265 S Highland Street Winchester, KY $ 505,000
265 S Highland Street
$ 505,000
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265 S Highland Street

Winchester, KY, 40391
$ 505,000
Bedrooms8 Baths4.0 Sq 5,058

Monthly Estimate*

$ 3,109

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Multi-Family Home for sale in Winchester, KY

for $505,000 with 8 bedrooms and 4 full baths. This 5,058 square foot home was built in 1940 on a lot size of 0.14.

Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8 bedrooms, 4 bathrooms, and approximately 4,750 square feet, this property provides strong rental potential in a convenient location close to downtown shopping, dining, and local amenities. The units are clean, well-maintained, and ready for new tenants, making this an excellent option for investors seeking a solid income-producing property. Schedule your showing today before this opportunity is gone!

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Multi-Family Active

Price

$ 505,000

Bedrooms

8

Full Bath

4

Property Type

Multi-Family

Taxes

$ 0

Style

Quadruplex

Lot Size

0.14

Year Built

1940

Town/City

Winchester

County/Region

Clark

MLS | Web ID

26004961

Features
General
Heating Electric
Cooling Central Air
Possession Close Of Escrow Rental Agreement
Roof Shingle
Year Built 1940
Property Subtype Quadruplex
Parcel Number 054-4004-023-00
County Clark
New Construction N
Property Type Residential Income
Attached Garage N
Subdivision Name Downtown
Full Baths 4
Status Active
Directions Take Lexington Ave east through town and turn right on South Highland. Home is on the left.
High School GRC
City Winchester
High School District Clark County - 7
Zoning Description R-1C
Number Of Units Total 4
MLS Area 007 - Clark County
Lot Size Units Acres
Lot Size Square Feet 6098.0
Elementary School Conkwright
Land Lease Y/N N
Middle/Junior High School Robert Campbell
MLS Area Minor 007 - Clark County
Lease Considered Y/N N
Rent Control Y/N N
Structure Type Quadruplex
Standard Status Active
Senior Community None
Water Body Access Y/N None
Accessibility Features Y/N None
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Exterior
Parking Features Off Site
Lot Size Area 0.14
Number of Buildings 1
Building Area Total 5058.0
Lot Size Acres 0.14
Crops Included Y/N N
Irrigation Water Rights Y/N N
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Interior
Total Stories 2
Air Conditioning Y/N Y
Heating Y/N Y
Half Baths 0
Laundry Features Electric Dryer Hookup Washer Hookup
Total Bedrooms 8
Total Baths 4
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Internal Only
Street Number 1 265
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* Excluded Features
List By
Re/Max Elite Lexington

Broker

Affordability Calculator

$3,109
Per Month
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Monthly Principal & Interest
$3,109
Monthly Property Taxes
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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
3289754 Elementary School
3291684 Middle School
GRC High School High School
Pricing History
DatePricePrice ChangeDescription
3/14/2026$505,000 Listed Price

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265 S Highland Street, Winchester, KY, 40391 is a Multi-Family Home for sale at $505,000 with 5,058 sqft and a lot size of 0.14. 265 S Highland Street has 8 bedrooms, 4.0 baths, and was built in 1940. The property's zip code is 40391 which is in Winchester, KY