19

Downtown Winthrop Homes for Sale

Section Image
  • 37-39 Hutchinson St, Winthrop, MA 02152
    37-39 Hutchinson St, Winthrop, MA 02152
    37-39 Hutchinson St, Winthrop, MA 02152
    /41

    $899,000

    • 5 Beds
    • 2 Baths
    • 2,958 Sq Ft

    37-39 Hutchinson St, Winthrop, MA 02152

    Endless Potential in Prime Seaside Location – 02152 Welcome to this oversized two-family home located in the highly desirable seaside community of Winthrop, 02152. Perfectly situated on a generous lot, this property offers a rare opportunity for investors, multi-generational living, or owner-occupants looking to customize and create value.Each unit features spacious layouts with room to grow, and

    Nicole Bettano Lantern Residential

    37-39 Hutchinson St, Winthrop, MA 02152
  • 136 Pauline St, Winthrop, MA 02152
    136 Pauline St, Winthrop, MA 02152
    136 Pauline St, Winthrop, MA 02152
    /42

    $899,000

    • 4 Beds
    • 3.5 Baths
    • 2,350 Sq Ft

    136 Pauline St, Winthrop, MA 02152

    Beautifully renovated 4-bedroom, 3.5-bath single-family home, fully gutted and updated in 2020. This turnkey property features an open floor plan with seamless flow between the spacious living room, dining area, and modern kitchen—perfect for today’s lifestyle and entertaining. The primary suite includes a walk-in closet and private en-suite bath. A finished basement (2021) provides flexible

    Anthony Carestia William Raveis R.E. & Home Services

    136 Pauline St, Winthrop, MA 02152
  • 10 Somerset Ave Unit 206, Winthrop, MA 02152
    10 Somerset Ave Unit 206, Winthrop, MA 02152
    10 Somerset Ave Unit 206, Winthrop, MA 02152
    /32

    $594,900

    • 2 Beds
    • 2 Baths
    • 985 Sq Ft

    10 Somerset Ave Unit 206, Winthrop, MA 02152

    Welcome to The Somerset—Winthrop’s newest boutique condo development, where coastal charm meets modern luxury. This spacious 2-bedroom, 2-bath home is designed for effortless living, featuring a sun-drenched open layout, private balcony, and oversized walk-in wardrobes in both bedrooms. Enjoy a sleek kitchen with stainless steel appliances, quartz countertops, and soft-close cabinetry, flowing

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 206, Winthrop, MA 02152
  • 10 Somerset Ave Unit 408, Winthrop, MA 02152
    10 Somerset Ave Unit 408, Winthrop, MA 02152
    10 Somerset Ave Unit 408, Winthrop, MA 02152
    /27

    $539,900

    • 1 Bed
    • 1 Bath
    • 767 Sq Ft

    10 Somerset Ave Unit 408, Winthrop, MA 02152

    Step into a spacious 1-bedroom + den home at The Somerset, Winthrop’s newest boutique condo community blending coastal charm with modern comfort. This thoughtfully designed layout offers an open-concept living space, a versatile den ideal for a home office or guest room, and a walk-in closet in the bedroom.Enjoy upscale finishes throughout—quartz countertops, stainless steel appliances, central

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 408, Winthrop, MA 02152
  • 17 Edgehill Rd, Winthrop, MA 02152
    17 Edgehill Rd, Winthrop, MA 02152
    17 Edgehill Rd, Winthrop, MA 02152
    /42

    $799,900

    • 5 Beds
    • 3 Baths
    • 2,114 Sq Ft

    17 Edgehill Rd, Winthrop, MA 02152

    Welcome home to 17 Edgehill Road! Nestled in a desirable waterfront community, this spacious single-family is located steps from the harbor & home to some of the most incredible sunset views at Donovan's Beach! Along with being a shoreline neighborhood, Edgehill is known for its charming surroundings next to the lovely Ingleside Park. Here you'll find the kind of space & living that encompasses

