111 Windy Point Circle, Marathon, FL 33050

$2,900,000
Property Type: Residential Bedrooms: 3 Baths: 4 Square Footage: 2,446 Lot Size (sq. ft.): 37,897 Status: Active
Current Price: $2,900,000 List Date: 12/02/2025 Last Modified: 2/12/2026

Description

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.

More Information MLS# 617541

Contract Information

Current Price: $2,900,000 Listing Date: 2025-12-02 Listing Board: Marathon/Lower Keys List Price: $2,900,000 As is Rght to Inspct: Yes Species List: No

Location Tax Legal

Street #: 111 Street Name: Windy Point Street Suffix: Circle Key/Island: Marathon State/Province: FL Zip Code: 33050 County: Monroe Subdivision: Stirrup Key Sub (52.5) Area: 15 - Sombrero Bch Rd to Vaca Cut Gulfside

General Property Description

Realtor.COM Type: Residential - Single Family Style: Single Family Waterfront: Yes Control Depth: 4 Pool: Yes Year Built: 1988 Lot SqFt: 37897 Lot Sqft Source: Property Data Card Acres: 0.87 Living Apx SqFt: 2446 SqFt Source: Property Data Card Total Bedrooms: 3 Full Baths: 2 Half Baths: 2 Total Baths: 4 Rentals Allowed: With Restrictions Min Rental Days: 365

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: Yes 1st Right of Refusal: No Association Fee $: 2550 Assoc/Mnt Fee Per: Yearly

Building Style

Above Flood: Yes Stories: 2 Stories

Vehicle Storage

Car(s): 4+

Pool Info

Heated: Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: Bay Front; Gulf Front; Open Water Waterview: Bay/Gulf View; Open Water View Dockage: Basin; Boat Slip Vehicle Storage: Garage; Auto Door Opener; Covered Parking; Guest Parking; Off Street Parking; Open Parking; RV Parking Covered; RV Parking Open; Trailer Storage Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air Heating: Central Utilities: Cable Available; Elect Separate Meter; FKAA; Municipal Sewer; Water Separate Meter Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Elevator; Entrance Foyer; Fireplace(s); Smoke Alarms; Storage; Whirlpool Bath Tub; Window Treatments Pre-Wired: Cable Specialty Rooms: Utility Room; Workshop Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Refrigerator; Washer Exterior Features: Chickee Hut; Fruit Tree(s); Lighting; Storage Pool Info: In Ground; Concrete; Decked; Screened In Construction: CBS; Concrete Shutters: Accordion; Bahama Floor: Tile Roof: Tile Roof Pets: Pets Allowed Neighborhood Feature: Community Boat Ramp Security: Electric Gate; Patrolled Area Land Size: 1/2 - Less Than 1 AC Terms: Cash; Conventional
Listing Office: Ocean Sotheby's International Realty
Last Updated: February - 12 - 2026
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