$3,600,000
5237 Isleworth Country Club DriveWindermere, FL 34786
Listing updated: October 28, 2026 at 6:52 AM ET
Listing courtesy of Isleworth Realty Llc · Monica Lochmandy · MLS #O6427447 · Active · 407-909-9000Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Garage spaces
Flood zone
About this home
Located along the 2nd tee of Isleworth's renowned championship golf course, this beautiful golf-front estate offers an exceptional location within the gates. The five-bedroom home features offers a spacious and open floor plan of more than 5,900 square feet overlooking the serene golf and water vistas. .
Estimated monthly payment
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 history1 days on market
- Status: ActiveOct 27, 2026
- Listed$3,600,000Jul 30, 2026
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 1
- Subdivision
- Isleworth
- County
- Orange
- Year built
- 1989
- Living area
- 5,972 sq ft
- Price/sq ft
- $603
- Building area
- 8,281 sq ft (Public Records)
- Lot size
- 22,076 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- AE (12095C0385F)
- Garage
- 3 spaces
- Pool
- Private pool
- Annual taxes
- $45,808 (2025)
- Parcel #
- 16-23-28-3899-02-320
- Zoning
- P-D
- MLS #
- O6427447
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Interior Details
- Bedrooms
- 5
- Full bathrooms
- 5
- Flooring
- Carpet, Marble, Wood
- Appliances
- Built-In Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Interior features
- Built-in Features, Primary Bedroom Main Floor, Walk-In Closet(s)
- Laundry
- Inside
- Stories / Levels
- Two
- Direction faces
- Northwest
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central, Zoned
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 3
- Attached garage
- Yes
HOA & Financial
- HOA fee
- $3,672 / Quarterly
- Monthly HOA
- $1,224/mo
- Total monthly fees
- $1,224/mo
- Total annual fees
- $14,688
- HOA name
- Dan O'Connell
- CDD
- No
- Min lease term
- 8-12 Months
- Listing terms
- Cash
- 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
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Block, Slab
- Pool
- Private pool
- Water access
- Yes
- Water view
- Yes
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Well
- Utilities
- Cable Connected, Electricity Connected, Public
Community
- Pets allowed
- Breed Restrictions, Yes
Schools
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
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | ||
| Family Room | ||
| Living Room | ||
| Dining Room | ||
| Primary Bedroom | ||
| Office |
Listing Details
- Listing date
- 2026-07-29
- On market date
- 2026-07-30
- Original list price
- $3,600,000
- Occupant type
- Vacant
- MLS area
- 34786 - Windermere
- Listing AOR
- Orlando Regional
- Status changed
- 2026-10-27
- Tax legal description
- ISLEWORTH 16/118 LOT 232
Flood risk
FEMA Special Flood Hazard Area (1% annual-chance / “100-year” floodplain). Flood insurance is generally required by mortgage lenders.
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. Stay straight on Isleworth Country Club Drive. Estate will be on the Left or Right.
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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 October 28, 2026 at 6:52 AM 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.
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