Gabriella Massaro

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

$1,795,000.00
15717 E OAKLAND AVENUE, WINTER GARDEN, FL - 34787
4 beds
3.5 baths
3,515 sqft
$1,795,000.00
15717 E OAKLAND AVENUE, WINTER GARDEN, FL - 34787
Gabriella Massaro
$1,795,000.00
4 beds
3.5 baths
3,515 sqft
15717 E OAKLAND AVENUE, WINTER GARDEN, FL - 34787
For Sale
Photo 1
  • Built in 1997
  • 2 garage spaces
  • $510.67/sqft
  • Lot size: 43,438 sqft
  • 19 days on market

Welcome to this exceptional ONE-OWNER CUSTOM HOME, sitting on a ONE-ACRE HOMESITE in one of Oakland’s most sought-after locations. Offering 3,515 square feet of living space (4,890 total square feet), this thoughtfully designed 4-bedroom, 3.5-bath residence combines timeless Old Florida charm with OUTSTANDING QUALITY CONSTRUCTION, FEATURING ALL-STEEL CONSTRUCTION—INCLUDING STEEL ROOF TRUSSES—for exceptional durability and peace of mind. A circular driveway and side-entry OVERSIZED TWO-CAR GARAGE create impressive curb appeal, while double front doors welcome you into a spacious, OPEN FLOOR PLAN with 17.5' VAULTED CEILINGS in living area and 10' CEILING HEIGHT in bedrooms.This home has been designed for both everyday living and entertaining. At the heart of the home is a stunning DOUBLE-SIDED FIREPLACE with Tennessee Stone which creates a beautiful focal point between the formal living room and the inviting family room. The living areas flows seamlessly into the kitchen, separated only by a short wall between the kitchen and dining room that preserves the home’s open, airy feel. The EXPANSIVE KITCHEN is designed to bring everyone together, featuring TWO SINKS, a WRAPAROUND BREAKFAST BAR with seating for up to eight, a center ISLAND WITH COOKTOP, generous eat-in dining area, WALK-IN PANTRY with custom built-in shelving, and abundant countertop workspace. The open layout allows the kitchen, dining, and living areas to remain connected, making this home ideal for entertaining, holidays, and family gatherings. The desirable THREE-WAY SPLIT FLOOR PLAN offers both privacy and flexibility. Two secondary bedrooms and a full bath are located toward the front of the home, while a separate guest wing features an additional bedroom, full bath, oversized laundry room with storage, and a convenient half bath. Privately tucked away on the opposite side of the home, the spacious primary suite offers two walk-in closets and an ensuite bath with a walk-in shower. Double glass doors open to an expansive screened lanai that extends the living space outdoors, complete with a summer kitchen and peaceful views of the lush backyard. Additional updates include a tile roof (2015), HVAC ductwork (2020), exterior stucco upgrades and fresh paint (2021), one water heater replaced in 2018 and the second in February 2025, Connection to city water in 2019, The well was retained exclusively for lawn irrigation. Perfectly located with convenient access to the Florida Turnpike, Highway 50, shopping, dining, and area attractions. This meticulously maintained custom home offers the rare combination of quality construction, timeless design, generous living spaces, and an unbeatable Oakland location. This is Florida living at its finest.

  • Directions: From the Florida's Turnpike, exit 272 for FL50 E toward Winter Garden, Merge onto FL-50 E/W Colonial Drive, Left onto S Tubb St, Right onto E Oakland Ave, 15717 on the left.
  • County: Orange
  • Geo subdivision: OAKLAND

Nearby Schools

Tildenville Elem

Lakeview Middle

West Orange High

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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15910 VETTA DRIVE, BELLA COLLINA, FL - 34756
$1,810,000.00
4 bds
4.5 ba
3,804 sqft
15910 VETTA DRIVE, BELLA COLLINA, FL - 34756
For Sale
15915 VETTA DRIVE, MONTVERDE, FL - 34756
$1,900,000.00
4 bds
4.5 ba
3,997 sqft
15915 VETTA DRIVE, MONTVERDE, FL - 34756
For Sale
15825 VETTA DRIVE, BELLA COLLINA, FL - 34756
$1,900,000.00
4 bds
4.5 ba
3,997 sqft
15825 VETTA DRIVE, BELLA COLLINA, FL - 34756
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6419032
Listing updated: July 25, 2026 at 5:05PM
Listing provided by: Janelle Conway, CARIS REALTY AND INVESTMENTS INC
Last checked 20 hours ago
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