679

Cottage Hill Homes

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  • 546 Shirley St, Winthrop, MA 02152
    546 Shirley St, Winthrop, MA 02152
    546 Shirley St, Winthrop, MA 02152
    /42

    $765,000

    • 4 Beds
    • 2.5 Baths
    • 1,933 Sq Ft

    546 Shirley St, Winthrop, MA 02152

    This is your opportunity to own in beautiful Winthrop by the Sea at an incredible value! This spacious 4+ bedroom, 2.5-bath home offers the perfect blend of character, updates, and an unbeatable location. Relax on warm summer evenings from the inviting wraparound porch, or take a short stroll just one block to Winthrop Beach for sunrise walks and ocean breezes. Inside, you'll find oversized

    Christine D'Ambrosio Bowdoin Real Estate Partners

    546 Shirley St, Winthrop, MA 02152
  • 600 Shirley St Unit 9, Winthrop, MA 02152
    600 Shirley St Unit 9, Winthrop, MA 02152
    600 Shirley St Unit 9, Winthrop, MA 02152
    /39

    $2,350

    Total Monthly Price

    • Studio
    • 1 Bath
    • 400 Sq Ft
    • Condo for Rent

    600 Shirley St Unit 9, Winthrop, MA 02152

    2nd floor walk-up, this studio condominium is for lease starting Sept. 2026. A former waterfront hotel in Winthrop, MA, The Cove, is renovated and modernized. Here is the opportunity to live across the Bay from Boston; Logan Airport is accessible by public transportation. Excellent commuter location or landing-pad! Unit 9 is available either Unfurnished, or Furnished, with a queen-sized bed

    600 Shirley St Unit 9, Winthrop, MA 02152
  • 247 Washington Ave Unit 9, Winthrop, MA 02152
    247 Washington Ave Unit 9, Winthrop, MA 02152
    247 Washington Ave Unit 9, Winthrop, MA 02152
    /23

    $489,000

    Sold Jun 15, 2026

    247 Washington Ave Unit 9, Winthrop, MA 02152

    • 2 Beds
    • 2 Baths
    • 1,116 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $438/SF
    • 46 Days On Market

    Current Estimated Value $488,995

    Last Listing Agent Federico Creatini eXp Realty LLC - Corporate Office

    247 Washington Ave Unit 9, Winthrop, MA 02152
    • 235 Washington Ave Unit 6, Winthrop, MA 02152
      235 Washington Ave Unit 6, Winthrop, MA 02152
      235 Washington Ave Unit 6, Winthrop, MA 02152
      /26

      Est $373,899

      Not Listed For Sale

      235 Washington Ave Unit 6, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 860 Sq Ft
      • Built 1900
      235 Washington Ave Unit 6, Winthrop, MA 02152

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Cathie Curran Charlesgate Realty Group, llc

  • 25 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
    25 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
    25 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
    /27

    $410,000

    Pending
    • 2 Beds
    • 1 Bath
    • 902 Sq Ft

    25 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

    Coastal living at its best! Just steps from the beach, this beautifully maintained 2-bedroom, 1-bath condominium offers the perfect blend of charm, comfort, and convenience. The bright, open-concept living and dining area flows seamlessly into a spacious kitchen featuring rich cabinetry, granite countertops, and large penninsula—ideal for entertaining. A sun-filled enclosed porch provides the

    Jenny Golic Bowdoin Real Estate Partners

    25 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
  • 566 Shirley St Unit 5, Winthrop, MA 02152
    566 Shirley St Unit 5, Winthrop, MA 02152
    566 Shirley St Unit 5, Winthrop, MA 02152
    /14

    $3,100 Per Month

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft
    • Apartment for Rent

    566 Shirley St Unit 5, Winthrop, MA 02152

    Spacious and recently renovated 3-bedroom apartment located on Shirley St. This unit features new vinyl flooring throughout, stainless steel appliances, and Central A/C & Heat for year-round comfort. Enjoy beautiful water views right from your porch! Conveniently located just minutes from Winthrop Beach and Deer Island, with easy access to public transportation and bus stops to Orient Heights

