Suffolk, MA Homes

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  /42

  $650,000

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

  54 Townsend St, Winthrop, MA 02152

  Welcome to this delightful 1926 Cottage/Bungalow located in the highly sought-after Point Shirley section of Winthrop.With 7+ rooms, 3+ bdrms, and 13⁄4 baths, this lovingly maintained home offers timeless character and stunning views. Begin your day on the charming front porch perfect for morning coffee, a good book, or an evening beverage while soaking in the coastal scenery. Inside, the living

  Cathie Curran Charlesgate Realty Group, llc

  54 Townsend St, Winthrop, MA 02152
• 

  

  

  /21

  $2,300 per month

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

  1018 Shirley St Unit 1, Winthrop, MA 02152

  2 bed and 1.5 bath located in Winthrop. Easy access to downtown and public transportation!

  1018 Shirley St Unit 1, Winthrop, MA 02152
• 

  

  

  /40

  $1,250,000 Sold Jul 23, 2025

  • 2,430 Sq Ft
  • $514/SF
  • 3 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1960

  896B Shirley St, Winthrop, MA 02152

  This stunning 5-bed, 3-bath waterfront home offers breathtaking sunrises over the ocean and sunsets over the Boston skyline. The first floor features a bedroom and full bath perfect for guests or single-level living. Large open floor plan with tile floor. Stone fireplace anchors the middle of the room with space for a dining room table over looking the water. The kitchen boasts granite

  Elizabeth Ferrara Cottage Hill Real Estate

  896B Shirley St, Winthrop, MA 02152
• 

  

  

  /34

  Est $780,415 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,211 Sq Ft

  885 Shirley St, Winthrop, MA 02152

  885 Shirley St, Winthrop, MA 02152
• 

  

  

  /35

  $650,000

  • 2 Beds
  • 1 Bath
  • 1,262 Sq Ft

  88 Grand View Ave, Winthrop, MA 02152

  Welcome to the beach! Enjoy breathtaking sunset views over the city your nightly show from home. This charming property is a perfect condo alternative offering rare first-floor living. The open layout features a brand-new kitchen with polished quartz countertops, two bedrooms, and a beautifully renovated full bath. The second bedroom includes in-unit laundry for added convenience. Step out to a

  Elizabeth Ferrara Cottage Hill Real Estate

  88 Grand View Ave, Winthrop, MA 02152
• 

  

  /17

  $3,700 per month

  • 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
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  /27

  $800,000 Sold Jul 14, 2025

  • 1,769 Sq Ft
  • $452/SF
  • 41 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1912

  77 Otis St, Winthrop, MA 02152

  Welcome to coastal living on Point Shirley. This beautifully renovated 4BD, 2BA home invites you to slow down and enjoy life by the beach. Start your day watching the sun rise from your yoga/sunroom, or with a cup of coffee on your front porch. With tall ceilings and an open-concept layout you'll have sight lines from the living room to the dining room to the modern kitchen with quartz counters,

  Molly Walker Coldwell Banker Realty - Scituate

  77 Otis St, Winthrop, MA 02152
• 

  

  /39

  Est $796,717 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,786 Sq Ft

  921 Shirley St, Winthrop, MA 02152

  921 Shirley St, Winthrop, MA 02152
• 

  

  /23

  $829,000

  • 6 Beds
  • 3 Baths
  • 2,184 Sq Ft

  993 Shirley St, Winthrop, MA 02152

  Located near Yirrell Beach, this updated single-family home is ready for its next chapter. Inside, you’ll find an open-concept layout with gorgeous hardwood floors that flow throughout. The modern kitchen is a standout, complete with a shiplap ceiling, granite countertops, and stainless-steel appliances-perfect for daily living and entertaining. The first floor offers one bedroom and a versatile

  Leighann Eruzione Lantern Residential

  993 Shirley St, Winthrop, MA 02152
• 

  

  /33

  $850,000 Sold Jun 26, 2025

  • 2,468 Sq Ft
  • $344/SF
  • 47 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1900

  42 Triton Ave, Winthrop, MA 02152

  Proudly maintained in Winthrop by the Sea! Every detail is designed for comfort & convenience. Featuring 4 bedrooms & 3 full bathrooms. The primary suite is a true retreat, spacious walk-in closet & a stunning spa-like bathroom. Additional space in the lower level provides endless possibilities for a home office, gym, or entertainment area along w/ a 3/4 bathroom. You'll enjoy cooking w/the 5

  Mary Ann Cash Charlesgate Realty Group, llc

  42 Triton Ave, Winthrop, MA 02152
• 

  

