1017 Main St, Windermere, FL 34786
Property image
Property image
OFF MARKET

$766,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,925 sqft (on 0.29 acres)

1017 Main St, Windermere, FL 34786

Est. Refi. Payment $5,308/mo*
Refinance Your Home
Currently Off Market - Sold Nov 21, 2003 for $307,500

Home Value

Trulia Estimate
$766K
Since last month
Increased$700 (+0.1%)
Since last year
Increased$18K (+2.4%)
Since last sale
Increased$456K (+148.2%)
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 +108% in the last 10 years
MonthEstimated value
2026
August 2026$763K
July 2026$762K
June 2026$767K
May 2026$768K
April 2026$761K
March 2026$764K
February 2026$764K
January 2026$750K
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
4 CHASE ROAD, Windermere, FL
0.16
Single-Family Home
$900,000
06/02/26
3
2
2,386
1209 MAIN STREET, Windermere, FL
0.18
Single-Family Home
$925,000
01/05/26
3
2
2,095
825 OAKDALE STREET, Windermere, FL
0.18
Single-Family Home
$770,000
06/11/26
3
2
1,664
1002 OAKDALE STREET, Windermere, FL
0.04
Single-Family Home
$890,000
08/11/26
4
3
3,516
720 MAIN STREET, Windermere, FL
0.24
Single-Family Home
$850,000
10/21/25
3
2
2,778
735 OAKDALE STREET, Windermere, FL
0.24
Single-Family Home
$910,000
05/09/26
3
2.5
2,475
725 OAKDALE STREET, Windermere, FL
0.26
Single-Family Home
$1,000,000
08/28/26
3
2.5
2,795
616 MAGNOLIA STREET, Windermere, FL
0.37
Single-Family Home
$830,000
10/27/25
4
2
2,582
635 BUTLER STREET, Windermere, FL
0.36
Single-Family Home
$975,000
10/20/25
3
3
2,353
416 MAGNOLIA STREET, Windermere, FL
0.54
Single-Family Home
$820,000
03/06/26
2
1.5
2,115

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
1027 MAIN STREET, Windermere, FL 34786
0.02
$725,400
3
2
1,596
Off Market
1020 OAKDALE STREET, Windermere, FL 34786
0.03
$2,171,470
5
4.5
3,994
Recently Sold
1020 OAKDALE STREET LOT 57, Windermere, FL 34786
0.03
-
-
-
-
Off Market
98 E 10TH AVE, Windermere, FL 34786
0.02
$1,824,700
4
3.5
3,650
Off Market
1003 MAIN STREET, Orlando, FL 34786
0.02
$774,000
3
3
2,005
Off Market
1002 OAKDALE STREET, Windermere, FL 34786
0.04
$890,000
4
3
3,516
Recently Sold
1106 OAKDALE STREET, Windermere, FL 34786
0.08
$834,400
3
2
1,965
Off Market
925 MAIN STREET, Windermere, FL 34786
0.09
$1,042,400
5
2.5
2,971
Off Market
1003 OAKDALE STREET, Windermere, FL 34786
0.14
$2,339,600
6
5.5
4,599
Off Market
2 CHASE ROAD LOT 19, Windermere, FL 34786
0.16
$520,000
-
-
-
Recently Sold
4 CHASE ROAD, Windermere, FL 34786
0.16
$900,000
3
2
2,386
Recently Sold
836 OAKDALE STREET, Windermere, FL 34786
0.15
$2,053,200
4
4.5
3,917
Off Market

Local Information

  • Map ViewExplore the area around 1017 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
1988
Lot Size
0.29 acres
Living Area
1,925 sqft
Price/Sqft
$398
Parking
Garage

About this House

Ready for immediate occupancy! Take a look at this great opportunity to rent a one-story pool home in the heart of downtown Windermere situated on 0.3 acre lot. You will immediately notice the beautiful curb appeal with a paver driveway flanked by mature landscaping leading you to a covered porch. The glass front door welcomes you home to a spacious floorplan adorned with travertine floors, 12' ceilings, and planation shutters. The remodeled kitchen is fully equipped with granite countertops, stainless steel appliances, marble backsplash, 42" wood cabinets, closet pantry, and a breakfast bar overlooking the swimming pool. The kitchen opens to the family room and nook with sliding glass doors leading you to a screened in lanai perfect for entertaining guests and soaking up the Florida sun by the pool. Master suite is spacious with access to the heated pool with two walk-in closets, dual vanities, and a glass shower. Secondary bedrooms are generously sized to accommodate loved ones and guests. The fenced backyard is large with beautiful garden and firepit. Garage is a great size with a workshop and utility room. Enjoy the cool lake breezes and the majestic landscapes of Downtown Windermere. The small town is golf cart friendly and has plenty of activities which include a weekly farmers market, monthly food truck event, boat access to The Butler Chain of Lakes & Lake Bessie, tennis courts, and plenty of parks. Don't miss out on this great rental!

Landlord pays for lawn and pool maintenance. No smoking allowed.
1017 Main St, Windermere, FL 34786 is a 3 bedroom, 2 bathroom, 1,925 sqft single-family home built in 1988. It last sold for $307,500 on Nov 21, 2003. More recently, it was listed as a rental in September 2022 with an asking price of $4,000 per month. That rental listing was removed on September 6, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $766,000, with a rent estimate of $3,357/month.

Home Details for 1017 Main St

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherDryerWasher

Exterior Features

Exterior Home Features
Roof: Composition
Pool
Pool
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1988Year Updated: 1988
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Sep 6, 2022
Source: Zillow Rental Manager
ListingRemoved
Sep 2, 2022
Source: Zillow Rental Manager
Listed For Rent
$4,000
Jul 5, 2022
Source: Stellar MLS #O6039317
Pending
$650,000
Nov 21, 2003
Source: N/A
Sold
$307,500
Jul 25, 2001
Source: N/A
Sold
$224,000

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
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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
    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
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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
    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 1017 Main St

  • What is 1017 Main St estimated to be worth?
    Trulia's estimated value for 1017 Main St in Windermere, FL is $766,000.
  • What is the price history for 1017 Main St?
    1017 Main St in Windermere, FL last sold for $307,500 in November 2003.
  • 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 1017 Main St have a pool?
    Yes, 1017 Main St in Windermere, FL has a pool.
  • Does 1017 Main St have laundry facilities?
    Yes, 1017 Main St in Windermere, FL has in-unit laundry.

Explore by feature - Pet Friendly

46 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

84 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

20 rentals with an outdoor space in Windermere, FL

Apartments for Rent

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Off Market Homes Near 1017 Main St

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