Google street view image for 55 Main St, Windermere, FL 34786

Off market nov 1997 for $165K

$584,311

Est. refi paymentEst. refi $1,156/mo

•

1 ba

•

1,054

sq ft

55 Main St, Windermere, FL 34786

About this home

55 Main St is a 1,054 square foot house on a 0.41 acre lot with 2 bedrooms and 1 bathroom. - it last sold on November 13, 1997 for $165,000. Based on Redfin's Windermere data, we estimate the home's value is $584,311.

Single-familyProperty Type

1922Year Built

0.41 acresLot Size

$554Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$584,311

$419K since sold in November 1997$7,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 25.3% lower than the average sale price ($782K) of 6 comparable homes.

SOLD SEP 15, 2026
$825,000
A
3 beds2 baths1,935 sq ft
11155 Lake Butler Blvd, Windermere, FL 34786
SOLD SEP 22, 2026
$690,000
B
2 beds1.5 baths1,398 sq ft
811 Main St, Windermere, FL 34786
SOLD MAY 19, 2026
$710,000
C
2 beds1 bath1,424 sq ft
305 Oakdale St, Windermere, FL 34786
SOLD OCT 14, 2026
$850,000
D
3 beds3 baths2,048 sq ft
706 Oakdale St, Windermere, FL 34786
SOLD JUN 11, 2026
$770,000
E
3 beds2 baths1,664 sq ft
825 Oakdale St, Windermere, FL 34786
SOLD JUL 1, 2026
$849,000
F
3 beds2 baths2,272 sq ft
111 Main St, Windermere, FL 34786

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Earn from this home

Sell

$540,687

Est. take-home

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Refinance

Est. cash available

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Rent

$2,429/mo

Redfin rental estimate

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Market trends in 34786, FL

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

96.1%

+0.0% MoM

Median sale price

$765K

$120K MoM

Avg. days on market

57d

6 days MoM

Recently sold homes

172

20 MoM

New listings for sale

NEW 23 HRS AGO
$630,000
4 beds3.5 baths2,454 sq ft
8582 Powder Ridge Trl, Windermere, FL 34786
COMING SOON
$1,100,000
4 beds4 baths3,348 sq ft
14038 Bluebird Park Rd, Windermere, FL 34786
COMING SOON
$649,000
2 beds1 bath1,340 sq ft
211 W 6th Ave, Windermere, FL 34786
EARLY ACCESS
$799,900
4 beds3 baths3,038 sq ft
8325 Vivaro Isle Way, Windermere, FL 34786
$669,000
4 beds3.5 baths2,686 sq ft
8631 Greenbank Blvd, Windermere, FL 34786
OPEN TODAY, 1PM TO 3PM
$350,000
2 beds2.5 baths1,280 sq ft
8516 Danforth Dr, Windermere, FL 34786
OPEN TODAY, 12PM TO 3PM
$400,000
4 beds2.5 baths1,706 sq ft
14500 Bridgewater Crossings Blvd, Windermere, FL 34786
3D WALKTHROUGH
$1,160,000
4 beds2.5 baths3,018 sq ft
9601 Ambleside Dr, Windermere, FL 34786
OPEN TODAY, 1PM TO 3PM
$365,000
2 beds2.5 baths1,380 sq ft
8634 Danforth Dr, Windermere, FL 34786
$3,250,000
4 beds5.5 baths4,200 sq ft
12620 S Lake Sawyer Ln, Windermere, FL 34786
See all

Provided by Redfin

Sale history for 55 Main St

Year

Property tax

Land + Additions

Assessment*

2025

$8,661 (+5.7%)

$455,000 + $38,362

$493,362

2024

$8,191 (+5.4%)

$455,000 + $38,362

$493,362

2023

$7,770 (+15.6%)

$455,000 + $36,647

$491,647

2022

$6,719 (+9.6%)

$355,000 + $37,528

$392,528

2021

$6,133 (+8.9%)

$355,000 + $37,528

$392,528

2020

$5,631 (−5.7%)

$305,000 + $32,713

$337,713

2019

$5,969 (+8.0%)

$285,000 + $35,692

$320,692

2018

$5,527 (+2.0%)

$285,000 + $35,692

$320,692

2017

$5,420 (+5.9%)

$255,000 + $36,239

$291,239

2016

$5,118 (+0.6%)

$255,000 + $36,239

$291,239

2015

$5,086 (+13.3%)

2014

$4,488 (+0.9%)

2013

$4,446 (−0.7%)

2012

$4,476

Tax history for 55 Main St

Year

Property tax

Land + Additions

Assessment*

2025

$8,661 (+5.7%)

