3,427

Downtown Winthrop Homes

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  • 10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    /32

    $551,633

    • 1 Bed
    • 1 Bath
    • 683 Sq Ft

    10 Somerset Ave Unit 405, Winthrop, MA 02152

    Welcome to Unit 405 at The Somerset, a premier boutique condominium community in the heart of Winthrop. This well-designed 1-bedroom residence offers a spacious bedroom with a generous closet and an open-concept kitchen and living area that’s perfect for both entertaining and unwinding. The home features quartz countertops, stainless steel appliances, central A/C, and modern, stylish finishes

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 405, Winthrop, MA 02152
  • 40 Cottage Park Rd Unit 2, Winthrop, MA 02152
    40 Cottage Park Rd Unit 2, Winthrop, MA 02152
    40 Cottage Park Rd Unit 2, Winthrop, MA 02152
    /10

    $3,500 total monthly price

    • 3 Beds
    • 1 Bath
    • 2,000 Sq Ft
    • Apartment for Rent

    40 Cottage Park Rd Unit 2, Winthrop, MA 02152

    Beautiful 3 Bedroom, 1 Bathroom Apartment in Winthrop, MA – Available December 1st!Welcome to this spacious one-level apartment offering comfort, convenience, and plenty of room to spread out. Featuring 3 bedrooms and 1 full bathrooms, this home provides an ideal layout for families, roommates, or anyone seeking extra space. The unit offers a bright living area, a functional kitchen, ample

    Agent Photo

    Juan Lopera-Martinez

    eXp Realty

    (617) 752-6511

    40 Cottage Park Rd Unit 2, Winthrop, MA 02152
  • 339 Winthrop St, Winthrop, MA 02152
    339 Winthrop St, Winthrop, MA 02152
    339 Winthrop St, Winthrop, MA 02152
    /42

    $910,000 Sold Dec 05, 2025

    • 3,776 Sq Ft
    • $241/SF
    • 19 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1910

    339 Winthrop St, Winthrop, MA 02152

    This beautifully maintained two-family home offers the perfect blend of meticulous care, charm and city convenience. Just minutes from downtown Boston and Logan Airport, enjoy easy commuting paired with the tranquility of a vibrant beachside community. Nearly 4,000 sq. ft. of living space features hardwood floors, a custom kitchen with island, gas fireplace, and a flexible floor plan with home

    Danielle McCarthy Berkshire Hathaway HomeServices Commonwealth Real Estate

    339 Winthrop St, Winthrop, MA 02152
    • 88 Winthrop St, Winthrop, MA 02152
      88 Winthrop St, Winthrop, MA 02152
      88 Winthrop St, Winthrop, MA 02152
      /28

      Est $669,094 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,668 Sq Ft

      88 Winthrop St, Winthrop, MA 02152

      88 Winthrop 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
    /21

    $629,000

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

    10 Somerset Ave Unit 201, Winthrop, MA 02152

    Welcome to Unit 201 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 201, Winthrop, MA 02152
  • 40 Cottage Park Rd Unit 3, Winthrop, MA 02152
    40 Cottage Park Rd Unit 3, Winthrop, MA 02152
    40 Cottage Park Rd Unit 3, Winthrop, MA 02152
    /4

    $1,500 total monthly price

    • 1 Bed
    • 1 Bath
    • 2,000 Sq Ft
    • Apartment for Rent

    40 Cottage Park Rd Unit 3, Winthrop, MA 02152

    Beautiful 1 Bedroom, 1 Bathroom Apartment in Winthrop, MA – Available December 1st!Welcome to this spacious bedroom offering comfort, convenience, and plenty of room to spread out.Located in the heart of Winthrop, you’ll be close to local shops, public transportation, parks, restaurants, and beautiful beaches. Move-in ready December 1st.Don’t miss this opportunity to live in one of Winthrop’s

    Agent Photo

    Juan Lopera-Martinez

    eXp Realty

    (617) 676-0450

    40 Cottage Park Rd Unit 3, Winthrop, MA 02152
  • 95 Summit Ave Unit 1, Winthrop, MA 02152
    95 Summit Ave Unit 1, Winthrop, MA 02152
    95 Summit Ave Unit 1, Winthrop, MA 02152
    /40

