Listing provided courtesy of ONE LUXURY INTERNATIONAL LLCas Distributed by MLSGrid- MLS# MFRO6408105MLS Provider

5009 PLEASURE ISLAND ROADBELLE ISLE, FL 32809

Single Family · 4 Beds · 4 Full Baths · 1 Half Bath · 5,780 Sq. ft. | 0.59 Acres
$1,999,000 Active

5009 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.

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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

35
Median Age
2,452
Population Density (per sq. mile)
31%
College Educated
$45,205
Estimated Median Income
4,895
Estimated Total Home Owners
4,562
Estimated Total Renters
52% / 48%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

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

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

5009 PLEASURE ISLAND ROAD Market Data

Based on the last 30 days in this zip code

$346,514
Average List Price
$276
Average Price per Square Foot
11
Properties Sold
133
Average Days on Market
108
Properties for Sale
Calculations provided by Reliance Network

5009 PLEASURE ISLAND ROAD History

Date Event Value Agent
5/26/2026Source: My Florida Regional MLS Added to Database
May 26, 2026
10/14/2022Source: My Florida Regional MLS Added to Database
October 14, 2022