Winthrop, MA Homes

• 

  

  

  /20

  $400,000 Open Sat 12PM - 1:30PM

  • 2 Beds
  • 1 Bath
  • 662 Sq Ft

  53 Trident Ave Unit 204, Winthrop, MA 02152

  Ideally situated just a few homes from the beach, this two-bedroom, pet-friendly condo offers the perfect opportunity to enjoy coastal living in Winthrop. Thoughtfully updated and well maintained, the home blends modern comforts with an unbeatable seaside location. This home features a refreshed kitchen with brand-new stainless steel appliances and a stylish tile backsplash. One of the bedrooms

  Domenico Barbuto DJB Realty Corporation

  53 Trident Ave Unit 204, Winthrop, MA 02152
• 

  

  

  /7

  $1,750 total monthly price

  • Studio
  • 1 Bath
  • 300 Sq Ft
  • Condo for Rent

  94 Winthrop Shore Dr, Winthrop, MA 02152

  Rent$1,750Avail DateNOW (01/01/2026)BedsStudioBaths1Rent IncludesHot WaterSquare Footage225

  94 Winthrop Shore Dr, Winthrop, MA 02152
• 

  

  

  /31

  $459,000 Sold Jul 24, 2025

  47 Dolphin Ave Unit 1, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 1,092 Sq Ft
  • Built 1935

  Last Sold Summary

  • $420/SF
  • 0 Days On Market

  Current Estimated Value $492,933

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  47 Dolphin Ave Unit 1, Winthrop, MA 02152
• 

  

  

  /32

  Est $524,378 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152
• 

  

  

  /38

  $710,000 Open Sat 11:30AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,764 Sq Ft

  960 Shirley St, Winthrop, MA 02152

  Located just one house from the water, this well-maintained 3-bedroom, 2-bath home offers comfortable living in a prime Winthrop location. The freshly painted interior features large, well-proportioned rooms throughout. A fully finished lower level adds valuable living space, while the converted garage provides a unique bar and entertainment area. The private, fully fenced patio is perfect for

  Bridget Conroy Coldwell Banker Realty - Milton

  960 Shirley St, Winthrop, MA 02152
• 

  

  /22

  $2,600 total monthly price

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

  10 Charles St Unit 2, Winthrop, MA 02152

  3+ bedroom unit ready for immediate occupancy. Nestled just steps away from Winthrop Beach, relish in the spaciousness and cleanliness of this charming unit. Indulge in the convenience of a short stroll to restaurants, cozy coffee shops, and more. Benefit from the included off-street parking, ensuring effortless accessibility. The generous living and dining areas offer ample room for relaxation

  Daniel Clucas Reference Real Estate

  10 Charles St Unit 2, Winthrop, MA 02152
• 

  

  /32

  $850,000 Sold Jul 17, 2025

  81 Lowell Rd, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $425/SF
  • 12 Days On Market

  Current Estimated Value $781,983

  Last Listing Agent Randall Horn Entourage Realty LLC

  81 Lowell Rd, Winthrop, MA 02152
• 

  

  /40

  Est $651,474 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,263 Sq Ft

  3 Seal Harbor Rd Unit 232, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 232, Winthrop, MA 02152
• 

  

  /4

  $500,000

  • Land
  • 0.09 Acre
  • $5,555,556 per Acre

  86L Undine Ave, Winthrop, MA 02152

  This offering is about the land and the view. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready site 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, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing structure

  Reserve Team Reference Real Estate

  86L Undine Ave, Winthrop, MA 02152
• 

  

  /4

  $1,800 total monthly price

  • Studio
  • 1 Bath
  • 999 Sq Ft
  • Condo for Rent

  312 Shirley St, Winthrop, MA 02152

  Rent$1,800Avail DateNOW BedsStudioBaths. 1Rent IncludesA/C, Cable, Electricity, Garbage, Gas, Heat, Hot Water, Water

  312 Shirley St, Winthrop, MA 02152
• 

  

