About 111 Windy Point Circle
Embrace the rare opportunity to own .87 acres of open-water paradise in the prestigious, gated community of Stirrup Key. Over 300 feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Three protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary. This can also be sold with the buildable Lot 78 next door, which is 38,333 sf and offered for $2,200,000 to create a 1.75 acre compound.
Features of 111 Windy Point Circle
| MLS® # | 617541 |
|---|---|
| Price | $3,400,000 |
| Bedrooms | 3 |
| Bathrooms | 4.00 |
| Full Baths | 2 |
| Half Baths | 2 |
| Square Footage | 2,446 |
| Land Size | 37,897 |
| Year Built | 1988 |
| Type | Residential |
| Sub-Type | Single Family |
| Status | Active |
Community Information
| Address | 111 Windy Point Circle |
|---|---|
| Area | 15 - Sombrero Bch Rd to Vaca Cut Gulfside |
| Subdivision | Stirrup Key Sub (52.5) |
| City | MARATHON |
| County | Monroe |
| State | FL |
| Zip Code | 33050 |
Amenities
| Amenities | Community Boat Ramp |
|---|---|
| Utilities | FKAA, Water Separate Meter, Cable Available, Elect Separate Meter, Municipal Sewer |
| Parking Spaces | 4 |
| Parking | Garage, Trailer Storage, Covered Parking, RV Parking Covered, RV Parking Open, Off Street Parking, Guest Parking, Open Parking, Auto Door Opener |
| View | Bay/Gulf View, Open Water View |
| Is Waterfront | Yes |
| Waterfront | Bay Front, Open Water, Gulf Front |
| Has Pool | Yes |
| Pool | In Ground, Screened In, Decked, Concrete |
Interior
| Interior Features | Drapes/Blinds Incl, Built-in Cabinets, Window Treatments, Whirlpool Bath Tub, Storage, Smoke Alarms, Elevator, Entrance Foyer, Fireplace(s) |
|---|---|
| Appliances | Washer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer |
| Heating | Central |
| Cooling | Central Air, Ceiling Fans(s) |
| Fireplace | Yes |
| Stories | 2 Stories |
Exterior
| Exterior Features | Chickee Hut, Storage, Lighting, Fruit Tree(s) |
|---|---|
| Lot Description | 1/2 - Less Than 1 AC |
| Windows | Sliding Glass Doors, Casement |
| Roof | Tile Roof |
| Construction | CBS, Concrete |
| Neighborhood Features | Community Boat Ramp |
Additional Information
| Date Listed | December 2nd, 2025 |
|---|---|
| Days on Market | 4 |
| Zoning | RM - Residential Medium |
| Short Sale | No |
| RE / Bank Owned | No |
| HOA Fees | 2550.00 |
| HOA Fees Freq. | Yearly |
Listing Details
| Agent | Ally Kelley |
|---|---|
| Office | Ocean Sotheby's International |