    Atiyeh Cassidy Blue Sky Realty

    17 Edgehill Rd, Winthrop, MA 02152
  • 123 Buchanan St, Winthrop, MA 02152
    123 Buchanan St, Winthrop, MA 02152
    123 Buchanan St, Winthrop, MA 02152
    /30

    $588,888

    • 4 Beds
    • 1.5 Baths
    • 1,785 Sq Ft

    123 Buchanan St, Winthrop, MA 02152

    Step back in time, a stately 19th-century home ready to be restored and reimagined. This 4-bedroom, 1.5-bath is rich with character—featuring original beamed ceilings, ornamental exterior wood trim, and timeless architectural details that set the stage for a stunning transformation. Located near Winthrop Golf Club, High School, and the coastal beauty of Boston’s shoreline, this home offers a rare

    Ronda Cogliano Century 21 North East

    123 Buchanan St, Winthrop, MA 02152
  • 26 Enfield Rd, Winthrop, MA 02152
    26 Enfield Rd, Winthrop, MA 02152
    26 Enfield Rd, Winthrop, MA 02152
    /41

    $849,900

    • 5 Beds
    • 2 Baths
    • 2,494 Sq Ft

    26 Enfield Rd, Winthrop, MA 02152

    Charming two-family in desirable area of Winthrop. Steps away from Ingleside Park's playground, roller hockey court and baseball field. The restaurants of Winthrop's center are close proximity as well. Great opportunity on one of the nicest streets in Winthrop.

    Nicholas Martino Noddle Island Real Estate

    26 Enfield Rd, Winthrop, MA 02152
  • 56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    /19

    $799,900

    • 4 Beds
    • 2 Baths
    • 2,103 Sq Ft

    56 Main St, Winthrop, MA 02152

    OPPORTUNITY KNOCKS.......Two family with large yard located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! The home was gutted in 2001. The owner's unit is on the second and third floors with an open floor plan and loads of natural lighting. It contains a living room, dining area, kitchen, bath and bedroom on the second floor and a

    Sharon Tallent Compass

    56 Main St, Winthrop, MA 02152
  • 10 Somerset Ave Unit 201, Winthrop, MA 02152
    10 Somerset Ave Unit 201, Winthrop, MA 02152
    10 Somerset Ave Unit 201, Winthrop, MA 02152
    /29

    $663,609

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    10 Somerset Ave Unit 201, Winthrop, MA 02152

    The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 201, Winthrop, MA 02152
  • 19 Banks St, Winthrop, MA 02152
    19 Banks St, Winthrop, MA 02152
    19 Banks St, Winthrop, MA 02152
    /29

    $735,000

    • 3 Beds
    • 1 Bath
    • 1,269 Sq Ft

    19 Banks St, Winthrop, MA 02152

    Price improvement! Do you ever step into a home and feel an instant calm—as if it’s been waiting just for you? 19 Banks Street wraps you in warmth from the moment you enter. The sunporch glows with light from three walls of windows and leads to a living room with gleaming hardwood floors and a fireplace. This classic 3-bed, 1-bath Colonial is filled with charm—paned windows, graceful flow—and

    Susan Doig Charlesgate Realty Group, llc

    19 Banks St, Winthrop, MA 02152
  • 60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, Winthrop, MA 02152
    /30

    $729,000

    • 3 Beds
    • 1 Bath
    • 1,548 Sq Ft

    60 Waldemar Ave, Winthrop, MA 02152

    Located in one of Winthrop's most desirable Center locations, this well maintained 7 room, 3 bedroom single says welcome home! The kitchen has been updated with granite counters and stainless steel appliances and the bayed living and dining rooms with high ceilings are elegant and very inviting. The full bath has a jetted tub and separate shower! There are beautiful wood floors throughout. Love

    James Polino Compass

    60 Waldemar Ave, Winthrop, MA 02152
  • 143 Morton St, Winthrop, MA 02152
    143 Morton St, Winthrop, MA 02152
    143 Morton St, Winthrop, MA 02152
    /24

    $799,900

    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    143 Morton St, Winthrop, MA 02152

