7,586

Winthrop, MA Homes

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  • /26

    $1,299,000

    • 5 Beds
    • 2 Baths
    • 3,754 Sq Ft

    264 Court Rd, Winthrop, MA 02152

    Located in one of the most desirable neighborhoods in town, this grand home has been the home to 4 generations of the same family since it was built. It has been cherished by the same family for over 100 years. Rich original woodwork and timeless character can be found throughout. Step into the sun-filled enclosed front porch before entering the impressive foyer featuring a stunning quarter-sawn

    Elizabeth Ferrara Cottage Hill Real Estate

    264 Court Rd, Winthrop, MA 02152
  • /19

    $5,500 Per Month

    • 5 Beds
    • 2 Baths
    • 2,500 Sq Ft
    • Apartment for Rent

    97 Court Rd Unit 2, Winthrop, MA 02152

    Rare opportunity to rent a spacious ocean-view penthouse in Winthrop offering 5 bedrooms and 2 full baths across approx. 2,500 sq ft on the 2nd and 3rd floors. The 3rd floor features three large sun-filled bedrooms with beautiful water views and a full bath, while the 2nd floor includes two additional bedrooms and a newly renovated full bath—ideal for flexible family living, guest space, or home

    Scarlett Tamburro Gibson Sotheby's International Realty

    97 Court Rd Unit 2, Winthrop, MA 02152
  • /38

    $620,000 Sold May 19, 2025

    240 Bowdoin St, Winthrop, MA 02152

    • 4 Beds
    • 1.5 Baths
    • 1,684 Sq Ft
    • Built 1860

    Last Sold Summary

    • 11% Below List Price
    • $368/SF
    • 15 Days On Market

    Current Estimated Value $635,178

    Last Listing Agent Jenny Golic Lantern Residential

    240 Bowdoin St, Winthrop, MA 02152
    • /12

      Not Listed For Sale

      158 Shirley St Unit 1, Winthrop, MA 02152

      • 1 Bed
      • 1 Bath
      • 700 Sq Ft
      • Built 1920
      158 Shirley St Unit 1, Winthrop, MA 02152

      Last Sold Summary

      • $643/SF
      • 216 Days On Market
      • Last Sold Price $450,000
      • May 09, 2025

      Last Listing Agent Leighann Eruzione Lantern Residential

  • /38

    $515,000

    • 3 Beds
    • 1 Bath
    • 1,325 Sq Ft

    26 Forrest St Unit 1, Winthrop, MA 02152

    Half a block from Winthrop Beach, this spacious 3-bedroom first-floor condo offers over 1,300 square feet of character-filled coastal living in a classic 1890 three-family home. From the moment you enter, you’ll appreciate the welcoming foyer and period details, including Chelsea-tiled fireplaces, high ceilings, and hardwood floors. Built-in AC across the property. A formal living room and a

    Clara Arroyave eXp Realty

    26 Forrest St Unit 1, Winthrop, MA 02152
  • /19

    $2,300 - $2,400

    Total Monthly Price

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

    220 Winthrop St, Winthrop, MA 02152

    Live in one of Winthrop’s most iconic landmark buildings at 220 Winthrop Street, known locally as The Wadsworth Building. Originally a cornerstone of Winthrop Center’s commercial life, this historic structure has been thoughtfully updated to offer distinctive residential apartments above neighborhood retail, blending classic New England character with modern interior finishes.The building

    220 Winthrop St, 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 $480,309

    Last Listing Agent Reserve Team Reference Real Estate

    86 Undine Ave, Winthrop, MA 02152
    • /21

      Not Listed For Sale

      235 Winthrop Shore Dr, Winthrop, MA 02152

      • 7 Beds
      • 4.5 Baths
      • 3,878 Sq Ft
      • Built 1900
      235 Winthrop Shore Dr, Winthrop, MA 02152

      Last Sold Summary

      • $340/SF
      • 7 Days On Market
      • Last Sold Price $1,320,000
      • Apr 29, 2025

      Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  • /32

    $1,300,000

    • 4 Beds
    • 1.5 Baths
    • 2,916 Sq Ft

    24 Fairview St, Winthrop, MA 02152

    Introducing 24 FAIRVIEW STREET - a charming 4-bedroom, 1.5 bath Victorian in a prime, central location offering inside and outside enjoyment . This beautiful home has been enjoyed and maintained by the same family for many years and offers timeless appeal throughout. First floor has a family room, living room with a fireplace, modern kitchen with s/s appliances, separate dining area and a

    Mary Ann Cash Charlesgate Realty Group, llc

    24 Fairview St, Winthrop, MA 02152
  • /10

    $2,500 Per Month

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

    16-18 Seafoam Ave Unit 2, Winthrop, MA 02152

    This charming two-bedroom rental offers the perfect blend of comfort and convenience. Featuring a spacious bonus room that can easily serve as a walk-in closet or a home office, this home is designed to suit your lifestyle. Enjoy ocean views from your private balcony, ideal to enjoy your morning cup of coffee. The property boasts new windows and flooring throughout, providing a fresh feel.

    Alla Rossi Coldwell Banker Realty - Boston

    16-18 Seafoam Ave Unit 2, Winthrop, MA 02152
  • /36

    $715,000 Sold Dec 30, 2025

    19 Pleasant Park Rd, Winthrop, MA 02152

    • 3 Beds
    • 1.5 Baths
    • 1,325 Sq Ft
    • Built 1920

    Last Sold Summary

    • 2% Below List Price
    • $540/SF
    • 35 Days On Market

    Current Estimated Value $701,841

    Last Listing Agent Laura Cohron Fiv Realty Co.

    19 Pleasant Park Rd, Winthrop, MA 02152
    • /31

      Est $805,006 Not Listed For Sale

      187 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

      • 3 Beds
      • 1.5 Baths
      • 1,890 Sq Ft
      • Built 1920
      187 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

      Last Sold Summary

      • 2% Below List Price
      • $437/SF
      • 72 Days On Market
      • Last Sold Price $825,000
      • Apr 25, 2025

      Last Listing Agent The Reference Group Reference Real Estate

  • /38

    $1,450,000

    • 6 Beds
    • 5.5 Baths
    • 5,278 Sq Ft

    100 Sargent St, Winthrop, MA 02152

    Set on a highly desirable corner lot at Sargent & Johnson Ave, this truly one of a kind home offers exceptional space and versatility. Welcoming foyer opens to a spacious living room, while the dining room features a covered porch with ocean views perfect for enjoying sunset evenings. The first floor also includes a bedroom and full bath, plus a kitchen with direct access to the backyard and one

    Elizabeth Ferrara Cottage Hill Real Estate

    100 Sargent St, Winthrop, MA 02152
  • /37

    $2,750

    Total Monthly Price

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

    92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

    92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
  • /26

    $715,000 Sold Jan 27, 2026

    174 Winthrop St Unit 2, Winthrop, MA 02152

    • 3 Beds
    • 2.5 Baths
    • 1,973 Sq Ft
    • Built 1880

    Last Sold Summary

    • 3% Below List Price
    • $362/SF
    • 107 Days On Market

    Last Listing Agent Leighann Eruzione Lantern Residential

    174 Winthrop St Unit 2, Winthrop, MA 02152
    • /16

      Est $481,402 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

      • 2% Above List Price
      • $448/SF
      • 34 Days On Market
      • Last Sold Price $470,000
      • Feb 14, 2024

      Last Listing Agent Jaime Venezia Real Estate Pros Inc.

  • /41

    $549,900 Pending

    • 2 Beds
    • 1 Bath
    • 1,330 Sq Ft

    35 Nevada St Unit 2, Winthrop, MA 02152

    Beautifully refinished condo! Enjoy year-round comfort with central heating and air conditioning. The renovated kitchen is a standout, featuring newer cabinetry, quartz countertops, and a full suite of stainless steel appliances, including a dishwasher and garbage disposal. A spacious walk-in pantry with in-unit washer and dryer adds both convenience and functionality. Hardwood floors run

    Maryellen Russo The Aland Realty Group LLC

    35 Nevada St Unit 2, Winthrop, MA 02152
  • /14

    $2,400 Per Month

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

    1 Pond St Unit 8K, Winthrop, MA 02152

    **AVAILABLE NOW** This is a spacious 1 bedroom/ 1 bath apartment overlooking the beautifully kept grounds of Fort Heath! You will never get tired of your beautiful view from your 8th floor balcony. It is recently remodeled with new laminate flooring throughout as well as new countertops in the kitchen. The unit includes a gas stove, dishwasher and refrigerator. It boasts new kitchen cabinets and

    James Polino Compass

    1 Pond St Unit 8K, Winthrop, MA 02152
  • /19

    $605,000 Sold Apr 30, 2026

    36 Sargent St, Winthrop, MA 02152

    • 4 Beds
    • 2.5 Baths
    • 1,996 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Above List Price
    • $303/SF
    • 9 Days On Market

