58 Main St

Windermere, FL 34786

$3,725,000
Price
5
Beds
4,875 Sq. Ft.
$764 / Sq. Ft.
4,875
Sq. Ft.
$764
per Sq. Ft.
New
New

Description

Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat traffic and peaceful setting. Set on an oversized waterfront lot with western exposure, the home captures breathtaking lake views from nearly every room—delivering spectacular sunsets and a seamless indoor-outdoor lifestyle. Over 4800sq 5 bedrooms, 4 full bathrooms, Recently enhanced by renovations...Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat traffic and peaceful setting. Set on an oversized waterfront lot with western exposure, the home captures breathtaking lake views from nearly every room—delivering spectacular sunsets and a seamless indoor-outdoor lifestyle. Over 4800sq 5 bedrooms, 4 full bathrooms, Recently enhanced by renovations completed in 2020, the residence now features a newly added owner’s retreat with spa-inspired bathroom, thoughtfully designed to maximize comfort, privacy, and sweeping lake views. Additional updated interior in 2022 showcases refined craftsmanship and high-end finishes, including Provenza engineered hardwood flooring, vaulted tongue-and-groove ceilings, cedar beams, updated bathrooms, custom drapery, and plantation shutters. The large open kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, two oversized kitchen islands, a GE Profile refrigerator, and an Advantium double oven, all seamlessly connected to the main living areas. The great room opens effortlessly to the outdoor living spaces through fully retractable sliding doors, creating an ideal setting for gatherings of any size. Outdoor amenities rival those of a private resort, featuring a saltwater pool with pebble-tech finish and shallow lounging shelf, summer kitchen with natural gas Artisan grill, motorized patio screens, indoor/outdoor surround sound, and a luxury boat dock with electric cradle and Trex decking—perfect for enjoying the Butler Chain lifestyle year-round. Additional highlights include interior and exterior security systems, natural gas, city water, roof 2020, and a newer septic tank. Located just steps from downtown Windermere, residents enjoy a charming small-town atmosphere with farmers markets, cafés, local shops, and dining, while remaining only minutes from Restaurant Row and Orlando’s premier amenities. A rare opportunity to own a fully updated lakefront retreat in one of Central Florida’s most coveted communities.
  1. Listed by Michelle Ingrassia • Brokerage DRE #1064576 • LPT REALTY, LLC
    P: (407)-756-9164 C: (407)-756-9164 michelleirealtor@aol.com

Property Details for 58 Main Street

Architectural Style
Traditional
Subdivision Name
LAKE BUTLER PARK PT REP
Township
23
Garage Spaces
2
View
Water
Waterfront
Yes
Water View
Lake, Lake - Chain of Lakes
Furnished
Unfurnished
LISTING UPDATED: 02/06/2026 06:56 AM

Property Details for 58 Main Street

StatusActive
MLS #O6370886
Days on Market1
Taxes$21,723 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1953
Lot Size0.58 AC / 25,329 SF
CountyOrange County

