Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$3,725,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 4,875 Sq. Ft.
  • Updated 23 hours ago
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 58 Main St

General

  • Price: $3,725,000
  • Taxes: $21,723 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6370886
  • Updated: 2/5/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), High Ceilings, Kitchen and Family Room Combination, 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
  • Fireplace: Yes
  • Fireplace(s): Gas
  • Appliances: Built-In Oven, Convection Oven, Dishwasher, Disposal, Gas Water Heater, Microwave, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Engineered Hardwood, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Salt Water

Exterior

  • Exterior Features: Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors
  • Deck/Patio: Rear Porch
  • Porch/Patio/Deck: Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener, Golf Cart Garage

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: LAKE BUTLER PARK PT REP
  • Driving Directions: Main street to North house on the right
  • Direction Faces: Northeast

Community

  • Community Name: 34786 - Windermere

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Septic Tank
  • Water District: LAKE BUTLER WAUSEON BAY
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Traditional
  • Architectural Style: Traditional
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Blinds, Double Pane Windows, Shutters, Window Treatments
  • Stories/Levels: Two
  • Square Feet: 4,875
  • Sq. Ft. Source: Public Records
  • Year Built: 1953

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.58
  • Lot Size (Sq. Ft.): 25,329
  • Lot Size: 25329
  • Street/Road Desc.: Dirt, Gravel
  • Fencing (Description): Fenced

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake, Lake - Chain of Lakes
  • Water Extras: Yes
  • Water Front Name: LAKE BUTLER WAUSEON BAY
  • Water Front Desc.: Lake Front, Lake - Chain of Lakes

Financial Considerations

  • Tax Amount: $21,723.13
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: REPLAT PART OF LAKE BUTLER PARK R/39 LOTS 8 & 9
  • Flood Zone Info: X
  • APN: 82328434800080
  • Property ID: 82328434800080

Listed by Lpt Realty, Llc

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 58 Main St —

  • Lpt Realty, Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 58 Main St

School District:Orange County School District
NameGradesDistance
Windermere Elementary School
11125 Park Avenue, Windermere, FL 34786
K-50.6 mi
Gotha Middle School
9155 Gotha Road, Windermere, FL 34786
6-82.2 mi
Olympia High School
4301 South Apopka Vineland Road, Orlando, FL 32835
9-121.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 58 Main St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/05/2026
Listed
$3,725,000
166.07%
MLS
7/18/2005
Sold
$1,400,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 58 Main St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$21,723
—
$1,365,798
3%
2024
$21,723
3%
$1,327,306
3%
2023
$21,027
21%
$1,288,647
23%
2021
$17,410
-15%
$1,048,886
-16%
2022
$20,412
17%
$1,251,114
21%
2021
$17,410
2%
$1,030,460
2%
2019
$17,125
1%
$1,007,292
2%
2018
$16,978
4%
$988,510
2%
2017
$16,260
—
$968,178
2%
2016
$16,254
-2%
$948,264
1%
2015
$16,516
3%
$941,672
3%
2014
$16,003
2%
$917,333
2%
2013
$15,682
—
$903,776
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 58 Main St

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Lpt Realty, Llc

Similar Properties near 58 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2844 Marquesas Ct, Windermere, FL 34786 - Photo 1
$3,700,000

2844 Marquesas Ct  Windermere, FL 34786

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 5,365
    Sq. Ft.
Listed by Douglas Elliman
5050 Isleworth Country Club Dr, Windermere, FL 34786 - Photo 1
$3,690,000

5050 Isleworth Country Club Dr  Windermere, FL 34786

  • Single Family
  • Active
  • Updated 13 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 3,365
    Sq. Ft.
Listed by Compass Florida Llc
12812 Jacob Grace Ct, Windermere, FL 34786 - Photo 1
$3,725,000

12812 Jacob Grace Ct  Windermere, FL 34786

  • Single Family
  • Active
  • 4
    Beds
  • 5
    Total Baths
  • 6,054
    Sq. Ft.
Listed by Exp Realty Llc
10870 Bayshore Dr, Windermere, FL 34786 - Photo 1
$3,300,000
Open House

