Cottage Park Homes

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  /35

  $925,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,532 Sq Ft

  200 Woodside Ave, Winthrop, MA 02152

  Incredible opportunity to own a well-maintained 2-family home perfectly suited for investors or owner-occupants in seaside Winthrop! Conveniently located within steps to the water as well as the Center Business District, this property combines location, functionality, & value. Renovated in 2016 & over 2,500 sq ft of living space between two 6+ room units, this multi-family ensures comfort & peace

  Atiyeh Cassidy Blue Sky Realty

  200 Woodside Ave, Winthrop, MA 02152
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  /15

  $2,950 per month

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

  11 Woodside Park Unit 2, Winthrop, MA 02152

  2 bed and 1 bath located in Winthrop. Easy access to downtown and public transportation!

  11 Woodside Park Unit 2, Winthrop, MA 02152
• 

  

  

  /42

  $970,000 Sold Jun 12, 2025

  • 2,916 Sq Ft
  • $333/SF
  • 35 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1930

  52-54 Bellevue Ave, Winthrop, MA 02152

  Welcome to 52-54 Bellevue Avenue in seaside Winthrop Massachusetts. This Brick Two family in Winthrop's coveted Cottage Park Neighborhood boasts 6 beds and 3 baths with over 3,000sf of living space. Paved driveway with ample parking. Large back yard features an oversized detached garage and an in ground pool with brand new liner. Bi-Level Owner's Unit has had a recent cosmetic overhaul. Refreshed

  Nicholas DiCesare Broad Sound Real Estate, LLC

  52-54 Bellevue Ave, Winthrop, MA 02152
• 

  

  

  /21

  Est $451,599 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 779 Sq Ft

  220 Woodside Ave Unit 1, Winthrop, MA 02152

  220 Woodside Ave Unit 1, Winthrop, MA 02152
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  /42

  $950,000 Pending

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

  19 Orlando Ave, Winthrop, MA 02152

  Welcome to this timeless 8-room Whittemore Colonial, perfectly situated in the heart of the highly sought-after Cottage Park neighborhood.This spacious home offers 4 bedrooms, 2.5 baths, and the charm and character of classic architecture paired with modern updates.The main level features a gracious LR with a cozy fireplace, a formal DR highlighted by a stunning leaded glass built-in china

  Cathie Curran Charlesgate Realty Group, llc

  19 Orlando Ave, Winthrop, MA 02152
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  /29

  $4,400 per month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  245 Cottage Park Rd, Winthrop, MA 02152

  Utilities included in this oceanfront enclave circa 1922 with rolling gardens and abundant patio space ideal for social gatherings; gorgeous Boston Harbor and skyline views from nearly every room; and minutes to downtown Boston and Logan Airport. The custom built very well-lighted Eat-in Kitchen has 2 Quartz countertop peninsulas and 2 mahogany butcher block work areas. An adjacent pantry, open

  Timothy Knowlton Beacon Properties

  245 Cottage Park Rd, Winthrop, MA 02152
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  /42

  $845,000 Sold May 30, 2025

  • 2,910 Sq Ft
  • $290/SF
  • 59 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  19 Johnson Ave, Winthrop, MA 02152

  Welcome to 19 Johnson Ave, one of the most coveted streets in Winthrop and in the desirable neighborhood of “Cottage Park”. This property presents an incredible opportunity and endless possibilities for customization. The home offers four levels of living, 5 bedrooms, 2 baths, completely finished lower level, marble fireplace, off-street parking, ocean views and much more! As you explore this

  Laura Wheeler Compass

  19 Johnson Ave, Winthrop, MA 02152
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  /27

  Est $615,654 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,134 Sq Ft

  142 Pleasant St Unit 13, Winthrop, MA 02152

  142 Pleasant St Unit 13, Winthrop, MA 02152
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  /28

  $500,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  66 Plummer Ave Unit 2, Winthrop, MA 02152

  Welcome to 66 Plummer Ave, a well-appointed 3-bedroom, 1-bath condo that offers the perfect blend of comfort, space, and convenience. This sun-filled home features beautiful hardwood floors and a spacious layout with a separate living room, dining room, and kitchen—ideal for both daily living and entertaining. Enjoy your morning coffee or unwind in the evening on either of the two private decks.

