101 Windy Point Cir, Marathon, FL 33050
Property image
Property image
SOLD
DEC 23, 2025

$2,755,900

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 3,260 sqft (on 0.30 acres)

101 Windy Point Cir, Marathon, FL 33050

Est. Refi. Payment $16,611/mo*
Refinance Your Home
Currently Off Market - Sold Dec 23, 2025 for $2,675,000 (3% below list price)

Home Value

Trulia Estimate
$2.76M
Since last month
Increased$33K (+1.2%)
Since last year
Decreased$2K (-0.1%)
Since last sale
Increased$75K (+2.8%)
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 +41% in the last 10 years
MonthEstimated value
2026
September 2026$2.75M
August 2026$2.72M
July 2026$2.7M
June 2026$2.68M
May 2026$2.64M
April 2026$2.66M
March 2026$2.65M
February 2026$2.67M
January 2026$2.67M
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
351 Stirrup Key Blvd, Marathon, FL
0.04
Single-Family Home
$1,800,000
06/29/26
3
3
1,802
358 Stirrup Key Blvd, Marathon, FL
0.08
Single-Family Home
$2,155,000
06/25/26
3
2
2,534
199 Stirrup Key Blvd, Marathon, FL
0.50
Single-Family Home
$2,028,000
06/23/26
5
5
3,467
359 Stirrup Key Blvd, Marathon, FL
0.08
Single-Family Home
$2,950,000
12/08/25
3
2
1,995
111 Brian Rd, Marathon, FL
0.78
Single-Family Home
$3,250,000
04/09/26
4
3.5
4,256
209 E Bruce Ct, Marathon, FL
0.81
Single-Family Home
$2,300,000
12/12/25
4
2
1,852
11243 3rd Ave, Marathon, FL
0.81
Single-Family Home
$1,500,000
10/16/25
5
4
2,416
11250 3rd Ave, Marathon, FL
0.79
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
351 Stirrup Key Blvd, Marathon, FL 33050
0.04
$1,800,000
3
3
1,802
Recently Sold
347 Stirrup Key Boulevard, Marathon, FL 33050
0.07
$2,718,700
4
3
2,496
Off Market
339 Stirrup Key Blvd, Marathon, FL 33050
0.11
$3,510,900
4
4
2,521
Off Market
Windy Point, Marathon, FL 33050
0.06
-
-
-
-
Off Market
355 Stirrup Key Blvd, Marathon, FL 33050
0.06
$3,300,000
4
3.5
2,540
For Sale
358 Stirrup Key Blvd, Marathon, FL 33050
0.08
$2,155,000
3
2
2,534
Recently Sold
359 Stirrup Key Blvd, Marathon, FL 33050
0.08
$2,950,000
3
2
1,995
Recently Sold
105 Pirates Cove Dr, Marathon, FL 33050
0.20
$2,062,300
4
2.5
2,720
Off Market
Pirates Cove Dr, Marathon, FL 33050
0.22
-
-
-
-
Off Market
120 Pirates Cove Dr, Marathon, FL 33050
0.26
$2,099,000
4
4
3,476
For Sale
124 Pirates Cv, Marathon, FL 33050
0.29
$3,508,400
5
3
3,250
Off Market

Local Information

  • Map ViewExplore the area around 101 Windy Point Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2018
0.3 acre lot
3,260 sqft
$821/sqft
Garage
HOA $117/mo

About this House

For Sale by Owner/agent & priced below market value! Discover your dream waterfront lifestyle on an expansive 13,135 sq ft lot with breathtaking open water views. This 4-bed, 2.5-bath plus loft home offers 3,260 sq ft of luxury. Built in 2018, it features superior CBS construction, a metal roof, and impact windows, all elevated 11 ft above sea level.

Your backyard oasis includes a sandy beach/yard, travertine deck, pool, and jacuzzi. Plus, a permitted plan (a $100k value) is ready for a 20K lb boat lift, 2 jet ski lifts, and 60 ft yacht pilings. A separate marina deeded dock can be included in the sale for an additional $150K - 12ft wide, 20 ft long, useful up to 9.5 ft beam
Located in the exclusive gated community of Stirrup Key https://www.cbs17.com/business/press-releases/ein-presswire/843690199/marathon-property-serves-as-case-study-in-coastal-resilience-and-insurance-savings/

Marathon Property Serves as Case Study in Coastal Resilience and Flood Insurance Savings

MARATHON, FL - August 27, 2025 - A recently listed property in Marathon, Florida, is drawing attention as a case study for mitigating financial and environmental challenges in the Florida Keys' real estate market. The residence, located at 101 Windy Point Circle, highlights how thoughtful construction and community planning can provide long-term stability for coastal homeowners facing escalating insurance costs and development pressures.

Homeownership in the Florida Keys has long been associated with high property values, but the increasing cost of flood insurance presents an equally significant financial hurdle. Under FEMA's Risk Rating 2.0, insurance premiums are now calculated based on individual property-specific factors, including a home's elevation, construction type, and proximity to water. This shift has resulted in a substantial increase in rates for many coastal properties.