  /20

  Est $918,241 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,400 Sq Ft

  953 Shirley St, Winthrop, MA 02152

  953 Shirley St, Winthrop, MA 02152
• 

  

  /21

  $721,000 Pending

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

  138 Grand View Ave, Winthrop, MA 02152

  Experience the thrill and excitement of oceanfront living in this move-in ready seaside single with 3 bedrooms and 1.5 bathrooms. Enjoy stunning, dramatic views of the ocean and Boston skyline. The home features a newly refreshed kitchen and a spacious open floor plan with a fireplace, inviting both ocean views and abundant natural light. Beautiful oak hardwood floors enhance the interior, while

  James Polino Compass

  138 Grand View Ave, Winthrop, MA 02152
• 

  

  /25

  $680,000 Sold Jun 04, 2025

  • 1,586 Sq Ft
  • $429/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1880

  106 Grand View Ave, Winthrop, MA 02152

  Say "HELLO" to your own slice of coastal paradise at 106 Grand View Avenue. This charming 2 bedroom, 1 bathroom waterfront single offers the perfect blend of comfort, convenience & breathtaking views. Enjoy your morning coffee in the family room while watching the boats & planes go & fly by. The open floor concept connects the living, dining & kitchen areas & creates an inviting atmosphere for

  Mary Ann Cash Charlesgate Realty Group, llc

  106 Grand View Ave, Winthrop, MA 02152
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  /26

  Est $644,673 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,060 Sq Ft

  956 Shirley St, Winthrop, MA 02152

  956 Shirley St, Winthrop, MA 02152
• 

  

  /42

  $689,000 Pending

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

  54 Otis St, Winthrop, MA 02152

  Rare opportunity to own two 4,000 Sq ft lots side by side in the beautiful Point Shirley neighborhood. 54 Otis Street and O Otis Street to be sold together in this sale.54 Otis Street in Winthrop, Massachusetts. This charming single-family home built in 1900, offering 2,130 sq ft of living space on a 4,000 sq ft lot. This residence features 8 rooms, providing ample space for comfortable living.

  Stephen Visco East Coast Realty, Inc.

  54 Otis St, Winthrop, MA 02152
• 

  

  /14

  $510,600 Sold May 14, 2025

  • 1,224 Sq Ft
  • $417/SF
  • 32 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1920

  96 Undine Ave, Winthrop, MA 02152

  Experience the charm of this hilltop harbor view 2-bedroom, 1.5-bathroom single-family home with a contemporary touch. The open and airy great room is designed to uplift your spirits, featuring a cathedral ceiling adorned with wood beams, gleaming hardwood floors, and breathtaking ocean and harbor views. Step out onto the private deck directly off the great room for relaxation and uninterrupted

  James Polino Compass

  96 Undine Ave, Winthrop, MA 02152
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  /34

  Est $1,050,259 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,464 Sq Ft

  29 Brewster Ave, Winthrop, MA 02152

  29 Brewster Ave, Winthrop, MA 02152
• 

  

  /25

  $639,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft

  50 Triton Ave, Winthrop, MA 02152

  Updated 2 bedroom, 2 bathroom bungalow located in the picturesque Point Shirley neighborhood of Winthrop. This detached single family home, boasting more than 1,300 square feet of living space, was recently renovated throughout to include wood-look porcelain tile, a brand new kitchen with stainless steel appliances and quartz countertops, a brand new master bathroom with a walk in shower

  Andrew Pike The Persac Group, LLC

  50 Triton Ave, Winthrop, MA 02152
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  /27

  $635,000 Sold May 09, 2025

  • 1,200 Sq Ft
  • $529/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  67 Bay View Ave Unit 1L, Winthrop, MA 02152

  Experience coastal living at its finest in this beautifully renovated 2-bed, 2-bath condo, offering breathtaking views of the bay and the iconic Winthrop water tower. Step inside to discover elegant new flooring, sleek modern appliances, and the convenience of central air and heating. Flooded with natural light, the open-concept living space seamlessly connects to expansive outdoor areas—ideal

  The Reference Group Reference Real Estate

  67 Bay View Ave Unit 1L, Winthrop, MA 02152
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  /33

  Est $576,308 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 931 Sq Ft

  33 Bay View Ave, Winthrop, MA 02152

  33 Bay View Ave, Winthrop, MA 02152
• 

  

  /42

  $680,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,206 Sq Ft

  877 Shirley St, Winthrop, MA 02152

  This updated 1938 bungalow offers the ultimate Winthrop waterfront experience with direct bay access from your backyard and Yirrell Beach directly across the street. The private brick patio provides sweeping views of Snake Island and the Boston skyline—perfect for outdoor entertaining and front-row views of Winthrop's Fourth of July fireworks. Since 2017, this Point Shirley gem has undergone

