Off market dec 2021 for $1M

$1,553,793

Est. refi paymentEst. refi $7,074/mo

•

2,160

sq ft

5 Main St, Windermere, FL 34786

About this home

Live among the lakes under a canopy of century-old oaks in downtown Windermere, one of the oldest communities in Orange County, and experience a waterfront lifestyle that’s second to none! This 2-story concrete block charmer is situated on a half-acre, professionally landscaped point lot with panoramic water views, complete with 375 linear feet of waterfront that is ideal for guest boat dockage and a relaxed lakeside lifestyle. The resort-style pool and lanai boast ample space for outdoor grilling and entertaining. Inside is a formal living room and dining room with a wood-burning fireplace, and a wall of formal book shelves and cabinets. Upgrades include a boat house with hydraulic lift, a jet ski port, a large new storage shed, a new roof in 2018, new HVAC in 2019, and new carpet and exterior and interior painting in 2021. This beautiful home is steps away from 11 community parks, community docks, tennis courts, rowing clubs, nature trails, and award-winning restaurants. Annual community runs, a weekly farmer’s market, and monthly food truck nights add to this all-encompassing and one of a kind location! This is a must see waterfront pool home located on the famed Butler Chain of Lakes in Old Windermere.

Single-familyProperty Type

1966Year Built

0.49 acresLot Size

$719Est. Price/Sq.Ft.

2 car garageParking

Listed by Kari Fleck • THE REAL ESTATE COLLECTION LLC

Bought with Patricia Cardoso • QUATTRO R E SOLUTIONS LLC

Redfin checked: a few seconds ago

•Source:Stellar MLS as Distributed by MLS Grid #O5949931

Redfin Estimate

$1,553,793

$492K since sold in December 2021$21K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 72.9% higher than the average sale price ($899K) of 6 comparable homes.

SOLD MAY 21, 2026
$1,050,000
A
4 beds3 baths2,412 sq ft
316 E 5th Ave, Windermere, FL 34786
SOLD JAN 8, 2026
$862,000
B
4 beds3 baths2,410 sq ft
299 W 4th Ave, Windermere, FL 34786
SOLD JUL 30, 2026
$765,000
C
5 beds2.5 baths2,539 sq ft
412 Forest St, Windermere, FL 34786
SOLD SEP 15, 2026
$825,000
D
3 beds2 baths1,935 sq ft
11155 Lake Butler Blvd, Windermere, FL 34786
SOLD AUG 11, 2026
$890,000
E
4 beds3 baths3,516 sq ft
1002 Oakdale St, Windermere, FL 34786
SOLD AUG 28, 2026
$1,000,000
F
3 beds2.5 baths2,795 sq ft
725 Oakdale St, Windermere, FL 34786

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Earn from this home

Sell

$691,521

Est. take-home

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Refinance

Est. cash available

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Rent

$4,072/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%

0.1% MoM

Median sale price

$890K

$10K MoM

Avg. days on market

51d

15 days MoM

Recently sold homes

197

17 MoM

New listings for sale

COMING SOON
8168 Boat Hook Loop #302, Windermere, FL 34786
$299,997
2 beds2 baths1,161 sq ft
8168 Boat Hook Loop #302, Windermere, FL 34786
$1,280,000
4 beds2.5 baths2,441 sq ft
104 E 1st Ave, Windermere, FL 34786
NEW 23 HRS AGO
$2,400,000
5 beds4 baths5,139 sq ft
12722 S Lake Sawyer Ln, Windermere, FL 34786
NEW 29 HRS AGO
$8,500,000
4 beds5 baths7,100 sq ft
5092 Isleworth Country Club Dr, Windermere, FL 34786
NEW 30 HRS AGO
$950,000
4 beds3 baths2,680 sq ft
8524 Vivaro Isle Way, Windermere, FL 34786
$6,950,000
7 beds7 baths8,722 sq ft
6113 Grosvenor Shore Dr, Windermere, FL 34786
3D WALKTHROUGH
$875,000
4 beds3 baths2,704 sq ft
11727 Delwick Dr, Windermere, FL 34786
3D WALKTHROUGH
$3,850,000
4 beds4.5 baths6,605 sq ft
4906 Aviva Garden Ct, Windermere, FL 34786
$2,350,000
4 beds5 baths4,169 sq ft
11532 Waterstone Loop Dr, Windermere, FL 34786
$565,000
3 beds2 baths2,147 sq ft
7271 Londale Blvd, Windermere, FL 34786
See all

