Winthrop, MA

  • Overview
  • Performance
  • Listings
  • Buy Box

Key Performance Metrics

Market snapshot

Performance indicators for the Winthrop short-term rental market based on reliable data.

Listings

37 / 82

Reliable / Active

Cap Rate

6%

Middle-Earners Gross Yield

Revenue

$41,367

Middle-Earners Revenue

Occupancy

70%

Middle-Earners Occupancy

Home Value

$673,404

Median Home Sale Price

Top Earners

$82,323

Top-Earners Revenue

Winthrop

Market Revenue Seasonality

Top Listings

Highest revenue

The highest-performing listings in Winthrop.

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C

Challenging to Investors

Winthrop Regulations

STRs are legal but tightly constrained by a strict 1.5% housing-stock cap and a primary-residence, owner-occupied rule that bars non-owner-occupied, multi-family, and ADU units, limiting investor participation. Multi-agency inspections, annual licensing ($300), non-transferable licenses, and a July 1 renewal cycle add complexity and compliance risk.

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About Winthrop

Winthrop is a town in Suffolk County, Massachusetts, United States. The population was 19,316 at the 2020 census. Winthrop is an ocean-side suburban community in Greater Boston situated at the north entrance to Boston Harbor, close to Logan International Airport. It is located on a peninsula, 1.6 square miles (4.2 km2) in area, connected to Revere by a narrow isthmus and to multiple portions of Boston by a bridge over the harbor inlet to the Belle Isle Marsh Reservation in the Neighborhood of East Boston, a shared border at the Boston Logan International Airport, and at Deer Island. Settled in 1630, Winthrop is one of the oldest communities in the United States. It is also one of the smallest and most densely populated municipalities in Massachusetts. It is one of the four cities that comprise Suffolk County (the others are Boston, Revere, and Chelsea). It is the southernmost part of the North Shore, with a 7-mile (11 km) shoreline that provides views of the Atlantic Ocean to the east and of the Boston skyline to the west. In 2005, the Town of Winthrop voted to change its governance from a representative town meeting adopted in 1920 to a council-manager form of government. Under Massachusetts law, as of 2006 when the new Town Charter took effect, Winthrop became de jure a city. However, it is one of thirteen cities in Massachusetts that chose to remain known as a 'town.'

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