$689,233Average Value$470Average Price per Sq Ft16Homes For Sale
Coastal living in the heart of Winthrop
Part of a peninsula town on the Atlantic Coast that sits about 6 miles east of downtown Boston, Downtown Winthrop is outlined by pristine ocean shores, docks and marinas, creating a community that's oriented by its coastal lifestyle. Nautical homes with ocean views and properties within minutes of the beach are prime attractions for homebuyers, and the town’s proximity to Boston is convenient for commuters. “Lots of people come to town looking for waterfront properties,” says Elizabeth Ferrara, local Realtor and partner at Cottage Hill Real Estate with 13 years of experience. “Winthrop has lots of sailing programs and many marinas and beaches; it has a nice beach town feel here.”
Large homes are found along the coast, waterfront of Downtown Winthrop.
There is no shortage of placing to launch your boat in Downtown Winthrop.
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Historic waterfront homes in Downtown Winthrop
Peaceful beach cottages, Cape Cods and colonial-inspired homes sit close together on Downtown Winthrop’s established streets. Single-family houses are often alongside multi-family properties, condos and some multi-use or commercial storefronts. While some homes can date from the early 1800s to the present day, most properties were built between the 1850s and 1950s. Lot sizes usually fall between 3,000 and 7,000 square feet, with occasional waterfront estates having over three-quarter acres of yard space. “There are lots of condo conversions here from multi-family properties,” Ferrara says. “Single-family homes go between $700,000 to $1.2 million, and multi-families can go from $600,000 to $1.1 million. Waterfront properties are definitely priced higher, but they are still really hard to come by.” Condos typically start at $300,000 and can fetch $800,000 if they offer ocean views. Homebuyers may be required to purchase flood insurance for properties in designated flood zones.
Colonial style homes can be found throughout Downtown Winthrop.
Smaller homes are also found throughout Downtown Winthrop.
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From yacht clubs to public parks
As a coastal community, downtown Winthrop is surrounded by beaches, marinas and yacht clubs. Residents are often out walking along the shores of Donovan’s Beach or Winthrop Beach while watching planes flying in and out of Logan International Airport. In the warmer seasons, after people go boating and sailing, they usually park their boats at one of the many marinas in town. Yacht clubs such as Winthrop Yacht Club and Pleasant Park Yacht Club not only serve as social venues for community members, but also offer activities such as youth and adult sailing instructions and programs. Winthrop Golf Club opened in 1917, featuring a nine-hole course that’s open to the public on Mondays. Community events such as the local farmers market take place at Ingleside Park, which also has a skate park, tennis courts and a baseball field. Fort Banks Elementary School has a soccer field often used for games and practices.
Winthrop Beach is known for it's proximity to Boston but also for being a warm coastal town.
Locals can walk through the Nerio pathway as they enjoy the sunset falling on Belle Isle Marsh Marine Ecology Park.
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Historic waterfront restaurants that anchor the community
Belle Isle Seafood is a popular waterfront restaurant with classic New England fare. People can enjoy fresh seafood entrees while watching planes take off against the Boston skyline. The Winthrop Arms Hotel and Restaurant is a historic hallmark that overlooks the Atlantic Ocean. “The place dates back to 1916,” Ferrara says. “When you step inside you feel like you are going back in time. It was beautifully renovated recently, and people from all over come to Winthrop specifically to see this establishment.” The restaurant is known for its signature chicken pot pie and other American dishes. For fine dining, Vuolo's is an independent Italian eatery with a cosmopolitan atmosphere, and Nick’s Place is the area’s staple pizzeria. For groceries, Winthrop Market Place sits in the center of the community on Revere Street. About 2 miles north in Revere, The Shops at Suffolk Downs is a shopping mall home to Target, Stop & Shop, local businesses and chain restaurants.
Nick's Place in Winthrop has some of the best sandwiches in town.
Grab some dinner with friends at Belle Isle Seafood in Downtown Winthrop.
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Winthrop Public Schools
The community is served by Winthrop Public Schools, which has an overall B Niche grade and a student-teacher ratio of 13-to-1. Young learners may begin schooling at the A-minus rated William P. Gorman Fort Banks Elementary School, which serves students from prekindergarten to second grade. The B-minus rated Arthur T. Cummings Elementary School is for students in grades three to five. Winthrop Middle School and Winthrop High School both score a B and are rated by Niche as the No. 11 best public middle and high school in Suffolk County. “Most public schools here are brand new schools built in the last 20 years with state-of-the-art classrooms,” Ferrara says. “It’s a small town, so the class sizes are also small.”
WHS's core values are Perseverance, Respect, Intelligence, Determination, and Excellence.
Winthrop Middle School has an overall grade of B on Niche.
William P. Gorman/Fort Banks Elementary School has an overall rating of A- on Niche.
