


5009 PLEASURE ISLAND ROADBELLE ISLE, FL 32809
Single Family · 4 Beds · 4 Full Baths · 1 Half Bath · 5,780 Sq. ft. | 0.59 Acres5009 PLEASURE ISLAND ROAD Overview
- Time on Site:
- 35 days
- Visits:
- 0
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.
5009 PLEASURE ISLAND ROAD Facts & Features
- Type Single Family
- Sq. ft. 5,780
- Price/Sq.ft. $346
- Lot 0.59 Acres
Details
General
Association/HOA
- Association Fee: 510
- Association Fee Frequency: Quarterly
- Association Name: Lauren Waite
- Association: Yes
School Information
- Elementary School: Pershing Elem
- Middle Or Junior School: PERSHING K-8
- High School: Oak Ridge High
Building Information
- New Construction: No
- Year Built: 1995
Location/Region
- Country: US
- County Or Parish: Orange
- MLS Area Major: 32809 - Orlando/Pinecastle/Oakridge/ Edgewood
- Subdivision Name: OAK ISLAND REP 02
- Township: 23
Tax Information
- Tax Annual Amount: 445
- Tax Year: 2025
General Information
- Furnished: Unfurnished
- Ownership: Fee Simple
- Parcel Number: 18-23-30-6031-00-170
- Pets Allowed: Yes
- Property Sub Type: Single Family Residence
- Property Type: Residential
- Senior Community: No
- Special Listing Conditions: None
- Zoning: R-1-AA
Interior
Parking Information
- Garage Spaces: 3
- Garage: Yes
Beds/Baths
- Bathrooms Full: 4
- Bathrooms Half: 1
- Bathrooms Total: 5
- Bedrooms Total: 4
Building Interior
- Building Area Source: Public Records
- Building Area Total: 7014
- Building Area Units: Square Feet
General Information
- Appliances: Built-In Oven,Dishwasher,Disposal,Electric Water Heater,Microwave,Range,Refrigerator
- Cooling: Central Air
- Fireplace Features: Family Room,Gas,Primary Bedroom,Wood Burning
- Fireplace: Yes
- Flooring: Carpet,Ceramic Tile,Wood
- Foundation Details: Slab
- Heating: Central,Electric
- Interior Features: Ceiling Fans(s),Crown Molding,Eat-in Kitchen,Solid Wood Cabinets,Split Bedroom,Stone Counters,Tray Ceiling(s),Walk-In Closet(s),Wet Bar
- Laundry Features: Laundry Room
- Levels: Two
- Living Area: 5780
- Living Area Source: Public Records
- Living Area Units: Square Feet
- Other Equipment: Irrigation Equipment,Private Yard
Exterior
Lot Information
- Additional Parcels: No
- Lot Size Acres: 0.59
- Lot Size Dimensions: 72x270x160x201
- Lot Size Square Feet: 25536
- Road Surface Type: Asphalt
- Water Source: Public
Waterfront/View
- Waterfront: No
Building Exterior/Construction
- Architectural Style: Traditional
- Attached Garage: Yes
- Construction Materials: Block,Stucco
- Direction Faces: South
- Roof: Shingle
General Information
- Carport: No
- Exterior Features: Garden,Lighting,Private Mailbox,Private Yard,Rain Gutters
- Pool Private: No
- Sewer: Public Sewer
- Utilities: Public
Room Information
Room: Bedroom 4
- Level: First
- Dimensions: 12x12
- Length: 12
- Width: 12
Room: Dining Room
- Level: First
- Dimensions: 16x13
- Length: 13
- Width: 16
Room: Kitchen
- Level: First
- Dimensions: 27x19
- Length: 19
- Width: 27
Room: Living Room
- Level: First
- Dimensions: 17x13
- Length: 13
- Width: 17
Room: Bedroom 2
- Level: Second
- Dimensions: 15x12
- Length: 12
- Width: 15
Room: Bedroom 3
- Level: Second
- Dimensions: 13x12
- Length: 12
- Width: 13
Room: Bonus Room
- Level: Second
- Dimensions: 26x10
- Length: 10
- Width: 26
Room: Den
- Level: Second
- Dimensions: 14x12
- Length: 12
- Width: 14
Room: Primary Bedroom
- Level: Second
- Dimensions: 19x16
- Length: 16
- Width: 19
Room: Studio
- Level: Second
- Dimensions: 26x10
- Length: 10
- Width: 26
5009 PLEASURE ISLAND ROAD Neighborhood
Community
32809 (ORLANDO) Demographics
Schools
School data unavailable, School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.5009 PLEASURE ISLAND ROAD Monthly Cost
5009 PLEASURE ISLAND ROAD Market Data
Based on the last 30 days in this zip code
5009 PLEASURE ISLAND ROAD History
| Date | Value | Agent |
|---|---|---|
| 5/26/2026Source: My Florida Regional MLS | May 26, 2026 |
|
| 10/14/2022Source: My Florida Regional MLS | October 14, 2022 |



































































