?
  • Chat with Us
  • Submit Feedback
  • TopHap Academy
  • What's New?
Residential > House
Pending
List Price
$188,900$114/ft²

27 Ashland Ave
Winchester, KY 40391

  • Photo 0
  • Photo 1
  • Photo 2
  • Photo 3
  • Photo 4
  • Photo 5
  • Photo 6
  • Photo 7
  • Photo 8
  • Photo 9
  • Photo 10
  • Photo 11
  • Photo 12
  • Photo 13
  • Photo 14
  • Photo 15
  • Photo 16
  • Photo 17
  • Photo 18
  • Photo 19
  • Photo 20
  • Photo 21
  • Photo 22
  • Photo 23
  • 27 Ashland Ave, Winchester, KY 40391 is a 3 bed, 2 bath, 1,653 ft² house built in 1950 on a 0.474 acre lot. This house is currently pending. The latest TopHap estimate of the house's value is $199,882.

    Property Valuations

    Latest estimates for 27 Ashland Ave based on TopHap automated valuation model (AVM).

    MLS Description

    The listing agent's description. Original Listing

    Motivated Seller! Move right in and enjoy this well-maintained 3-bed, 2-bath ranch in the heart of Massie Addition! Thoughtfully updated with a recent roof on both the home and garage, a brand-new hot water heater (2025), and a modern, fresh interior paint palette, this home is ready for you. A home warranty covering all major systems and appliances is included for added peace of mind. This stately older home has many original features, adding to its timeless character and charm. The generous ~half-acre lot offers room to garden, play, or relax under the trees, while the detached 2-car garage provides excellent storage and parking. With everything on one level and just a short stroll to downtown Winchester's refreshed shops, dining, and year-round events, this property is ready for its next chapter.

    Listing Agents

    The listing agent for 27 Ashland Ave is Robin Mobley-Mosher.

    Current Ownership

    Information about the current owner(s).

    Property History

    27 Ashland Ave has undefined property events records (listings, deeds, permits, tax, foreclosure, loan).

    Property Events

    Environment

    Environmental factors around 27 Ashland Ave

    School Information

    Public/private schools serving 27 Ashland Ave

    Neighborhood

    This property is located in 40391.

    Market Trends

    Historical market data near 27 Ashland Ave over selected time period.

    Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

    Nearby Properties on Ashland Ave