106 Main St, Windermere, FL 34786
Kitchen
Master Bath
OFF MARKET

$738,200

Trulia Estimate
as of Aug 27, 2026
  • 3 Beds
  • 2 Baths
  • 2,000 sqft
  • 3 Beds
  • 2 Baths
  • 2,000 sqft

106 Main St, Windermere, FL 34786

Home Highlights

Property Type
Single-Family Home
Living Area
2,000 sqft
Price/Sqft
$369
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 106 Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Welcome home! This beautiful 3-bedroom, 2-bath residence is nestled in the heart of downtown Windermere, offering the perfect blend of comfort and convenience right at your doorstep. Enjoy the vibrant community with easy access to the local farmer's market, scenic trails, brewery, and a variety of shops and restaurants- all just a quick walk or golf cart ride away. Plus, you're just a short drive from Orlando's top attractions and theme parks.

With a newly renovated master bathroom, fresh paint throughout the home, new LVP flooring, and a brand-new A/C system, this home is move-in ready!

Whether you're entertaining friends or relaxing with family, this home is the ideal place to create lasting memories. Don't miss your chance to make it yours!

Other features include: Water softening system, Well water and Septic (No monthly water or sewer bills). No HOA.

This is a no smoking residence.
Minimum financial requirement to move in is first month's rent and one month security deposit.
All applications are processed through Zillow.
106 Main St, Windermere, FL 34786 is a 3 bedroom, 2 bathroom, 2,000 sqft single-family home. More recently, it was listed as a rental in September 2024 with an asking price of $3,750 per month. That rental listing was removed on October 1, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $738,200, with a rent estimate of $3,721/month.

Home Details for 106 Main St

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 106 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
111 MAIN STREET, Windermere, FL
0.06
Single-Family Home
$849,000
07/01/26
3
2
2,272 sqft
76 OAKDALE STREET, Windermere, FL
0.10
Single-Family Home
$1,060,000
09/11/25
3
1.5
2,011 sqft
65 OAKDALE STREET, Windermere, FL
0.15
Single-Family Home
$1,050,000
10/31/25
4
2
2,191 sqft
11 Main St, Windermere, FL
0.21
Single-Family Home
$1,200,000
09/15/25
3
2
1,638 sqft
2 OAKDALE STREET, Windermere, FL
0.25
Single-Family Home
$1,160,000
01/09/26
3
2
2,152 sqft
416 MAGNOLIA STREET, Windermere, FL
0.32
Single-Family Home
$820,000
03/06/26
2
1.5
2,115 sqft
299 W 4TH AVENUE, Windermere, FL
0.26
Single-Family Home
$862,000
01/08/26
4
3
2,410 sqft
414 E 5TH AVENUE, Windermere, FL
0.46
Single-Family Home
$1,050,000
05/14/26
3
2
2,521 sqft
412 FOREST STREET, Windermere, FL
0.29
Single-Family Home
$765,000
07/30/26
5
2.5
2,539 sqft
616 MAGNOLIA STREET, Windermere, FL
0.48
Single-Family Home
$830,000
10/27/25
4
2
2,582 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
    Flag
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Oct 1, 2024
Source: Zillow Rentals
ListingRemoved
$3,475
Sep 29, 2024
Source: Zillow Rentals
PriceChange
$3,475
Price decreased by 7%
Sep 22, 2024
Source: Zillow Rentals
Listed For Rent
$3,750
Jul 10, 2023
Source: N/A
ListingRemoved
Jun 9, 2023
Source: N/A
Pending
$1,330,000

Frequently asked questions about 106 Main St

  • What is 106 Main St estimated to be worth?
    Trulia's estimated value for 106 Main St in Windermere, FL is $738,200.
  • 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.
  • What do residents say about Windermere?
    Residents describe Windermere, FL as dog-friendly, pedestrian-friendly, and easy to park in. See recently sold homes in Windermere, FL.
  • Does 106 Main St have air conditioning?
    Yes, 106 Main St in Windermere, FL has air conditioning.
  • Does 106 Main St have laundry facilities?
    Yes, 106 Main St in Windermere, FL has in-unit laundry.

Homes for rent near 106 Main St

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item