  /39

  $900,000 Sold Feb 14, 2025

  5 Charles St, Winthrop, MA 02152

  • 5 Beds
  • 4 Baths
  • 2,157 Sq Ft
  • Built 1900

  Last Sold Summary

  • $417/SF
  • 60 Days On Market

  Current Estimated Value $881,068

  Last Listing Agent Marisol Aldana Century 21 North East

  5 Charles St, Winthrop, MA 02152
• 

  

  /28

  Est $553,993 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,033 Sq Ft

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152
• 

  

  /10

  $399,000 Open Thu 4:45PM - 6:15PM

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  10 Somerset Ave Unit 304, Winthrop, MA 02152

  LAST STUDIO! Unit 304 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed studio features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout.

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 304, Winthrop, MA 02152
• 

  

  /16

  $2,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Apartment for Rent

  117 Winthrop Shore Dr Unit 6, Winthrop, MA 02152

  You deserve to wake up everyday staring at the ocean...and this is the place to do just that! This beautiful, freshly renovated 2 bedroom and 1 bathroom apartment is ready now, across the street from Winthrop Beach and offers the most stunning view of the water. The unit boasts gleaming hardwood floors, all new appliances and a very cool barn door separating the living room and bedroom. The

  James Polino Compass

  117 Winthrop Shore Dr Unit 6, Winthrop, MA 02152
• 

  

  /42

  $785,000 Sold May 16, 2025

  95 Summit Ave Unit 4, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1890

  Last Sold Summary

  • 7% Above List Price
  • $467/SF
  • 6 Days On Market

  Current Estimated Value $777,772

  Last Listing Agent Joseph Schutt Unit Realty Group, LLC

  95 Summit Ave Unit 4, Winthrop, MA 02152
• 

  

  /26

  Est $600,358 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 910 Sq Ft

  3 Seal Harbor Rd Unit 133, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 133, Winthrop, MA 02152
• 

  

  /42

  $865,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,397 Sq Ft

  2 Deane Ave, Winthrop, MA 02152

  Charm & Convenience & Income! Exciting opportunity to own a home w/approved inlaw-ADU/au-pair within walking distance to the ocean! Enjoy views of Boston skyline! Perfect for multi-generation living. Located in Winthrop Highlands this home has been renovated on 4 levels. Natural light pours into every room. The front hall embraces details from its period. First floor features a custom kitchen

  Marina Tramontozzi True North Realty

  2 Deane Ave, Winthrop, MA 02152
• 

  

  /28

  $2,400 total monthly price

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

  25 Pratt St Unit 1, Boston, MA 02134

  Rent:$2,400 / mo.Beds:1 BedBaths:1 BathLaundry:Laundry on SiteUnit Level:1Parking:For Rent, Outdoor, $200 / Month

  25 Pratt St Unit 1, Boston, MA 02134
• 

  

  /42

  $1,325,000 Sold Aug 15, 2025

  45 Highland Ave, Winthrop, MA 02152

  • 10 Beds
  • 4 Baths
  • 4,671 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $284/SF
  • 35 Days On Market

  Current Estimated Value $1,229,024

  Last Listing Agent Jonathan Mathews Legacy Realty Advisors LLC

  45 Highland Ave, Winthrop, MA 02152
• 

  

  /42

  Est $975,008 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,343 Sq Ft

  218 Cliff Ave, Winthrop, MA 02152

  218 Cliff Ave, Winthrop, MA 02152
• 

  

  /17

  $599,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,141 Sq Ft

  142 Pleasant St Unit 12, Winthrop, MA 02152

  Belle Mer is a newer built 16 unit condo association just on the outskirts of vibrant Winthrop Center, Nearby bountiful dining options, a best of North Shore boutique, coffee shops, fitness studios, book store, and unlimited conveniences. The unit is completely modernized with a timeless aesthetic. Seldom available,modern design 2 level floor plan with oversized windows, dramatic tall ceilings,

  Stacey Steck Gibson Sotheby's International Realty

  142 Pleasant St Unit 12, Winthrop, MA 02152
• 

  

