$646,248Average Value$546Average Price per Sq Ft8Homes For Sale
Small-town, waterfront living in Cottage Hill
Cottage Hill is a peaceful New England beach town in Winthrop, surrounded by ocean views and populated by historic homes. Only about 7 miles from the heart of Boston, residents here can indulge in city life by day and come home to a waterfront oasis by night. “We call it the best-kept secret on and offshore,” says Emilie DiMento, a partner at Cottage Hill Real Estate in Winthrop. Everyone in the Winthrop area lives within walking distance of the beach, making this sleepy town an ideal spot for those interested in outdoor activities on water or land. “What you find here is a group of people and neighbors who are knowledgeable, supportive of each other and have a deep appreciation of the traditions, while also welcoming in anybody who would like to join the community,” DiMento says. One emblem of the neighborhood’s fortified community is the formation of organizations that continuously improve the area. In 2004, the Viking Pride Foundation was born, working to foster opportunities for Winthrop students and provide funds for various clubs and activities. Homebuyers choose Cottage Hill for its recreation, inclusive population, striking views and convenience.
Massachusetts beaches and Massa Playground
One of the biggest draws to the neighborhood is beach access, and Cottage Hill residents can hit Winthrop Beach along the eastern side of the peninsula or Yirrell Beach, a bit farther south. From the sandy and rocky tract, visitors can catch views of the ocean, and lifeguards are on duty during the summer. The west side of Cottage Hill opens up into Crystal Cove, a stretch of coastline that includes the Winthrop Yacht Club’s marina, with over 160 boat spots, and Winthrop Town Landing, which features docks, a public boat ramp and a pier. Another outdoor gathering space can be found at Massa Playground, which is an enclosed park with a jungle gym and basketball courts.
Welcome to Winthrop Beach in Cottage Hill, Winthrop, MA.
Rederick W. Yirrell Jr. Beach is a well-liked beach in Cottage Hill, MA.
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Clusters of condos in Cottage Hill
The homes sandwiched between the shoreline were mostly built in the 19th and 20th centuries, and many houses have colonial-inspired architecture with modern renovations. DiMento says that “there’s been a tremendous amount of retrofitting and modernizing,” but homes maintain their historic facades. Condos dominate the housing market here, with options in both multifamily or duplex homes and complexes. Less than half of the neighborhood opts to own, and renters often pay between $2,000 and $3,000 per month for one- and two-bedroom units. Homes typically sell between $500,000 and $1 million, but one-bedroom condos can start under $200,000. Many houses feature front porches and balconies, and while not every property has a backyard, Massa Playground is within walking distance. Streets here can be curved and steep, though sidewalks line most roads, making it a walkable area. Many of the property transactions here are between relatives, keeping many local families in Cottage Hill for generations.
A stunning coastal home in Cottage Hill, MA.
A coastal multi-family building located in Cottage Hill in Massachusetts.
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Winthrop Chamber of Commerce hosts Cottage Hill events
Residents come together for annual events, such as the Winthrop Town Wide Yard Sale and the Winthrop Family Beach Day at Yirrell Beach. The neighborhood also has festive celebrations, including the Boos & Brews and Winthrop Holiday Lighting traditions. The Winthrop Chamber of Commerce is a major sponsor for events in the area.
Dining on Shirley and heading north for shopping
Restaurant options are available within close walking distance along Shirley Street, which is on the western side of the neighborhood, north of the yacht club. Ferrante’s is one notable spot, specializing in steaks and seafood, while Selva Coffee House is a daytime destination for breakfast. DiMento mentions that Cafe Delite, in the center of Winthrop, is a popular option for those who choose to drive into town. Winthrop Marketplace is also in town and is locally and family owned. It is a neighborhood staple for groceries, baked goods and other everyday necessities. Target is available within about 4 miles in Revere for those who do not want to travel into Boston for a big-box department store. Health care is also available outside of the city at MGH-Revere HealthCare Center.
Swing by Selva Coffee House in Cottage Hill for a hot cup of coffee on a cold day.
The Winthrop Marketplace in Cottage Hill has all your pantry staples for a grocery run.
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Public education in Cottage Hill
Students here are zoned for Winthrop Public Schools, beginning at Arthur T. Cummings Elementary, which earns a B-minus on Niche. Children can then head to Winthrop Middle and High Schools, which both score B grades. This school pipeline is accessible, sitting within 1 or 2 miles of Cottage Hill residences. The middle and high schools share a campus and collectively offer over 25 sports teams.
The Arthur T Cummings School has an overall grade of B- on Niche.
Multiple electives and the performing arts are all offered at the Winthrop High School.
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Cottage Hill transportation options from the MBTA to BOS
Cottage Hill is just a few miles east of Massachusetts Route 1A, which can be used to commute 7 miles south into Boston. Many residents choose to work in Boston, and the drive typically takes about 20 minutes. Massachusetts Bay Transportation Authority (MBTA) has bus stops in Winthrop that lead to the Blue Line subway route into the city. For air travel, residents are just about 5 or 6 miles from Boston Logan International Airport (BOS).
The Blue Line and several bus lines run nearby Cottage Hill and can get you around easily.
A quick bus or scooter ride from Cottage Hill will get you to Orient Heights on the Blue Line.
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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to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Cottage Hill
US
Homicide
3
4
Sexual Assault
2
4
Assault with Weapon
2
4
Robbery
2
4
Burglary
2
4
Motor Vehicle Theft
2
4
Larceny
2
4
Crime Score
1
4
Source: WhatIsMyCrimeRisk.com
Cottage Hill Demographics and Home Trends
On average, homes in Cottage Hill, Winthrop sell after 49 days on the market compared to the national average of 56 days. The median sale price for homes in Cottage Hill, Winthrop over the last 12 months is $490,000, down 6% from the median home sale price over the previous 12 months.
