
5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL, 34786
Active12 days on marketListed Oct 1, 2026MLS #O6446272
About this home
5092 ISLEWORTH COUNTRY CLUB DRIVE
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.
Facts & features
The home at a glance
4
Bedrooms
5
Bathrooms
7,100
Sqft
0.93 ac
Lot size
4
Garage
1995
Year built
Two
Levels
$1,197
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.
$55,193 /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
$55,193/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.
vs edgeAI estimate
+239%
$/sqft vs ISLEWORTH
$1,197 vs $927
Days on market
12 vs 80 typical
Where $1,197/sqft sits among the 21 homes for sale in ISLEWORTH
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 Isleworth
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Windermere. See the full Windermere guide →
Isleworth — neighborhood snapshot
Population
630
Median age
58
Median income
$151,250
Avg household
2
Households w/ children
56%
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Windermere market
$875K → $850K
Windermere median sold, yr/yr
96.5%
Sale-to-list ratio (12 mo)
8 of 21
ISLEWORTH have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 1134% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 5092 ISLEWORTH COUNTRY CLUB DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$2,750,000
5067 LATROBE DRIVE · same community
5 bd · 7 ba · 6,219 sqft · $442/sqft · 123 DOM
Sold · Nov ’25$3,800,000
9915 GIFFIN COURT · same community
5 bd · 4 ba · 6,008 sqft · $632/sqft · 0 DOM
Sold · Mar ’26$4,475,000
6474 DEACON CIRCLE · same community
6 bd · 5.5 ba · 5,853 sqft · $765/sqft · 0 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
Shawn Lewis
Realtor · CENTURY 21 Edge
Tours, negotiation, and every question about 5092 ISLEWORTH COUNTRY CLUB DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5092 ISLEWORTH COUNTRY CLUB DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Shawn's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
5092 ISLEWORTH COUNTRY CLUB DRIVE FAQs
What would the monthly payment be for 5092 ISLEWORTH COUNTRY CLUB DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $55,193/mo — principal and interest, the actual property-tax bill, the $1,224/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 5092 ISLEWORTH COUNTRY CLUB DRIVE?+
The association fee works out to $1,224 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5092 ISLEWORTH COUNTRY CLUB DRIVE?+
The most recent tax bill on record (2026) was $57,071. 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 5092 ISLEWORTH COUNTRY CLUB DRIVE?+
The listing reports pets: Breed Restrictions, 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 Windermere?+
At $8,500,000, this home is listed about 680% above the Windermere median of $1,090,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5092 ISLEWORTH COUNTRY CLUB DRIVE?+
Chain Of Lakes Middle (middle), Windermere Elementary (elementary), Olympia High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$8,500,000 runs 1134% above the WINDERMERE 34786 median — but at 7,100 sqft it's also nearly twice the size of the typical Windermere listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Know the monthly fee
The association fee is $1,224/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Strong assigned schools
Chain Of Lakes Middle, Windermere Elementary, Olympia High — Windermere Elementary rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of ISLEWORTH REALTY LLC · Michelle Corbin. MLS #O6446272.
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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