Downtown Winthrop Homes

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  /42

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 2,350 Sq Ft

  136 Pauline St, Winthrop, MA 02152

  Beautifully renovated 4-bedroom, 3.5-bath single-family home, fully gutted and updated in 2020. This turnkey property features an open floor plan with seamless flow between the spacious living room, dining area, and modern kitchen—perfect for today’s lifestyle and entertaining. The primary suite includes a walk-in closet and private en-suite bath. A finished basement (2021) provides flexible

  Anthony Carestia William Raveis R.E. & Home Services

  136 Pauline St, Winthrop, MA 02152
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  /11

  $2,400 per month

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

  26 Central St, Winthrop, MA 02152

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

  26 Central St, Winthrop, MA 02152
• 

  

  

  /23

  $738,000 Sold May 28, 2025

  • 1,887 Sq Ft
  • $391/SF
  • 17 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  15 Williams St, Winthrop, MA 02152

  This picture perfect Dutch Colonial features many classic elements without sacrificing modern conveniences. Filled with stunning details - elaborate carved newels, a mosaic fireplace, original hardwoods throughout, and ultra-convenient built-ins, this turn-of the century marvel is sure to charm you. Literal steps to both the heart of town and the beach, this immaculately maintained home offers

  Harry Silverstein Keller Williams Realty Boston Northwest

  15 Williams St, Winthrop, MA 02152
• 

  

  

  /25

  Est $464,516 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,036 Sq Ft

  49 Sagamore Ave Unit 1B, Winthrop, MA 02152

  49 Sagamore Ave Unit 1B, Winthrop, MA 02152
• 

  

  

  /30

  $588,888

  • 4 Beds
  • 1.5 Baths
  • 1,785 Sq Ft

  123 Buchanan St, Winthrop, MA 02152

  Step back in time, a stately 19th-century home ready to be restored and reimagined. This 4-bedroom, 1.5-bath is rich with character—featuring original beamed ceilings, ornamental exterior wood trim, and timeless architectural details that set the stage for a stunning transformation. Located near Winthrop Golf Club, High School, and the coastal beauty of Boston’s shoreline, this home offers a rare

  Ronda Cogliano Century 21 North East

  123 Buchanan St, Winthrop, MA 02152
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  /11

  $2,400 per month

  • 1 Bed
  • 1 Bath
  • 820 Sq Ft
  • Apartment for Rent

  554 Pleasant St Unit 2, Winthrop, MA 02152

  Direct Oceanfront Living! Enjoy front-row views of passing boats from this beautifully updated and well-maintained 1-bedroom, 1-bath apartment. The open-concept layout features hardwood floors, high ceilings, abundant natural light, and large windows showcasing stunning ocean views. Additional highlights include private in-unit laundry and one off-street parking space. Located in Winthrop, a

  Candice Hodgson Lyv Realty

  554 Pleasant St Unit 2, Winthrop, MA 02152
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  /26

  $640,000 Sold May 23, 2025

  • 1,050 Sq Ft
  • $610/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  83 Chester Ave, Winthrop, MA 02152

  Centrally located on a corner is this 3+ bedroom single family. It's not a huge home but it's PRICED RIGHT & it has some great updates starting w/the freshly painted interior, gas FHW heating system, some replacement windows & vinyl cedar impression shingles. The eat in kitchen has s/s appliances & access to a rear porch. The seller has added loads of built in storage throughout especially in

  Mary Ann Cash Charlesgate Realty Group, llc

  83 Chester Ave, Winthrop, MA 02152
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  /7

  Est $744,451 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,563 Sq Ft

  16 Sagamore Ave, Winthrop, MA 02152

  16 Sagamore Ave, Winthrop, MA 02152
• 

  

  /28

  $735,000 Open Thu 5PM - 6PM

  • 3 Beds
  • 1 Bath
  • 1,269 Sq Ft

  19 Banks St, Winthrop, MA 02152

  Do you ever step into a home and feel an instant calm—as if it’s been waiting just for you? 19 Banks Street wraps you in warmth from the moment you enter. The sunporch glows with light from three walls of windows and leads to a living room with gleaming hardwood floors and a fireplace. This classic 3-bed, 1-bath Colonial is filled with charm—paned windows, graceful flow—and updated for comfort

  Susan Doig Charlesgate Realty Group, llc

  19 Banks St, Winthrop, MA 02152
• 

  