    Sebastian Taborda Broad Sound Real Estate, LLC

    566 Shirley St Unit 5, Winthrop, MA 02152
  • 100 Cottage Ave, Winthrop, MA 02152
    100 Cottage Ave, Winthrop, MA 02152
    100 Cottage Ave, Winthrop, MA 02152
    /32

    $775,000

    Sold Jan 30, 2026

    100 Cottage Ave, Winthrop, MA 02152

    • 3 Beds
    • 2.5 Baths
    • 2,293 Sq Ft
    • Built 1915

    Last Sold Summary

    • 12% Below List Price
    • $338/SF
    • 100 Days On Market

    Current Estimated Value $797,571

    Last Listing Agent Reserve Team Reference Real Estate

    100 Cottage Ave, Winthrop, MA 02152
    • 265 Washington Ave Unit 2A, Winthrop, MA 02152
      265 Washington Ave Unit 2A, Winthrop, MA 02152
      265 Washington Ave Unit 2A, Winthrop, MA 02152
      /18

      Est $267,411

      Not Listed For Sale

      265 Washington Ave Unit 2A, Winthrop, MA 02152

      • 1 Bed
      • 1 Bath
      • 400 Sq Ft
      • Built 1900
      265 Washington Ave Unit 2A, Winthrop, MA 02152

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Pareene Group EXIT Premier Real Estate

  • 566 Shirley St, Winthrop, MA 02152
    566 Shirley St, Winthrop, MA 02152
    566 Shirley St, Winthrop, MA 02152
    /20

    $2,250,000

    • 16 Beds
    • 6 Baths
    • 5,553 Sq Ft

    566 Shirley St, Winthrop, MA 02152

    566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been

    Steve Girolamo Horvath & Tremblay

    566 Shirley St, Winthrop, MA 02152
  • 235 Washington Ave Unit 5, Winthrop, MA 02152
    235 Washington Ave Unit 5, Winthrop, MA 02152
    235 Washington Ave Unit 5, Winthrop, MA 02152
    /15

    $2,875 Per Month

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

    235 Washington Ave Unit 5, Winthrop, MA 02152

    Live the waterfront lifestyle year-round in this bright 2-bedroom, 1-bath Penthouse overlooking three marinas! Gorgeous harbor views from every room, renovated kitchen with island and stainless appliances, open floor plan, abundant natural light, hardwood floors, exposed brick, and a spacious master bedroom with sitting area. Heat and hot water included, plus large storage and laundry in the

    Caroline Ligotti Coldwell Banker Realty - Boston

    235 Washington Ave Unit 5, Winthrop, MA 02152
  • 51 Harbor View Ave Unit 2, Winthrop, MA 02152
    51 Harbor View Ave Unit 2, Winthrop, MA 02152
    51 Harbor View Ave Unit 2, Winthrop, MA 02152
    /30

    $655,000

    Sold May 21, 2026

    51 Harbor View Ave Unit 2, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 1,220 Sq Ft
    • Built 1920

    Last Sold Summary

    • 3% Below List Price
    • $537/SF
    • 31 Days On Market

    Last Listing Agent Susan Doig Donnelly + Co.

    51 Harbor View Ave Unit 2, Winthrop, MA 02152
    • 64 Moore St, Winthrop, MA 02152
      64 Moore St, Winthrop, MA 02152
      64 Moore St, Winthrop, MA 02152
      /13

      Est $786,940

      Not Listed For Sale

      64 Moore St, Winthrop, MA 02152

      • 4 Beds
      • 3 Baths
      • 1,777 Sq Ft
      • Built 1900
      64 Moore St, Winthrop, MA 02152

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  • 600 Shirley St Unit 7, Winthrop, MA 02152
    600 Shirley St Unit 7, Winthrop, MA 02152
    600 Shirley St Unit 7, Winthrop, MA 02152
    /20

    $485,000

    • 1 Bed
    • 1.5 Baths
    • 591 Sq Ft

    600 Shirley St Unit 7, Winthrop, MA 02152

    Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to

    Elizabeth Ferrara Cottage Hill Real Estate

    600 Shirley St Unit 7, Winthrop, MA 02152
  • 789 Shirley St Unit 3, Winthrop, MA 02152
    789 Shirley St Unit 3, Winthrop, MA 02152
    789 Shirley St Unit 3, Winthrop, MA 02152
    /24

