115 Windy Point Cir, Marathon, FL 33050
Property image
Property image
UNDER CONTRACT
3D VIEW
0.91 ACRES

$4,400,000

  • 3 Beds
  • 3 Baths
  • 2,623 sqft (on 0.91 acres)

115 Windy Point Cir, Marathon, FL 33050

Est. Mortgage $25,554/mo*
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Home Highlights

Property Type
Single-Family Home
Year Built
1978
Lot Size
0.91 acres
Price/Sqft
$1,677
Parking
Garage
HOA
$200/Monthly

Local Information

  • Map ViewExplore the area around 115 Windy Point Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Experience the charm and character of this Gulf-front Old Florida Keys fishing lodge located in Stirrup Key, one of Marathon's most exclusive gated communities. Known for its large estate lots, deep-water access, and serene open-Gulf vistas, Stirrup Key offers privacy, prestige, and a true island lifestyle, just minutes from the conveniences of Marathon. The property consists of two lots in total for a combined size of 39,500 sf. The home sits on one of the few deep-water sites in Stirrup Key with upgraded 165 foot pier dock with 6 new pilings, where the water is so clear you can watch tarpon, angelfish, snapper, nurse sharks, lobsters and rays gliding beneath the dock. Beautifully maintained and elevated above flood, the residence features 3 bedrooms, 3 baths, and a loft that can serve as a fourth bedroom or home office. Brand new roof and impact windows and sliders were recently installed for peace of mind. The open-concept great room boasts massive ceilings and walls of windows showcasing 180-degree Gulf views. A spacious kitchen with center island and new range, Gulf front bar, wide overhanging eaves, exposed wood beams, and natural stone accents showcase classic tropical lodge architecture, perfect for entertaining. The primary suite with a large ensuite bath provide comfort and style, while a screened porch opens to the heated pool, positioned behind lush landscaping for afternoon shade. Outdoors, you'll find a sandy beach area, irrigated native landscaping, and expansive decks perfect for sunset gatherings. Additional amenities include two garage bays, one carport bay, a workshop, garden shed, and abundant storage. Stirrup Key residents enjoy the peace of a gated, low-density community with a 365 day rental minimum, ensuring tranquility and exclusivity year-round. With its unmatched combination of deep water, open-Gulf views, and spacious multi-lot layout, this property is a true rarity in the Florida Keys with potential for expansion.
Last check for updates: about 4 hours ago
Listing courtesy of Ally Kelley, (727) 459-0493
Ocean Sotheby's International
Jo Ann Cook, (305) 360-7968
Ocean Sotheby's International
Source: FLKMLS, MLS#617542
Also Listed on FLKMLS.

Home Details for 115 Windy Point Cir

Interior Features

Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2623 Square Feet
Appliances & Utilities
Utilities: Water Separate Meter, Elect Separate Meter, Cable AvailableAppliances: Washer, Dishwasher, Refrigerator, Range, Oven, MicrowaveDishwasherMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile, Wood
Levels, Entrance, & Accessibility
Accessibility: NoneFloors: Tile, Wood
View
No View
Security
Security: Security Gate, Security Guard

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, PatioHas a Private Pool
Parking & Garage
Has a CarportHas a GarageNo Attached GarageHas Open ParkingParking: Garage Door Opener,Open,RV Carport,RV Access/Parking,Storage
Pool
Pool: In Ground, Concrete, DeckedPool
Frontage
WaterfrontOn Waterfront

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: CBS, Concrete, Frame, Combo Construction
Property Information
Parcel Number: 00333641007500

Price & Status

Price
List Price: $4,400,000Price Per Sqft: $1,677

Active Status

MLS Status: Pending

Media

Location

Direction & Address
City: MarathonCommunity: Stirrup Key Sub (52.5)

Agent Information

Listing Agent
Listing ID: 617542

Building

Building Area
Building Area: 2623 Square Feet

HOA

HOA Fee Includes: NoneHas an HOAHOA Fee: $2,400/Annually

Lot Information

Lot Area: 0.91 acres

Offer

Contingencies: Contingent

Miscellaneous

Mls Number: 617542Zillow Contingency Status: Under Contract

Around this home

What Locals Say about Marathon

At least 61 Trulia users voted on each feature.

