40 Main St, Windermere, FL 34786
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OFF MARKET

40 Main St
Windermere, FL 34786

  • 5 Beds
  • 4.5 Baths
  • 3,907 sqft (on 0.55 acres)

$2,801,800

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $19,363/mo*
Refinance Your Home

$2,801,800

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $19,363/mo*
Refinance Your Home
5 Beds
4.5 Baths
3,907 sqft
(on 0.55 acres)

Home Value

Trulia Estimate
$2.8M
Since last month
Increased$3K (+0.1%)
Since last year
Increased$175K (+6.7%)
Since last sale
Increased$1M (+92.5%)
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 +87% in the last 10 years
MonthEstimated value
2026
August 2026$2.77M
July 2026$2.72M
June 2026$2.77M
May 2026$2.72M
April 2026$2.7M
March 2026$2.68M
February 2026$2.65M
January 2026$2.57M
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
0.17
Single-Family Home
$2,200,000
07/31/26
5
4.5
4,284
106 PALM STREET, Windermere, FL
0.25
Single-Family Home
$1,375,000
06/11/26
5
4.5
3,082
409 W 2ND AVENUE, Windermere, FL
0.28
Single-Family Home
$2,250,000
03/09/26
5
4.5
4,688
84 OAKDALE ST, Windermere, FL
0.14
Single-Family Home
$1,750,000
06/23/26
4
5
3,519
105 PINE STREET, Windermere, FL
0.28
Single-Family Home
$2,335,000
06/10/26
5
5.5
5,696
11018 LAKE BUTLER BOULEVARD, Windermere, FL
0.34
Single-Family Home
$3,100,000
09/02/25
4
3.5
3,923
65 OAKDALE STREET, Windermere, FL
0.16
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
2 OAKDALE STREET, Windermere, FL
0.15
Single-Family Home
$1,160,000
01/09/26
3
2
2,152
11 Main St, Windermere, FL
0.10
Single-Family Home
$1,200,000
09/15/25
3
2
1,638
800 W 2ND AVENUE, Windermere, FL
0.58
Single-Family Home
$2,400,000
09/05/25
5
4.5
5,511

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
33 MAIN STREET, Windermere, FL 34786
0.07
$1,572,000
4
2
2,130
For Sale
50 FOREST STREET, Windermere, FL 34786
0.07
$7,444,900
6
5.5
7,388
Off Market
19 MAIN STREET, Windermere, FL 34786
0.09
$2,792,500
4
3
2,331
Off Market
2807 BUTLER BAY DRIVE N, Windermere, FL 34786
0.07
$2,490,000
5
4.5
4,876
Off Market
7 1ST COURT, Windermere, FL 34786
0.10
$2,811,500
4
3
3,149
Off Market
2 OAKDALE STREET, Windermere, FL 34786
0.15
$1,160,000
3
2
2,152
Recently Sold
76 OAKDALE STREET, Windermere, FL 34786
0.13
$1,056,100
3
1.5
2,011
Off Market
212 W 1ST AVENUE, Windermere, FL 34786
0.14
$1,650,000
4
2
2,627
For Sale
84 OAKDALE ST, Windermere, FL 34786
0.14
$1,750,000
4
5
3,519
Recently Sold
57 OAKDALE STREET, Windermere, FL 34786
0.15
$1,219,200
3
2
1,637
Off Market
116 MAIN STREET, Windermere, FL 34786
0.14
$687,800
3
2
1,269
Off Market
116 MAIN STREET LOT 434, Windermere, FL 34786
0.14
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 40 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
2004
Lot Size
0.55 acres
Living Area
3,907 sqft
Price/Sqft
$717
Parking
Garage

About this House

Live the Butler Chain lifestyle in this Key West style home in the town of Windermere with 100 feet of waterfront on Wauseon Bay. Enjoy nightly sunsets in this beautifully maintained custom built home from nearly every room or while in your screened in back porch with tongue and groove ceilings and wet bar, from your custom dock or swimming in the lake! 4 ensuite bedrooms, 1st floor half bath and super outdoor shower are features of this block construction home with standing seam metal roof, energy efficient low E dual pane windows, Plantation shutters, Patagonian Rosewood floors, 12 ft.ceilings, crown moulding and wood burning fireplace. The open floor plan has large windows and french doors overlooking Wauseon Bay and boasts a gourmet chefs kitchen with food prep island w/wine refrigerator, Sub Zero refrigerator, Viking gas cooktop, Wolf convection oven and large breakfast bar. Sliding doors in the master suite lead out to the patio and yard overlooking the lake and bathroom retreat features garden tub, shower with floor to ceiling subway tile and waterfall shower head. Enjoy your own private dock where you can easily access your boat to explore the 11 pristine lakes of the Butler Chain. The 2nd floor is perfect for guests and watching movies with 2 bedrooms, full bath, media room, wet bar and fabulous private balcony. Walking distance to the town square, Windermere elementary, Friday farmers market, food trucks, restaurants and shops. New A/C 2018, professionally painted inside/out June 2019.
40 Main St, Windermere, FL 34786 is a 5 bedroom, 5 bathroom, 3,907 sqft single-family home built in 2004. It last sold for $1,440,000 on Sep 20, 2019. It is currently off market. The Trulia Estimate is $2,801,800, with a rent estimate of $6,858/month.

Home Details for 40 Main St

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet

Exterior Features

Exterior Home Features
Roof: MetalExterior: Block
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 2004Year Updated: 2004
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.55 acres

Additional Information

On Site Laundry Available

Price and Tax history

DateEventPrice
Nov 22, 2019
Source: Agent Provided
ListingRemoved
$1,550,000
Oct 31, 2019
Source: Agent Provided
Pending
$1,550,000
Oct 31, 2019
Source: Agent Provided
Listed For Sale
$1,550,000
Sep 20, 2019
Source: N/A
Sold
$1,440,000
Jun 6, 2019
Source: Agent Provided
Listed For Sale
$1,550,000

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
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  • 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
    Flag
  • 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

80 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

81 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

78 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 40 Main St

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Off Market Homes Near 40 Main St

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Frequently asked questions about 40 Main St

  • What is 40 Main St estimated to be worth?
    Trulia's estimated value for 40 Main St in Windermere, FL is $2,801,800.
  • What is the price history for 40 Main St?
    40 Main St in Windermere, FL last sold for $1,440,000 in September 2019.
  • 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 40 Main St have air conditioning?
    Yes, 40 Main St in Windermere, FL has air conditioning.
  • Does 40 Main St have laundry facilities?
    Yes, 40 Main St in Windermere, FL has laundry facilities.