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Street View
$3,189,000
Monthly Est:$15,873
4 Beds
- 5 Baths
4 full baths + 1 half bath
3,365sqft
5050 Isleworth Country Clb Dr, Windermere, FL 34786
$3,189,000
$15,873/moEst:
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Single Family Residence
Built in 1987
$1,224/mo HOA
22,514 sqft lot
$948/sq.ft
Description
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.
- Houzeo last checked: 2 hours ago
- Listing updated: September 5, 2026 at 10:48 am
- Listing Provided by: Toni Cafferty (904) 449-2184 | COMPASS FLORIDA LLC (407) 203-9441
- Source: Stellar MLS-FL | MLS#: O6438618

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1987
HOA Fees
$1224/mo
Finished Area
3,365 sqft
Lot Size
22,514 sqft lot
Basement Area
- sqft
MLS Name
Stellar MLS
MLS Number
O6438618
MLS Status
Active
Days on Market
54
Cumulative Days on Market
1

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Location
HOA Management
Dan O'Connell
HOA Fees
$3,672/ Quarterly
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Maintenance
Security Gate
Basket Ball
Cable TV
Security Guard
Park Playground
Private Road
Escrow Reserves Fund
Optional Additional Fees
Vehicle Restrictions
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 5
Living Room
Level: First
Area: 323.00 Square Feet
Dimensions: 19x17
Dining Room
Level: First
Area: 192.00 Square Feet
Dimensions: 12x16
Kitchen
Level: First
Area: 299.00 Square Feet
Dimensions: 13x23
Family Room
Level: First
Area: 299.00 Square Feet
Dimensions: 13x23
Den
Level: First
Area: 112.00 Square Feet
Dimensions: 16x7
Bathroom 1
Level: First
Area: 35.00 Square Feet
Dimensions: 5x7
Primary Bedroom
Level: First
Area: 400.00 Square Feet
Dimensions: 20x20
Primary Bathroom
Level: First
Bedroom 2
Level: First
Area: 132.00 Square Feet
Dimensions: 12x11
Bedroom 3
Level: First
Area: 143.00 Square Feet
Dimensions: 13x11
Bathroom 4
Level: First
Area: 78.00 Square Feet
Dimensions: 6x13
Bedroom 4
Level: First
Area: 144.00 Square Feet
Dimensions: 12x12
Laundry
Level: First
Area: 72.00 Square Feet
Dimensions: 6x12
Interior
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Window Features
Blinds, Drapes, Rods, Shades, Tinted Windows
Heating
Central, Electric, Zoned
Flooring
Tile
Exterior Features
Lighting, Rain Gutters, Sprinkler Metered
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
Cooling
Central Air, Zoned
Sewer
Septic Tank
Construction
Year Built
Year Built: 1987
Home type
Single Family Residence
Foundation Details
Block
Roof
Concrete, Tile
Construction Materials
Block, Stucco
Utilities & Energy
Pool Features
Gunite, Tile
Association Amenities
Basketball Court, Cable Tv, Fence Restrictions, Gated, Optional Additional Fees, Playground, Security, Vehicle Restrictions
Water Source
Public
Security Features
Gated Community
Fireplace Features
Living Room, Outside, Primary Bedroom
Parking Features
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
Utilities
Bb/hs Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Public, Sprinkler Meter, Underground Utilities, Water Connected
Laundry Features
Inside, Laundry Room
Other Features
Subdivision Name
Isleworth
Patio And Porch Features
Covered, Rear Porch
Lot Features
In County, Landscaped, On Golf Course, Paved, Private
Vegetation
Mature Landscaping, Oak Trees
Community Features
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
Price History
| Date | Event | Price |
|---|---|---|
09/04/2026 Source: #MFRO6438618 | Listed for Sale | $3,189,000 -5.93% $948/sqft |
07/05/2026 Source: | Listing Removed | $3,390,000 $1,007/sqft |
02/25/2026 Source: | Price Decreased | $3,390,000 -8.13% $1,007/sqft |
01/24/2026 Source: | Price Decreased | $3,690,000 -7.17% $1,097/sqft |
01/10/2026 Source: | Price Increased | $3,975,000 +17.26% $1,181/sqft |
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Based on information from Stellar MLS® through Oct 28, 2026, 02:15PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.
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