  /21

  $3,200 per month

  • 2 Beds
  • 2 Baths
  • 969 Sq Ft
  • Condo for Rent

  35 Somerset Ave Unit 5A, Winthrop, MA 02152

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

  35 Somerset Ave Unit 5A, Winthrop, MA 02152
• 

  

  /37

  $500,000 Sold May 19, 2025

  • 1,284 Sq Ft
  • $389/SF
  • 24 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1900

  270 Winthrop St Unit 1, Winthrop, MA 02152

  Welcome to The Grand Victorian Condominiums. Step into the elegance of this 2-bedroom, 2-bath home nestled in a beautiful late 19th-century Victorian building. This residence exudes timeless character with its soaring high ceilings and exquisite woodwork throughout. The spacious living areas are enhanced by gorgeous fireplace mantels, showcasing the fine craftsmanship that defines this historical

  Cathie Curran Charlesgate Realty Group, llc

  270 Winthrop St Unit 1, Winthrop, MA 02152
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  /42

  Est $630,899 Not Listed For Sale

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

  465 Winthrop St, Winthrop, MA 02152

  465 Winthrop St, Winthrop, MA 02152
• 

  

  /30

  $729,000

  • 3 Beds
  • 1 Bath
  • 1,548 Sq Ft

  60 Waldemar Ave, Winthrop, MA 02152

  Located in one of Winthrop's most desirable Center locations, this well maintained 7 room, 3 bedroom single says welcome home! The kitchen has been updated with granite counters and stainless steel appliances and the bayed living and dining rooms with high ceilings are elegant and very inviting. The full bath has a jetted tub and separate shower! There are beautiful wood floors throughout. Love

  James Polino Compass

  60 Waldemar Ave, Winthrop, MA 02152
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  /26

  $2,900 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  370 Main St Unit 2, Winthrop, MA 02152

  Welcome to 370 Main St #2 in beautiful Winthrop, MA—a fully furnished 2-bedroom, 1-bath apartment that’s ready for immediate move-in. Just bring your bags and start living comfortably in this well-kept second-floor unit. With everything you need already in place, it’s perfect for anyone looking for a convenient, no-fuss rental. The apartment features large windows throughout, allowing for great

  Antonio Ferreira Zander Realty Group

  370 Main St Unit 2, Winthrop, MA 02152
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  /38

  $620,000 Sold May 19, 2025

  • 1,684 Sq Ft
  • $368/SF
  • 15 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1860

  240 Bowdoin St, Winthrop, MA 02152

  Welcome to an incredible opportunity to own an affordable single-family home in the desirable Winthrop by the Sea! This delightful property offers 4 bedrooms and 1.5 baths, with a spacious, open kitchen and a versatile downstairs layout that can easily be updated to your preferences. Recent updates have enhanced both the structure and functionality of the home, including improvements to the

  Jenny Golic Lantern Residential

  240 Bowdoin St, Winthrop, MA 02152
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  /17

  Est $594,626 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 984 Sq Ft

  500 Winthrop St, Winthrop, MA 02152

  500 Winthrop St, Winthrop, MA 02152
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  /14

  $624,900

  • 3 Beds
  • 1 Bath
  • 1,878 Sq Ft

  136 Locust Way, Winthrop, MA 02152

  Well maintained 3 bedroom Colonial just moments from the beach. Large open rooms with lots of natural light. Lots of cabinet space in the super functional kitchen. 1st floor laundry hookups for convenience. 3 full sized bedrooms. Great yard. Nice wrap around porch to enjoy the summer nights. Seller willing to buy down the mortgage rate on this home. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

  Tyler Scaglione Cameron Real Estate Group

  136 Locust Way, Winthrop, MA 02152
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  /37

  $2,500 per month

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

  5 Fremont St, Winthrop, MA 02152

  5 Fremont St, Winthrop, MA 02152
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  /30

  $765,000 Sold May 16, 2025

  • 1,698 Sq Ft
  • $451/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1910

  127 Bowdoin St, Winthrop, MA 02152

  This charming and meticulously maintained single-family home offers 3 spacious bedrooms and 2 full bathrooms, perfect for comfortable living and entertaining. Gleaming hardwood floors flow throughout the bright, open layout, creating a warm and inviting atmosphere. Enjoy year-round comfort with first-floor air conditioning, efficient gas heating, and a cozy fireplace. A versatile sunroom provides

