111 Windy Point Cir, Marathon, FL 33050
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Property image
OFF MARKET

111 Windy Point Cir
Marathon, FL 33050

  • 3 Beds
  • 3 Baths
  • 2,446 sqft (on 0.87 acres)

$4,256,200

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $24,909/mo*
Refinance Your Home

$4,256,200

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $24,909/mo*
Refinance Your Home
3 Beds
3 Baths
2,446 sqft
(on 0.87 acres)

Local Information

  • Map ViewExplore the area around 111 Windy Point Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
0.87 acres
Living Area
2,446 sqft
Price/Sqft
$1,740
Parking
Attached Garage
HOA
$238/Monthly

About this House

Unique 1.75 acres (2 separate adjoining lots) of private property located in gated Stirrup Key includes 3 protected basin docks. This unique property offers a separated buildable lot (38,333 SF lot)providing a great opportunity for those buyers looking to create their own private estate for themselves or a multigenerational compound for your family. Awesome views from 660 Ft of open water that provides you sunrises and sunsets from this home. Spectacular views from the sunset Gazebo offers the picturesque 7 mile Bridge off in the distance. This custom built Mediterranean style home features the beauty, tranquility and privacy of your very own resort. Gulf views everywhere from the 11,000 SF court yard patio with spacious tiki hut for another entertaining area. A beautiful pool and deck, on the same level of the great room for easy entertaining from the kitchen. The 100 ft of 3 tiered terraced gardens with palm trees includes an easy walk way down to the patio with mature palms, majestic date palms and many other numerous plants for the gardeners delight. Architectural designed cathedral ceilings in every room includes beautiful wood Bahama shutters. Spacious great room includes a coral fireplace and walk out access to the pool with gulf views. There are separate wings for the master suite and guest bedrooms. The master suite includes his and her closets and skylights in the master bath. Additional features include an elevator, a 12,000 gallon cistern, garage for your car & golf carts and large storage area includes a pool table, a 2nd washer and dryer, and work benches. Short drive to Marathon airport!
111 Windy Point Cir, Marathon, FL 33050 is a 3 bedroom, 4 bathroom, 2,446 sqft single-family home built in 1988. It last sold for $4,900,000 on Sep 19, 2023 (6% below the $5,200,000 asking price). It is currently off market. The Trulia Estimate is $4,256,200, with a rent estimate of $6,285/month.

Home Details for 111 Windy Point Cir

Interior Features

Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 2446 Square Feet
Appliances & Utilities
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Wine CoolerDishwasherDryerLaundry: Laundry RoomRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Heat Pump,Ceiling Fans(s)
Windows, Doors, Floors & Walls
Window: Casement, Skylight(s)Flooring: Tile, Combination
Levels, Entrance, & Accessibility
ElevatorFloors: Tile, Combination
View
No View
Security
Security: Security Gate

Exterior Features

Exterior Home Features
Other Structures: GazeboExterior: Chickee Hut, Lighting, StorageHas a Private Pool
Parking & Garage
Has a GarageHas an Attached GarageParking: Attached
Pool
Pool: Concrete, DeckedPool
Frontage
WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Building: Tall - 10Ft & OverConstruction Materials: CBS
Property Information
Parcel Number: 00333641007700Additional Parcels Description: 00333641-007800

Price & Status

Price
List Price: $5,200,000

Active Status

MLS Status: Closed

Media

Location

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

Building

Building Area
Building Area: 2446 Square Feet

Community

Community Features: Community Boat Ramp

HOA

HOA Fee Includes: OtherHas an HOAHOA Fee: $2,850/Annually

Lot Information

Lot Area: 0.87 acres

Offer

Listing Terms: Seller Finance Psble, Cash, Conventional

Miscellaneous

Mls Number: 605505

Additional Information

Community Boat Ramp
Last check for updates: about 3 hours ago
Listed by Wanda G Brock, P.A., (305) 304-8862
Coldwell Banker Schmitt Real Estate Co.
Kim Rabito Show, (305) 304-8591
Coldwell Banker Schmitt Real Estate Co.
Bought with: outside of mls, Outside Of MLS
Source: FLKMLS, MLS#605505

