Hills Way, Winchester, KY 40391

#25012154, Listing office: Taylor Real Estate, LLC

175 Chatham Pl, Winchester, KY 40391 - view of miscellaneous document

3 days on Rocket

$5,646,000

2 beds • 2 baths • 37,192 sqft

175 Chatham Pl, Winchester, KY 40391

#25012023, Listing office: Milton and Associates Real Estate

4 days on Rocket

$2,611 Closing Credit¹

$219,900

4 beds • 2 baths

517 Acadia Way, Winchester, KY 40391

#25011839, Listing office: The Brokerage

5 days on Rocket

$2,601 Closing Credit¹

$219,000

3 beds • 1 bath

110 Colonial Park Dr, Winchester, KY 40391

#25011770, Listing office: Kentucky Residential Real Estate, LLC

Room to negotiate?

Median Sold Price

$238.3K

Avg. Sale Time

43 Days

Based on our May 2025 Market Report.

5 days on Rocket

$3,264 Closing Credit¹

$274,900

3 beds • 2 baths

528 Estes Dr, Winchester, KY 40391

#25010993, Listing office: Freedom Realty & Property Management

5 days on Rocket

$6,828 Closing Credit¹

$575,000

5 beds • 3 baths

594 Earlymeade Dr, Winchester, KY 40391

#25011592, Listing office: Coldwell Banker McMahan

5 days on Rocket

$2,611 Closing Credit¹

$219,900

3 beds • 1 bath

40 Garner St, Winchester, KY 40391

#25011691, Listing office: Guide Realty, Inc.

