$3,390,000

5050 Isleworth Country Club Drive

Windermere, FL 34786

Active
4
Beds
5
Baths
3,365
Sq Ft
0.52
Acres
1987
Built
Private poolFireplace$1,007/sqft
🏠Single Family Residence

Property type

🏗️1987

Year built

📐22,514 sqft

Lot size

📊$1,007

Price / sq ft

🏘️$1,043/mo

HOA dues

📅46

Days on market

🚗2

Garage spaces

🌊X

Flood zone

About this home

Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in the heart of Windermere, Florida. The foyer with groin ceiling is light and bright as natural light floods into the home from the glass entryway. Arched details abound in the entrance and this staple in Mediterranean design is carried throughout the estate. Two steps down into the sunken formal living room, the gas fireplace is the centerpiece featuring an artistic stone slab above the hearth and framed by wall-to-wall stacked stone. Completing the space are four large arched windows, two arched doors providing access to the back garden and a built-in dry bar. Situated between the family room and formal living room, and serviced by the nearby kitchen, the formal dining room offers the same illumination of natural sunlight from two large arched windows. The kitchen features new KitchenAid stainless steel appliances, a NXR Pro gas range and built-in 40 bottle Euro Cave wine fridge. The custom cabinetry provides ample storage and tastefully pairs in a dark grey-brown tone with the white tile backsplash, multi-tonal grey to white tile range hood and marble counters with soft neutral veins. The custom cabinetry continues seamlessly into the family room with built-in entertainment center. Down the hall from the kitchen and family room are the guest rooms. The first features an ensuite bathroom and the other two bedrooms are serviced by the hall bath with dual sinks. The hall bath also provides access to the patio and serves as the pool bath. Situated on the opposite end of the home, we find the primary suite, powder bath off the foyer and a flex room. The primary is airy and bright with arched windows, stacked stone fireplace and a dazzling chandelier. The suite features two separate bathrooms – one with walk-in shower and the second with free-standing soaking tub. The walk-in closet offers a warm cedar wood ceiling and custom built-ins. The flex room proposes many uses whether it be an office, nursery, gym, den or library. This stunning property offers a seamless blend of indoor-outdoor living boasting a covered patio with fireplace, open-air pool with spa and views of the fairway. Rounding out the estate is a welcoming circular driveway that extends to the rear motor court with two-car garage plus golf cart parking. Whether hosting or unwinding, this home elevates every moment.

Estimated monthly payment

Principal & interest$17,142
Property taxes$2,399
Home insurance (est.)$1,554
HOA dues$1,043

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history46 days on market

  1. Status: Active
    Jan 10, 2026
  2. Listed$3,975,000
    Jan 10, 2026
  3. Price reduced$3,390,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
46
Subdivision
Isleworth
County
Orange
Year built
1987
Living area
3,365 sq ft
Price/sq ft
$1,007
Building area
4,843 sq ft (Public Records)
Lot size
22,514 sq ft
Lot category
1/2 to less than 1
Flood zone
X
Garage
2 spaces
Pool
Private pool
Annual taxes
$28,793 (2025)
Parcel #
16-23-28-3899-00-410
Zoning
P-D
MLS #
O6372348

Interior Details

Bedrooms
4
Full bathrooms
4
Half bathrooms
1
Flooring
Tile
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Interior features
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
Laundry
Inside, Laundry Room
Stories / Levels
One
Direction faces
Southeast
Fireplace
Yes

Heating & Cooling

Heating
Central, Electric, Zoned
Cooling
Central Air, Zoned

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Golf Cart Parking, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Oversized

HOA & Financial

HOA fee
$3,129 / Quarterly
Monthly HOA
$1,043/mo
Total monthly fees
$1,043/mo
Total annual fees
$12,516
HOA name
Dan O'Connell
CDD
No
Min lease term
7 Months
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Per Isleworth Community Association (ICA)
Approval process
Per Isleworth Community Association (ICA)

Exterior & Construction

Exterior features
Lighting, Rain Gutters, Sliding Doors, Sprinkler Metered
Construction materials
Block, Stucco
Roof
Tile, Concrete
Foundation
Block
Pool
Private pool
Road surface
Asphalt

Utilities

Sewer
Septic Tank
Water source
Public
Utilities
BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Underground Utilities, Water Connected

Community

Pets allowed
Breed Restrictions, Cats OK, Dogs OK, Yes

Schools

ElementaryAWindermere ElemGreatSchools ↗
MiddleCChain of Lakes MiddleGreatSchools ↗
High SchoolAOlympia HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
LaundryFirst6x12
Bedroom 4First12x12
Bathroom 4First6x13
Bedroom 3First13x11
Bedroom 2First12x11
Primary BathroomFirst
Primary BedroomFirst20x20
Bathroom 1First5x7
DenFirst16x7
Family RoomFirst13x23
KitchenFirst13x23
Dining RoomFirst12x16
Living RoomFirst19x17

Listing Details

Listing date
2026-01-03
On market date
2026-01-10
Original list price
$3,975,000
Occupant type
Owner
MLS area
34786 - Windermere
Listing AOR
Orlando Regional
Status changed
2026-01-10
Tax legal description
ISLEWORTH 16/118 LOT 41

Flood risk

Minimal riskFEMA Zone X

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

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.

Based on information submitted to the MLS GRID as of February 25, 2026 at 5:46 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA