1444 WHITNEY ISLES DRIVE, Windermere, FL 34786
OFF MARKET

$676,400

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,268 sqft

1444 WHITNEY ISLES DRIVE, Windermere, FL 34786

Est. Refi. Payment $4,854/mo*
Refinance Your Home
Currently Off Market - Sold Aug 1, 2025 for $685,000

Home Value

Trulia Estimate
$676K
Since last month
Decreased$8K (-1.2%)
Since last year
Decreased$9K (-1.3%)
Since last sale
Decreased$10K (-1.4%)
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 +60% in the last 10 years
MonthEstimated value
2026
September 2026$675K
August 2026$676K
July 2026$683K
June 2026$687K
May 2026$680K
April 2026$677K
March 2026$669K
February 2026$673K
January 2026$676K
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
1430 GLENWICK DRIVE, Windermere, FL
0.06
Single-Family Home
$720,000
06/24/26
4
3
2,606
1451 WHITNEY ISLES DRIVE, Windermere, FL
0.03
Single-Family Home
$925,000
12/30/25
4
3.5
3,938
1638 WHITNEY ISLES DRIVE, Windermere, FL
0.09
Single-Family Home
$830,000
10/30/25
5
4
3,151
1369 GLENWICK DRIVE, Windermere, FL
0.08
Single-Family Home
$657,000
04/23/26
4
3
2,400
1656 WHITNEY ISLES DRIVE, Windermere, FL
0.11
Single-Family Home
$630,000
11/04/25
3
3
2,433
3213 KENTSHIRE BOULEVARD, Ocoee, FL
0.20
Single-Family Home
$706,000
12/29/25
5
3
3,202
11313 VIA ANDIAMO, Windermere, FL
0.30
Single-Family Home
$595,000
10/28/25
4
3.5
2,727
11234 RAPALLO LANE, Windermere, FL
0.23
Single-Family Home
$512,290
07/01/26
4
2.5
2,236
1412 GLENHEATHER DRIVE, Windermere, FL
0.14
Single-Family Home
$831,000
05/28/26
4
3
2,903
11249 RAPALLO LANE, Windermere, FL
0.27
Single-Family Home
$715,000
08/17/26
5
2.5
2,366

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
1449 GLENWICK DRIVE, Windermere, FL 34786
0.05
$742,500
4
3
2,551
Off Market
1430 GLENWICK DRIVE, Windermere, FL 34786
0.06
$720,000
4
3
2,606
Recently Sold
1448 GLENWICK DRIVE, Windermere, FL 34786
0.08
$696,900
4
3
2,585
Off Market
1451 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.03
$925,000
4
3.5
3,938
Recently Sold
1412 GLENWICK DR, Windermere, FL 34786
0.06
$678,800
3
2
2,074
Off Market
1332 GLENWICK DRIVE, Windermere, FL 34786
0.08
$551,000
3
2
2,065
Off Market
1615 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.06
$799,900
4
4
2,805
Off Market
1375 GLENWICK DRIVE, Windermere, FL 34786
0.07
$710,600
4
3
2,606
Off Market
1369 GLENWICK DRIVE, Windermere, FL 34786
0.08
$657,000
4
3
2,400
Recently Sold
1327 GLENWICK DRIVE, Windermere, FL 34786
0.11
$743,900
4
3
2,184
Off Market
11045 BELMERE ISLES COURT, Windermere, FL 34786
0.13
$648,600
4
3
2,606
Off Market

Local Information

  • Map ViewExplore the area around 1444 WHITNEY ISLES DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2005
3,268 sqft
$207/sqft
2 Car Garage
HOA $136/mo

