1656 WHITNEY ISLES DRIVE, Windermere, FL 34786
OFF MARKET

$628,200

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,433 sqft

1656 WHITNEY ISLES DRIVE, Windermere, FL 34786

Est. Refi. Payment $4,510/mo*
Refinance Your Home
Currently Off Market - Sold Nov 4, 2025 for $630,000

Home Value

Trulia Estimate
$628K
Since last month
Decreased$6K (-1%)
Since last year
Decreased$10K (-1.5%)
Since last sale
Decreased$3K (-0.5%)
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 +75% in the last 10 years
MonthEstimated value
2026
August 2026$627K
August 2026$627K
July 2026$633K
June 2026$638K
May 2026$632K
April 2026$627K
March 2026$621K
February 2026$625K
January 2026$626K
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
11234 RAPALLO LANE, Windermere, FL
0.13
Single-Family Home
$512,290
07/01/26
4
2.5
2,236
1369 GLENWICK DRIVE, Windermere, FL
0.16
Single-Family Home
$657,000
04/23/26
4
3
2,400
11316 RAPALLO LANE, Windermere, FL
0.23
Single-Family Home
$570,000
12/03/25
3
2.5
1,925
1430 GLENWICK DRIVE, Windermere, FL
0.16
Single-Family Home
$720,000
06/24/26
4
3
2,606
11249 RAPALLO LANE, Windermere, FL
0.18
Single-Family Home
$715,000
08/17/26
5
2.5
2,366
1028 LASCALA DRIVE, Windermere, FL
0.22
Single-Family Home
$730,000
07/07/26
4
2.5
2,208
1638 WHITNEY ISLES DRIVE, Windermere, FL
0.03
Single-Family Home
$830,000
10/30/25
5
4
3,151
1077 LASCALA DRIVE, Windermere, FL
0.28
Single-Family Home
$660,000
03/03/26
3
2
2,514
272 LONGHIRST LOOP, Ocoee, FL
0.33
Single-Family Home
$485,000
04/06/26
3
2.5
2,056

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
1638 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.03
$827,300
5
4
3,151
Off Market
1706 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.01
$841,900
4
2.5
3,104
Off Market
1712 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.02
$678,000
4
2.5
3,344
Off Market
1615 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.08
$804,300
4
4
2,805
Off Market
1451 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.08
$925,000
4
3.5
3,938
Recently Sold
1361 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.08
$1,100,000
4
4
2,787
For Sale
1444 WHITNEY ISLES DRIVE, Windermere, FL 34786
0.11
$676,400
4
3.5
3,268
Off Market
11222 RAPALLO LANE, Windermere, FL 34786
0.11
$585,500
4
2
2,145
Off Market
11234 RAPALLO LANE, Windermere, FL 34786
0.13
$512,290
4
2.5
2,236
Recently Sold
1449 GLENWICK DRIVE, Windermere, FL 34786
0.15
$746,300
4
3
2,551
Off Market
1375 GLENWICK DRIVE, Windermere, FL 34786
0.15
$716,700
4
3
2,606
Off Market

Local Information

  • Map ViewExplore the area around 1656 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
2,433 sqft
$258/sqft
3 Car Garage
HOA $136/mo

