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Downtown Winthrop Homes for Rent

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  • /20

    $2,700 per month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    370 Main St Unit 2, Winthrop, MA 02152

    This nice Furnished 2 Bed 1 Bath place in the WINTHROP area is available for 08-01-2025. Included Features are: Yard, Deck, Common, Balcony.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the

    370 Main St Unit 2, Winthrop, MA 02152
  • /20

    $5,000 per month

    • 4 Beds
    • 1.5 Baths
    • 1,565 Sq Ft
    • Apartment for Rent

    86 Chester Ave Unit 2, Winthrop, MA 02152

    Perfectly located on a corner lot in this picturesque and desirable coastal community, this spacious two level home is spectacular! With tons of windows, incredible light, a wonderful and spacious layout, you'll love it the moment you walk in the door. The kitchen has been tastefully renovated with stylish backsplash, stainless steel appliances, pantry and plenty of cabinet space. The floor plan

    Karin O Connor Compass

    86 Chester Ave Unit 2, Winthrop, MA 02152
  • /20

    $3,000 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    115 Washington Ave Unit 2, Winthrop, MA 02152

    This nice 1 Bed 1 Bath place in the WINTHROP area is available for 11-01-2025. Included Features are: Extra Storage, Yard, Deck, and Laundry in Unit.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about

    115 Washington Ave Unit 2, Winthrop, MA 02152
  • /29

    $3,000 per month

    • 1 Bed
    • 1 Bath
    • 836 Sq Ft
    • Apartment for Rent

    80 Shirley St Unit 1, Winthrop, MA 02152

    Gorgeous farmhouse revival! 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

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 1, Winthrop, MA 02152
  • /16

    $2,900 per month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    70 Cottage Park Rd Unit 1, Winthrop, MA 02152

    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,

    70 Cottage Park Rd Unit 1, Winthrop, MA 02152
  • /39

    $4,000 per month

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft
    • Apartment for Rent

    80 Shirley St Unit 2, Winthrop, MA 02152

    Gorgeous farmhouse revival!! 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

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 2, Winthrop, MA 02152
  • /5

    $2,600 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    76 Fremont St Unit 2, Winthrop, MA 02152

    NO BROKER FEE Large 2 bedroom, 1 bathroom apartment available for rent on Fremont Street in Winthrop. This apartment features a recently renovated kitchen with new cabinets, stainless steel appliances, granite counters, hard wood floors. Large master bedroom - lots of windows. Off street parking available for rent in the driveway.

    76 Fremont St Unit 2, Winthrop, MA 02152
  • /12

    $3,550 per month

    • 3 Beds
    • 2 Baths
    • 1,048 Sq Ft
    • Condo for Rent

    76 Atlantic St Unit 1, Winthrop, MA 02152

    Gorgeously renovated first floor with three spacious bedrooms, two modern baths, new stainless appliances, quartz counters, central A/C, forced hot air, and basement laundry hook-ups plus private locked storage. Tons of natural light and hardwoods throughout with dedicated living and dining rooms, and plenty of closets. Kitchen features SS gas range, refrigerator, microwave, dishwasher and more.

    Tammy Merk Lantern Residential

    76 Atlantic St Unit 1, Winthrop, MA 02152
  • /8

    $3,300 per month

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Condo for Rent

    31 Lincoln St Unit 1, Winthrop, MA 02152

    2 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    31 Lincoln St Unit 1, Winthrop, MA 02152
  • /3

    $2,600 per month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    55 Lincoln St Unit 1, Winthrop, MA 02152

    A truly charming and updated 2-bedroom apartment in the heart of Winthrop by the Sea—a hidden coastal gem just minutes from Boston. This beautiful unit captures the best of New England charm with gleaming hardwood floors throughout, an open and airy layout, and an abundance of natural light from oversized windows in every room. The spacious floor plan includes a separate living room and dining

    Darlene minincleri MP Realty Group

    55 Lincoln St Unit 1, Winthrop, MA 02152
  • /11

    $2,550 per month

    • 1 Bed
    • 1 Bath
    • 9,999 Sq Ft
    • Condo for Rent

    58 Lewis Ave Unit 302, Winthrop, MA 02152

    1 bed and 1 bath located in East Boston. Easy access to downtown and public transportation!