    $560,000 Sold Nov 25, 2025

    • 1,314 Sq Ft
    • $426/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1890

    95 Summit Ave Unit 1, Winthrop, MA 02152

    Just steps from Winthrop Beach, this stunning condominium blends seaside tranquility with modern comfort. Gut renovated and completed in 2021, windows at every turn fill the home with natural light and salt-air breezes. Sun-filled open spaces feature hardwood floors and a coastal-modern design. The chef’s kitchen is appointed with sleek white cabinetry, stainless steel appliances, and a spacious

    Ann DiMascio Lamacchia Realty, Inc.

    95 Summit Ave Unit 1, Winthrop, MA 02152
    • 46 Jefferson St Unit 1, Winthrop, MA 02152
      46 Jefferson St Unit 1, Winthrop, MA 02152
      46 Jefferson St Unit 1, Winthrop, MA 02152
      /37

      Est $589,647 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft

      46 Jefferson St Unit 1, Winthrop, MA 02152

      46 Jefferson St Unit 1, 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
    /31

    $509,900

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    35 Somerset Ave Unit 6, Winthrop, MA 02152

    UPSCALE 2 BEDROOM, 2 BATH TOP FLOOR UNIT WITH ROOFTOP EXCLUSIVE OUTDOOR DECK......A two year old renovation and a must see! Bright sun-filled condo with a spacious kitchen/living room combo with plenty of cabinets and huge center island with pretty pendant lighting......perfect for entertaining and personal enjoyment. Two large bedrooms, one a main suite with it's own full bath and the other bath

    Sharon Tallent Compass

    35 Somerset Ave Unit 6, Winthrop, MA 02152
  • 6 Edgehill Rd Unit 1, Winthrop, MA 02152
    6 Edgehill Rd Unit 1, Winthrop, MA 02152
    6 Edgehill Rd Unit 1, Winthrop, MA 02152
    /14

    $4,250 per month plus fees

    • 4 Beds
    • 2 Baths
    • Condo for Rent

    6 Edgehill Rd Unit 1, Winthrop, MA 02152

    This nice 4 Bedrooms 2 Bath place in the WINTHROP area is available for Now. Included Features are: Balcony, 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 the properties reflect

    6 Edgehill Rd Unit 1, Winthrop, MA 02152
  • 40 Cottage Park Rd, Winthrop, MA 02152
    40 Cottage Park Rd, Winthrop, MA 02152
    40 Cottage Park Rd, Winthrop, MA 02152
    /30

    $950,000 Sold Nov 21, 2025

    • 2,550 Sq Ft
    • $373/SF
    • 8 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1900

    40 Cottage Park Rd, Winthrop, MA 02152

    Nestled in the sought-after Cottage Park neighborhood, this beautifully maintained two-family home offers over 2,400 sq ft of living space, a garage plus 3 off-street parking spaces, and is being delivered vacant—perfect for owner-occupants or investors. Unit 1 features 2 bedrooms, a sunroom, and classic wood floors. Unit 2 spans two levels with 3 bedrooms, 2 full baths, central air, and a family

    The Reference Group Reference Real Estate

    40 Cottage Park Rd, Winthrop, MA 02152
    • 100 Sagamore Ave, Winthrop, MA 02152
      100 Sagamore Ave, Winthrop, MA 02152
      100 Sagamore Ave, Winthrop, MA 02152
      /29

      Est $920,429 Not Listed For Sale

      • 5 Beds
      • 1.5 Baths
      • 2,608 Sq Ft

      100 Sagamore Ave, Winthrop, MA 02152

      100 Sagamore Ave, Winthrop, MA 02152
  • 174 Winthrop St Unit 2, Winthrop, MA 02152
    174 Winthrop St Unit 2, Winthrop, MA 02152
    174 Winthrop St Unit 2, Winthrop, MA 02152
    /26

    $729,900

    • 3 Beds
    • 2.5 Baths
    • 1,973 Sq Ft

    174 Winthrop St Unit 2, Winthrop, MA 02152

    Step inside this beautifully reimagined residence where timeless charm meets modern comfort. This 3 bedroom, 2.5 bath home has been fully renovated with thoughtful design choices that highlight the building’s historic character while adding the conveniences of today. Original hardwood floors anchor the sun-filled interior, where a welcoming living area flows into a stylish kitchen, complemented

