CENTURY 21 Edge
$8,500,0004 bd5 ba7,100 sqft$1,197 /sqft≈$55,193 /mo all-in ↓

5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL, 34786

Active12 days on marketListed Oct 1, 2026MLS #O6446272

Private poolSingle Family ResidenceISLEWORTH

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

Private poolFireplaceGarden & Golf Course & Trees/Woods & Water viewNegotiablePets allowed

Inside

FlooringBrick/Stone · Carpet · Marble · Travertine · Hardwood
AppliancesBar Fridge · Built-In Oven · Convection Oven · Dishwasher · Disposal · Dryer · Electric Water Heater · Exhaust Fan · Freezer · Ice Maker · Microwave · Range · Range Hood · Refrigerator · Washer · Water Filtration System · Wine Refrigerator
InteriorBuilt-in Features · Cathedral Ceiling(s) · Ceiling Fan(s) · Central Vacuum · Crown Molding · Eating Space In Kitchen · High Ceilings · Kitchen/Family Room Combo · Primary Bedroom Main Floor · Solid Wood Cabinets · Stone Counters · Vaulted Ceiling(s) · Walk-In Closet(s) · Wet Bar · Window Treatments
LaundryLaundry Room
CoolingCentral Air · Zoned
HeatingCentral · Zoned
FurnishedNegotiable

Outside & construction

RoofTile
ConstructionBlock · Stucco
FoundationSlab
ViewGarden · Golf Course · Trees/Woods · Water
FacesEast
ParkingCircular Driveway · Garage Door Opener · Garage Faces Side · Golf Cart Garage
ExteriorBalcony · French Doors · Irrigation System · Lighting · Outdoor Grill · Outdoor Shower · Rain Gutters

Community & fees

HOA fee$1,224/mo
Taxes (2026)$57,071/yr
PetsBreed Restrictions, Yes
CommunityAssociation Recreation - Owned · Community Mailbox · Fitness Center · Golf Carts OK · Golf · Playground · Pool · Tennis Court(s)

Utilities & systems

UtilitiesCable Connected · Electricity Connected · Fire Hydrant · Natural Gas Connected · Street Lights · Underground Utilities
WaterPublic

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%

Principal & interest$45,866
PMI (est., until 20% equity)$3,188
Property tax — 2026 actual bill$4,756
HOA fee — from the listing$1,224
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $850,000Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

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

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $850,000
Interest rate6.00%
Loan term

Estimated payment

$55,193/mo

Principal & interest$45,866
PMI (est., until 20% equity)$3,188
Property taxes (actual bill)$4,756
HOA / condo fee$1,224
Est. insurance$160

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.

List $8.5M
$2.2MedgeAI estimate $2,507,466 · range $2.3M–$2.8M$8.8M

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

4
2
3
4
1
7 · this home
$583–689$689–795$795–900$900–1006$1006–1112$1112+

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

Universal Orlando≈ 11 min
Downtown Orlando≈ 19 min
Walt Disney World≈ 27 min
Orlando Int’l Airport (MCO)≈ 32 min

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

MiddleChain Of Lakes Middle★★★★★
ElementaryWindermere Elementary★★★★★
HighOlympia High★★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Windermere market

Seller’s marketLeans seller — 3.8 months of inventoryBuyer’s 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

Oct 1, 2026Listed at $8,500,000 · 12 days on market since
1995Built · ISLEWORTH

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.

5067 LATROBE DRIVESold · Oct ’25

$2,750,000

5067 LATROBE DRIVE · same community

5 bd · 7 ba · 6,219 sqft · $442/sqft · 123 DOM

9915 GIFFIN COURTSold · Nov ’25

$3,800,000

9915 GIFFIN COURT · same community

5 bd · 4 ba · 6,008 sqft · $632/sqft · 0 DOM

6474 DEACON CIRCLESold · 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.

Shawn Lewis

Your agent

Shawn Lewis

Realtor · CENTURY 21 Edge

Tours, negotiation, and every question about 5092 ISLEWORTH COUNTRY CLUB DRIVE — start here.

Andrew Acosta

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.

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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