  /18

  $3,200 total monthly price

  • 2 Beds
  • 2 Baths
  • 9,999 Sq Ft
  • Apartment for Rent

  5 Fremont St Unit 301, Winthrop, MA 02152

  Welcome home to this beautifully updated 2-bedroom 2-bathroom apartment with bonus room as an office located in an elevator building featuring a spacious living area and a modern kitchen outfitted with sleek stainless steel appliances. Two queen sized bedroom with generous closet space. Third smaller room great for office space. Stay comfortable all year with high-efficiency mini-split heating

  Mario Fiume Anzalone Realty

  5 Fremont St Unit 301, Winthrop, MA 02152
• 

  

  /42

  $777,000 Sold Nov 26, 2025

  32 Hale Ave, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1920

  Last Sold Summary

  • 11% Below List Price
  • $548/SF
  • 144 Days On Market

  Last Listing Agent Sharon Tallent Compass

  32 Hale Ave, Winthrop, MA 02152
• 

  

  /29

  Est $505,790 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  173 Grovers Ave Unit 2, Winthrop, MA 02152

  173 Grovers Ave Unit 2, Winthrop, MA 02152
• 

  

  /12

  $785,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  993 Shirley St, Winthrop, MA 02152

  Located in Winthrop’s highly desirable Point Shirley, this renovated single-family home offers generous living space, a flexible layout, and an unbeatable beachside location while still close to Boston & everyday conveniences.The main level features a renovated open floor plan with hardwood floors & tons of natural light, where living & dining flow seamlessly into a spacious, remodeled kitchen

  Reserve Team Reference Real Estate

  993 Shirley St, Winthrop, MA 02152
• 

  

  /10

  $1,650 total monthly price

  • Studio
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  85 Winthrop Shore Dr, Winthrop, MA 02152

  Welcome to Winthrop! As a peninsula off of Revere & East Boston, this neighborhood provides a seaside lifestyle with amazing views of the city & Boston Harbor! Convenient to MBTA Blue Line at Orient Heights & multiple MBTA bus routes. Many parks & outdoor activities await you here including Belle Isle Marsh, Snake Island, Deer Island, Winthrop Beach, Winthrop Golf Club, Cottage Park & Winthrop

  85 Winthrop Shore Dr, Winthrop, MA 02152
• 

  

  /22

  $719,000 Sold Dec 30, 2025

  92 Plummer Ave, Winthrop, MA 02152

  • 3 Beds
  • 1.5 Baths
  • 1,449 Sq Ft
  • Built 1937

  Last Sold Summary

  • $496/SF
  • 5 Days On Market

  Last Listing Agent Susan DeFelice Keller Williams Realty Boston-Metro | Back Bay

  92 Plummer Ave, Winthrop, MA 02152
• 

  

  /42

  Est $985,139 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,211 Sq Ft

  36 Floyd St, Winthrop, MA 02152

  36 Floyd St, Winthrop, MA 02152
• 

  

  /25

  $349,900

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  100 Governors Dr Unit 118, Winthrop, MA 02152

  FINALLY!!! A Villager unit for sale in the sought after 100 Building! These 2 bedrooms in Governors Park has a renovated bathroom, newer windows and has been freshly painted. Best of all, Unit 118 is on the TOP FLOOR and features a balcony with views of the top of the Boston skyline, where you can also enjoy AMAZING sunsets. This complex features a clubhouse, gym room, in ground pool and tennis

  Peggy Pratt Century 21 North East

  100 Governors Dr Unit 118, Winthrop, MA 02152
• 

  

  /22

  $3,600 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft
  • Apartment for Rent

  31 Cutler St Unit 1, Winthrop, MA 02152

  This charming and especially spacious three-bedroom apartment is just steps from Winthrop Beach. The bus stop to the "T" stop to Boston and Logan airport is four houses down the street. This spacious 1600 square feet first-floor apartment combines comfort and convenience in a very well maintained home. Inside you'll find beautiful hardwood floors throughout which create a warm and inviting

  James Polino Compass

  31 Cutler St Unit 1, Winthrop, MA 02152
• 

  