  Jared Swanson eXp Realty

  877 Shirley St, Winthrop, MA 02152
• 

  

  /32

  $620,000 Sold Apr 28, 2025

  • 1,200 Sq Ft
  • $517/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  65 Bay View Ave Unit 67, Winthrop, MA 02152

  Discover this stunningly renovated 2-bed, 2-bath condo with breathtaking views of the bay and the iconic Winthrop water tower. Step inside to enjoy luxurious new flooring, sleek, modern appliances, and the comfort of central air and heating. Bathed in natural light, the open living spaces flow effortlessly to expansive outdoor areas, perfect for relaxing or entertaining. The crown jewel of this

  The Reference Group Reference Real Estate

  65 Bay View Ave Unit 67, Winthrop, MA 02152
• 

  

  /22

  Est $583,046 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  29 Undine Ave Unit 31, Winthrop, MA 02152

  29 Undine Ave Unit 31, Winthrop, MA 02152
• 

  

  /40

  $1,149,900

  • 6 Beds
  • 3 Baths
  • 2,400 Sq Ft

  1077 Shirley St, Winthrop, MA 02152

  Welcome to 1077-1079 Shirley St, a rare multi-family opportunity in Winthrop’s coveted Point Shirley neighborhood, offering two charming homes just steps from the ocean. Perfect for multi-generational living, investors, or those seeking a flexible coastal lifestyle, this property blends charm, comfort, and stunning ocean views.The main residence features 4 bedrooms and 2 baths, with an inviting

  Jonathan Simon Bohio Realty LLC

  1077 Shirley St, Winthrop, MA 02152
• 

  

  /35

  $595,000 Sold Apr 23, 2025

  • 1,100 Sq Ft
  • $541/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  111 Strandway, Winthrop, MA 02152

  Welcome to the beach life! This cozy 3 bed 2 bath home just steps to Yirrell beach will be your serene escape. The home has hardwood floors and an open floor plan w a bedroom and a bath on the first level. The second level was added in 2018 and boasts 2 bedrooms, 1 with a finished loft space, and an additional bath. The tall ceilings and plentiful windows let the salty breeze and sunshine in.

  Jaclyn Costonis Costonis Realty & Design LLC

  111 Strandway, Winthrop, MA 02152
• 

  

  /21

  Est $641,288 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  28 Tafts Ave, Winthrop, MA 02152

  28 Tafts Ave, Winthrop, MA 02152
• 

  

  /40

  $849,999

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  876 Shirley St Unit 1, Winthrop, MA 02152

  Direct Beach 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 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
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  /24

  $650,000 Sold Apr 09, 2025

  • 1,363 Sq Ft
  • $477/SF
  • 54 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  62 Otis St, Winthrop, MA 02152

  Welcome to this beautifully updated single-family home in Winthrop’s desirable Point Shirley neighborhood. This coastal gem offers 3 spacious bedrooms and 2 full baths, one of which is handicap accessible for added convenience. Recent renovations include a brand-new kitchen with modern cabinets and updated appliances, perfect for culinary enthusiasts. The finished basement provides additional

  Seth Williams Reference Real Estate

  62 Otis St, Winthrop, MA 02152
• 

  

  /25

  Est $719,878 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,736 Sq Ft

  9 Elliot St, Winthrop, MA 02152

  9 Elliot St, Winthrop, MA 02152
• 

  

  /42

  $849,000

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

  32 Hale Ave, Winthrop, MA 02152

  A spectacular hilltop home with unmatched 360 views. A once-in-a-lifetime opportunity to own this exceptional hilltop property offering panoramic views of the Atlantic Ocean, Boston Harbor, Winthrop Harbor, and the Boston skyline. Ocean views from every room and all three decks make this home truly one of a kind. Steeped in history, this site was purposely chosen by Patriot troops during the

  Sharon Tallent Compass

  32 Hale Ave, Winthrop, MA 02152
• 

  

  /34

  $640,000 Sold Jan 21, 2025

  • 1,652 Sq Ft
  • $387/SF
  • 17 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1957

  30 Townsend St, Winthrop, MA 02152

  CHARMING PICTURE POSTCARD CAPE LOCATED IN WINTHROP'S POINT SHIRLEY.......Steps to the ocean to one end of the street and Boston Harbor and Skyline at the other! The first floor has lots to offer with a very pretty living room and dining room, a bright and sunny fully applianced eat in kitchen with sliders to the yard and, a bonus suite with its own bathroom and kitchenette for extended family if

