19 MAIN STREET, Windermere, FL 34786
OFF MARKET

19 MAIN STREET
Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,331 sqft (on 0.40 acres)

$2,792,500

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $19,197/mo*
Refinance Your Home

$2,792,500

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $19,197/mo*
Refinance Your Home
4 Beds
3 Baths
2,331 sqft
(on 0.40 acres)

Home Value

Trulia Estimate
$2.79M
Since last month
Decreased$7K (-0.3%)
Since last year
Increased$2M (+145.4%)
Since last sale
Increased$2M (+142.8%)
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 +513% in the last 10 years
MonthEstimated value
2026
August 2026$2.79M
July 2026$2.8M
June 2026$2.8M
May 2026$2.85M
April 2026$2.86M
March 2026$2.86M
February 2026$2.93M
January 2026$1.12M
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
2 OAKDALE STREET, Windermere, FL
0.06
Single-Family Home
$1,160,000
01/09/26
3
2
2,152
65 OAKDALE STREET, Windermere, FL
0.14
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
76 OAKDALE STREET, Windermere, FL
0.14
Single-Family Home
$1,060,000
09/11/25
3
1.5
2,011
111 MAIN STREET, Windermere, FL
0.21
Single-Family Home
$849,000
07/01/26
3
2
2,272
299 W 4TH AVENUE, Windermere, FL
0.44
Single-Family Home
$862,000
01/08/26
4
3
2,410
316 E 5TH AVENUE, Windermere, FL
0.56
Single-Family Home
$1,050,000
05/21/26
4
3
2,412
412 FOREST STREET, Windermere, FL
0.48
Single-Family Home
$765,000
07/30/26
5
2.5
2,539
106 PALM STREET, Windermere, FL
0.34
Single-Family Home
$1,375,000
06/11/26
5
4.5
3,082
84 OAKDALE ST, Windermere, FL
0.16
Single-Family Home
$1,750,000
06/23/26
4
5
3,519

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
33 MAIN STREET, Windermere, FL 34786
0.04
$1,572,000
4
2
2,130
For Sale
2 OAKDALE STREET, Windermere, FL 34786
0.06
$1,160,000
3
2
2,152
Recently Sold
57 OAKDALE STREET, Windermere, FL 34786
0.12
$1,219,200
3
2
1,637
Off Market
2807 BUTLER BAY DRIVE N, Windermere, FL 34786
0.12
$2,490,000
5
4.5
4,876
Off Market
65 OAKDALE STREET, Windermere, FL 34786
0.14
$1,050,000
4
2
2,191
Recently Sold
76 OAKDALE STREET, Windermere, FL 34786
0.14
$1,056,100
3
1.5
2,011
Off Market
84 OAKDALE ST, Windermere, FL 34786
0.16
$1,750,000
4
5
3,519
Recently Sold
50 FOREST STREET, Windermere, FL 34786
0.15
$7,388,200
6
5.5
7,388
Off Market
81 OAKDALE STREET, Windermere, FL 34786
0.17
$2,200,000
5
4.5
4,284
Recently Sold
7 1ST COURT, Windermere, FL 34786
0.18
$2,802,600
4
3
3,149
Off Market
111 MAIN STREET, Windermere, FL 34786
0.21
$849,000
3
2
2,272
Recently Sold

Local Information

  • Map ViewExplore the area around 19 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
1959
Lot Size
0.4 acres
Living Area
2,331 sqft
Price/Sqft
$1,198
Parking
2 Car Garage
HOA
None

About this House

BACK ON THE MARKET DUE TO BUYER PERFORMANCE! Priced below recent appraisal! Welcome to waterfront luxury living at its finest in the heart of Windermere, nestled along the serene Butler Chain of Lakes. This impeccably renovated 4-bedroom, 3-bathroom home offers 100 feet of direct Fischer canal frontage, and is located between Lake Down and Wauseon Bay, providing a picturesque backdrop for your daily adventures. Step inside to discover a haven of modern elegance, where every detail has been thoughtfully crafted to create a harmonious blend of style and comfort. The open floor plan invites you to explore, with luxurious LVP flooring, foam insulated exterior walls and ceilings, and energy-efficient windows enhancing the ambiance throughout. Indulge your inner chef in the gourmet kitchen, where marble counters and an 11-foot waterfall island set the stage for culinary mastery. High-end appliances, including a Wolfe gas range and dual Kitchen Aid Wall ovens/microwave convection oven, cater to your every culinary desire, while custom cabinets offer ample storage space for all your kitchen essentials. Retreat to one of the dual master suites, each offering tranquil water views and lavish en suite bathrooms. The primary owner suite exudes luxury with backlit LED dual vanity, dual sinks, marble floors, and a marble shower, creating a spa-like sanctuary for relaxation. Outside, a sprawling covered lanai spans the width of the home, providing the perfect setting for outdoor entertaining or simply enjoying the gentle breezes off the water. A large composite deck beckons for gatherings with loved ones, while two floating docks and a new seawall offer easy access to the pristine waters of the Butler Chain of Lakes. Additional features include a whole-home standby generator with automatic transfer switch and direct line natural gas, ensuring peace of mind during any power outage, and a fenced-in backyard for added privacy and security. Located in the charming, golf cart-friendly Town of Windermere, residents enjoy access to a vibrant town center boasting boutique shops, cafes, coffee shops, a weekly farmers market, food truck Fridays, and special family-oriented events. Don't miss your chance to experience the ultimate in waterfront living. Schedule your private showing today and discover the luxury lifestyle that awaits you in this exquisite Windermere waterfront home.
19 MAIN STREET, Windermere, FL 34786 is a 4 bedroom, 3 bathroom, 2,331 sqft single-family home built in 1959. It last sold for $1,150,000 on Feb 5, 2025 (11% below the $1,295,000 asking price). It is currently off market. The Trulia Estimate is $2,792,500, with a rent estimate of $4,364/month.

