For Sale
Single family home for sale at 20 Jackson St, Winchester, KY 40391 | MLS# 26012820 | Listing updated on 2026-07-27
Photo 1 of Single family home for sale at 20 Jackson St, Winchester, KY 40391 | MLS# 26012820 | Listing updated on 2026-07-27
Photo 2 of Single family home for sale at 20 Jackson St, Winchester, KY 40391 | MLS# 26012820 | Listing updated on 2026-07-27
Photo 3 of Single family home for sale at 20 Jackson St, Winchester, KY 40391 | MLS# 26012820 | Listing updated on 2026-07-27
Photo 4 of Single family home for sale at 20 Jackson St, Winchester, KY 40391 | MLS# 26012820 | Listing updated on 2026-07-27
32+
Beds Icon

Street View

$265,000

Monthly Est:$1,319

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,650sqft

20 Jackson St, Winchester, KY 40391

$1,319/moEst:

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  • Single Family Residence

  • Built in 1940

  • $-- HOA

  • 0.12 acre lot

  • $161/sq.ft

Description

Beautifully updated and truly move-in ready, this 3-bedroom, 2-bath home blends timeless charm with modern convenience. Step inside to a spacious living room and an updated kitchen featuring abundant cabinetry, while original hardwood flooring, luxury vinyl plank, and stylish finishes create a warm and inviting atmosphere throughout. The versatile utility room provides the perfect space for a home office, playroom, hobby area, or additional storage. An unfinished basement offers endless potential for future expansion or extra storage. Outside, enjoy a fully fenced backyard, patio, covered front porch, and a detached two-car garage ideal for relaxing or entertaining. Major updates provide peace of mind and include the HVAC system, furnace, roof shingles, windows, vinyl siding, flooring, kitchen cabinetry, bathroom vanities, light fixtures, doors, and hardware. With all the hard work already completed, this home is ready for you to move in and make it your own.

  • Houzeo last checked: 12 hours ago
  • Listing updated: July 27, 2026 at 4:54 pm
  • Listing Provided by: Zova M Rothchild (859) 806-1992 , The Mateyoke Group - Jenny Mateyoke | Keller Williams Legacy Group (859) 544-6175
  • Source: Lexington Bluegrass AOR (Imagine) MLS-KY | MLS#: 26012820 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

    1940

  • HOA Fees

    -

  • Finished Area

    1,650 sqft

  • Lot Size

    0.12 acre lot

  • Basement Area

    - sqft

  • MLS Name

    Lexington Bluegrass AOR (Imagine) MLS

  • MLS Number

    26012820

  • MLS Status

    Active

  • Days on Market

    128

  • Cumulative Days on Market

    56

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 2

Interior

  • Sewer

    Public Sewer

  • Interior Features

    Eat In Kitchen

  • Appliances

    Dishwasher, Dryer, Gas Range, Refrigerator, Washer

  • Window Features

    Blinds

  • Flooring

    Tile, Wood

  • Cooling

    Ceiling Fan(s), Central Air

  • Heating

    Forced Air, Natural Gas

Construction

  • Year Built

    Year Built: 1940

  • Home type

    Single Family Residence

  • Roof

    Composition, Shingle

  • Foundation Details

    Block

  • Construction Materials

    Vinyl Siding

Utilities & Energy

  • Parking Features

    Detached Garage

  • Security Features

    Security System Owned

  • Water Source

    Public

  • Laundry Features

    Main Level

  • Basement

    Sump Pump, Unfinished

Other Features

  • Subdivision Name

    Downtown

  • Community Features

    Park

  • Patio And Porch Features

    Patio, Porch, Rear Patio, Front Porch

Price History

DateEventPrice

07/27/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26012820

Price Decreased

$265,000 -1.85%

$161/sqft

07/16/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26012820

Price Decreased

$270,000 -1.82%

$164/sqft

06/27/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26012820

Price Decreased

$275,000 -1.79%

$167/sqft

06/16/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26012820

Price Decreased

$280,000 -3.45%

$170/sqft

06/04/2026

Source: mls_logoLexington Bluegrass AOR (Imagine) MLS-KY #26012820

Listed for Sale

$290,000 +20.38%

$176/sqft

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Based on information from the IMAGINE MLS® through Oct 09, 2026, 02:30PM. 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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