299 W 4TH AVENUE, Windermere, FL 34786

• 4 beds |
• 3 baths |
• 2,410 sqft

Property Description

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. 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.

Listing Status:

Active

Date Added:

November 7, 2025 at 06:00AM

Listing Office:

UPSIDE REAL ESTATE INC : 407-308-5750

Listing Agent:

Judy Black : 407-810-1803

MLS ID:

O6357207

Interior

• General: Ceiling Fans(s)Solid Wood CabinetsStone CountersVaulted Ceiling(s)Walk-In Closet(s)
• Rooms: Inside Utility
• Appliances: CooktopDishwasherDisposalDryerElectric Water HeaterMicrowaveWasher
• Laundry: InsideLaundry RoomUpper Level
• Basement: Crawl Space
• Flooring: LaminateWood
• A/C: Central Air
• Heating: CentralElectric
• Fireplace: Family RoomWood BurningFireplace
• Eco/Green Feature: Windows

Exterior

• General: French DoorsPrivate Mailbox
• Style: Craftsman
• Other Structures: Front PorchRear PorchScreenedCovered
• Parking: DrivewayGarage Door OpenerGarage Faces SideGolf Cart Garage

Construction

• Roofing: Shingle
• Windows: Insulated Windows
• General: Wood SidingTwoCrawlspace

Location

• Road/Access: Dirt
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: SFRPLAT OF WINDERMERE G/36 LOT 320 IN SEC 8-23-28 SW1/417-23-28-9336-03-200
• View: Trees/Woods

Utilities

• Utilities: BB/HS Internet AvailableElectricity Connected
• Water: Well
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple

This listing courtesy of Judy Black, UPSIDE REAL ESTATE INC