111 Windy Point Cir

Marathon, FL 33050

$3,400,000
Price
3
Beds
2,446 Sq. Ft.
$1,390 / Sq. Ft.
2,446
Sq. Ft.
$1,390
per Sq. Ft.
111 Windy Point Circle
an aerial view of multiple house with yard
an aerial view of a house with a ocean view
111 Windy Point Circle
an aerial view of ocean with residential house with outdoor space
a view of a garden with a building in the background
a view of a house with a yard and garden
111 Windy Point Circle
a house view with a outdoor space
a house view with a outdoor space
a view of a lake and outdoor space
111 Windy Point Circle
a view of city and ocean
a view of a lake with houses in the back
a view of a swimming pool with a patio
a view of a balcony with chairs
a garden with palm trees
a front view of a house with a garden and trees
a view of a park
111 Windy Point Circle
a row of palm trees and a backyard of a house
a house view with a outdoor space
111 Windy Point Circle
a living room with furniture and wooden floor
a living room with furniture and a large window
a room with furniture and a flat screen tv
a kitchen with granite countertop stainless steel appliances and wooden cabinets
a view of a livingroom with furniture and a dining table with chairs
111 Windy Point Circle
a spacious bedroom with a bed a couch and a window
a bedroom with a bed a couch and a window
a spacious bathroom with a double vanity sink a toilet mirror and shower
a bathroom with a sink a toilet and shower
a bedroom with a large bed and a flat tv screen on dresser
a bed room with furniture and wooden floor
a bathroom with a sink and a bathtub
a bathroom with a sink toilet and shower
a en suite bathroom with a sink a mirror and a shower
a bedroom with a bed and a large mirror
a view of a patio with table and chairs under an umbrella
111 Windy Point Circle
111 Windy Point Circle
111 Windy Point Circle
a bathroom with a sink and a mirror
a view of kitchen with refrigerator and cabinets
a bedroom with a bed and a couch
a view of a room with gym equipment
a living room with furniture and a couch
a view of a palm tree with an outdoor space
a view of a backyard
a view of a table and chairs under an umbrella in front of a house
111 Windy Point Circle
a palm tree sitting in front of a house with a yard
a view of a park with palm trees
a view of a house with a patio
a view of a balcony with city view
a view of a park with palm trees
a view of a city from a balcony
111 Windy Point Circle
a view of a lake with a building in the background
111 Windy Point Circle
a view of a pathway both side of grassy field with shrub
a view of a chairs and table in patio

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...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.
  1. Listed by Ally Kelley • Ocean Sotheby's International
  2. Listed by Jo Ann Cook • Ocean Sotheby's International

Property Details for 111 Windy Point Circle

Waterfront
Bay Front, Open Water, Gulf Front
Waterfront
Yes
Zoning
RM - Residential Medium
Subdivision
Stirrup Key Sub (52.5)
Directions
From US-1, turn onto Aviation Boulevard. Turn onto Stirrup Key Road, go through gate. Continue onto Stirrup Key Boulevard, right onto Windy Point Circle. Home will be on right.
Vehicle Storage
Garage, Trailer Storage, Covered Parking, RV Parking Covered, RV Parking Open, Off Street Parking, Guest Parking, Open Parking, Auto Door Opener
Pets
Pets Allowed
LISTING UPDATED: 12/05/2025 07:30 AM

Property Details for 111 Windy Point Circle

StatusActive
MLS #617541
Days on Market24
Taxes$28,160 / year
HOA Fees$2,550 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1988
Lot Size0.87 AC / 37,897 SF
CountyMonroe County

Location

Listing Courtesy of Ocean Sotheby's International
Add your commute

Building Information for 111 Windy Point Circle

Stories2Year Built1988Building Size-Lot Size0.87 AC / 37,897 SF

Payment Calculator

$19,360 per month

30 year fixed, 6.28% Interest

Principal and Interest

$16,801

Property Taxes

$2,347

HOA Dues

$213

The Payment Calculator is for illustrative purposes only.

Property Information for 111 Windy Point Circle

Summary
Location and General Information
  • Waterview: Bay/Gulf View, Open Water View
  • Area: 15 - Sombrero Bch Rd to Vaca Cut Gulfside
  • Absolute Longitude: 81.041663
  • Control Depth: 4
  • Off Shore Island: No
  • Listing Board: Marathon/Lower Keys
  • Side: Bay/Gulf
  • Mile Marker: 52.5
  • Marathon Neighborhood: Behind the Airport
  • Neighborhood Feature: Community Boat Ramp
  • Key/Island: Marathon
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: Yes
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Negotiable
  • Tax Year: 2024
  • Tax Exemptions: None
Virtual Tour
Property
Lot Information
  • Acres: 0.87
  • Parcel #: 00333641-007700
  • Add'l Parcel #1: 00333641-015300
  • Add'l Parcel #2: 00333641-015400&500
  • Land Size: 1/2 - Less Than 1 AC
Property and Assessments
  • Legal: LT 77 STIRRUP KEY SUBDIVISION PB7-4 STIRRUP KEY & Dock Lots 48, 49 & 50Parcels: 00333641- 015300, 015400, 015500
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Yes
  • Picture Count: 63
  • Document Count: 3
  • Building Style: Above Flood: Yes
  • Security: Electric Gate, Patrolled Area
Utilities
  • Utilities: FKAA, Water Separate Meter, Cable Available, Elect Separate Meter, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: No
  • Pool: Yes
  • Handicap Access: No
  • Pool Info: Heated: Yes
  • Pool Info: In Ground, Screened In, Decked, Concrete
  • Porch/Balcony: Open Porch/Balcony, Deck, Screened Patio, Patio, Screened P/B
Interior and Exterior Features
Interior Features
  • Floor: Tile
  • Interior Features: Drapes/Blinds Incl, Built-in Cabinets, Window Treatments, Whirlpool Bath Tub, Storage, Smoke Alarms, Elevator, Entrance Foyer, Fireplace(s)
  • Pre-Wired: Cable
  • Appliances: Washer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Tile Roof
  • Shutters: Accordion, Bahama
  • Construction: CBS, Concrete
  • Dockage: Boat Slip, Basin
  • Exterior Features: Chickee Hut, Storage, Lighting, Fruit Tree(s)
  • Windows/Doors: Sliding Glass Doors, Casement
Room Information
  • Specialty Rooms: Utility Room, Workshop