    Leighann Eruzione Lantern Residential

    174 Winthrop St Unit 2, Winthrop, MA 02152
  • 5 Fremont St Unit 301, Winthrop, MA 02152
    5 Fremont St Unit 301, Winthrop, MA 02152
    5 Fremont St Unit 301, Winthrop, MA 02152
    /18

    $3,200 total monthly price

    • 2 Beds
    • 2 Baths
    • 9,999 Sq Ft
    • Apartment for Rent

    5 Fremont St Unit 301, Winthrop, MA 02152

    Welcome home to this beautifully updated 2-bedroom 2-bathroom apartment with bonus room as an office located in an elevator building featuring a spacious living area and a modern kitchen outfitted with sleek stainless steel appliances. Two queen sized bedroom with generous closet space. Third smaller room great for office space. Stay comfortable all year with high-efficiency mini-split heating

    Mario Fiume Anzalone Realty

    5 Fremont St Unit 301, Winthrop, MA 02152
  • 15 Ocean Dr Unit 105, Winthrop, MA 02152
    15 Ocean Dr Unit 105, Winthrop, MA 02152
    15 Ocean Dr Unit 105, Winthrop, MA 02152
    /31

    $465,000 Sold Nov 21, 2025

    • 1,460 Sq Ft
    • $318/SF
    • 25 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1920

    15 Ocean Dr Unit 105, Winthrop, MA 02152

    15 Ocean Dr #105 delivers flexible two-level living with dramatic ceiling height and oversized windows just minutes to the beach. Newly renovated with 2 luxurious full baths, in-unit laundry, central A/C, one deeded parking, and access to a common roof deck. Smart layout features a main kitchen on the upper level and a lower-level kitchenette with a separate entrance-ideal for guests,

    Sarah Strangie Keller Williams Realty Boston-Metro | Back Bay

    15 Ocean Dr Unit 105, Winthrop, MA 02152
    • 110 Summit Ave Unit 3, Winthrop, MA 02152
      110 Summit Ave Unit 3, Winthrop, MA 02152
      110 Summit Ave Unit 3, Winthrop, MA 02152
      /31

      Est $618,508 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,350 Sq Ft

      110 Summit Ave Unit 3, Winthrop, MA 02152

      110 Summit Ave Unit 3, Winthrop, MA 02152
  • 3 Buckthorn Terrace Unit 2, Winthrop, MA 02152
    3 Buckthorn Terrace Unit 2, Winthrop, MA 02152
    3 Buckthorn Terrace Unit 2, Winthrop, MA 02152
    /41

    $750,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,870 Sq Ft

    3 Buckthorn Terrace Unit 2, Winthrop, MA 02152

    Back to Market due to buyer financing.....Tucked away on a quiet street, this home boasts stately features and has been meticulously renovated. From the elegant newel post to the timeless kitchen details, nothing was overlooked. During the condo conversion, preserving the home's original integrity was a priority. The first floor offers 2 bedrooms, laundry, and a full bath with marble tile floors.

    Elizabeth Ferrara Cottage Hill Real Estate

    3 Buckthorn Terrace Unit 2, Winthrop, MA 02152
  • 62 Locust St Unit 1, Winthrop, MA 02152
    62 Locust St Unit 1, Winthrop, MA 02152
    62 Locust St Unit 1, Winthrop, MA 02152
    /21

    $3,200 total monthly price

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

    62 Locust St Unit 1, Winthrop, MA 02152

    AVAILABLE 1/1/26. Be the first to live in this beautifully built, modern 3-bedroom, 1-bath apartment located in the highly desirable coastal town of Winthrop. This fresh new construction features an open-concept layout, bright natural light, and quality finishes throughout. In between, we have the look of a quaint and friendly New England town with shops, parks, marinas, inns, and miles of lovely

    62 Locust St Unit 1, Winthrop, MA 02152
  • 123 Hermon St, Winthrop, MA 02152
    123 Hermon St, Winthrop, MA 02152
    123 Hermon St, Winthrop, MA 02152
    /39

    $875,000 Sold Nov 18, 2025

    • 2,972 Sq Ft
    • $294/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1900

    123 Hermon St, Winthrop, MA 02152

    Well maintained spacious two family in a prime location. Both apartments are 1,486 sf and have open floor plans, wood flooring and high ceilings. Unit 1 has a great eat in kitchen with washer and dryer area in the hallway. Bedrooms are good size with double closets. There is a seamless flow from the front door to the open living / dining room. This unit offers easy access to the yard and the

    Valerie Lane Brad Hutchinson Real Estate

    123 Hermon St, Winthrop, MA 02152
    • 103 Summit Ave Unit 3, Winthrop, MA 02152
      103 Summit Ave Unit 3, Winthrop, MA 02152
      103 Summit Ave Unit 3, Winthrop, MA 02152
      /21

      Est $454,969 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 806 Sq Ft

      103 Summit Ave Unit 3, Winthrop, MA 02152

      103 Summit Ave Unit 3, 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 Pending

    • 1 Bed
    • 1 Bath
    • 767 Sq Ft

    10 Somerset Ave Unit 408, Winthrop, MA 02152

    Welcome to Unit 408 – 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

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 408, Winthrop, MA 02152
  • 95 Hermon St Unit 1, Winthrop, MA 02152
    95 Hermon St Unit 1, Winthrop, MA 02152
    95 Hermon St Unit 1, Winthrop, MA 02152
    /7

    $3,500 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • Apartment for Rent

    95 Hermon St Unit 1, Winthrop, MA 02152

    Spacious and bright deleaded 3-bedroom apartment located in the heart of Winthrop Center! This large second floor apartment offers the perfect blend of comfort and convenience—just steps from schools, parks, shopping, and restaurants.Enjoy an oversized master bedroom with access to a private balcony, ideal for morning coffee or evening relaxation. The large eat-in kitchen provides plenty of room

    Erica Gore Century 21 Seaport

    95 Hermon St Unit 1, Winthrop, MA 02152
  • 60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, Winthrop, MA 02152
    /30

    $610,000 Sold Nov 14, 2025

    • 1,548 Sq Ft
    • $394/SF
    • 114 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1900

    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
    • 103 Summit Ave Unit 2, Winthrop, MA 02152
      103 Summit Ave Unit 2, Winthrop, MA 02152
      103 Summit Ave Unit 2, Winthrop, MA 02152
      /19

      Est $457,371 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 965 Sq Ft

      103 Summit Ave Unit 2, Winthrop, MA 02152

      103 Summit Ave Unit 2, 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 Pending

    • 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
  • 31 Locust St Unit Seaside Suite, Winthrop, MA 02152
    31 Locust St Unit Seaside Suite, Winthrop, MA 02152
    31 Locust St Unit Seaside Suite, Winthrop, MA 02152
    /14

    $2,500 total monthly price

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

    31 Locust St Unit Seaside Suite, Winthrop, MA 02152

    This property is great because it is cozy, clean, safe and perfect for one to two people.

    31 Locust St Unit Seaside Suite, Winthrop, MA 02152
  • 89-91 Sagamore Ave, Winthrop, MA 02152
    89-91 Sagamore Ave, Winthrop, MA 02152
    89-91 Sagamore Ave, Winthrop, MA 02152
    /35

    $830,000 Sold Nov 14, 2025

    • 2,000 Sq Ft
    • $415/SF
    • 25 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1966

    89-91 Sagamore Ave, Winthrop, MA 02152

    Welcome to this well-maintained 2-family property located in the desirable Lower Highlands neighborhood of Winthrop by the Sea. This home is just a short stroll to the beach, shops and local dining! Perfect for homeowners seeking rental income or investors alike! The main unit features 3 bedrooms, 1 bathroom, and a bright, open, inviting living area. A finished family room and half bath on the

    Christine D'Ambrosio Lantern Residential

    89-91 Sagamore Ave, Winthrop, MA 02152
    • 103 Summit Ave Unit 1, Winthrop, MA 02152
      103 Summit Ave Unit 1, Winthrop, MA 02152
      103 Summit Ave Unit 1, Winthrop, MA 02152
      /30

