Answers from broker owners Ryan and Megan Winslow
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
Florida has no state personal income tax. Massachusetts taxes income. Home prices in coastal Volusia County sit below many Massachusetts suburbs, while Florida homeowners insurance and flood insurance often cost more.
Yes. Ryan and Megan Winslow hold real estate broker licenses in both Massachusetts and Florida. He grew up in Worcester County and now works from New Smyrna Beach, so one broker manages the sale up north and the purchase down south.
Most clients get pre-approved first, list the Massachusetts home, and write Florida offers with a closing date after the Massachusetts closing. A rent-back or a bridge option covers gaps. Plan timing with your broker and lender before you list.
Written by Ryan and Megan Winslow, broker/owner of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army retired. About Ryan and Megan.
Updated 2026-09-28. General information, not legal, tax or insurance advice.
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