5009 Pleasure Island Road, Belle Isle, FL 32809 (MLS # O6408105)

5009 Pleasure Island Road, Belle Isle, FL 32809 (MLS # O6408105)

Title: 

Cell:
Office:
Lanaguages:

407-625-6667
407-625-6667
Speaks English and Spanish

Save to Favorites
Print
Share
PRICE $1,999,000 dsIDX morgage calculator
BEDS 4
BATHS 5
HOME SIZE 5,780 sqft
LOT SIZE 25,701 sqft

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 façade, 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 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 wood-burning 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 private access to a community fishing pier on the Conway Chain of Lakes 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.

DAYS ON MARKET 1 LAST UPDATED 5/26/2026
TRACT OAK ISLAND REP 02 YEAR BUILT 1995
COMMUNITY 32809 - Orlando/Pinecastle/Oakridge/ Edgewood GARAGE SPACES 3.0
COUNTY Orange STATUS Active
PROPERTY TYPE(S) Single Family

SCHOOLS
Elementary School Pershing Elem
Jr. High School PERSHING K-8
High School Oak Ridge High


ADDITIONAL DETAILS
AIR Central Air
AIR CONDITIONING Yes
APPLIANCES Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
AREA 32809 - Orlando/Pinecastle/Oakridge/ Edgewood
CONSTRUCTION Block, Stucco
EXTERIOR Garden, Lighting, Private Yard, Rain Gutters
FIREPLACE Yes
GARAGE Yes
HEAT Central, Electric
HOA DUES 510
INTERIOR Crown Molding, Eat-in Kitchen, Stone Counters, Tray Ceiling(s), Walk-In Closet(s), Wet Bar
LOT 0.59 acre(s)
LOT DIMENSIONS 72x270x160x201
PARKING Attached
SEWER Public Sewer
STORIES 2
STYLE Traditional
SUBDIVISION OAK ISLAND REP 02
TAXES 445
WATER Public
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

0
P
I
*Estimate only

SATELLITE VIEW



 
CONTACT US ABOUT 5009 PLEASURE ISLAND ROAD
 / 
We respect your online privacy and will never spam you. By submitting this form with your telephone number you are consenting for Lee Valdes to contact you even if your name is on a Federal or State "Do not call List".

Listing provided by Christopher Christensen, ONE LUXURY INTERNATIONAL LLC, 407-312-8003
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 5/26/26 2:05 PM PDT.

This IDX solution is (c) Diverse Solutions 2026.

Scroll to Top