33 MAIN STREET, Windermere, FL 34786
Property image
Property image
FOR SALE
0.37 ACRES

33 MAIN STREET
Windermere, FL 34786

  • 4 Beds
  • 2 Baths
  • 2,130 sqft (on 0.37 acres)

$1,572,000

Original price: $1,575,000
Est. Mortgage $10,880/mo*
Get Pre-Qualified

$1,572,000

Original price: $1,575,000
Est. Mortgage $10,880/mo*
Get Pre-Qualified
4 Beds
2 Baths
2,130 sqft
(on 0.37 acres)

Home Highlights

Parking
Open Parking
Climate Control
Heating & Cooling
HOA
None
Price/Sqft
$738
Listed
94 days ago

Local Information

  • Map ViewExplore the area around 33 MAIN STREET.
-- mins to
Commute Destination

About this House

BUTLER CHAIN WATERFRONT Windermere 4/3 HOME WITH BOAT SLIP on a .37 acre Lot. Cypress trees line the beautiful serene canal leading directly to the 12 lakes of the Butler Chain. PRIVATE FINANCING IS AVAILABLE - (ask for terms and conditions). Access the Butler chain of lakes from your back yard to Lake Down or Lake Wauseon. Renovate or Build your own modern upscale dream home. Town of Windermere residents can access Fernwood Park and boat ramp 8/10 mile away. Drive your Golf Cart to downtown Windermere. Multiple possibilities for this property in the prime location of Windermere. Home needs major renovation or demolish and rebuild. Sold AS IS.

Home Details for 33 MAIN STREET

Interior Features

Interior Details
Number of Rooms: 4Types of Rooms: Primary Bedroom, Great Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2130 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Public, Water ConnectedAppliances: Dishwasher, Range, RefrigeratorDishwasherLaundry: Electric Dryer Hookup,Inside,Washer HookupRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Living Room, Wood BurningHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Carpet, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Vinyl
View
Has a ViewView: Water, Canal

Exterior Features

Exterior Home Features
Roof: ShingleVegetation: Oak TreesOther Structures: Boat HouseExterior: Boat SlipFoundation: SlabNo Private Pool
Parking & Garage
Number of Carport Spaces: 1Number of Covered Spaces: 1Has a CarportNo GarageHas Open ParkingParking Spaces: 1Parking: Driveway
Frontage
WaterfrontWaterfront: Canal - Freshwater, Canal Front, Freshwater Canal Access, Lake Privileges, Skiing AllowedResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved, AsphaltOn Waterfront
Water & Sewer
Sewer: Septic TankWater Body: BUTLER CHAIN OF LAKES
Farm & Range
Frontage Length: Canal: 90

Days on Market

Cumulative Days on Market: 85Days on Market: 94

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Block, Wood Frame, Wood SidingNot a New ConstructionNo Additional Parcels
Property Information
Condition: FixerParcel Number: 082328194801051

Price & Status

Price
List Price: $1,572,000Price Per Sqft: $738
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: Active

Location

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

Agent Information

Listing Agent
Listing ID: O6406887

Building

Building Area
Building Area: 2470 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.37 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, Owner May Carry

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6406887Water ViewWater View: Water, CanalShowing Requirements: Call Listing Agent, See Remarks, ShowingTimeUniversal Property Id: US-12095-N-082328194801051-R-N
Last check for updates: about 4 hours ago
Listing Provided by: Bruce Higgins, (407) 883-2728
SAND DOLLAR REALTY GROUP INC, (407) 389-7318
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6406887
Also Listed on Stellar MLS.
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

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

Price and Tax history

DateEventPrice
Aug 4, 2026
Source: Stellar MLS #O6406887
PriceChange
$1,572,000
Price decreased by 0%
May 11, 2026
Source: Stellar MLS #O6406887
Listed For Sale
$1,575,000
May 7, 2024
Source: N/A
ListingRemoved
Dec 5, 2023
Source: N/A
Listed For Sale
$1,075,000
Feb 25, 2021
Source: N/A
ListingRemoved