    $2,300 Per Month

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

    789 Shirley St Unit 3, Winthrop, MA 02152

    Location,location,waterfront 1 bedroom apartment. Watch the sun rise from your spacious living room or enjoy your morning coffee. Gleaming hardwood floors throughout, ample closet space. Full tile bathroom with bathtub and linen closet. Stackable washer and dryer for tenant use. Open floor plan from dining room to living room. This apartment includes all utilities except cable. There is 1 car

    James Polino Compass

    789 Shirley St Unit 3, Winthrop, MA 02152
  • 12 Park Ave, Winthrop, MA 02152
    12 Park Ave, Winthrop, MA 02152
    12 Park Ave, Winthrop, MA 02152
    /27

    $720,000

    Sold Aug 29, 2025

    12 Park Ave, Winthrop, MA 02152

    • 3 Beds
    • 1.5 Baths
    • 1,172 Sq Ft
    • Built 1890

    Last Sold Summary

    • 3% Above List Price
    • $614/SF
    • 14 Days On Market

    Current Estimated Value $718,521

    Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

    12 Park Ave, Winthrop, MA 02152
    • 51 Harbor View Ave, Winthrop, MA 02152
      51 Harbor View Ave, Winthrop, MA 02152
      51 Harbor View Ave, Winthrop, MA 02152
      /12

      Est $812,227

      Not Listed For Sale

      51 Harbor View Ave, Winthrop, MA 02152

      • 6 Beds
      • 3 Baths
      • 2,308 Sq Ft
      • Built 1920
      51 Harbor View Ave, Winthrop, MA 02152

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

  • 229 Washington Ave Unit 3A, Winthrop, MA 02152
    229 Washington Ave Unit 3A, Winthrop, MA 02152
    229 Washington Ave Unit 3A, Winthrop, MA 02152
    /7

    $219,999

    • 1 Bed
    • 1 Bath
    • 350 Sq Ft

    229 Washington Ave Unit 3A, Winthrop, MA 02152

    Enjoy coastal living in this charming waterfront condominium in Winthrop, offering the perfect balance of convenience and seaside lifestyle. Located just minutes from Boston Logan Airport and with easy access to public transportation including nearby bus routes, the Orient Heights MBTA station, and the East Boston ferry, this home is ideal for commuters seeking quick access to Boston while

    Marcia De Paula REMAX Executive Realty

    229 Washington Ave Unit 3A, Winthrop, MA 02152
  • 23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    /31

    $390,000

    Sold Sep 10, 2025

    23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 679 Sq Ft
    • Built 1902

    Last Sold Summary

    • 2% Below List Price
    • $574/SF
    • 5 Days On Market

    Last Listing Agent Mariel Yovino Compass

    23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    • 831 Shirley St, Winthrop, MA 02152
      831 Shirley St, Winthrop, MA 02152
      831 Shirley St, Winthrop, MA 02152
      /42

      Est $722,516

      Not Listed For Sale

      831 Shirley St, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 1,738 Sq Ft
      • Built 1910
      831 Shirley St, Winthrop, MA 02152

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Elaine Akerberg Elite Realty Experts, LLC

  • 600 Shirley St Unit 11, Winthrop, MA 02152
    600 Shirley St Unit 11, Winthrop, MA 02152
    600 Shirley St Unit 11, Winthrop, MA 02152
    /17

    $299,999

    $20K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 351 Sq Ft

    600 Shirley St Unit 11, Winthrop, MA 02152

    Welcome to The Cove, a distinguished condominium community in coastal Winthrop, offering a spectacular seaside setting with the Boston skyline as the backdrop for unforgettable sunsets. This renovated second-floor studio features wood flooring throughout, an updated kitchen with dining space, and a private balcony off the living area. The unit includes a modern bathroom with a walk-in shower,

    Alla Rossi Coldwell Banker Realty - Boston

    600 Shirley St Unit 11, Winthrop, MA 02152
  • 24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    /31

    $417,000

    Sold Oct 29, 2025

    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 1902

    Last Sold Summary

    • 7% Below List Price
    • $463/SF
    • 57 Days On Market

    Current Estimated Value $427,945

    Last Listing Agent Kevin Ferrara Cottage Hill Real Estate

    24 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    • 62 Park Ave Unit 1, Winthrop, MA 02152
      62 Park Ave Unit 1, Winthrop, MA 02152
      62 Park Ave Unit 1, Winthrop, MA 02152
      /16

      Est $498,231

      Not Listed For Sale

      62 Park Ave Unit 1, Winthrop, MA 02152

      • 3 Beds
      • 1 Bath
      • 1,050 Sq Ft
      • Built 1884
      62 Park Ave Unit 1, Winthrop, MA 02152

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Jaime Venezia Real Estate Pros Inc.

