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
| Office | UPSIDE REAL ESTATE INC |
|---|

