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Turn-Key Quadplex Income Property
For Sale
$455,000

265 S Highland Street, Winchester, KY 40391

MULTI_FAMILY - Winchester, KY

Property Size5,058 SF
Lot Size0.14 Acres
Price / SF$89.96
Days on Market143

Property Features for 265 S Highland Street

General Information

Property type Residential Multi Family
Property subtype Quadruplex
Zoning description R-1C
Bedrooms 8
Bathrooms 4
Full bathrooms 4
Rooms Bedroom 7, Bathroom 4, Bedroom 1, Bedroom 4, Bedroom 5, Bedroom 6, Bedroom 2, Bedroom 8, Bedroom 3, Bathroom 1, Laundry Room, Bathroom 2, Bathroom 3
Parking features Offsite
Subdivision Downtown
Elementary school Conkwright
Middle school Robert Campbell
High school GRC
Elementary school district Clark County - 7
Middle school district Clark County - 7
High school district Clark County - 7
Directions Take Lexington Ave east through town, and turn right on South Highland. Home is on the left.
Standard status Active
APN 054-4004-023-00
Size 5,058 SF
Lot size 0.14 Acres

Utilities

Heating system Electric (Heating)
Cooling system Central Air

Building Details

Year built 1940
Floors in Building 2
Number of units 4
Roof type Shingle
Listing Agency: RE/MAX Elite Lexington · RE/MAX International
Listed By: J Corey Griffo · License #70549
Added: Mar 12 Changed: Jul 17 Last Checked: Aug 1 at 8:06AM
MLS# 26004961

Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Investment Insights

Based on property information with market context.

This turn-key quadplex offers four residential units, each featuring two bedrooms, one bathroom, a full kitchen, and its own private laundry area. The property has been updated throughout and is described as clean and well-maintained, ready for new tenants.

The quadplex is located at 265 S Highland Street in Winchester, Kentucky, in the downtown area near shopping, dining, and local amenities.

Utilities are separately metered, and the overall configuration provides a total of eight bedrooms and four bathrooms across approximately 5,058 square feet.

Key Highlights

  • Downtown Winchester quadplex built in 1940 with approximately 5,058 SF total
  • 8 bedrooms and 4 bathrooms total across the four units
  • Each unit offers 2 bedrooms, 1 bathroom, a full kitchen, and private laundry area

Financial Insights For Apartment 5plus

Simulate Cap Rate and NOI

NOI Build-Up
Vacancy
income lost from leasable area expected to sit empty during the year — subtracted from gross rent.
EGI (Effective Gross Income)
gross rent minus vacancy losses — the realistic income before paying operating costs.
OpEx (Operating Expenses)
recurring costs to operate the property (property tax, insurance, utilities, maintenance, management) — excludes financing and capital improvements.
NOI (Net Operating Income)
income a property generates after operating costs but before financing and taxes.

Component $ $/SF
Gross rent $73.4k $14.52
− Vacancy −$3.2k −$0.64
EGI $70.2k $13.88
− OpEx −$31.6k −$6.25
NOI $38.6k $7.63
5,058 SF · lease $14.52/SF/yr · vacancy 4.40% · expense 45.00%

Alternative Uses

Best Use
Multifamily LT 5
$616.5K
$539.4K – $719.2K (±1% cap)
NOI $43,154 @ 7.0% cap · market cap 9.48%
Second Best
Apartment 5plus
$551.7K
$482.7K – $643.6K (±1% cap)
NOI $38,616 @ 7.0% cap · market cap 8.49%
Theoretical Best
Office A
$1.28M
$1.12M – $1.50M (±1% cap)
NOI $89,733 @ 7.0% cap · market cap 19.72%
Zoning and permitted uses should be independently verified with authorities.

Property Analytics

Current Use

Quadplexes

Suggested Use

Top Pick Dental Office Real Estate Agency Spa & Massage Center Skin Care Clinic HVAC Service (Bike/Boat/Book/etc) Store

Score = modeled unmet demand for each use within ~1 mi (higher = bigger opportunity). Zoning and permitted uses should be independently verified with local authorities.

Lease Details

4
Residential units
Multi-tenant
Tenancy
Turnkey business
Opportunity

Location Intelligence

Trade Area within ½ mile

613
Businesses Nearby

Demographics for 40391, KY

36,461
Population
16,125
Households
2.3
Avg Household Size
41
Median Age
22%
College-Educated
90%
High-School Grad
237.3 sq mi
ZIP Area
154
Density / Sq Mi
$67,910
Median Household Income
$40,323
Median Earnings
$884
Median Rent
$197,200
Median Home Value

Market

Vacancy Rate% for Multifamily in South region

8.5% 2022
10.2% 2023
11.4% 2024
11.3% 2025
Rey
Questions? Ask Rey
Realmo’s AI knows this listing — price, zoning, demand, history. Ask anything.

Frequently Asked Questions

What type of property is this?
Quadplex - Updated quadplex with four two-bedroom units, each with a private laundry area and separately metered utilities.
Where is this quadplex located?
The property is located at 265 S Highland Street Winchester, KY.
What is the asking price?
The asking price for this property is $455,000.
What are key features of this property?
This property features: Downtown Winchester quadplex built in 1940 with approximately 5,058 SF total; 8 bedrooms and 4 bathrooms total across the four units; Each unit offers 2 bedrooms, 1 bathroom, a full kitchen, and private laundry area
More about this property
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