58 Main St, Windermere, FL 34786
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OFF MARKET

58 Main St
Windermere, FL 34786

  • 5 Beds
  • 3 Baths
  • 4,257 sqft (on 0.58 acres)

$3,423,200

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $23,641/mo*
Refinance Your Home

$3,423,200

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $23,641/mo*
Refinance Your Home
5 Beds
3 Baths
4,257 sqft
(on 0.58 acres)

Home Value

Trulia Estimate
$3.42M
Since last month
Decreased$8K (-0.2%)
Since last year
Increased$646K (+23.5%)
Since last sale
Increased$2M (+142.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +146% in the last 10 years
MonthEstimated value
2026
August 2026$3.4M
July 2026$3.42M
June 2026$3.4M
May 2026$3.41M
April 2026$3.42M
March 2026$3.45M
February 2026$3.5M
January 2026$2.75M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
81 OAKDALE STREET, Windermere, FL
0.15
Single-Family Home
$2,200,000
07/31/26
5
4.5
4,284
409 W 2ND AVENUE, Windermere, FL
0.26
Single-Family Home
$2,250,000
03/09/26
5
4.5
4,688
106 PALM STREET, Windermere, FL
0.24
Single-Family Home
$1,375,000
06/11/26
5
4.5
3,082
65 OAKDALE STREET, Windermere, FL
0.14
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
105 PINE STREET, Windermere, FL
0.27
Single-Family Home
$2,335,000
06/10/26
5
5.5
5,696
84 OAKDALE ST, Windermere, FL
0.12
Single-Family Home
$1,750,000
06/23/26
4
5
3,519
412 FOREST STREET, Windermere, FL
0.38
Single-Family Home
$765,000
07/30/26
5
2.5
2,539
76 OAKDALE STREET, Windermere, FL
0.11
Single-Family Home
$1,060,000
09/11/25
3
1.5
2,011
2 OAKDALE STREET, Windermere, FL
0.17
Single-Family Home
$1,160,000
01/09/26
3
2
2,152
11 Main St, Windermere, FL
0.13
Single-Family Home
$1,200,000
09/15/25
3
2
1,638

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
2807 BUTLER BAY DRIVE N, Windermere, FL 34786
0.04
$2,490,000
5
4.5
4,876
Off Market
50 FOREST STREET, Windermere, FL 34786
0.07
$7,444,900
6
5.5
7,388
Off Market
212 W 1ST AVENUE, Windermere, FL 34786
0.11
$1,650,000
4
2
2,627
For Sale
116 MAIN STREET, Windermere, FL 34786
0.11
$687,800
3
2
1,269
Off Market
116 MAIN STREET LOT 434, Windermere, FL 34786
0.11
-
-
-
-
Off Market
7 1ST COURT, Windermere, FL 34786
0.12
$2,811,500
4
3
3,149
Off Market
33 MAIN STREET, Windermere, FL 34786
0.08
$1,572,000
4
2
2,130
For Sale
76 OAKDALE STREET, Windermere, FL 34786
0.11
$1,056,100
3
1.5
2,011
Off Market
111 MAIN STREET, Windermere, FL 34786
0.13
$849,000
3
2
2,272
Recently Sold
84 OAKDALE ST, Windermere, FL 34786
0.12
$1,750,000
4
5
3,519
Recently Sold
19 MAIN STREET, Windermere, FL 34786
0.11
$2,792,500
4
3
2,331
Off Market
133 MAIN STREET, Windermere, FL 34786
0.15
$635,800
3
2
1,166
Off Market

Local Information

  • Map ViewExplore the area around 58 Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1953
Lot Size
0.58 acres
Living Area
4,257 sqft
Price/Sqft
$804
Parking
Garage

About this House

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.
58 Main St, Windermere, FL 34786 is a 5 bedroom, 3 bathroom, 4,257 sqft single-family home built in 1953. It last sold for $1,400,000 on Jun 30, 2005. It is currently off market. The Trulia Estimate is $3,423,200, with a rent estimate of $6,326/month.

Home Details for 58 Main St

Interior Features

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

Exterior Features

Exterior Home Features
Roof: CompositionDeckGardenPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1953Year Updated: 2000
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.58 acres

Price and Tax history

DateEventPrice
Jun 21, 2026
Source: Stellar MLS #O6370886
ListingRemoved
$3,725,000
Feb 6, 2026
Source: Stellar MLS #O6370886
Listed For Sale
$3,725,000
Nov 23, 2015
Source: Agent Provided
ListingRemoved
$1,635,500
Oct 29, 2015
Source: Agent Provided
PriceChange
$1,635,500
Price decreased by 4%
Sep 26, 2015
Source: Agent Provided
Listed For Sale
$1,698,500

Market trends in Windermere

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
296
11MoM
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Around this home

View nearby schools on GreatSchools
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 271 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

  • 80 % 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.
  • 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."
    0
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • 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."
    0
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  • 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. "
    0
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  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
    Flag
  • 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."
    0
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • 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. "
    0
    Flag
  • 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."
    5
    Flag
  • 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."
    3
    Flag
  • 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."
    0
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  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • 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."
    2
    Flag
  • 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."
    0
    Flag
  • 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."
    2
    Flag
  • 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. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
    Flag
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
    Flag
  • 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! "
    0
    Flag
  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • 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. "
    0
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  • 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 "
    0
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • 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."
    1
    Flag
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
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  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
    Flag
  • 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. "
    1
    Flag
  • 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"
    0
    Flag
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • 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. "
    1
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

45 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

67 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

81 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

81 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

81 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

21 rentals with an outdoor space in Windermere, FL

Homes for sale near 58 Main St

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Off Market Homes Near 58 Main St

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Frequently asked questions about 58 Main St

  • What is 58 Main St estimated to be worth?
    Trulia's estimated value for 58 Main St in Windermere, FL is $3,423,200.
  • What is the price history for 58 Main St?
    58 Main St in Windermere, FL last sold for $1,400,000 in June 2005.
  • Is Windermere a buyer's or seller's market?
    Windermere is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windermere?
    The median sale price in Windermere is $814K. That is up $92.5K from the prior month.
  • Does 58 Main St have air conditioning?
    Yes, 58 Main St in Windermere, FL has air conditioning.
  • Does 58 Main St have a pool?
    Yes, 58 Main St in Windermere, FL has a pool.