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5009 Pleasure Island Road, Belle Isle, FL 32809

$1,999,000
  • 5009 Pleasure Island Road, Belle Isle, FL 32809 Main Photo

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New to the Market Active
BEDS4 BATHS4 full 1 partial SQUARE FEET5,780 MLS#O6408105
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONOAK ISLAND REP 02

Property Description

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.

5009 Pleasure Island Road | MLS# O6408105

This single family home located at 5009 Pleasure Island Road, Belle Isle, FL 32809 is currently listed for sale with an asking price of $1,999,000. This property was built in 1995 and has 4 bedrooms and 4 full and 1 partial baths with 5780 sq. ft. Pleasure Island Road is located in the OAK ISLAND REP 02 subdivision. Search OAK ISLAND REP 02 real estate on greberte.realty100.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 3 car attached
Heating: Central, Electric
Home Style: Traditional
Lot Size: 0.59 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $445
Year Built: 1995

Amenities

Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Solid Wood Cabinets
Split Bedroom
Stone Counters
Tray Ceiling(s)
Walk-In Closet(s)
Wet Bar
Garden
Lighting
Private Mailbox
Private Yard
Rain Gutters

Feature Descriptions

Appliances: Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
Directions: From Orange Avenue go east on Hoffner to left on Pleasure Island Road
Exterior: Block, Stucco
Fireplace: Family Room, Gas, Primary Bedroom, Wood Burning
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Carpet, Ceramic Tile, Wood
Foundation: Slab
HOA Fee: 510/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Lot Dimensions: 0.59
Other Equipment: Irrigation Equipment, Private Yard
Ownership: Fee Simple
Pets Allowed: Yes
Pets Restrictions: Verify with HOA.
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: 24 Hour Notice, Appointment Only, Call Listing Agent, Listing Agent Must Accompany, No Lockbox, See Remarks
Special Sale Provisions: None
Utilities: Public
Water: Public
Water Access Y/N: No
Zoning: R-1-AA

Room Sizes

Living Room: 17x13
Kitchen: 27x19
Dining Room: 16x13
Primary Bedroom: 19x16
Bedroom 2: 15x12
Bedroom 3: 13x12
Bedroom 4: 12x12
Den: 14x12
Studio: 26x10
Bonus Room: 26x10

Local Schools

High School: Oak Ridge High
Middle School: PERSHING K-8
Elementary School: Pershing Elem

Listed By / Shown By

Listed By

Agency Name: ONE LUXURY INTERNATIONAL LLC
Agency Contact: 407-312-8003

Shown By

Agent Name: Garbriel Reberte
Agent Phone: (561) 299-6929
Agency Title: Realty 100

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Estimated Payment

$ 5,069.03 per month $4,448.91 Principal & Interest $37.08 Property Tax $583.04 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/27/2026. The listing information on this page last changed on 05/27/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 05/27/2026 12:00:43 AM EST) or Miami MLS (last updated Tue 05/26/2026 11:58:31 PM EST) or Stellar MLS (last updated Tue 05/26/2026 11:44:02 PM EST) or Beaches MLS (last updated Tue 05/26/2026 5:59:08 PM EST). Real estate listings held by brokerage firms other than Realty 100 may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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