5009 PLEASURE ISLAND ROAD BELLE ISLE, FL 32809

update time: 06/22/2026 17:17:49

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.

From Orange Avenue go east on Hoffner to left on Pleasure Island Road

Property Details

Nearby Properties

Single Family Residence Active

123 S WIGGINS ROAD PLANT CITY, FL 33566

4 Beds1/2Baths2,816sqft2007 built

$849,000.00

Single Family Residence Active

4623 CONWAY GARDENS ROAD ORLANDO, FL 32806

3 Beds0/2Baths1,928sqft1969 built

$389,900.00

Single Family Residence Active

22519 SOUTHSHORE DRIVE LAND O LAKES, FL 34639

4 Beds0/3Baths4,503sqft2006 built

$995,000.00

Single Family Residence Active

5060 STARLING DRIVE MULBERRY, FL 33860

3 Beds0/2Baths2,035sqft1975 built

$430,000.00

Single Family Residence Active

810 W BRADDOCK STREET TAMPA, FL 33603

5 Beds0/4Baths4,509sqft2026 built

$1,599,999.00

Single Family Residence Active

4358 TIDEWATER DRIVE ORLANDO, FL 32812

4 Beds1/3Baths4,368sqft1978 built

$1,615,000.00

Single Family Residence Active

3707 MARCH AVENUE ORLANDO, FL 32806

4 Beds1/2Baths2,172sqft1958 built

$465,000.00

Condominium Active

345 BAYSHORE BOULEVARD UNIT GP06 TAMPA, FL 33606

2 Beds0/2Baths1,170sqft1998 built

$735,000.00

Single Family Residence Active

3611 ELOISE STREET ORLANDO, FL 32806

3 Beds0/2Baths2,343sqft1966 built

$550,000.00

Condominium Active

3101 BAYSHORE BOULEVARD UNIT 2501 TAMPA, FL 33629

4 Beds1/5Baths6,739sqft2024 built

$6,499,000.00

Condominium Active

6311 NEWTOWN CIRCLE UNIT 11B2 TAMPA, FL 33615

2 Beds1/2Baths1,260sqft1979 built

$150,000.00

Single Family Residence Active

1530 WATERWITCH DRIVE ORLANDO, FL 32806

5 Beds2/5Baths10,187sqft1963 built

$7,900,000.00

Single Family Residence Active

2813 TIMBERLAKE DRIVE ORLANDO, FL 32806

4 Beds0/3Baths3,200sqft1964 built

$699,000.00

Condominium Active

3711 W IOWA AVENUE UNIT 214 TAMPA, FL 33611

2 Beds0/2Baths910sqft1990 built

$189,900.00

Single Family Residence Active

1500 MAPLE STREET CLEARWATER, FL 33755

6 Beds1/5Baths4,127sqft1925 built

$1,399,000.00

Single Family Residence Active

549 PENINSULAR DRIVE LAKELAND, FL 33813

3 Beds0/2Baths3,091sqft1990 built

$399,000.00

Single Family Residence Active

5120 MORTIER AVENUE BELLE ISLE, FL 32812

3 Beds0/2Baths2,536sqft1960 built

$519,900.00

Single Family Residence Active

4801 BIG OAKS LANE ORLANDO, FL 32806

4 Beds0/2Baths2,630sqft1965 built

$528,000.00

Single Family Residence Active

1512 OVERLAKE AVENUE ORLANDO, FL 32806

3 Beds0/2Baths1,979sqft1959 built

$420,000.00

Single Family Residence Active

5020 SAINT MARIE AVENUE BELLE ISLE, FL 32812

4 Beds0/2Baths2,911sqft1960 built

$475,000.00