111 Windy Point Circle, MARATHON, FL

$3,400,000

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3

Beds

4

Baths

2,446

Square feet

37,897

Land Size

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

AgentAlly Kelley
OfficeOcean Sotheby's International

Listing Map

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