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299 W 4th Avenue, 
Windermere, FL 34786

$895,000


4

Beds


3

Baths


2,410

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Judy Black

Amanda Black

Upside Real Estate Inc

Last updated:

November 11, 2025, 08:06 PM

MLS#

O6357207

Source:

MFRMLS

About This Home

299 W 4th Avenue

This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting. Step inside to original wood floors that extend throughout the main living areas, enriching the home with warmth and timeless appeal. The family room centers around a charming wood-burning fireplace, surrounded by newly installed windows (2020) that fill the space with natural light. French doors open to a large screened porch — an ideal spot for morning coffee, outdoor dining, or unwinding beneath the shade of mature trees. The island kitchen features granite countertops and generous workspace for cooking and entertaining. The first floor includes a full bedroom and bath, perfect for guests or a home office. Upstairs, the spacious primary suite offers a peaceful retreat, joined by two additional bedrooms and the convenience of a second-floor laundry room. New Septic and drain field 2020, A/C 2024, Well re-sleaved and new pump 2024. A partially air-conditioned, three-car garage provides excellent storage and space for vehicles, golf carts, or weekend adventure gear. Stroll or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience.

Home Facts

Single Family

3 Baths

4 Bedrooms

Built in 1984

Price Summary

895,000

$371 per Sq. Ft.

MLS #:

O6357207

Last Updated:

November 11, 2025, 08:06 PM

Added:

7 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

3

Interior

Living Area:

2,410 Sq. Ft.


Structure

Structure

Architectural Style:

Craftsman

Building Area:

3,936 Sq. Ft.

Year Built:

1984


Lot

Lot Size (Sq. Ft):

16,750


Finances & Disclosures

Finances

Price:

$895,000

Price per Sq. Ft:

$371 per Sq. Ft.

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The information being provided by Stellar Mls is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Stellar Mls. Upside Real Estate Inc is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Upside Real Estate Inc, a broker participant of Stellar Mls. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Stellar Mls and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Properties in listings may have been sold or may no longer be available. Copyright 2025 Stellar Mls. All rights reserved.

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