$775,689Average Value$497Average Price per Sq Ft13Homes 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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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
Are you familiar with the Winthrop Highlands neighborhood?
to let others know what life in this neighborhood is like.
Winthrop Highlands Demographics and Home Trends
On average, homes in Winthrop Highlands, Winthrop sell after 37 days on the market compared to the national average of 55 days. The median sale price for homes in Winthrop Highlands, Winthrop over the last 12 months is $609,500, down 9% from the median home sale price over the previous 12 months.
Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths,
A rare offering at the prestigious Seal Harbor III, this exceptional corner residence captures breathtaking panoramic water views from an expansive, light filled interior and a private balcony - perfect for enjoying morning coffee, evening sunsets, or simply taking in the every changing waterfront scenery. Completely reimagined with a full gut reno in 2010, the home showcases timeless design, an
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
Second-floor home in the heart of Winthrop, a short walk to the beach, parks, and the golf course. This three-bedroom condominium pairs 1920s character with modern updates. The living and dining rooms feature hardwood flooring, natural woodwork, and built-ins, with bay windows bringing in natural light throughout. The kitchen offers granite counters, stainless steel appliances, a breakfast bar,
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
Imagine coming home to the relaxed rhythm of coastal living, where the water is just moments away and the best of Winthrop is right outside your door. This beautifully renovated 2-bedroom, 2-bath condominium has been thoughtfully transformed into a stylish and welcoming retreat, offering partial water views and a fresh, move-in-ready interior. Enter to warm hardwood floors that flow throughout
Waterfront Living at Its Best! Enjoy breathtaking ocean views from this spacious 8th floor condominium offering 974 sq ft of comfortable living space. Relax on your private balcony overlooking the water, or good size bedroom including a large walk-in closet and a separate tub/shower room. This full service building offers outstanding amenities, including concierge service, an oceanside heated
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
Owner has relocated! Now is your chance. 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
Experience elevated waterfront living in this stunning 3 bedroom, 3 bath penthouse at the prestigious Seal Harbor III. This exceptional two-level residence features a spacious open-concept floor plan designed to maximize natural light and showcase its spectacular waterfront setting. Entertain effortlessly or simply relax on the massive private deck, offering the perfect space to enjoy ocean
Sixth-floor waterfront living at Seal Harbor in Winthrop Highlands. This 2-bedroom, 2-bath condo offers 1,203 square feet of single-level living with brand new hardwood floors throughout and direct ocean views from the main living space. The living and dining rooms flow together in an open layout, with a slider out to a private balcony where the water views are the main event morning and night.
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 on-street.
Winthrop, MA (Highland Area) - Spectacular Ocean/Waterfront 4 Bedrooms, 3.5 Baths, 4 Levels Townhome For Rent, Available September 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.
Winthrop, MA (Highland Area) - Spectacular Ocean/Waterfront 4 Bedrooms, 3.5 Baths, 4 Levels Townhome For Ren; 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; Townhouse Features 3 Spacious
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
