Point Shirley Homes

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  /8

  $499,900

  • 2 Beds
  • 1 Bath
  • 1,015 Sq Ft

  900 Shirley St, Winthrop, MA 02152

  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 hardwood oak floors and a very nice large updated full bathroom and 2 good size bedrooms. All on one level for easy living. Ocean breezes,

  Sharon Tallent Compass

  900 Shirley St, Winthrop, MA 02152
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  /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
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  /8

  $500,000 Sold Sep 08, 2025

  • 852 Sq Ft
  • $587/SF
  • 4 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1935

  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
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  /34

  Est $779,647 Not Listed For Sale

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

  885 Shirley St, Winthrop, MA 02152

  885 Shirley St, Winthrop, MA 02152
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  /17

  $424,950

  • 2 Beds
  • 1 Bath
  • 866 Sq Ft

  16 Pebble Ave, Winthrop, MA 02152

  Located just a couple hundred yards from the water, this two-bedroom, one bathroom property offers a rare opportunity for buyers ready to bring a vision to life. Water views can be enjoyed from directly in front of the home. The layout includes two bedrooms and a full bath upstairs, with the main level featuring the kitchen, living room, dining room, half bath, and a large rear pantry. Bring your

  The Ponte Group Keller Williams South Watuppa

  16 Pebble Ave, Winthrop, MA 02152
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  /16

  $2,500 per month plus fees

  • 2 Beds
  • 0.5 Baths
  • 885 Sq Ft
  • Apartment for Rent

  139 Bay View Ave Unit 2, Winthrop, MA 02152

  You have to see this unique 2 bedroom/1 bathroom apartment which is a few steps from Yirrell Beach. There are hardwood floors throughout. The first level has a kitchen with washer and dryer for tenant use, microwave, dishwasher and gas stove. There is a working fireplace in living room with dura-flame logs only to be used. There is a spiral staircase leading to 2 bedrooms on second level. This

  James Polino Compass

  139 Bay View Ave Unit 2, Winthrop, MA 02152
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  /42

  $625,000 Sold Sep 04, 2025

  • 2,130 Sq Ft
  • $293/SF
  • 28 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  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
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  /39

  Est $840,555 Not Listed For Sale

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

  921 Shirley St, Winthrop, MA 02152

  921 Shirley St, Winthrop, MA 02152
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  /40

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft

  916 Shirley St Unit 1, Winthrop, MA 02152

  At 916 Shirley, we redefine coastal luxury living with our exceptional collection of waterfront condos. Immerse yourself in the essence of waterfront living-breathe in the salty ocean air, bask in the warmth of the sun, & let every wave carry you closer to serenity. Here you will find 3 bedrooms, 2.5 bathrooms, 3 private outdoor decks, 3 levels of finished living space, 2 parking spaces, EV

  Mark Sciaraffa Sciaraffa Real Estate, LLC

  916 Shirley St Unit 1, Winthrop, MA 02152
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  /21

  $711,000 Sold Sep 02, 2025

  • 1,792 Sq Ft
  • $397/SF
  • 102 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1991

  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
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  /34

  Est $1,081,839 Not Listed For Sale

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

  29 Brewster Ave, Winthrop, MA 02152

  29 Brewster Ave, Winthrop, MA 02152
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  /5

  $979,000

  • 2 Beds
  • 2.5 Baths
  • 1,561 Sq Ft

  1001 Shirley St Unit 3, Winthrop, MA 02152

  Welcome to The Pearl — Winthrop’s newest luxury address in the coveted Point Shirley neighborhood. These stunning new-construction townhouses offers 2 spacious bedrooms, 2.5 bathrooms, and an open-concept layout with designer finishes throughout. The chef’s kitchen features premium Bosch appliances and custom cabinetry, while both bedrooms boast custom-built walk-in closets for exceptional style

  The Reference Group Reference Real Estate

  1001 Shirley St Unit 3, Winthrop, MA 02152
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  /25

  $615,000 Sold Aug 20, 2025

  • 1,361 Sq Ft
  • $452/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1940

  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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  /33

  Est $613,797 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
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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
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  /42

  $680,000 Sold Aug 12, 2025

  • 1,206 Sq Ft
  • $564/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1938

  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
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  /22

  Est $564,973 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
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  /40

  $829,999

  • 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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  /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
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  /21

  Est $645,430 Not Listed For Sale

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

  28 Tafts Ave, Winthrop, MA 02152

  28 Tafts Ave, Winthrop, MA 02152
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  /35

  $645,000

  • 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
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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
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  /25

  Est $719,094 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
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  /42

  $725,000

  • 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
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  /26

  $480,000 Sold Jun 30, 2025

  • 694 Sq Ft
  • $692/SF
  • 23 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  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
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  /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
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  /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
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  /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
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  /40

  Est $655,925 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
• 

  

  /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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  /20

  Est $523,968 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,064 Sq Ft

  51 Undine Ave, Winthrop, MA 02152

  51 Undine Ave, Winthrop, MA 02152
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  /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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  /20

  Est $596,410 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  55 Undine Ave, Winthrop, MA 02152

  55 Undine Ave, Winthrop, MA 02152
• 

  

  /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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  /27

  Est $751,638 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,586 Sq Ft

  91 Undine Ave, Winthrop, MA 02152

  91 Undine Ave, Winthrop, MA 02152
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  /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
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  /40

  Est $940,161 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,708 Sq Ft

  7 Siren St, Winthrop, MA 02152

  7 Siren St, Winthrop, MA 02152
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  /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
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  /42

  Est $824,772 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,934 Sq Ft

  27 Siren St, Winthrop, MA 02152

  27 Siren St, 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

  The Reference Group Reference Real Estate

  62 Otis St, Winthrop, MA 02152

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