221 S Highland Street Winchester, KY ^$ 248,900

221 S Highland Street

^$ 248,900

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221 S Highland Street

Winchester, KY, 40391

^$ 248,900

Bedrooms5 Baths3.0 Sq 3,007

Monthly Estimate*

^$ 1,533

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Multi-Family Home for sale in Winchester, KY

for $248,900 with 5 bedrooms and 3 full baths. This 3,007 square foot home was built in 1930 on a lot size of 0.16.

INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered together, landlord does cover utility expenses. Please call with any questions, please do not disturb the tenants!

Multi-Family Active

Price

^$ 248,900

Bedrooms

Full Bath

Property Type

Multi-Family

Taxes

^$ 0

Style

Triplex

Lot Size

0.16

Year Built

1930

Town/City

Winchester

County/Region

Clark

MLS | Web ID

26000780

Features

General

Heating Baseboard Electric Floor Furnace Other

Cooling Electric Window Unit(s)

Possession Close Of Escrow

Roof Shingle

Zoning R-1C

Year Built 1930

Property Subtype Triplex

Parcel Number 054-3012-016-00

County Clark

New Construction N

Property Type Residential Income

Subdivision Name Downtown

Full Baths 3

Status Active

Directions Main St. to S. Highland Park. Home will be on the left.

High School GRC

City Winchester

High School District Clark County - 7

Number Of Units Total 3

MLS Area 007 - Clark County

Lot Size Units Acres

Lot Size Square Feet 6970.0

Land Lease Y/N N

MLS Area Minor 007 - Clark County

Lease Considered Y/N N

Rent Control Y/N N

Structure Type Triplex

Standard Status Active

Senior Community None

Water Body Access Y/N None

Accessibility Features Y/N None

Exterior

Total Parking 5.0

Lot Size Area 0.16

Number of Buildings 1

Building Area Total 3007.0

Lot Size Acres 0.16

Crops Included Y/N N

Irrigation Water Rights Y/N N

Interior

Total Stories 1

Air Conditioning Y/N Y

Heating Y/N Y

Half Baths 0

Laundry Features Electric Dryer Hookup Washer Hookup

Total Bedrooms 5

Total Baths 3

Heating-Baseboard True

Internal Only

Street Number 1 221

* Excluded Features

List By

The Brokerage

Broker

josh@thebrokerageky.com

Affordability Calculator

$1,533

Per Month

Monthly Principal & Interest: $1,533
Monthly Property Taxes: --
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Multi-family listings in Winchester, KY

Average List Price ^$939,733

Percent of Sale Price 278%

About Winchester, KY

18,110 Population

2% Since 2002

^$39,988 Median Income

39.34 Median Age

23% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

5263982 Elementary School

4017217 Middle School

GRC High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
1/12/2026	$248,900		Listed Price

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221 S Highland Street, Winchester, KY, 40391 is a Multi-Family Home for sale at $248,900 with 3,007 sqft and a lot size of 0.16. 221 S Highland Street has 5 bedrooms, 3.0 baths, and was built in 1930. The property's zip code is 40391 which is in Winchester, KY

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Listing data provided courtesy of the Internet Data Exchange Program of Bluegrass REALTORS.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Bluegrass REALTORS. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is 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.

Data is updated as of 1/16/2026.

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221 S Highland Street

Multi-Family Home for sale in Winchester, KY

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