
5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL, 34786
Active16 days on marketListed Sep 4, 2026MLS #O6438618
About this home
5050 ISLEWORTH COUNTRY CLUB DRIVE
Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.
Facts & features
The home at a glance
4
Bedrooms
4.5
Bathrooms
3,365
Sqft
0.52 ac
Lot size
2
Garage
1987
Year built
One
Levels
$948
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.
$22,187 /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
$22,187/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
+156.3%
$/sqft vs ISLEWORTH
$948 vs $954
Days on market
16 vs 48 typical
Where $948/sqft sits among the 18 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 → $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 369% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 5050 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 · May ’26$4,287,500
6113 PAYNE STEWART DRIVE · same community
3 bd · 3.5 ba · 2,983 sqft · $1,437/sqft · 30 DOM
Sold · Feb ’26$2,950,000
4711 JOANNA GARDEN CT · same community
3 bd · 3.5 ba · 4,089 sqft · $721/sqft · 60 DOM
Sold · Sep ’25$2,500,000
5138 FAIRWAY OAKS DRIVE · same community
4 bd · 4.5 ba · 4,330 sqft · $577/sqft · 159 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
Jillian Kobylesky
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5050 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 5050 ISLEWORTH COUNTRY CLUB DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Jillian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
5050 ISLEWORTH COUNTRY CLUB DRIVE FAQs
What would the monthly payment be for 5050 ISLEWORTH COUNTRY CLUB DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $22,187/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 5050 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 5050 ISLEWORTH COUNTRY CLUB DRIVE?+
The most recent tax bill on record (2025) was $28,793. 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 5050 ISLEWORTH COUNTRY CLUB DRIVE?+
The listing reports pets: Breed Restrictions, Cats OK, Dogs OK, 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 $3,189,000, this home is listed about 193% 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 5050 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
$3,189,000 runs 369% above the WINDERMERE 34786 median.
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.
Keep looking
Similar homes nearby
Listing courtesy of COMPASS FLORIDA LLC · Toni Cafferty. MLS #O6438618.
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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