$767,618Average Value$507Average Price per Sq Ft11Homes 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.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
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Crime and Safety
1 - Low Crime, 10 - High Crime
Winthrop Highlands
US
Homicide
4
4
Sexual Assault
3
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
2
4
Motor Vehicle Theft
2
4
Larceny
2
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
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 56 days. The median sale price for homes in Winthrop Highlands, Winthrop over the last 12 months is $660,000, consistent with the median home sale price over the previous 12 months.
Custom built in 2021, 38 Nahant Avenue was put together with real attention to detail and the finishes back it up. This home runs on Savant for full smart home control, plus Ring cameras for security. The kitchen is built around a full Thermador appliance package, including three Thermador columns: a full fridge, a full freezer, and a wine fridge. The exterior is Hardie plank with a 7 inch
Turnkey corner PENTHOUSE unit in Seal Harbor with $5k credit if UAG by 7/20! Offering sweeping Atlantic Ocean views from a private top-flr balcony this 2023 renovated 2BR/2BA residence showcases oversized windows that flood the living area with natural light, built-in window seat, white oak HW floors throughout, and an elegant inlay foyer detail beneath skylight/ recessed lighting. Updated
Seal Harbor I Gorgeous ocean views from this sunny corner 8th-floor unit. Spacious living room with slider to a private balcony-This home features two comfortable bedrooms with large closets and beautiful views, a well-appointed kitchen with ample cabinetry and updated appliances, plus a newer washer/dryer. Enjoy resort-style amenities including an in-ground heated pool, fitness area, and a
Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and reimagined coastal home has been recently completed. The home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive
Welcome to coastal living at its finest at the highly desirable Seal Harbor One. Perched on the fourth floor, this spacious and thoughtfully designed 2-bedroom, 2-bath residence offers an ideal layout with private bedroom suites, each featuring its own full bathroom and generous walk-in closet. Set on a stunning peninsula surrounded by the Atlantic Ocean, Seal Harbor offers a truly unique
Wonderful opportunity to own a coastal Winthrop home with tremendous potential. A welcoming mudroom opens to a spacious foyer and a large living and dining area with great flow for everyday living. A bonus front room offers flexible space for a home office, playroom, or an expanded open-concept layout. The kitchen leads directly to the back deck for warm-weather entertaining. Upstairs features
Rarely available corner unit at the ultra desirable Seal Harbor Condominiums. Enjoy sweeping views of the Atlantic Ocean and beyond from the comforts of your own living room. This two-bedroom, two-bath unit boasts oversized windows and glass sliders with unobstructed ocean views and great natural light, hardwood floors, updated kitchen and bath, in-unit laundry hook-ups, extra storage space and a
OPEN HOUSE CANCELED! Welcome to the Highlands, where coastal living meets modern comfort. This beautifully maintained single-family offers water views, thoughtfully updated living spaces, and the flexibility today's buyers desire. The sun-filled main level features gleaming hardwood floors throughout, an upgraded kitchen, and an open layout that flows seamlessly to the spacious rear deck
Wake up to SPECTACULAR SUNRISES over the Atlantic and fall asleep to the soothing sound of OCEAN WAVES in this affordable OCEANFRONT UNIT at Seal Harbor Condominiums! Offering UNOBSTRUCTED OCEAN VIEWS from EVERY ROOM, this beautifully maintained home delivers the ultimate coastal lifestyle while being a short drive to Boston & Logan Airport! Gleaming HW FLOORS flow throughout the OPEN CONCEPT
Experience refined waterfront living in this fully renovated, ocean-facing residence. The chef’s kitchen is a true centerpiece, featuring a brand-new center island, quartz countertops, and premium appliances—perfect for effortless entertaining. Modern upgrades shine throughout, including new electrical, recessed lighting, and sleek ceiling fans. Relax in the spa-inspired bathroom with a walk-in
No broker fee! On one of the best streets in town in the highlands rests this oversized first floor apartment. This apartment has 3 bedrooms, large kitchen, living room and dining room, and even a front deck that overlooks the ocean! Newly renovated kitchen, exclusive use washer/dryer, new gas boiler, plenty of street parking and storage make this a great place to call home!Walk to some
Winthrop, MA (Highland Area) - Spectacular Ocean/Waterfront 3 Bedrooms, 3.5 Baths, 4 Levels Townhome For Rent, Available Sept. 1, 2026; Property Easily Accessible To shopping And Dining, Less Than 10 Minutes’ Drive To Orient Heights And Beachmont (MBTA) Blue-Line Train Services To Downtown Boston, 15 Minutes’ Drive To Logan International Airport, And 27 Minutes To Encore Boston Harbor Casino;
Welcome to beautiful Winthrop by the Sea! This ocean front, one bedroom basement apartment in the desirable Winthrop Highlands neighborhood is perfect for an individual. It contains a spare room that can be an office or den. Living room, kitchenette and full bath in excellent condition. Large bedroom with window AC unit. Tile floors throughout. Includes one parking spot on driveway and off
Enjoy easy coastal living in this beautifully maintained second-floor 2-bedroom, 1-bath apartment located in the highly sought after Winthrop Highlands neighborhood. Just moments from the ocean, beaches, local restaurants, and parks, this home offers the perfect combination of comfort, convenience, and seaside charm. The spacious layout features hardwood flooring throughout, a bright open-concept
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