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$862,000
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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. 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.
Full Property Details
Full Property Details for 299 W 4th Ave
General
- Sold For: $862,000
- Taxes: $10,545 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6357207
- Added to Site: 69 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 7
- Interior Features: Ceiling Fan(s), Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Family Room, Wood Burning
- Appliances: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Washer
- Furnishings: Unfurnished
- Flooring: Laminate, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room, Upper Level
Exterior
- Exterior Features: French Doors, Private Mailbox
- Deck/Patio: Covered, Front Porch, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Front Porch, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: WINDERMERE TOWN
- Driving Directions: From Main Street go West on 3rd, left on Butler. House on the NE corner of 4th and Butler.
- Direction Faces: South
School Information
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
- Community Features: Golf Carts OK, Park, Playground, Restaurant, Tennis Court(s)
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: BB/HS Internet Available, Electricity Connected
Structural Information
- Architectural Info: Craftsman
- Architectural Style: Craftsman
- Exterior Const.: Wood Siding
- Basement Desc.: Crawl Space
- Roof: Shingle
- Windows: Insulated Windows
- Stories/Levels: Two
- Square Feet: 2,410
- Sq. Ft. Source: Public Records
- Living Area: 2,410 Sq. Ft.
- Year Built: 1984
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.38
- Lot Size (Sq. Ft.): 16,750
- Lot Size: 16750
- Frontage: Street Unpaved
- Street/Road Desc.: Unimproved, Dirt
Water Features
- Water Access: Yes
- Water Access Desc: Lake - Chain of Lakes
Green Features
- Energy Efficient: Windows
Financial Considerations
- Tax Amount: $10,545
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: PLAT OF WINDERMERE G/36 LOT 320 IN SEC 8-23-28 SW1/4
- Flood Zone Info: X
- APN: 172328933603200
- Property ID: 172328933603200
- Block/Lot/Section: 3
Listed by Upside Real Estate Inc
Sold by Upside Real Estate Inc
Get Pre-Approved Today
Schools
Schools serving 299 W 4th Ave
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 0.9 mi |
Gotha Middle School 9155 Gotha Road, Windermere, FL 34786 | 6-8 | 2.5 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 1.9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 299 W 4th Ave
Date
Details
Price
Change
Source
1/08/2026
Sold
$862,000
-3.69%
MLS
11/07/2025
Listed
$895,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
299 W 4th Avenue, Windermere, FL 34786 (MLS# O6357207) is a Single Family property that was sold at $862,000 on January 08, 2026. Want to learn more about 299 W 4th Avenue? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

