CENTURY 21 Edge
$7,200,0005 bd5.5 ba5,993 sqft$1,201 /sqft$46,561 /mo all-in ↓

5373 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL, 34786

Active12 days on marketListed Sep 8, 2026MLS #O6439156

Private poolSingle Family ResidenceISLEWORTH

About this home

5373 ISLEWORTH COUNTRY CLUB DRIVE

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

Facts & features

The home at a glance

5

Bedrooms

5.5

Bathrooms

5,993

Sqft

0.52 ac

Lot size

3

Garage

1988

Year built

Two

Levels

$1,201

Per sqft

Private poolFireplaceGolf Course & Water view

Inside

FlooringEngineered Hardwood · Marble · Tile
AppliancesConvection Oven · Cooktop · Dishwasher · Dryer · Ice Maker · Microwave · Refrigerator · Tankless Water Heater · Washer
InteriorBuilt-in Features · Cathedral Ceiling(s) · Eating Space In Kitchen · High Ceilings · Kitchen/Family Room Combo · Open Floorplan · Primary Bedroom Main Floor · Solid Surface Counters · Split Bedroom · Tray Ceiling(s)
LaundryInside · Laundry Room
CoolingCentral Air · Zoned
HeatingCentral · Electric · Zoned

Outside & construction

RoofTile
ConstructionBlock · Concrete · Stucco
FoundationBlock · Slab
ViewGolf Course · Water
FacesNorth
ParkingCircular Driveway · Garage Door Opener · Garage Faces Side · Parking Pad
ExteriorIrrigation System · Outdoor Kitchen · Rain Gutters

Community & fees

HOA fee$1,224/mo
Taxes (2025)$43,509/yr
PetsBreed Restrictions
CommunityCommunity Boat Ramp · Lake · Private Boat Ramp · Water Access · Buyer Approval Required · Community Mailbox · Gated Community - Guard · Golf Carts OK · Golf · Park · Playground

Utilities & systems

UtilitiesCable Connected · Electricity Connected · Natural Gas Connected · 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.

$46,561 /mo · 10% down Conventional, 30-yr fixed at 6%

Principal & interest$38,851
PMI (est., until 20% equity)$2,700
Property tax — 2025 actual bill$3,626
HOA fee — from the listing$1,224
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $720,000Loan30-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% · $720,000
Interest rate6.00%
Loan term

Estimated payment

$46,561/mo

Principal & interest$38,851
PMI (est., until 20% equity)$2,700
Property taxes (actual bill)$3,626
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 $7.2M
$2.2MedgeAI estimate $2,322,397 · range $2.2M$2.5M$7.5M

vs edgeAI estimate

+210%

$/sqft vs ISLEWORTH

$1,201 vs $948

Days on market

12 vs 48 typical

Where $1,201/sqft sits among the 18 homes for sale in ISLEWORTH

1
3
3
4
2
5 · this home
$456–584$584–712$712–839$839–967$967–1095$1095+

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 Orlando16 min
Walt Disney World23 min
Downtown Orlando24 min
Orlando Int’l Airport (MCO)37 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★★★★
HighOlympia High★★★★★
ElementaryWindermere Elementary★★★★★

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

The numbers that matter

The Windermere market

Seller’s marketLeans seller4.0 months of inventoryBuyer’s market

$875K$840K

Windermere median sold, yr/yr

96.5%

Sale-to-list ratio (12 mo)

10 of 18

ISLEWORTH have cut their price

Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.

This home is listed 959% above the WINDERMERE 34786 median. See the full Windermere market guide →

Paper trail

This home's history

Sep 8, 2026Listed at $7,200,000 · 12 days on market since
1988Built · ISLEWORTH

Reality check

What actually sold near 5373 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.

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

5067 LATROBE DRIVESold · Oct ’25

$2,750,000

5067 LATROBE DRIVE · same community

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

Tommy Trainer

Your agent

Tommy Trainer

Real Estate Agent · CENTURY 21 Edge

Tours, negotiation, and every question about 5373 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 5373 ISLEWORTH COUNTRY CLUB DRIVE — before you fall in love.

See it in person

Schedule a tour

Live availability from Tommy's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.

Straight answers

5373 ISLEWORTH COUNTRY CLUB DRIVE FAQs

What would the monthly payment be for 5373 ISLEWORTH COUNTRY CLUB DRIVE?+

With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $46,561/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 5373 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 5373 ISLEWORTH COUNTRY CLUB DRIVE?+

The most recent tax bill on record (2025) was $43,509. 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 5373 ISLEWORTH COUNTRY CLUB DRIVE?+

The listing reports pets: Breed Restrictions. 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 $7,200,000, this home is listed about 561% above the Windermere median of $1,089,500. The market section on this page shows how the area is trending.

Which schools are assigned to 5373 ISLEWORTH COUNTRY CLUB DRIVE?+

Chain Of Lakes Middle (middle), Olympia High (high), Windermere Elementary (elementary) — 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

$7,200,000 runs 959% above the WINDERMERE 34786 median — but at 5,993 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, Olympia High, Windermere Elementary — Windermere Elementary rates 5 of 5. Always verify assignments with the district.

Listing courtesy of STOCKWORTH REALTY GROUP · Rob Rahter. MLS #O6439156.

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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