About this House

FLORIDA living at its finest. Windermere gated community of Whitney Isles?Belmere. This 4 bedroom, 3 full baths and a half bath will give your family a perfect blend of comfort and convenience. The new roof is only 3 years old! Master bedroom is on the first floor with two Walkin closets, a large bathroom with a large walk-in shower and garden tub. Sliding glass door opens to your private patio and backyard. Second bedroom/office is also located on the first floor. It is an en suite design away from the master bedroom. Eating space in the kitchen. Lots of cabinet space and built in oven. Granite counter tops, custom backsplash and a breakfast bar. The family/great room is direct access to the kitchen or outdoor entertaining area. Formal dining room and sitting area located downstairs as well. Upstairs has a large loft with a large closet for storage. Two additional oversized bedrooms are upstairs. King size bed can fit in either room. One with two large closets. Loft area can serve as a game room, home theatre or anything you want. Community has resort style amenities with a gorgeous clubhouse, gigantic community pool, hot tub, tennis courts, basketball court, playground, gym and sauna. Just minutes from Downtown Windermere with is charming cobblestone streets and boutique shops. Easy access to downtown Orlando, Disney World, Orlando Airport. Ideally located closing to shopping, dining, and top-rated schools.
1444 WHITNEY ISLES DRIVE, Windermere, FL 34786 is a 4 bedroom, 4 bathroom, 3,268 sqft single-family home built in 2005. It last sold for $685,000 on Aug 1, 2025 (4% below the $715,000 asking price). More recently, it was listed as a rental in May 2017 with an asking price of $3,500 per month. That rental listing was removed on November 20, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $676,400, with a rent estimate of $3,822/month.
Last check for updates: about 10 hours ago
Listed by Kimberly Cook, (352) 223-2626
ENGEL & VOLKERS CLERMONT, (352) 242-3939
Bought with: Kimberly Cook, (352) 223-2626, ENGEL & VOLKERS CLERMONT, (352) 242-3939
Originating MLS: Lake and Sumter
Source: Stellar MLS, MLS#G5098934
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 1444 WHITNEY ISLES DRIVE

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Dinette, Dining Room, Kitchen, Living Room, Loft
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3268 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sprinkler Meter, Underground Utilities, Water ConnectedAppliances: Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: ElectricHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Electric
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Window TreatmentsDoor: Sliding DoorsFlooring: Carpet, Ceramic Tile, Laminate
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Ceramic Tile, Laminate
View
No View
Security
Security: Gated Community, Security System, Security System Owned

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Rear PorchFencing: FencedVegetation: Mature Landscaping, Oak Trees, Trees/LandscapedExterior: Irrigation System, Lighting, Sidewalk, Sprinkler MeteredFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 25x24No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,Garage Faces Side
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Mediterranean
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional ParcelsIncludes Home Warranty
Property Information
Parcel Number: 312228926000140

Price & Status

Price
List Price: $715,000
Status Change & Dates
Off Market Date: Fri Jun 27 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINDERMERECommunity: WHITNEY ISLES/BELMERE PH 02
School Information
Elementary School: Lake Whitney ElemJr High / Middle School: SunRidge MiddleHigh School: West Orange High

Building

Building Area
Building Area: 4006 Square Feet
Community rooms
Fitness Center

Community

Community Features: Clubhouse, Deed Restrictions, Fitness Center, Gated Community - No Guard, Park, Playground, Pool, Sidewalks, Tennis Court(s)Not Senior Community
Other
Playground

HOA

HOA Fee Includes: Community PoolHOA Name: Sentry Management - Clermont OfficeAssociation for this Listing: Lake and SumterHas an HOAHOA Fee: $136/Monthly

Lot Information

Lot Area: 6597 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: G5098934Showing Considerations: No SignShowing Requirements: Call Listing AgentUniversal Property Id: US-12095-N-312228926000140-R-N

Additional Information

HOA Amenities: Basketball Court,Clubhouse,Fitness Center,Gated,Lobby Key Required,Playground,Pool,Recreation Facilities,Sauna,Spa/Hot Tub,Tennis Court(s)

Price and Tax history

DateEventPrice
Aug 1, 2025
Source: Stellar MLS #G5098934
Sold
$685,000
Jun 28, 2025
Source: Stellar MLS #G5098934
Pending
$715,000
Jun 27, 2025
Source: Stellar MLS #G5098934
Listed For Sale
$715,000
Apr 3, 2020
Source: N/A
Sold
$442,500
Mar 2, 2020
Source: Agent Provided
PriceChange
$449,500
Price decreased by 2%

Market trends in Windermere

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$856K
$41.5KMoM
Sale-to-List Price
96.8%
0.4%MoM
Price per sq ft
$297
$5MoM
Available listings
274
22MoM

Around this home

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
    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 1444 WHITNEY ISLES DRIVE

  • What is 1444 WHITNEY ISLES DRIVE estimated to be worth?
    Trulia's estimated value for 1444 WHITNEY ISLES DRIVE in Windermere, FL is $676,400.
  • What is the price history for 1444 WHITNEY ISLES DRIVE?
    1444 WHITNEY ISLES DRIVE in Windermere, FL last sold for $685,000 in August 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 $856K. That is up $41.5K from the prior month.
  • Does 1444 WHITNEY ISLES DRIVE have air conditioning?
    Yes, 1444 WHITNEY ISLES DRIVE in Windermere, FL has air conditioning.
  • Does 1444 WHITNEY ISLES DRIVE have a pool?
    Yes, 1444 WHITNEY ISLES DRIVE in Windermere, FL has a pool.

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 - Outdoor Space

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