534

Point Shirley Homes

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  • /15

    $549,000

    Open Sun 11AM - 12PM
    • 2 Beds
    • 1 Bath
    • 928 Sq Ft

    16 Billows St Unit B, Winthrop, MA 02152

    This renovated 2-bedroom, 1-bath condo sits in the heart of Winthrop's Point Shirley, offering single-floor living with vaulted ceilings and skylights that give the space a brightness and openness rarely found at this price point. Natural light pours through every room throughout the day, flowing over hardwood floors that run wall to wall and tie the entire living space together seamlessly. Two

    Reserve Team Reference Real Estate

    16 Billows St Unit B, Winthrop, MA 02152
  • /17

    $3,700

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    953 Shirley St Unit 2, Winthrop, MA 02152

    Stylish 3-Bedroom Apartment by the shores of Winthrop!!Welcome to your new home in Boston’s vibrant Winthrop neighborhood! This spacious and updated 3-bedroom, 1-bathroom apartment offers comfort and convenience in a prime location. Each bedroom is generously sized, perfect for creating your own personal retreat. The open living area boasts ample natural light, creating a warm and

    953 Shirley St Unit 2, Winthrop, MA 02152
  • /35

    $605,000

    Sold Dec 19, 2025

    88 Grand View Ave, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 1,262 Sq Ft
    • Built 1945

    Last Sold Summary

    • 9% Below List Price
    • $479/SF
    • 153 Days On Market

    Current Estimated Value $638,170

    Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

    88 Grand View Ave, Winthrop, MA 02152
    • /25

      Est $644,185

      Not Listed For Sale

      50 Triton Ave, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 1,361 Sq Ft
      • Built 1940
      50 Triton Ave, Winthrop, MA 02152

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Andrew Pike The Persac Group, LLC

  • /36

    $669,999

    $30K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,250 Sq Ft

    51 Undine Ave, Winthrop, MA 02152

    Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you’ll find newer flooring, fresh interior

    The Caceda Team Coldwell Banker Realty - Lynnfield

    51 Undine Ave, Winthrop, MA 02152
  • /17

    $3,600

    Total Monthly Price

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

    55 Brewster Ave Unit 55A, Winthrop, MA 02152

    55 Brewster Ave Unit 55A, Winthrop, MA 02152
  • /4

    $450,000

    Sold Apr 23, 2026

    86 Undine Ave, Winthrop, MA 02152

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft
    • Built 1900

    Last Sold Summary

    • 10% Below List Price
    • $726/SF
    • 97 Days On Market

    Current Estimated Value $455,079

    Last Listing Agent Reserve Team Reference Real Estate

    86 Undine Ave, Winthrop, MA 02152
    • /42

      Est $699,853

      Not Listed For Sale

      877 Shirley St, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 1,206 Sq Ft
      • Built 1938
      877 Shirley St, Winthrop, MA 02152

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Jared Swanson eXp Realty LLC - Corporate Office

  • /30

    $809,999

    $20K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,000 Sq Ft

    876 Shirley St Unit 1, Winthrop, MA 02152

    Direct Ocean Front Living. Feel like you're on vacation every day! This spacious 2 level,7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day.Every day the the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining

    Jim Iannuzzi Amo Realty - Boston City Properties

    876 Shirley St Unit 1, Winthrop, MA 02152
  • /21

    $2,400 Per Month

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

    4 Foam St Unit 4, Winthrop, MA 02152

    Available September 15th. Wake up to the salt air in this charming rental tucked into Point Shirley, one of Winthrop's most coveted seaside enclaves. Just moments from the beach, this home puts sand, surf, and sunsets right at your doorstep. Inside, you’ll find a beautifully appointed space with a real seaside bungalow feel. Enjoy the ease of in-unit laundry, no more hauling loads to a laundromat