  • 69 Crystal Cove Ave, Winthrop, MA 02152
    69 Crystal Cove Ave, Winthrop, MA 02152
    69 Crystal Cove Ave, Winthrop, MA 02152
    /40

    $899,900

    Pending
    • 4 Beds
    • 2 Baths
    • 1,590 Sq Ft

    69 Crystal Cove Ave, Winthrop, MA 02152

    If you've been waiting for the perfect opportunity to live near the ocean - this is it! Located between Winthrop Harbor and Winthrop Beach, with literal steps to the ocean in either direction, this beautiful, completely renovated single family home offers 4 bedrooms, 2 baths, an updated kitchen, hardwood floors, central air and much more! Great back yard, off-street parking and a beautiful

    Ed Deveau Century 21 Mario Real Estate

    69 Crystal Cove Ave, Winthrop, MA 02152
  • 600 Shirley St Unit 3, Winthrop, MA 02152
    600 Shirley St Unit 3, Winthrop, MA 02152
    600 Shirley St Unit 3, Winthrop, MA 02152
    /32

    $540,000

    Sold Mar 25, 2026

    600 Shirley St Unit 3, Winthrop, MA 02152

    • 2 Beds
    • 2 Baths
    • 773 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $699/SF
    • 253 Days On Market

    Current Estimated Value $533,727

    Last Listing Agent Erika Leigh Pereira Keller Williams Realty Boston Northwest

    600 Shirley St Unit 3, Winthrop, MA 02152
    • 30 Underhill St Unit 1, Winthrop, MA 02152
      30 Underhill St Unit 1, Winthrop, MA 02152
      30 Underhill St Unit 1, Winthrop, MA 02152
      /35

      Est $652,920

      Not Listed For Sale

      30 Underhill St Unit 1, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1900
      30 Underhill St Unit 1, Winthrop, MA 02152

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  • 267 Washington Ave Unit 6, Winthrop, MA 02152
    267 Washington Ave Unit 6, Winthrop, MA 02152
    267 Washington Ave Unit 6, Winthrop, MA 02152
    /10

    $299,900

    Pending
    • 1 Bed
    • 1 Bath
    • 800 Sq Ft

    267 Washington Ave Unit 6, Winthrop, MA 02152

    Super affordable top-floor 1-bedroom condo located less than a block from Winthrop Beach! This surprisingly spacious unit features fresh paint, hardwood floors, high ceilings, partial water views, private parking lot and an HOA fee that includes heat and hot water. An excellent opportunity for first-time buyers or anyone looking to enjoy coastal living at an exceptional value for less than most

    Richard Harkins EWK Realty

    267 Washington Ave Unit 6, Winthrop, MA 02152
  • 41 Harbor View Ave, Winthrop, MA 02152
    41 Harbor View Ave, Winthrop, MA 02152
    41 Harbor View Ave, Winthrop, MA 02152
    /27

    $1,065,000

    Sold Feb 03, 2026

    41 Harbor View Ave, Winthrop, MA 02152

    • 4 Beds
    • 3 Baths
    • 2,028 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Above List Price
    • $525/SF
    • 7 Days On Market

    Current Estimated Value $1,003,759

    Last Listing Agent Brian Perrin Brian J. Perrin Real Estate

    41 Harbor View Ave, Winthrop, MA 02152
    • 247 Washington Ave Unit 8, Winthrop, MA 02152
      247 Washington Ave Unit 8, Winthrop, MA 02152
      247 Washington Ave Unit 8, Winthrop, MA 02152
      /24

      Est $475,840

      Not Listed For Sale

      247 Washington Ave Unit 8, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 1,008 Sq Ft
      • Built 1972
      247 Washington Ave Unit 8, Winthrop, MA 02152