The Arthur T Cummings School has an overall grade of B- on Niche.
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Century-old traditions in Winthrop
There are many community events in Winthrop, including an Independence Day celebration featuring The Horrible’s Parade, a long-held tradition for over 140 years. The town also has an annual Strawberry Festival that dates back to 1912. Highlighting the signature strawberry shortcake, the event includes free tours of the Deane Winthrop House Barn, raffles, live performances, family friendly activities and strawberry daiquiris for adults. Additional events include a lighting ceremony for winter holidays and waterfront concerts such as Music on the Landing.
Pick up some jewelry for the perfect gift at the annual Christmas Fair in Downtown Winthrop.
Downtown Winthrop is a great area to go fishing or boating nearly any time of the year.
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Transit options for access to Boston
Winthrop sits adjacent to Boston Logan International Airport, which is often an easy 4-mile drive for residents when they need to travel by air. The town is also about 6 miles east of downtown Boston, which can be accessed via Massachusetts Route 1A. Commuters can also head to nearby Orient Heights for the MBTA T subway lines, or opt for the ferry service at Winthrop Landing between May and October. “Winthrop’s proximity to the city attracts many people,” Ferrara says. “People can get to Boston without ever touching the highway.” Paul Revere Transportation, subsidized by the MBTA, also operates several bus routes in Winthrop. MGH-Revere HealthCare Center, a general hospital in Revere, is 3 miles north.
Commuting to and from Winthrop is a breeze on the Blue Line.
Orient Heights is a nearby train station with lots of bus options for Winthrop residents.
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 Downtown Winthrop neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Downtown Winthrop
US
Homicide
3
4
Sexual Assault
2
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
3
4
Motor Vehicle Theft
3
4
Larceny
3
4
Crime Score
2
4
Source: WhatIsMyCrimeRisk.com
Downtown Winthrop Demographics and Home Trends
On average, homes in Downtown Winthrop, Winthrop sell after 38 days on the market compared to the national average of 56 days. The median sale price for homes in Downtown Winthrop, Winthrop over the last 12 months is $602,450, down 4% from the median home sale price over the previous 12 months.
$2,500 bonus to buyer or buyer broker* Exceptional opportunity to live where you work. Corner lot with off-street parking, this unique property offers endless possibilities for investors, developers, or owner-occupants.The ground level features professional office space complete with a reception area, conference room, workspace, and 1/2 bath. Also included is a vacant 2-level, 2-bedroom, 1.5-bath
Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience
LAST STUDIO AVAILABLE! Discover effortless coastal living at Unit 304 at The Somerset, a boutique condominium community ideally located in the heart of Winthrop. This well-appointed studio offers a bright and airy open layout designed for both comfort and functionality, featuring a flexible bonus room with a sliding barn door ideal for a home office, guest room, or additional living space. The
Charlesgate New Development TeamCharlesgate Realty Group, llc
Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where
Stunning 2022 rebuild—taken down to the original foundation and rebuilt with a fresh, nearly-new feel throughout! This townhome-style condo feels like a single-family, nearly 2,000 sq ft, featuring 3 beds, 3 full baths, private outdoor space, and 2-car parking. NO monthly condo or HOA fees; annual master insurance just $1,670. A standout alternative to East/South Boston with quick Downtown Boston
Start your homeownership journey at Unit 402 at The Somerset, a bright and spacious top-floor 2-bedroom, 2-bath condo in the heart of Winthrop. Designed for modern living, this move-in-ready home features an open-concept layout, two private balconies, quartz countertops, stainless steel appliances, central A/C, and generous closet space. Garage parking is included, along with access to an
Charlesgate New Development TeamCharlesgate Realty Group, llc
Welcome to The Somerset, this thoughtfully designed 2-bedroom, 1-bath residence blends modern comfort with coastal charm. The open-concept layout offers an inviting living and dining area, complemented by a stylish kitchen featuring quartz countertops, stainless steel appliances, and contemporary finishes. Central A/C, abundant natural light, and quality craftsmanship create a comfortable and
Charlesgate New Development TeamCharlesgate Realty Group, llc
Welcome home to this pristine and exceptionally well-kept two-bedroom, one-bath condominium in the heart of Winthrop’s vibrant 02152 community. This inviting home offers comfortable living along with private outdoor space—perfect for relaxing, entertaining, or enjoying coastal breezes. Conveniently located with easy access to Orient Heights, major highways, Logan Airport, and downtown Boston. The
Welcome to Unit 309—a bright corner 1-bedroom, 1-bath home featuring an open-concept layout, high-quality finishes, and a relaxed coastal style. The kitchen features stainless steel appliances, quartz countertops, central A/C, and modern design touches throughout. Residents enjoy elevator access, a fitness room, and a stylish common area—perfect for relaxing or savoring a morning coffee. Ideally