  • 83 % Say car is needed

  • 79 % Say people would walk alone at night

  • 76 % Say parking is easy

  • 72 % Say it's quiet

  • 70 % Say it's dog friendly

  • 70 % Say yards are well-kept

  • 68 % Say there's holiday spirit

  • 61 % Say it's walkable to restaurants

  • 53 % Say there's wildlife

  • 53 % Say they plan to stay for at least 5 years

  • 51 % Say there are community events

  • 49 % Say kids play outside

  • 45 % Say neighbors are friendly

  • 37 % Say it's walkable to grocery stores

  • 36 % Say there are sidewalks

  • 29 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • 4yrv5tc4qr
    "Seafood festival, theater, music festival, turtle releases, homecoming parade, 4th of July fireworks on the beach"
    1
    Flag
  • Ingridfox
    "people love walking dogs on the beach and dog dog park at Sombrero Beach. A lot of restaurants are dog friendly. This is a great place for dog owners. "
    1
    Flag
  • C E.
    "There is no place for kids to hang out really except for the skate park. There are no malls, no skating rinks, no places for kids to meet safely. "
    1
    Flag
  • Jan M.
    "We have basic public transportation. I’d take a taxi anywhere in town. .............................,,"
    0
    Flag
  • Erin F.
    "There’s plenty of grass, sidewalks and quiet roads to walk along.. plus the public beach is always a dogs favorite adventure.. just pick up after your dog!"
    2
    Flag
  • Thurmankolb
    "Yes! Dog park just down the street. Lots of neighbors know each other by our dogs. Great vets n Marathon and good groomer."
    6
    Flag
  • Thurmankolb
    "Lots of community events and activities. Fishing tournaments, seafood festival, school carnivals, etc... "
    2
    Flag
  • Jamie B.
    "Everyone gets together for the kids at Halloween. We have a community park with special events planned for the kids and the beach is the sight for a special 4th of July. "
    0
    Flag
  • Abiezer31
    "Of course ,the neighbors the owner and dog are very nice I’m very proud living in my house.and this neighborhood "
    3
    Flag
  • Darren S.
    "I live off the beaten path across the street from a golf course. It's very quiet and tranquil. throb marinas surrounding the property and can walk to All shops and stores."
    0
    Flag
  • Cyndiepalmer
    "We are a friendly neighborhood. You walk your street and say Hi anytime. It is a safe street to live "
    0
    Flag
  • Ksperkinson
    "Safe clean near ocean good police pet friendly hospital is coming along in the construction have contract here at hospital looking forward to finding a good place for 3 months"
    0
    Flag
  • Stephanie M.
    "A lot of kids and cars. A fire station that is noisey but nice. Lizards everywhere. There is one hotel on this small island. There are A lot of Vacation homes here and crab catchers. When it rains you can't see the road."
    0
    Flag
  • Lb2071
    "water front community , is a small island called Flamingo Island. We have a 9 hole golf course and just 5 minutes from Publix and Kmart. Sombrero beach is right at the outset of the canals on the Atlantic ocean and the people are very loving and friendly."
    0
    Flag
  • Gonzalez8834
    "Marathon is a great place to life and have a family, very safe, quiet and full of great people. ......"
    0
    Flag
  • Tom A. C. M.
    "I live here (14 years) and love the area. Close accessibility to shopping, schools, churches, golf, beach, walking, biking. "
    0
    Flag
  • Anne K.
    "Lived here for many years and is one of the best places to live in Marathon. Conveniently located near schools, parks, shopping and beach just minutes away."
    0
    Flag
  • Debra G.
    "Only 8 miles from Marathon. Away from the winter traffic, airport noise. Crystal clean, flow through canals. Great place to vacation and a great place to live. "
    0
    Flag

Market trends in Marathon

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$774K
$51.67KMoM
Sale-to-List Price
—
Price per sq ft
$630
$2MoM
Available listings
260
8MoM

