Winthrop, MA Homes

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  /21

  $669,009

  • 2 Beds
  • 2 Baths
  • 971 Sq Ft

  148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152

  Welcome to your slice of coastal paradise just outside of Boston. Nestled in the quaint seaside town of Winthrop, this stunning condo offers an unparalleled living experience with exceptional water views.Step inside to discover a meticulously designed space, with an open-concept layout that seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere flooded with

  

  Nicole Bettano

  Lantern Residential

  (617) 618-6576

  148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152
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  /21

  $5,500 total monthly price

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

  141 Grovers Ave Unit 141, Winthrop, MA 02152

  Winthrop, MA (Winthrop Highlands) Water-Front Luxury 3 Bedrooms, 3 Baths Townhouse For Rent; FEATURES: 2400 Square Feet Of Beautiful Living Space; Stainless Steel Appliances (stove/refrigerator/dishwasher/microwave); Granite Counter-tops & Kitchen Island; Elegant Cherry Cabinets; Gleaming Hardwood Floor & Ceramic Tile Floors; Central Heating And Air-Conditioning; Fire Place, High Ceilings;

  

  Herman Davis

  Metro North Realty, LLC

  (617) 934-6197

  141 Grovers Ave Unit 141, Winthrop, MA 02152
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  /31

  $680,000 Sold Apr 23, 2025

  620 Shirley St Unit 3, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $502/SF
  • 38 Days On Market

  Last Listing Agent Patrick Fahey Access

  620 Shirley St Unit 3, Winthrop, MA 02152
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  /31

  Est $712,299 Not Listed For Sale

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

  3 Seal Harbor Rd Unit 644, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 644, Winthrop, MA 02152
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  /28

  $399,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,092 Sq Ft

  9 Atlantic St Unit 2, Winthrop, MA 02152

  Experience the best of coastal living just minutes from Boston—close to the city without the high prices! This bright and spacious home features soaring ceilings, abundant natural light, large rooms, and hardwood floors. The traditional dining room with a built-in cabinet adds classic charm, while the fully applianced kitchen offers warm wood cabinetry and an oversized pantry. Enjoy morning

  Mark Anderson Redfin Corp.

  9 Atlantic St Unit 2, Winthrop, MA 02152
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  /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

  

  Juan Lopera-Martinez

  eXp Realty

  (617) 752-6511

  40 Cottage Park Rd Unit 2, Winthrop, MA 02152
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  /26

  $949,000 Sold Oct 03, 2025

  26 Sargent St, Winthrop, MA 02152

  • 5 Beds
  • 2.5 Baths
  • 2,237 Sq Ft
  • Built 1887

  Last Sold Summary

  • 14% Below List Price
  • $424/SF
  • 27 Days On Market

  Last Listing Agent Mike Wetherbee Cameron Real Estate Group

  26 Sargent St, Winthrop, MA 02152
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  /26

  Est $447,101 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft

  249 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

  249 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
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  /15

  $499,000

  • 3 Beds
  • 1 Bath
  • 1,105 Sq Ft

  279 Shirley St Unit 2, Winthrop, MA 02152

  Like-new 3-bedroom condo near the beach with WATER VIEWS! Built in 2023, this sun-filled home features hardwood floors, central air, a stylish kitchen with white shaker cabinets, high-end appliances, and a deeded off-street parking space. Oversized windows for those envious ocean views in the front and the Boston skyline over Winthrop Golf Club in the back. Just minutes to public transportation

  Adam Mundt Kingston Real Estate & Management

  279 Shirley St Unit 2, Winthrop, MA 02152
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  /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

  

  Juan Lopera-Martinez

  eXp Realty

  (617) 676-0450

  40 Cottage Park Rd Unit 3, Winthrop, MA 02152
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  /40

  $560,000 Sold Oct 30, 2025

  41 Sargent St, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1925

  Last Sold Summary

  • $325/SF
  • 2 Days On Market

  Last Listing Agent Erin Dinsmoor Keller Williams Realty Metropolitan

  41 Sargent St, Winthrop, MA 02152
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  /12

  Est $338,273 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 977 Sq Ft

  1100 Governors Dr Unit 4, Winthrop, MA 02152

  1100 Governors Dr Unit 4, Winthrop, MA 02152
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  /4

  $500,000

  • 1 Bed
  • 1 Bath
  • 620 Sq Ft

  86 Undine Ave, Winthrop, MA 02152

  This offering is about the land, the view, and the opportunity to own an affordable single-family property in an exceptional location. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready property sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs,

