Amy Cutrona
Amy Cutrona is a Real Estate Advisor with the Freitas Monteforte Group at Compass, specializing in luxury, waterfront and coastal properties throughout Miami Beach, Surfside, Bal Harbour, Bay Harbor Islands and surrounding South Florida communities, as well as Cape Cod, Massachusetts.
A full-time resident of Surfside, Florida, with a second home in Cotuit on Cape Cod, Amy brings firsthand knowledge of two highly sought-after coastal markets. Her unique connection to both South Florida and Cape Cod gives her an authentic understanding of the lifestyle and priorities of clients searching for primary residences, waterfront homes, seasonal properties and second homes.
Amy combines personalized service and local market expertise with the resources and reach of the Freitas Monteforte Group at Compass. The team is ranked among the top 1.5% of real estate professionals nationwide, the #1 team in Barnstable and the #2 team in Osterville, and among the Top 1,000 teams in the United States by sales volume. In 2025, the group closed $60.44 million across 50 transactions, with an average transaction price of approximately $1.21 million. Since 2020, the team has recorded more than 603 historic sales, bringing more than 27 years of experience and 133+ verified five-star reviews across Google and Zillow.
Through the Freitas Monteforte Group, Amy’s clients benefit from sophisticated marketing, strategic pricing guidance, transaction support, local market intelligence and the broader Compass network, while receiving the personal attention and hands-on guidance that define her approach.
Known for her warm, thoughtful and attentive style, Amy believes successful real estate representation begins with understanding the person behind the transaction. She takes the time to understand each client’s lifestyle, financial priorities and long-term goals so she can provide guidance tailored to what matters most.
Amy also brings a natural appreciation for architecture, interiors and visual storytelling. Married to professional architectural and lifestyle photographer Dan Cutrona, she has developed a deep understanding of the details, presentation and visual elements that help a property connect with prospective buyers.
Amy and Dan are raising their three children in Surfside and spend part of each year at their home in Cotuit. Living between South Florida and Cape Cod gives Amy a personal perspective that is especially valuable to clients relocating between the Northeast and South Florida or searching for a second home in either market.
Whether helping a family find a waterfront home in Miami Beach, representing a seller in Surfside, or assisting a buyer in finding the perfect Cape Cod retreat, Amy combines genuine local knowledge, personalized service and the strength of the Freitas Monteforte Group at Compass to deliver a thoughtful and highly informed real estate experience.
Areas of Focus
South Florida: Miami Beach • Surfside • Bal Harbour • Bay Harbor Islands • Waterfront Homes • Luxury Condominiums • Second Homes • Relocation
Cape Cod: Cotuit • Osterville • Centerville • Barnstable • Mashpee • Waterfront Homes • Coastal Properties • Vacation Homes • Second Homes
Specialties: Luxury Real Estate • Waterfront Real Estate • Coastal Homes • Second Homes • Relocation • Buyer Representation • Seller Representation