$1,999,000
5009 Pleasure Island Road Belle Isle, FL 32809
For Sale MLS# O6408105
4 beds 5 baths 5,780 sq ft Single Family
Details for 5009 Pleasure Island Road
MLS# O6408105
Description for 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 new 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.
Listing Information
Property Type: Residential, Single Family Residence
Status: Active
Bedrooms: 4
Bathrooms: 5
Lot Size: 0.59 Acres
Square Feet: 5,780 sq ft
Year Built: 1995
Garage: Yes
Stories: 2 Story
Construction: Block,Stucco
Subdivision: Oak Island Rep 02
Foundation: Slab
County: Orange
School Information
Elementary: Pershing Elem
Middle: Pershing K-8
High: Oak Ridge High
Room Information
Main Floor
Living Room: 13x17
Bedroom 4: 12x12
Dining Room: 13x16
Kitchen: 19x27
Upper Floor
Bonus Room: 10x26
Studio: 10x26
Den: 12x14
Bedroom 3: 12x13
Bedroom 2: 12x15
Primary Bedroom: 16x19
Bathrooms
Full Baths: 4
1/2 Baths: 1
Additonal Room Information
Laundry: Laundry Room
Interior Features
Appliances: Electric Water Heater, Built-In Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator
Flooring: Carpet,Ceramic Tile,Wood
Fireplaces: Family Room, Gas, Wood Burning, Primary Bedroom
Additional Interior Features: Ceiling Fan(s), Wet Bar, Eat-In Kitchen, Tray Ceiling(s), Built-in Features, Split Bedrooms, Walk-In Closet(s), Stone Counters, Wood Cabinets, Crown Molding
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Municipal Utilities
Cooling: Central Air, Ceiling Fan(s)
Heating: Electric, Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 3
Roof: Shingle
Lot Dimensions: 72x270x160x201
Additional Exterior/Lot Features: Private Yard, Sprinkler/Irrigation, Rain Gutters, Lighting, Garden
Community Features
Homeowners Association: Yes
HOA Dues: $510 / Quarterly
Driving Directions
From Orange Avenue go east on Hoffner to left on Pleasure Island Road
Financial Considerations
Tax/Property ID: 18-23-30-6031-00-170
Tax Amount: 445
Tax Year: 2025
A broker reciprocity listing courtesy: ONE LUXURY INTERNATIONAL LLC
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Interest rate and annual percentage rate (APR) are based on current market conditions, are for informational purposes only, are subject to change without notice and may be subject to pricing add-ons related to property type, loan amount, loan-to-value, credit score and other variables. Estimated closing costs used in the APR calculation are assumed to be paid by the borrower at closing. If the closing costs are financed, the loan, APR and payment amounts will be higher. If the down payment is less than 20%, mortgage insurance may be required and could increase the monthly payment and APR. Contact us for details. Additional loan programs may be available. Accuracy is not guaranteed, and all products may not be available in all borrower's geographical areas and are based on their individual situation. This is not a credit decision or a commitment to lend.
Sales History & Tax Summary for 5009 Pleasure Island Road
Sales History
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Tax Summary
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 5009 Pleasure Island Road
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The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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