5009 PLEASURE ISLAND RD, Belle Isle, FL 32809
5009 PLEASURE ISLAND RD, Belle Isle, FL 32809
5009 PLEASURE ISLAND RD, Belle Isle, FL 32809
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STACY WEINGARTEN

STACY WEINGARTEN

+1(941) 432-4141
$1,899,000
Est. payment /mo
4 Beds
5 Baths
5,780 SqFt
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Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active Under Contract

Purchase Type For Sale

Square Footage 5,780 sqft

Price per Sqft $328

Subdivision Oak Island Rep 02

MLS Listing ID O6408105

Bedrooms 4

Full Baths 4

Half Baths 1

HOA Fees $510/qua

HOA Y/N Yes

Annual Recurring Fee 2040.0

Year Built 1995

Annual Tax Amount $445

Lot Size 0.590 Acres

Acres 0.59

Lot Dimensions 72x270x160x201

Property Sub-Type Single Family Residence

Source Stellar MLS

Property Description

Under contract-accepting backup offers. 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.

Location

State FL

County Orange

Community Oak Island Rep 02

Area 32809 - Orlando/Pinecastle/Oakridge/ Edgewood

Zoning R-1-AA

Interior

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

Heating Central, Electric

Cooling Central Air

Flooring Carpet, Ceramic Tile, Wood

Fireplaces Type Family Room, Gas, Primary Bedroom, Wood Burning

Furnishings Unfurnished

Fireplace true

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

Laundry Laundry Room

Exterior

Exterior Feature Garden, Lighting, Private Mailbox, Private Yard, Rain Gutters

Garage Spaces 3.0

Utilities Available Public

View Y/N No

Water Access No

Roof Type Shingle

Attached Garage true

Exposure South

Garage true

Private Pool No

Building

Entry Level Two

Foundation Slab

Lot Size Range 1/2 to less than 1

Sewer Public Sewer

Water Public

Architectural Style Traditional

Structure Type Block,Stucco

New Construction false

Schools

Elementary Schools Pershing Elem

Middle Schools Pershing K-8

High Schools Oak Ridge High

Others

Pets Allowed Yes

Senior Community No

Ownership Fee Simple

Monthly Total Fees $170

Membership Fee Required Required

Special Listing Condition None

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Stellar MLS
© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved.
Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC

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