133 MAIN STREET, Windermere, FL 34786
OFF MARKET

$641,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,166 sqft (on 0.33 acres)

133 MAIN STREET, Windermere, FL 34786

Est. Refi. Payment $4,502/mo*
Refinance Your Home
Currently Off Market - Sold Oct 31, 2024 for $550,000

Home Value

Trulia Estimate
$641K
Since last month
Increased$7K (+1.1%)
Since last year
Increased$99K (+18.2%)
Since last sale
Increased$90K (+16.4%)
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 +150% in the last 10 years
MonthEstimated value
2026
August 2026$640K
August 2026$640K
July 2026$633K
June 2026$605K
May 2026$572K
April 2026$533K
March 2026$527K
February 2026$532K
January 2026$532K
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
0.02
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
305 OAKDALE STREET, Windermere, FL
0.15
Single-Family Home
$710,000
05/19/26
2
1
1,424
65 OAKDALE STREET, Windermere, FL
0.15
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
416 MAGNOLIA STREET, Windermere, FL
0.25
Single-Family Home
$820,000
03/06/26
2
1.5
2,115
2 OAKDALE STREET, Windermere, FL
0.29
Single-Family Home
$1,160,000
01/09/26
3
2
2,152
299 W 4TH AVENUE, Windermere, FL
0.23
Single-Family Home
$862,000
01/08/26
4
3
2,410
825 OAKDALE STREET, Windermere, FL
0.60
Single-Family Home
$770,000
06/11/26
3
2
1,664
616 MAGNOLIA STREET, Windermere, FL
0.42
Single-Family Home
$830,000
10/27/25
4
2
2,582

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
111 MAIN STREET, Windermere, FL 34786
0.02
$849,000
3
2
2,272
Recently Sold
107 E 2ND AVENUE, Windermere, FL 34786
0.02
$1,100,200
4
3
2,684
Off Market
116 MAIN STREET, Windermere, FL 34786
0.05
$685,600
3
2
1,269
Off Market
116 MAIN STREET LOT 434, Windermere, FL 34786
0.05
-
-
-
-
Off Market
84 OAKDALE ST, Windermere, FL 34786
0.09
$1,750,000
4
5
3,519
Recently Sold
76 OAKDALE STREET, Windermere, FL 34786
0.11
$1,052,600
3
1.5
2,011
Off Market
81 OAKDALE STREET, Windermere, FL 34786
0.12
$2,200,000
5
4.5
4,284
Recently Sold
2807 BUTLER BAY DRIVE N, Windermere, FL 34786
0.12
$2,487,600
5
4.5
4,876
Off Market
216 MAGNOLIA STREET, Windermere, FL 34786
0.12
$1,492,900
4
4.5
3,787
Off Market
65 OAKDALE STREET, Windermere, FL 34786
0.15
$1,046,700
4
2
2,191
Off Market
235 OAKDALE STREET, Windermere, FL 34786
0.12
$881,000
3
2
2,562
Off Market

Local Information

  • Map ViewExplore the area around 133 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
1963
Lot Size
0.33 acres
Living Area
1,166 sqft
Price/Sqft
$550
Parking
2 Carport Spaces
HOA
None

