Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1 bedroom, 1 bathroom Unit A-3: Office/studio-style apartment with 1 bedroom and 1 bathroom The duplex (Building B) offers two additional units: Unit B-1: 2 bedrooms, 1 bathroom Unit B-2: 2 bedrooms, 1 bathroom With five total units, this property provides strong income potential and flexibility for a variety of investment strategies. A recent appraisal came in at $320,000, and the property is priced below appraised value, creating built-in equity from day one.Great opportunity for investors seeking a solid multifamily asset with upside. Call today to schedule your private showing.
Sold for $260,000
$260,000
144 Holly Ave, Winchester, KY 40391
8beds
3,637sqft
Duplex
Built in 2001
-- sqft lot
$292,800 Zestimate®
$71/sqft
$1,220 Estimated rent
Home value
$292,800
$278,000 - $307,000
$1,220/mo
Zestimate® history
Owner options
List your home for rent
$1,220/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$1,220/mo
Rent Zestimate®
Refinance and save
$1,588/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$1,588/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Listed by:
Shane T Underwood 859-699-2969,
Keller Williams Commonwealth
Bought with:
Susie C Rodes, 196231
Berkshire Hathaway de Movellan Properties
Source: Imagine MLS,MLS#: 26002633
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 8
- Bathrooms: 5
- Full bathrooms: 5
Heating
- Baseboard, Electric, Forced Air, Heat Pump, Natural Gas, Other
Cooling
- Central Air, Ceiling Fan(s), Electric, Heat Pump, Window Unit(s), Wall Unit(s)
Interior area
- Total structure area: 3,637
- Total interior livable area: 3,637 sqft
Property
Parking
- Total spaces: 5
- Parking features: On Site
Lot
- Size: 9,583 Square Feet
Details
- Parcel number: 053400500200
- Zoning description: I -1
Construction
Type & style
- Home type: MultiFamily
- Property subtype: Duplex
- Attached to another structure: Yes
Materials
- Roof: Shingle
Condition
- New construction: No
- Year built: 2001
Utilities & green energy
- Utilities for property: Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Community & HOA
Community
- Subdivision: North Park
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $71/sqft
- Tax assessed value: $77,000
- Annual tax amount: $770
- Date on market: 2/14/2026
Price history
| Date | Event | Price |
|---|---|---|
| 6/9/2026 | Sold | $260,000-15.7%$71/sqft |
Source:  Imagine MLS #26002633 Report a problem | ||
| 5/28/2026 | Pending sale | $308,500$85/sqft |
Source: Imagine MLS #26002633 Report a problem | ||
| 4/24/2026 | Contingent | $308,500$85/sqft |
Source: Imagine MLS #26002633 Report a problem | ||
| 4/20/2026 | Price change | $308,500-3.4%$85/sqft |
Source: Imagine MLS #26002633 Report a problem | ||
| 2/14/2026 | Listed for sale | $319,500$88/sqft |
Source: Imagine MLS #26002633 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $770 +1.5% | $77,000 |
| 2023 | $758 | $77,000 |
| 2022 | $758 +0.3% | $77,000 |
| 2021 | $756 -0.2% | $77,000 |
| 2020 | $758 +574.1% | $77,000 |
| 2019 | $112 | $77,000 |
| 2018 | $112 | $77,000 |
| 2017 | $112 | $77,000 |
| 2016 | $112 | $77,000 |
| 2015 | $112 | $77,000 |
| 2013 | $112 | $77,000 +40% |
| 2011 | -- | $55,000 -28.6% |
| 2010 | -- | $77,000 |
Find assessor info on the county website
Neighborhood: 40391
Nearby homes
- $125,5002 bd1 ba1k sqft204 Holly Ave, Winchester, KY 40391Off Market
- $180,8003 bd1 ba963 sqft138 Holly Ave, Winchester, KY 40391Off Market
- $123,1003 bd1 ba1.2k sqft201 Holly Ave, Winchester, KY 40391Off Market
- $131,6003 bd1 ba1.2k sqft134 Holly Ave, Winchester, KY 40391Off Market
- $35,0003 bd1 ba826 sqft203 Holly Ave, Winchester, KY 40391Off Market
- $118,5003 bd1 ba1k sqft205 Holly Ave, Winchester, KY 40391Off Market
- $190,0003 bd2 ba1.2k sqft141 Holly Ave, Winchester, KY 40391Sold
- $12,5003 bd1 ba1.4k sqft132 Holly Ave, Winchester, KY 40391Off Market
Nearby schools
GreatSchools rating
- 4/10Conkwright Elementary SchoolGrades: K-4Distance: 0.6 mi
- 5/10Robert D Campbell Junior High SchoolGrades: 7-8Distance: 1.8 mi
- 5/10George Rogers Clark High SchoolGrades: 9-12Distance: 3.5 mi
Schools provided by the listing agent
- Elementary: Conkwright
- 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.
Get pre-qualified for a loan
At Zillow Home Loans, we can pre-qualify you in as little as 5 minutes with no impact to your credit score.An equal housing lender. NMLS #10287.
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$292,800
2% more
+$5,856
With Zillow Showcase(estimated)
$298,656
- Kentucky
- Clark County
- Winchester
- 40391
- 144 Holly Ave
Nearby cities
Nearby zip codes
Other Winchester Topics