Provided by Redfin

Sale history for 5 Main St

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O5949931

Dec 8, 2021

Sold

$1,062,000

$492/sq ft

Sep 14, 2021

Pending

—

Aug 30, 2021

Price Changed

$1,100,000

$509/sq ft

Aug 11, 2021

Relisted

—

Jun 11, 2021

Listed

$1,150,000

$532/sq ft

Stellar MLS as Distributed by MLS Grid #O5366896

Aug 8, 2015

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O4955946

Jun 1, 2010

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O4827475

May 9, 2008

Listing Removed

—

Stellar MLS as Distributed by MLS Grid #O4772348

Nov 30, 2007

Listing Removed

—

Public Records

Jun 9, 2003

Sold

$423,000

$196/sq ft

Public Records

Jun 1, 1976

Sold

$47,900

$22/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$19,436 (+128.4%)

$460,000 + $736,920

$1,196,920

2024

$8,509 (−6.3%)

$460,000 + $736,920

$1,196,920

2023

$9,078 (−40.4%)

$460,000 + $32,720

$492,720

2022

$15,240 (+76.0%)

$360,000 + $560,941

$920,941

2021

$8,659 (+7.1%)

$360,000 + $560,941

$920,941

2020

$8,081 (−5.8%)

$310,000 + $178,998

$488,998

2019

$8,575 (+5.9%)

$290,000 + $182,770

$472,770

2018

$8,095 (+2.7%)

$290,000 + $182,770

$472,770

2017

$7,884 (+2.7%)

$260,000 + $176,239

$436,239

2016

$7,676 (+0.3%)

$260,000 + $176,239

$436,239

2015

$7,655 (+9.9%)

$245,000 + $162,782

$407,782

2014

$6,963 (+2.3%)

2013

$6,805 (−0.5%)

2012

$6,839

Tax history for 5 Main St

Year

Property tax

Land + Additions

Assessment*

2025

$19,436 (+128.4%)

$460,000 + $736,920

$1,196,920

2024

$8,509 (−6.3%)

$460,000 + $736,920

$1,196,920

2023

$9,078 (−40.4%)

$460,000 + $32,720

$492,720

2022

$15,240 (+76.0%)

$360,000 + $560,941

$920,941

2021

$8,659 (+7.1%)

$360,000 + $560,941

$920,941

2020

$8,081 (−5.8%)

$310,000 + $178,998

$488,998

2019

$8,575 (+5.9%)

$290,000 + $182,770

$472,770

2018

$8,095 (+2.7%)

$290,000 + $182,770

$472,770

2017

$7,884 (+2.7%)

$260,000 + $176,239

$436,239

2016

$7,676 (+0.3%)

$260,000 + $176,239

$436,239

2015

$7,655 (+9.9%)

$245,000 + $162,782

$407,782

2014

$6,963 (+2.3%)

2013

$6,805 (−0.5%)

2012

$6,839

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

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.49 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Orange County

APN

282308194801090

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

Property details

Parking

Parking Information
Garage Dimensions: 28x20
Parking Features: Bath In Garage, Oversized
Garage Spaces: 2
Has Attached Garage
Has Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms: 4

Bathroom Information
# of Full Baths (Total): 3

Other Rooms Information
Additional Rooms: Attic,Formal Dining Room Separate
# of Rooms: 9

Fireplace Information
Has Fireplace
Fireplace Features: Family Room, Wood Burning

Heating & Cooling
Heating Information: Central
Cooling Information: Central Air

Interior Features
Interior Features: Ceiling Fans(s), Eat-in Kitchen, Walk-in Closet(s)
Window Features: Blinds, Shutters
Appliances: Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Refrigerator
Flooring: Carpet, Tile, Wood

Exterior

Building Information
Construction Materials: Block
Roof: Shingle

Exterior Features
Patio And Porch Features: Covered, Deck, Enclosed, Patio, Porch, Screened
Exterior Features: French Doors

Pool Information
Spa Features: In Ground
Has Private Pool
Pool Features: Gunite, In Ground, Screen Enclosure

