Recently Sold Homes near Winthrop High School

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  /26

  $949,000 Sold Oct 03, 2025

  • 2,237 Sq Ft
  • $424/SF
  • 27 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1887

  26 Sargent St, Winthrop, MA 02152

  Welcome to 26 Sargent Street, a beautifully restored and thoughtfully upgraded single-family residence nestled on one of Winthrop’s most picturesque, tree-lined streets. This expansive 5+ bedroom, 2.5 bath home masterfully blends timeless architectural charm with modern luxury, offering refined living spaces and every contemporary convenience. From the moment you enter, you’ll be captivated by

  Mike Wetherbee Cameron Real Estate Group

  26 Sargent St, Winthrop, MA 02152
• 

  Explore Winthrop High School

• 

  

  

  /19

  $1,590,000 Sold Oct 02, 2025

  • 2,455 Sq Ft
  • $648/SF
  • 9 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1950

  23 Nahant Ave, Winthrop, MA 02152

  Dramatic oceanfront retreat! This spectacular, fully renovated 2-bed, 2-bath ranch offers panoramic water views from every room. Vaulted ceilings enhance the open-concept living room, leading to a chef’s kitchen with custom cabinetry and stone counters. Relax year-round in the sun-drenched 4-season sunroom or entertain on the ocean-facing lawn. Finished basement offers flexible living space for a

  Souzan Davood Coldwell Banker Realty - Newton

  23 Nahant Ave, Winthrop, MA 02152
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  /42

  $1,270,000 Sold Sep 30, 2025

  • 2,775 Sq Ft
  • $458/SF
  • 6 Days On Market

  • 9 Beds
  • 3 Baths
  • Built 1900

  19 Jefferson St, Winthrop, MA 02152

  OFFER DEADLINE 9/2 3PM Rare find 3family with separate utilities, off street pkg, btfl fence enclosed yard, porches w/views and many updates. Unit 1 was a 3 bed but now has laundry in unit, a huge livingroom/diningroom, bath with jacuzzi tub, central air and large eat in kitchen with oak cabinets and ample counter space perfect for owner occupied. Unit 2 is beautifully renovated with 5rms/3beds

  Lisa Licata-Schepici L.L.S. Realty LLC

  19 Jefferson St, Winthrop, MA 02152
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  /39

  $650,000 Sold Sep 30, 2025

  • 1,124 Sq Ft
  • $578/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  One Seal Harbor Rd Unit 604, Winthrop, MA 02152

  LUXURY OCEAN FRONT CONDO at SEAL HARBOR with direct ocean views! Enjoy coffee in the morning or candlelight dinner on the balcony while listening to ocean waves & boats on water. Beautifully renovated including bathrooms, stainless steel appliances, lights, door handles, freshly painted, outlets, etc. Open concept floor plan to enjoy the delightful views from all the rooms. Front to back dining

  Marina Tramontozzi True North Realty

  One Seal Harbor Rd Unit 604, Winthrop, MA 02152
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  /24

  $860,000 Sold Sep 30, 2025

  • 2,308 Sq Ft
  • $373/SF
  • 12 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1900

  77 Cottage Ave, Winthrop, MA 02152

  Step inside this delightful newly renovated 2 family gem, just a short stroll from the beach, park, Yacht Club, & vibrant collection of local restaurants! Up on Cottage Hill & out of the flood zone, it’s easy to feel like you’re living in 1 beautiful home with the added bonus of a private lower-level. The main home is a light filled living area with gleaming hardwood floors & spacious rooms for

  Atiyeh Cassidy Blue Sky Realty

  77 Cottage Ave, Winthrop, MA 02152
• 

  

  /37

  $975,000 Sold Sep 30, 2025

  • 3,970 Sq Ft
  • $246/SF
  • 5 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1910

  175 Somerset Ave, Winthrop, MA 02152

  Large two-family home in a highly sought after area in Winthrop on a large lot of land (7500sq feet). The property includes two spacious units and boasts a large backyard. The first-floor unit is a three-bedroom one bath, and the top unit is two bed-room one full bath and an unfinished master bath both units have lots of natural light. Second floor unit also has the added potential of a large

  Justin Martino Noddle Island Real Estate

  175 Somerset Ave, Winthrop, MA 02152
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  /30

  $715,000 Sold Sep 30, 2025

  • 1,269 Sq Ft
  • $563/SF
  • 58 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1936

