2020 Winston Ave

Louisville, KY
$ 625,000 Beds 3 Baths 2 Sq 2,876
Monthly Estimate* How much can I afford?

Nestled in the heart of the highly sought-after Strathmoor Manor neighborhood, this classic Highlands Cape Cod perfectly blends timeless charm with modern comfort. Just minutes from the restaurants, coffee shops, and local boutiques lining Bardstown Road, this location also offers easy access to some of Louisville's most beloved parks, the Louisville Zoo, Bellarmine University, and is only a couple blocks from Atherton High School and Assumption High School. From the moment you step inside, this home absolutely oozes charm with gorgeous hardwood floors, detailed molding, beautiful windows, spacious rooms, and a cozy fireplace anchoring the living room. The main floor offers a wonderful flow with a large living room, dedicated dining room, and an updated eat-in kitchen featuring plenty of modern touches while still honoring the character of the home. Three bedrooms and two full bathrooms complete the first floor. Just beyond the living spaces, a screened-in porch overlooks what truly feels like a private garden oasis. The beautifully landscaped yard offers exceptional privacy and the perfect setting for relaxing mornings, entertaining friends, or simply enjoying nature. Upstairs, the fully renovated second floor is spectacular with soaring high ceilings and oversized windows that flood the space with natural light. Whether used as an incredible primary suite with walk-in closet, a second family room, art studio, or dual home offices, the possibilities are endless. This is the kind of home that rarely comes along — full of warmth, personality, and classic Highlands character in one of Louisville's most beloved neighborhoods.

Active

  • Price
  • $ 625,000
  • City
  • Louisville
  • Bedrooms
  • 3
  • Full Bathrooms
  • 2
  • County
  • Jefferson
  • Half Bathrooms
  • 0
  • Area
  • Butchertwn-Hghlnds-Germantwn
  • Lot Size
  • 0.26 Acres
  • Zip
  • 40205
  • Sqr Footage
  • 2,876
  • Year Built
  • 1941
  • Style
  • Cape Cod
  • MLS#
  • 1716997
Listed By: Keller Williams Collective
Data Source: Metro Search, Inc.

Features

General

Heating Natural Gas
Cooling Central Air
Utilities Electricity Connected
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 true
Subdivision Name WINSTON FOREST
Garage Y/N true
Total Rooms 13
Full Baths 2
Status Active
Directions I-264 to Bardstown Rd. Turn left onto Winston Ave.
City Louisville
MLS Area 02-Butchertwn/Hghlnds/Germantwn
Lot Size Units Acres
Lot Size Square Feet 11400
MLS Area Minor 02-Butchertwn/Hghlnds/Germantwn
Standard Status Active
Tax Lot 0172

Interior Features

Basement Unfinished
Total Fireplaces 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Above Grade Finished Area 2876
Total Bedrooms 3
LivingAreaSource Other
Total Baths 2

Exterior Features

Fencing Wood
Parking Features Attached,Driveway
Lot Size Area 0.26
Foundation Details Concrete Blk
Building Area Total 2876
Lot Dimensions 75X152
Lot Size Acres 0.26

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
Agent Photo

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

9/14/2026 Listed $625,000

Property vs Zip Code Average in 40205

Price
AVG $590K
$630K
Year Built
AVG 1944
1941

2020 Winston Ave Louisville, KY is a Single Family Home for sale at $625000 with 2876 sqft and a lot size of 0.26 Acres Acre(s). 2020 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.