5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL 32809

Description of 5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL 32809

Nestled beneath a canopy of majestic moss-draped oak trees within the exclusive enclave of Oak Island, this extraordinary custom estate blends timeless Southern elegance with refined luxury and exceptional craftsmanship. Inspired by classic Greek Revival architecture, the residence commands attention with its stately columned facade, manicured gardens, and expansive motor court. A breathtaking two-story foyer introduces the residence with an elegant iron staircase, soaring ceilings, and beautifully curated architectural details throughout. The formal living and dining spaces offer timeless elegance, while the private library showcases stunning custom built-ins and refined craftsmanship rarely found today. At the heart of the home, the chef's kitchen combines warmth and functionality with custom knotty pine cabinetry, granite countertops, premium Viking appliances including double ovens, and charming stained-glass transom accents. The kitchen opens seamlessly into spacious gathering areas anchored by a marble gas fireplace and sunlit living spaces that effortlessly connect the indoors with the lush outdoor surroundings. The primary suite is a true private retreat featuring tray ceilings, rich hardwood flooring, a gas fireplace, and a stunning spa-inspired bath finished with marble flooring, a designer chandelier, oversized walk-in shower, and an exceptional custom Closet Factory dressing room. Upstairs, additional guest suites, a private study, and a dedicated studio provide incredible flexibility for both family living and entertainment. Quietly engineered for the next chapter of ownership, more than half a million dollars in recent improvements include a new roof, replacement windows, full plantation shutters, three newer AC systems, a tankless water heater, a 20kW whole-home generator, and a fully reimagined three-car garage with polyaspartic flooring. Perfectly positioned within one of Belle Isle's most desirable locations, residents enjoy a peaceful, tree-lined setting while remaining just minutes from Downtown Orlando, Orlando International Airport, Lake Nona, and SoDo. This is a truly rare opportunity to own a timeless estate where classic architecture, luxury finishes, and modern upgrades come together seamlessly.

Property Details for 5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL 32809

Bathrooms Full

4

Bathrooms Half

1

Interior Features

Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-In Closet(s), Wet Bar

Appliances

Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator

Flooring

Carpet, Ceramic Tile, Hardwood

Heating

Central, Electric

Cooling

Central Air

Furnished

Unfurnished

Architectural Style

Traditional

Garage Spaces

3

Attached Garage

Yes

Pool Private

No

Direction Faces

South

Building Information for 5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL 32809

Building Area Total

7014

Building Area Units

Square Feet

Association

Yes

Association Fee

$510

Association Fee Frequency

Quarterly

Pets Allowed

Yes

Property Information for 5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL 32809

Lot Size Square Feet

25,536

Waterfront

No

View

No

Construction Materials

Block, Stucco

Roof

Shingle

Exterior Features

Garden, Irrigation System, Lighting, Private Mailbox, Private Yard, Rain Gutters

Sewer

Public Sewer

Water Source

Public

New Construction

No

Public Records for 5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL 32809

Parcel Number

182330603100170

Tax Annual Amount

$445

Tax Year

2025

Tax Legal Description

OAK ISLAND SECOND REPLAT 24/105 LOT 17

Zoning

R-1-AA

County Or Parish

Orange

Schools Near 5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL 32809

Elementary School

Pershing Elem

Middle School

PERSHING K-8

High School

Oak Ridge High

School assignments are provided by the listing and should be independently verified.

Payment Calculator

Location