Price History for 111 Windy Point Cir

DatePriceEventSource
03/27/2026$2,900,000ListingRemovedKey West AOR #617541
03/10/2026$2,900,000PendingToActiveKey West AOR #617541
03/05/2026$2,900,000ContingentFLKMLS #617541
02/12/2026$2,900,000PriceChange
Key West AOR #617541
12/02/2025$3,400,000Listed For SaleKey West AOR #617541
09/19/2023$4,900,000Sold
FLKMLS #605505
09/12/2023$5,200,000PendingFLKMLS #605505
08/31/2023$5,200,000ContingentFLKMLS #605505
05/31/2023$5,200,000Listed For SaleFLKMLS #605505
05/27/2023ListingRemovedKey West AOR #601388
12/03/2022$5,400,000PriceChange
FLKMLS #601388
07/29/2022$5,125,000PendingFLKMLS #601388
07/13/2022$5,125,000ContingentFLKMLS #601388
06/13/2022$5,125,000Listed For SaleFLKMLS #601388
07/08/2012$2,900,000ListingRemovedAgent Provided
08/06/2010$2,900,000PriceChange
Agent Provided
07/17/2010$2,600,000Listed For SaleAgent Provided
05/03/2010$3,400,000ListingRemovedAgent Provided
01/31/2009$3,400,000PriceChange
Agent Provided
09/30/2008$3,780,000PriceChange
Agent Provided
04/16/2008$4,200,000Listed For SaleAgent Provided
03/31/1999$791,000Sold
N/A
08/24/1998$600,000Sold
N/A
04/11/1996$600,000Sold
N/A

Market trends in Marathon

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$723K
$19.17KMoM
Sale-to-List Price
94.6%
Price per sq ft
$628
$22MoM
Available listings
251
17MoM
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Property Tax and Assessment

Year2025
Tax$28,130
Assessment$3,188,024
Home facts updated by county records

Comparable Sales for 111 Windy Point Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
358 Stirrup Key Blvd, Marathon, FL
0.16
Single-Family Home
$2,155,000
06/25/26
3
2
2,534
101 Windy Point Circle, Marathon, FL
0.10
Single-Family Home
$2,675,000
12/23/25
4
2.5
3,260
359 Stirrup Key Blvd, Marathon, FL
0.14
Single-Family Home
$2,950,000
12/08/25
3
2
1,995
199 Stirrup Key Blvd, Marathon, FL
0.58
Single-Family Home
$2,028,000
06/23/26
5
5
3,467
111 Brian Rd, Marathon, FL
0.86
Single-Family Home
$3,250,000
04/09/26
4
3.5
4,256
412 122nd St, Marathon, FL
1.20
Single-Family Home
$2,595,000
08/13/25
3
2.5
2,391
11243 3rd Ave, Marathon, FL
0.91
Single-Family Home
$1,500,000
10/16/25
5
4
2,416
209 E Bruce Ct, Marathon, FL
0.90
Single-Family Home
$2,300,000
12/12/25
4
2
1,852
11280 1st Ave, Marathon, FL
0.95
Single-Family Home
$982,000
12/04/25
3
2.5
1,842

Nearby homes

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Assigned Schools

These are the assigned schools for 111 Windy Point Cir.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 48 % Say kids play outside

  • 44 % 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

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Apartments for Rent

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Explore by feature - Pet Friendly

16 pet-friendly rentals in Marathon, FL

Explore by feature - Garage

6 rentals with a garage in Marathon, FL

Explore by feature - Air Conditioning

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Explore by feature - Pool

17 rentals with a pool in Marathon, FL

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15 rentals with a washer/dryer in Marathon, FL

Explore by feature - Outdoor Space

Homes for sale near 111 Windy Point Cir

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Off Market Homes Near 111 Windy Point Cir

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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.