2021 Winston Ave

Louisville, KY
$ 399,900 Beds 3 Baths 2 Sq 1,676
Monthly Estimate* How much can I afford?

Welcome to 2021 Winston Avenue, a charming 3-bedroom, 2-bath Cape Cod located in the heart of the Highlands! Surrounded by beautiful homes and ideally located in one of Louisville's most beloved neighborhoods, this inviting home blends classic character with thoughtful updates and a wonderfully livable floor plan. Inside you'll find a warm and welcoming living room featuring a fireplace, built-in cabinetry, beautiful hardwood floors, and an abundance of natural light. Hardwood floors flow throughout the entire first floor, adding warmth and timeless character to the home. The spacious dining room flows effortlessly into the family room, where built-in bookcases and plentiful windows create a comfortable gathering space. The adjacent informal dining area and thoughtfully designed kitchen make everyday living and entertaining feel effortless, with the kitchen opening directly to the family room with a high ceiling. Two bedrooms are conveniently located on the first floor, including one with a large walk-in closet. A nicely renovated hall bathroom features beautiful marble tile and a low-threshold shower, adding a fresh, stylish touch. Upstairs, discover a spacious open bedroom retreat with new paint and new carpet, generous closet space, including a cedar-lined closet, and a full bathroom. This private and versatile space is perfect for a primary suite, guest retreat, home office, or whatever best suits your lifestyle. The large unfinished basement offers exciting potential for future expansion, recreation, storage, or additional living space. Outside, enjoy a deck overlooking the partially fenced yard, perfect for relaxing, entertaining, or enjoying a quiet evening. A convenient one-car garage provides additional parking and storage. Recent updates include a newer roof and gutters, along with the freshly painted and newly carpeted upstairs, providing added appeal and peace of mind. With its inviting spaces, classic Cape Cod charm, hardwood floors throughout the first floor, built-ins, flexible living areas, and fantastic Highlands location, 2021 Winston Avenue is a home you'll be excited to make your own. Come see all the character and possibilities this special property has to offer!

Active

  • Price
  • $ 399,900
  • City
  • Louisville
  • Bedrooms
  • 3
  • Full Bathrooms
  • 2
  • County
  • Jefferson
  • Half Bathrooms
  • 0
  • Area
  • Butchertwn-Hghlnds-Germantwn
  • Lot Size
  • 0.17 Acres
  • Zip
  • 40205
  • Sqr Footage
  • 1,676
  • Year Built
  • 1941
  • Style
  • Cape Cod
  • MLS#
  • 1727842
Listed By: Rainey Allen Shaw East
Data Source: Metro Search, Inc.

Features

General

Heating Forced Air,Natural Gas
Cooling Central Air
Utilities Electricity Connected,Fuel:Natural
Roof Shingle
Garage Spaces 1
Architectural Style Cape Cod
Construction Materials Vinyl Siding,Brick
Year Built 1941
Stories Count 2
Property Subtype Single Family Residence
County Jefferson
Property Type Residential
HOA false
Attached Garage false
Subdivision Name WINSTON FOREST
Garage Y/N true
Other Structures Garage(s)
Total Rooms 11
Full Baths 2
Status Active
Directions Bardstown Road to Winston Avenue OR Newburg Road to Dundee Road to Lakeside Drive to Winston Avenue
City Louisville
MLS Area 02-Butchertwn/Hghlnds/Germantwn
Lot Size Units Acres
Lot Size Square Feet 7183
MLS Area Minor 02-Butchertwn/Hghlnds/Germantwn
Standard Status Active
Tax Lot 0119

Interior Features

Basement Unfinished
Total Fireplaces 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Above Grade Finished Area 1568
Total Bedrooms 3
LivingAreaSource Other
Total Baths 2

Exterior Features

Fencing Partial
Parking Features Detached
Lot Features Level
Water Source Public
Lot Size Area 0.17
Foundation Details Poured Concrete
Building Area Total 1568
Lot Size Acres 0.17

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Shelbyville, KY office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School
Middle School
High School Unknown High School

Price History

9/1/2026 Listed $399,900

Property vs Zip Code Average in 40205

Price
AVG $580K
$400K
Year Built
AVG 1943
1941

2021 Winston Ave Louisville, KY is a Single Family Home for sale at $399900 with 1676 sqft and a lot size of 0.17 Acres Acre(s). 2021 Winston Ave Louisville has 3 bedrooms, 2 baths and was built in 1941. The property's zip code is 40205 which is in Louisville, KY

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.