$455,000 + $38,362

$493,362

2024

$8,191 (+5.4%)

$455,000 + $38,362

$493,362

2023

$7,770 (+15.6%)

$455,000 + $36,647

$491,647

2022

$6,719 (+9.6%)

$355,000 + $37,528

$392,528

2021

$6,133 (+8.9%)

$355,000 + $37,528

$392,528

2020

$5,631 (−5.7%)

$305,000 + $32,713

$337,713

2019

$5,969 (+8.0%)

$285,000 + $35,692

$320,692

2018

$5,527 (+2.0%)

$285,000 + $35,692

$320,692

2017

$5,420 (+5.9%)

$255,000 + $36,239

$291,239

2016

$5,118 (+0.6%)

$255,000 + $36,239

$291,239

2015

$5,086 (+13.3%)

2014

$4,488 (+0.9%)

2013

$4,446 (−0.7%)

2012

$4,476

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Heating & Cooling
Air Conditioning Type: Central
Heating Type: Forced Air

Exterior

Exterior Information
Building Construction Quality: Low
Exterior Wall: Wood Sheathing
Roof Shape Type: Gable/Hip
Building Type: Single Family

Property Information
Subdivision Name: NORTH ADD
Living Sq. Ft: 1,054
Adjusted Gross Sq. Ft: 1,160
Ground Floor Sq. Ft: 812
Building Sq. Ft: 1,554
# of Stories: 1
Legal Description: PARCEL SHOWN ON PLAT BOOK P PAGE 10 MARKED NOT INCLUDED & THAT PORTION OF LOT 3BLK A IN DAVIS SHORES S/123 DESC AS BEGNE COR OF LOT 3 TH S 17 DEG E 50 FT S 72DEG W 45 FT N 17 DEG W 50 FT N 72 DEG E45 FT TO POB IN SEC 08-23-28

Parking & Garage Information
Parking Type: Unfinished Detached Garage
Garage/Parking Sq. Ft: 360
Garage / Carport Type: Unfinished Detached

Lot Information
# of Buildings: 1
Land Sq. Ft: 17,750
Legal Lot Number: 3
Legal Block Number: A
Municipality Name: WINDERMERE
Acres: 0.4075
Zoning Code: SFR
County Use Description: SINGLE FAMILY CANAL
State Use Description: SINGLE FAMILY

Financial

Assessor Information
Assessment Year: 2025
Tax District County: 75

Public facts

Beds: 2
Baths: 1.0
Sq. Ft.: 1,054
Stories: 1.0
Lot Size: 0.41 acres
Style: Single Family Residential
Year Built: 1922
Year Renovated: 1963
County: Orange County
APN: 282308000000004

Home facts updated by county records on Aug 17, 2026

Around this home

Schools

Windermere Elementary School

Public PreK-5 • Assigned • 0.6mi

10/10

Gotha Middle School

Public 6-8 • Assigned • 2.2mi

6/10

Olympia High School

Public 9-12 • Assigned • 1.9mi

5/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 108° expected this year, 23 days in 30 years

9/10 Wind Factor

99% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Windermere, FL • 34786

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 6.7 hours in December, placing it above the U.S. average for solar exposure.

8.7 hrs

6.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$556,000 – $672,000

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EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

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OPEN TODAY, 1PM TO 3PM

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2 beds2.5 baths1,280 sq ft

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OPEN TODAY, 12PM TO 3PM

$400,000

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14500 Bridgewater Crossings Blvd, Windermere, FL 34786

3D WALKTHROUGH

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OPEN TODAY, 1PM TO 3PM3D WALKTHROUGH

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Home values near 55 Main St

Data from public records.

Address	Redfin Estimate
58 Main St, Windermere, FL 6 Beds \| 4 Baths \| 4875 Sq. Ft.	$2,503,398
30 Main St, Windermere, FL 4 Beds \| 4 Baths \| 2950 Sq. Ft.	$1,775,656

Address	Redfin Estimate
48 Main St, Windermere, FL 4 Beds \| 3 Baths \| 3844 Sq. Ft.	$1,640,084
20 Main St, Windermere, FL 5 Beds \| 3.5 Baths \| 5215 Sq. Ft.	$3,956,583

Address	Redfin Estimate
40 Main St, Windermere, FL 5 Beds \| 4.5 Baths \| 3907 Sq. Ft.	$2,442,959
79 Main St, Windermere, FL 5 Beds \| 4 Baths \| 4343 Sq. Ft.	$1,641,125

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 34786, FL

Sale history for 55 Main St

Tax history for 55 Main St

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 34786

Home values near 55 Main St

More real estate resources