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.
Sold for $862,000
$862,000
299 W 4TH AVENUE, WINDERMERE, FL 34786
4beds
2,410sqft
Single Family Residence
Built in 1984
0.38 Acres Lot
$865,400 Zestimate®
$358/sqft
$4,503 Estimated rent
Home value
$865,400
$788,000 - $943,000
$4,503/mo
Zestimate® history
Owner options
List your home for rent
$4,503/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$4,503/mo
Rent Zestimate®
Refinance and save
$6,206/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$6,206/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Island kitchenSecond-floor laundry roomGranite countertopsBeautiful curb appealNewly installed windowsSpacious primary suiteCharming wood-burning fireplace
Zillow last checked:
Listing updated:
Listed by:
Judy Black 407-810-1803,
UPSIDE REAL ESTATE INC 407-308-5750,
Amanda Black PA 407-616-0140,
UPSIDE REAL ESTATE INC
Bought with:
Amanda Black PA, 3209990
UPSIDE REAL ESTATE INC
Source: Stellar MLS,MLS#: O6357207
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Utility Room
Primary bedroom
- Features: Walk-In Closet(s)
- Level: Second
- Area: 400 Square Feet
- Dimensions: 20x20
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 132 Square Feet
- Dimensions: 12x11
Bedroom 3
- Features: Walk-In Closet(s)
- Level: Second
- Area: 154 Square Feet
- Dimensions: 14x11
Bedroom 4
- Features: Built-in Closet
- Level: Second
- Area: 154 Square Feet
- Dimensions: 14x11
Balcony porch lanai
- Level: First
- Area: 560 Square Feet
- Dimensions: 40x14
Kitchen
- Level: First
- Area: 216 Square Feet
- Dimensions: 12x18
Living room
- Level: First
- Area: 520 Square Feet
- Dimensions: 26x20
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Washer
- Laundry: Inside, Laundry Room, Upper Level
Features
- Ceiling Fan(s), Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s)
- Flooring: Laminate, Hardwood
- Doors: French Doors
- Windows: Insulated Windows
- Basement: Crawl Space
- Has fireplace: Yes
- Fireplace features: Family Room, Wood Burning
Interior area
- Total structure area: 3,936
- Total interior livable area: 2,410 sqft
Property
Parking
- Total spaces: 3
- Parking features: Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
- Attached garage spaces: 3
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 34x24
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Front Porch, Rear Porch, Screened
- Exterior features: Private Mailbox
- Has view: Yes
- View description: Trees/Woods
- Waterfront features: Lake Privileges
Lot
- Size: 0.38 Acres
- Features: Corner Lot, City Lot, Near Golf Course
- Residential vegetation: Bamboo, Fruit Trees, Oak Trees
Details
- Parcel number: 172328933603200
- Zoning: SFR
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Craftsman
- Property subtype: Single Family Residence
Materials
- Wood Siding
- Foundation: Crawlspace
- Roof: Shingle
Condition
- New construction: No
- Year built: 1984
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: BB/HS Internet Available, Electricity Connected
Green energy
- Energy efficient items: Windows
Community & HOA
Community
- Features: Golf Carts OK, Park, Playground, Restaurant, Tennis Court(s)
- Pet fee: $0 monthly
- Subdivision: WINDERMERE TOWN
HOA
- Has HOA: No
Location
- Region: Windermere
Financial & listing details
- Price per square foot: $358/sqft
- Tax assessed value: $643,003
- Annual tax amount: $10,545
- Date on market: 11/7/2025
- Cumulative days on market: 35 days