About this House

Tucked inside one of Windermere’s most sought-after gated communities, this beautifully landscaped luxury residence combines refined interior touches with tranquil outdoor living. With every bedroom featuring its own private ensuite, this layout offers both comfort and flexibility—whether you need guest space, office space, or room to stretch out. One of the highlights? The expansive 27-foot primary bedroom, offering a rare amount of space and comfort rarely found in similar homes. From the moment you arrive, you’ll notice the classic curb appeal—brick-paved driveway, barrel tile roof, and a lush landscape framing the welcoming entry. Inside, a bright open-concept layout offers seamless flow from the formal dining area to the casual breakfast nook and spacious living room. Custom drapes, ceramic tile flooring in the main areas, and laminate wood floors in the bedrooms give the home a polished, cohesive feel. The kitchen is a true highlight—appointed with granite countertops, stainless steel appliances, a closet pantry, and a breakfast bar ideal for casual dining. A window over the stove brings in natural light, while a nearby laundry room offers added convenience. Pocketing sliding glass doors lead to a screened-in patio that blends indoor comfort with outdoor charm. Beyond the patio, the fully fenced yard is a private retreat featuring lush greenery, a thoughtfully designed brick-paved path and patio, and a tucked-away fountain surrounded by sculpted shrubs. Whether you're sipping morning coffee, hosting guests, or enjoying some quiet time, this backyard is both functional and picturesque. The downstairs primary suite is generously sized and includes a walk-in closet and a well-designed ensuite bathroom featuring double vanities, a large soaking tub, private water closet and a walk-in shower. A second downstairs bedroom also includes a private ensuite—ideal for guests or multi-generational needs. Upstairs, a massive bonus room offers flexibility as a third bedroom, media room, or office—with its own full bathroom and three closets for ample storage. The home also includes a single-car garage and a separate two-car garage, allowing for multiple vehicles or additional storage. Just a short stroll from your front door, you’ll find the Belmere clubhouse—complete with an events space, a fitness center, tennis courts, basketball court, community pool, and playground. Belmere Village is known for its serene lakes, scenic walking paths, and strong sense of community—all behind secure gated access. Windermere is prized for its peaceful charm and proximity to it all. Belmere offers quick access to major highways, top-rated schools, and world-renowned attractions like Walt Disney World—just 20 minutes away. Local shopping and dining are just around the corner, and the nearby Winter Garden Village and Dr. Phillips areas provide even more options. Zoned for high-performing public schools and near elite private options like Windermere Prep, this location blends convenience with prestige. Additional notable features: 6-year-old A/C, decorative built-ins and soaring ceilings. If you're seeking an elegant home in a premier community with generous space, timeless finishes, and convenient access to the best of Central Florida—this is it.
1656 WHITNEY ISLES DRIVE, Windermere, FL 34786 is a 3 bedroom, 3 bathroom, 2,433 sqft single-family home built in 2005. It last sold for $630,000 on Nov 4, 2025 (5% below the $659,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $628,200, with a rent estimate of $2,909/month.
Last check for updates: about 15 hours ago
Listed by Irena Aistrop, (321) 443-7535
LA ROSA REALTY LLC, (321) 939-3748
Suzanne Aistrop, (321) 443-7257
LA ROSA REALTY LLC, (321) 939-3748
Bought with: Katie Tedesco, (321) 247-8097, COLDWELL BANKER REALTY, (407) 352-1040
Originating MLS: Osceola
Source: Stellar MLS, MLS#S5130375
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 1656 WHITNEY ISLES DRIVE

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dinette, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2433 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Public, Sewer Connected, Street Lights, Water ConnectedAppliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, WasherDishwasherDryerLaundry: Electric Dryer Hookup,Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Window TreatmentsDoor: Sliding DoorsFlooring: Ceramic Tile, Laminate
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Ceramic Tile, Laminate
View
No View
Security
Security: Gated Community, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Rear Porch, ScreenedFencing: FencedVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation System, Lighting, Private Mailbox, SidewalkFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Other Parking: Garage Dimensions: 19x17No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway,Garage Door Opener,Split Garage
Frontage
Road Frontage: Private RoadResponsible for Road Maintenance: Private Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 63

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Other
Building
Construction Materials: Block, StuccoNot a New ConstructionNot Attached PropertyNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Condition: CompletedParcel Number: 282231926000340

Price & Status

Price
List Price: $659,900
Status Change & Dates
Off Market Date: Mon Sep 08 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: 33 Square Feet
Community rooms
Fitness Center

Community

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

HOA

HOA Fee Includes: Community Pool, Private RoadHOA Name: Sentry ManagementAssociation for this Listing: OsceolaHas an HOAHOA Fee: $136/Monthly

Lot Information

Lot Area: 6789 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: S5130375Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-282231926000340-R-N

Additional Information

HOA Amenities: Basketball Court,Clubhouse,Gated,Playground,Pool,Tennis Court(s)

Price and Tax history

DateEventPrice
Nov 4, 2025
Source: Stellar MLS #S5130375
Sold
$630,000
Sep 9, 2025
Source: My State MLS #11531693
Contingent
$659,900
Sep 8, 2025
Source: Stellar MLS #S5130375
Pending
$659,900
Jul 20, 2025
Source: Stellar MLS #S5130375
PriceChange
$659,900
Price decreased by 3%
Jul 7, 2025
Source: Stellar MLS #S5130375
Listed For Sale
$679,900

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

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 1656 WHITNEY ISLES DRIVE

  • What is 1656 WHITNEY ISLES DRIVE estimated to be worth?
    Trulia's estimated value for 1656 WHITNEY ISLES DRIVE in Windermere, FL is $628,200.
  • What is the price history for 1656 WHITNEY ISLES DRIVE?
    1656 WHITNEY ISLES DRIVE in Windermere, FL last sold for $630,000 in November 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 1656 WHITNEY ISLES DRIVE have air conditioning?
    Yes, 1656 WHITNEY ISLES DRIVE in Windermere, FL has air conditioning.
  • Does 1656 WHITNEY ISLES DRIVE have a pool?
    Yes, 1656 WHITNEY ISLES DRIVE in Windermere, FL has a pool.

Explore by feature - Pet Friendly

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