7 days on RocketBackup offers

$3,088 Closing Credit¹

$260,000

3 beds • 1.5 baths

609 Clintonville Rd, Winchester, KY 40391

#25011586, Listing office: Bridgewater Real Estate

7 days on Rocket

$10,000 Closing Credit¹

$2,150,000

3 beds • 5 baths

27 Sundown Ln, Winchester, KY 40391

#25011536, Listing office: Bluegrass Sotheby's International Realty

$3,205 Closing Credit¹

$269,900

5 beds • 3 baths

400 Verna Dr, Winchester, KY 40391

#25011266, Listing office: RE/MAX Elite Realty

$2,731 Closing Credit¹

$230,000

3 beds • 2.5 baths

412 Paisley Ct, Winchester, KY 40391

#25011446, Listing office: Bluegrass Properties Group

$3,086 Closing Credit¹

$259,900

3 beds • 2 baths

302 April Way, Winchester, KY 40391

#25011454, Listing office: The Agency

$7,119 Closing Credit¹

$599,500

4 beds • 2 baths

102 Bella Shae Way, Winchester, KY 40391

#25011310, Listing office: Keller Williams Commonwealth

$2,672 Closing Credit¹

$225,000

3 beds • 1 bath

26 Stefanie Ct, Winchester, KY 40391

#25011235, Listing office: Coldwell Banker McMahan

Tour

$4,689 Closing Credit¹

$394,900

3 beds • 2 baths

101 Dorset Ln, Winchester, KY 40391

#25011163, Listing office: Freedom Realty & Property Management

$4,511 Closing Credit¹

$379,900

3 beds • 2.5 baths

309 Gallahadion Ct, Winchester, KY 40391

#25011164, Listing office: Freedom Realty & Property Management

$3,563 Closing Credit¹

$300,000

3 beds • 2 baths

110 Albany Ln, Winchester, KY 40391

#25010989, Listing office: Kentucky Residential Real Estate, LLC

Backup offers

$2,314 Closing Credit¹

$194,900

3 beds • 2 baths

502 Corley Ln, Winchester, KY 40391

#25010776, Listing office: Plum Tree Realty

$3,444 Closing Credit¹

$290,000

4 beds • 2 baths

2832 Two Mile Rd, Winchester, KY 40391

#25010801, Listing office: Keller Williams Commonwealth

Backup offers

$3,485 Closing Credit¹

$293,500

4 beds • 3 baths

13 Shelley Dr, Winchester, KY 40391

#25010751, Listing office: Keller Williams Legacy Group

$45,000

Land • 0.36 Acres

434 Fairholme Way, Winchester, KY 40391

#25010710, Listing office: JL Realty Group, LLC

$5,902 Closing Credit¹

$497,000

4 beds • 4 baths

150 Stone Crest Rd, Winchester, KY 40391

#25010625, Listing office: Murphy Realty Group

$4,033 Closing Credit¹

$339,600

4 beds • 2.5 baths

402 Mcdowell Dr, Winchester, KY 40391

#25010573, Listing office: FC Tucker Bluegrass

Backup offers

$2,316 Closing Credit¹

$195,000

3 beds • 1 bath

113 Colonial Park Dr, Winchester, KY 40391

#25010561, Listing office: Kentucky Land and Home

$95,000

Land • 1.09 Acres

1700 Mcclure Rd, Winchester, KY 40391

#25010530, Listing office: Ensor Real Estate, LLC

$135,000

Land • 10.27 Acres

4150 Schollsville Rd, Winchester, KY 40391

#25010524, Listing office: Ensor Real Estate, LLC

Backup offers

$2,374 Closing Credit¹

$199,900

3 beds • 1.5 baths

139 W Hickman St, Winchester, KY 40391

#25010184, Listing office: ERA Select Real Estate

Backup offers

$2,316 Closing Credit¹

$195,000

3 beds • 1 bath

114 Sunset Hts, Winchester, KY 40391

#25010224, Listing office: Rector Hayden Realtors

$7,719 Closing Credit¹

$650,000

3 beds • 3 baths

2085 Hancock Valley Dr, Winchester, KY 40391

#25010192, Listing office: Premier Property Consultants

$2,078 Closing Credit¹

$175,000

4 beds • 1 bath

81/2 1st St, Winchester, KY 40391

#25010139, Listing office: Lifstyl Real Estate

Backup offers

$2,482 Closing Credit¹

$209,000

3 beds • 2 baths

138 Linden Ave, Winchester, KY 40391

#25010061, Listing office: HomeLand Real Estate Inc - Mt Sterling

439 Old Muddy Creek Rd, Winchester, KY 40391

$129,900

Land • 6.79 Acres

439 Old Muddy Creek Rd, Winchester, KY 40391

#25009969, Listing office: Tom Goebel & Company

Backup offers

$3,563 Closing Credit¹

$300,000

3 beds • 2 baths

1740 Oil Springs Rd, Winchester, KY 40391

#25009451, Listing office: Marshall Lane Real Estate - Lexington

$1,888 Closing Credit¹

$159,000

2 beds • 2 baths

125 Chatham Pl, Winchester, KY 40391

#25009926, Listing office: Milton and Associates Real Estate

Backup offers

$1,186 Closing Credit¹

$99,900

2 beds • 2 baths

27 Oliver St, Winchester, KY 40391

#25009880, Listing office: Metro Max Realty

$69,000

Land • 0.42 Acres

435 Fairholme Way, Winchester, KY 40391

#25009846, Listing office: Coldwell Banker McMahan

Backup offers

$8,253 Closing Credit¹

$695,000

4 beds • 3.5 baths

357 Wades Mill Rd, Winchester, KY 40391

#25009821, Listing office: Rector Hayden Realtors

Winchester, KY Real Estate Market Overview

There are 148 homes for sale in Winchester, KY. The following market insights reflect all property types in the Winchester, KY real estate market. The inventory of homes for sale in Winchester, KY between April 2025 and May 2025 increased by 1.6%. The median list price of listings available in May 2025 was $238,333, while the average time on the real estate market was 43 days. Over 5 listings were sold over their listed price in May 2025 in Winchester, KY. In the same period over 19 listings were sold below the listed price and 17 listings were sold for the listed price.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Winchester, KY

Overview

Winchester is located in Clark County, Kentucky. There are roughly 11,274 residents, living in 4,757 households. The average temperature for Winchester this time of the year is low of 61F and high of 84F. On average, Winchester gets about 4.31 inches of precipitation in June. Most residents are home owners (53%), have a high school diploma (59%) and are single, no kids (47%).

Data provided by Home Junction

Housing types

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.

Advantages

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.

Convenience

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.

Transportation

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.

Schools near Winchester, KY

Elementary Schools

Conkwright Elementary School
360 Mount Sterling Rd
Public District KG-4
Shearer Elementary School
244 E Broadway St
Public District KG-4
Henry E. Baker Intermediate School
1645 Martin Luther King Jr Dr
Public District 5-6

Middle Schools

Robert D. Campbell Junior High School
620 Boone Ave
Public District 7-8

High Schools

Phoenix Academy
100 Vaught Rd
Public District 6-12

Data provided by Great Schools

Homes for sale in Winchester, KY

Winchester, KY Real Estate Market Overview

What is it like to live in Winchester, KY

Overview

Housing types

Advantages

Convenience

Transportation

Explore popular home types in Winchester, KY

Related homes in Winchester, KY

Schools near Winchester, KY

Housing market reports in Clark County

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