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Unimproved, Dirt
Price history
| Date | Event | Price |
|---|---|---|
| 1/8/2026 | Sold | $862,000-3.7%$358/sqft |
Source:  Stellar MLS #O6357207 Report a problem | ||
| 12/13/2025 | Pending sale | $895,000$371/sqft |
Source: Stellar MLS #O6357207 Report a problem | ||
| 11/7/2025 | Listed for sale | $895,000+37.7%$371/sqft |
Source: Stellar MLS #O6357207 Report a problem | ||
| 1/2/2025 | Sold | $650,000+52.9%$270/sqft |
Source: Agent Provided Report a problem | ||
| 4/22/2019 | Sold | $425,000-5.6%$176/sqft |
Source: Public Record Report a problem | ||
| 2/12/2019 | Price change | $450,000-5.3%$187/sqft |
Source: EXP REALTY LLC #O5747950 Report a problem | ||
| 2/1/2019 | Price change | $475,000-5%$197/sqft |
Source: EXP REALTY LLC #O5747950 Report a problem | ||
| 12/30/2018 | Price change | $499,999-4.8%$207/sqft |
Source: EXP REALTY LLC #O5747950 Report a problem | ||
| 12/13/2018 | Price change | $525,000-4.5%$218/sqft |
Source: EXP REALTY LLC #O5747950 Report a problem | ||
| 11/20/2018 | Listed for sale | $549,900+134%$228/sqft |
Source: EXP REALTY LLC #O5747950 Report a problem | ||
| 2/13/1997 | Sold | $235,000$98/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $10,546 +7% | $588,033 +10% |
| 2023 | $9,853 +16.5% | $534,575 +10% |
| 2022 | $8,458 +7.2% | $485,977 +9.7% |
| 2021 | $7,891 +3.3% | $442,982 +4.3% |
| 2020 | $7,639 -1.8% | $424,592 -0.4% |
| 2019 | $7,779 +5.7% | $426,201 +7.4% |
| 2018 | $7,358 +0% | $396,836 +1.1% |
| 2017 | $7,358 +3% | $392,562 +8.2% |
| 2016 | $7,142 +6.1% | $362,732 +7.9% |
| 2015 | $6,731 +32.3% | $336,265 +25.7% |
| 2014 | $5,086 +10.5% | $267,515 +11.5% |
| 2013 | $4,605 -3.8% | $239,880 -3.4% |
| 2012 | $4,789 -5.5% | $248,296 -5.2% |
| 2011 | $5,068 -3.2% | $262,010 -9% |
| 2010 | $5,236 | $287,940 -14.9% |
| 2009 | -- | $338,275 -14% |
| 2008 | $6,316 -11.8% | $393,178 -12.3% |
| 2007 | $7,162 +9.4% | $448,162 +21.3% |
| 2006 | $6,545 +22.8% | $369,539 +26.9% |
| 2005 | $5,329 +3.6% | $291,120 -3.6% |
| 2004 | $5,144 +19.5% | $301,960 +22% |
| 2003 | $4,303 +11.4% | $247,527 +7% |
| 2002 | $3,864 +1.1% | $231,333 +4.5% |
| 2001 | $3,820 +2.4% | $221,366 +3.1% |
| 2000 | $3,731 | $214,666 |
Find assessor info on the county website
Neighborhood: 34786
Nearby homes
- $969,0004 bd3 ba2.9k sqft325 Butler St, Windermere, FL 34786Off Market
- $934,0003 bd2 ba2.7k sqft405 Butler St, Windermere, FL 34786Off Market
- $1,028,0004 bd3 ba2.4k sqft336 Forest St, Windermere, FL 34786Off Market
- $831,9003 bd2 ba2.8k sqft328 Forest St, Windermere, FL 34786Off Market
- $889,2004 bd3 ba2.2k sqft315 Butler St, Windermere, FL 34786Off Market
- $1,015,0004 bd3 ba3.1k sqft307 W 4th Ave, Windermere, FL 34786Sold
- $963,1004 bd3 ba2.9k sqft406 Forest St, Windermere, FL 34786Off Market
- $844,0003 bd3 ba2k sqft326 Butler St, Windermere, FL 34786Off Market
Nearby schools
GreatSchools rating
- 10/10Windermere Elementary SchoolGrades: PK-5Distance: 0.9 mi
- 6/10Gotha Middle SchoolGrades: 6-8Distance: 2.8 mi
- 5/10Olympia High SchoolGrades: 9-12Distance: 1.9 mi
Schools provided by the listing agent
- Elementary: Windermere Elem
- Middle: Gotha Middle
- High: Olympia High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$865,400
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$865,400
- Florida
- Orange County
- Windermere
- 34786
- 299 W 4TH AVENUE
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Windermere Topics
