58 Main St, Windermere, FL 34786
FOR SALE
3D VIEW
0.58 ACRES

58 Main St
Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 4,875 sqft (on 0.58 acres)

$3,725,000

Est. Mortgage $24,919/mo*

$3,725,000

Est. Mortgage $24,919/mo*
5 Beds
4 Baths
4,875 sqft
(on 0.58 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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
91 days ago

Home Details for 58 Main St

Interior Features

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

Exterior Features

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

Days on Market

Cumulative Days on Market: 61Days on Market: 91

Property Information

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

Price & Status

Price
List Price: $3,725,000Price Per Sqft: $764

Active Status

MLS Status: Active

Location

Direction & Address
City: WINDERMERECommunity: LAKE BUTLER PARK PT REP

Agent Information

Listing Agent
Listing ID: O6370886

Building

Building Area
Building Area: 6355 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.58 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

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 4 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

Price History for 58 Main St

DatePriceEventSource
02/06/2026$3,725,000Listed For SaleStellar MLS #O6370886
11/23/2015$1,635,500ListingRemovedAgent Provided
10/29/2015$1,635,500PriceChange
Agent Provided
09/26/2015$1,698,500Listed For SaleAgent Provided
11/30/2007$1,585,000ListingRemovedAgent Provided
11/14/2007$1,585,000Listed For SaleAgent Provided
06/30/2005$1,400,000Sold
Stellar MLS #S4587918
06/11/2003$560,000Sold
N/A
08/22/1996$408,000Sold
N/A

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Property Tax and Assessment

Year2024
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.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "

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.