  The Reference Group Reference Real Estate

  66 Plummer Ave Unit 2, Winthrop, MA 02152
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  /27

  $2,850 per month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Apartment for Rent

  81 Sunnyside Ave Unit 2, Winthrop, MA 02152

  OCEANSIDE SEVEN ROOM APARTMENT OVERLOOKING SALT WATER MARSH, PRIVATE BEACH ONE BLOCK AWAY, THREE BEDROOMS WITH AN ADDITIONAL ROOM FOR AN OFFICE , FULL DINING AND LIVING ROOM OPEN FLOOR PLAN, ALL NEW WINDOWS SHARED DRIVEWAY AND BACKYARD, STORAGE IN BASEMENT, EAT IN KITCHEN, PLENTY OF CLOSET SPACE. CLOSE TO BEACHES, BUS STOP AND BLUE LINE TRAIN STATION 10 min to airport 15 min to Boston Tenants pay

  Stephanie Macisaac East Coast Realty

  81 Sunnyside Ave Unit 2, Winthrop, MA 02152
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  /27

  $647,000 Sold Dec 27, 2024

  • 1,600 Sq Ft
  • $404/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  96 Bellevue Ave, Winthrop, MA 02152

  This beautifully updated home, just steps from the ocean, offers the perfect blend of modern living and coastal charm. The open-concept kitchen, living, and dining area is designed for both comfort and entertaining. The kitchen features stainless steel appliances, marble countertops, custom ceramic tile flooring, a glass backsplash, and a breakfast bar. The spacious living area showcases a

  Koren Brodin 546 Realty Group

  96 Bellevue Ave, Winthrop, MA 02152
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  /30

  Est $661,133 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
• 

  

  /29

  $989,000 Pending

  • 7 Beds
  • 4 Baths
  • 3,800 Sq Ft

  170 Cottage Park Rd, Winthrop, MA 02152

  A rare opportunity with a 2 family home on one of the best streets in Winthrop! One block to the ocean. Several locale yacht clubs. A few blocks to the town center with many shops, a few great cafes, several excellent restaurants, Great sized yard with a basketball court. One car garage and 4 car off street tandem parking. Refinished hardwoods throughout the entire home. Tiled bathrooms,

  Aaron Daigneault Blue Sky Realty

  170 Cottage Park Rd, Winthrop, MA 02152
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  /14

  $385,000 Sold Dec 18, 2024

  • 1,679 Sq Ft
  • $229/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  55 Johnson Ave Unit 1, Winthrop, MA 02152

  CONTRACTORS! Despite the work needed, this three bedroom condo's LOCATION and harbor views offers INCREDIBLE POTENTIAL. You can change everything except the location and this is a SOUGHT AFTER AREA. Consisting of 1,679 sq. ft., this first floor Philadelphia style unit in a two family home consists of six rooms. It's spacious and READY TO BE RENOVATED.. Harbor side beach, CPYC, schools,

  Mary Ann Cash Charlesgate Realty Group, llc

  55 Johnson Ave Unit 1, Winthrop, MA 02152
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  /35

  Est $1,064,864 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,265 Sq Ft

  200 Pleasant St, Winthrop, MA 02152

  200 Pleasant St, Winthrop, MA 02152
• 

  

  /29

  $612,500 Sold Nov 29, 2024

  • 1,315 Sq Ft
  • $466/SF
  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  35 Plummer Ave, Winthrop, MA 02152

  Seize the opportunity to own a charming home in one of Winthrop's most sought-after locations, all at an attractive price point! This delightful 7-room, 3-bedroom single-family residence greets you with warmth as soon as you step inside. Some homes simply exude an inspiring atmosphere, and this is certainly one of them.The first floor features a bright and inviting living room, a dining room, and

  James Polino Compass

  35 Plummer Ave, Winthrop, MA 02152
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  /30

  Est $666,723 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,318 Sq Ft

  20 Bellevue Ave Unit 2, Winthrop, MA 02152

  20 Bellevue Ave Unit 2, Winthrop, MA 02152
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  /8

  Est $962,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  196 Woodside Ave, Winthrop, MA 02152