    Current Estimated Value $774,927

    Last Listing Agent Leighann Eruzione Lantern Residential

    36 Sargent St, Winthrop, MA 02152
    • /20

      Est $460,434 Not Listed For Sale

      148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

      • 1 Bed
      • 1 Bath
      • 738 Sq Ft
      • Built 1900
      148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

      Last Sold Summary

      • 4% Below List Price
      • $650/SF
      • 53 Days On Market
      • Last Sold Price $480,000
      • Jun 13, 2024

      Last Listing Agent Robert Bennett Dream Seekers Realty, LLC

  • /28

    $665,000

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

    51 Harbor View Ave Unit 3, Winthrop, MA 02152

    Penthouse Condo with Harbor Views! Welcome to The Condos at 51 Harborview, ideally perched atop Water Tower Hill where this penthouse residence captures sweeping harbor and Boston skyline views with the ease of just one flight up. The final available home in this boutique collection, Unit 3 offers a rare opportunity for elevated coastal living. Features include 2 bedrooms, 1 bath, plus a bonus

    Susan Doig Donnelly + Co.

    51 Harbor View Ave Unit 3, Winthrop, MA 02152
  • /25

    $3,300

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    66 Sagamore Ave Unit 2, Winthrop, MA 02152

    3 Bedrooms2 BathroomsUtilities: Tenant pays gas, Electric and Oil heat.Laundry: In unit.Parking: 1 off-street included.Pets: No pets.Level: 2nd and 3rd FloorsAvailability: April or MayMove in Costs: Security Deposit and First Month's rent.

    66 Sagamore Ave Unit 2, Winthrop, MA 02152
  • /33

    $1,120,000 Sold Jun 27, 2025

    36 Forrest St, Winthrop, MA 02152

    • 9 Beds
    • 3 Baths
    • 5,178 Sq Ft
    • Built 1890

    Last Sold Summary

    • 12% Above List Price
    • $216/SF
    • 5 Days On Market

    Current Estimated Value $1,147,787

    Last Listing Agent Susan Collins Coldwell Banker Realty - Boston

    36 Forrest St, Winthrop, MA 02152
    • /30

      Est $652,579 Not Listed For Sale

      142 Pleasant St Unit 6, Winthrop, MA 02152

      • 2 Beds
      • 2.5 Baths
      • 1,404 Sq Ft
      • Built 1968
      142 Pleasant St Unit 6, Winthrop, MA 02152

      Last Sold Summary

      • 3% Above List Price
      • $452/SF
      • 36 Days On Market
      • Last Sold Price $635,000
      • Jul 28, 2023

      Last Listing Agent The Reference Group Reference Real Estate

  • /42

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    21 Sewall Ave, Winthrop, MA 02152

    Want to live in Winthrop’s Highlands area? This beautifully renovated 3-BR, 2-Bath home offers the perfect blend of coastal charm and modern upgrades, featuring 2 car parking, water views, hardwood and porcelain tile floors. NO flood insurance required. A recent front room addition with sunset deck enhances both living space and the home’s connection to its surroundings. Chef’s kitchen featuring

    Jodi DiLorenzo Century 21 North East

    21 Sewall Ave, Winthrop, MA 02152
  • /14

    $2,050 Per Month

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

    20 Coral Ave Unit 7, Winthrop, MA 02152

    Looking for a space that fits your fast-paced work life and your need to unplug by the ocean? This updated one-bedroom unit in Winthrop strikes that perfect balance. Tucked just one block from Winthrop Shore Drive beach, this apartment offers more than just a place to live—it gives you a lifestyle. Wake up, grab your morning coffee, take a yoga/fitness class and hop on public bus transportation

    Joanne Vanbuskirk Charlesgate Realty Group, llc

    20 Coral Ave Unit 7, Winthrop, MA 02152
  • /37

    $975,000 Sold Sep 30, 2025

    175 Somerset Ave, Winthrop, MA 02152

    • 5 Beds
    • 2 Baths
    • 3,970 Sq Ft
    • Built 1910

    Last Sold Summary

    • 8% Above List Price
    • $246/SF
    • 5 Days On Market

    Current Estimated Value $1,003,212

    Last Listing Agent Justin Martino Noddle Island Real Estate

    175 Somerset Ave, Winthrop, MA 02152
    • /37

      Est $577,252 Not Listed For Sale

      46 Jefferson St Unit 1, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1900
      46 Jefferson St Unit 1, Winthrop, MA 02152

      Last Sold Summary

      • 5% Above List Price
      • $417/SF
      • 35 Days On Market
      • Last Sold Price $550,000
      • Jan 04, 2024

