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$3,290,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 2 Partial Baths
  • 5,502 Sq. Ft.
  • Updated 1 day ago
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Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers residence offers approximately 5,502 square feet of beautifully appointed living space, featuring 5 private ensuite bedrooms and 2 half bathrooms. From the moment you enter, the home impresses with sophisticated architectural details, soaring ceilings, abundant natural light, and expansive spaces thoughtfully designed for both refined everyday living and effortless entertaining. The gourmet kitchen is equipped with premium appliances, custom cabinetry, an oversized island, ample counter space, and an open-concept design that flows seamlessly into the family room and dining areas. The first-floor primary suite offers a tranquil private retreat, complete with a spa-inspired bathroom featuring dual vanities, a spacious walk-in shower, and generous his-and-her closet areas. Also located on the first floor is an additional private suite and a dedicated office, while the second floor offers the remaining bedrooms, a secondary primary suite, a spacious loft, and versatile living areas. Step outside to an impressive outdoor living space featuring a private heated in-ground pool, upgraded covered lanai with a summer kitchen, and beautifully landscaped surroundings, creating an ideal setting for entertaining or relaxing in complete privacy. Additional features include a three-car garage, tile roof, elegant finishes, abundant storage, and carefully curated furnishings throughout. Offered fully furnished, this exceptional residence presents a rare opportunity to enjoy a turnkey Windermere lifestyle within one of Central Florida's sought-after gated communities. Ideally positioned near premier shopping, fine dining, golf, entertainment, major roadways, and world-renowned attractions, this Casabella estate brings together luxury, privacy, comfort, and convenience.

Full Property Details for 4243 Isabella Cir

General

  • Price: $3,290,000
  • HOA FEE: $537/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $35,130 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6439995
  • Updated: 9/9/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Solid Surface Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
  • Furnishings: Furnished
  • Flooring: Porcelain Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 5
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground, Lighting
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: Balcony, Garden, Lighting, Outdoor Grill, Outdoor Kitchen, Playground, Private Yard, Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Enclosed, Screened
  • Porch/Patio/Deck: Covered, Enclosed, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Driveway, Oversized

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: CASABELLA
  • Driving Directions: Turn right onto Conroy Rd and continue onto Conroy Windermere Rd. Turn left onto Apopka Vineland Rd, then turn right onto Chase Rd. Turn left onto Isabella Cir into the Casabella community. Proceed through the gated entrance and follow Isabella Cir to the property.
  • Direction Faces: Northeast

School Information

  • Elementary School: Windermere Elem
  • Middle School: Bridgewater Middle
  • High School: Windermere High School

Community

  • Community Name: 34786 - Windermere
  • Community Features: Playground
  • Association: Yes
  • Assoc. Name: Tisha Hopwood / First Service Residential
  • Pet Restrictions: All information regarding Pet restrictions is deemed accurate but should be independently verified by the Buyer and Buyer's Agent.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Natural Gas Connected, Sewer Connected, Sprinkler Meter, Water Connected

Structural Information

  • Builder: TOLL BROTHERS
  • Exterior Const.: Block, Stucco
  • Roof: Tile
  • Windows: Double Pane Windows, Shades
  • Stories/Levels: Two
  • Square Feet: 5,502
  • Sq. Ft. Source: Public Records
  • Year Built: 2015

Additional Structures

  • Other Structures: Outdoor Kitchen

Lot Features

  • Property View: Garden, Pool, Trees/Woods
  • Lot Size (Acres): 0.71
  • Lot Size (Sq. Ft.): 30,855
  • Lot Size: 30855
  • Frontage: Street Paved, Private Road
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced

Financial Considerations

  • Association Fee: $1,612
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $35,130
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: CASABELLA 79/139 LOT 24
  • Flood Zone Info: X
  • APN: 122327121500240
  • Property ID: 122327121500240
  • Block/Lot/Section: 139

Listed by John Silva Realty & Associates

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Listing agents

— 4243 Isabella Cir —

  • John Silva Realty & Associates

  • John Silva Realty & Associates

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 4243 Isabella Cir

School District:Orange County School District
NameGradesDistance
Windermere Elementary School
11125 Park Avenue, Windermere, FL 34786
K-51.9 mi
Bridgewater Middle School
5600 Tiny Road, Winter Garden, FL 34787
6-82.8 mi
Windermere High School
5523 Winter Garden Vineland Road, Windermere, FL 34786
9-121.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 4243 Isabella Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/09/2026
Listed
$3,290,000
77.84%
MLS
5/11/2021
Sold
$1,850,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 4243 Isabella Cir

Year
Property Taxes
Change
Tax Assessment
Change
2025
$35,130
—
$2,092,340
-1%
2025
$35,130
8%
$2,119,070
4%
2024
$32,619
15%
$2,034,171
12%
2023
$28,379
27%
$1,824,201
33%
2021
$22,311
-12%
$1,369,840
-14%
2022
$25,446
14%
$1,593,832
16%
2021
$22,311
-3%
$1,378,013
-8%
2019
$23,065
16%
$1,504,376
28%
2018
$19,863
1%
$1,175,436
2%
2017
$19,648
—
$1,150,272
3%
2016
$19,560
876%
$1,122,207
1034%
2015
$2,005
24%
$99,000
10%
2014
$1,617
54%
$90,000
54%
2013
$1,048
—
$58,580
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 4243 Isabella Cir

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by John Silva Realty & Associates

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4243 Isabella Circle, Windermere, FL 34786 (MLS# O6439995) is a Single Family property with 5 bedrooms, 5 full bathrooms and 2 partial bathrooms. 4243 Isabella Circle is currently listed for $3,290,000 and was received on September 09, 2026. Want to learn more about 4243 Isabella Circle? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

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