58 Main St
Windermere, FL 34786
- 5 Beds
- 4 Baths
- 4,875 sqft (on 0.58 acres)
5 Beds
4 Baths
4,875 sqft
(on 0.58 acres)
Local Information
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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 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.
Home Highlights
Parking
3 Car Garage
Outdoor
Porch, Pool
View
Water, Lake
HOA
None
Price/Sqft
$764
Listed
92 days ago
Home Details for 58 Main St
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Interior Details Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 3, Bedroom 5, Primary Bathroom, Bathroom 1, Bathroom 2, Den, Family Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 4 |
Dimensions and Layout Living Area: 4875 Square Feet |
Appliances & Utilities Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water ConnectedAppliances: Oven, Convection Oven, Dishwasher, Disposal, Gas Water Heater, Microwave, RefrigeratorDishwasherDisposalLaundry: Inside,Laundry RoomMicrowaveRefrigerator |
Heating & Cooling Heating: ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric |
Fireplace & Spa Fireplace: GasHas a Fireplace |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Window: Blinds, Double Pane Windows, Shutters, Window TreatmentsDoor: Outdoor Grill, Sliding DoorsFlooring: Engineered Hardwood, Tile, Hardwood |
Levels, Entrance, & Accessibility Stories: 2Number of Stories: 2Levels: TwoFloors: Engineered Hardwood, Tile, Hardwood |
View Has a ViewView: Water, Lake |
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Exterior Home Features Roof: ShinglePatio / Porch: Rear PorchFencing: FencedExterior: Irrigation System, Lighting, Outdoor Grill, Rain GuttersFoundation: SlabHas a Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Garage Door Opener,Golf Cart Garage |
Pool Pool: Gunite, In Ground, Salt WaterPool |
Frontage WaterfrontWaterfront: Lake Front, Lake - Chain of Lakes, Lake Privileges, Lift, Lift - CoveredResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Dirt, GravelOn Waterfront |
Water & Sewer Sewer: Septic TankWater Body: LAKE BUTLER WAUSEON BAY |
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Cumulative Days on Market: 61Days on Market: 92 |
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Year Built Year Built: 1953 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional |
Building Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels |
Property Information Parcel Number: 082328434800080 |
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Price List Price: $3,725,000Price Per Sqft: $764 |
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MLS Status: Active |
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Direction & Address City: WINDERMERECommunity: LAKE BUTLER PARK PT REP |
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Listing Agent Listing ID: O6370886 |
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Building Area Building Area: 6355 Square Feet |
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Not Senior Community |
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Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee |
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Lot Area: 0.58 acres |
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Special Conditions: None |
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Listing Terms: Cash, Conventional |
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Business Information Ownership: Fee Simple |
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Mls Number: O6370886Water ViewWater View: Water, LakeShowing Advance Notice: 24Showing AttendedShowing Considerations: Security SystemShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12095-N-082328434800080-R-N |
Last check for updates: about 5 hours ago
Listing Provided by: Michelle Ingrassia, (407) 756-9164
LPT REALTY, LLC, (877) 366-2213
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6370886

Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Price History for 58 Main St
| Date | Price | Event | Source |
|---|---|---|---|
| 02/06/2026 | $3,725,000 | Listed For Sale | Stellar MLS #O6370886 |
| 11/23/2015 | $1,635,500 | ListingRemoved | Agent Provided |
| 10/29/2015 | $1,635,500 | PriceChange | Agent Provided |
| 09/26/2015 | $1,698,500 | Listed For Sale | Agent Provided |
| 11/30/2007 | $1,585,000 | ListingRemoved | Agent Provided |
| 11/14/2007 | $1,585,000 | Listed For Sale | Agent Provided |
| 06/30/2005 | $1,400,000 | Sold | Stellar MLS #S4587918 |
| 06/11/2003 | $560,000 | Sold | N/A |
| 08/22/1996 | $408,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $21,723 |
| Assessment | $2,042,668 |
Home facts updated by county records
Comparable Sales for 58 Main St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.26 | Single-Family Home | $2,250,000 | 03/09/26 | 5 | 4.5 | 4,688 | |
0.14 | Single-Family Home | $1,050,000 | 10/31/25 | 4 | 2 | 2,191 | |
0.37 | Single-Family Home | $3,100,000 | 09/02/25 | 4 | 3.5 | 3,923 | |
0.57 | Single-Family Home | $2,400,000 | 09/05/25 | 5 | 4.5 | 5,111 | |
0.11 | Single-Family Home | $1,060,000 | 09/11/25 | 3 | 1.5 | 2,011 | |
0.17 | Single-Family Home | $1,160,000 | 01/09/26 | 3 | 2 | 2,152 | |
0.34 | Single-Family Home | $862,000 | 01/08/26 | 4 | 3 | 2,410 | |
0.56 | Single-Family Home | $4,125,000 | 09/05/25 | 5 | 5 | 4,783 |
Assigned Schools
These are the assigned schools for 58 Main St.
What Locals Say about Windermere
At least 270 Trulia users voted on each feature.
93 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say car is needed
87 % Say parking is easy
81 % Say people would walk alone at night
80 % Say it's quiet
79 % Say there's holiday spirit
78 % Say kids play outside
75 % Say streets are well-lit
64 % Say yards are well-kept
60 % Say they plan to stay for at least 5 years
59 % Say it's walkable to grocery stores
56 % Say there's wildlife
55 % Say it's walkable to restaurants
54 % Say neighbors are friendly
40 % Say there are community events
Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Michelle Ingrassia, LPT REALTY, LLC, (877) 366-2213
Agent Phone: (407) 756-9164

58 Main St, Windermere, FL 34786 is a 5 bedroom, 4 bathroom, 4,875 sqft single-family home built in 1953. This property is currently available for sale and was listed by Stellar MLS on Feb 6, 2026. The MLS # for this home is MLS# O6370886.

