Winslow Homes stands apart through its commitment to excellence, cutting-edge marketing strategies, and deep local market knowledge across the states we serve. Our brokerage specializes in a range of real estate services, including: Residential Sales – Helping buyers find their dream homes and sellers achieve top dollar for their properties. Luxury & Coastal Properties – Expertise in high-end, waterfront, and vacation homes in desirable locations.Investment & Income Properties – Assisting investors in identifying profitable opportunities. New Construction & Development – Partnering with builders and developers to bring new projects to market. Relocation Services – Providing a seamless experience for clients moving to or from the areas we serve.

Winslow Homes is an independent real estate brokerage licensed in Massachusetts, Florida, Connecticut, and Rhode Island, dedicated to providing expert guidance, innovative marketing, and seamless transactions for buyers, sellers, and investors. With a reputation built on honesty, integrity, trust, and service (H.I.T.S.), Winslow Homes offers personalized, client-centered solutions that make real estate transactions smooth and successful.

At Winslow Homes, we believe in building lasting relationships with our clients, ensuring every transaction is guided by transparency, communication, and expert negotiation.

Winslow Homes was founded by Megan and Ryan Winslow, a husband-and-wife team who transformed their passion for real estate into a thriving brokerage. Their journey began in 2009, when they applied their entrepreneurial mindset, housing market expertise, and dedication to client success to real estate transactions in Central Massachusetts, and eventually Central and Coastal Florida. As a Massachusetts native and son of a real estate broker, Ryan Winslow pursued real estate at the conclusion of his military career, following an Honorable Discharge from the U.S. Army. Together, Megan and Ryan became a dynamic duo in the industry, providing expert representation and growing a loyal client base.

By 2016, they had expanded their reach across Massachusetts, Florida, Rhode Island, and Connecticut, earning recognition as one of the “Best of Central MA” and solidifying their reputation as trusted real estate professionals. Their success led to the creation of Winslow Homes LLC, a brokerage built on client-first service, market expertise, and a commitment to achieving real estate goals at the highest level.

Today, Winslow Homes continues to thrive as a full-service brokerage, offering a modern, results-driven approach while maintaining a personal touch in every transaction. Megan and Ryan reside in New Smyrna Beach, FL, with their three children-Jaikob, Jaelynn, and Julianna-leading a brokerage that reflects their values, experience, and dedication to helping clients succeed in real estate.

Whether you’re buying, selling, or investing, Winslow Homes is your trusted partner in real estate. 

Winslow Homes is a fully licensed real estate brokerage serving Massachusetts, Florida, Connecticut, and Rhode Island. With extensive market knowledge and a commitment to exceptional service, our team is equipped to help buyers, sellers, and investors navigate real estate transactions across these states. 

FLORIDA

New Smyrna Beach, FL 32168

Contact: (386) 690-5858

MASSACHUSETTS

Worcester, MA 01606

Contact: (386) 690-5858

CT & RI

Contact: (386) 690-5858