For Sale
Price CutPrice Drop: $1K (10/08)
Single family home for sale at 59 Hillcrest Dr, Winchester, KY 40391 | MLS# 26020680 | Listing updated on 2026-10-08
Photo 1 of Single family home for sale at 59 Hillcrest Dr, Winchester, KY 40391 | MLS# 26020680 | Listing updated on 2026-10-08
Photo 2 of Single family home for sale at 59 Hillcrest Dr, Winchester, KY 40391 | MLS# 26020680 | Listing updated on 2026-10-08
Photo 3 of Single family home for sale at 59 Hillcrest Dr, Winchester, KY 40391 | MLS# 26020680 | Listing updated on 2026-10-08
Photo 4 of Single family home for sale at 59 Hillcrest Dr, Winchester, KY 40391 | MLS# 26020680 | Listing updated on 2026-10-08
8+
Beds Icon

Street View

$249,000

Monthly Est:$1,239

  • Beds Icon4 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,996sqft

59 Hillcrest Dr, Winchester, KY 40391

$1,239/moEst:

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  • 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 Lexington Bluegrass AOR (Imagine) MLS-KY

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Clark County

  • City

    Winchester

  • 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

DateEventPrice

09/29/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26020680

Pending

$249,000

$125/sqft

09/29/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26020680

Listed for Sale

$249,000 -0.40%

$125/sqft

09/04/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26020680

Price Decreased

$250,000 -2.34%

$125/sqft

09/01/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26020680

Listed for Sale

$256,000 -0.78%

$128/sqft

08/11/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26020680

Pending

$258,000 -0.77%

$129/sqft

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Nearby Homes

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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