116 MAIN STREET, Windermere, FL 34786
OFF MARKET

116 MAIN STREET
Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,269 sqft (on 0.38 acres)

$687,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $4,807/mo*
Refinance Your Home

$687,800

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $4,807/mo*
Refinance Your Home
3 Beds
2 Baths
1,269 sqft
(on 0.38 acres)

Home Value

Trulia Estimate
$688K
Since last month
Decreased$3K (-0.4%)
Since last year
Decreased$5K (-0.7%)
Since last sale
Decreased$8K (-1.1%)
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 +101% in the last 10 years
MonthEstimated value
2026
August 2026$687K
July 2026$690K
June 2026$693K
May 2026$687K
April 2026$683K
March 2026$676K
February 2026$680K
January 2026$683K
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
0.05
Single-Family Home
$849,000
07/01/26
3
2
2,272
76 OAKDALE STREET, Windermere, FL
0.11
Single-Family Home
$1,060,000
09/11/25
3
1.5
2,011
65 OAKDALE STREET, Windermere, FL
0.16
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
2 OAKDALE STREET, Windermere, FL
0.27
Single-Family Home
$1,160,000
01/09/26
3
2
2,152
305 OAKDALE STREET, Windermere, FL
0.20
Single-Family Home
$710,000
05/19/26
2
1
1,424
415 E 6TH AVENUE, Windermere, FL
0.47
Single-Family Home
$710,000
02/19/26
3
2
1,784
416 MAGNOLIA STREET, Windermere, FL
0.30
Single-Family Home
$820,000
03/06/26
2
1.5
2,115
299 W 4TH AVENUE, Windermere, FL
0.24
Single-Family Home
$862,000
01/08/26
4
3
2,410
825 OAKDALE STREET, Windermere, FL
0.64
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
116 MAIN STREET LOT 434, Windermere, FL 34786
0.00
-
-
-
-
Off Market
111 MAIN STREET, Windermere, FL 34786
0.05
$849,000
3
2
2,272
Recently Sold
133 MAIN STREET, Windermere, FL 34786
0.05
$641,000
3
2
1,166
Off Market
107 E 2ND AVENUE, Windermere, FL 34786
0.06
$1,104,400
4
3
2,684
Off Market
2807 BUTLER BAY DRIVE N, Windermere, FL 34786
0.09
$2,511,600
5
4.5
4,876
Off Market
84 OAKDALE ST, Windermere, FL 34786
0.10
$1,750,000
4
5
3,519
Recently Sold
212 W 1ST AVENUE, Windermere, FL 34786
0.09
$1,650,000
4
2
2,627
For Sale
76 OAKDALE STREET, Windermere, FL 34786
0.11
$1,056,100
3
1.5
2,011
Off Market
81 OAKDALE STREET, Windermere, FL 34786
0.14
$2,200,000
5
4.5
4,284
Recently Sold
226 FOREST STREET, Windermere, FL 34786
0.13
$783,800
3
2
1,532
Off Market
50 FOREST STREET, Windermere, FL 34786
0.15
$7,388,200
6
5.5
7,388
Off Market

Local Information

  • Map ViewExplore the area around 116 MAIN STREET.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1958
Lot Size
0.38 acres
Living Area
1,269 sqft
Price/Sqft
$542
Parking
3 Car Garage
HOA
None

About this House

Welcome to a rare opportunity in the heart of Windermere! Located at 116 Main Street, this property represents one of the most coveted locations in Central Florida's premier community. Situated on Main Street, this lot offers the perfect canvas for your dream home in a location that simply cannot be replicated. While the existing structure requires extensive updating, the true value lies in this premium .38 acre lot. This property sits in the center of historic Windermere, mere steps from the town's charming downtown area, local parks, and the Butler Chain of Lakes. The location offers the perfect blend of small-town charm and luxury living that Windermere is famous for. This an ideal opportunity for buyers looking to build their custom dream home in one of Central Florida's most prestigious addresses. The property's proximity to top-rated Windermere schools, upscale dining and shopping, and easy access to Orlando's attractions adds significant value to this already exceptional location. Just minutes from Restaurant Row, Disney World, and the affluent Isleworth and Bay Hill communities. Whether you're envisioning a modern masterpiece or a traditional estate, this rare Main Street lot provides the perfect foundation for your vision. Properties of this caliber in Windermere's historic downtown rarely become available. Don't miss this opportunity to be a part of Windermere.
116 MAIN STREET, Windermere, FL 34786 is a 3 bedroom, 2 bathroom, 1,269 sqft single-family home built in 1958. It last sold for the $695,000 asking price on Jun 13, 2025. It is currently off market. The Trulia Estimate is $687,800, with a rent estimate of $3,079/month.
Last check for updates: about 5 hours ago
Listed by Adam Judd, (407) 855-5020
METROPOLIS R.E. SOLUTIONS, LLC, (407) 282-1600
Bought with: Jessica Oliveira, (407) 925-9768, LA ROSA REALTY LLC, (321) 939-3748
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6267443
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 116 MAIN STREET

Interior Features

Interior Details
Number of Rooms: 5Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1269 Square Feet
Appliances & Utilities
Utilities: Electricity ConnectedAppliances: OtherLaundry: Other
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Vinyl
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleExterior: OtherFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Garage Attached
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 53

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Condition: FixerParcel Number: 172328933604340

Price & Status

Price
List Price: $695,000
Status Change & Dates
Off Market Date: Tue Apr 01 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: WINDERMERECommunity: WINDERMERE TOWN
School Information
Elementary School: Windermere ElemJr High / Middle School: Gotha MiddleHigh School: Olympia High

Building

Building Area
Building Area: 3567 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.38 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6267443Showing Considerations: See RemarksShowing Requirements: See Remarks, ShowingTimeUniversal Property Id: US-12095-N-172328933604340-R-N

Price and Tax history

DateEventPrice
Jun 13, 2025
Source: Stellar MLS #O6267443
Sold
$695,000
Apr 2, 2025
Source: Stellar MLS #O6267443
Pending
$695,000
Feb 21, 2025
Source: Stellar MLS #O6267443
PendingToActive
$695,000
Feb 21, 2025
Source: Stellar MLS #O6267443
Pending
$695,000
Feb 12, 2025
Source: Stellar MLS #O6267443
Listed For Sale
$695,000

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
    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
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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
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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
    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

Frequently asked questions about 116 MAIN STREET

  • What is 116 MAIN STREET estimated to be worth?
    Trulia's estimated value for 116 MAIN STREET in Windermere, FL is $687,800.
  • What is the price history for 116 MAIN STREET?
    116 MAIN STREET in Windermere, FL last sold for $695,000 in June 2025.
  • 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 116 MAIN STREET have air conditioning?
    Yes, 116 MAIN STREET in Windermere, FL has air conditioning.
  • Does 116 MAIN STREET have laundry facilities?
    Yes, 116 MAIN STREET in Windermere, FL has laundry facilities.

Explore by feature - Pet Friendly

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Apartments for Rent

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Off Market Homes Near 116 MAIN STREET

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Homes for sale near 116 MAIN STREET

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