Home Value

Trulia Estimate
$4.04M
Since last month
Decreased$3K (-0.1%)
Since last year
Decreased$423K (-9.5%)
Since last sale
Decreased$554K (-12.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +58% in the last 10 years
MonthEstimated value
2026
August 2026$4.04M
August 2026$4.03M
July 2026$4.04M
June 2026$4.04M
May 2026$4.05M
April 2026$4.02M
March 2026$4.09M
February 2026$4.09M
January 2026$4.46M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
358 Stirrup Key Blvd, Marathon, FL
0.12
Single-Family Home
$2,155,000
06/25/26
3
2
2,534
101 Windy Point Circle, Marathon, FL
0.09
Single-Family Home
$2,675,000
12/23/25
4
2.5
3,260
351 Stirrup Key Blvd, Marathon, FL
0.12
Single-Family Home
$1,800,000
06/29/26
3
3
1,802
359 Stirrup Key Blvd, Marathon, FL
0.09
Single-Family Home
$2,950,000
12/08/25
3
2
1,995
199 Stirrup Key Blvd, Marathon, FL
0.53
Single-Family Home
$2,028,000
06/23/26
5
5
3,467
111 Brian Rd, Marathon, FL
0.80
Single-Family Home
$3,250,000
04/09/26
4
3.5
4,256
11243 3rd Ave, Marathon, FL
0.90
Single-Family Home
$1,500,000
10/16/25
5
4
2,416
209 E Bruce Ct, Marathon, FL
0.85
Single-Family Home
$2,300,000
12/12/25
4
2
1,852
11250 3rd Ave, Marathon, FL
0.87
Single-Family Home
$1,400,000
07/31/26
4
3
1,740

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
Windy Point, Marathon, FL 33050
0.08
-
-
-
-
Off Market
111 Windy Point Cir, Marathon, FL 33050
0.06
$4,113,000
3
3
2,446
Off Market
359 Stirrup Key Blvd, Marathon, FL 33050
0.09
$2,950,000
3
2
1,995
Recently Sold
351 Stirrup Key Blvd, Marathon, FL 33050
0.12
$1,800,000
3
3
1,802
Recently Sold
358 Stirrup Key Blvd, Marathon, FL 33050
0.12
$2,155,000
3
2
2,534
Recently Sold
347 Stirrup Key Boulevard, Marathon, FL 33050
0.15
$2,693,500
4
3
2,496
Off Market
339 Stirrup Key Blvd, Marathon, FL 33050
0.18
$3,433,700
4
4
2,521
Off Market
105 Pirates Cove Dr, Marathon, FL 33050
0.22
$2,017,600
4
2.5
2,720
Off Market
Pirates Cove Dr, Marathon, FL 33050
0.23
-
-
-
-
Off Market
120 Pirates Cove Dr, Marathon, FL 33050
0.25
$2,199,000
4
4
3,476
For Sale
124 Pirates Cv, Marathon, FL 33050
0.27
$3,502,300
5
3
3,250
Off Market
313 Stirrup Key Blvd, Marathon, FL 33050
0.46
$350,000
-
-
-
For Sale

Price and Tax history

DateEventPrice
Jun 2, 2026
Source: FLKMLS #617542
Contingent
$4,400,000
Apr 14, 2026
Source: FLKMLS #617542
PriceChange
$4,400,000
Price decreased by 2%
Feb 12, 2026
Source: FLKMLS #617542
PriceChange
$4,500,000
Price decreased by 8%
Dec 2, 2025
Source: Key West AOR #617542
Listed For Sale
$4,900,000
Sep 19, 2023
Source: FLKMLS #604950
Sold
$4,595,000

LGBTQ Local Legal Protections

Ally Kelley, Ocean Sotheby's International
Agent Phone: (727) 459-0493
MLS Internet Data Exchange (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, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.

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Frequently asked questions about 115 Windy Point Cir

  • What is the estimated monthly payment for 115 Windy Point Cir?
    Based on a $4,400,000 list price with 20% down at today's rates, the estimated monthly payment for 115 Windy Point Cir in Marathon, FL is approximately $26,091 (about $23,009 principal & interest, $3,007 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 115 Windy Point Cir compare to homes in Marathon?
    115 Windy Point Cir in Marathon, FL is listed at $4,400,000, about 468% above the $774K median sale price in Marathon.
  • What do residents say about Marathon?
    Residents describe Marathon, FL as easy to park in, quiet, and dog-friendly. Most residents say you need a car. See homes for sale in Marathon, FL.
  • What are the closest schools to 115 Windy Point Cir?
    The closest schools to 115 Windy Point Cir in Marathon, FL are Marathon School (Middle/High, rated 5/10), Stanley Switlik Elementary School (Pre-K, rated 5/10).
  • Does 115 Windy Point Cir have air conditioning?
    Yes, 115 Windy Point Cir in Marathon, FL has air conditioning.
  • Does 115 Windy Point Cir have a pool?
    Yes, 115 Windy Point Cir in Marathon, FL has a pool.
115 Windy Point Cir, Marathon, FL 33050 is a 3 bedroom, 3 bathroom, 2,623 sqft single-family home built in 1978. This property is currently available for sale and was listed by FLKMLS on Dec 2, 2025. The MLS # for this home is MLS# 617542.