  Leighann Eruzione Lantern Residential

  127 Bowdoin St, Winthrop, MA 02152
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  /30

  Est $785,523 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,079 Sq Ft

  157 Morton St, Winthrop, MA 02152

  157 Morton St, Winthrop, MA 02152
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  /29

  $1,100,000

  • 4 Beds
  • 2 Baths
  • 2,366 Sq Ft

  80 Shirley St, Winthrop, MA 02152

  Gorgeous farmhouse revival!!! Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge

  Nick Burnes Red Tree Real Estate

  80 Shirley St, Winthrop, MA 02152
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  /16

  $3,600 per month

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

  49 Bates Ave Unit 51, Winthrop, MA 02152

  Price drop down without furnished.Luxury apartment for rent in Winthrop, MA. This spacious unit features three bedrooms and two full bathrooms, and boasts hardwood floors throughout the entire home. The apartment is equipped with gas heating, ensuring warmth and comfort during the colder months.The entire third floor is dedicated to the main bedroom, providing privacy and ample space, and adorned

  David Li eXp Realty

  49 Bates Ave Unit 51, Winthrop, MA 02152
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  /42

  $785,000 Sold May 16, 2025

  • 1,680 Sq Ft
  • $467/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  95 Summit Ave Unit 4, Winthrop, MA 02152

  Perched atop Floyd’s Hill overlooking the Atlantic Ocean, your new home offers the lifestyle you crave. Start your day with a run along Winthrop Beach or open up the wall of glass to your large private deck for morning yoga and coffee sunrises, mesmerized by the ocean and end-of-day cocktail sunsets overlooking the city from your rooftop with a 360 panorama. Just minutes from Boston, this large

  Joseph Schutt Unit Realty Group, LLC

  95 Summit Ave Unit 4, Winthrop, MA 02152
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  /21

  Est $767,581 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,788 Sq Ft

  58 Banks St, Winthrop, MA 02152

  58 Banks St, Winthrop, MA 02152
• 

  

  /29

  $449,900

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft

  80 Shirley St Unit 1, Winthrop, MA 02152

  Gorgeous farmhouse revival! Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge

  Nick Burnes Red Tree Real Estate

  80 Shirley St Unit 1, Winthrop, MA 02152
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  /37

  $3,200 per month

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

  5 Fremont St, Winthrop, MA 02152

  5 Fremont St, Winthrop, MA 02152
• 

  

  /23

  $945,000 Sold May 16, 2025

  • 3,620 Sq Ft
  • $261/SF
  • 8 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1923

  71 Paine St, Winthrop, MA 02152

  Welcome to 71 Paine Street—an oversized 2-family home sitting proudly on a corner lot at Wilshire & Paine. This property has everything you need, whether you're looking for a fantastic investment opportunity or the perfect owner-occupied setup with rental income! Both units feature private decks, off-street parking, separate heating systems, and divided basement space for storage &

  The Reference Group Reference Real Estate

  71 Paine St, Winthrop, MA 02152
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  /28

  Est $576,167 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  26 Amelia Ave, Winthrop, MA 02152

  26 Amelia Ave, Winthrop, MA 02152
• 

  

  /37

  $995,500

  • 5 Beds
  • 3 Baths
  • 3,272 Sq Ft

  115 Almont St, Winthrop, MA 02152

  115 Almont, where coastal vibes meet versatile living areas to offer something for everyone. Don't miss your chance to see this expansive 5 bedroom 3 bathroom colonial just minutes to Winthrop Beach, fantastic restaurants, schools & more. Upon entry, you are greeted with a beautiful living room with working fireplace, updated eat-in kitchen, full bathroom and first floor bedroom. This setup would

  Christine Goldstein Lyv Realty

  115 Almont St, Winthrop, MA 02152
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  /42

  $3,150 per month

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

  100 Summit Ave Unit 2, Winthrop, MA 02152

  Brittney Lamme D & R Realty

  100 Summit Ave Unit 2, Winthrop, MA 02152
• 

  

  /22

  $780,000 Sold May 13, 2025

  • 1,490 Sq Ft
  • $523/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  152 Lincoln St, Winthrop, MA 02152

