Winthrop, MA Homes

• 

  

  

  /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

  Kovacs Savage Team Byrnes Real Estate Group LLC

  129 Strandway, Winthrop, MA 02152
• 

  

  

  /10

  $2,200 Per Month

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

  220 Winthrop St Unit 302, Winthrop, MA 02152

  Available NOW! 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 spacious

  Mario Fiume Anzalone Realty

  220 Winthrop St Unit 302, Winthrop, MA 02152
• 

  

  

  /25

  $670,000 Sold Sep 16, 2025

  162 Shirley St Unit 164, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft
  • Built 1884

  Last Sold Summary

  • 8% Below List Price
  • $474/SF
  • 76 Days On Market

  Current Estimated Value $668,748

  Last Listing Agent Jenny Golic Lantern Residential

  162 Shirley St Unit 164, Winthrop, MA 02152
• 

  

  

  /40

  Est $807,792 Not Listed For Sale

  53 Upland Rd, Winthrop, MA 02152

  • 3 Beds
  • 2.5 Baths
  • 1,516 Sq Ft
  • Built 1961

  53 Upland Rd, Winthrop, MA 02152

  Last Sold Summary

  • 3% Above List Price
  • $518/SF
  • 30 Days On Market

  • Last Sold Price $785,000
  • Oct 25, 2024

  Last Listing Agent Louise Touchette Coldwell Banker Realty - Lynnfield
• 

  

  

  /3

  $499,900

  • 4 Beds
  • 1.5 Baths
  • 1,421 Sq Ft

  28 Irwin St, Winthrop, MA 02152

  Handymen, fixers and flippers! Beachside location! Less than 100 yards to the beach. This 4-5 Bedroom single will need a total renovation but all the potential is here! There is a yard, off street parking, a garage, and a gas FHW boiler. The home is habitable. Flood insurance is required.

  James Polino Compass

  28 Irwin St, 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
• 

  

  /15

  $357,000 Sold Apr 24, 2026

  203 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

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

  Last Sold Summary

  • 1% Below List Price
  • $492/SF
  • 13 Days On Market

  Current Estimated Value $351,932

  Last Listing Agent Molly Walker Coldwell Banker Realty - Scituate

  203 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
• 

  

  /36

  Est $728,244 Not Listed For Sale

  404 Revere St, Winthrop, MA 02152

  • 3 Beds
  • 3 Baths
  • 1,563 Sq Ft
  • Built 1900

  404 Revere St, Winthrop, MA 02152

  Last Sold Summary

  • 3% Above List Price
  • $454/SF
  • 21 Days On Market

  • Last Sold Price $710,000
  • Mar 08, 2024

  Last Listing Agent Nicole Bettano Lantern Residential
• 

  

  /42

  $679,000

  • 2 Beds
  • 2 Baths
  • 1,302 Sq Ft

  3 Seal Harbor Rd Unit 342, Winthrop, MA 02152

  Seal Harbor in Winthrop offers an elevated coastal living experience that is unparalleled. Timeless detail inside & out of this building is complemented by white-glove concierge service. Unit 342 is a luxury residence with ocean & pool views from every window. It is conveniently located a few steps from the new elevators & welcomes you into an open floor plan with striking natural sunlight;

  Nancy McLaughlin Redfin Corp.

  3 Seal Harbor Rd Unit 342, Winthrop, MA 02152
• 

  

  /32

  $5,500 Per Month

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Condo for Rent

  141 Grovers Ave Unit 141, Winthrop, MA 02152

  COASTAL LUXURY AT ITS FINEST! This stunning 2,400 sq. ft. oceanfront townhouse offers a sophisticated seaside lifestyle across three expansive levels, just minutes from Boston. The heart of the home is a sun-drenched living area featuring gleaming hardwoods, a cozy fireplace, and seamless access to two private decks—perfect for savoring salty breezes and panoramic water views. The gourmet kitchen

  Alla Rossi Coldwell Banker Realty - Boston

  141 Grovers Ave Unit 141, Winthrop, MA 02152
• 

  