    58 Lewis Ave Unit 302, Winthrop, MA 02152
  • /8

    $3,300 per month

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Apartment for Rent

    35 Lincoln St Unit 1, Winthrop, MA 02152

    Fully renovated unit with all the amenities, and terrific outdoor spaces. Unit 1 of this 3 unit building has 2 bedrooms and 1 bath, and a mix modern conveniences with classic details. Single floor of living, all on the first floor. Open-concept living/kitchen, generous bedrooms with glass enclosed walk in shower and organized closets, enhanced by high ceilings, and large windows throughout. Great

    Daniel Vannoni Housequarters

    35 Lincoln St Unit 1, Winthrop, MA 02152
  • /11

    $2,400 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    26 Central St, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    26 Central St, Winthrop, MA 02152
  • /19

    $2,700 per month

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    15 Hutchinson St Unit 2, Winthrop, MA 02152

    Bright and spacious 2-bedroom, 1-bath apartment in a well-kept 3-family home, offering both comfort and convenience. One dedicated off-street parking space is included—no need to worry about circling the block or snow emergencies. Inside, enjoy an oversized eat-in kitchen featuring a gas stove, a huge pantry, and a washer and dryer included with the rent—a rare and valuable amenity. The apartment

    John Young Ledge & Young Real Estate

    15 Hutchinson St Unit 2, Winthrop, MA 02152
  • /21

    $3,200 per month

    • 2 Beds
    • 2 Baths
    • 969 Sq Ft
    • Condo for Rent

    35 Somerset Ave Unit 5A, Winthrop, MA 02152

    2 bed and 2 bath located in Winthrop. Easy access to downtown and public transportation!

    35 Somerset Ave Unit 5A, Winthrop, MA 02152
  • /11

    $2,400 per month

    • 1 Bed
    • 1 Bath
    • 820 Sq Ft
    • Apartment for Rent

    554 Pleasant St Unit 2, Winthrop, MA 02152

    Direct Oceanfront Living! Enjoy front-row views of passing boats from this beautifully updated and well-maintained 1-bedroom, 1-bath apartment. The open-concept layout features hardwood floors, high ceilings, abundant natural light, and large windows showcasing stunning ocean views. Additional highlights include private in-unit laundry and one off-street parking space. Located in Winthrop, a

    Candice Hodgson Lyv Realty

    554 Pleasant St Unit 2, Winthrop, MA 02152
  • /11

    $2,500 per month

    • 1 Bed
    • 1 Bath
    • 820 Sq Ft
    • Condo for Rent

    554 Pleasant St Unit 2, Winthrop, MA 02152

    1 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

    554 Pleasant St Unit 2, Winthrop, MA 02152
  • /26

    $2,900 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    370 Main St Unit 2, Winthrop, MA 02152

    Welcome to 370 Main St #2 in beautiful Winthrop, MA—a fully furnished 2-bedroom, 1-bath apartment that’s ready for immediate move-in. Just bring your bags and start living comfortably in this well-kept second-floor unit. With everything you need already in place, it’s perfect for anyone looking for a convenient, no-fuss rental. The apartment features large windows throughout, allowing for great

    Antonio Ferreira Zander Realty Group

    370 Main St Unit 2, Winthrop, MA 02152
  • /37

    $2,500 per month

    • 1-2 Beds
    • 2 Baths
    • 524 Sq Ft
    • Condo for Rent

    5 Fremont St, Winthrop, MA 02152

    5 Fremont St, Winthrop, MA 02152
  • /16

    $3,600 per month

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Apartment for Rent

    49 Bates Ave Unit 51, Winthrop, MA 02152

    Price drop down without furnished.Luxury apartment for rent in Winthrop, MA. This spacious unit features three bedrooms and two full bathrooms, and boasts hardwood floors throughout the entire home. The apartment is equipped with gas heating, ensuring warmth and comfort during the colder months.The entire third floor is dedicated to the main bedroom, providing privacy and ample space, and adorned

    David Li eXp Realty

    49 Bates Ave Unit 51, Winthrop, MA 02152
  • /37

    $3,200 per month

    • 1-2 Beds
    • 2 Baths
    • 524 Sq Ft
    • Condo for Rent

    5 Fremont St, Winthrop, MA 02152

    5 Fremont St, Winthrop, MA 02152
  • /42

    $3,150 per month

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Apartment for Rent

    100 Summit Ave Unit 2, Winthrop, MA 02152

    Brittney Lamme D & R Realty

    100 Summit Ave Unit 2, Winthrop, MA 02152

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.
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