Gabriella Massaro

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

$4,995,000.00
5070 DOWN POINT LANE, WINDERMERE, FL - 34786
6 beds
6.5 baths
7,349 sqft
$4,995,000.00
5070 DOWN POINT LANE, WINDERMERE, FL - 34786
Gabriella Massaro
$4,995,000.00
6 beds
6.5 baths
7,349 sqft
5070 DOWN POINT LANE, WINDERMERE, FL - 34786
For Sale
Photo 1
  • Built in 1998
  • 4 garage spaces
  • $679.68/sqft
  • Lot size: 2.64 acres
  • 2 days on market

Nestled behind the gates in the heart of Windermere, this exceptional lakefront estate commands sweeping views across the renowned Butler Chain of Lakes. Designed for refined living and effortless entertaining, the residence offers six bedrooms, six full baths, and a powder bath — including a fully equipped private guest apartment ideal for extended family or long-term visitors. From the moment you arrive, the home’s striking architectural presence is undeniable. A dramatic entry with soaring ceilings and intricate iron detailing introduces expansive living spaces crafted with both grandeur and comfort in mind. Walls of glass and retractable doors blur the line between indoors and out, inviting natural light and panoramic lake vistas into nearly every room. The main level showcases elegant formal spaces, a richly appointed study, and a music room, along with a stunning lakefront family room and game room complete with a stylish wet bar. At the heart of the home, the gourmet kitchen features premium finishes, abundant workspace, and seamless flow for hosting gatherings large or intimate. The primary suite and an additional guest suite are thoughtfully positioned on the first floor for privacy and convenience. Upstairs, guests are treated to elevated lake views from a spacious lounge with kitchenette, multiple bedroom suites, a private theater with adjoining sitting area, and a spectacular balcony overlooking the water. Outdoor living is simply extraordinary. A heated saltwater pool and spa anchor the expansive terrace, complemented by a summer kitchen, bar seating, and a fireplace — the perfect setting for sunset evenings on the water. A private boathouse offers direct access for boating, paddleboarding, or fishing along one of Central Florida’s most coveted waterways. Despite its serene setting, the home is just minutes from upscale shopping, dining, and world-class attractions, including Walt Disney World, and approximately 20 minutes to Orlando International Airport. With the owners preparing for their next chapter, this extraordinary waterfront retreat presents a rare opportunity to own on the Butler Chain at a compelling value. A lifestyle of privacy, beauty, and convenience awaits.

  • Directions: FL-408 W, take Exit 2 for Good Homes Rd, turn left onto Good Homes Rd, turn left onto State Hwy 526, turn right onto S Apopka Vineland Rd Turn right onto Conroy Windermere Rd, Turn right onto Down Point Ln, destination will be on the left.
  • County: Orange
  • Geo subdivision: SUNSET BAY

Nearby Schools

Windermere Elem

Chain of Lakes Middle

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

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

See also

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9721 CARILLON PARK DRIVE, WINDERMERE, FL - 34786
$5,000,000.00
6 bds
8.0 ba
8,305 sqft
9721 CARILLON PARK DRIVE, WINDERMERE, FL - 34786
For Sale
3026 PORTO LAGO COURT, WINDERMERE, FL - 34786
$4,500,000.00
5 bds
8.0 ba
8,714 sqft
3026 PORTO LAGO COURT, WINDERMERE, FL - 34786
For Sale
8968 BAY COVE COURT, ORLANDO, FL - 32819
$4,499,995.00
6 bds
6.5 ba
5,428 sqft
8968 BAY COVE COURT, ORLANDO, FL - 32819
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6385276
Listing updated: February 28, 2026 at 7:05PM
Listing provided by: Isis Sarcos, EXP REALTY LLC
Last checked 21 hours ago
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