  /20

  $625,000 Sold Dec 03, 2025

  184 Woodside Ave Unit 1, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,138 Sq Ft
  • Built 1880

  Last Sold Summary

  • 1% Below List Price
  • $549/SF
  • 12 Days On Market

  Current Estimated Value $612,013

  Last Listing Agent Michael Forcillo Coldwell Banker Peggy Carter Team

  184 Woodside Ave Unit 1, Winthrop, MA 02152
• 

  

  /42

  Est $962,200 Not Listed For Sale

  45 Grovers Ave Unit 3, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft
  • Built 2006

  45 Grovers Ave Unit 3, Winthrop, MA 02152

  Last Sold Summary

  • 2% Above List Price
  • $442/SF
  • 109 Days On Market

  • Last Sold Price $945,000
  • Sep 27, 2024

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc
• 

  

  /33

  $419,000 Pending

  • 1 Bed
  • 1 Bath
  • 955 Sq Ft

  66 Plummer Ave Unit 3, Winthrop, MA 02152

  Recently reduced and priced to sell! Sun-filled 1BR condo with 900+ sq ft, updated flooring, new appliances, central A/C, private basement space & parking. Prime Winthrop location near beaches, dining & Boston. Ideal for buyers or investors. Don’t miss it!

  Esmerlyn Diaz eXp Realty

  66 Plummer Ave Unit 3, 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
• 

  

  /22

  $570,000 Sold Jan 20, 2026

  87 Hermon St, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,182 Sq Ft
  • Built 1870

  Last Sold Summary

  • 4% Above List Price
  • $482/SF
  • 3 Days On Market

  Current Estimated Value $569,777

  Last Listing Agent James Polino Compass

  87 Hermon St, Winthrop, MA 02152
• 

  

  /29

  Est $913,537 Not Listed For Sale

  100 Sagamore Ave, Winthrop, MA 02152

  • 5 Beds
  • 1.5 Baths
  • 2,608 Sq Ft
  • Built 1900

  100 Sagamore Ave, Winthrop, MA 02152

  Last Sold Summary

  • 1% Below List Price
  • $355/SF
  • 52 Days On Market

  • Last Sold Price $925,000
  • Jul 26, 2024

  Last Listing Agent Christine D'Ambrosio Lantern Residential
• 

  

  /40

  $774,995

  • 4 Beds
  • 2 Baths
  • 1,833 Sq Ft

  26 Shirley St Unit B, Winthrop, MA 02152

  Welcome to where coastal living meets effortless style in the heart of Winthrop. This is more than a home. It’s a lifestyle. Wake up just moments from the ocean, where morning walks along the shoreline become part of your daily routine. Inside, the residence welcomes you with a bright, open flow designed for both comfort and connection—sunlight pouring in, tranquility at its finest, and a layout

  The Boston ONE Team Serhant

  26 Shirley St Unit B, Winthrop, MA 02152
• 

  

  /11

  $2,050 Per Month

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

  20 Coral Ave Unit 10, Winthrop, MA 02152

  Bright and sunny comfortable unit in a very clean, well maintained building down the street from Winthrop Beach. This unit has a galley kitchen with updated countertops, cabinets and backsplash. Very spacious bedroom with an area off the bedroom suitable for an in-home office, walk in closet or an in-home gym area. Updated bathroom with tiled tub/shower combo. This unit has 2 new Greer split

  Joanne Vanbuskirk Charlesgate Realty Group, llc

  20 Coral Ave Unit 10, Winthrop, MA 02152
• 

  

  /27

  $800,000 Sold Jul 14, 2025

  77 Otis St, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 1,769 Sq Ft
  • Built 1912

  Last Sold Summary

  • 4% Below List Price
  • $452/SF
  • 41 Days On Market

  Current Estimated Value $788,224

  Last Listing Agent Molly Walker Coldwell Banker Realty - Scituate

  77 Otis St, Winthrop, MA 02152
• 

  

  /31

  Est $589,346 Not Listed For Sale

  110 Summit Ave Unit 3, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 1916

  110 Summit Ave Unit 3, Winthrop, MA 02152

  Last Sold Summary

  • 3% Above List Price
  • $422/SF
  • 4 Days On Market

  • Last Sold Price $570,000
  • Aug 01, 2023

  Last Listing Agent CJ Lee Redfin Corp.
• 

  

