63 Main St, Windermere, FL 34786
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OFF MARKET

63 Main St
Windermere, FL 34786

  • 2 Beds
  • 3 Baths
  • 2,186 sqft (on 0.33 acres)

$1,026,700

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $7,116/mo*
Refinance Your Home

$1,026,700

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $7,116/mo*
Refinance Your Home
2 Beds
3 Baths
2,186 sqft
(on 0.33 acres)

Home Value

Trulia Estimate
$1.03M
Since last month
Increased$2K (+0.2%)
Since last year
Decreased$26K (-2.5%)
Since last sale
Increased$278K (+37.1%)
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 +75% in the last 10 years
MonthEstimated value
2026
August 2026$1.03M
July 2026$1.03M
June 2026$1.02M
May 2026$1.02M
April 2026$1.01M
March 2026$1.02M
February 2026$1.02M
January 2026$995K
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
111 MAIN STREET, Windermere, FL
0.10
Single-Family Home
$849,000
07/01/26
3
2
2,272
76 OAKDALE STREET, Windermere, FL
0.05
Single-Family Home
$1,060,000
09/11/25
3
1.5
2,011
416 MAGNOLIA STREET, Windermere, FL
0.37
Single-Family Home
$820,000
03/06/26
2
1.5
2,115
65 OAKDALE STREET, Windermere, FL
0.09
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
2 OAKDALE STREET, Windermere, FL
0.16
Single-Family Home
$1,160,000
01/09/26
3
2
2,152
299 W 4TH AVENUE, Windermere, FL
0.34
Single-Family Home
$862,000
01/08/26
4
3
2,410
11 Main St, Windermere, FL
0.13
Single-Family Home
$1,200,000
09/15/25
3
2
1,638
412 FOREST STREET, Windermere, FL
0.38
Single-Family Home
$765,000
07/30/26
5
2.5
2,539
305 OAKDALE STREET, Windermere, FL
0.26
Single-Family Home
$710,000
05/19/26
2
1
1,424
415 E 6TH AVENUE, Windermere, FL
0.53
Single-Family Home
$710,000
02/19/26
3
2
1,784

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
0.02
$2,490,000
5
4.5
4,876
Off Market
76 OAKDALE STREET, Windermere, FL 34786
0.05
$1,056,100
3
1.5
2,011
Off Market
84 OAKDALE ST, Windermere, FL 34786
0.07
$1,750,000
4
5
3,519
Recently Sold
116 MAIN STREET, Windermere, FL 34786
0.10
$687,800
3
2
1,269
Off Market
116 MAIN STREET LOT 434, Windermere, FL 34786
0.10
-
-
-
-
Off Market
111 MAIN STREET, Windermere, FL 34786
0.10
$849,000
3
2
2,272
Recently Sold
33 MAIN STREET, Windermere, FL 34786
0.07
$1,572,000
4
2
2,130
For Sale
133 MAIN STREET, Windermere, FL 34786
0.13
$635,800
3
2
1,166
Off Market
65 OAKDALE STREET, Windermere, FL 34786
0.09
$1,050,000
4
2
2,191
Recently Sold
81 OAKDALE STREET, Windermere, FL 34786
0.10
$2,200,000
5
4.5
4,284
Recently Sold
107 E 2ND AVENUE, Windermere, FL 34786
0.13
$1,095,200
4
3
2,684
Off Market
57 OAKDALE STREET, Windermere, FL 34786
0.09
$1,219,200
3
2
1,637
Off Market

Local Information

  • Map ViewExplore the area around 63 Main St.
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Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2014
Lot Size
0.33 acres
Living Area
2,186 sqft
Price/Sqft
$470
Parking
Garage

About this House

Location! Location! Location! This property is located in the historic olde Town of Windermere...among the "world-class" Butler Chain of Lakes! This unique watersports home with direct canal access to the the protected Butler Chain of Lakes, has "peek-a-boo" views of Lake Down, and Wauseon Bay. Thoughtfully designed, this homestead has almost 6000 gross square feet of new low-maintenance, energy-efficient "green" construction, enveloping nearly 2200 square feet of conditioned living space. Enter into the spacious foyer bathed in natural light, which leads directly into the great room which features a chef's kitchen with dining space for 10, which flows seamlessly through a relaxing indoor/outdoor living space...the very definition of "open concept" design! Dozens of mature and native/exotic trees and shrubs adorn this well drained waterfront lot with vibrant foliage, fruitage, and flowers. Set sail from your own private dock, and explore the unique Butler Chain of Lakes, where pleasure-boating, and world-class fishing, skiing, and other watersports abound. Walk to historic downtown Windermere and enjoy shopping, restaurants and year-round community events, public parks and recreational facilities. Designated "Outstanding Florida Waters," the Butler Chain of Lakes surrounds this quaint/historic "old Florida" town. Her soft sand streets, neighborly residents, and abundant old growth trees, make this one of the most walkable communities in Central Florida. Welcome home!
63 Main St, Windermere, FL 34786 is a 2 bedroom, 3 bathroom, 2,186 sqft single-family home built in 2014. It last sold for $749,000 on Dec 3, 2021. More recently, it was listed as a rental in May 2025 with an asking price of $6,000 per month. That rental listing was removed on September 9, 2025. It is currently off market. The Trulia Estimate is $1,026,700, with a rent estimate of $4,022/month.

Home Details for 63 Main St

Interior Features

Heating & Cooling
Heating: Forced Air, Heat Pump, Radiant, ElectricAir ConditioningCooling System: Refrigerator, CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Concrete
Interior Details
Additional StorageAtticNumber of Rooms: 8Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, WorkshopStorageWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDryerWasher
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: Wood, Cement Concrete, MetalPatioPorch
Parking & Garage
GarageParking Spaces: 8Parking: Garage Attached

Property Information

Year Built
Year Built: 2014Year Updated: 2014
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Building

Levels, Entrance, & Accessibility
Disabled Access
Fitness & Sports
Tennis Court

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Sep 9, 2025
Source: Stellar MLS #O6307925
ListingRemoved
$4,800
Aug 13, 2025
Source: Stellar MLS #O6307925
PriceChange
$4,800
Price decreased by 4%
Aug 2, 2025
Source: Stellar MLS #O6307925
PriceChange
$5,000
Price decreased by 4%
Jul 12, 2025
Source: Stellar MLS #O6307925
PriceChange
$5,200
Price decreased by 4%
Jun 24, 2025
Source: Stellar MLS #O6307925
PriceChange
$5,400
Price decreased by 4%

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
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  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
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  • 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
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  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
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  • 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
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  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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

52 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

75 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

90 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

91 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

83 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

26 rentals with an outdoor space in Windermere, FL

Homes for sale near 63 Main St

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Off Market Homes Near 63 Main St

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Frequently asked questions about 63 Main St

  • What is 63 Main St estimated to be worth?
    Trulia's estimated value for 63 Main St in Windermere, FL is $1,026,700.
  • What is the price history for 63 Main St?
    63 Main St in Windermere, FL last sold for $749,000 in December 2021.
  • 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 63 Main St have air conditioning?
    Yes, 63 Main St in Windermere, FL has air conditioning.
  • Does 63 Main St have laundry facilities?
    Yes, 63 Main St in Windermere, FL has in-unit laundry.