    Welcome to this spacious single-family home in Winthrop! Step into a large living room that flows into a formal dining room and an updated kitchen (2016). A full bath on the first floor adds convenience, and a cozy family room off the kitchen offers great bonus space. Step out to the deck and enjoy a generous, fenced-in yard—perfect for outdoor entertaining or relaxing. Upstairs, you'll find four

    The Reference Group Reference Real Estate

    143 Morton St, Winthrop, MA 02152
  • 10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    /29

    $551,633

    • 1 Bed
    • 1 Bath
    • 683 Sq Ft

    10 Somerset Ave Unit 405, Winthrop, MA 02152

    The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 405, Winthrop, MA 02152
  • 35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    /27

    $560,000

    • 2 Beds
    • 2 Baths
    • 823 Sq Ft

    35 Somerset Ave Unit 6, Winthrop, MA 02152

    Welcome to 35 Somerset Ave, Unit #6 (Pent House), nestled in the heart of Winthrop! This stunning newly renovated 2-bedroom, 2 full bathroom condo, offers a perfect fusion of modern comfort and seaside charm. Located just moments from the beach, this inviting unit offers breathtaking views from its massive private roof deck and seamless access to downtown and the beach. Every aspect of this unit

    John Maggio EVO Real Estate Group, LLC

    35 Somerset Ave Unit 6, Winthrop, MA 02152
  • 35 Somerset Ave Unit 5, Winthrop, MA 02152
    35 Somerset Ave Unit 5, Winthrop, MA 02152
    35 Somerset Ave Unit 5, Winthrop, MA 02152
    /21

    $599,000

    • 2 Beds
    • 2 Baths
    • 969 Sq Ft

    35 Somerset Ave Unit 5, Winthrop, MA 02152

    Welcome to 35 Somerset #5 in Winthrop! This stylish 2-bed 2-bath condo offers 969 square feet of well-designed living space. With two private outdoor areas, including a rare rooftop deck, this home is absolutely perfect for enjoying the warmer months ahead. This home offers an open layout, hardwood floors, and high end finishes including updated lighting, modern bathroom fixtures, and a

    Danielle DeGrazia Choose Boston, LLC

    35 Somerset Ave Unit 5, Winthrop, MA 02152
  • 136 Locust Way, Winthrop, MA 02152
    136 Locust Way, Winthrop, MA 02152
    136 Locust Way, Winthrop, MA 02152
    /14

    $654,900

    • 3 Beds
    • 1 Bath
    • 1,878 Sq Ft

    136 Locust Way, Winthrop, MA 02152

    Well maintained 3 bedroom Colonial just moments from the beach. Large open rooms with lots of natural light. Lots of cabinet space in the super functional kitchen. 1st floor laundry hookups for convenience. 3 full sized bedrooms. Great yard. Nice wrap around porch to enjoy the summer nights. Seller willing to buy down the mortgage rate on this home. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

    Tyler Scaglione Cameron Real Estate Group

    136 Locust Way, Winthrop, MA 02152
  • 80 Shirley St, Winthrop, MA 02152
    80 Shirley St, Winthrop, MA 02152
    80 Shirley St, Winthrop, MA 02152
    /29

    $1,100,000

    • 4 Beds
    • 2 Baths
    • 2,366 Sq Ft

    80 Shirley St, Winthrop, MA 02152

    Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchens and natural light

    Nick Burnes Red Tree Real Estate

    80 Shirley St, Winthrop, MA 02152
  • 80 Shirley St Unit 2, Winthrop, MA 02152
    80 Shirley St Unit 2, Winthrop, MA 02152
    80 Shirley St Unit 2, Winthrop, MA 02152
    /39

    $649,900

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft

    80 Shirley St Unit 2, Winthrop, MA 02152

    Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchen and natural light

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 2, Winthrop, MA 02152
  • 80 Shirley St Unit 1, Winthrop, MA 02152
    80 Shirley St Unit 1, Winthrop, MA 02152
    80 Shirley St Unit 1, Winthrop, MA 02152
    /29