  19 Banks St, Winthrop, MA 02152

  Do you ever walk into a home and instantly feel at ease—like it was meant for you? 19 Banks Street does just that. From the sun-splashed porch with three walls of windows to the inviting living room with hardwood floors and a fireplace, this classic 3-bed, 1-bath Colonial blends charm and comfort. Enjoy paned windows, an easy flow, and modern updates like a new roof, high-efficiency gas heat, and

  Susan Doig Charlesgate Realty Group, llc

  19 Banks St, Winthrop, MA 02152
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  /25

  $880,000 Sold Sep 26, 2025

  • 2,764 Sq Ft
  • $318/SF
  • 6 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1979

  17 Buckthorn Terrace, Winthrop, MA 02152

  Welcome to your dream home nestled on a quiet side street in the picturesque seaside town of Winthrop. This stunning 4 bedroom, 3.5 bathroom property blends timeless elegance with modern luxury, offering an abundance of space and upscale amenities just minutes from Boston. Step inside to discover a beautifully designed interior featuring elegant finishes all around, an exquisite almost seashell

  Richard Harkins EWK Realty

  17 Buckthorn Terrace, Winthrop, MA 02152
• 

  

  /31

  $575,000 Sold Sep 26, 2025

  • 1,785 Sq Ft
  • $322/SF
  • 63 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1884

  123 Buchanan St, Winthrop, MA 02152

  Step back in time, a stately 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 opportunity

  Ronda Cogliano Century 21 North East

  123 Buchanan St, Winthrop, MA 02152
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  /34

  $722,000 Sold Sep 25, 2025

  • 1,776 Sq Ft
  • $407/SF
  • 12 Days On Market

  • 5 Beds
  • 1.5 Baths
  • Built 1910

  41 Centre St, Winthrop, MA 02152

  Discover this well-loved generational home where character greets you at every turn. Sunlight pours through a stunning stained-glass window in the foyer, hardwood floors flow throughout, and every room tells its own story. The spacious eat-in kitchen is perfect for gatherings, while the large living areas offer space to entertain with ease. A full bath on the first floor adds convenience, and

  Leighann Eruzione Lantern Residential

  41 Centre St, Winthrop, MA 02152
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  /26

  $490,000 Sold Sep 22, 2025

  • 865 Sq Ft
  • $566/SF
  • 117 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  600 Shirley St Unit 16, Winthrop, MA 02152

  Always wanted to live across from the beach? This might be the place for you! Enjoy breathtaking water and Boston skyline views from this beautifully renovated 2-bed, 2-bath condo at the former Historic Crystal Cove Hotel. Offering first-floor convenience with a private entrance and two deeded parking spaces right outside your door, this home lives like a private residence. The open layout

  Elizabeth Crowley William Raveis R.E. & Home Services

  600 Shirley St Unit 16, Winthrop, MA 02152
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  /41

  $1,175,000 Sold Sep 17, 2025

  • 2,214 Sq Ft
  • $531/SF
  • 15 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2009

  72 Sewall Ave, Winthrop, MA 02152

  Highly desirable location this home is only 16 years old built over its original foundation. this 4-bed, 3.5-bath home spans three levels in Winthrop’s Highlands. The first floor offers an open layout ideal for entertaining, with a spacious kitchen featuring white cabinets and updated countertops flowing into the living and dining rooms. French doors lead to a deck and patio overlooking a large,

  Elizabeth Ferrara Cottage Hill Real Estate

  72 Sewall Ave, Winthrop, MA 02152
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  /23

  $355,000 Sold Sep 16, 2025

  • 772 Sq Ft
  • $460/SF
  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1971

  500 Governors Dr Unit 9, Winthrop, MA 02152

  Welcome to 500 Governors Drive Unit 9, a spacious and well-maintained 3-bedroom, first-floor condo located in the beautiful coastal town of Winthrop. This unit features a bright and airy open-concept living and dining area, perfect for both relaxing and entertaining. Vinyl flooring runs throughout the entire home, offering a sleek, low-maintenance finish. Set within a well-managed association,

  Juan Cano Broad Sound Real Estate, LLC

  500 Governors Dr Unit 9, Winthrop, MA 02152
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  /25

  $670,000 Sold Sep 16, 2025

  • 1,413 Sq Ft
  • $474/SF
  • 76 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1884

