58 Main St
Windermere, FL 34786
- 5 Beds
- 3 Baths
- 4,257 sqft (on 0.58 acres)
5 Beds
3 Baths
4,257 sqft
(on 0.58 acres)
Local Information
-- mins to
Description
Enjoy the quaint lifestyle along the shores of the renowned Butler Chain of Lakes. Located in the heart of Old Town Windermere, this complete 2003 remodel boasts relaxing lake views, a spacious floor plan, vaulted ceilings and a beautiful uninterrupted row of French glass doors that guarantee you'll never miss a sunset from any practically every room in the house. This block construction home features hardwood floors, porcelain tile and crown molding throughout. Enjoy the large kitchen with 42" custom cabinets, granite counter tops, a GE trash compactor and a large island with a cook top sure to make any chef smile. Escape into your master retreat with expansive lake and sunset views, your own private balcony, on suite office and dry bar. Master bath consists of dual sinks, a jetted garden tub and a huge walk in closet for the most enthusiast of shoppers. Entertain your friends and family along side your salt water pool and large back yard. After a full day of skiing the lake park your boat in your roof covered Trex boat dock. Enjoy Old Windermere charm at its finest with short walks to the weekly farmer's market, shopping, dining, parks and A+ rated schools.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 58 Main St
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Heating & Cooling Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 1Floors: Tile, Hardwood |
Interior Details Types of Rooms: Walk In Closet, Dining RoomCeiling Fan |
Appliances & Utilities DishwasherRefrigerator |
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Exterior Home Features Roof: CompositionDeckGardenPatioPorch |
Pool Pool |
Parking & Garage GarageParking: Carport, Garage Attached |
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Year Built Year Built: 1953Year Updated: 2000 |
Property Type / Style Property Type: Single Family Home |
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Units in Building: 1 |
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Lot Area: 0.58 acres |
Price History for 58 Main St
| Date | Price | Event | Source |
|---|---|---|---|
| 06/21/2026 | $3,725,000 | ListingRemoved | Stellar MLS #O6370886 |
| 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 |
Market trends in Windermere
Last updated May 2026
Avg. sale price
$672K
$26.67KMoM
Sale-to-List Price
97.5%
0.3%MoM
Price per sq ft
$262
$6MoM
Available listings
291
2MoM
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 | |
0.24 | Single-Family Home | $1,375,000 | 06/11/26 | 5 | 4.5 | 3,082 | |
0.46 | Single-Family Home | $1,248,800 | 07/16/25 | 4 | 4 | 3,829 | |
0.14 | Single-Family Home | $1,050,000 | 10/31/25 | 4 | 2 | 2,191 | |
0.27 | Single-Family Home | $2,335,000 | 06/10/26 | 5 | 5.5 | 5,696 | |
0.12 | Single-Family Home | $1,750,000 | 06/23/26 | 4 | 5 | 3,519 | |
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 | |
0.13 | Single-Family Home | $1,200,000 | 09/15/25 | 3 | 2 | 1,638 | |
0.34 | Single-Family Home | $862,000 | 01/08/26 | 4 | 3 | 2,410 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.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
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 58 Main St
Off Market Homes Near 58 Main St
58 Main St, Windermere, FL 34786 is a 5 bedroom, 3 bathroom, 4,257 sqft single-family home built in 1953. This property is not currently available for sale. 58 Main St was last sold on Jun 30, 2005 for $1,400,000. The current Trulia Estimate for 58 Main St is $3,416,000.

