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.
For sale
$1,999,000
5009 Pleasure Island Rd, Belle Isle, FL 32809
4beds
5,780sqft
Single Family Residence
Built in 1995
0.59 Acres Lot
$-- Zestimate®
$346/sqft
$170/mo HOA
What's special
Gas fireplaceMarble gas fireplaceAdditional guest suitesNew roofGranite countertopsElegant iron staircaseStunning custom built-ins
- 27 days |
- 1,516 |
- 75 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Christopher Christensen 407-312-8003,
ONE LUXURY INTERNATIONAL LLC 407-312-8003,
Desmond Garcia LLC 407-202-5104,
ONE LUXURY INTERNATIONAL LLC
Source: Stellar MLS,MLS#: O6408105
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s)
- Level: Second
- Area: 304 Square Feet
- Dimensions: 19x16
Bedroom 2
- Features: Built-in Closet
- Level: Second
- Area: 180 Square Feet
- Dimensions: 15x12
Bedroom 3
- Features: Walk-In Closet(s)
- Level: Second
- Area: 156 Square Feet
- Dimensions: 13x12
Bedroom 4
- Features: Built-in Closet
- Level: First
- Area: 144 Square Feet
- Dimensions: 12x12
Bonus room
- Features: No Closet
- Level: Second
- Area: 260 Square Feet
- Dimensions: 26x10
Den
- Level: Second
- Area: 168 Square Feet
- Dimensions: 14x12
Dining room
- Level: First
- Area: 208 Square Feet
- Dimensions: 16x13
Kitchen
- Level: First
- Area: 513 Square Feet
- Dimensions: 27x19
Living room
- Level: First
- Area: 221 Square Feet
- Dimensions: 17x13
Other
- Level: Second
- Area: 260 Square Feet
- Dimensions: 26x10
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
- Laundry: Laundry Room
Features
- Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Solid Wood Cabinets, Split Bedroom, Stone Counters, Tray Ceiling(s), Walk-In Closet(s), Wet Bar
- Flooring: Carpet, Ceramic Tile, Hardwood
- Has fireplace: Yes
- Fireplace features: Family Room, Gas, Master Bedroom, Wood Burning
Interior area
- Total structure area: 7,014
- Total interior livable area: 5,780 sqft
Property
Parking
- Total spaces: 3
- Parking features: Garage - Attached
- Attached garage spaces: 3
Features
- Levels: Two
- Stories: 2
- Exterior features: Garden, Irrigation System, Lighting, Private Mailbox, Private Yard, Rain Gutters
Lot
- Size: 0.59 Acres
- Dimensions: 72 x 270 x 160 x 201
Details
- Parcel number: 182330603100170
- Zoning: R-1-AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1995
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Public
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: OAK ISLAND REP 02
HOA
- Has HOA: Yes
- HOA fee: $170 monthly
- HOA name: Lauren Waite
- HOA phone: 407-982-3119
Location
- Region: Belle Isle
Financial & listing details
- Price per square foot: $346/sqft
- Tax assessed value: $1,042,541
- Annual tax amount: $445
- Date on market: 5/26/2026
- Cumulative days on market: 28 days
- Ownership: Fee Simple
- Total actual rent: 0
- Road surface type: Asphalt
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/26/2026 | Listed for sale | $1,999,000+177.6%$346/sqft |
Source:  Stellar MLS #O6408105 Report a problem | ||
| 7/16/2013 | Sold | $720,000-4%$125/sqft |
Source: Public Record Report a problem | ||
| 1/26/2013 | Price change | $750,000+11.1%$130/sqft |
Source: Regal Real Estate Professionals #O5140065 Report a problem | ||
| 12/31/2012 | Listed for sale | $675,000$117/sqft |
Source: RE/MAX 200 REALTY #O5108248 Report a problem | ||
| 8/2/2012 | Listing removed | $675,000$117/sqft |
Source: RE/MAX 200 Realty #O5108248 Report a problem | ||
| 7/31/2012 | Price change | $675,000-6.9%$117/sqft |
Source: RE/MAX 200 Realty #O5108248 Report a problem | ||
| 7/13/2012 | Price change | $725,000-9.3%$125/sqft |
Source: RE/MAX 200 Realty #O5108248 Report a problem | ||
| 7/1/2012 | Listed for sale | $799,000$138/sqft |
Source: RE/MAX 200 Realty #O5108248 Report a problem | ||
| 2/21/2012 | Listing removed | $799,000$138/sqft |
Source: Kelly Price & Company #O4990939 Report a problem | ||
| 11/9/2011 | Price change | $799,000-8.7%$138/sqft |
Source: Kelly Price & Company #O4990939 Report a problem | ||
| 7/14/2011 | Price change | $875,000-2.7%$151/sqft |
Source: Kelly Price & Company #O4990939 Report a problem | ||
| 6/7/2011 | Listed for sale | $899,000-5.3%$156/sqft |
Source: Kelly Price & Company #O4990939 Report a problem | ||
| 9/23/2010 | Listing removed | $949,000$164/sqft |
Source: Kelly Price & Company #O4990939 Report a problem | ||
| 7/15/2010 | Listed for sale | $949,000+80.8%$164/sqft |
Source: Kelly Price & Company #O4990939 Report a problem | ||
| 10/1/1998 | Sold | $525,000$91/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $11,214 +3.4% | $700,609 +3% |
| 2023 | $10,846 +4% | $680,203 +3% |
| 2022 | $10,430 +1.5% | $660,391 +3% |
| 2021 | $10,271 +0.8% | $641,156 +1.4% |
| 2020 | $10,190 +1% | $632,304 +2.3% |
| 2019 | $10,090 +0.9% | $618,088 +1.9% |
| 2018 | $10,003 | $606,563 -5.1% |
| 2017 | $10,003 +1.6% | $638,901 +4.8% |
| 2016 | $9,848 +0.2% | $609,855 -0.4% |
| 2015 | $9,832 -1.7% | $612,004 +4% |
| 2014 | $10,002 -4.9% | $588,596 -4.7% |
| 2013 | $10,520 +1.1% | $617,385 -0.6% |
| 2012 | $10,404 +3% | $620,826 -10.4% |
| 2011 | $10,105 +4.8% | $693,035 +23.1% |
| 2010 | $9,642 | $562,864 -6.7% |
| 2009 | -- | $603,172 -26.9% |
| 2008 | $8,485 +1.4% | $825,191 -2.5% |
| 2007 | $8,368 -4.5% | $846,239 +24.3% |
| 2006 | $8,758 -0.2% | $680,997 +15.7% |
| 2005 | $8,779 +5% | $588,692 +13.9% |
| 2004 | $8,361 +2.9% | $516,913 +6.1% |
| 2003 | $8,127 +7.8% | $487,063 +10.3% |
| 2002 | $7,540 +2.1% | $441,458 +5.5% |
| 2001 | $7,382 +6.7% | $418,600 +8.6% |
| 2000 | $6,921 | $385,618 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 32809
Nearby schools
GreatSchools rating
- 7/10Pershing Elementary SchoolGrades: K-8Distance: 0.7 mi
- 3/10Oak Ridge High SchoolGrades: 9-12Distance: 2.5 mi
Schools provided by the listing agent
- Elementary: Pershing Elem
- Middle: PERSHING K-8
- High: Oak Ridge High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Orange County
- Belle Isle
- 32809
- 5009 Pleasure Island Rd
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