1105 Main St, Windermere, FL 34786
Property image
Property image
OFF MARKET

$827,000

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,122 sqft (on 0.37 acres)

1105 Main St, Windermere, FL 34786

Est. Refi. Payment $5,681/mo*
Refinance Your Home
Currently Off Market - Sold May 17, 2021 for $560,000

Home Value

Trulia Estimate
$827K
Since last month
Decreased$2K (-0.2%)
Since last year
Increased$27K (+3.4%)
Since last sale
Increased$265K (+47.4%)
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 +88% in the last 10 years
MonthEstimated value
2026
August 2026$825K
July 2026$827K
June 2026$837K
May 2026$838K
April 2026$828K
March 2026$823K
February 2026$821K
January 2026$802K
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
1209 MAIN STREET, Windermere, FL
0.12
Single-Family Home
$925,000
01/05/26
3
2
2,095
1002 OAKDALE STREET, Windermere, FL
0.09
Single-Family Home
$890,000
08/11/26
4
3
3,516
4 CHASE ROAD, Windermere, FL
0.11
Single-Family Home
$900,000
06/02/26
3
2
2,386
825 OAKDALE STREET, Windermere, FL
0.24
Single-Family Home
$770,000
06/11/26
3
2
1,664
735 OAKDALE STREET, Windermere, FL
0.30
Single-Family Home
$910,000
05/09/26
3
2.5
2,475
616 MAGNOLIA STREET, Windermere, FL
0.43
Single-Family Home
$830,000
10/27/25
4
2
2,582
720 MAIN STREET, Windermere, FL
0.30
Single-Family Home
$850,000
10/21/25
3
2
2,778
635 BUTLER STREET, Windermere, FL
0.41
Single-Family Home
$975,000
10/20/25
3
3
2,353
316 E 5TH AVENUE, Windermere, FL
0.54
Single-Family Home
$1,050,000
05/21/26
4
3
2,412
299 W 4TH AVENUE, Windermere, FL
0.66
Single-Family Home
$862,000
01/08/26
4
3
2,410

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
1106 OAKDALE STREET, Windermere, FL 34786
0.03
$834,400
3
2
1,965
Off Market
1027 MAIN STREET, Windermere, FL 34786
0.04
$725,400
3
2
1,596
Off Market
2 CHASE ROAD LOT 19, Windermere, FL 34786
0.10
$520,000
-
-
-
Recently Sold
4 CHASE ROAD, Windermere, FL 34786
0.11
$900,000
3
2
2,386
Recently Sold
1020 OAKDALE STREET, Windermere, FL 34786
0.07
$2,171,470
5
4.5
3,994
Recently Sold
1020 OAKDALE STREET LOT 57, Windermere, FL 34786
0.07
-
-
-
-
Off Market
1209 MAIN STREET, Windermere, FL 34786
0.12
$925,000
3
2
2,095
Recently Sold
1003 MAIN STREET, Orlando, FL 34786
0.08
$774,000
3
3
2,005
Off Market
98 E 10TH AVE, Windermere, FL 34786
0.08
$1,824,700
4
3.5
3,650
Off Market
1002 OAKDALE STREET, Windermere, FL 34786
0.09
$890,000
4
3
3,516
Recently Sold
925 MAIN STREET, Windermere, FL 34786
0.15
$1,042,400
5
2.5
2,971
Off Market
1003 OAKDALE STREET, Windermere, FL 34786
0.16
$2,339,600
6
5.5
4,599
Off Market

Local Information

  • Map ViewExplore the area around 1105 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
1964
Lot Size
0.37 acres
Living Area
2,122 sqft
Price/Sqft
$390
Parking
Garage

About this House

AWC - Taking Backup Offers To truly appreciate the beauty of this home, you have to see it in person! Located in the tranquil town of Windemere, this home offers a certain charm and characteristic that any buyer will certainly take a liking to. This 4/2.5 home has some amazing features and some pretty remarkable upgrades. The master bathroom, guest bathroom and the closet in the master bedroom have all received major renovations. Also installed was 100% new hardwood flooring throughout the home. Property has a dual septic tanks and a high quality water filtration system in place. Kitchen renovations included all new appliances and natural gas connections to the stove and oven. The addition of an outdoor area including pool, screen enclosure, extended roof, hot tub and summer kitchen with a natural gas connection will definitely change the way you entertain your friends and family. A paved circle driveway in the front of the house welcomes visitors and provides additional parking. Other upgrades include an overhaul of most of the electric wiring in the home, two tankless water heater's for each side of the house and a new air-conditioning unit. A major overhaul of the landscaping, including pathways, a fire pit, hammock and increased drainage capacity. The exterior of the home has also been enhanced with a beautiful stone veneer. Lighting in kitchen has been upgraded with fluorescent and pocket lights. The mud room and half bathroom near the kitchen have also been renovated. Room dimensions need to be independently verified.
1105 Main St, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,122 sqft single-family home built in 1964. It last sold for $560,000 on May 17, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $827,000, with a rent estimate of $4,256/month.

Home Details for 1105 Main St

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
Types of Rooms: Walk In ClosetCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: Built UpDeckExterior: OtherGardenPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1964Year Updated: 1973
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.37 acres

Price and Tax history

DateEventPrice
May 17, 2021
Source: N/A
Sold
$560,000
May 3, 2016
Source: Stellar MLS #O5431580
Sold
$430,000
Apr 16, 2016
Source: Agent Provided
Pending
$450,000
Apr 6, 2016
Source: Agent Provided
Listed For Sale
$450,000
Sep 30, 2003
Source: N/A
Sold
$262,000

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

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
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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
    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
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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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LGBTQ Local Legal Protections

Frequently asked questions about 1105 Main St

  • What is 1105 Main St estimated to be worth?
    Trulia's estimated value for 1105 Main St in Windermere, FL is $827,000.
  • What is the price history for 1105 Main St?
    1105 Main St in Windermere, FL last sold for $560,000 in May 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 1105 Main St have air conditioning?
    Yes, 1105 Main St in Windermere, FL has air conditioning.
  • Does 1105 Main St have a pool?
    Yes, 1105 Main St in Windermere, FL has a pool.

Explore by feature - Pet Friendly

45 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

66 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

84 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

82 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

21 rentals with an outdoor space in Windermere, FL

Apartments for Rent

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Off Market Homes Near 1105 Main St

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Homes for sale near 1105 Main St

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