      Last Listing Agent Nicole Bettano Lantern Residential

  • /42

    $980,000

    • 5 Beds
    • 3 Baths
    • 2,204 Sq Ft

    23 Sagamore Ave, Winthrop, MA 02152

    SPACIOUS, STYLISH AND PRICED TO MOVE! Welcome to the Winthrop Highlands! This beautifully updated home offers three levels of versatile living space, starting with a freshly updated kitchen featuring granite countertops, slate appliances, a center island, and gas cooking—perfect for whipping up meals and memories. The living room flows seamlessly into the dining room, both boasting refinished

    Sharon Tallent Compass

    23 Sagamore Ave, Winthrop, MA 02152
  • /14

    $2,700

    Total Monthly Price

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

    26 Forrest St Unit 2, Winthrop, MA 02152

    Steps from Winthrop Beach, this spacious 2-bedroom condo is the perfect location with easy access to Boston.Suitable for two people, you will love living here.Includes a tandem parking spot, in-unit washer and dryer, and basement storage space.Lease term is flexible - anywhere between 6-12 months. Please message me any questions!The blue line is a 10 min drive away,

    26 Forrest St Unit 2, 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 $426,117

    Last Listing Agent Sharon Tallent Compass

    900 Shirley St, Winthrop, MA 02152
    • /42

      Est $928,978 Not Listed For Sale

      211 Cliff Ave Unit 2, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 2,600 Sq Ft
      • Built 1910
      211 Cliff Ave Unit 2, Winthrop, MA 02152

      Last Sold Summary

      • 2% Above List Price
      • $352/SF
      • 7 Days On Market
      • Last Sold Price $915,000
      • Sep 26, 2024

      Last Listing Agent Mike Hayes Century 21 North East

  • /21

    $979,000

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    43 Loring Rd, Winthrop, MA 02152

    Single Home, Great Location Great Shape Ready to Move In.

    Jason Saphire www.HomeZu.com

    43 Loring Rd, Winthrop, MA 02152
  • /27

    $2,800 Per Month

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

    800 Governors Dr Unit 7, Winthrop, MA 02152

    Welcome to comfortable coastal living at Governors Park — a desirable condominium community in Winthrop, located just across from Boston Harbor with convenient access to the city and local amenities. This rental feature: 2 Spacious bedrooms condo, ample living room, recently renovated modern kitchen with stainless steel appliances, fresh hardwood flooring throughout. Private balcony perfect for

    Claudia Nunez Tremont Realty Group, LLC

    800 Governors Dr Unit 7, Winthrop, MA 02152
  • /13

    $788,000 Sold Aug 14, 2025

    64 Moore St, Winthrop, MA 02152

    • 4 Beds
    • 3 Baths
    • 1,777 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Below List Price
    • $443/SF
    • 52 Days On Market

    Current Estimated Value $777,378

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

    64 Moore St, Winthrop, MA 02152
    • /14

      Est $389,929 Not Listed For Sale

      308 Shirley St Unit 2, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 890 Sq Ft
      • Built 1900
      308 Shirley St Unit 2, Winthrop, MA 02152

      Last Sold Summary

      • 16% Above List Price
      • $378/SF
      • 3 Days On Market
      • Last Sold Price $336,000
      • Dec 26, 2023

      Last Listing Agent Maria Mainini JDS Realty Group

  • /22

    $499,900

    • 1 Bed
    • 1 Bath
    • 947 Sq Ft

    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152

    This move in unit is waiting for you! Unit 210 has an unobstructed view of the ocean and the town of Nahant. as well as a long expanse of lawn and the gazebo. Enjoy your beautiful fully applianced custom kitchen with granite counters and stainless steel appliances , in unit laundry and full bath The hardwood floors throughout add to the value of this condo and the open floor living room/dining

    James Lonergan Lonergan Real Estate

    1 Seal Harbor Rd Unit 210, Winthrop, MA 02152
  • /16

    $2,995

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 9,999 Sq Ft
    • Condo for Rent

    181 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

    Stunning views ocean views. 2 Bedroom, 1 Bath apartment with washer dryer in unit. Street parking. Email for showing today.

    181 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
  • /31

    $459,000 Sold Jul 24, 2025

    47 Dolphin Ave Unit 1, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1935

    Last Sold Summary

    • $420/SF
    • 0 Days On Market

    Current Estimated Value $454,601

    Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

    47 Dolphin Ave Unit 1, Winthrop, MA 02152
    • /35

      Est $627,284 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

      • 3% Below List Price
      • $538/SF
      • 37 Days On Market
      • Last Sold Price $645,000
      • Nov 09, 2023

      Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

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