    Andrew Pike The Persac Group, LLC

    4 Foam St Unit 4, Winthrop, MA 02152
  • /11

    $415,000

    Sold Dec 23, 2025

    900 Shirley St, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 1,015 Sq Ft
    • Built 1908

    Last Sold Summary

    • 17% Below List Price
    • $409/SF
    • 69 Days On Market

    Current Estimated Value $456,044

    Last Listing Agent Sharon Tallent Compass

    900 Shirley St, Winthrop, MA 02152
    • /40

      Est $1,216,978

      Not Listed For Sale

      896B Shirley St, Winthrop, MA 02152

      • 5 Beds
      • 3 Baths
      • 2,430 Sq Ft
      • Built 1960
      896B Shirley St, Winthrop, MA 02152

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  • /42

    $1,324,900

    • 4 Beds
    • 3 Baths
    • 2,640 Sq Ft

    129 Strandway, Winthrop, MA 02152

    Discover true beachfront living at 129 Strandway, where every day feels like vacation. Step from your back door directly into the sand and enjoy panoramic ocean views from the heated sunroom. The main level offers an updated kitchen with marble counters, a cozy fireplaced living room, two bedrooms, and a convenient beach-entry bath. The spacious second-floor primary suite provides its own private

    Mark Savage Byrnes Real Estate Group LLC

    129 Strandway, Winthrop, MA 02152
  • /13

    $3,200

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • Condo for Rent

    953 Shirley St Unit 1, Winthrop, MA 02152

    A gorgeous, newly renovated beach bungalow right at Point Shirely Beach! Bright super sunny! This two bedroom, one bathroom home with DINING ROOM and built-in china cabinet, comes with beautiful, hardwood flooring throughout, stainless steel appliances, laundry and central AC!!! Tons of storage, too! Also, there is parking for two cars. *Pets are negotiable. Public beach access!! The town of

    953 Shirley St Unit 1, Winthrop, MA 02152
  • /42

    $777,000

    Sold Nov 26, 2025

    32 Hale Ave, Winthrop, MA 02152

    • 3 Beds
    • 2 Baths
    • 1,418 Sq Ft
    • Built 1920

    Last Sold Summary

    • 11% Below List Price
    • $548/SF
    • 144 Days On Market

    Current Estimated Value $789,580

    Last Listing Agent Sharon Tallent Compass

    32 Hale Ave, Winthrop, MA 02152
    • /34

      Est $797,029

      Not Listed For Sale

      885 Shirley St, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 1,211 Sq Ft
      • Built 1900
      885 Shirley St, Winthrop, MA 02152

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent James Polino Compass

  • /25

    $840,000

    Open Sun 11AM - 12:30PM $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,837 Sq Ft

    27 Billows St, Winthrop, MA 02152

    This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a

    Reserve Team Reference Real Estate

    27 Billows St, Winthrop, MA 02152
  • /31

    $5,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    876 Shirley St Unit 2, Winthrop, MA 02152

    DIRECT OCEANFRONT walk out onto the sand! OCEAN and CITY VIEWS. Sip your morning coffee and take in the ocean breeze on the back porch and watch the sunset on your front porch. Renovated 3 full bedrooms, 2 full bathrooms, with bonus space for an office.TWO floors of living space featuring an open kitchen and living room and area for formal dining room. Water views from literally every window even

    Leigh Gilmore Gilmore Murphy Realty LLC

    876 Shirley St Unit 2, Winthrop, MA 02152
  • /21

    $650,000

    Sold May 12, 2026

    1080 Shirley St, Winthrop, MA 02152

    • 3 Beds
    • 2.5 Baths
    • 2,278 Sq Ft
    • Built 1930

    Last Sold Summary

    • 7% Below List Price
    • $285/SF
    • 18 Days On Market

    Last Listing Agent Reserve Team Reference Real Estate

    1080 Shirley St, Winthrop, MA 02152
    • /42

      Est $652,134

      Not Listed For Sale

      97 Triton Ave Unit 99, Winthrop, MA 02152

      • 3 Beds
      • 1.5 Baths
      • 1,496 Sq Ft
      • Built 1909
      97 Triton Ave Unit 99, Winthrop, MA 02152

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Kevin Ochoa United Brokers

  • /21

    $715,000

    Open Sun 1PM - 2:30PM $15K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,586 Sq Ft

