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Street View
$165,000
Monthly Est:$821
4 Beds
- 3 Baths
3 full baths
3,462sqft
229 S Highland St, Winchester, KY 40391
$165,000
$821/moEst:
Get Pre-Approved
Single Family Residence
Built in 1930
$-- HOA
0.11 acre lot
$48/sq.ft
Description
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.
- Houzeo last checked: 7 minutes ago
- Listing updated: July 7, 2026 at 4:35 pm
- Listing Provided by: Michelle R Blackburn (859) 707-5955 | RE/MAX Creative, Winchester (859) 422-2000
- Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26008701

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1930
HOA Fees
-
Finished Area
3,462 sqft
Lot Size
0.11 acre lot
Basement Area
- sqft
MLS Name
Lexington Bluegrass AOR (Imagine) MLS
MLS Number
26008701
MLS Status
Active
Days on Market
171
Cumulative Days on Market
76

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 3
Interior
Cooling
Electric
Heating
Forced Air, Natural Gas
Flooring
Hardwood
Sewer
Public Sewer
Appliances
Refrigerator
Construction
Year Built
Year Built: 1930
Home type
Single Family Residence
Architectural Style
Colonial
Construction Materials
Wood Siding, Hardi Plank Type
Foundation Details
Stone
Roof
Metal
Utilities & Energy
Water Source
Public
Basement
Crawl Space, Interior Entry, Walk Out Access
Utilities
Electricity Connected, Natural Gas Connected, Water Connected
Parking Features
Basement, Garage Faces Side
Fireplace Features
Living Room
Other Features
Patio And Porch Features
Porch, Front Porch
Subdivision Name
South Park Addition
Price History
| Date | Event | Price |
|---|---|---|
04/22/2026 Source: | Price Increased | $180,000 +9.09% $52/sqft |
04/22/2026 Source: | Listed for Sale | $165,000 $48/sqft |
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Based on information from the IMAGINE MLS® through Oct 10, 2026, 10:15PM. 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.
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