About this House

**Price improvement! Sellers motivated!** Now is your chance to live the true Windermere lifestyle, "Among the Lakes"! Make this charming 3/2 home your haven for all that the Town Windermere has to offer. No HOA restrictions, well maintained, and move-in ready, this home sits on an impressive 95 ft X 150 ft corner lot in the very heart of the Town of Windermere. Located just a few blocks from the quaint Town square, weekly farmers markets, shops, eateries, brewery, coffee shop, wine shop, monthly food truck nights, resident-only special events, public library, churches, and so much more. Enjoy boating on the famous Butler Chain of Lakes and Lake Bessie through exclusive, deeded boat ramp access, relax and watch the sunset from one of numerous parks and playgrounds, or swim and fish from one of several town docks! Home features original hardwood flooring throughout the living spaces and bedrooms, with ceramic tile in the kitchen and bathrooms. Roof and A/C replaced in 2018, septic in 2019, electric upgraded in 2021 (see attachments for full list of upgrades). Other features include attached carport (pre-wired for EV wall connector port) and separate laundry room/workshop space with plenty of extra storage space. This is a RARE opportunity to make your Windermere dream come true! With A-rated schools and plenty of outdoor activities available, this unique, golf-cart friendly community make this home a must-see. Don't miss out on your chance to live "Among the Lakes”!
133 MAIN STREET, Windermere, FL 34786 is a 3 bedroom, 2 bathroom, 1,166 sqft single-family home built in 1963. It last sold for $550,000 on Oct 31, 2024 (8% below the $599,000 asking price). More recently, it was listed as a rental in October 2020 with an asking price of $1,995 per month. That rental listing was removed on December 16, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $641,000, with a rent estimate of $3,163/month.
Last check for updates: about 1 hour ago
Listed by Bill Martini, (407) 493-3505
BHHS FLORIDA REALTY, (407) 876-2090
Bought with: Tatiana Shiz Nagamine de Almeida, (407) 520-6701, TALENT REALTY SOLUTIONS, (407) 910-2020
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6216299
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 133 MAIN STREET

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bathroom 3, Dining Room, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1166 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Natural Gas Available, Public, Water AvailableAppliances: Dishwasher, Dryer, Electric Water Heater, Range, Refrigerator, WasherDishwasherDryerLaundry: In GarageRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Ceramic Tile, Hardwood
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleVegetation: Oak Trees, Trees/LandscapedExterior: OtherFoundation: CrawlspaceNo Private Pool
Parking & Garage
Number of Carport Spaces: 2Number of Covered Spaces: 2Has a CarportNo GarageNo Attached GarageParking Spaces: 2Parking: Carport
Frontage
Waterfront: Lake, Lake PrivilegesResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Asphalt, PavedNot on Waterfront
Water & Sewer
Sewer: Septic TankWater Body: BUTLER CHAIN OF LAKES

Days on Market

Cumulative Days on Market: 102

Property Information

Year Built
Year Built: 1963
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 172328933604410

Price & Status

Price
List Price: $599,000
Status Change & Dates
Off Market Date: Mon Sep 30 2024

Active Status

MLS Status: Sold

Media

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: 1684 Square Feet

Community

Community Features: Community Boat Ramp, Dock, Fishing, Lake, Water AccessNot Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.33 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6216299Showing Considerations: See RemarksShowing Requirements: Appointment Only, Lockbox - Coded, ShowingTimeUniversal Property Id: US-12095-N-172328933604410-R-N

Additional Information

Community Boat RampDockFishingLakeWater Access

Price and Tax history

DateEventPrice
Oct 31, 2024
Source: Stellar MLS #O6216299
Sold
$550,000
Oct 1, 2024
Source: Stellar MLS #O6216299
Pending
$599,000
Sep 14, 2024
Source: Stellar MLS #O6216299
PriceChange
$599,000
Price decreased by 5%
Jun 20, 2024
Source: Stellar MLS #O6216299
Listed For Sale
$629,000
Dec 16, 2020
Source: Agent Provided
ListingRemoved
$1,795

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
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  • 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
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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
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  • 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
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  • 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 133 MAIN STREET

  • What is 133 MAIN STREET estimated to be worth?
    Trulia's estimated value for 133 MAIN STREET in Windermere, FL is $641,000.
  • What is the price history for 133 MAIN STREET?
    133 MAIN STREET in Windermere, FL last sold for $550,000 in October 2024.
  • 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 133 MAIN STREET have air conditioning?
    Yes, 133 MAIN STREET in Windermere, FL has air conditioning.
  • Does 133 MAIN STREET have laundry facilities?
    Yes, 133 MAIN STREET in Windermere, FL has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

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Off Market Homes Near 133 MAIN STREET

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