  Sharon Tallent Compass

  30 Townsend St, Winthrop, MA 02152
• 

  

  /42

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,851 Sq Ft

  23 Tafts Ave, Winthrop, MA 02152

  23 Tafts Ave, Winthrop, MA 02152
• 

  

  /8

  $449,900 Pending

  • 1 Bed
  • 1 Bath
  • 852 Sq Ft

  39 Bay View Ave, Winthrop, MA 02152

  Welcome to this beautiful home with updates throughout, located in a relaxing area just 0.2 miles from the water and directly across from Coughlin park. Recent improvements include a new roof, updated flooring, refreshed countertops and cabinets, and a new water heater. The enclosed front porch with heat is currently used as an office, and there's also a small bonus room used as a nursery—perfect

  Devin Brown Byrnes Real Estate Group LLC

  39 Bay View Ave, Winthrop, MA 02152
• 

  

  /42

  $650,000 Sold Jan 17, 2025

  • 1,421 Sq Ft
  • $457/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  70 Triton Ave, Winthrop, MA 02152

  Come discover this charming 3-bedroom, 2-bath home just a block from the harbor, offering a perfect blend of comfort and breathtaking views. Relax on the oversized deck, where you can enjoy spectacular sights of the harbor and city—ideal for entertaining or unwinding. Coughlin Park is a stone's throw away! This delightful property features a high-efficiency gas heating system, a newer roof, and

  Cathie Curran Charlesgate Realty Group, llc

  70 Triton Ave, Winthrop, MA 02152
• 

  

  /40

  Est $655,459 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,171 Sq Ft

  95 Bay View Ave, Winthrop, MA 02152

  95 Bay View Ave, Winthrop, MA 02152
• 

  

  /15

  $399,900 Pending

  • 2 Beds
  • 1 Bath
  • 836 Sq Ft

  208 Grand View Ave, Winthrop, MA 02152

  Location Location Location-this 2 bedroom condo with oceanfront views of the Boston skyline offers a urban and coastal living even with its need for repairs and updating this property holds so much possibility to be transformed into a stunning residence. The condo is situated in perfect spot with breathtaking views of Boston and shimmering waters. Bring your ideas and transform this property

  Anna Jackson Curtis & Colletta Realty Associates

  208 Grand View Ave, Winthrop, MA 02152
• 

  

  /42

  $643,000 Sold Oct 18, 2024

  • 1,496 Sq Ft
  • $430/SF
  • 8 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1909

  97 Triton Ave Unit 99, Winthrop, MA 02152

  Discover coastal living at 97 Triton Ave, a charming single-family residence in the beautiful seaside suburb of Winthrop! This 3 bedroom, 1.5 bath home offers stunning ocean views and glimpses of the Boston skyline. Situated just moments from Point Shirley Beach, Coughlin Park and local yacht clubs, this location is ideal for those who appreciate seaside serenity. Commuters will love the easy

  Kevin Ochoa United Brokers

  97 Triton Ave Unit 99, Winthrop, MA 02152
• 

  

  /20

  Est $540,439 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,064 Sq Ft

  51 Undine Ave, Winthrop, MA 02152

  51 Undine Ave, Winthrop, MA 02152
• 

  

  /26

  $500,000 Pending

  • 2 Beds
  • 1 Bath
  • 694 Sq Ft

  24 Elliot St, Winthrop, MA 02152

  This sun-filled bungalow offers the perfect blend of city access and coastal charm. Located minutes from Boston & steps from the Beach! This home features a private driveway, backyard, spacious deck & garden area—ideal for relaxing or entertaining. The front sunroom is perfect for morning coffee or a quiet reading nook. Enjoy quick access to local restaurants, shops, beaches, and the scenic

  Jonathan Mathews Legacy Realty Advisors LLC

  24 Elliot St, Winthrop, MA 02152
• 

  

  /7

  $550,000 Sold Oct 09, 2024

  • 2,280 Sq Ft
  • $241/SF
  • 208 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  35 Siren St, Winthrop, MA 02152

  Welcome to 35 Siren Street, Winthrop – a prime investment opportunity! This is a two-family residence with ocean views from the top unit and porch, offering potential for both owner-occupants and investors. There's significant value-add potential, making it ideal for a construction loan or a contractor. Act now to secure your foothold in Winthrop's real estate market. SELLER WILL NOT REVIEW ANY

  Cathie Curran Charlesgate Realty Group, llc

  35 Siren St, Winthrop, MA 02152

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