  /40

  $1,299,000

  • 7 Beds
  • 3 Baths
  • 3,989 Sq Ft

  22 Adams St, Winthrop, MA 02152

  Stunning turn of the century three family home in a prime commuter location! Unit 1 &3 offers a spacious layout with large living room, formal dining room, kitchen, 2 bedrooms. Unit 2 offers smilar layout with 3 bedrooms and private deck. Tucked away on a quiet side street just above the town center, yet only a half-block to the bus line, restaurants, and everyday amenities. Enjoy easy access to

  Elizabeth Ferrara Cottage Hill Real Estate

  22 Adams St, Winthrop, MA 02152
• 

  

  /37

  $2,500 - $3,200

  Total Monthly Price

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

  5 Fremont St, Winthrop, MA 02152

  5 Fremont St, 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
• 

  

  /19

  Est $490,487 Not Listed For Sale

  103 Summit Ave Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 965 Sq Ft
  • Built 1910

  103 Summit Ave Unit 2, Winthrop, MA 02152

  Last Sold Summary

  • 6% Below List Price
  • $539/SF
  • 37 Days On Market

  • Last Sold Price $520,000
  • Jul 31, 2024

  Last Listing Agent Andrew Hillman Hillman Real Estate
• 

  

  /9

  $2,900 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

  295 Shirley St Unit 1, Winthrop, MA 02152

  Bright and spacious 2 bedroom 1.5 bath deleaded apartment with off -street parking, in-unit laundry and golf course views! The modern and large eat-in kitchen features granite countertops, tile floors and stainless appliances. Both bathrooms are renovated and neutral. Lots of closet space, hardwood floors throughout in this convenient ground floor unit with parking steps to the door. Great

  Erica Gore Century 21 Seaport

  295 Shirley St Unit 1, Winthrop, MA 02152
• 

  

  /41

  $975,000 Sold Feb 04, 2026

  5 Quincy Ave, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 2,820 Sq Ft
  • Built 1917

  Last Sold Summary

  • 3% Above List Price
  • $346/SF
  • 46 Days On Market

  Current Estimated Value $936,613

  Last Listing Agent William Raye William Raveis R.E. & Home Services

  5 Quincy Ave, Winthrop, MA 02152
• 

  

  /30

  Est $330,247 Not Listed For Sale

  103 Summit Ave Unit 1, Winthrop, MA 02152

  • 1 Bed
  • 1 Bath
  • 894 Sq Ft
  • Built 1910

  103 Summit Ave Unit 1, Winthrop, MA 02152

  Last Sold Summary

  • 5% Above List Price
  • $352/SF
  • 48 Days On Market

  • Last Sold Price $315,000
  • Jun 06, 2024

  Last Listing Agent Michael Ford Coldwell Banker Realty - Framingham
• 

  

  /25

  $3,000

  Total Monthly Price

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

  61 Coral Ave, Winthrop, MA 02152

  Step into luxury at this stunning, top-floor penthouse with breathtaking panoramic views of the ocean. Perfect for a romantic getaway, family vacation, or serene retreat, this exclusive beachfront oasis combines modern elegance with coastal charm. Relax on your private terrace as you enjoy endless sea views, or take a short walk to the beach just steps from your door.Private terrace with

  61 Coral Ave, Winthrop, MA 02152
• 

  

  /27

  $990,000 Sold Apr 16, 2026

  50-52 Wilshire St, Winthrop, MA 02152

  • 6 Beds
  • 2 Baths
  • 2,212 Sq Ft
  • Built 1930

  Last Sold Summary

  • $448/SF
  • 12 Days On Market

  Last Listing Agent Lou Markakis Lynnway Associates

  50-52 Wilshire St, Winthrop, MA 02152
• 

  

  /21

  Est $863,092 Not Listed For Sale

  3 Almont St, Winthrop, MA 02152

  • 5 Beds
  • 2.5 Baths
  • 2,840 Sq Ft
  • Built 1900

  3 Almont St, Winthrop, MA 02152

  Last Sold Summary

  • 4% Above List Price
  • $292/SF
  • 21 Days On Market

  • Last Sold Price $830,000
  • Dec 01, 2023

  Last Listing Agent Emma D'Angelo Charlesgate Realty Group LLC
• 

  

  /10

  $2,600 Per Month

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

  211-213 Pauline St Unit 1R, Winthrop, MA 02152

  Huge 2 bedroom unit with bonus room/office located on the corner of Pauline and Pleasant St right at the bus stop! Gleaming hardwood flooring throughout. Two good sized bedrooms with bonus room for office/nursery,storage. Spacious living room, dining room and kitchen. Washer dryer hook ups. Pets negotiable.

