Winthrop, MA Homes

• 

  

  

  /22

  $615,000

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

  142 Pleasant St Unit 12, Winthrop, MA 02152

  Seaside vibes so close to Boston. If you desire a newer built condominium in a prime Winthrop Center location, Belle Mer is a professionally managed association with 15 of 16 units owner occupied. Kitchen equipped with stainless Bosch appliances, wine cooler, + wonderful island to gather for enjoyment. Harbor views from the main bedroom, incredible closet space, and inviting window seat. Lofty

  Stacey Steck Gibson Sotheby's International Realty

  142 Pleasant St Unit 12, Winthrop, MA 02152
• 

  

  

  /19

  $2,950 Per Month

  • 1 Bed
  • 2 Baths
  • 604 Sq Ft
  • Condo for Rent

  600 Shirley St Unit 1, Winthrop, MA 02152

  HEAT AND HOT WATER INCLUDED! Welcome to The Cove at 600, a premier condominium community set on the historic grounds of the former Crystal Cove Hotel. This beautifully renovated and freshly painted first-floor unit offers 1 bedroom/2 full baths, delivering the perfect blend of comfort and coastal living. Thoughtfully updated throughout, this home features a modern kitchen w/new stainless

  Robin Capone Irving Realty

  600 Shirley St Unit 1, Winthrop, MA 02152
• 

  

  

  /39

  $650,000 Sold Sep 30, 2025

  One Seal Harbor Rd Unit 604, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1983

  Last Sold Summary

  • $578/SF
  • 8 Days On Market

  Last Listing Agent Marina Tramontozzi True North Realty

  One Seal Harbor Rd Unit 604, Winthrop, MA 02152
• 

  

  

  /38

  Est $523,520 Not Listed For Sale

  3 Seal Harbor Rd Unit 541, Winthrop, MA 02152

  • 1 Bed
  • 1 Bath
  • 871 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 541, Winthrop, MA 02152

  Last Sold Summary

  • 1% Above List Price
  • $592/SF
  • 41 Days On Market

  • Last Sold Price $516,000
  • Aug 01, 2023

  Last Listing Agent Mark Carangelo Mark Carangelo
• 

  

  

  /26

  $1,650,000

  • 6 Beds
  • 6 Baths
  • 4,122 Sq Ft

  304 Shirley St, Winthrop, MA 02152

  Situated just steps from the sand, 304 Shirley presents a rare opportunity to own a fully occupied 6-unit building in one of Winthrop's most desirable seaside neighborhoods. Each unit is a well-maintained 1-bedroom, offering consistent rental income and strong tenant demand. This beachside property is perfectly positioned near local shops, restaurants, and public transportation, making it a

  Reserve Team Reference Real Estate

  304 Shirley St, Winthrop, MA 02152
• 

  

  /16

  $2,995

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 9,999 Sq Ft
  • Condo for Rent

  181 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  Stunning views ocean views. 2 Bedroom, 1 Bath apartment with washer dryer in unit. Street parking. Email for showing today.

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

  

  /23

  $536,000 Sold Jan 30, 2026

  28 Pearl Ave Unit 3, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $419/SF
  • 58 Days On Market

  Current Estimated Value $533,151

  Last Listing Agent Reserve Team Reference Real Estate

  28 Pearl Ave Unit 3, Winthrop, MA 02152
• 

  

  /32

  Est $529,656 Not Listed For Sale

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152

  Last Sold Summary

  • 4% Above List Price
  • $607/SF
  • 43 Days On Market

  • Last Sold Price $510,000
  • May 22, 2023

  Last Listing Agent Sharon Tallent Compass
• 

  

  /41

  $999,900

  • 7 Beds
  • 3 Baths
  • 3,628 Sq Ft

  308 Bowdoin St, Winthrop, MA 02152

  This spacious multi-family offers 7 bedrooms and 3 full baths across 3,628 sq ft, with high ceilings on a 6,429 sq ft lot. Rarely available in Winthrop, it delivers exceptional size, flexibility, and strong rental potential. A cabin-style garage plus a driveway for 4 cars adds convenience, while the lot provides inviting outdoor space. Interiors are well maintained and move-in ready.The

  Jefri Liriano Liriano Realty

  308 Bowdoin St, Winthrop, MA 02152
• 

  

  /14

  $2,600 Per Month

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

  267 Washington Ave Unit 5, Winthrop, MA 02152

  This top floor 2 bedroom and 1 bath condo can be rented furnished or unfurnished. If it is rented furnished the rent is $2,750/month. It is equipped with a modern kitchen, gas stove, dishwasher, microwave and hardwood floors throughout. The unit is very conveniently located across from bus stop to Orient Heights and a very short walk to Winthrop Beach. There are several fine restaurants around

