$645,909Average Value$523Average Price per Sq Ft4Homes 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
Interested in learning more about homes in this area?
Reach out to
Virginia Todd,
an experienced agent in this neighborhood.
Parks in this Area
Massa Playground
Basketball
Playground
Ingleside Park
Coughlin Park
Pond Street Playground
Basketball
Tennis
Playground
Crest Avenue Park
Trails
Playground
Highlands Beach
Trails
Transit
Airport
General Edward Lawrence Logan International
13 min drive
Bus
Shirley St Opp Crystal Cove Ave
Bus
Shirley St Opp Moore St
Bus
Shirley St & Pontos St
Bus
Shirley St & Petrel St
Bus
Washington Ave Opp Veterans Rd
Crime and Safety
1 - Low Crime, 10 - High Crime
Cottage Hill
US
Homicide
3
4
Sexual Assault
2
4
Assault with Weapon
3
4
Robbery
4
4
Burglary
3
4
Motor Vehicle Theft
4
4
Larceny
3
4
Crime Score
3
4
Source: WhatIsMyCrimeRisk.com
Demographics and Home Trends
On average, homes in Cottage Hill, Winthrop sell after 41 days on the market compared to the national average of 47 days. The average sale price for homes in Cottage Hill, Winthrop over the last 12 months is $530,200, down 14% from the average home sale price over the previous 12 months.
WATER VIEWS & PRIVATE DECK! Welcome to The Cove at 600, a premier condominium development in Winthrop, situated on the historic site of the Crystal Cove Hotel. This meticulously renovated first-floor unit features 1 bedroom and 2 baths, epitomizing perfect beach town living. Every detail has been updated finishes, including newer kitchen & bathrooms. Your living room offers stunning water views,
Enjoy breathtaking water and Boston skyline views from this beautifully renovated 2-bed, 2-bath condo at the former Historic Crystal Cove Hotel. Offering first-floor convenience with a private entrance and two deeded parking spaces right outside your door, this home lives like a private residence. The open layout features engineered hardwood floors, in-unit laundry, and a stunning private deck
Elizabeth CrowleyWilliam Raveis R.E. & Home Services
GREAT INVESTMENT OPPORTUNITY OR OWNER OCCUPY......Why rent when this 2 bedroom updated unit can give you a start in homeownership? Conveniently located on the Bus Line to the Blue Line and looking out to the harbor and Lewis Lake with just steps to the ocean! Yes, the beach is at the top of the street. This top floor unit has hardwood floors throughout, pretty set of windows in the living
“The Cove at 600” was converted in 2022 and is located on the site of the historic Crystal Cove Hotel with breathtaking views of the Boston Skyline and the Atlantic Ocean. Unit 3, located on the side of the building with a private entrance, exclusive use patio and exclusive use deck at the front of the building offers many ways to take in the view and the sea air. The open concept living room and
Erika Leigh PereiraGibson Sotheby's International Realty
If you haven't already found this hidden gem, it's time to discover Winthrop by the sea. This updated 3 Bedroom 1.5 Bathroom home is just what you're looking for as the Summer approaches. This 2 floor single family home is a commuters dream. Minutes from downtown Boston. Steps to the beach, bus stop and Ferry. Sit on the back deck and enjoy the view of the Boston skyline. Available May 1st.
Welcome to 585 Shirley St unit 2 available May 1st, 2025, just in time for the amazing oceanside summer festivities!! Fully renovated two bedroom, one-bath waterfront in Winthrop. We are located within walking distance to restaurants, Winthrop Ferry and the MBTA Public transportation. A common area boasts even more fun with alluring views of the Winthrop Harbor, Marina and Boston skylines. HEAT
Interested in learning more about homes in this area?
Reach out to
Virginia Todd,
an experienced agent in this neighborhood.
Average Home Value
Source: Public Records
Property Mix - Square Feet
This Neighborhood Has Equal Renters and Owners
Demographics
Total Population
1,092
Median Age
44
Population Density
15 ppl/acre
Population under 18
18.8%
Below the national average
23.8%
Population over 65
19.5%
On par with the national average
19.1%
Finances
Median Household Income
$113,306
Significantly above the national average
$71,702
Average Household Income
$121,508
Education and Workforce
High School Graduates
96.2%
College Graduates
45.8%
Above the national average
34.1%
Advanced Degrees
21.7%
Above the national average
13.3%
% Population in Labor Force
73.2%
Weather
Annual Precipitation
43''
Average Winter Low Temperature
23°F
Average Summer High Temperature
82°F
Annual Snowfall
12''
Area Factors
Somewhat Bikeable
Bike Score®
17/ 100
Somewhat Walkable
Walk Score®
54/ 100
Source: Walk Score
Source: Walk Score
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
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.
