$765,301Average Value$513Average Price per Sq Ft7Homes For Sale
Beautiful waterfront views, tight-knit community
In a quaint, beach-dotted town that has been described as the area’s best-kept secret, Winthrop Highlands still stands out. This is partially because of its geography—jutting out into the ocean, bounded by water on three sides. “It’s a beautiful area,” says Linda Calla, a real estate agent at Cottage Hill Real Estate who has sold in the Winthrop area for 39 years and lived there for over 55 years, raising her sons in the community. “It’s along the Atlantic coastline, the houses along the water are absolutely breathtaking.” The area’s natural beauty is a major draw for many homebuyers, offering both sunrises and sunsets over the water. “Not only are the sunrises amazing but you can occasionally see the full moon rise over the horizon,” says Sharon Tallent, a Realtor with the Highland Group at Compass and a member of the community. In recent years, the town has been noticed for what it has to offer. “It’s a very close-knit community. It’s very artsy, we have a lot of very talented artists in town. We even have our own art gallery,” Calla says. “You’ll meet all kinds of different people. It’s a great place to live. When people move here, they see that, and they fall in love with the town.”
A waterside home with decks has views of Boston yet is located in Winthrop Highlands.
Near Winthrop Highlands is Deer Island with lots of amenities for visitors and residents.
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Halford and Highlands beaches
“If you’re a boater or fisherman, if you just love the beaches, you love to walk, jog, run, it’s great,” Calla says. “We have surfers. We have an active sailing program for the kids at the yacht clubs.” Halford Beach and Highlands Beach sit on opposite sides of the neighborhood, providing water access close to home for nearly everyone. Fort Heath Park, right in the middle of Winthrop Highland’s coastline, is situated on what’s known as Grovers Cliff along the water, making it a popular place for locals to run or walk their dogs alongside stunning views. “Sometimes they have concerts in the park,” Calla says. “Other times you might see a wedding.” Pond Street Playground offers a playground and basketball courts, and the John Joseph Kilmartin Pathway is a popular walking trail. Although there are none in Winthrop Highlands, Tallent and Calla both note that Winthrop has three marinas and three yacht clubs. Nearby, Winthrop Beach is particularly popular, and locals drive 2 miles to the Belle Isle Marsh Reservation to hike among its 28 acres of beautiful marshland.
Halford Beach sits on the west side of the Winthrop Highlands neighborhood.
Winthrop Highlands, Highland Beach, offers a walkway along the coast.
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Homes near the water
Although the town as a whole is generally pretty quiet thanks to a lack of through-traffic, Calla says, Winthrop Highlands is even more so. There are a couple of high-rise condominiums on the neighborhood’s point, but most of its peaceful, well-established streets are full of historic single-family homes that vary from Cape Cods and colonials to the occasional Victorian. Most were built around the turn of the 20th century. Compared to other parts of town, the neighborhood features slightly bigger lots. “It’s really more spread out,” Calla says. Home prices in Winthrop Highlands can range from about $550,000 to more than $1 million. Being a small town, Tallent says, “we seldom have lots of inventory,” leading to competition for homes.
There are new construction homes located in the Winthrop Highlands neighborhood.
In some areas, the beaches of Winthrop Highlands are wide and are home to large beach villas.
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The traditional Horrible’s Parade
According to Calla and Tallent, Winthrop hosts a lot of events throughout the year, including a Christmas tree lighting ceremony, music festivals, a family beach day and a huge Fourth of July event. In Winthrop, the patriotic holiday involves a 140-year-long tradition called The Horrible’s Parade. “Different groups build floats, they dress in different themes, and then at the end of the parade, there’s a committee that votes which one is the most beautiful, the most patriotic, the most horrible,” Calla says. “And then we have an event at the park with food and music and races for the kids.”
Chicken pot pie at The Winthrop Arms Hotel
Locals drive just outside the neighborhood to pick up groceries at Winthrop Marketplace, but when they don’t feel like cooking, the local restaurant scene is on point. The Winthrop Arms Hotel and Restaurant is one spot visitors must check out, Calla says, noting that it’s particularly well-known for its chicken pot pie. “The food is delicious and they have a nice bar, it’s very cosmopolitan,” Calla says. Locals also enjoy starting their days at Jac’s Café, heading to Antique Table Restaurant for an Italian dish or snag takeout from Bridges Nepali Cuisine.
Do yourself a favor and enjoy the chicken pot pie from Winthrop Arms in Winthrop Highlands.
Spend your afternoons or evenings with the company at Winthrop Arms Restaurant.
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Niche gives Winthrop Public Schools a B-plus
Children can attend the William P. Gorman Fort Banks Elementary School, which Niche gives an A-minus and lists as the second-best public elementary school in Suffolk County. Children then attend Winthrop Middle School and Winthrop High School, both of which have B ratings and make Niche’s list of the top 10 public middle and high schools in Suffolk County, respectively. Winthrop High has a student-to-teacher ratio of 13 to 1 and strives to make its students enthusiastic lifelong learners.
William P. Gorman/Fort Banks Elementary School has an overall rating of A- on Niche.
Multiple electives and the performing arts are all offered at the Winthrop High School.
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Commuting to Boston by highway or ferry
Revere Street, also known as U.S. Route 145, makes up one of the neighborhood’s borders. Following it takes residents to Downtown Boston just 10 miles away, but commuters can also get there by the ferry located less than 2 miles from Winthrop Highlands. This option is particularly helpful, Calla says, when the tunnel is under repair. It’s just over 5 miles from Boston Logan International Airport.
Suffolk Downs is a quick bus ride from Winthrop Highlands and can get you into Boston quickly.
There is no shortage of public transportation in and around Winthrop Highlands.
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Winthrop Highlands Demographics and Home Trends
On average, homes in Winthrop Highlands, Winthrop sell after 42 days on the market compared to the national average of 53 days. The median sale price for homes in Winthrop Highlands, Winthrop over the last 12 months is $660,000, down 8% from the median home sale price over the previous 12 months.
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