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Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
65 OAKDALE STREET, Windermere, FL
0.11
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
2 OAKDALE STREET, Windermere, FL
0.10
Single-Family Home
$1,160,000
01/09/26
3
2
2,152
76 OAKDALE STREET, Windermere, FL
0.11
Single-Family Home
$1,060,000
09/11/25
3
1.5
2,011
111 MAIN STREET, Windermere, FL
0.17
Single-Family Home
$849,000
07/01/26
3
2
2,272
299 W 4TH AVENUE, Windermere, FL
0.41
Single-Family Home
$862,000
01/08/26
4
3
2,410
416 MAGNOLIA STREET, Windermere, FL
0.44
Single-Family Home
$820,000
03/06/26
2
1.5
2,115
616 MAGNOLIA STREET, Windermere, FL
0.61
Single-Family Home
$830,000
10/27/25
4
2
2,582
84 OAKDALE ST, Windermere, FL
0.12
Single-Family Home
$1,750,000
06/23/26
4
5
3,519
81 OAKDALE STREET, Windermere, FL
0.14
Single-Family Home
$2,200,000
07/31/26
5
4.5
4,284

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
2807 BUTLER BAY DRIVE N, Windermere, FL 34786
0.08
$2,490,000
5
4.5
4,876
Off Market
19 MAIN STREET, Windermere, FL 34786
0.04
$2,792,500
4
3
2,331
Off Market
76 OAKDALE STREET, Windermere, FL 34786
0.11
$1,056,100
3
1.5
2,011
Off Market
57 OAKDALE STREET, Windermere, FL 34786
0.10
$1,219,200
3
2
1,637
Off Market
65 OAKDALE STREET, Windermere, FL 34786
0.11
$1,050,000
4
2
2,191
Recently Sold
84 OAKDALE ST, Windermere, FL 34786
0.12
$1,750,000
4
5
3,519
Recently Sold
2 OAKDALE STREET, Windermere, FL 34786
0.10
$1,160,000
3
2
2,152
Recently Sold
81 OAKDALE STREET, Windermere, FL 34786
0.14
$2,200,000
5
4.5
4,284
Recently Sold
50 FOREST STREET, Windermere, FL 34786
0.14
$7,444,900
6
5.5
7,388
Off Market
116 MAIN STREET, Windermere, FL 34786
0.17
$687,800
3
2
1,269
Off Market
116 MAIN STREET LOT 434, Windermere, FL 34786
0.17
-
-
-
-
Off Market

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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 33 MAIN STREET

  • What is the estimated monthly payment for 33 MAIN STREET?
    Based on a $1,572,000 list price with 20% down at today's rates, the estimated monthly payment for 33 MAIN STREET in Windermere, FL is approximately $11,006 (about $8,141 principal & interest, $2,790 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 33 MAIN STREET compare to homes in Windermere?
    33 MAIN STREET in Windermere, FL is listed at $1,572,000, about 93% above the $814K median sale price in Windermere.
  • What do residents say about Windermere?
    Residents describe Windermere, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Windermere, FL.
  • What are the closest schools to 33 MAIN STREET?
    The closest schools to 33 MAIN STREET in Windermere, FL are Gotha Middle School (rated 6/10), Olympia High School (rated 5/10), Windermere Elementary School (Pre-K, rated 10/10).
  • Does 33 MAIN STREET have air conditioning?
    Yes, 33 MAIN STREET in Windermere, FL has air conditioning.
  • Does 33 MAIN STREET have laundry facilities?
    Yes, 33 MAIN STREET in Windermere, FL has laundry facilities.
Bruce Higgins, SAND DOLLAR REALTY GROUP INC, (407) 389-7318
Agent Phone: (407) 883-2728
33 MAIN STREET, Windermere, FL 34786 is a 4 bedroom, 2 bathroom, 2,130 sqft single-family home built in 1961. This property is currently available for sale and was listed by Stellar MLS on May 11, 2026. The MLS # for this home is MLS# O6406887.