299 W 4TH AVENUE, Windermere, FL, 34786 | $895,000

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

  • Rooms: 7
  • Bedrooms: 4
  • Baths: 3 full
  • Laundry: Inside, Laundry Room, Upper Level
  • Style: Craftsman
  • Year Built: 1984
  • Garage: 3-car Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
  • Heating: Central, Electric
  • Cooling: Central Air
  • Approx Sq. Feet: 2,410
  • Acreage: 0.38
  • Est. Taxes: $10,545
  • Lot Desc: Corner Lot, City Lot, Near Golf Course
  • View: Trees/Woods
  • Elem. School: Windermere Elem
  • Middle School: Gotha Middle
  • High School: Olympia High
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Washer
  • MLS#: O6357207
  • Days on Market: 18 days
  • Website: https://www.raveis.com
    /prop/O6357207/299w4thavenue_windermere_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 12/11/2025 1:32:09 PM)
Listing courtesy of UPSIDE REAL ESTATE INC   Phone: 407-308-5750

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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Our Insurance Division:

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299 W 4TH AVENUE, Windermere, FL, 34786

$895,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $716,000 $716,000 $716,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.625% 6.000% 5.875%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.440% 6.121% 6.038%
Monthly Tax Payment $879 $879 $879
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $4,122 $4,293 $5,994
Total Monthly Payment $5,093 $5,264 $6,965

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.