Coastal living at its best! Just steps from the beach, this beautifully maintained 2-bedroom, 1-bath condominium offers the perfect blend of charm, comfort, and convenience. The bright, open-concept living and dining area flows seamlessly into a spacious kitchen featuring rich cabinetry, granite countertops, and large penninsula—ideal for entertaining. A sun-filled enclosed porch provides the
566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been
Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to
Welcome to The Cove, a distinguished condominium community in coastal Winthrop, offering a spectacular seaside setting with the Boston skyline as the backdrop for unforgettable sunsets. This renovated second-floor studio features wood flooring throughout, an updated kitchen with dining space, and a private balcony off the living area. The unit includes a modern bathroom with a walk-in shower,
Enjoy coastal living in this charming waterfront condominium in Winthrop, offering the perfect balance of convenience and seaside lifestyle. Located just minutes from Boston Logan Airport and with easy access to public transportation including nearby bus routes, the Orient Heights MBTA station, and the East Boston ferry, this home is ideal for commuters seeking quick access to Boston while
8**Back on market due to out of state sale contingency falling through*** WELCOME TO WINTHROP BY THE SEA! THE COVE AT 600 SHIRLEY WAS CONVERTED IN 2022 AND IS LOCATED ON THE SITE OF THE HISTORIC CRYSTAL COVE HOTEL AND HAS AMAZING VIEWS OF BOSTON AND THE ATLANTIC OCEAN! WALK TO THE BEACH, THE YACHT CLUB, VARIOUS RESTAURANTS AND PARKS. THIS 1 BEDROOM UNIT FEATURES NOT ONE BUT TWO BATHROOMS AND 2
Welcome to 16 Underhill Rd. #3, a beautifully updated 3-bedroom, 1-bath condo offering 1,036 sq. ft. of move-in ready living space. This bright and inviting home features modern updates, a functional layout, and private laundry in the basement for added convenience. Enjoy your own private deck, perfect for relaxing or entertaining. The property also includes a private garage plus ample additional
This like-new 2-bedroom, 2 bath condo at 34 Underhill Street delivers the finish level of new construction at a fraction of the cost. Gut renovated and converted in 2020, every detail was approached with care, from the white shaker kitchen with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including gas cooking, to the wide plank hardwood floors
2nd floor walk-up, this studio condominium is for lease starting Sept. 2026. A former waterfront hotel in Winthrop, MA, The Cove, is renovated and modernized. Here is the opportunity to live across the Bay from Boston; Logan Airport is accessible by public transportation. Excellent commuter location or landing-pad! Unit 9 is available either Unfurnished, or Furnished, with a queen-sized bed
Enjoy your morning cup of coffee looking at the ocean from your private 2nd floor deck. New kitchen! New Bathroom! New everything! In unit laundry. Off street parking available. Winthrop 2+ Bed with a large top level loft space. Watch the sunrise and enjoy evening walks to the beach half a block from your front door. Marble countertops & tile floors in the kitchen/bath. Multiple spaces for bright
Bright, updated 2-bedroom, 2-bathroom unit available at 35 Perkins Street in sought-after Winthrop. The unit features an updated kitchen with stainless steel appliances, two full bathrooms, and in-unit washer/dryer. Hardwood floors and thoughtful updates throughout make this a true turnkey rental. Three houses from Winthrop Beach with dining and local shops at your door. A 6-minute walk to
Absolutely huge apartment for rent that feels like a single family. This home on Tewksbury street is located between the ocean and harbor with prime east to west natural light all day. This home has a private entrance to the unit which boasts 4 large bedrooms, 2 bathrooms along with brand new gas heating system and new windows. 2 KITCHENS IN THIS HOME! Full Living Room, Dining Room, Multiple
A waterfront living in the heart of Winthrop Harbor. This beautifully renovated ground-level apartment offers 3 bedrooms, 2 full bathrooms, and approximately 1,000 square feet of living space with breathtaking harbor, ocean, and city views. Features include hardwood flooring, updated kitchen with newer appliances, dishwasher, heat and hot water included, and a private ground-level patio
Live the waterfront lifestyle year-round in this bright 2-bedroom, 1-bath Penthouse overlooking three marinas! Gorgeous harbor views from every room, renovated kitchen with island and stainless appliances, open floor plan, abundant natural light, hardwood floors, exposed brick, and a spacious master bedroom with sitting area. Heat and hot water included, plus large storage and laundry in the
360 OCEAN and CITY VIEWS. Sip your morning coffee and take in the ocean breeze on the rooftop porch and watch the sunset . Completely renovated 4 full bedrooms, 2.5 full bathrooms, with bonus space for an office.3 floors of living space featuring an open kitchen and living room and area for formal dining room. Water views from literally every window . Gleaming hardwood floors throughout. Stunning
Available June 1st! Spacious and recently renovated 3-bedroom apartment located on Shirley St. This unit features new vinyl flooring throughout, stainless steel appliances, and Central A/C & Heat for year-round comfort. Enjoy beautiful water views right from your porch! Conveniently located just minutes from Winthrop Beach and Deer Island, with easy access to public transportation and bus stops
Location,location,waterfront 1 bedroom apartment. Watch the sun rise from your spacious living room or enjoy your morning coffee. Gleaming hardwood floors throughout, ample closet space. Full tile bathroom with bathtub and linen closet. Stackable washer and dryer for tenant use. Open floor plan from dining room to living room. This apartment includes all utilities except cable. There is 1 car
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