Home Details for 19 MAIN STREET

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Primary Bedroom, Primary Bedroom 2, Bedroom 3, Bedroom 4, Great Room, KitchenWet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2331 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Public, Water ConnectedAppliances: Oven, Convection Oven, Dishwasher, Disposal, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Wine RefrigeratorDishwasherDisposalLaundry: Gas Dryer Hookup,Inside,Laundry Room,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Central,Electric,Exhaust Fan,Heat Pump,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: ElectricHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Insulated Windows, Window TreatmentsDoor: Sliding DoorsFlooring: Luxury Vinyl, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Luxury Vinyl, Tile
View
Has a ViewView: Water, Canal, Lake

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Rear PorchFencing: FencedVegetation: Mature LandscapingExterior: Irrigation SystemFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener
Frontage
WaterfrontWaterfront: Canal - Freshwater, Freshwater Canal Access, Lake Privileges, No Wake Zone, Seawall, Skiing AllowedResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Septic TankWater Body: BUTLER CHAIN OF LAKES

Days on Market

Cumulative Days on Market: 146

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, Cement SidingNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 082328194801070

Price & Status

Price
List Price: $1,295,000
Status Change & Dates
Off Market Date: Mon Dec 09 2024

Active Status

MLS Status: Sold

Media

Location

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

Building

Building Area
Building Area: 3275 Square Feet

Community

Community Features: Golf Carts OKNot Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.40 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6209334Water ViewWater View: Water, Canal, LakeShowing Advance Notice: 24Showing AttendedShowing Considerations: See RemarksShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, See Remarks, ShowingTimeUniversal Property Id: US-12095-N-082328194801070-R-N

Additional Information

Golf Carts OK
Last check for updates: about 17 hours ago
Listed by Corey Mathias, (407) 730-1318
LAKESIDE REALTY WINDERMERE INC, (407) 876-5575
Anna McIntyre, (407) 353-7138
LAKESIDE REALTY WINDERMERE INC, (407) 876-5575
Bought with: Silvana Camner, (321) 228-2925, LPT REALTY, LLC, (877) 366-2213
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6209334
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

Price and Tax history

DateEventPrice
Jun 10, 2026
Source: Stellar MLS #O6383837
ListingRemoved
$3,000,000
Feb 19, 2026
Source: Stellar MLS #O6383837
Listed For Sale
$3,000,000
Feb 5, 2025
Source: Stellar MLS #O6209334
Sold
$1,150,000
Dec 9, 2024
Source: Stellar MLS #O6209334
Pending
$1,295,000
Sep 30, 2024
Source: Stellar MLS #O6209334
PriceChange
$1,295,000
Price decreased by 4%

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
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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
    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
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  • 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
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  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
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  • 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
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  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
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  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
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  • 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."
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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
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  • 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
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  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

47 pet-friendly rentals in Windermere, FL

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Homes for sale near 19 MAIN STREET

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Off Market Homes Near 19 MAIN STREET

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Frequently asked questions about 19 MAIN STREET

  • What is 19 MAIN STREET estimated to be worth?
    Trulia's estimated value for 19 MAIN STREET in Windermere, FL is $2,792,500.
  • What is the price history for 19 MAIN STREET?
    19 MAIN STREET in Windermere, FL last sold for $1,150,000 in February 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 19 MAIN STREET have air conditioning?
    Yes, 19 MAIN STREET in Windermere, FL has air conditioning.
  • Does 19 MAIN STREET have laundry facilities?
    Yes, 19 MAIN STREET in Windermere, FL has laundry facilities.