  162 Shirley St Unit 164, Winthrop, MA 02152

  Don’t miss this rare opportunity to own a well-priced single-family home in the heart of Winthrop by the Sea, under a 5-minute walk to both the beach and Winthrop Middle/High School. This charming home features 3 bedrooms and 2 full baths. The second floor also offers room for expansion to add a 4th bedroom, sellers are including the architectural plans. The main level boasts new appliances,

  Jenny Golic Lantern Residential

  162 Shirley St Unit 164, Winthrop, MA 02152
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  /30

  $920,000 Sold Sep 15, 2025

  • 1,831 Sq Ft
  • $502/SF
  • 40 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1925

  94 Circuit Rd, Winthrop, MA 02152

  Step inside this farmhouse-style gem and feel right at home. The first floor offers a spacious layout featuring a cozy eat-in kitchen with stainless steel appliances, a formal dining room, and a full bath with direct access to the backyard, perfect for easy pool days. Hardwood floors flow throughout, adding warmth and charm to every room. Character shines at every turn with thoughtful details

  Leighann Eruzione Lantern Residential

  94 Circuit Rd, Winthrop, MA 02152
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  /42

  $1,050,000 Sold Sep 12, 2025

  • 2,144 Sq Ft
  • $490/SF
  • 7 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1880

  29 Dolphin Ave, Winthrop, MA 02152

  Gorgeous turnkey 2 family home, steps from the beach, could be your dream home or an excellent investment! Both units feature spacious living rooms, three bedrooms each, eat in kitchens two full bathrooms and in-unit laundry! Unit 1 has a second bathroom ensuite. The units have been updated within the last two years with new flooring, new stainless appliances, upgraded cabinetry, and the entire

  Sara Hrono Century 21 North East

  29 Dolphin Ave, Winthrop, MA 02152
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  /37

  $960,000 Sold Sep 11, 2025

  • 3,272 Sq Ft
  • $293/SF
  • 84 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1967

  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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  /31

  $390,000 Sold Sep 10, 2025

  • 679 Sq Ft
  • $574/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1902

  23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  Beautifully Renovated Condo with Water Views in Winthrop! This thoughtfully updated condo offers modern living on coveted Winthrop Shore Drive, directly facing Winthrop Beach. Featuring a stylish kitchen and open-concept layout, this bright and inviting unit is perfect as a first home, second home, or investment property. Enjoy peaceful water views from the living room or sip your morning

  Mariel Yovino Compass

  23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /14

  $625,000 Sold Sep 09, 2025

  • 1,878 Sq Ft
  • $333/SF
  • 71 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  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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  /17

  $925,000 Sold Sep 08, 2025

  • 2,341 Sq Ft
  • $395/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  31 Lincoln St, Winthrop, MA 02152

  Historic charm and modern comfort unite in this warm, inviting 3-bedroom, 2.5-bath home in the Ingleside Park neighborhood. Step inside to find stunning original woodwork, a cozy pellet stove perfect for cool summer nights, fresh paint throughout and the High-velocity AC will keep you cool all summer. 31 Lincoln has tons of upgrades...Brand new copper water line, new PVC drain to the street, new

  The Reference Group Reference Real Estate

  31 Lincoln St, 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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  /40

  $735,000 Sold Sep 05, 2025

  • 2,327 Sq Ft
  • $316/SF
  • 10 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1920

  4 Circuit Rd, Winthrop, MA 02152

  Prime corner lot in one of Winthrop’s most desirable neighborhoods! This home has great bones and is ready for new owners to make it their own. With an ideal layout, the second floor offers the perfect space for a primary suite with walk-in closet and full bath. The first floor features a spacious living room, with the opportunity to open up the kitchen and dining area for a large island and

  Elizabeth Ferrara Cottage Hill Real Estate

  4 Circuit Rd, 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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  /32

  $462,000 Sold Sep 03, 2025

  • 1,165 Sq Ft
  • $397/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  94 Lincoln St Unit 2, Winthrop, MA 02152

  This charming, move-in-ready 2-bed, 1-bath condo in a gorgeous brownstone building offers historic character and modern convenience just minutes from downtown Boston! Beautiful original hardwood floors and bay window add warmth and timeless appeal. Both bedrooms are generously sized and filled with natural light. The second bedroom has a walk-in closet. The spacious, eat-in kitchen features tile

