1028 Main St, Windermere, FL 34786
Property image
Property image
OFF MARKET

$2,519,700

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,200 sqft (on 0.56 acres)

1028 Main St, Windermere, FL 34786

Est. Refi. Payment $17,301/mo*
Refinance Your Home
Currently Off Market - Sold Mar 17, 2017 for $1,295,000

Home Value

Trulia Estimate
$2.52M
Since last month
Increased$34K (+1.3%)
Since last year
Increased$187K (+7.9%)
Since last sale
Increased$1M (+96.2%)
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 +98% in the last 10 years
MonthEstimated value
2026
August 2026$2.54M
August 2026$2.52M
July 2026$2.51M
June 2026$2.54M
May 2026$2.51M
April 2026$2.44M
March 2026$2.45M
February 2026$2.43M
January 2026$2.36M
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
109 E 12TH AVENUE, Windermere, FL
0.14
Single-Family Home
$1,150,000
08/28/26
4
3.5
2,791
1002 OAKDALE STREET, Windermere, FL
0.09
Single-Family Home
$890,000
08/11/26
4
3
3,516
735 OAKDALE STREET, Windermere, FL
0.28
Single-Family Home
$910,000
05/09/26
3
2.5
2,475
725 OAKDALE STREET, Windermere, FL
0.29
Single-Family Home
$1,000,000
08/28/26
3
2.5
2,795
1209 MAIN STREET, Windermere, FL
0.18
Single-Family Home
$925,000
01/05/26
3
2
2,095
635 BUTLER STREET, Windermere, FL
0.35
Single-Family Home
$975,000
10/20/25
3
3
2,353
4 CHASE ROAD, Windermere, FL
0.14
Single-Family Home
$900,000
06/02/26
3
2
2,386
316 E 5TH AVENUE, Windermere, FL
0.51
Single-Family Home
$1,050,000
05/21/26
4
3
2,412
720 MAIN STREET, Windermere, FL
0.25
Single-Family Home
$850,000
10/21/25
3
2
2,778
825 OAKDALE STREET, Windermere, FL
0.22
Single-Family Home
$770,000
06/11/26
3
2
1,664

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
1003 MAIN STREET, Orlando, FL 34786
0.06
$774,000
3
3
2,005
Off Market
1027 MAIN STREET, Windermere, FL 34786
0.05
$725,400
3
2
1,596
Off Market
98 E 10TH AVE, Windermere, FL 34786
0.07
$1,824,700
4
3.5
3,650
Off Market
1020 OAKDALE STREET, Windermere, FL 34786
0.09
$2,171,470
5
4.5
3,994
Recently Sold
1020 OAKDALE STREET LOT 57, Windermere, FL 34786
0.09
-
-
-
-
Off Market
1002 OAKDALE STREET, Windermere, FL 34786
0.09
$890,000
4
3
3,516
Recently Sold
925 MAIN STREET, Windermere, FL 34786
0.11
$1,042,400
5
2.5
2,971
Off Market
1106 OAKDALE STREET, Windermere, FL 34786
0.10
$834,400
3
2
1,965
Off Market
904 MAIN STREET, Windermere, FL 34786
0.14
$3,592,800
4
5
6,079
Off Market
109 E 12TH AVENUE, Windermere, FL 34786
0.14
$1,150,000
4
3.5
2,791
Recently Sold
2 CHASE ROAD LOT 19, Windermere, FL 34786
0.14
$520,000
-
-
-
Recently Sold
4 CHASE ROAD, Windermere, FL 34786
0.14
$900,000
3
2
2,386
Recently Sold

Local Information

  • Map ViewExplore the area around 1028 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
1942
Lot Size
0.56 acres
Living Area
2,200 sqft
Price/Sqft
$1,145
Parking
Garage

About this House

LOCATION, LOCATION, LOCATION. One of the best lots on the entire Butler Chain of Lakes in much sought-after Downntown Windermere. Small town charm, big city convenience, and a water lover's paradise Great Golf Courses nearby this property-minutes away. 4 Bedrooms, 3 Baths w/Guest House (3 Bdrms, 2 Baths Main House). Private Boat Dock with electric lift and large screened in sitting area. Private Boat Ramp - on property ! (When you have your own boat ramp you don't wait in line. Detached Guest House/Tiny House with full bath, shower, air-conditioning, hardwood floors, loft, high-end convection microwave, refrigerator, granite counter tops, ceiling fan, paver patio facing lake - beautifully remodeled ! Fireplace - Brick, Wood Burning w/gas (Living room of main house). Hardwood Floors (real and beautiful hardwood). Large Multi-Level Rear Deck facing Lake Butler and Bird Island. Amazing Views of beautiful Lake Butler evening sunsets. 1,840 sq ft. Main House and 318 sq. ft. Guest House/Tiny House. Main House Remodeled 2016. Guest House Remodeled 2014. Dishwasher, Refrigerator, Range/Oven. Custom Window Blinds. Water for watering lawn and landscaping comes from lake--NOT charged to tenants water bill. Located in historic and quaint downtown Windermere - Life is Good! Boating, Skiing and Fishing. Florida Lakefront Living and Lifestyle at it's BEST.
1028 Main St, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,200 sqft single-family home built in 1942. It last sold for $1,295,000 on Mar 17, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,519,700, with a rent estimate of $4,658/month.

Home Details for 1028 Main St

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: WoodPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 10Parking: Garage Attached

Property Information

Year Built
Year Built: 1942Year Updated: 1962
Property Type / Style
Property Type: Single Family HomeArchitecture: Bungalow

Community

Units in Building: 1

Lot Information

Lot Area: 0.56 acres

Price and Tax history

DateEventPrice
Mar 17, 2017
Source: N/A
Sold
$1,295,000
Jun 9, 2003
Source: N/A
Sold
$875,000

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
    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
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LGBTQ Local Legal Protections

Frequently asked questions about 1028 Main St

  • What is 1028 Main St estimated to be worth?
    Trulia's estimated value for 1028 Main St in Windermere, FL is $2,519,700.
  • What is the price history for 1028 Main St?
    1028 Main St in Windermere, FL last sold for $1,295,000 in March 2017.
  • 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 1028 Main St have air conditioning?
    Yes, 1028 Main St in Windermere, FL has air conditioning.
  • How big is the lot at 1028 Main St?
    The lot at 1028 Main St in Windermere, FL is about 0.56 acres (24,297 sq ft).

Explore by feature - Pet Friendly

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Apartments for Rent

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Off Market Homes Near 1028 Main St

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