  /23

  $369,000 Sold Jul 18, 2025

  203 Winthrop Shore Dr Unit 6, Winthrop, MA 02152

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

  Last Sold Summary

  • 6% Above List Price
  • $509/SF
  • 21 Days On Market

  Current Estimated Value $357,796

  Last Listing Agent Charles Roderick eXp Realty

  203 Winthrop Shore Dr Unit 6, Winthrop, MA 02152
• 

  

  /38

  Est $936,697 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,697 Sq Ft

  89 Cliff Ave, Winthrop, MA 02152

  89 Cliff Ave, Winthrop, MA 02152
• 

  

  /29

  $685,995 Pending

  • 2 Beds
  • 2 Baths
  • 1,327 Sq Ft

  3 Seal Harbor Rd Unit 137, Winthrop, MA 02152

  RARELY AVAILABLE "37 stack" spacious 2 bed/2bath corner unit in The Seal Harbor Condominiums. The open dining/living area is the true heart of the home with a working fireplace, gleaming hardwood floors and direct ocean views. The kitchen showcases stone countertops, updated stainless steel appliances, open island concept and plenty of cabinets for storage, blending style with functionality.

  Christine Goldstein Lyv Realty

  3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
• 

  

  /25

  $2,750 total monthly price

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

  92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  Bright & Modern 2-Bed & Studio in Winthrop – Available Now!Step into this beautifully updated 2-bedroom, 1-bathroom and Studio units in Winthrop, offering tons of natural light and stylish finishes throughout. With hardwood floors and an open layout, this apartment combines comfort and convenience in a prime location.Features you'll love:? Spacious bedrooms – Plenty of room to

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

  

  /32

  $775,000 Sold Jan 30, 2026

  100 Cottage Ave, Winthrop, MA 02152

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft
  • Built 1915

  Last Sold Summary

  • 12% Below List Price
  • $338/SF
  • 100 Days On Market

  Last Listing Agent Reserve Team Reference Real Estate

  100 Cottage Ave, Winthrop, MA 02152
• 

  

  /31

  Est $903,818 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,497 Sq Ft

  92 Quincy Ave, Winthrop, MA 02152

  92 Quincy Ave, Winthrop, MA 02152
• 

  

  /11

  $340,000

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft

  800 Governors Dr Unit 6, Winthrop, MA 02152

  Located at 800 Governors Dr U:6 in the charming coastal community of Winthrop, Massachusetts, this condominium presents an inviting home, ready to move in and enjoy. This residence offers a delightful opportunity to experience comfortable living in a convenient setting. The kitchen stands as a testament to thoughtful design, featuring elegant stone countertops complemented by stylish shaker

  Fiorella Marte StartPoint Realty

  800 Governors Dr Unit 6, Winthrop, MA 02152
• 

  

  /14

  $3,300 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Apartment for Rent

  95 Hermon St Unit 1, Winthrop, MA 02152

  Spacious and bright deleaded 3-bedroom apartment located in the heart of Winthrop Center! This large second floor apartment offers the perfect blend of comfort and convenience—just steps from schools, parks, shopping, and restaurants.Enjoy an oversized master bedroom with access to a private balcony, ideal for morning coffee or evening relaxation. The large eat-in kitchen provides plenty of room

  Erica Gore Century 21 Seaport

  95 Hermon St Unit 1, Winthrop, MA 02152
• 

  

  /30

  $950,000 Sold Nov 21, 2025

  40 Cottage Park Rd, Winthrop, MA 02152

  • 5 Beds
  • 3 Baths
  • 2,550 Sq Ft
  • Built 1900

  Last Sold Summary

  • $373/SF
  • 8 Days On Market

  Last Listing Agent The Reference Group Reference Real Estate

  40 Cottage Park Rd, Winthrop, MA 02152
• 

  

  /40

  Est $788,895 Not Listed For Sale

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

  53 Upland Rd, Winthrop, MA 02152

  53 Upland Rd, Winthrop, MA 02152

Showing Results 81 - 120, Page 3 of 18