  David Ladner RE/MAX Harmony

  94 Lincoln St Unit 2, Winthrop, MA 02152
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  /29

  $735,000 Sold Sep 02, 2025

  • 1,165 Sq Ft
  • $631/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1900

  148 Winthrop Shore Dr Unit 4, Winthrop, MA 02152

  Experience the ultimate home getaway in this beautifully renovated 2 bed, 2 bath condo with stunning, unobstructed ocean views and deeded parking in Winthrop's growing community! Enjoy sunsets and sea breezes from your private balcony. Inside, 10+ ft ceilings, white oak floors, central AC, custom blinds, and smart home features offer lots of comfort and style. The chef’s kitchen boasts a

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  148 Winthrop Shore Dr Unit 4, 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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  /41

  $830,000 Sold Aug 30, 2025

  • 2,958 Sq Ft
  • $281/SF
  • 48 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1920

  37-39 Hutchinson St, Winthrop, MA 02152

  Endless Potential in Prime Seaside Location – 02152 Welcome to this oversized two-family home located in the highly desirable seaside community of Winthrop, 02152. Perfectly situated on a generous lot, this property offers a rare opportunity for investors, multi-generational living, or owner-occupants looking to customize and create value.Each unit features spacious layouts with room to grow, and

  Nicole Bettano Lantern Residential

  37-39 Hutchinson St, Winthrop, MA 02152
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  /27

  $720,000 Sold Aug 29, 2025

  • 1,172 Sq Ft
  • $614/SF
  • 14 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1890

  12 Park Ave, Winthrop, MA 02152

  INTRODUCING 12 PARK AVENUE...This meticulous single family home features 6+ rooms of bright and comfortable living spaces, a private fenced in yard and off street parking. An enclosed sunporch welcomes you to the first floor which has hardwood floors, an open floor plan, a fully applianced kitchen and convenient 1/2 bath. The second floor has three bedrooms with custom built closets and a full

  Mary Ann Cash Charlesgate Realty Group, llc

  12 Park Ave, Winthrop, MA 02152
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  /29

  $440,000 Sold Aug 29, 2025

  • 812 Sq Ft
  • $542/SF
  • 29 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  5 Pearl Ave Unit 2, Winthrop, MA 02152

  Enjoy coastal living just one block from the ocean in this beautifully updated 2-bedroom, 1-bath home nestled in the heart of Winthrop. Step inside to a bright, airy layout featuring tasteful renovations and sleek, modern finishes throughout. The open-concept kitchen and living area is perfect for entertaining guests or relaxing at home. Off the spacious primary bedroom, a private deck offers the

  Ryan Wilson Keller Williams Realty

  5 Pearl Ave Unit 2, Winthrop, MA 02152
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  /23

  $665,000 Sold Aug 27, 2025

  • 1,404 Sq Ft
  • $474/SF
  • 2 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1968

  142 Pleasant St Unit 5, Winthrop, MA 02152

  Welcome to luxury living at Belle Mer! This spacious 2 bed, 2.5 bath condo offers modern comfort and convenience just minutes from Boston and everything Winthrop has to offer—beaches, shops, restaurants, and more. Both bedrooms feature en suite baths, plus there’s a stylish half bath off the chef’s kitchen, complete with Bosch gas appliances and French doors leading to your private patio. Enjoy

  Felicia Giuliano Classified Realty Group

  142 Pleasant St Unit 5, Winthrop, MA 02152
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  /32

  $930,000 Sold Aug 22, 2025

  • 3,432 Sq Ft
  • $271/SF
  • 105 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1958

  68-70 Floyd St, Winthrop, MA 02152

  VERY IMPORTANT! BOM and VERY MUCH AVAILABLE......AMAZING PICTURE POST CARD SETTING FOR THIS BEAUTIFUL HOME IN WINTHROP'S HIGHLANDS LOCATION. This legal 2 family will appeal to single family Buyers as well. A " younger" home compared to most, this multi-level Contemporary has an open floor plan, eat in kitchen open to a great room with skylights and a slider to the large private yard. The

  Sharon Tallent Compass

  68-70 Floyd St, Winthrop, MA 02152
• 

  

