5092 Isleworth Country Club Dr, photo 1
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Overview

4 bd5 ba7,100 sqft4 car garageSingle Family
TypeSingle Family
HOA$3,672/qtr
Built1995
Lot40,620 sqft
Living area7,100 sqft
Price / sqft$1,197
Garage4 car

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

About this home

Built-in FeaturesCathedral Ceiling(s)Ceiling Fans(s)Central VaccumCrown MoldingEat-in KitchenHigh CeilingsKitchen/Family Room Combo

5092 Isleworth Country Club Dr is a 1995-built home in Isleworth, Windermere. Inside you'll find 4 bedrooms, 5 bathrooms, and 7,100 square feet of living space. Listed at $8,500,000 (about $1,197/sqft), 14 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $3,672 quarterly.

From the listing

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.

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The essentials

Built
1995
Price / sqft
$1,197
On market
14 days
Annual tax
$57,071
HOA
$3,672/qtr
Flood zone
X · Low risk
Lot
40,620 sqft
Type
Single Family Residence

At a glance

Single family
Built 1995
Water views
Garden
Private pool
In Ground
4 car garage
Circular Driveway
0.93 acres
Lot size

Payment

Est. monthly payment
$54,561/mo
Down payment (20%)
$1,700,000
Property taxes
$4,756/mo
HOA
$3,672/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1995
Lot
40,620 sqft
Cooling
Central Air, Zoned
Heating
Central, Zoned
Parking
Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Pool
In Ground, Lighting
Days on Market
14
Built-in Features
Cathedral Ceiling(s)
Ceiling Fans(s)
Central Vaccum
Crown Molding
Eat-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
Balcony
Lighting
Outdoor Grill
Outdoor Shower
Rain Gutters
Association Recreation - Owned
Community Mailbox
Fitness Center
Golf Carts OK
Golf
Playground
Pool
Tennis Court(s)
Street Lights
Bar 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
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.

Homestead exemption on file Flood Zone X
Annual Tax (2026)
$57,071
Parcel #
16-23-28-3899-00-480

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
40,620 sqft
LandscapedOn Golf CourseOversized LotPavedPrivate
HOA
$3,672/qtr
Dan O’Connell

Price history

Date
Event
Price
10/1/2026
Listed for sale
Source: Stellar MLS #O6446272
$8,500,000
$1,197/sqft

Neighborhood

5092 Isleworth Country Club Dr
Windermere, FL, 34786 · 34786 - Windermere

Market insights

Offer Insights

Choose an offer strength

List price: $8,500,000
$8.37M – $8.50M
98.5% – 100% of listTops out right at the list price
80% of listList price
154 of the last 307 home closings in 34786 landed at this number or higher (50%). The median one sat 30 days before it went under contract, and this one is on day 14.

Sample: 307 closed home sales in 34786 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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Calculator

Est. monthly payment
$54,561/mo
Principal & interest$44,331
Property taxes$4,756
Insurance$4,250
HOA$1,224
Down payment20% · $1,700,000
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

$8,500,000

$1,197 per sq ft

Beds and baths

4 beds, 5 baths

Size

7,100 sq ft

Time on market

14 days

Year built

1995

Monthly payment

About $54,561/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $57,071 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 byISLEWORTH REALTY LLCListing agent: Michelle CorbinListing data from Stellar MLS, MLS# O6446272.

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