  James Polino Compass

  267 Washington Ave Unit 5, Winthrop, MA 02152
• 

  

  /41

  $715,900 Sold Mar 30, 2026

  14 Pleasant Park Rd, Winthrop, MA 02152

  • 4 Beds
  • 1 Bath
  • 1,964 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $365/SF
  • 134 Days On Market

  Current Estimated Value $709,842

  Last Listing Agent Regina Paratore RE/MAX 360

  14 Pleasant Park Rd, Winthrop, MA 02152
• 

  

  /23

  Est $513,062 Not Listed For Sale

  3 Seal Harbor Rd Unit 234, Winthrop, MA 02152

  • 1 Bed
  • 1 Bath
  • 890 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 234, Winthrop, MA 02152

  Last Sold Summary

  • 2% Below List Price
  • $587/SF
  • 63 Days On Market

  • Last Sold Price $522,500
  • Apr 18, 2025

  Last Listing Agent Nicole Bettano Lantern Residential
• 

  

  /30

  $639,000

  • 2 Beds
  • 1 Bath
  • 1,213 Sq Ft

  51 Harbor View Ave Unit 1, Winthrop, MA 02152

  Harborview Condo with Sweeping ViewsWelcome to The Condos at 51 Harborview. This beautifully renovated condo is perched high on the hill with stunning harbor and city skyline views. Unit 1 features two bedrooms and one bath, including a spacious primary with walk-in closet, and a brand-new kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl

  Susan Doig Donnelly + Co.

  51 Harbor View Ave Unit 1, Winthrop, MA 02152
• 

  

  /37

  $2,500 - $3,200

  Total Monthly Price

  • 1 - 2 Beds
  • 2 Baths
  • 524 Sq Ft
  • Condo for Rent

  5 Fremont St, Winthrop, MA 02152

  5 Fremont St, Winthrop, MA 02152
• 

  

  /29

  $632,000 Sold Dec 01, 2025

  55 Johnson Ave Unit 1, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,614 Sq Ft
  • Built 1900

  Last Sold Summary

  • $392/SF
  • 9 Days On Market

  Current Estimated Value $611,218

  Last Listing Agent Nick Murphy Serhant

  55 Johnson Ave Unit 1, Winthrop, MA 02152
• 

  

  /40

  Est $635,772 Not Listed For Sale

  3 Seal Harbor Rd Unit 232, Winthrop, MA 02152

  • 1 Bed
  • 2 Baths
  • 1,263 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 232, Winthrop, MA 02152

  Last Sold Summary

  • 2% Below List Price
  • $515/SF
  • 12 Days On Market

  • Last Sold Price $650,000
  • Dec 23, 2024

  Last Listing Agent Nicole Bettano Lantern Residential
• 

  

  /23

  $424,000

  • 2 Beds
  • 1 Bath
  • 669 Sq Ft

  53 Trident Ave Unit 202, Winthrop, MA 02152

  Imagine starting your day with a walk along the beach. You could do that if you buy this terrific 2 bedroom corner unit. Featuring an open concept floor plan, this unit has no wasted space as well as terrific storage. The kitchen features custom cabinetry, granite counters, high end stainless steel appliances including a whisper quiet Bosch dishwasher and an island with ample storage below. The

  Andrew McKinney Donnelly + Co.

  53 Trident Ave Unit 202, Winthrop, MA 02152
• 

  

  /12

  $2,500 Per Month

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

  56 Park Ave Unit 2, Winthrop, MA 02152

  Spacious and bright 2 bedroom with bonus room/office, private front porch and rear enclosed porch just a block away from the Ocean. This building has a shared yard and coin op laundry in basement. Versatile space you can design your own layout!

  Josephine Marino DiMarzo Lyv Realty

  56 Park Ave Unit 2, Winthrop, MA 02152
• 

  

  /21

  $479,000 Sold Dec 15, 2025

  249 Winthrop Shore Dr Unit 6, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 1,415 Sq Ft
  • Built 1900

  Last Sold Summary

  • $339/SF
  • 19 Days On Market

  Current Estimated Value $477,699

  Last Listing Agent Kathleen Dailey Compass

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

  

  /28

  Est $534,507 Not Listed For Sale

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152

  • 1 Bed
  • 1.5 Baths
  • 1,033 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152

  Last Sold Summary

  • 9% Above List Price
  • $474/SF
  • 45 Days On Market

  • Last Sold Price $490,000
  • Jun 23, 2023

  Last Listing Agent Lisa Licata-Schepici L.L.S. Realty LLC
• 

  

