Gabriella Massaro

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

$3,300,000.00
515 W 2ND AVENUE, WINDERMERE, FL - 34786
4 beds
5.5 baths
3,966 sqft
$3,300,000.00
515 W 2ND AVENUE, WINDERMERE, FL - 34786
Gabriella Massaro
$3,300,000.00
4 beds
5.5 baths
3,966 sqft
515 W 2ND AVENUE, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1961
  • 3 garage spaces
  • $832.07/sqft
  • Lot size: 28,894 sqft
  • 7 days on market

Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living.

  • Directions: Maguire / Main St to 2nd Avenue go West to the home
  • County: Orange
  • Geo subdivision: WINDERMERE TOWN

Nearby Schools

Windermere Elem

Gotha Middle

Olympia High

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

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

See also

For Sale
5379 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
$3,400,000.00
4 bds
3.5 ba
3,872 sqft
5379 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
For Sale
4243 ISABELLA CIRCLE, WINDERMERE, FL - 34786
$3,290,000.00
5 bds
6.0 ba
5,502 sqft
4243 ISABELLA CIRCLE, WINDERMERE, FL - 34786
For Sale
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
$3,189,000.00
4 bds
4.5 ba
3,365 sqft
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL - 34786
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6439554
Listing updated: September 9, 2026 at 1:16AM
Listing provided by: Darrell Nunnelley, VINTAGE REALTY GROUP LLC
Last checked 3 days ago
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