Property History for 111 Windy Point Circle

DateEvent & SourcePriceAppreciation
Dec 2, 2025

Listed (Active)

FKMLS #617541

$3,400,000—
Sep 19, 2023

Sold

FKMLS #605505

$4,900,000—
Aug 31, 2023

Pending

FKMLS #605505

—
Aug 31, 2023

Backup Contract

FKMLS #605505

—
May 27, 2023

Listed (Active)

FKMLS #605505

$5,200,000—
May 26, 2023

Expired

FKMLS #601388

—
Dec 3, 2022

Listed (Active)

FKMLS #601388

—
Jul 13, 2022

Pending

FKMLS #601388

—
Jul 13, 2022

Backup Contract

FKMLS #601388

—
Jun 13, 2022

Price Change

FKMLS #601388

$5,400,000—
Jun 13, 2022

Listed (Active)

FKMLS #601388

$5,125,000—
Jul 27, 2011

Temp Off Market

FKMLS #552531

—
Jul 6, 2010

Listed (Active)

FKMLS #552531

$2,900,000—
Mar 5, 2010

Expired

FKMLS #544740

—
Mar 6, 2008

Listed (Active)

FKMLS #544740

$3,400,000—
Mar 15, 1999

Sold

FKMLS #411176

$791,000—
Jul 24, 1998

Listed (Active)

FKMLS #411176

$895,000—
Jul 23, 1998

Sold

FKMLS #410829

$600,000—
Jun 16, 1998

Listed (Active)

FKMLS #410829

$725,000—
DateEvent & SourcePrice
12/02/2025

Listed (Active)

FKMLS #617541

$3,400,000
09/19/2023

Sold

FKMLS #605505

$4,900,000
08/31/2023

Pending

FKMLS #605505

—
08/31/2023

Backup Contract

FKMLS #605505

—
05/27/2023

Listed (Active)

FKMLS #605505

$5,200,000
05/26/2023

Expired

FKMLS #601388

—
12/03/2022

Listed (Active)

FKMLS #601388

—
07/13/2022

Pending

FKMLS #601388

—
07/13/2022

Backup Contract

FKMLS #601388

—
06/13/2022

Price Change

FKMLS #601388

$5,400,000
06/13/2022

Listed (Active)

FKMLS #601388

$5,125,000
07/27/2011

Temp Off Market

FKMLS #552531

—
07/06/2010

Listed (Active)

FKMLS #552531

$2,900,000
03/05/2010

Expired

FKMLS #544740

—
03/06/2008

Listed (Active)

FKMLS #544740

$3,400,000
03/15/1999

Sold

FKMLS #411176

$791,000
07/24/1998

Listed (Active)

FKMLS #411176

$895,000
07/23/1998

Sold

FKMLS #410829

$600,000
06/16/1998

Listed (Active)

FKMLS #410829

$725,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 111 Windy Point Circle

Taxable ValueLand$2,376,900Additions$811,124Total$3,188,024
Tax Record2024$28,160 ($2,347 / month)
Home Facts
Beds3Baths3Total Finished SqFt2,446 SqFtAbove Grade Finished SqFt2,446 SqFtStories2Lot Size37,055 SqFtStyleSingle Family ResidenceYear Built1988Year Renovated2008CountyMONROEAPN00333641-007700Fireplace TypeHas Fireplace

Schools near 111 Windy Point Circle

This home is within Monroe.
Rating
School
Type
Grades
Distance
Stanley Switlik Elementary School
Public - PK to 5
Marathon School
Public - 6 to 12
Coral Shores High School
Public - 9 to 12
Big Pine Academy
Charter - PK to 5
Rating
School
Distance
Stanley Switlik Elementary School
PublicPK to 5

Marathon School
Public6 to 12

Coral Shores High School
Public9 to 12

Big Pine Academy
CharterPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 111 Windy Point Circle, Marathon, FL 33050

111 Windy Point Circle is a single family home for sale in Marathon, FL 33050. This property was listed for sale on December 2, 2025 by Ocean Sotheby's International, it's currently listed at $3,400,000. It has been on the market for a total of 24 days and was last sold on September 19, 2023. This listing's school district is Monroe. Nearby schools include Stanley Switlik Elementary School, Marathon School and Coral Shores High School. 111 Windy Point Circle is a 3-bed, 4-bath, 2,446 sqft single family home built in 1988.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Ocean Sotheby's International

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.