299 W 4th Ave
Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,410 sqft (on 0.38 acres)
$862,000
Last Sold: Jan 8, 2026
4% below list $895K
$358/sqft
Est. Refi. Payment $5,855/mo*
$862,000
Last Sold: Jan 8, 2026
4% below list $895K
$358/sqft
Est. Refi. Payment $5,855/mo*
4 Beds
3 Baths
2,410 sqft
(on 0.38 acres)
Local Information
© Google
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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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from January 08, 2026
Home Highlights
Parking
3 Car Garage
Outdoor
Porch
View
Trees/Woods
HOA
None
Price/Sqft
$358/sqft
Listed
180+ days ago
Home Details for 299 W 4th Ave
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Interior Details Basement: Crawl SpaceNumber of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Balcony Porch Lanai, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 2410 Square Feet |
Appliances & Utilities Utilities: BB/HS Internet Available, Electricity ConnectedAppliances: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, WasherDishwasherDisposalDryerLaundry: Inside,Laundry Room,Upper LevelMicrowaveWasher |
Heating & Cooling Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa Fireplace: Family Room, Wood BurningHas a FireplaceNo Spa |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Window: Insulated WindowsDoor: French DoorsFlooring: Laminate, Hardwood |
Levels, Entrance, & Accessibility Stories: 2Number of Stories: 2Levels: TwoFloors: Laminate, Hardwood |
View Has a ViewView: Trees/Woods |
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Exterior Home Features Roof: ShinglePatio / Porch: Covered, Front Porch, Rear Porch, ScreenedVegetation: Bamboo, Fruit Trees, Oak TreesExterior: Private MailboxFoundation: CrawlspaceNo Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3Other Parking: Garage Dimensions: 34x24No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Garage Door Opener,Garage Faces Side,Golf Cart Garage |
Frontage Waterfront: Lake PrivilegesResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Unimproved, DirtNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Cumulative Days on Market: 35 |
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Year Built Year Built: 1984 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Craftsman |
Building Construction Materials: Wood SidingNot a New ConstructionNo Additional Parcels |
Property Information Parcel Number: 172328933603200 |
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Price List Price: $895,000Price Per Sqft: $358/sqft |
Status Change & Dates Off Market Date: Fri Dec 12 2025Possession Timing: Close Of Escrow |
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MLS Status: Sold |
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Direction & Address City: WINDERMERECommunity: WINDERMERE TOWN |
School Information Elementary School: Windermere ElemJr High / Middle School: Gotha MiddleHigh School: Olympia High |
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Building Area Building Area: 3936 Square Feet |
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Community Features: Golf Carts OK, Park, Playground, Restaurant, Tennis Court(s)Not Senior Community |
Other Playground |
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Association for this Listing: Orlando RegionalNo HOA |
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Lot Area: 0.38 acres |
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Special Conditions: None |
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Listing Terms: Cash, Conventional, VA Loan |
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Energy Efficiency Features: Windows |
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Business Information Ownership: Fee Simple |
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Mls Number: O6357207Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-172328933603200-R-N |
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Golf Carts OKParkPlaygroundRestaurantTennis Court(s) |
Last check for updates: about 14 hours ago
Listed by Judy Black, (407) 810-1803
UPSIDE REAL ESTATE INC, (407) 308-5750
Amanda Black PA, (407) 616-0140
UPSIDE REAL ESTATE INC, (407) 308-5750
Bought with: Amanda Black PA, (407) 616-0140, UPSIDE REAL ESTATE INC, (407) 308-5750
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6357207

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Price History for 299 W 4th Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 01/08/2026 | $862,000 | Sold | Stellar MLS #O6357207 |
| 12/13/2025 | $895,000 | Pending | Stellar MLS #O6357207 |
| 11/07/2025 | $895,000 | Listed For Sale | Stellar MLS #O6357207 |
| 01/02/2025 | $650,000 | Sold | N/A |
| 04/22/2019 | $425,000 | Sold | N/A |
| 02/12/2019 | $450,000 | PriceChange | Agent Provided |
| 02/01/2019 | $475,000 | PriceChange | Agent Provided |
| 12/30/2018 | $499,999 | PriceChange | Agent Provided |
| 12/13/2018 | $525,000 | PriceChange | Agent Provided |
| 11/20/2018 | $549,900 | Listed For Sale | Agent Provided |
| 02/13/1997 | $235,000 | Sold | N/A |
Market trends in Windermere
Last updated May 2026
Avg. sale price
$672K
$26.67KMoM
Sale-to-List Price
97.5%
0.3%MoM
Price per sq ft
$262
$6MoM
Available listings
291
2MoM
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $10,546 |
| Assessment | $643,003 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$4,110/mo
Comparable Sales for 299 W 4th Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.26 | Single-Family Home | $975,000 | 10/20/25 | 3 | 3 | 2,353 | |
0.34 | Single-Family Home | $1,050,000 | 05/21/26 | 4 | 3 | 2,412 | |
0.35 | Single-Family Home | $830,000 | 10/27/25 | 4 | 2 | 2,582 | |
0.42 | Single-Family Home | $910,000 | 05/09/26 | 3 | 2.5 | 2,475 | |
0.25 | Single-Family Home | $890,000 | 07/31/25 | 3 | 2 | 2,562 | |
0.39 | Single-Family Home | $1,050,000 | 10/31/25 | 4 | 2 | 2,191 | |
0.36 | Single-Family Home | $850,000 | 10/21/25 | 3 | 2 | 2,778 | |
0.27 | Single-Family Home | $820,000 | 03/06/26 | 2 | 1.5 | 2,115 | |
0.34 | Single-Family Home | $1,060,000 | 09/11/25 | 3 | 1.5 | 2,011 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 299 W 4th Ave.
What Locals Say about Windermere
At least 270 Trulia users voted on each feature.
93 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say car is needed
87 % Say parking is easy
81 % Say people would walk alone at night
80 % Say it's quiet
79 % Say there's holiday spirit
78 % Say kids play outside
75 % Say streets are well-lit
64 % Say yards are well-kept
60 % Say they plan to stay for at least 5 years
59 % Say it's walkable to grocery stores
56 % Say there's wildlife
55 % Say it's walkable to restaurants
54 % Say neighbors are friendly
40 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 299 W 4th Ave
Off Market Homes Near 299 W 4th Ave

299 W 4th Ave, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,410 sqft single-family home built in 1984. This property is not currently available for sale. 299 W 4th Ave was last sold on Jan 8, 2026 for $862,000 (4% lower than the asking price of $895,000). The current Trulia Estimate for 299 W 4th Ave is $867,900.