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Property view

2021 Winston Ave, 
Louisville, KY 40205

$399,900


3

Beds


2

Baths


1,676

Sq Ft


Single Family

Coming Soon

Listed by

Chris S Allen

Audrey Allen

Rainey Allen Shaw East

+1 502-641-4342

Last updated:

September 1, 2026, 03:51 AM

MLS#

1727842

Source:

KY MSMLS

Source MLS Verified

About This Home

2021 Winston Ave

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!

Home Facts

Single Family

2 Baths

3 Bedrooms

Built in 1941

Subdivision & Development:

WINSTON FOREST

Price Summary

399,900

$238 per Sq. Ft.

MLS #:

1727842

Last Updated:

September 1, 2026, 03:51 AM


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,676 Sq. Ft.


Structure

Structure

Architectural Style:

Cape Cod

Building Area:

1,568 Sq. Ft.

Year Built:

1941


Lot

Lot Size (Sq. Ft):

7,183


Finances & Disclosures

Finances

Price:

$399,900

Price per Sq. Ft:

$238 per Sq. Ft.

Source:KY MSMLS
The information being provided by Greater Louisville Association Of REALTORS® is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Greater Louisville Association Of REALTORS® All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.