  The Reference Group Reference Real Estate

  86 Undine Ave, Winthrop, MA 02152
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  /5

  $1,800 per month plus fees

  • Studio
  • 1 Bath
  • Condo for Rent

  312 Shirley St Unit 208, Winthrop, MA 02152

  Fee Disclosure:First Month Rent: $1,800Lock Key Fee: $100Security Deposit: $1,800Disclaimer: The information in this listing may have been gathered from third-party sources including the owner and/or public records. Listings are subject to errors and omissions. Encore Realty disclaims any and all representations or warranties as to the accuracy of this information. Encore

  312 Shirley St Unit 208, Winthrop, MA 02152
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  /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

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  88 Grand View Ave, Winthrop, MA 02152
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  /16

  Est $493,763 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  62 Park Ave Unit 1, Winthrop, MA 02152

  62 Park Ave Unit 1, Winthrop, MA 02152
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  /36

  $722,000 Pending

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

  19 Pleasant Park Rd, Winthrop, MA 02152

  Welcome to 19 Pleasant Park Road - a beautifully updated coastal retreat that blends timeless character with modern comfort. Step inside to discover warm hardwood floors, sun-filled rooms, and a layout designed for easy everyday living. The inviting dining room flows seamlessly into the living space, while the updated kitchen features stainless steel appliances and classic white cabinetry. Both

  Laura Cohron Fiv Realty Co.

  19 Pleasant Park Rd, Winthrop, MA 02152
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  /9

  $2,300 total monthly price

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

  1 Pond St Unit 4D, Winthrop, MA 02152

  **AVAILABLE NOW** This is a spacious 1 bedroom/ 1 bath apartment with a private balcony overlooking the beautifully kept grounds of Fort Heath! It has been 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 a new vanity in bathroom as well as a walk-in

  James Polino Compass

  1 Pond St Unit 4D, Winthrop, MA 02152
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  /34

  $722,000 Sold Sep 25, 2025

  41 Centre St, Winthrop, MA 02152

  • 5 Beds
  • 1.5 Baths
  • 1,776 Sq Ft
  • Built 1910

  Last Sold Summary

  • 2% Below List Price
  • $407/SF
  • 12 Days On Market

  Last Listing Agent Leighann Eruzione Lantern Residential

  41 Centre St, Winthrop, MA 02152
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  /20

  Est $460,820 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 738 Sq Ft

  148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /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
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  /10

  $1,995 per month plus fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  435 Shirley St Unit 24, Winthrop, MA 02152

  1 Bedroom1 BathroomPet Policy: Cat/Dog OkUtilities: Tenant Pays Electric. Heat and Hot Water included.Laundry: In Building.Parking: 1-car Included. Parking Lot.Broker Fee: No FeeLevel: 2nd Floor.Availability: November 24, 2025Fee Disclosure:First Month Rent: $1,995Last Month Rent: $1,995Security Deposit: $1,995

  435 Shirley St Unit 24, Winthrop, MA 02152
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  /41

  $1,175,000 Sold Sep 17, 2025

  72 Sewall Ave, Winthrop, MA 02152

  • 4 Beds
  • 3.5 Baths
  • 2,214 Sq Ft
  • Built 2009

  Last Sold Summary

  • 7% Below List Price
  • $531/SF
  • 15 Days On Market

  Current Estimated Value $1,124,889

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  72 Sewall Ave, Winthrop, MA 02152
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  /28

  Est $632,894 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,668 Sq Ft

  88 Winthrop St, Winthrop, MA 02152

  88 Winthrop St, Winthrop, MA 02152
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  /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
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  /11

  $2,900 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,108 Sq Ft
  • Apartment for Rent

  14 Perkins St Unit 1, Winthrop, MA 02152

  Renovated first-floor two-bedroom, one-bath apartment just steps from the beach in Winthrop. This move-in-ready home features an entry foyer, hardwood floors throughout, and a cozy fireplace. The updated kitchen includes granite countertops and stainless-steel appliances, including a gas range, refrigerator, dishwasher, and microwave.Additional highlights include driveway parking for two cars, a

  Jennifer Salomon eXp Realty

  14 Perkins St Unit 1, Winthrop, MA 02152
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  /26

  $640,000 Sold May 23, 2025

  83 Chester Ave, Winthrop, MA 02152

  • 3 Beds
  • 1.5 Baths
  • 1,050 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Above List Price
  • $610/SF
  • 5 Days On Market

  Current Estimated Value $632,282

  Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

  83 Chester Ave, Winthrop, MA 02152
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  /30

  Est $676,898 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,404 Sq Ft

  142 Pleasant St Unit 6, Winthrop, MA 02152

  142 Pleasant St Unit 6, Winthrop, MA 02152
• 

  