  Welcome to 152 Lincoln Street, where modern comfort meets coastal town charm! This beautifully updated 3-bedroom, 1.5-bath single-family home offers everything you need for easy living. Step inside to find a stylish, sunlit interior with stainless steel appliances, an open and inviting layout, and a finished basement—perfect for a home office, playroom, or additional living space. Stay

  The Reference Group Reference Real Estate

  152 Lincoln St, Winthrop, MA 02152
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  /24

  Est $495,416 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,095 Sq Ft

  93 Shirley St Unit 2, Winthrop, MA 02152

  93 Shirley St Unit 2, Winthrop, MA 02152
• 

  

  /41

  $849,900 Pending

  • 5 Beds
  • 2 Baths
  • 2,494 Sq Ft

  26 Enfield Rd, Winthrop, MA 02152

  Charming two-family in desirable area of Winthrop. Steps away from Ingleside Park's playground, roller hockey court and baseball field. The restaurants of Winthrop's center are close proximity as well. Great opportunity on one of the nicest streets in Winthrop.

  Nicholas Martino Noddle Island Real Estate

  26 Enfield Rd, Winthrop, MA 02152
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  /29

  $900,000 Sold May 09, 2025

  • 2,988 Sq Ft
  • $301/SF
  • 7 Days On Market

  • 8 Beds
  • 3 Baths
  • Built 1957

  84 Banks St, Winthrop, MA 02152

  Rare opportunity to own a double lot two-family home with expansion possibilities for a third unit. This well-maintained property offers stunning views of Belle Isle marsh and direct gated access to scenic walking trails and tranquil vistas. The fenced-in backyard is ready to enjoy with mature fruit trees, flowering shrubs, a deck and koi pond that await your fish. The main unit showcases a

  Erica Gore Century 21 Seaport

  84 Banks St, Winthrop, MA 02152
• 

  

  /29

  Est $489,764 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  93 Shirley St Unit 1, Winthrop, MA 02152

  93 Shirley St Unit 1, Winthrop, MA 02152
• 

  

  /32

  $594,900 Pending

  • 2 Beds
  • 2 Baths
  • 985 Sq Ft

  10 Somerset Ave Unit 206, Winthrop, MA 02152

  Welcome to The Somerset—Winthrop’s newest boutique condo development, where coastal charm meets modern luxury. This spacious 2-bedroom, 2-bath home is designed for effortless living, featuring a sun-drenched open layout, private balcony, and oversized walk-in wardrobes in both bedrooms. Enjoy a sleek kitchen with stainless steel appliances, quartz countertops, and soft-close cabinetry, flowing

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 206, Winthrop, MA 02152
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  /29

  $635,000 Sold May 09, 2025

  • 968 Sq Ft
  • $656/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1880

  31 River Rd, Winthrop, MA 02152

  Charming 2-bedroom, 1-bath home in the sought-after Cottage Park area of Winthrop! Cozy new front porch leads you into an inviting living room w/ gleaming HW floors & plenty of natural light. The dining room, featuring a custom built-in china cabinet w/ 3 drawers for add'l storage, flows seamlessly into the kitchen w/ ample cabinet space, tile flooring & a breakfast bar. Enjoy new SS smart

  Paul Cervone Lamacchia Realty, Inc.

  31 River Rd, Winthrop, MA 02152
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  /37

  Est $742,389 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,564 Sq Ft

  105 Almont St, Winthrop, MA 02152

  105 Almont St, Winthrop, MA 02152
• 

  

  /23

  $555,000 Pending

  • 1 Bed
  • 1 Bath
  • 684 Sq Ft

  10 Somerset Ave Unit 401, Winthrop, MA 02152

  The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 401, Winthrop, MA 02152
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  /25

  $490,000 Sold May 07, 2025

  • 1,270 Sq Ft
  • $386/SF
  • 74 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1925

  111 Locust St Unit 2, Winthrop, MA 02152

  Back on market due to buyer financing. Charming light filled 3 bedroom condo steps to Winthrop Beach offers coastal living at its finest. Well thought-out layout maximizes comfort and functionality. The open living/dining rooms are bright and inviting with ample space for relaxing or entertaining. Each of the 3 bedrooms are generously sized perfect for family, guests or a home office. Large

  Christine D'Ambrosio Lantern Residential

  111 Locust St Unit 2, Winthrop, MA 02152

Showing Results 41 - 80, Page 2 of 18