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Daniel Clucas Reference Real Estate

  • 34 Underhill St Unit 4, Winthrop, MA 02152
    34 Underhill St Unit 4, Winthrop, MA 02152
    34 Underhill St Unit 4, Winthrop, MA 02152
    /17

    $495,000

    $15K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 903 Sq Ft

    34 Underhill St Unit 4, Winthrop, MA 02152

    Gut renovated and converted in 2020, this upper-level 2-bedroom, 2-bath condo at 34 Underhill Street brings new construction finishes to one of Winthrop's most sought-after pockets. The white shaker kitchen is fitted with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including electric cooking. Wide plank hardwood floors & high ceilings run

    Reserve Team Reference Real Estate

    34 Underhill St Unit 4, Winthrop, MA 02152
  • 19 Moore St, Winthrop, MA 02152
    19 Moore St, Winthrop, MA 02152
    19 Moore St, Winthrop, MA 02152
    /42

    $844,000

    Sold Apr 30, 2026

    19 Moore St, Winthrop, MA 02152

    • 5 Beds
    • 2.5 Baths
    • 2,212 Sq Ft
    • Built 1890

    Last Sold Summary

    • 2% Above List Price
    • $382/SF
    • 17 Days On Market

    Current Estimated Value $825,506

    Last Listing Agent Kevin Ochoa United Brokers

    19 Moore St, Winthrop, MA 02152
    • 247 Washington Ave Unit 24, Winthrop, MA 02152
      247 Washington Ave Unit 24, Winthrop, MA 02152
      247 Washington Ave Unit 24, Winthrop, MA 02152
      /12

      Est $310,191

      Not Listed For Sale

      247 Washington Ave Unit 24, Winthrop, MA 02152

      • 1 Bed
      • 1 Bath
      • 602 Sq Ft
      • Built 1972
      247 Washington Ave Unit 24, Winthrop, MA 02152

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Cheryl Colarusso Colarusso Realty

  • 70 Moore St Unit PH, Winthrop, MA 02152
    70 Moore St Unit PH, Winthrop, MA 02152
    70 Moore St Unit PH, Winthrop, MA 02152
    /28

    $839,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    70 Moore St Unit PH, Winthrop, MA 02152

    Set on coveted Winthrop Shore Drive, this meticulously maintained penthouse presents an opportunity for elevated, uncomplicated beachside living with breathtaking ocean views from nearly every window. The expansive one-level layout with 1,736 SF of polished living space offers flow and function, comprising three spacious bedrooms, two full baths, 360 degree exposure, three distinct living areas

    Cassie Comstock Compass

    70 Moore St Unit PH, Winthrop, MA 02152
  • 600 Shirley St Unit 1, Winthrop, MA 02152
    600 Shirley St Unit 1, Winthrop, MA 02152
    600 Shirley St Unit 1, Winthrop, MA 02152
    /14

    $399,000

    Sold Apr 17, 2026

    600 Shirley St Unit 1, Winthrop, MA 02152

    • 1 Bed
    • 2 Baths
    • 604 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $661/SF
    • 29 Days On Market

    Current Estimated Value $398,715

    Last Listing Agent The Movement Group Compass

    600 Shirley St Unit 1, Winthrop, MA 02152
    • 267 Washington Ave Unit 5, Winthrop, MA 02152
      267 Washington Ave Unit 5, Winthrop, MA 02152
      267 Washington Ave Unit 5, Winthrop, MA 02152
      /12

      Est $292,790

      Not Listed For Sale

      267 Washington Ave Unit 5, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 610 Sq Ft
      • Built 1900
      267 Washington Ave Unit 5, Winthrop, MA 02152

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Sharon Tallent Compass

  • 600 Shirley St Unit 4, Winthrop, MA 02152
    600 Shirley St Unit 4, Winthrop, MA 02152
    600 Shirley St Unit 4, Winthrop, MA 02152
    /29

