5050 Isleworth Country Club Dr, photo 1
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Overview

4 bd5 ba3,365 sqft2 car garageSingle Family
TypeSingle Family
HOA$3,672/qtr
Built1987
Lot22,514 sqft
Living area3,365 sqft
Price / sqft$948
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Built-in FeaturesCentral VaccumEat-in KitchenHigh CeilingsKitchen/Family Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsStone Counters

5050 Isleworth Country Club Dr is a 1987-built home in Isleworth, Windermere. Inside you'll find 4 bedrooms, 5 bathrooms, and 3,365 square feet of living space. Listed at $3,189,000 (about $948/sqft), 47 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $3,672 quarterly.

From the listing

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.

The essentials

Built
1987
Price / sqft
$948
On market
47 days
Annual tax
$28,793
HOA
$3,672/qtr
Flood zone
X · Low risk
Lot
22,514 sqft
Type
Single Family Residence

At a glance

Single family
Built 1987
Private pool
Gunite
2 car garage
Circular Driveway
0.52 acres
Lot size
3,365 sqft
Living area

Payment

Est. monthly payment
$21,850/mo
Down payment (20%)
$637,800
Property taxes
$2,399/mo
HOA
$3,672/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1987
Lot
22,514 sqft
Cooling
Central Air, Zoned
Heating
Central, Electric, Zoned
Parking
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Pool
Gunite, Tile
Days on Market
47
Built-in Features
Central Vaccum
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Solid Wood Cabinets
Stone Counters
Walk-in Closet(s)
Window Treatments
Lighting
Rain Gutters
Sprinkler Metered
Association Recreation - Owned
Clubhouse
Community Mailbox
Fitness Center
Gated Community - Guard
Golf Carts OK
Golf
Irrigation-reclaimed Water
Playground
Pool
Restaurant
Special Community Restrictions
Tennis Court(s)
Street Lights
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
Range Hood
Refrigerator
Tankless Water Heater
Washer
Water Softener
Wine Refrigerator
Elementary
Windermere Elem
Middle
Chain of Lakes Middle
High
Olympia High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2025)
$28,793
Parcel #
16-23-28-3899-00-410

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Isleworth
County
Orange
MLS Area
34786 - Windermere
Lot Size
22,514 sqft
In CountyLandscapedOn Golf CoursePavedPrivate
HOA
$3,672/qtr
Dan O'Connell

Price history

Date
Event
Price
8/28/2026
Listed for sale
Source: Stellar MLS #O6438618
$3,189,000
$948/sqft

Neighborhood

5050 Isleworth Country Club Dr
Windermere, FL, 34786 · 34786 - Windermere

Market insights

Offer Insights

Choose an offer strength

List price: $3,189,000
$3.14M – $3.19M
98.4% – 100% of listTops out right at the list price
80% of listList price
152 of the last 302 home closings in 34786 landed at this number or higher (50%). The median one sat 31 days before it went under contract, and this one is on day 47.

Sample: 302 closed home sales in 34786 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$21,850/mo
Principal & interest$16,632
Property taxes$2,399
Insurance$1,595
HOA$1,224
Down payment20% · $637,800
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$3,189,000

$948 per sq ft

Beds and baths

4 beds, 5 baths

Size

3,365 sq ft

Time on market

47 days

Year built

1987

Monthly payment

About $21,850/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $28,793 annual tax bill, insurance, and the $3,672/qtr HOA fee.

HOA fee

$3,672/qtr

Managed by Dan O'Connell.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byCOMPASS FLORIDA LLCListing agent: Toni CaffertyListing data from Stellar MLS, MLS# O6438618.

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