      Est $362,033 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 894 Sq Ft

      103 Summit Ave Unit 1, Winthrop, MA 02152

      103 Summit Ave Unit 1, Winthrop, MA 02152
  • 10 Somerset Ave Unit 211, Winthrop, MA 02152
    10 Somerset Ave Unit 211, Winthrop, MA 02152
    10 Somerset Ave Unit 211, Winthrop, MA 02152
    /7

    $500,000 Pending

    • 1 Bed
    • 1 Bath
    • 633 Sq Ft

    10 Somerset Ave Unit 211, Winthrop, MA 02152

    Welcome to The Somerset—Winthrop’s newest boutique condo development! This collection of 29 thoughtfully designed homes offers studios, 1-bed, 1+ bed, and 2-bedroom layouts with quality finishes and a coastal vibe. Enjoy open-concept living, stainless steel appliances, quartz countertops, central A/C, and stylish modern touches. Most units include garage parking, and select homes feature private

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 211, Winthrop, MA 02152
  • 220 Winthrop St Unit 301, Winthrop, MA 02152
    220 Winthrop St Unit 301, Winthrop, MA 02152
    220 Winthrop St Unit 301, Winthrop, MA 02152
    /10

    $2,300 total monthly price

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

    220 Winthrop St Unit 301, Winthrop, MA 02152

    Available December 1st! Discover this brand-new, fully renovated one-bedroom, one-bathroom apartment located in Winthrop center. Situated in an elevator building, the apartment features gleaming hardwood floors, an open concept living room filled with natural light, and a sleek kitchen equipped with stainless steel appliances, including a dishwasher, gas stove, refrigerator, and microwave. The

    Mario Fiume Anzalone Realty

    220 Winthrop St Unit 301, Winthrop, MA 02152
  • 59 Crescent St, Winthrop, MA 02152
    59 Crescent St, Winthrop, MA 02152
    59 Crescent St, Winthrop, MA 02152
    /30

    $740,000 Sold Nov 05, 2025

    • 1,716 Sq Ft
    • $431/SF
    • 7 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1895

    59 Crescent St, Winthrop, MA 02152

    Welcome to 59 Crescent St in Winthrop. This well-kept bungalow offers 1,716 square feet of living space with 3 bedrooms and 2.5 bathrooms. The first floor includes a large living room with skylights, bay windows, hardwood floors, and recessed lighting, a dining area, and an updated kitchen with granite counters, stainless steel appliances, and a gas stove. Upstairs, you will find comfortable

    The Reference Group Reference Real Estate

    59 Crescent St, Winthrop, MA 02152
    • 100 Locust St, Winthrop, MA 02152
      100 Locust St, Winthrop, MA 02152
      100 Locust St, Winthrop, MA 02152
      /21

      Est $765,113 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,668 Sq Ft

      100 Locust St, Winthrop, MA 02152

      100 Locust St, Winthrop, MA 02152
  • 56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    /27

    $799,900

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

    56 Main St, Winthrop, MA 02152

    OPPORTUNITY KNOCKS.......Two family with large yard and located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! Some renovations as of 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 one bedroom. The second floor and a

    Sharon Tallent Compass

    56 Main St, Winthrop, MA 02152
  • 233 Pleasant St Unit 2, Winthrop, MA 02152
    233 Pleasant St Unit 2, Winthrop, MA 02152
    233 Pleasant St Unit 2, Winthrop, MA 02152
    /11

    $2,500 total monthly price

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

    233 Pleasant St Unit 2, Winthrop, MA 02152

    apartmentlaundry in unitno smokingPlenty of street parking*One car driveway parking spot available for $100 a month Beautiful 2nd floor 2-bedroom 1 Bathroom with hot tub. Freshly painted and new gas heating system with instant hot water. Washer and dryer in Apartment. Extra back room for an office. Prime location with bus stop right outside your door. 1 mile from Orient

    233 Pleasant St Unit 2, Winthrop, MA 02152
  • 54 Villa Ave Unit 2, Winthrop, MA 02152
    54 Villa Ave Unit 2, Winthrop, MA 02152
    54 Villa Ave Unit 2, Winthrop, MA 02152
    /25