    $388,888

    $11K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 585 Sq Ft

    600 Shirley St Unit 4, Winthrop, MA 02152

    8**Back on market due to out of state sale contingency falling through*** WELCOME TO WINTHROP BY THE SEA! THE COVE AT 600 SHIRLEY WAS CONVERTED IN 2022 AND IS LOCATED ON THE SITE OF THE HISTORIC CRYSTAL COVE HOTEL AND HAS AMAZING VIEWS OF BOSTON AND THE ATLANTIC OCEAN! WALK TO THE BEACH, THE YACHT CLUB, VARIOUS RESTAURANTS AND PARKS. THIS 1 BEDROOM UNIT FEATURES NOT ONE BUT TWO BATHROOMS AND 2

    Peggy Pratt Century 21 North East

    600 Shirley St Unit 4, Winthrop, MA 02152
  • 51 Harbor View Ave Unit 3, Winthrop, MA 02152
    51 Harbor View Ave Unit 3, Winthrop, MA 02152
    51 Harbor View Ave Unit 3, Winthrop, MA 02152
    /28

    $660,000

    Sold Jun 29, 2026

    51 Harbor View Ave Unit 3, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 1,304 Sq Ft
    • Built 1920

    Last Sold Summary

    • 1% Below List Price
    • $506/SF
    • 6 Days On Market

    Current Estimated Value $812,227

    Last Listing Agent Susan Doig Donnelly + Co.

    51 Harbor View Ave Unit 3, Winthrop, MA 02152
    • 483 Shirley St Unit 8, Winthrop, MA 02152
      483 Shirley St Unit 8, Winthrop, MA 02152
      483 Shirley St Unit 8, Winthrop, MA 02152
      /14

      Est $289,139

      Not Listed For Sale

      483 Shirley St Unit 8, Winthrop, MA 02152

      • 1 Bed
      • 1 Bath
      • 555 Sq Ft
      • Built 1900
      483 Shirley St Unit 8, Winthrop, MA 02152

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Maghda Amrani Coldwell Banker Realty - Haverhill

  • 16 Underhill St Unit 3, Winthrop, MA 02152
    16 Underhill St Unit 3, Winthrop, MA 02152
    16 Underhill St Unit 3, Winthrop, MA 02152
    /31

    $474,899

    $15K PRICE DROP Pending
    • 3 Beds
    • 1 Bath
    • 1,036 Sq Ft

    16 Underhill St Unit 3, Winthrop, MA 02152

    Welcome to 16 Underhill Rd. #3, a beautifully updated 3-bedroom, 1-bath condo offering 1,036 sq. ft. of move-in ready living space. This bright and inviting home features modern updates, a functional layout, and private laundry in the basement for added convenience. Enjoy your own private deck, perfect for relaxing or entertaining. The property also includes a private garage plus ample additional

    Goldpath Real Estate Group United Brokers

    16 Underhill St Unit 3, Winthrop, MA 02152
  • 48 Crystal Cove Ave Unit 2, Winthrop, MA 02152
    48 Crystal Cove Ave Unit 2, Winthrop, MA 02152
    48 Crystal Cove Ave Unit 2, Winthrop, MA 02152
    /15

    $450,000

    Sold Jul 23, 2026

    48 Crystal Cove Ave Unit 2, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 1,083 Sq Ft
    • Built 1920

    Last Sold Summary

    • $416/SF
    • 16 Days On Market

    Current Estimated Value $444,368

    Last Listing Agent Rogelio Zuniga United Brokers

    48 Crystal Cove Ave Unit 2, Winthrop, MA 02152
    • 11 Perkins St, Winthrop, MA 02152
      11 Perkins St, Winthrop, MA 02152
      11 Perkins St, Winthrop, MA 02152
      /35

      Est $942,358

      Not Listed For Sale

      11 Perkins St, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1900
      11 Perkins St, Winthrop, MA 02152

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Michael Buscanera Atlantic Realty Collective

Showing Results 1 - 40, Page 1 of 17

Massachusetts Suffolk County Winthrop

Real Estate & Homes

Learn more about living in Cottage Hill

Home Prices in Cottage Hill, MA

The median home sale price in Cottage Hill, Winthrop is $540,000, up 4% year-over-year. Homes in Cottage Hill sell in 46 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$728,000
Median 2 Bedroom Sale Price
$490,000
Median 1 Bedroom Sale Price
$388,888
Average Price Per Sq Ft
$560
Number of Homes for Sale
6
Last 12 months Home Sales
19
Months of Supply
3.80
Median List Price
$499,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
4%
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