5009 PLEASURE ISLAND ROAD, BELLE ISLE, FL, 32809
Active76 days on marketListed May 26, 2026MLS #O6408105
About this home
5009 PLEASURE ISLAND ROAD
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.
Facts & features
The home at a glance
4
Bedrooms
4.5
Bathrooms
5,780
Sqft
0.59 ac
Lot size
3
Garage
1995
Year built
Two
Levels
$329
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$11,326 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$11,326/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Belle Isle actives
$329 vs $266
Days on market
76 vs 87 typical
Where $329/sqft sits among the 8 Belle Isle actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Belle Isle
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Belle Isle. See the full Belle Isle guide →
BELLE ISLE 32809 — neighborhood snapshot
Population
29,379
Median age
36.6
Median income
$52,203
Median home value
$281,000
Avg household
3.08
Households w/ children
3,945
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Belle Isle market
$630K → $665K
Belle Isle median sold, yr/yr
96.9%
Sale-to-list ratio (12 mo)
6 of 8
Belle Isle actives have cut their price
Median sold price, Belle Isle, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 985% above the BELLE ISLE 32809 median. See the full Belle Isle market guide →
Paper trail
This home's history
Reality check
What actually sold near 5009 PLEASURE ISLAND ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$960,000
1448 CONWAY ISLE CIRCLE
4 bd · 4.5 ba · 4,367 sqft · $220/sqft · 118 DOM
Sold · Feb ’26$965,000
1610 CONWAY ISLE CIRCLE
5 bd · 5 ba · 3,796 sqft · $254/sqft · 8 DOM
Sold · Aug ’25$985,000
4221 ISLE VISTA AVENUE
4 bd · 4 ba · 3,685 sqft · $267/sqft · 17 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5009 PLEASURE ISLAND ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5009 PLEASURE ISLAND ROAD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
5009 PLEASURE ISLAND ROAD FAQs
What would the monthly payment be for 5009 PLEASURE ISLAND ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $11,326/mo — principal and interest, the actual property-tax bill, the $170/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 5009 PLEASURE ISLAND ROAD?+
The association fee works out to $170 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5009 PLEASURE ISLAND ROAD?+
The most recent tax bill on record (2025) was $445. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5009 PLEASURE ISLAND ROAD?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Belle Isle?+
At $1,899,000, this home is listed about 245% above the Belle Isle median of $550,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5009 PLEASURE ISLAND ROAD?+
Oak Ridge High (high), Lancaster Elementary (elementary), Judson B Walker Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
Listing courtesy of ONE LUXURY INTERNATIONAL LLC · Christopher Christensen. MLS #O6408105.
IDX information is provided exclusively 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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