1433 Whitney Isles Dr, Windermere, FL 34786
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OFF MARKET

1433 Whitney Isles Dr
Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,402 sqft

$829,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $5,700/mo*
Refinance Your Home

$829,100

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $5,700/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,402 sqft

Local Information

  • Map ViewExplore the area around 1433 Whitney Isles Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Back to market, buyer financing fell through - Further price drop, motivated seller. This fantastic pool home has just had a full make over - full exterior paint including 2 garage blocks, interior has new paint and carpets throughout so ready for new owners with nothing to do but move in. The home benefits from wood flooring in the formal living and dining areas with great structural detail throughout the home consistent with ABD construction including wall niche details in the dining area and living areas and built in alcoves and shelving in the family room. The master suite is huge and bathroom has large soaking tub and huge walk in shower. upstairs has an additional 3 large bedrooms and huge loft area. The pool deck has been repainted giving the home an almost new feel and pool benefits from a spa and fountain detail. Whitney Isles is a small gated community of a single Cul de sac - community features include heated pool, tennis, volleyball, basketball court, fitness center and community hall. Located close to all major highways and downtown Windermere.
1433 Whitney Isles Dr, Windermere, FL 34786 is a 4 bedroom, 4 bathroom, 3,402 sqft single-family home built in 2005. It last sold for $425,000 on Jul 17, 2020. More recently, it was listed as a rental in August 2019 with an asking price of $3,200 per month. That rental listing was removed on October 17, 2019. It is currently off market. The Trulia Estimate is $829,100, with a rent estimate of $3,795/month.

Home Highlights

Parking
Garage
Outdoor
Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 1433 Whitney Isles Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: Tile
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2005Year Updated: 2005
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 9038 sqft

Price History for 1433 Whitney Isles Dr

DatePriceEventSource
11/13/2025$815,000ListingRemovedStellar MLS #O6331550
10/08/2025$815,000PriceChange
Stellar MLS #O6331550
09/03/2025$815,990PriceChange
Stellar MLS #O6331550
08/11/2025$819,990PriceChange
Stellar MLS #O6331550
07/30/2025$839,990Listed For SaleStellar MLS #O6331550
07/17/2020$425,000Sold
N/A
06/05/2020$449,000PendingAgent Provided
05/01/2020$449,000PriceChange
Agent Provided
03/29/2020$459,000PriceChange
Agent Provided
03/05/2020$469,000PendingAgent Provided
03/03/2020$469,000PriceChange
Agent Provided
01/27/2020$479,000PriceChange
Agent Provided
01/11/2020$489,000PriceChange
Agent Provided
12/04/2019$499,000Listed For SaleAgent Provided
10/17/2019$3,200ListingRemovedN/A
08/22/2019$3,200Listed For RentN/A
03/13/2015$3,000ListingRemovedN/A
03/10/2015$3,000PriceChange
N/A
02/23/2015$2,800Listed For RentN/A
01/07/2010$435,000ListingRemovedAgent Provided
12/20/2009$435,000PriceChange
Agent Provided
12/10/2009$460,000PriceChange
Agent Provided
09/27/2009$499,000Listed For SaleAgent Provided
11/01/2005$444,000Sold
N/A

Market trends in Windermere

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$672K
$26.67KMoM
Sale-to-List Price
97.5%
0.3%MoM
Price per sq ft
$262
$6MoM
Available listings
291
2MoM
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Property Tax and Assessment

Year2024
Tax$7,294
Assessment$666,348
Home facts updated by county records

Comparable Sales for 1433 Whitney Isles Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1444 Whitney Isles Dr, Windermere, FL
0.04
Single-Family Home
$685,000
08/01/25
4
3.5
3,268
1451 Whitney Isles Dr, Windermere, FL
0.03
Single-Family Home
$925,000
12/30/25
4
3.5
3,938
1369 Glenwick Dr, Windermere, FL
0.10
Single-Family Home
$657,000
04/23/26
4
3
2,400
1430 Glenwick Dr, Windermere, FL
0.10
Single-Family Home
$720,000
06/24/26
4
3
2,606
1638 Whitney Isles Dr, Windermere, FL
0.06
Single-Family Home
$830,000
10/30/25
5
4
3,151
1656 Whitney Isles Dr, Windermere, FL
0.07
Single-Family Home
$630,000
11/04/25
3
3
2,433
11234 Rapallo Ln, Windermere, FL
0.19
Single-Family Home
$512,290
07/01/26
4
2.5
2,236
3213 Kentshire Blvd, Ocoee, FL
0.23
Single-Family Home
$706,000
12/29/25
5
3
3,202
1220 Glenheather Dr, Windermere, FL
0.15
Single-Family Home
$704,000
09/18/25
4
3
2,695
3307 Kentshire Blvd, Ocoee, FL
0.29
Single-Family Home
$675,000
07/22/25
4
3
2,827

Nearby homes

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Assigned Schools

These are the assigned schools for 1433 Whitney Isles Dr.
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 270 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

  • 79 % 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
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  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
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  • 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
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  • 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
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  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
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  • 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
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  • 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
    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
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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
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Apartments for Rent

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Explore by feature - Pet Friendly

41 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

69 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

75 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

72 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

82 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

18 rentals with an outdoor space in Windermere, FL

Homes for sale near 1433 Whitney Isles Dr

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Off Market Homes Near 1433 Whitney Isles Dr

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