  Josephine Marino DiMarzo Lyv Realty

  211-213 Pauline St Unit 1R, Winthrop, MA 02152
• 

  

  /23

  $1,050,000 Sold Jan 05, 2026

  191 Court Rd Unit 3, Winthrop, MA 02152

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $408/SF
  • 11 Days On Market

  Current Estimated Value $1,032,489

  Last Listing Agent Reserve Team Reference Real Estate

  191 Court Rd Unit 3, Winthrop, MA 02152
• 

  

  /33

  Est $753,117 Not Listed For Sale

  62 Locust St, Winthrop, MA 02152

  • 5 Beds
  • 2 Baths
  • 2,412 Sq Ft
  • Built 1900

  62 Locust St, Winthrop, MA 02152

  Last Sold Summary

  • $311/SF
  • 45 Days On Market

  • Last Sold Price $750,000
  • Aug 29, 2024

  Last Listing Agent Carol St. Pierre Tache Real Estate, Inc.
• 

  

  /12

  $2,500

  Total Monthly Price

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

  900 Governors Dr Unit 17, Winthrop, MA 02152

  This quiet condominium is in the Governor's Park complex in the north section of Winthrop. It features a large primary bedroom with a huge walk-in closet, a generous 2nd bedroom, a completely renovated full bathroom, and a kitchen with lots of cabinet space and all the amenities. New flooring and paint throughout. Card-operated laundry is available on the ground floor.The complex

  900 Governors Dr Unit 17, Winthrop, MA 02152
• 

  

  /34

  $575,000 Sold Jul 01, 2025

  12 Sewall Ave Unit 1, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 896 Sq Ft
  • Built 1925

  Last Sold Summary

  • 3% Above List Price
  • $642/SF
  • 6 Days On Market

  Last Listing Agent Jorge Betancur Century 21 Mario Real Estate

  12 Sewall Ave Unit 1, Winthrop, MA 02152
• 

  

  /40

  Est $845,950 Not Listed For Sale

  143 Revere St Unit 145, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 2,548 Sq Ft
  • Built 1920

  143 Revere St Unit 145, Winthrop, MA 02152

  Last Sold Summary

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

  • Last Sold Price $815,000
  • Jun 05, 2023

  Last Listing Agent Sean Page Signature Page Real Estate, LLC
• 

  

  /7

  $2,800 Per Month

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

  295 Shirley St Unit 2, Winthrop, MA 02152

  Sunny and well-maintained deleaded 2-bedroom unit with beautiful golf course views. The spacious primary bedroom is complemented by a smaller second bedroom, best suited for a home office, nursery, guest room, or compact bedroom setup. The layout also works well as a large 1-bedroom suite. Features include neutral wall colors, updated bathrooms, ample closet space, in-unit laundry hookups, and

  Erica Gore Century 21 Seaport

  295 Shirley St Unit 2, Winthrop, MA 02152
• 

  

  /30

  $765,000 Sold May 16, 2025

  127 Bowdoin St, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft
  • Built 1910

  Last Sold Summary

  • 2% Above List Price
  • $451/SF
  • 22 Days On Market

  Current Estimated Value $763,415

  Last Listing Agent Leighann Eruzione Lantern Residential

  127 Bowdoin St, Winthrop, MA 02152
• 

  

  /42

  Est $666,817 Not Listed For Sale

  465 Winthrop St, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1925

  465 Winthrop St, Winthrop, MA 02152

  Last Sold Summary

  • 28% Above List Price
  • $367/SF
  • 20 Days On Market

  • Last Sold Price $520,000
  • Oct 30, 2023

  Last Listing Agent DalBon & Company Keller Williams Realty Evolution
• 

  

  /12

  $2,400

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Trump Property

  31-33-33 Pleasant Park Rd Unit 3rd Floor, Winthrop, MA 02152

  31-33-33 Pleasant Park Rd Unit 3rd Floor, Winthrop, MA 02152

Showing Results 161 - 200, Page 5 of 18