Location

Listing Courtesy of LPT REALTY, LLC, Michelle Ingrassia
Add your commute

Building Information for 58 Main Street

Stories2Year Built1953Building Size-Lot Size0.58 AC / 25,329 SF

Payment Calculator

$19,965 per month

30 year fixed, 6.15% Interest

Principal and Interest

$18,155

Property Taxes

$1,810

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 58 Main Street

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 6355.0
  • Building Area Units: Square Feet
  • Direction Faces: Northeast
  • Directions: Main street to North house on the right
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 58
  • Street Name: MAIN
  • Street Suffix: STREET
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Driveway, Garage Door Opener, Golf Cart Garage
Taxes and HOA Information
  • Association Approval Required: No
  • Association: No
  • CDD: No
  • Tax Block: 00
  • Tax Book Number: R-39
  • Tax Legal Description: REPLAT PART OF LAKE BUTLER PARK R/39 LOTS 8 & 9
  • Tax Lot: 8
  • Tax Year: 2024
Property
Lot Information
  • Additional Parcels: No
  • Additional Water Information: Located on the Wauseon Bay of Lake Butler Chain of Lakes
  • Lot Features: City Lot, Oversized Lot
  • Parcel Number: 082328434800080
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake, Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE BUTLER WAUSEON BAY
  • Water Extras: Lift, Lift - Covered
  • Water Extras: Yes
  • Water: Lift, Lift - Covered
  • Zoning: SFR
  • Living Area: 4875
Property and Assessments
  • Year Built Numeric: 1953
  • Flood Zone Code: X
  • Flood Zone Date: 09-24-2021
  • Flood Zone Panel: 12095C0220H
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 28
  • Public Survey Section: 08
  • Dock YN: Yes
  • Dock Description: Dock - Composite, Dock w/Electric, Lift
  • Dock Lift Capacity: 25
  • Dock Dimensions: 50x30
Utilities
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Stucco
  • Exterior Features: Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors
  • Fencing: Fenced
  • Foundation Details: Slab
  • Levels: Two
  • Patio And Porch Features: Rear Porch
  • Pool Features: Gunite, In Ground, Salt Water
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Waterfront Features: Lake Front, Lake - Chain of Lakes
  • Waterfront Feet Total: 120
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 4
  • Additional Rooms: Inside Utility
  • Appliances: Built-In Oven, Convection Oven, Dishwasher, Disposal, Gas Water Heater, Microwave, Refrigerator
  • Cooling: Central Air
  • Fireplace Features: Gas
  • Fireplace: Yes
  • Flooring: Engineered Hardwood, Tile, Hardwood
  • Heating: Electric
  • Interior Features: Ceiling Fan(s), High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 10.0
  • Water View: Yes
  • Window Features: Blinds, Double Pane Windows, Shutters, Window Treatments
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0

Property History for 58 Main Street

DateEvent & SourcePriceAppreciation
Feb 5, 2026

Listed (Active)

MFRMLS #O6370886

$3,725,000—
Nov 23, 2015

Withdrawn

MFRMLS #O5393965

$1,635,500—
Sep 26, 2015

Listed (Active)

MFRMLS #O5393965

$1,698,500—
Jul 18, 2005

Sold (Public Record)

Public Record #161809677

$1,400,000

+54.6% / yr

Jun 30, 2005

Sold

MFRMLS #S4587918

$1,400,000—
Jun 13, 2005

Pending

MFRMLS #S4587918

—
May 3, 2005

Listed (Active)

MFRMLS #S4587918

$1,585,000—
Feb 28, 2005

Withdrawn

MFRMLS #O4581337

$1,450,000—
Sep 23, 2004

Listed (Active)

MFRMLS #O4581337

$1,450,000—
Jun 11, 2003

Sold (Public Record)

Public Record #114655036

$560,000—
DateEvent & SourcePrice
02/05/2026

Listed (Active)

MFRMLS #O6370886

$3,725,000
11/23/2015

Withdrawn

MFRMLS #O5393965

$1,635,500
09/26/2015

Listed (Active)

MFRMLS #O5393965

$1,698,500
07/18/2005

Sold (Public Record)

Public Record #161809677

$1,400,000

+54.6% / yr

06/30/2005

Sold

MFRMLS #S4587918

$1,400,000
06/13/2005

Pending

MFRMLS #S4587918

—
05/03/2005

Listed (Active)

MFRMLS #S4587918

$1,585,000
02/28/2005

Withdrawn

MFRMLS #O4581337

$1,450,000
09/23/2004

Listed (Active)

MFRMLS #O4581337

$1,450,000
06/11/2003

Sold (Public Record)

Public Record #114655036

$560,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 58 Main Street

Taxable ValueLand-Additions-Total-
Tax Record2024$21,723 ($1,810 / month)
Home Facts
Beds6Total Finished SqFt4,875 SqFtAbove Grade Finished SqFt4,875 SqFtStories2Lot Size25,330 SqFtStyleSingle Family ResidenceYear Built1953Year Renovated2000ZoningSFRCountyORANGEAPN08-23-28-4348-00-080

Schools near 58 Main Street

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Windermere Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Gotha Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Windermere Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Gotha Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 58 Main Street, Windermere, FL 34786

58 Main Street is a single family home for sale in Windermere, FL 34786. This property was listed for sale on February 5, 2026 by LPT REALTY, LLC, it's currently listed at $3,725,000. It has been on the market for a total of 1 days and was last sold on July 18, 2005. This listing's school district is Orange County Public Schools. Nearby schools include Windermere Elementary School, Cornerstone Academy Charter and Gotha Middle School. 58 Main Street is a 5-bed, 4-bath, 4,875 sqft single family home built in 1953.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of LPT REALTY, LLC, Michelle Ingrassia

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 02/06/2026 06:56 AM