    52 Pebble Ave, Winthrop, MA 02152

    Cape-style home in Point Shirley, steps from the beach and within Winthrop's most walkable stretch of coastline. Built in 1900 and updated with a remodeled kitchen featuring granite counters and recessed lighting, plus a remodeled full bath with a tiled tub and shower. Original hardwood floors run through the main level and all four bedrooms, paired with bay windows that bring in natural light

    Reserve Team Reference Real Estate

    52 Pebble Ave, Winthrop, MA 02152
  • /8

    $2,300 Per Month

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

    87 Undine Ave Unit 1, Winthrop, MA 02152

    Updated and move-in ready 1-bedroom, 1-bath apartment in Winthrop. All utilities included. Features a spacious living and dining area, walk-in closet, private deck, and water views from both the bedroom and deck. Clean, well-maintained, and located in a quiet, charming neighborhood. Available 9/1

    Daniel Clucas Reference Real Estate

    87 Undine Ave Unit 1, Winthrop, MA 02152
  • /15

    $735,000

    Sold Jun 15, 2026

    92 Undine Ave, Winthrop, MA 02152

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $453/SF
    • 12 Days On Market

    Current Estimated Value $727,552

    Last Listing Agent Reserve Team Reference Real Estate

    92 Undine Ave, Winthrop, MA 02152
    • /32

      Est $1,049,343

      Not Listed For Sale

      65 Bay View Ave Unit 67, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1910
      65 Bay View Ave Unit 67, Winthrop, MA 02152

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent The Reference Group Reference Real Estate

  • /38

    $695,000

    Sold May 18, 2026

    960 Shirley St, Winthrop, MA 02152

    • 3 Beds
    • 1.5 Baths
    • 1,764 Sq Ft
    • Built 1910

    Last Sold Summary

    • 3% Below List Price
    • $394/SF
    • 148 Days On Market

    Current Estimated Value $700,247

    Last Listing Agent Bridget Conroy Coldwell Banker Realty - Milton

    960 Shirley St, Winthrop, MA 02152
    • /35

      Est $918,825

      Not Listed For Sale

      111 Strandway, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1900
      111 Strandway, Winthrop, MA 02152

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Jaclyn Costonis Costonis Realty & Design LLC

  • /8

    $500,000

    Sold Sep 08, 2025

    39 Bay View Ave, Winthrop, MA 02152

    • 1 Bed
    • 1 Bath
    • 852 Sq Ft
    • Built 1935

    Last Sold Summary

    • 11% Above List Price
    • $587/SF
    • 4 Days On Market

    Current Estimated Value $508,714

    Last Listing Agent Devin Alicea-Bailey Byrnes Real Estate Group LLC

    39 Bay View Ave, Winthrop, MA 02152
    • /26

      Est $504,683

      Not Listed For Sale

      24 Elliot St, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 694 Sq Ft
      • Built 1900
      24 Elliot St, Winthrop, MA 02152

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Jonathan Mathews Legacy Realty Advisors LLC

  • /12

    $815,000

    Sold Feb 27, 2026

    993 Shirley St, Winthrop, MA 02152

    • 5 Beds
    • 3.5 Baths
    • 2,550 Sq Ft
    • Built 1920

    Last Sold Summary

    • 4% Above List Price
    • $320/SF
    • 6 Days On Market

    Last Listing Agent Reserve Team Reference Real Estate

    993 Shirley St, Winthrop, MA 02152
    • /14

      Est $573,248

      Not Listed For Sale

      96 Undine Ave, Winthrop, MA 02152

      • 2 Beds
      • 1.5 Baths
      • 1,224 Sq Ft
      • Built 1920
      96 Undine Ave, Winthrop, MA 02152