  /11

  $425,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,015 Sq Ft

  900 Shirley St, Winthrop, MA 02152

  NEW AMAZING PRICE! INCREDIBLE OPPORTUNITY, UNLIMITED POTENTIAL.......Single family living/condo alternative in the quaint oceanside location of Point Shirley in Winthrop by the Sea! A desirable open floor plan consists of Living room, Dining room and kitchen with beautiful oak flooring and a very nice large updated full bathroom and 2 good size bedrooms. All on one level for easy living. Ocean

  Sharon Tallent Compass

  900 Shirley St, Winthrop, MA 02152
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  /7

  $3,000 per month plus fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  76 Fremont St Unit 3, Winthrop, MA 02152

  Fee Disclosure:First Month Rent: $3,000Last Month Rent: $3,000Lock Key Fee: $100Security Deposit: $3,000Disclaimer: The information in this listing may have been gathered from third-party sources including the owner and/or public records. Listings are subject to errors and omissions. Encore Realty disclaims any and all representations or warranties as to the accuracy of

  76 Fremont St Unit 3, Winthrop, MA 02152
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  /42

  $940,000 Sold Jul 30, 2025

  19 Orlando Ave, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,470 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $381/SF
  • 15 Days On Market

  Current Estimated Value $935,206

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc

  19 Orlando Ave, Winthrop, MA 02152
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  /37

  Est $583,645 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
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  /2

  $1,300,000

  • 8 Beds
  • 3 Baths
  • 3,708 Sq Ft

  37 Trident Ave, Winthrop, MA 02152

  Winthrop -Hard to Find 3 Family Home - Ocean views from this 3 -Family Home located on quiet one-way street with short walk to the ocean in Winthrop. The first floor unit has kitchen, living room, 2 bedrooms & 1 bath. The second floor unit has kitchen, living room, 3 Bedrooms, 1 bath, washer & dryer in unit. The third floor unit has kitchen, living room, 2 bedrooms, office or den, 1 bath, washer

  David Parish Connor Real Estate

  37 Trident Ave, Winthrop, MA 02152
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  /11

  $3,000 total monthly price

  • 4 Beds
  • 1 Bath
  • 1,498 Sq Ft
  • Apartment for Rent

  21 Nevada St Unit 3, Winthrop, MA 02152

  This four-bedroom apartment with ocean views is located in a well-maintained building at 21 Nevada Street in Winthrop. The apartment includes a kitchen with updated finishes, hardwood floors, fresh paint, and good natural light throughout. The layout offers four bedrooms suitable for sleeping, work, or guest use. Conveniently located near Winthrop Beach, local shops, parks, cafés, and public

  The Reference Group Reference Real Estate

  21 Nevada St Unit 3, Winthrop, MA 02152
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  /40

  $935,000 Sold Jul 10, 2025

  96-98 Woodside Ave, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1920

  Last Sold Summary

  • 4% Above List Price
  • $440/SF
  • 4 Days On Market

  Last Listing Agent John Young Ledge & Young Real Estate

  96-98 Woodside Ave, Winthrop, MA 02152
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  /42

  Est $924,658 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft

  211 Cliff Ave Unit 2, Winthrop, MA 02152

  211 Cliff Ave Unit 2, Winthrop, MA 02152
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  /22

  $719,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,449 Sq Ft

  92 Plummer Ave, Winthrop, MA 02152

  Welcome to this pristine home in a prime neighborhood w/ the harbor and its stunning views at the end of the street. Close to transportation and a quaint center of town.The freshly painted interior has hardwood fls, living room w/ fireplace and sliding doors opening to a fenced-in backyard w/ a patio and garden perfect for relaxing and entertaining. A room off of the living room is flexible space

  Susan DeFelice Keller Williams Realty Boston-Metro | Back Bay

  92 Plummer Ave, Winthrop, MA 02152
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  /6

  $1,695 per month plus fees

  • Studio
  • 1 Bath
  • Condo for Rent

  90 Winthrop Shore Dr Unit 15, Winthrop, MA 02152

  This nice Studio 1 Bath place in the WINTHROP area is available for 01-01-2026. Included Features are: Electric Heat, Front Porch, and Laundry in Coin-Op. 1.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

  90 Winthrop Shore Dr Unit 15, Winthrop, MA 02152
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  /29

  $650,000 Sold Jul 23, 2025

  167 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  • 4 Beds
  • 1.5 Baths
  • 1,836 Sq Ft
  • Built 1903

  Last Sold Summary

  • 7% Below List Price
  • $354/SF
  • 91 Days On Market

  Last Listing Agent Mark Mulkerrin Coldwell Banker Realty - Sharon

  167 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /14

  Est $380,495 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft

  308 Shirley St Unit 2, Winthrop, MA 02152

  308 Shirley St Unit 2, Winthrop, MA 02152

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