    $449,900

    • 1 Bed
    • 1 Bath
    • 836 Sq Ft

    80 Shirley St Unit 1, Winthrop, MA 02152

    Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchen and natural light

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 1, Winthrop, MA 02152
Massachusetts Winthrop Downtown Winthrop

Real Estate & Homes for Sale in Downtown Winthrop, Winthrop

Why Live in Downtown Winthrop
Downtown Winthrop features a mix of peaceful beach cottages, Cape Cods, and colonial-inspired homes, with properties ranging from the early 1800s to the mid-20th century. Single-family houses, multi-family properties, condos, and commercial storefronts line the established streets, with lot sizes typically between 3,000 and 7,000 square feet. The neighborhood's coastal charm is enhanced by its proximity to beaches, marinas, and yacht clubs like Winthrop Yacht Club and Pleasant Park Yacht Club, which offer sailing programs and social activities. Residents enjoy walking along Donovan’s Beach and Winthrop Beach, with views of planes from nearby Logan International Airport, just 4 miles away. Community events such as the Independence Day Horrible’s Parade and the annual Strawberry Festival foster a strong sense of local culture. Ingleside Park hosts a farmers market, skate park, tennis courts, and a baseball field, while Winthrop Golf Club offers a public nine-hole course. Dining options include Belle Isle Seafood, the historic Winthrop Arms Hotel and Restaurant, Vuolo's Italian eatery, and Nick’s Place pizzeria. For groceries, Winthrop Market Place is centrally located, with additional shopping available 2 miles north at The Shops at Suffolk Downs. The neighborhood is served by Winthrop Public Schools, with the highly rated William P. Gorman Fort Banks Elementary School for young learners. Commuters benefit from easy access to downtown Boston, 6 miles away, via Massachusetts Route 1A, MBTA T subway lines at Orient Heights, and ferry service at Winthrop Landing. The area has a low crime risk compared to the national average, contributing to its appeal for residents.
Learn more about living in Downtown Winthrop

Frequently Asked Questions

Is Downtown Winthrop a good place to live?
Downtown Winthrop is a good place to live. Downtown Winthrop is considered fairly walkable and somewhat bikeable. Downtown Winthrop has 1 park for recreational activities. It has a median age of 45. The average household income is $118,624 which is above the national average. College graduates make up 38.6% of residents. A majority of residents in Downtown Winthrop are home owners, with 48.2% of residents renting and 51.8% of residents owning their home. A local real estate agent serving Downtown Winthrop can help you decide if this neighborhood is the right one for you. Learn more on our Downtown Winthrop neighborhood guide.
How much do you need to make to afford a house in Downtown Winthrop?
The median home price in Downtown Winthrop is $607,450. If you put a 20% down payment of $121,500 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $3,140 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $135K a year to afford the median home price in Downtown Winthrop. The average household income in Downtown Winthrop is $119K.
What are the best public schools in Downtown Winthrop?
The best public schools that serve Downtown Winthrop are:
What are the best private schools in Downtown Winthrop?
The best private schools that serve Downtown Winthrop are:
What are the most popular zip codes in Downtown Winthrop, Winthrop, MA?
The most popular zip codes in Downtown Winthrop, Winthrop, MA include 02152, 02128, 02151, 02150 and 02129.
What are the most popular neighborhoods near Downtown Winthrop, Winthrop, MA?
The most popular neighborhoods near Downtown Winthrop, Winthrop, MA are Winthrop Beach, Winthrop Highlands, Cottage Park, Court Park and Cottage Hill.

Home Trends in Downtown Winthrop, MA

On average, homes in Downtown Winthrop, Winthrop sell after 25 days on the market compared to the national average of 50 days. The median sale price for homes in Downtown Winthrop, Winthrop over the last 12 months is $625,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$625,000
Median Single Family Sale Price
$689,000
Median Townhouse Sale Price
$771,225
Median 2 Bedroom Sale Price
$383,000
Median 1 Bedroom Sale Price
$542,450
Average Price Per Sq Ft
$459
Number of Homes for Sale
15
Last 12 months Home Sales
53
Months of Supply
3.40
Median List Price
$607,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
13%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group