Gabriella Massaro

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

$939,000.00
11942 SHELTERING PINE DRIVE, ORLANDO, FL - 32836
5 beds
3.5 baths
3,851 sqft
$939,000.00
11942 SHELTERING PINE DRIVE, ORLANDO, FL - 32836
Gabriella Massaro
$939,000.00
5 beds
3.5 baths
3,851 sqft
11942 SHELTERING PINE DRIVE, ORLANDO, FL - 32836
For Sale
Photo 1
  • Built in 2007
  • 3 garage spaces
  • $243.83/sqft
  • Lot size: 8,341 sqft
  • 5 days on market

Never listed before, this beautifully maintained residence is located in Grande Pines, an intimate community of only sixty homes just 1 mile from Disney and Winter Garden, — offering the rare opportunity to enjoy nightly fireworks from the comfort of your own backyard. This exceptional 5-bedroom, 3.5-bath home blends modern convenience with the timeless appeal of a traditional family home. Thoughtfully cared for by one owner, the property features a split 3-car garage and a classic two-staircase design that enhances both flow and privacy. One staircase leads to three spacious secondary bedrooms, while the second provides a private entry to the upstairs primary suite — a layout reminiscent of traditional homes where separation and quiet retreat were key elements of design. Inside, generous room sizes, walk-in closets, and designer window treatments evoke the warmth and character of a traditional home, while the true chef’s kitchen — complete with abundant cabinetry, stone counters, and double ovens — offers both charm and functionality. A flexible downstairs room (bedroom #5) serves perfectly as an office, playroom, craft room, or additional bedroom. Storage is abundant throughout, including extensive under-stair storage, linen closets in every bathroom and bonus room, which reflects the practical, built-in organization needed for busy family life. Situated on a premium lot beside protected community space that will never be developed, the home offers a sweeping yard, peaceful views, and a private pool and spa overlooking a serene water vista. Recent upgrades include two new A/C units (2019), a fully rescreened pool enclosure (2020), new roof (2023), freshly painted pool decking and enclosure (2024), not to mention the whole house water softener and surround sound! Located within Windermere’s top-rated school district and close to major highways, fine dining, and premier shopping, this home offers the perfect blend of traditional comfort, modern luxury, and the exclusivity of living in Grande Pines.

  • Directions: Take SR 535 to Reams Rd. Turn left onto Delmar Ave then left into Grande Pines. Turn left onto Sheltering Pine Dr. Home will be first home on the right.
  • County: Orange
  • Geo subdivision: GRANDE PINES

Nearby Schools

Castleview Elementary

Horizon West Middle School

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
3629 LAKE BUYNAK ROAD, WINDERMERE, FL - 34786
$975,000.00
4 bds
3.5 ba
2,618 sqft
3629 LAKE BUYNAK ROAD, WINDERMERE, FL - 34786
For Sale
13536 SUNSET LAKES CIRCLE, WINTER GARDEN, FL - 34787
$1,025,000.00
5 bds
4.0 ba
3,389 sqft
13536 SUNSET LAKES CIRCLE, WINTER GARDEN, FL - 34787
For Sale
6100 CYPRESS HILL ROAD, WINTER GARDEN, FL - 34787
$875,000.00
5 bds
3.0 ba
3,777 sqft
6100 CYPRESS HILL ROAD, WINTER GARDEN, FL - 34787
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6422347
Listing updated: July 26, 2026 at 2:24PM
Listing provided by: Kristy Kennedy, FATHOM REALTY FL LLC
Last checked 11 hours ago
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