Map location of 1209 MAIN STREET, WINDERMERE, FL 34786
$945,000
Unlock Price Rating!

1209 Main Street, Windermere, FL 34786

 Contact
3 Beds
2 Baths
2,095 Sq Ft

Freshly remodeled and full of charm, this one-story home lives light, bright, and effortlessly easy. White oak floors flow from room to room like a warm welcome, setting the stage for airy spaces and sun-drenched corners.At the heart of the home, the family room opens wide with vaulted ceilings, a cozy fireplace, and windows that pull the outdoors in. The kitchen feels like the place everyone wants to gather, with a wraparound breakfast bar, quartz countertops, a wine fridge, and a cheerful breakfast nook that soaks in the morning light. Just beyond, a spacious dining room offers the ideal spot for long dinners, holiday celebrations, or spreading out homework and craft projects. A bonus room with plantation shutters adds an extra dash of flexibility office, playroom, studio, you choose.The magic continues outside. French doors from the primary suite open straight to the pool, giving the whole space a resort-like feel. The oversized, solar-heated pool sits amid a lush, fenced backyard. A covered lanai waits for afternoon lounging, weekend barbecues, or quiet mornings with coffee and birdsong.Practical touches shine just as brightly, including an abundance of windows, a sunny laundry room near the primary suite, a functional open layout, and a 2-car garage offering storage and everyday convenience.Walk 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. Move-in ready and filled with character, this home delivers a blend of comfort, beauty, and easy Florida living.

Listing By: Judy Black - UPSIDE REAL ESTATE INC flmfr Realty.com
  • MLS# O6363588
  • Date Listed11/28/2025
  • Days on Realty 1 Day
  • Bedrooms 3
  • Bathrooms 2 Full baths
  • Lot Size 0.35 acres (15,298 sq. ft)
  • Sewer Septic Tank
  • Subdivision WINDERMERE
  • Property Type Single Family
  • County Orange
  • Year Built 1979
  • Water Private, Well
  • Square Feet 2,095 sq. ft
  • Price Per Sq. Ft $451.07

Interior Features

  • Appliances Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Wine Refrigerator
  • Flooring Carpet, Tile, Wood
  • Cooling Central Air
  • Heating Central

Exterior / Lot Features

  • Roof Shingle
  • Lot Size Acres 0.35
  • Lot Size SQFT 15,298.00
  • Lot Features Paved

Directions

South on Main past Chase Rd.

Financial Considerations

  • Tax Amount $9,964
  • Terms Cash, Conventional, FHA, VA Loan

Nearby Schools

Source: School Digger

Thornebrooke Elementary School

Public • PK - 5 • Serves this home

4.34 mi

Distance

Westpointe Elementary

Public • PK - 5

4.93 mi

Distance

Lake Whitney Elementary School

Public • PK - 5

5.02 mi

Distance

Westbrooke Elementary School

Public • PK - 5

5.4 mi

Distance

Keenes Crossing Elementary School

Public • PK - 5

6.06 mi

Distance

William Frangus Elementary

Public • PK - 5

6.46 mi

Distance

Ucp West Orange Charter

Public • PK - 5

6.75 mi

Distance

Oak Hill Elementary School

Public • PK - 5

6.99 mi

Distance

Millennia Elementary School

Public • PK - 5

7.16 mi

Distance

Whispering Oak Elementary School

Public • PK - 5

7.32 mi

Distance

Chain Of Lakes Middle School

Public • 6 - 8

2.77 mi

Distance

Southwest Middle School

Public • 6 - 8

4 mi

Distance

Gotha Middle School

Public • 6 - 8 • Serves this home

4.73 mi

Distance

Horizon West Middle School

Public • 6 - 8

5.02 mi

Distance

Florida Virtual School Flex 6-8

Public • 6 - 8

6.34 mi

Distance

Bridgewater Middle School

Public • 6 - 8

6.97 mi

Distance

Florida Virtual Middle School

Public • 6 - 8

7.64 mi

Distance

Sunridge Middle

Public • 6 - 8

8.07 mi

Distance

Olympia High School

Public • 9 - 12 • Serves this home

2.3 mi

Distance

Windermere High School

Public • 9 - 12

4.34 mi

Distance

Dr. Phillips High School

Public • 9 - 12

4.81 mi

Distance

Universal Education Center

Public • 10 - 12

5.43 mi

Distance

Esteem Academy

Public • 9 - 12

5.91 mi

Distance

West Orange High School

Public • 9 - 12

6.34 mi

Distance

Florida Virtual School Flex 9-12

Public • 9 - 12

6.34 mi

Distance

Sunshine High Charter

Public • 9 - 12

7.59 mi

Distance

Florida Virtual High School

Public • 9 - 12

7.64 mi

Distance

Vanguard Preparatory Academy

Private • 01 - 12

1.9 mi

Distance

New World Dream Academy

Private • PK - 12

2.86 mi

Distance

Windermere Preparatory School

Private • PK - 12

3.48 mi

Distance

The Crenshaw School

Private • KG - 12

4.45 mi

Distance

House Of Academia Dba Academia Private Schl

Private • KG - 10

4.46 mi

Distance

Edgewood Children's Ranch

Private • UG - UG

4.93 mi

Distance

Flex Major School

Private • 06 - 12

5.61 mi

Distance

American School Of Leadership

Private • 09 - 12

5.82 mi

Distance

Light Christian Academy - South Campus

Private • 06 - 12

6.42 mi

Distance

Winners Primary School

Private • KG - 11

6.42 mi

Distance

Sales & Tax History

Source: Public Records

Population & Environment

Source: Sperling's Best Places

Walkability in FL / 34786

Source: Walkscore

22/100

Car-Dependent

Walk Score ®

32/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 14/100, Transit Score: 0/100, Bike Score: 34/100.

Points of Interest near 1209 MAIN STREET, WINDERMERE, FL 34786

Frequently Asked Questions for 1209 MAIN STREET

Source: Realty.com

1209 MAIN STREET, WINDERMERE, FL 34786 is a Single Family 2,095 sq. ft. home listed for sale. Realty.com has 44 photos available of this 3 bed, 2 bath house, listed at $945,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Realty.com has 44 photos of 1209 MAIN STREET.

Our records indicate that 1209 MAIN STREET was built in 1979.

The full address for this home is 1209 MAIN STREET, WINDERMERE, FL 34786.

1209 MAIN STREET has been listed on Realty.com since Fri November 28, 2025

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 14/100, Transit Score: 0/100, Bike Score: 34/100.

There are 3 schools assigned to this home. Check out the schools near 1209 MAIN STREET. Thornebrooke Elementary School (Grades: PK - 5), Gotha Middle School (Grades: 6 - 8), Olympia High School (Grades: 9 - 12)

Listing provided courtesy of: Upside Real Estate Inc (tel: 407-308-5750)
Listing agent: Judy Black (#261001354)

This content last refreshed on 2025-11-29 18:45:01. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 1209 MAIN STREET, WINDERMERE, FL 34786 : MLS# O6363588

Message
Tour
Chat