  196 Woodside Ave, Winthrop, MA 02152
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  /38

  Est $753,421 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,092 Sq Ft

  73 Plummer Ave, Winthrop, MA 02152

  73 Plummer Ave, Winthrop, MA 02152
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  /42

  Est $761,678 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft

  4 Pico Ave, Winthrop, MA 02152

  4 Pico Ave, Winthrop, MA 02152
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  /7

  Est $736,333 Not Listed For Sale

  • 1 Bed
  • 2,570 Sq Ft

  76 Sunnyside Ave, Winthrop, MA 02152

  76 Sunnyside Ave, Winthrop, MA 02152
• 

  

  /42

  Est $961,266 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,635 Sq Ft

  66 Sunnyside Ave, Winthrop, MA 02152

  66 Sunnyside Ave, Winthrop, MA 02152
• 

  

  /20

  Est $688,326 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,210 Sq Ft

  16 Egleton Park, Winthrop, MA 02152

  16 Egleton Park, Winthrop, MA 02152
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  /40

  Est $1,201,999 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,149 Sq Ft

  131 Bartlett Rd, Winthrop, MA 02152

  131 Bartlett Rd, Winthrop, MA 02152
• 

  

  /19

  Est $902,108 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft

  140 Cottage Park Rd, Winthrop, MA 02152

  140 Cottage Park Rd, Winthrop, MA 02152
• 

  

  /35

  Est $1,130,539 Not Listed For Sale

  • 7 Beds
  • 3 Baths
  • 3,072 Sq Ft

  183 Cottage Park Rd, Winthrop, MA 02152

  183 Cottage Park Rd, Winthrop, MA 02152
• 

  

  /22

  Est $1,008,787 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,024 Sq Ft

  207 Cottage Park Rd, Winthrop, MA 02152

  207 Cottage Park Rd, Winthrop, MA 02152
• 

  

  /41

  Est $891,749 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,809 Sq Ft

  164 Somerset Ave, Winthrop, MA 02152

  164 Somerset Ave, Winthrop, MA 02152
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  /25

  Est $1,247,027 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,044 Sq Ft

  46 Orlando Ave, Winthrop, MA 02152

  46 Orlando Ave, Winthrop, MA 02152
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  /34

  Est $1,040,022 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,623 Sq Ft

  7 Johnson Ave, Winthrop, MA 02152

  7 Johnson Ave, Winthrop, MA 02152
• 

  

  /16

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft

  184 Woodside Ave Unit 2, Winthrop, MA 02152

  184 Woodside Ave Unit 2, Winthrop, MA 02152
• 

  

  /15

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,138 Sq Ft

  184 Woodside Ave Unit 1, Winthrop, MA 02152

  184 Woodside Ave Unit 1, Winthrop, MA 02152
• 

  

  /36

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,292 Sq Ft

  196 Woodside Ave Unit 1, Winthrop, MA 02152

  196 Woodside Ave Unit 1, Winthrop, MA 02152
• 

  

  /34

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,292 Sq Ft

  196 Woodside Ave Unit 2, Winthrop, MA 02152

  196 Woodside Ave Unit 2, Winthrop, MA 02152
• 

  

  /20

  Est $642,933 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  124 Pleasant St Unit 2, Winthrop, MA 02152

  124 Pleasant St Unit 2, Winthrop, MA 02152
• 

  

  /33

  Est $506,711 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,378 Sq Ft

  220 Woodside Ave Unit 2, Winthrop, MA 02152

  220 Woodside Ave Unit 2, Winthrop, MA 02152
• 

  

  /31

  Est $568,812 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,049 Sq Ft

  142 Pleasant St Unit 8, Winthrop, MA 02152

  142 Pleasant St Unit 8, Winthrop, MA 02152
• 

  

  /23

  Est $656,078 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,402 Sq Ft

  142 Pleasant St Unit 7, Winthrop, MA 02152

  142 Pleasant St Unit 7, Winthrop, MA 02152
• 

  

  /32

  Est $654,203 Not Listed For Sale

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

  142 Pleasant St Unit 4, Winthrop, MA 02152

  142 Pleasant St Unit 4, Winthrop, MA 02152
• 

  

  /12

  Est $509,756 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 854 Sq Ft

  142 Pleasant St Unit 16, Winthrop, MA 02152

  142 Pleasant St Unit 16, Winthrop, MA 02152

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