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent James Polino Compass

  • /42

    $620,000

    Sold Nov 21, 2025

    54 Townsend St, Winthrop, MA 02152

    • 4 Beds
    • 2 Baths
    • 1,483 Sq Ft
    • Built 1926

    Last Sold Summary

    • 5% Below List Price
    • $418/SF
    • 87 Days On Market

    Current Estimated Value $653,638

    Last Listing Agent Cathie Curran Charlesgate Realty Group, llc

    54 Townsend St, Winthrop, MA 02152
    • /20

      Est $558,926

      Not Listed For Sale

      55 Undine Ave, Winthrop, MA 02152

      • 3 Beds
      • 1 Bath
      • 1,020 Sq Ft
      • Built 1953
      55 Undine Ave, Winthrop, MA 02152

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent The Reference Group Reference Real Estate

  • /42

    $625,000

    Sold Sep 04, 2025

    54 Otis St, Winthrop, MA 02152

    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft
    • Built 1900

    Last Sold Summary

    • 17% Below List Price
    • $293/SF
    • 28 Days On Market

    Current Estimated Value $671,976

    Last Listing Agent Stephen Visco East Coast Realty, Inc.

    54 Otis St, Winthrop, MA 02152
    • /27

      Est $707,008

      Not Listed For Sale

      91 Undine Ave, Winthrop, MA 02152

      • 3 Beds
      • 1.5 Baths
      • 1,586 Sq Ft
      • Built 1970
      91 Undine Ave, Winthrop, MA 02152

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent James Polino Compass

  • /21

    $711,000

    Sold Sep 02, 2025

    138 Grand View Ave, Winthrop, MA 02152

    • 3 Beds
    • 1.5 Baths
    • 1,792 Sq Ft
    • Built 1991

    Last Sold Summary

    • 16% Below List Price
    • $397/SF
    • 102 Days On Market

    Current Estimated Value $761,431

    Last Listing Agent James Polino Compass

    138 Grand View Ave, Winthrop, MA 02152
    • /40

      Est $924,492

      Not Listed For Sale

      7 Siren St, Winthrop, MA 02152

      • 4 Beds
      • 2 Baths
      • 2,708 Sq Ft
      • Built 1753
      7 Siren St, Winthrop, MA 02152

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

  • /28

    $610,000

    Sold Nov 21, 2025

    19 Maryland Ave, Winthrop, MA 02152

    • 3 Beds
    • 1 Bath
    • 1,151 Sq Ft
    • Built 1955

    Last Sold Summary

    • 2% Above List Price
    • $530/SF
    • 28 Days On Market

    Current Estimated Value $634,388

    Last Listing Agent Nikki Palladino Lyv Realty

    19 Maryland Ave, Winthrop, MA 02152
    • /42

      Est $823,924

      Not Listed For Sale

      27 Siren St, Winthrop, MA 02152

      • 4 Beds
      • 2 Baths
      • 2,934 Sq Ft
      • Built 1900
      27 Siren St, Winthrop, MA 02152

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Nicole Bettano Real Broker MA, LLC

  • /17

    $400,000

    Sold Dec 19, 2025

    16 Pebble Ave, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 866 Sq Ft
    • Built 1900

    Last Sold Summary

    • 6% Below List Price
    • $462/SF
    • 70 Days On Market

    Current Estimated Value $430,057

    Last Listing Agent The Ponte Group Keller Williams South Watuppa

    16 Pebble Ave, Winthrop, MA 02152
    • /7

      Est $787,307

      Not Listed For Sale

      35 Siren St, Winthrop, MA 02152

      • 5 Beds
      • 2 Baths
      • 2,280 Sq Ft
      • Built 1900
      35 Siren St, Winthrop, MA 02152

      Last Sold Summary

      • 208 Days On Market

      Last Listing Agent Cathie Curran Charlesgate Realty Group, llc

Showing Results 1 - 40, Page 1 of 14

Home Price Trends

Median Sale Price
$620,000
Median Single Family Sale Price
$682,499
Median Townhouse Sale Price
$605,000
Median 2 Bedroom Sale Price
$482,000
Median 1 Bedroom Sale Price
$475,000
Average Price Per Sq Ft
$471
Number of Homes for Sale
6
Last 12 months Home Sales
13
Months of Supply
5.50
Median List Price
$715,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-3%
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