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Street View
$455,000
Monthly Est:$2,265
8 Beds
- 4 Baths
4 full baths
5,058sqft
265 S Highland St, Winchester, KY 40391
$455,000
$2,265/moEst:
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Quadruplex
Built in 1940
$-- HOA
0.14 acre lot
$90/sq.ft
Description
Fully stabilized and 100% occupied, this is a quality 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 5058 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 f...
Continue Reading- Houzeo last checked: 7 minutes ago
- Listing updated: September 22, 2026 at 12:09 pm
- Listing Provided by: J Corey Griffo (502) 804-7067 | RE/MAX Elite Lexington (859) 245-1165
- Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26004961

Part of
Property Details
Status
Active
Type
Multi Family
No. of Stories
2
County
City
Neighborhood
--
Year Built
1940
HOA Fees
-
Finished Area
5,058 sqft
Lot Size
0.14 acre lot
Basement Area
- sqft
MLS Name
Lexington Bluegrass AOR (Imagine) MLS
MLS Number
26004961
MLS Status
Active
Days on Market
42
Cumulative Days on Market
183

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Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 8
Bathrooms: 4
Interior
Cooling
Central Air
Heating
Electric
Construction
Year Built
Year Built: 1940
Home type
Quadruplex
Roof
Shingle
Utilities & Energy
Laundry Features
Electric Dryer Hookup, Washer Hookup
Parking Features
Off Site
Other Features
Subdivision Name
Downtown
Price History
| Date | Event | Price |
|---|---|---|
07/17/2026 Source: | Price Decreased | $455,000 -5.01% $90/sqft |
04/12/2026 Source: | Price Decreased | $479,000 -5.15% $95/sqft |
03/14/2026 Source: | Listed for Sale | $505,000 $100/sqft |
03/14/2026 Source: | Price Increased | $505,000 +50.97% $100/sqft |
10/24/2021 Source: | Price Increased | $334,500 +271.67% $66/sqft |
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Based on information from the IMAGINE MLS® through Sep 23, 2026, 05:30AM. Copyrighted by the Imagine MLS®. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data on this website is deemed reliable but is not guaranteed accurate by the MLS. © 2026 IMAGINE MLS®. All Rights Reserved.
Advertising Broker: Donna Mink | Mink Realty
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