    $839,900 Sold Nov 05, 2025

    • 2,115 Sq Ft
    • $397/SF
    • 54 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2019

    54 Villa Ave Unit 2, Winthrop, MA 02152

    Modern 2019 move-in ready townhouse with coastal charm! This meticulously crafted 3-bedroom, 2.5-bathroom home brimming with natural light and coastal charm with features such as soaring ceilings, walls of windows, and an open floor plan. Key Features: • Statement gas fireplace as living room focal point • Designer kitchen with premium appliances • Private backyard with dedicated driveway parking

    The Reference Group Reference Real Estate

    54 Villa Ave Unit 2, Winthrop, MA 02152
    • 3 Almont St, Winthrop, MA 02152
      3 Almont St, Winthrop, MA 02152
      3 Almont St, Winthrop, MA 02152
      /21

      Est $881,444 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,840 Sq Ft

      3 Almont St, Winthrop, MA 02152

      3 Almont St, Winthrop, MA 02152
  • 10 Somerset Ave Unit 404, Winthrop, MA 02152
    10 Somerset Ave Unit 404, Winthrop, MA 02152
    10 Somerset Ave Unit 404, Winthrop, MA 02152
    /10

    $408,450

    • 1 Bed
    • 1 Bath
    • 546 Sq Ft

    10 Somerset Ave Unit 404, Winthrop, MA 02152

    Welcome to Unit 404 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed studio features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 404, Winthrop, MA 02152
  • 220 Winthrop St Unit 203, Winthrop, MA 02152
    220 Winthrop St Unit 203, Winthrop, MA 02152
    220 Winthrop St Unit 203, Winthrop, MA 02152
    /8

    $1,750 total monthly price

    • 1 Bath
    • 9,999 Sq Ft
    • Apartment for Rent

    220 Winthrop St Unit 203, Winthrop, MA 02152

    Available December 1st! Discover this brand-new, fully renovated studio apartment located in Winthrop center. Situated in an elevator building, the apartment features gleaming hardwood floors, an open concept living room and sleeping area filled with natural light, and a sleek kitchen equipped with stainless steel appliances, including a dishwasher, gas stove, refrigerator, and microwave. The

    Mario Fiume Anzalone Realty

    220 Winthrop St Unit 203, Winthrop, MA 02152
  • 12 Winthrop St, Winthrop, MA 02152
    12 Winthrop St, Winthrop, MA 02152
    12 Winthrop St, Winthrop, MA 02152
    /42

    $880,000 Sold Oct 29, 2025

    • 1,905 Sq Ft
    • $462/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    12 Winthrop St, Winthrop, MA 02152

    THIS INCREDIBLE AND PRIVATE LOCATION OFFERS SO MUCH NATURAL BEAUTY........Stunning Winthrop harbor views from this totally renovated 3 BR, 2 full bath seaside single with garage. Quality upgrades, Open Floor plan, crown moldings, stunning accent wall and amazing oversized windows that invite in amazing views and natural sunlight! Beautiful quartz kitchen with dual cabinet colors, Stainless

    Sharon Tallent Compass

    12 Winthrop St, Winthrop, MA 02152
    • 62 Locust St, Winthrop, MA 02152
      62 Locust St, Winthrop, MA 02152
      62 Locust St, Winthrop, MA 02152
      /33

      Est $786,741 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,412 Sq Ft

      62 Locust St, Winthrop, MA 02152

      62 Locust St, Winthrop, MA 02152

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Real Estate & Homes

Learn more about living in Downtown Winthrop

Home Trends in Downtown Winthrop, MA

On average, homes in Downtown Winthrop, Winthrop sell after 24 days on the market compared to the national average of 53 days. The median sale price for homes in Downtown Winthrop, Winthrop over the last 12 months is $657,500, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$657,500
Median Single Family Sale Price
$723,450
Median Townhouse Sale Price
$849,000
Median 2 Bedroom Sale Price
$389,900
Median 1 Bedroom Sale Price
$545,000
Average Price Per Sq Ft
$440
Number of Homes for Sale
13
Last 12 months Home Sales
47
Months of Supply
3.30
Median List Price
$622,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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