Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$3,290,000.00
4243 ISABELLA CIRCLE, WINDERMERE, FL - 34786
5 beds
6.0 baths
5,502 sqft
$3,290,000.00
4243 ISABELLA CIRCLE, WINDERMERE, FL - 34786
Gabriella Massaro
$3,290,000.00
5 beds
6.0 baths
5,502 sqft
4243 ISABELLA CIRCLE, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 2015
  • 3 garage spaces
  • $597.96/sqft
  • Lot size: 30,855 sqft
  • 3 days on market

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.

  • 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.
  • County: Orange
  • Geo subdivision: CASABELLA

Nearby Schools

Windermere Elem

Bridgewater Middle

Windermere High School

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

For Sale
7720 FICQUETTE ROAD, WINDERMERE, FL - 34786
$3,100,000.00
6 bds
4.5 ba
4,282 sqft
7720 FICQUETTE ROAD, WINDERMERE, FL - 34786
For Sale
1113 HOLSTONS POINTE PLACE, GOTHA, FL - 34734
$3,280,000.00
6 bds
5.0 ba
5,226 sqft
1113 HOLSTONS POINTE PLACE, GOTHA, FL - 34734
For Sale
515 W 2ND AVENUE, WINDERMERE, FL - 34786
$3,300,000.00
4 bds
5.5 ba
3,966 sqft
515 W 2ND AVENUE, WINDERMERE, FL - 34786
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6439995
Listing updated: September 11, 2026 at 10:47AM
Listing provided by: John Silva, JOHN SILVA REALTY & ASSOCIATES
Last checked 21 hours ago
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