1-407-575-5392
Menu

5009 Pleasure Island Road, Belle Isle, FL

NEXT
PREV
$1,999,000

($346/sqft)

List Status: Active
5009 Pleasure Island Road
Belle Isle, FL 32809


4 beds
4 baths
5780 living sqft
Top Features
  • Subdivision: Oak Island Rep 02
  • Built in  1995
  • Single Family Residence
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 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
Property Details
Property Features
Property Sub Type
Single Family Residence
County
Orange
Subdivision
OAK ISLAND REP 02
Additional Information
Additional Lease Restrictions
Verify with HOA.
Additional Parcels YN
false
Alternate Key Folio Num
18-23-30-6031-00-170
Appliances
Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
Architectural Style
Traditional
Association Email
lwaite@lelandmanagement.com
Association Fee
510
Association Fee Frequency
Quarterly
Association Fee Requirement
Required
Association YN
true
Attached Garage YN
true
Available For Lease YN
1
Bathrooms Total Integer
5
Building Area Source
Public Records
Building Area Total
7014
Building Area Total Srch SqM
651.62
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
345.85
Carport YN
false
Construction Materials
Block, Stucco
Cooling
Central Air
Country
US
Cumulative Days On Market
27
Current Price
1999000.00
Direction Faces
South
Elementary School
Pershing Elem
Exterior Features
Garden, Lighting, Private Mailbox, Private Yard, Rain Gutters
Fireplace Features
Family Room, Gas, Primary Bedroom, Wood Burning
Fireplace YN
true
Flood Zone Code
X
Flood Zone Date
2009-09-25
Flood Zone Panel
12095C0430F
Flooring
Carpet, Ceramic Tile, Wood
Foundation Details
Slab
Furnished
Unfurnished
Garage Spaces
3
Garage YN
true
Heating
Central, Electric
High School
Oak Ridge High
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
Internet Address Display YN
true
Internet Automated Valuation Display YN
false
Internet Consumer Comment YN
false
Internet Entire Listing Display YN
true
Laundry Features
Laundry Room
Lease Restrictions YN
1
Levels
Two
List AOR
Orlando Regional
Living Area Meters
536.98
Living Area Source
Public Records
Living Area Units
Square Feet
Lot Size Acres
0.59
Lot Size Dimensions
72x270x160x201
Lot Size Square Feet
25536
Lot Size Square Meters
2372
Middle Or Junior School
PERSHING K-8
Minimum Lease
8-12 Months
Modification Timestamp
2026-06-22T17:18:10.882Z
Monthly HOA Amount
170.00
New Construction YN
false
Occupant Type
Owner
Other Equipment
Irrigation Equipment, Private Yard
Ownership
Fee Simple
Parcel Number
18-23-30-6031-00-170
Pet Restrictions
Verify with HOA.
Pets Allowed
Yes
Pool Private YN
false
Postal Code Plus 4
3591
Public Survey Range
30
Public Survey Section
18
RATIO Current Price By Calculated SqFt
345.85
Road Surface Type
Asphalt
Roof
Shingle
Room Count
10
Senior Community YN
false
Sewer
Public Sewer
Showing Requirements
24 Hour Notice, Appointment Only, Call Listing Agent, Listing Agent Must Accompany, No Lockbox, See Remarks
Status Change Timestamp
2026-05-26T19:30:41.000Z
Tax Annual Amount
445
Tax Block
00
Tax Book Number
24-105
Tax Legal Description
OAK ISLAND SECOND REPLAT 24/105 LOT 17
Tax Lot
17
Tax Year
2025
Total Acreage
1/2 to less than 1
Total Annual Fees
2040.00
Total Monthly Fees
170.00
Township
23
Universal Property Id
US-12095-N-182330603100170-R-N
Unparsed Address
5009 PLEASURE ISLAND RD
Utilities
Public
Water Source
Public
Waterfront YN
false
Zoning
R-1-AA
Neighborhood Map
Popup

Property Photos
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo
Listing Photo

MLS #MFRO6408105 Listing courtesy of One Luxury International Llc provided by Stellar MLS.



All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 7/12/26 11:02 AM) |

Listing Search



Translate Tool

Featured Listings
Altamonte Springs Real Estate
$1,149,000
5 BED
4 BATH
WELCOME TO ONE OF ALTAMONTE SPRINGS' MOST UNIQUE PRIVATE ESTATES. Hidden behind a private automatic gate and nestled on ... Read More
Altamonte Springs Real Estate
$1,399,000
4 BED
5 BATH
Welcome to this beautifully crafted home built in 2004, located in the private, gated community of Spring Lake Pointe, j... Read More
Apopka Real Estate
$1,250,000
4 BED
2 BATH
4 Acres with Two Structures – Endless Potential! Nestled on approximately 4 acres, this exceptional property features tw... Read More
Apopka Real Estate
$1,250,000
6 BED
4 BATH
Enjoy the space, privacy, and tremendous potential offered by this spectacular 6.40-acre property! The property features... Read More
Apopka Real Estate
$1,295,000
3 BED
2 BATH
This is the place to build your estate or build multiple single family homes. Conveniently located in Apopka. The area i... Read More
Apopka Real Estate
$1,250,000
5 BED
4 BATH
Under Construction. Experience luxury living from Nest Homes by Urban Perch, award-winning custom home builder. This tho... Read More
Apopka Real Estate
$1,010,000
5 BED
3 BATH
Welcome to your private slice of Central Florida. Situated on 1.25 fully fenced acres with no HOA, this custom-built hom... Read More
Apopka Real Estate
$1,500,000
4 BED
3 BATH
Welcome to 4275 Round Lake Road, a rare opportunity to own 10 gorgeous acres of private, gated property in Apopka. Lovin... Read More
Apopka Real Estate
$1,000,000
7 BED
8 BATH
An exceptional investment opportunity awaits with this beautifully maintained, five-unit residential enclave. Nestled on... Read More
Contact Wendy Morris

407-575-5392

Wendy Morris LLC

Licensed in the State of Florida
BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787

Your privacy is our utmost concern. We will never sell your personal information. Privacy Policy
©2026 windermereluxuryproperty.com - all rights reserved. | Site Map