299 W 4th Avenue, WINDERMERE, FL

$895,000

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4

Beds

3

Baths

2,410

Square feet

0.38

Acres

About 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.

Features of 299 W 4th Avenue

MLS® # O6357207
Price $895,000
Bedrooms 4
Bathrooms 3.00
Full Baths 3
Square Footage 2,410
Acres 0.38
Year Built 1984
Type Residential
Sub-Type Single Family Residence
Style Craftsman
Status Pending

Community Information

Address 299 W 4th Avenue
Area Windermere
Subdivision WINDERMERE TOWN
City WINDERMERE
County Orange
State FL
Zip Code 34786-8503

Amenities

Parking Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
# of Garages 3
View Trees/Woods
Is Waterfront No
Has Pool No

Interior

Interior Features Ceiling Fan(s), Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
Appliances Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Washer
Heating Central, Electric
Cooling Central Air
Fireplace Yes
Fireplaces Family Room, Wood Burning
# of Stories 2

Exterior

Exterior Features French Doors, Private Mailbox
Lot Description Corner Lot, City Lot, Near Golf Course
Roof Shingle
Foundation Crawlspace

School Information

Elementary Windermere Elem
Middle Gotha Middle
High Olympia High

Additional Information

Date Listed November 7th, 2025
Days on Market 35
Zoning SFR
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeUPSIDE REAL ESTATE INC

Listing Map

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