Safety & registry resources

Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

Winchester, KY Homes for Sale — Page 3 | Realty.com

Buy

Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Rentals
Commercial

115 listings

Registered offenders on the map

Show registered offenders

115 listings

Sell

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

Homes for Sale in Winchester, KY

Hide Map

23 of 115 Listings

Map

23 of 115 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced26Active
$229,900
3 bd · 2 ba · 1,904 sqft
528 Estes Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
Price Reduced29Active
$275,000
4 bd · 2 ba · 1,752 sqft
198 Hilltop Drive, Winchester, KY
Stephanie Hacker · Kentucky Residential Real Estate, LLC
65Active
$359,900
3 bd · 2 ba · 2,269 sqft
15 Moundale Avenue, Winchester, KY
Joshua Wood · Freedom Realty & Property Management

Price Reduced24Active
$219,900
3 bd · 1 ba · 1,100 sqft
125 Kittison Drive, Winchester, KY
Kathryn M Cheuvront · Coldwell Banker McMahan
Price Reduced12Active
$249,000
4 bd · 2 ba · 1,996 sqft
59 Hillcrest Drive, Winchester, KY
Dylan Langdon · The Agency
Price Reduced46Active
$169,000
2 bd · 2 ba · 1,100 sqft
148 Hidden Grove Lane, Winchester, KY
Kathryn M Cheuvront · Coldwell Banker McMahan
45Active
$484,900
4 bd · 3 ba · 2,381 sqft
410 Fairholme Way, Winchester, KY
Morgan Withrow · The Brokerage
7Active
$365,900
3 bd · 2 ba · 1,558 sqft
204 Jett Drive, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
Price Reduced23Active
$215,000
3 bd · 2 ba · 1,319 sqft
3 Nunnelly Court, Winchester, KY
Yasir Ahmed · Black Mountain Realty
24Active
$365,900
3 bd · 2 ba · 1,635 sqft
206 Jett Drive, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
Price Reduced32Active
$160,000
3 bd · 1 ba · 1,173 sqft
24 Spring Street, Winchester, KY
Jason L Szaks · EXIT Town & Country Realtors
Price Reduced56Active
$249,000
3 bd · 3 ba · 1,664 sqft
127 Bay Hill Drive, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
Price Reduced36Active
$78,500
3 bd · 1 ba · 1,152 sqft
16 Denny Avenue, Winchester, KY
Robin Trimble · HomeFirst Real Estate
Price Reduced23Active
$199,900
2 bd · 1 ba · 1,154 sqft
606 College Street, Winchester, KY
Alyssa Ryan · Marshall Lane Real Estate - Lexington
Price Reduced30Active
$140,000
2 bd · 1 ba · 630 sqft
108 Franklin Avenue, Winchester, KY
Cheri Shaffer · Lifstyl Real Estate
Price Reduced27Active
$265,000
3 bd · 2 ba · 1,776 sqft
15 Kittison Drive, Winchester, KY
Cheri Shaffer · Lifstyl Real Estate
Price Reduced19Active
$280,000
2 bd · 1 ba · 1,344 sqft
405 Nick Lane, Winchester, KY
Taylor Norton · McCallie Real Estate
Price Reduced22Active
$229,500
3 bd · 2 ba · 1,130 sqft
527 Hidden Hills Way, Winchester, KY
Jarran Thomas · The Agency
Price Reduced110Active
$699,000
4 bd · 5 ba · 4,255 sqft
132 Lana Lane, Winchester, KY
Rebecca J Harvey · Napier Realtors
Price Reduced72Active
$544,900
5 bd · 4 ba · 3,741 sqft
130 Winterberry Circle, Winchester, KY
Joshua Wood · Freedom Realty & Property Management
Price Reduced28Active
$226,900
3 bd · 2 ba · 1,665 sqft
106 Quail Ridge Road, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
Price Reduced17Active
$60,000
2 bd · 2 ba · 924 sqft
546 Constitution Drive, Winchester, KY
Dale Hatton · Dream Maker Realty, LLC
Price Reduced40Active
$289,900
4 bd · 3 ba · 1,970 sqft
428 Waycross Drive, Winchester, KY
Wayne Elkins · RE/MAX Creative Realty

1 2 3 4 5

Listing data & MLS disclosures

Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX 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. Real estate listings held by IDX brokerage firms other than Realty.com, 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. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

Winchester housing market

August 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 32 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 19, 2026

Median sale price: $315,000$218,000–$595,000 typical range
Price per sq. ft.: $173
Sales: 37
Paid in cash: 32.4%

Homes on the market · MLS, as of Aug 30, 2026

Median list price: $319,900
Homes for sale: 111

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 14.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,544 sq. ft.

Winchester, KY community profile

Population: 19,583
Median income: $57,052
Housing units: 9,262
People per sq. mi.: 81.2
Area: 241.2 sq. mi.

Source: HJN community data

Explore Winchester homes

By price

Homes Under $300K
Homes Under $400K
Homes Under $500K
Homes Under $600K
Homes Under $700K

By bedrooms

3 Bedroom Homes

Nearby areas

ZIP codes

40475 (296)
40509 (155)
40391 (115)
40515 (90)
40353 (79)
40502 (71)
40508 (71)
40517 (65)

Cities

Lexington (550)
Richmond (296)
Mt Sterling (78)
Paris (48)
Stanton (48)
Owingsville (31)
Berea (28)
Carlisle (28)

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

Imagine MLS (Bluegrass REALTORS): The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of Bluegrass REALTORS®. IDX 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. Real estate listings held by IDX brokerage firms other than Realty.com, 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. Copyright © 2026 Bluegrass REALTORS®. All Rights Reserved.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Winchester, KY community profile

Population: 19,583
Median income: $57,052
Housing units: 9,262
People per sq. mi.: 81.2
Area: 241.2 sq. mi.

Source: HJN community data

Winchester housing market

August 2026 · This period is still settling

Selling at 98.2% of asking price

Buyers here are paying below asking. MLS · 32 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 19, 2026

Median sale price: $315,000$218,000–$595,000 typical range
Price per sq. ft.: $173
Sales: 37
Paid in cash: 32.4%

Homes on the market · MLS, as of Aug 30, 2026

Median list price: $319,900
Homes for sale: 111

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 14.0%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,544 sq. ft.

Nearby areas

ZIP codes

40475 (296)
40509 (155)
40391 (115)
40515 (90)
40353 (79)
40502 (71)
40508 (71)
40517 (65)

Cities

Lexington (550)
Richmond (296)
Mt Sterling (78)
Paris (48)
Stanton (48)
Owingsville (31)
Berea (28)
Carlisle (28)