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Street View
$249,000
Monthly Est:$1,239
4 Beds
- 2 Baths
2 full baths
1,996sqft
59 Hillcrest Dr, Winchester, KY 40391
$249,000
$1,239/moEst:
Get Pre-Approved
Single Family Residence
Built in 1966
$-- HOA
0.25 acre lot
$125/sq.ft
Description
PRICED TO SELL! 5.5% assumable mortgage! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant equity! Key Highlights: Potential Mother-in-Law Suite: The fully finished, remodeled lower level includes a full bath, separate living area, dedicated laundry, its own entrance, and a non-conforming 4th bedroom (or ideal home office/hobby room)—offering the perfect layout for a mother-in-law suite, guest quarters, or independent living space. New HVAC! Original Hardwood Floors: Character and potential await! Classic original hardwood flooring runs through the main level, begging to be refinished to showcase its natural warmth and beauty. Expansive Yard Space: Enjoy outdoor freedom on a huge lot! Featuring a spacious, fully fenced back yard with endless possibilities for play, pets, or entertaining. Versatile Layout: Upstairs main-level living area combined with a versatile basement setup to suit any household's needs. Walk out basement provides seperate entrances to each level. Location & Value: Nestled in an established neighborhood in winchester, moments from GRC, and quick access to Lexington and Richmond! Opportunities with this much space, flexible living arrangements, and upside don't last long—bring all reasonable offers! Agent is owner.
- Houzeo last checked: 7 minutes ago
- Listing updated: October 8, 2026 at 1:07 pm
- Listing Provided by: Dylan Langdon (859) 940-8552 | The Agency (859) 285-0614
- Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26020680

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1966
HOA Fees
-
Finished Area
1,996 sqft
Lot Size
0.25 acre lot
Basement Area
- sqft
MLS Name
Lexington Bluegrass AOR (Imagine) MLS
MLS Number
26020680
MLS Status
Active
Days on Market
2
Cumulative Days on Market
67

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 2
Interior
Sewer
Public Sewer
Window Features
Blinds
Cooling
Electric
Flooring
Carpet, Hardwood, Tile
Heating
Forced Air, Natural Gas
Appliances
Cooktop, Dishwasher, Dryer, Microwave, Oven, Refrigerator, Washer
Construction
Year Built
Year Built: 1966
Home type
Single Family Residence
Roof
Composition
Architectural Style
Ranch
Foundation Details
Block
Construction Materials
Brick Veneer
Utilities & Energy
Laundry Features
Electric Dryer Hookup, Main Level, Washer Hookup
Water Source
Public
Basement
Concrete, Finished, Full, Walk Out Access
Utilities
Electricity Connected, Natural Gas Connected, Water Connected
Parking Features
Attached Garage, Driveway
Other Features
Subdivision Name
Lyndale
Lot Features
Few Trees
Patio And Porch Features
Patio
Price History
| Date | Event | Price |
|---|---|---|
09/29/2026 Source: | Pending | $249,000 $125/sqft |
09/29/2026 Source: | Listed for Sale | $249,000 -0.40% $125/sqft |
09/04/2026 Source: | Price Decreased | $250,000 -2.34% $125/sqft |
09/01/2026 Source: | Listed for Sale | $256,000 -0.78% $128/sqft |
08/11/2026 Source: | Pending | $258,000 -0.77% $129/sqft |
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Based on information from the IMAGINE MLS® through Oct 10, 2026, 09:15PM. 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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