10870 Bayshore Dr  Windermere, FL 34786

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 4,693
    Sq. Ft.
Listed by One Luxury International Llc

Just Listed near 58 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

10600 Oakview Pointe Terrace, Gotha, FL 34734 - Photo 1 Just Listed
$859,000

10600 Oakview Pointe Terrace  Gotha, FL 34734

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,338
    Sq. Ft.
Listed by Century 21 Carioti
1602 Starfire Ln, Ocoee, FL 34761 - Photo 1 Just Listed
$234,500

1602 Starfire Ln  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 7 hours ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,350
    Sq. Ft.
Listed by Berkshire Hathaway Homeservices Results Realty
2040 Milkweed St, Ocoee, FL 34761 - Photo 1 Just Listed
$325,000

2040 Milkweed St  Ocoee, FL 34761

  • Townhouse
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,574
    Sq. Ft.
Listed by Morgan Property Solutions Inc
214 Highbrooke Blvd, Ocoee, FL 34761 - Photo 1 Just Listed
$649,000

214 Highbrooke Blvd  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 15 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,208
    Sq. Ft.
Listed by Upside Real Estate Inc

Price Reduced near 58 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

2254 Blackjack Oak St, Ocoee, FL 34761 - Photo 1 Price Reduced
-$25,000 (-3.85%)
$625,000

2254 Blackjack Oak St  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,260
    Sq. Ft.
Listed by Milton James (407) 572-4458
528 Herring Gull Ct, Ocoee, FL 34761 - Photo 1 Price Reduced
-$10,000 (-1.9%)
$515,000

528 Herring Gull Ct  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,561
    Sq. Ft.
Listed by Keller Williams Suburban Tampa
1008 Desert Candle Dr, Ocoee, FL 34761 - Photo 1 Price Reduced
-$10,000 (-2.67%)
$365,000

1008 Desert Candle Dr  Ocoee, FL 34761

  • Townhouse
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,570
    Sq. Ft.
Listed by Kings Realty & Co Llc
1737 N Lakewood Ave, Ocoee, FL 34761 - Photo 1 Price Reduced
-$10,999 (-2.76%)
$388,000

1737 N Lakewood Ave  Ocoee, FL 34761

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,504
    Sq. Ft.
Listed by Homecoin.Com

Recent Sales near 58 Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

805 W 2nd Ave, Windermere, FL 34786 - Photo 1 Sold
$4,125,000

805 W 2nd Ave  Windermere, FL 34786

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 4,783
    Sq. Ft.
Listed by Forever Magic Realty Inc
Sold by The Real Estate Collection Llc
10545 Down Lakeview Cir, Windermere, FL 34786 - Photo 1 Sold
$3,450,000

10545 Down Lakeview Cir  Windermere, FL 34786

  • Single Family
  • Closed
  • Updated 12 days ago
  • 5
    Beds
  • 7
    Total Baths
  • 7,263
    Sq. Ft.
Listed and Sold by Colonialtown Realty
9743 Chestnut Ridge Dr, Windermere, FL 34786 - Photo 1 Sold
$3,250,000

9743 Chestnut Ridge Dr  Windermere, FL 34786

  • Single Family
  • Closed
  • 5
    Beds
  • 7
    Total Baths
  • 6,328
    Sq. Ft.
Listed by Isleworth Realty Llc
Sold by Stockworth Realty Group
9915 Giffin Ct, Windermere, FL 34786 - Photo 1 Sold
$3,800,000

9915 Giffin Ct  Windermere, FL 34786

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 6,008
    Sq. Ft.
Listed by Stellar Non-Member Office
Sold by Isleworth Realty Llc and Lokation

58 Main Street, Windermere, FL 34786 (MLS# O6370886) is a Single Family property with 5 bedrooms and 4 full bathrooms. 58 Main Street is currently listed for $3,725,000 and was received on February 05, 2026. Want to learn more about 58 Main Street? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

Tour this property