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$2,675,000
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Property Description
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
Full Property Details
Full Property Details for 101 Windy Point Cir
General
- Sold For: $2,675,000
- HOA FEE: $117/month
- Taxes: $18,036 (2024)
- Status: Closed
- Type: Single Family
- Source: 927
- MLS ID: 614358
- Added to Site: 433 day(s) ago
Interior
- Interior Features: Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Granite Counter Top, Security System, Split Bedroom, Tray Ceilings, Loft, Low Flow Plumbing Fixtures, Smart Thermostat
- Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Freezer, Gas Appliances, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
- Flooring: Wood, Concrete, Marble
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Community Boat Ramp
- Pool: Yes
- Pool Description: Salt Water, In Ground
- Security/Safety: Electric Gate, On Premises System
Exterior
- Exterior Features: Lighting, Fencing, Hot Tub, Sandy Beach, Boat Slip
- Deck/Patio: Open Porch/Balcony
- Porch/Patio/Deck: Open Porch/Balcony
Parking
- Garage: Yes
- Parking Features: Carport, Garage Door Opener
Location
- Area: 15 - Sombrero Bch Rd to Vaca Cut Gulfside
- County: Monroe
- Subdivision: Stirrup Key Sub (52.5)
Community
- Association: Yes
- Assoc. Fees Include: Common Area Mnt, Security
- Pets Allowed: Yes
Heating & Cooling
- Central air: Yes
- Air Conditioning: Yes
- Cooling Type: Central Air, Ceiling Fans(s)
- Heating Type: Central
Structural Information
- Architectural Style: Above Flood
- Construction Status: New Construction
- Construction: CBS
- Roof: Metal
- Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window
- Square Feet: 3,260
- Sq. Ft. Source: Tax Records
- Year Built: 2018
- Property Condition: New Construction
Lot Features
- Property View: Harbor/Marina View, Open Water View, Bay
- Lot Size (Acres): 0.3
- Lot Size (Sq. Ft.): 13,135
- Zoning: RL - Residential Low
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: Bay Front, Gulf Front, Open Water
Financial Considerations
- Association Fee: Yes
- Association Fee: $117
- Assoc Fee Freq.: Monthly
- Tax Amount: $18,036.84
- Tax Year: 2024
- Terms: Cash, Conventional
Disclosures and Reports
- Legal Description: LT 82 STIRRUP KEY SUBDIVISION PB7-4 STIRRUP KEY OR807-252 OR1064-246 OR1622-1740 OR1622-1741 OR2870-2067 OR3001-0494 OR
- Flood Zone: AE
- APN: 00333641-008200
Listed by Bluecastle Real Estate, Martin Baglioni (954) 866-0000
Sold by Coldwell Banker Schmitt Real Estate Co., Teri Hiller
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Schools
Schools serving 101 Windy Point Cir
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Stanley Switlik Elementary School 3400 Overseas Highway, Marathon, FL 33050 | PK-5 | 3.9 mi |
Marathon School 350 Sombrero Beach Road, Marathon, FL 33050 | 6-12 | 3.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 101 Windy Point Cir
Date
Details
Price
Change
Source
12/23/2025
Sold
$2,675,000
-2.73%
MLS
11/03/2025
Price Reduced
$2,750,000
-5.17%
MLS
9/25/2025
Price Reduced
$2,899,999
-2.32%
MLS
9/12/2025
Price Reduced
$2,969,000
-0.67%
MLS
9/06/2025
Price Reduced
$2,989,000
-0.33%
MLS
7/28/2025
Price Reduced
$2,999,000
-2.72%
MLS
7/17/2025
Price Reduced
$3,083,000
-0.52%
MLS
6/12/2025
Price Reduced
$3,099,000
-1.59%
MLS
5/29/2025
Price Reduced
$3,149,000
-1.56%
MLS
5/16/2025
Price Reduced
$3,199,000
-0.81%
MLS
3/27/2025
Listed
$3,225,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
101 Windy Point Circle, Marathon, FL 33050 (MLS# 614358) is a Single Family property that was sold at $2,675,000 on December 23, 2025. Want to learn more about 101 Windy Point Circle? Do you have questions about finding other Single Family real estate for sale in Marathon? You can browse all Marathon real estate or contact a Coldwell Banker agent to request more information.