  /13

  $235,000

  • 1 Bed
  • 1 Bath
  • 350 Sq Ft

  229 Washington Ave Unit 3A, Winthrop, MA 02152

  Enjoy coastal living in this charming waterfront condominium in Winthrop, offering the perfect balance of convenience and seaside lifestyle. Located just minutes from Boston Logan Airport and with easy access to public transportation including nearby bus routes, the Orient Heights MBTA station, and the East Boston ferry, this home is ideal for commuters seeking quick access to Boston while

  Vivian DaSilva-Braga REMAX Executive Realty

  229 Washington Ave Unit 3A, Winthrop, MA 02152
• 

  /2

  $3,150 - $3,450

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Condo for Rent

  411 Shirley St, Winthrop, MA 02152

  This property at 411 Shirley St offers a lovely 1300 square foot apartment to call home. It includes essential amenities such as air conditioning, a dishwasher, and laundry hook ups. The living room provides ample space for relaxation and entertainment, while the bedrooms are designed to accommodate various layouts. The bathroom is equipped with standard fixtures for convenience. The property

  411 Shirley St, Winthrop, MA 02152
• 

  

  /42

  $543,000 Sold Mar 02, 2026

  1 Seal Harbor Rd Unit 415, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,203 Sq Ft
  • Built 1983

  Last Sold Summary

  • 1% Below List Price
  • $451/SF
  • 24 Days On Market

  Current Estimated Value $552,267

  Last Listing Agent Camilo & Co. Group Realty One Group Nest

  1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
• 

  

  /42

  Est $966,829 Not Listed For Sale

  218 Cliff Ave, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,343 Sq Ft
  • Built 1890

  218 Cliff Ave, Winthrop, MA 02152

  Last Sold Summary

  • 5% Above List Price
  • $393/SF
  • 17 Days On Market

  • Last Sold Price $921,000
  • May 03, 2023

  Last Listing Agent Christine D'Ambrosio Lantern Residential
• 

  

  /28

  $765,000

  • 3 Beds
  • 1.5 Baths
  • 1,588 Sq Ft

  15 Wave Way, Winthrop, MA 02152

  Come experience coastal living at its finest in vibrant Winthrop—just minutes from Boston! This seaside single-family home is ideally located just steps from picturesque Winthrop Beach & has been thoughtfully updated for modern living. At the heart of the home is a stunning white quartz kitchen, fully equipped with SS appliances, vent hood, & rich espresso hardwood floors, creating a clean,

  Atiyeh Cassidy Blue Sky Realty

  15 Wave Way, Winthrop, MA 02152
• 

  

  /32

  $3,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Apartment for Rent

  15 Putnam Place, Winthrop, MA 02152

  Available now for rent! Renovated and Spacious 3 Bed / 2 Bath Townhouse located near Downtown Winthrop on a quiet, secluded residential street. This 1700+ sqft home features 2 off-street parking spaces, private outdoor patio/deck and a flexible, comfortable living space. Step into the main level to entertain or relax in your open living/dining rooms with hardwood floors along with a tiled, modern

  Brian Rivas Carlton's Wharf & Co.

  15 Putnam Place, Winthrop, MA 02152
• 

  

  /30

  $920,000 Sold Sep 15, 2025

  94 Circuit Rd, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft
  • Built 1925

  Last Sold Summary

  • 2% Above List Price
  • $502/SF
  • 40 Days On Market

  Current Estimated Value $901,707

  Last Listing Agent Leighann Eruzione Lantern Residential

  94 Circuit Rd, Winthrop, MA 02152
• 

  

  /29

  Est $512,774 Not Listed For Sale

  173 Grovers Ave Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1904

  173 Grovers Ave Unit 2, Winthrop, MA 02152

  Last Sold Summary

  • 5% Above List Price
  • $408/SF
  • 78 Days On Market

  • Last Sold Price $490,000
  • Nov 01, 2024

  Last Listing Agent Steve Binder Binder Residential
• 

  

  /40

  $1,180,000

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

  47 Bellevue Ave, Winthrop, MA 02152

  Introducing coastal living in this luxurious two-family home set on one of Winthrop’s most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat.

