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 4 | 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

111 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 111 Listings

Map

23 of 111 Listings

Price Reduced31

Homes for Sale in Winchester, KY

Hide Map

23 of 111 Listings

Map

Homes for Sale in Winchester, KY

23 of 111 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced31

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Active

$275,000

3 bd · 2 ba · 1,512 sqft

4305 Old Boonesboro Road, Winchester, KY

Brenda H Sipes · WEICHERT REALTORS - ABG Properties

Price Reduced25Active

$159,000

3 bd · 1 ba · 1,249 sqft

209 E Washington Street, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

Price Reduced19Active

$299,500

3 bd · 3 ba · 2,592 sqft

135 E Broadway Street, Winchester, KY

Dale Hatton · Dream Maker Realty, LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

Price Reduced18Active

$349,000

3 bd · 2 ba · 1,990 sqft

11 Stoney Brook Drive 1, Winchester, KY

Garry H Milton · Milton and Associates Real Estate

40Active

$244,000

3 bd · 2 ba · 1,692 sqft

54 Locust Drive, Winchester, KY

Natalie Avant · Berkshire Hathaway HomeServices Foster Realtors

63Active

$785,000

5 bd · 3 ba · 4,676 sqft

217 Wades Mill Road, Winchester, KY

Michelle R Blackburn · RE/MAX Creative, Winchester

21Active

$135,000

2 bd · 1 ba · 807 sqft

3208 Ford Hampton Road, Winchester, KY

Bob Sophiea · eXp Realty, LLC

Price Reduced50Active

$629,000

5 bd · 4 ba · 5,011 sqft

104 Teal Lane, Winchester, KY

The Gooch Team - Kristy Gooch · RE/MAX Elite Realty

73Active

$1,400,000

4 bd · 4 ba · 5,613 sqft

1400 Craig Crossing, Winchester, KY

Ken Ritter · Coldwell Banker McMahan

65Active

$359,900

3 bd · 2 ba · 2,269 sqft

15 Moundale Avenue, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

28Active

$365,900

3 bd · 2 ba · 1,558 sqft

204 Jett Drive, Winchester, KY

Mila J Ensor · Ensor Real Estate, LLC

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 Reduced23Active

$199,900

2 bd · 1 ba · 1,154 sqft

606 College Street, Winchester, KY

Alyssa Ryan · Marshall Lane Real Estate - Lexington

Price Reduced27Active

$265,000

3 bd · 2 ba · 1,776 sqft

15 Kittison Drive, Winchester, KY

Cheri Shaffer · Lifstyl Real Estate

Price Reduced72Active

$544,900

5 bd · 4 ba · 3,741 sqft

130 Winterberry Circle, Winchester, KY

Joshua Wood · Freedom Realty & Property Management

75Active

$385,000

3 bd · 2 ba · 1,344 sqft

2725 Goshen Road, Winchester, KY

Christa Joynt · Keller Williams Commonwealth

Price Reduced61Active

$379,000

3 bd · 3 ba · 2,204 sqft

322 Calmes Boulevard, Winchester, KY

Darrell Tackett · Dream Maker Realty, LLC

Price Reduced55Active

$349,000

4 bd · 2 ba · 3,306 sqft

351 Boone Avenue, Winchester, KY

James Woodrum · RE/MAX Creative, Winchester

64Active

$524,900

3 bd · 3 ba · 2,514 sqft

275 Runnymeade Drive, Winchester, KY

Craig R Bridgewater · Bridgewater Real Estate

Price Reduced64Active

$415,000

3 bd · 2 ba · 2,027 sqft

187 Hawthorne Drive, Winchester, KY

Christa Joynt · Keller Williams Commonwealth

46Active

$749,900

3 bd · 3 ba · 2,735 sqft

2180 Big Stoner Road, Winchester, KY

Ashley Barreto · Indigo & Co

1…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 (300)
40509 (158)
40391 (111)
40515 (109)
40353 (92)
40511 (87)
40324 (73)
40517 (72)

Cities

Lexington (741)
Richmond (300)
Mount Sterling (91)
Georgetown (73)
Nicholasville (65)
Paris (54)
Irvine (42)
Stanton (39)

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #221881

Call Thomas

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, 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

Nearby areas

ZIP codes

40475 (300)
40509 (158)
40391 (111)
40515 (109)
40353 (92)
40511 (87)
40324 (73)
40517 (72)

Cities

Lexington (741)
Richmond (300)
Mount Sterling (91)
Georgetown (73)
Nicholasville (65)
Paris (54)
Irvine (42)
Stanton (39)

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.