Rent to Own Homes near Winthrop Town, MA

  • Winthrop is a small town located at the entrance of Boston Harbor. Settled in 1630, the town was named for Puritan leader John Winthrop and is one of the oldest communities in the United States. Though it was originally part of Boston and later part of neighboring Chelsea, Winthrop finally became an incorporated town in 1852. Because Winthrop is surrounded on three sides by the waters of Massachusetts Bay, today's residents enjoy boating, fishing and visiting the local beaches.

Check out over 300 Winthrop Town, MA rent to own homes for sale, which may include auction properties, for sale by owner, and more.

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Top 4 Reasons to Live in Winthrop, MA

  • Local restaurants to satisfy every craving! Though not even two square miles, the town of Winthrop offers many excellent dining options. For water views, check out Alia Ristorante, Cafe Rossetti's or Belle Isle Seafood. La Siesta serves up some of the best Mexican food in the Boston metro area and features strong margaritas and authentic mole. For meat lovers, Blackstrap BBQ offers a wide variety of barbecued meats with a side of their unique sweet potato salad.
  • Home values are on the rise! According to Zillow, the average home price in Winthrop is $367,500, up over nine percent over the previous year. High-end homes with clear views of the Boston skyline can be found in Cottage Park, while more affordable rent to own options and classic beach cottages are available along Winthrop Shore Drive.
  • Affordable rents and various options! The average monthly rent in Winthrop is just $1,500, which is far below the Boston metro average of $2,195. For a complex with a pool and an interesting military history, check out Fort Heath Apartments on Pond Street. Beach lovers will love the rental homes right on Winthrop Shore Drive, where you can choose a unique half of a duplex or a floor of a traditional Boston triple-decker. A more traditional apartment complex, Oceanside Apartments, is just steps from the town beach.
  • Check out the beach! In Winthrop, you're never more than a short walk from the ocean. Head to Winthrop Shore Drive to enjoy a low-key beach day right in town. For a day on the water, hire a boat at Revolution Charters or Strike Sportfishing Charters. Land lubbers may prefer hiking out to the Deer Island Harborwalk. Though once an island in Boston Harbor, Deer Island was left connected to Winthrop after a hurricane changed the landscape in the 1930s. Today visitors can enjoy stunning views of the harbor and the Boston skyline as they enjoy the two-and-a-half-mile walk around the island.