  Jessica Pumphret Blue Sky Realty

  47 Bellevue Ave, Winthrop, MA 02152
• 

  /2

  $3,150 - $3,450

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Condo for Rent

  411 Shirley St, Winthrop, MA 02152

  This property at 411 Shirley St offers a lovely 1300 square foot apartment to call home. It includes essential amenities such as air conditioning, a dishwasher, and laundry hook ups. The living room provides ample space for relaxation and entertainment, while the bedrooms are designed to accommodate various layouts. The bathroom is equipped with standard fixtures for convenience. The property

  411 Shirley St, Winthrop, MA 02152
• 

  

  /27

  $720,000 Sold Aug 29, 2025

  12 Park Ave, Winthrop, MA 02152

  • 3 Beds
  • 1.5 Baths
  • 1,172 Sq Ft
  • Built 1890

  Last Sold Summary

  • 3% Above List Price
  • $614/SF
  • 14 Days On Market

  Current Estimated Value $698,936

  Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

  12 Park Ave, Winthrop, MA 02152
• 

  

  /42

  Est $995,834 Not Listed For Sale

  36 Floyd St, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,211 Sq Ft
  • Built 1925

  36 Floyd St, Winthrop, MA 02152

  Last Sold Summary

  • 3% Below List Price
  • $464/SF
  • 4 Days On Market

  • Last Sold Price $1,025,000
  • Feb 08, 2024

  Last Listing Agent The Reference Group Reference Real Estate
• 

  

  /14

  $629,000

  • 2 Beds
  • 2 Baths
  • 985 Sq Ft

  10 Somerset Ave Unit 406, Winthrop, MA 02152

  Welcome to Unit 406 at The Somerset—Winthrop’s premier boutique condo community, where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space, complemented by quartz countertops, stainless steel appliances, central A/C, and stylish finishes

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 406, Winthrop, MA 02152
• 

  

  /19

  $2,700 Per Month

  • 2 Beds
  • 1 Bath
  • 1,142 Sq Ft
  • Apartment for Rent

  19 Pearl Ave Unit 19, Winthrop, MA 02152

  Beautifully renovated and perfectly timed for summer, this inviting two bedroom apartment offers the ideal opportunity to enjoy life in Winthrop! This spacious second floor unit features a stunning modern kitchen fully equipped with gas cooking, ss appliances, quartz countertops, and peninsula for casual dining. A dedicated dining room, sun filled living room, along with a front deck, and rear

  Atiyeh Cassidy Blue Sky Realty

  19 Pearl Ave Unit 19, Winthrop, MA 02152
• 

  

  /18

  $265,000 Sold Aug 18, 2025

  265 Washington Ave Unit 2A, Winthrop, MA 02152

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

  Last Sold Summary

  • 12% Below List Price
  • $662/SF
  • 54 Days On Market

  Current Estimated Value $260,726

  Last Listing Agent Pareene Group EXIT Premier Real Estate

  265 Washington Ave Unit 2A, Winthrop, MA 02152
• 

  

  /38

  Est $997,877 Not Listed For Sale

  89 Cliff Ave, Winthrop, MA 02152

  • 5 Beds
  • 2.5 Baths
  • 2,697 Sq Ft
  • Built 1900

  89 Cliff Ave, Winthrop, MA 02152

  Last Sold Summary

  • 5% Below List Price
  • $391/SF
  • 3 Days On Market

  • Last Sold Price $1,055,000
  • Aug 19, 2024

  Last Listing Agent Erica Gore Century 21 Seaport
• 

  

  /36

  $949,900

  • 2 Beds
  • 2.5 Baths
  • 1,806 Sq Ft

  1001 Shirley St Unit 2, Winthrop, MA 02152

  Rooted in history and shaped by design, this loft at The Pearl offers something truly rare. Original hardwood floors and exposed beams, oversized windows & 15’6” ceilings create a striking sense of scale and atmosphere. The kitchen is both refined and dramatic, appointed with White shaker cabinetry, a Moonstone island, London Smoke quartzite, Bosch appliances, architectural hood, and a farmhouse

  The Legacy Group Serhant

  1001 Shirley St Unit 2, Winthrop, MA 02152
• 

  

  /37

  $2,500 - $3,200

  Total Monthly Price

  • 1 - 2 Beds
  • 2 Baths
  • 524 Sq Ft
  • Condo for Rent

  5 Fremont St, Winthrop, MA 02152

  5 Fremont St, Winthrop, MA 02152
• 

  

  /42

  $545,000 Sold Feb 13, 2026

  270 Winthrop St Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 1.5 Baths
  • 1,421 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Above List Price
  • $384/SF
  • 7 Days On Market

  Current Estimated Value $539,817

  Last Listing Agent Clara Arroyave eXp Realty

  270 Winthrop St Unit 2, Winthrop, MA 02152
• 

  

  /31

  Est $898,777 Not Listed For Sale

  92 Quincy Ave, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,497 Sq Ft
  • Built 1910

  92 Quincy Ave, Winthrop, MA 02152

  Last Sold Summary

  • 6% Above List Price
  • $338/SF
  • 13 Days On Market

  • Last Sold Price $845,000
  • Jul 24, 2024

  Last Listing Agent Leighann Eruzione Lantern Residential

Showing Results 121 - 160, Page 4 of 18