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.
Sold for $188,000
$188,000
27 Ashland Ave, Winchester, KY 40391
3beds
1,653sqft
Single Family Residence
Built in 1950
0.47 Acres Lot
$190,900 Zestimate®
$114/sqft
$1,762 Estimated rent
Home value
$190,900
$147,000 - $246,000
$1,762/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Robin Mobley-Mosher 859-457-6074,
Marshall Lane Real Estate - Lexington
Bought with:
Katie Allen, 276201
Keller Williams Legacy Group
Source: Imagine MLS,MLS#: 25501148
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Description: 2nd room on left
- Level: Lower
- Area: 272.5 Square Feet
- Dimensions: 18.07 x 15.08
Bedroom 1
- Description: Right side of house
- Level: Lower
- Area: 201 Square Feet
- Dimensions: 15.17 x 13.25
Bedroom 2
- Description: Rear of house
- Level: Lower
- Area: 178.4 Square Feet
- Dimensions: 15.08 x 11.83
Primary bathroom
- Description: in primary bedroom
- Level: Lower
- Area: 37.36 Square Feet
- Dimensions: 8 x 4.67
Bathroom 1
- Description: in dining room
- Level: Lower
- Area: 46.74 Square Feet
- Dimensions: 4.92 x 9.5
Dining room
- Description: middle of house
- Level: Lower
- Area: 165.27 Square Feet
- Dimensions: 12.17 x 13.58
Foyer
- Description: Front entrance
- Level: Lower
- Area: 88.8 Square Feet
- Dimensions: 15 x 5.92
Kitchen
- Description: rear right
- Level: Lower
- Area: 164.04 Square Feet
- Dimensions: 13.67 x 12
Living room
- Description: Front left room
- Level: Lower
- Area: 222.35 Square Feet
- Dimensions: 15.25 x 14.58
Other
- Description: Primary Closet
- Level: Lower
- Area: 42 Square Feet
- Dimensions: 10.5 x 4
Other
- Description: Bedroom 2 closet
- Level: Lower
- Area: 15.63 Square Feet
- Dimensions: 4.08 x 3.83
Utility room
- Description: Laundry Room
- Level: Lower
- Area: 68.54 Square Feet
- Dimensions: 11.92 x 5.75
Heating
- Electric, Forced Air
Cooling
- Central Air, Ceiling Fan(s), Heat Pump
Appliances
- Included: Dishwasher, Microwave, Refrigerator, Range
- Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
Features
- Entrance Foyer, Walk-In Closet(s), Ceiling Fan(s)
- Flooring: Ceramic Tile, Vinyl
- Windows: Insulated Windows, Blinds
- Basement: Unfinished,Walk-Up Access
- Has fireplace: No
Interior area
- Total structure area: 1,653
- Total interior livable area: 1,653 sqft
- Finished area above ground: 1,653
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Detached Garage, Driveway, Off Street, Garage Faces Front
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: One
- Fencing: Chain Link,Partial,Wire
Lot
- Size: 0.47 Acres
- Features: Few Trees
Details
- Parcel number: LT13&14P/DB 056_406
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Block
- Roof: Dimensional Style
Condition
- New construction: No
- Year built: 1950
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Electricity Available, Natural Gas Available, Phone Available, Sewer Available, Water Available
Community & HOA
Community
- Subdivision: Downtown
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $114/sqft
- Tax assessed value: $79,500
- Annual tax amount: $795
- Date on market: 9/12/2025
Price history
| Date | Event | Price |
|---|---|---|
| 1/29/2026 | Sold | $188,000-0.5%$114/sqft |
Source:  Imagine MLS #25501148 Report a problem | ||
| 1/2/2026 | Pending sale | $188,900$114/sqft |
Source: Imagine MLS #25501148 Report a problem | ||
| 12/12/2025 | Price change | $188,900-0.5%$114/sqft |
Source: Imagine MLS #25501148 Report a problem | ||
| 11/2/2025 | Price change | $189,900-5%$115/sqft |
Source: Imagine MLS #25501148 Report a problem | ||
| 9/12/2025 | Listed for sale | $199,900+399.8%$121/sqft |
Source: Imagine MLS #25501148 Report a problem | ||
| 9/13/2024 | Listing removed | $1,400$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 8/14/2024 | Listed for rent | $1,400$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 8/3/2018 | Sold | $40,000$24/sqft |
Source: Imagine MLS #1813441 Report a problem | ||
| 6/29/2018 | Pending sale | $40,000$24/sqft |
Source: Freedom Realty & Property Mgt #1813441 Report a problem | ||
| 6/26/2018 | Listed for sale | $40,000$24/sqft |
Source: Freedom Realty & Property Mgt #1813441 Report a problem | ||
| 6/19/2018 | Pending sale | $40,000$24/sqft |
Source: Freedom Realty & Property Mgt #1813441 Report a problem | ||
| 6/17/2018 | Listed for sale | $40,000$24/sqft |
Source: Freedom Realty & Property Mgt #1813441 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $795 +1.5% | $79,500 |
| 2023 | $783 | $79,500 |
| 2022 | $783 +0.3% | $79,500 |
| 2021 | $781 -0.2% | $79,500 |
| 2020 | $782 +574.1% | $79,500 |
| 2019 | $116 | $79,500 |
| 2018 | $116 | -- |
| 2017 | -- | -- |
| 2016 | -- | -- |
| 2015 | -- | -- |
| 2011 | -- | $119,100 |
| 2010 | -- | $119,100 |
Find assessor info on the county website
Neighborhood: 40391
Nearby homes
- $177,3003 bd1 ba912 sqft29 Ashland Ave, Winchester, KY 40391Off Market
- $141,8002 bd1 ba952 sqft25 Ashland Ave, Winchester, KY 40391Off Market
- $152,3002 bd1 ba1k sqft23 Ashland Ave, Winchester, KY 40391Off Market
- $108,6002 bd1 ba1.1k sqft33 Ashland Ave, Winchester, KY 40391Off Market
- $139,0002 bd1 ba904 sqft37 Ashland Ave, Winchester, KY 40391Sold
- $162,6002 bd1 ba1k sqft21 Ashland Ave, Winchester, KY 40391Off Market
- $268,6003 bd2 ba2.1k sqft415 E Broadway St, Winchester, KY 40391Off Market
- $151,0002 bd1 ba1.2k sqft410 E Washington St, Winchester, KY 40391Off Market
Nearby schools
GreatSchools rating
- 5/10Shearer Elementary SchoolGrades: K-4Distance: 0.3 mi
- 5/10Robert D Campbell Junior High SchoolGrades: 7-8Distance: 1.7 mi
- 5/10George Rogers Clark High SchoolGrades: 9-12Distance: 3.4 mi
Schools provided by the listing agent
- Elementary: Shearer
- Middle: Robert Campbell
- High: GRC
Source: Imagine MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Kentucky
- Clark County
- Winchester
- 40391
- 27 Ashland Ave
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