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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$2,675,000
101 Windy Point Circle
Marathon, FL 33050
MLS# 614358
Status: Closed
4 beds  |  3 baths  |  3260 sqft


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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

Details
Maps
Documents
Contract Information
Current Price: $2,675,000
Listing Date: 2025-03-27
Listing Board: Florida Keys
Leased Price Monthly: $2,675,000
As is Rght to Inspct: Yes
Location, Tax & Legal
Street #: 101
Street Name: Windy Point
Street Suffix: Circle
Key/Island: Marathon
State/Province: FL
Zip Code: 33050
County: Monroe
Subdivision: Stirrup Key Sub (52.5)
Area: 15 - Sombrero Bch Rd to Vaca Cut Gulfside
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 5
Pool: Yes
Year Built: 2018
Lot SqFt: 13135
Acres: 0.3
Living Apx SqFt: 3260
SqFt Source: Tax Records
Total Bedrooms: 4
Full Baths: 2
Half Baths: 1
Total Baths: 3
Rentals Allowed: With Restrictions
Min Rental Days: 365
Association Info
Mandatory Home Owners Asc: Yes
1st Right of Refusal: No
Assoc Approval Req: No
Association Fee $: 116.66
Assoc/Mnt Fee Per: Monthly
Dockage
Dock Length: 20
Dock: Wood
Dock Permit: Yes
Building Style
Above Flood: Yes
# Stories: 2 Stories
Vehicle Storage
Car(s): 4+
Financial Status
Standard Sale: Yes
Status Change Info
Under Contract Date: 2025-12-03
Leased Date: 2025-12-23
Leased Price Monthly: $2,675,000
Status: Closed
Property Features
Fee Includes: Common Area Mnt; Security
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Harbor/Marina View; Open Water View
Dockage: Boat Ramp; Boat Slip; Other Dockage
Property Condition: New Construction
Vehicle Storage: Garage; Carport; Auto Door Opener; RV Parking Open; Trailer Storage
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Heating: Central
Utilities: Municipal Sewer; Propane
Interior Features: Built-in Cabinets; Cathedral Ceilings; Granite Counter Top; Security System; Split Bedroom; Tray Ceilings; Walk-in Closet(s)
Specialty Rooms: Laundry Room; Loft
Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features: Fencing; Hot Tub; Lighting; Sandy Beach
Pool Info: In Ground; Salt Water
Construction: CBS
Floor: Concrete; Marble; Wood
Roof: Metal Roof
Pets: Pets Allowed
Neighborhood Feature: Community Boat Ramp
Security: Electric Gate; On Premises System
Land Size: 1/4 - 1/2 Acre
Terms: Cash; Conventional
Title: Negotiable
GF-Interior Features: Low Flow Toilets; Programmable Thermst
Supplements
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.
Listing Documents
View Document Dock Extension Approval
View Document Survey

Listing Office: Bluecastle Real Estate

Last Updated: December - 23 - 2025

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)