The home at 101 Windy Point Circle serves as a notable counterpoint to this trend. The property, built in 2018 with superior CBS (concrete block and stucco) construction and elevated 11 feet above sea level, has an annual flood insurance premium of just $1,273. This rate is grandfathered and can be transferred to a new owner, creating a substantial and recurring financial advantage. The property's resilient design was tested in 2017 during Hurricane Irma, where it sustained minimal to no damage, a testament to its elevated construction and durable metal roof.

Alex Baglioni, CEO of Bluecastle Lending, Realty & Title, commented on the property's value. "As a professional in the real estate industry, the long-term value of this home's construction and elevation was immediately apparent," Baglioni stated. "The low, grandfathered-in flood insurance cost was a huge factor. This property is a smart investment in resilience and financial security that directly addresses some of the biggest challenges of owning property in the Florida Keys today."

Beyond its financial resilience, the property addresses another key issue affecting the Florida Keys: the impact of tourism on residential neighborhoods. The growth of short-term rentals has created widespread concerns over constant visitor traffic, noise complaints, and parking issues. The exclusive, gated community of Stirrup Key, where the home is located, maintains a strict policy prohibiting short-term rentals. This provides a serene, residential atmosphere and a quiet retreat from the constant traffic and noise often associated with high-turnover tourist areas. According to market data, this regulation has contributed to a consistent increase in property values within the community, demonstrating that this peaceful benefit also offers a notable financial gain.

The property also offers a rare amenity for a mariner. The residence holds a highly coveted, government-approved permit for a dock extension in the backyard, allowing for the construction of a dock to accommodate a 60-foot yacht, a boat lift, and two jet ski lifts. The ability to berth a vessel of this size directly on open water, but still protected in a cove, is an uncommon feature in this location.
The 2,620-square-foot residence features four bedrooms and sits on a 0.3-acre lot. The property is currently listed for sale by the owner/agent.

About Bluecastle Lending, Realty & Title: Bluecastle Lending, Realty & Title is a Florida-based company specializing in real estate, mortgage lending, and title services. The firm provides comprehensive solutions for buyers and sellers, leveraging extensive market knowledge to navigate the complexities of Florida's real estate landscape.
101 Windy Point Cir, Marathon, FL 33050 is a 4 bedroom, 3 bathroom, 3,260 sqft single-family home built in 2018. It last sold for $2,675,000 on Dec 23, 2025 (3% below the $2,750,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,755,900, with a rent estimate of $8,299/month.
Last check for updates: 1 day ago
Listed by Martin Baglioni, (954) 866-0000
Bluecastle Real Estate
Bought with: Teri Hiller, Coldwell Banker Schmitt Real Estate Co.
Source: FLKMLS, MLS#614358

Home Details for 101 Windy Point Cir

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3260 Square Feet
Appliances & Utilities
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s)DishwasherDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Has Heating Unspecified Type
Fireplace & Spa
Spa: HeatedHas a Spa
Windows, Doors, Floors & Walls
Flooring: Wood, Marble, Concrete
Levels, Entrance, & Accessibility
Floors: Wood, Marble, Concrete
View
No View
Security
Security: Security Gate, On Premises System, Security System

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/BalconyFencing: FencedExterior: Lighting, Sandy BeachHas a Private Pool
Parking & Garage
Has a GarageNo Attached GarageParking: Garage Door Opener,RV Access/Parking,Storage
Pool
Pool: In Ground, Salt WaterPool
Frontage
WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: CBSIs a New Construction
Property Information
Condition: New ConstructionParcel Number: 00333641008200

Price & Status

Price
List Price: $2,750,000Price Per Sqft: $821/sqft

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 3260 Square Feet

Community

Community Features: Community Boat Ramp

HOA

HOA Fee Includes: Common Area Mnt, SecurityHas an HOAHOA Fee: $117/Monthly

Lot Information

Lot Area: 0.30 acres

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 614358

Additional Information

Community Boat Ramp

Price and Tax history

DateEventPrice
Dec 23, 2025
Source: FLKMLS #614358
Sold
$2,675,000
Dec 4, 2025
Source: FLKMLS #614358
Pending
$2,750,000
Nov 3, 2025
Source: FLKMLS #614358
PriceChange
$2,750,000
Price decreased by 5%
Sep 25, 2025
Source: FLKMLS #614358
PriceChange
$2,899,999
Price decreased by 2%
Sep 12, 2025
Source: FLKMLS #614358
PriceChange
$2,969,000
Price decreased by 1%

Market trends in Marathon

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
255
7MoM

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

LGBTQ Local Legal Protections

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.

Frequently asked questions about 101 Windy Point Cir

  • What is 101 Windy Point Cir estimated to be worth?
    Trulia's estimated value for 101 Windy Point Cir in Marathon, FL is $2,755,900.
  • What is the price history for 101 Windy Point Cir?
    101 Windy Point Cir in Marathon, FL last sold for $2,675,000 in December 2025.
  • Is Marathon a buyer's or seller's market?
    Marathon is currently a buyer's market, based on recent for-sale activity.
  • 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 recently sold homes in Marathon, FL.
  • Does 101 Windy Point Cir have air conditioning?
    Yes, 101 Windy Point Cir in Marathon, FL has air conditioning.
  • Does 101 Windy Point Cir have a pool?
    Yes, 101 Windy Point Cir in Marathon, FL has a pool.

Explore by feature - Pet Friendly

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