Property Features
Universal Property Id: US-12095-N-082328194801090-R-N

Waterfront Information
On Waterfront
Waterfront Features: Canal - Freshwater
Water Body Name: LAKE DOWN/FISCHER CANAL
Waterfront Feet Total: 375
Water Frontage Feet Canal Fresh: 375
Water View Y/N: 1
Water View Description: Canal,Lake,Lake - Chain of Lakes
Water Access Y/N: 1
Water Access Description: Canal - Freshwater,Lake - Chain of Lakes
Water Extras Y/N: 1
Water Extras Description: Boathouse,Dock - Slip Deeded On-Site,Dock w/Electric,No Wake Zone,Seawall - Other,Skiing Allowed

Property Information
CDD Y/N: 0
Homestead Y/N: 0
Property Type: Residential
Property Sub Type: Single Family Residence
Property Condition: Completed
Other Structures: Shed(s)
Zoning: SFR

Land Information
Vegetation: Mature Landscaping, Trees/Landscaped
Total Acreage: 1/4 to less than 1/2

Lot Information
Lot Features: Paved
Lot Size Acres: 0.49
Road Surface Type: Asphalt
Lot Size Square Meters: 1983
Zoning Compatible YN: 1

Building Information
MFR_BuildingAreaTotalSrchSqM: 303.79

Financial

Tax Information
Tax Annual Amount: $8,081
Tax Year: 2020

Lease / Rent Details
Lease Restrictions YN: 1

Utilities

Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: BB/HS Internet Available, Electricity Connected, Sewer Connected, Sprinkler Recycled
Additional Water Information: The Butler Chain-of-Lakes consists of 11 interconnected waterbodies with a combined surface area of more than 5000 acres. Lake Down surface area is 884 acres.

Location

Multi-Unit Information
Unit Number YN: 0
Furnished: Unfurnished

HOA Information
Association Approval Required Y/N: 0

School Information
Elementary School: Windermere Elem
Middle Or Junior High School: Gotha Middle
High School: Olympia High

Location Information
Directions: I-4 to Conroy Rd, exit West on Conroy (right). Conroy-Windermere Rd to roundabout and 1st right off of roundabout onto Main St. Go though downtown Windermere. House in on the right before canal bridge.

Community Information
Community Features: Boat Ramp, Park, Playground, Tennis Courts
Pets Allowed: Yes

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 0.49 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Orange County
APN: 282308194801090

Home facts updated by county records on Aug 17, 2026

Other

Miscellaneous Information
Third Party YN: 1

Listing Information
Previous Status: Pending
Backups Requested YN: 1
Home Warranty YN: No

Listing Date Information
Days to Contract: 95
Status Contractual Search Date: 2021-12-08

Listing Price Information
Calculated List Price By Calculated Sq Ft: 509.26

Green Information
Green Verification Count: 0
Direction Faces: Northwest

Home Information
Living Area: 2160
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 200.67
Building Area Total: 3270
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Slab
Levels: Two
Security Features: Security System Owned

Around this home

Schools

Windermere Elementary School

Public PreK-5 • Assigned • 0.5mi

10/10

Gotha Middle School

Public 6-8 • Assigned • 2.1mi

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

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$1.48M – $1.79M

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New listings for sale in 34786

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NEW 30 HRS AGO

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3D WALKTHROUGH

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3D WALKTHROUGH

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Home values near 5 Main St

Data from public records.

Address	Redfin Estimate
40 Main Street, Windermere, FL 5 Beds \| 4.5 Baths \| 3907 Sq. Ft.	$2,517,251
14 Main Street, Windermere, FL 4 Beds \| 3.5 Baths \| 3295 Sq. Ft.	$2,807,332

Address	Redfin Estimate
30 Main Street, Windermere, FL 4 Beds \| 4 Baths \| 2950 Sq. Ft.	$1,793,859
8 Main Street, Windermere, FL 5 Beds \| 3 Baths \| 4846 Sq. Ft.	$2,021,360

Address	Redfin Estimate
20 Main Street, Windermere, FL 5 Beds \| 3.5 Baths \| 5215 Sq. Ft.	$4,027,843
25 Main Street, Windermere, FL 3 Beds \| 1 Baths \| 1158 Sq. Ft.	$534,795

Property information provided by Stellar MLS as Distributed by MLS Grid when last listed in 2021. This data may not match . Learn more.

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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 5 Main St

Tax history for 5 Main St

Public record

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 5 Main St

More real estate resources