Charlesgate New Development TeamCharlesgate Realty Group, llc
MAJOR NEW RENOVATION IN 2023.......EXCITING 2 BEDROOM, 2BATH UPSCALE CONDOMINIUM AT WINTHROP CENTER. Stunning oak floors and state of the art quartz and stainless kitchen, fully applianced with subway tile accents and an over sized island with pendant lighting. All open to a generous living area and access to an exclusive deck for personal outdoor space. A beautiful main suite with an amazing
Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces giving warmth & charm to the living spaces. Extensive updates include all new mechanical systems including elec. wiring, FWA
***Seller is VERY motivated***Welcome to your fully renovated and updated home on a quiet corner in Winthrop. This home features a brand new kitchen with wide spanning island, open to the living room. Perfect for entertaining. All new electrical, water heater, furnace, plumbing, insulation and hard wired fire alarms. Approximately 250 sqft was added on and 2 bathrooms were also added making this
Winthrop, MA - Nice Two Bedrooms Ground Level Condo For Rent With Heat And Hot Water Included In The Rent. Available Now, 2026. FEATURES: Kitchen With Stainless Steel Appliances (Stove, Refrigerator, Dishwasher), Quartz Countertop; Ceramic Title And Pergo Hardwood Floors; Wall Air Conditioning; Coin-Op Laundry Facilities In The Building; Off-Street Parking For two Cars. This Condo
Photos coming soon!Central AC & HeatPrivate laundry in basementModern Kitchen w/ all new stainless steel appliancesDishwasher & DisposalLarge open living room & dining room w/ wall mounted 70' smart TVSun room/ office nookPets are negotiableOff Street parking is negotiableBoston Pads is not responsible for any errors, omissions and change in price,
An oceanfront oasis just minutes from Boston. This fully renovated 800 sq. ft. private furnished walk-out apartment on the ground level of a 2 family owner occupied home in Winthrop, MA offers a rare combination of comfort, convenience, outdoor living, and true coastal lifestyle.The apartment is fully furnished and move-in ready with a full kitchen, seating for 4, full-size refrigerator,
Welcome to this recently renovated 1300 sqft second floor apartment in Winthrop's desirable Highland district. This spacious 2 bed/1 bath apartment features hardwood flooring throughout, a beautifully updated interior, and brand new kitchen equipped with all new appliances. Enjoy a front porch, off-street parking, basement storage, and on-site laundry for added convenience. Perfectly situated
This quiet condominium is in the Governor's Park complex in the north section of Winthrop. It features a large primary bedroom with a huge walk-in closet, a generous 2nd bedroom, a completely renovated full bathroom, and a kitchen with lots of cabinet space and all the amenities. New flooring and paint throughout. Card-operated laundry is available on the ground floor.The complex
SPACIOUS 1 BEDROOM , on the first floor of a two family owned home. Electric included , oversized eat in kitchen, updated cabinetry, with large pantry, large living room with French doors that enter into a spacious bedroom with a huge closet. Washer and dryer, just for the tenant, in the basement with extra storage. Winthrop By The Sea is an easy commute to downtown Boston, Bus line 2 min walk,
Charming and spacious 3-bedroom,1-bathroom apartment located in the Winthrop by the Sea. This top-floor apartment is part of a multi-family home that underwent a complete renovation in 2019. The renovation included updates such as hardwood floors, stainless steel appliances, bathroom fixtures, and more making it move-in ready. The apartment offers a generous living space of 1,500 sqft, featuring
Welcome to comfortable coastal living at Governors Park — a desirable condominium community in Winthrop, located just across from Boston Harbor with convenient access to the city and local amenities. This rental feature: 2 Spacious bedrooms condo, ample living room, recently renovated modern kitchen with stainless steel appliances, fresh hardwood flooring throughout. Private balcony perfect for
$2550! Available SEPTEMBER 1! Spacious and sunny 1.5 bedroom 1bath apartment in beautiful Winthrop by the sea! Upon entry find an open living room or living and dining room with gorgeous character with wood beam and stone fireplace (non working). Eat in kitchen with dishwasher and gas cooking, ample storage space with large pantry closet. Large king sized master bedroom with ample closet space.
This great 2 bedroom and 1 bath condo is located in Governors Park. There is a new stove, newer kitchen. This comes with 2 car on-premises sticker parking. The bus stop is at the entrance to Governors Park to Orient Heights station. This condo complex is walking distance to Fort Banks school. Winthrop offers fine restaurants, and a center of town for your shopping needs.
Spacious 2-bedroom, 1-bath apartment with a versatile bonus room that can be used as a home office, den, or potential third bedroom. This well-maintained home features a bright and functional layout, hardwood floors, abundant natural light, and generous living space. Ideally located on a quiet residential street just minutes from Winthrop's beaches, restaurants, parks, shopping, public
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