  /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
• 

  

  /17

  $350,000 Sold Aug 19, 2025

  • 723 Sq Ft
  • $484/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1971

  300 Governors Dr Unit 9, Winthrop, MA 02152

  Welcome to this lovely Condo, located in an exceptionally affordable complex! This corner unit is a one of a kind in mint move in condition. Ceramic title bath, large closets bedrooms. Many extras. Come take a look!!!! Additionally, this unit comes with the convenience of off-street parking, ensuring your vehicle is always secure. Its prime location offers easy access to public transportation,

  Cleide Paula Dasilva LPT Realty, LLC

  300 Governors Dr Unit 9, Winthrop, MA 02152
• 

  

  /18

  $265,000 Sold Aug 18, 2025

  • 400 Sq Ft
  • $662/SF
  • 54 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1900

  265 Washington Ave Unit 2A, Winthrop, MA 02152

  Looking for the perfect balance of city convenience and suburban tranquility? This newly renovated 1-bedroom, 1-bathroom condo is just a quick ride to the Orient Heights T stop, making your commute to downtown Boston easy. Plus, you're only 5 minutes from Boston Logan Airport, perfect for travel. Enjoy stunning views of the Boston skyline and harbor right from your door. Stroll to nearby

  Pareene Group EXIT Premier Real Estate

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

  

  /12

  $1,120,000 Sold Aug 15, 2025

  • 2,308 Sq Ft
  • $485/SF
  • 1 Day On Market

  • 6 Beds
  • 3 Baths
  • Built 1920

  51 Harbor View Ave, Winthrop, MA 02152

  Contractors, Investors, Savvy buyers looking to build equity. This three family on an oversized lot has stunning ocean and bay views! It offers off street parking, separate utilities, spacious two bedroom units and is close to public transportation, Logan Airport and downtown Boston. Whether you're looking to renovate, rent or occupy, this is your opportunity to own a multi family gem in the

  Mary Ann Cash Charlesgate Realty Group, llc

  51 Harbor View Ave, Winthrop, MA 02152
• 

  

  /28

  $448,000 Sold Aug 15, 2025

  • 1,245 Sq Ft
  • $360/SF
  • 11 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  This bright and sunny second-floor unit offers optimal ocean and sunrise views. Featuring three bedrooms and hardwood floors throughout, the condo includes a private deck off the main bedroom and a rear deck off the kitchen—perfect for soaking in the morning light and sea breeze.Additional highlights include deeded parking, basement storage and in-unit laundry. Ideally located just 15 minutes

  Carol Santoro Coldwell Banker Realty - Marblehead

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

  

  /42

  $1,325,000 Sold Aug 15, 2025

  • 4,671 Sq Ft
  • $284/SF
  • 35 Days On Market

  • 10 Beds
  • 4 Baths
  • Built 1900

  45 Highland Ave, Winthrop, MA 02152

  Incredible investment opportunity in the heart of the Highlands! This oversized 3-family property is has been generating strong income with potential for more. One unit is available for an owner occupant or savvy investor looking to maximize cashflow. Walk-out ground level 2-bedroom apartment. First-floor 2-bedroom unit with an additional office, living room, and dining room. Owner’s unit,

  Jonathan Mathews Legacy Realty Advisors LLC

  45 Highland Ave, Winthrop, MA 02152
• 

  

  /28

  $525,636 Sold Aug 15, 2025

  • 1,120 Sq Ft
  • $469/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1904

  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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  /38

  $1,060,000 Sold Aug 15, 2025

  • 2,692 Sq Ft
  • $394/SF
  • 36 Days On Market

  • 6 Beds
  • 2.5 Baths
  • Built 1900

  86 Chester Ave, Winthrop, MA 02152

  Experience a complete transformation in this meticulously renovated 2-family home. Perched on a prized corner lot, this residence has undergone extensive updates, including new flooring, walls, electrical, kitchen, plumbing, and a newer roof. The result is a modern, move-in-ready space. Enjoy breathtaking, unobstructed views of Winthrop's verdant Golf Course from all three levels. This oversized

  Kyle MacNichol Redfin Corp.

  86 Chester Ave, Winthrop, MA 02152
• 

  

  /31

  $492,500 Sold Aug 14, 2025

  • 1,595 Sq Ft
  • $309/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1916

  110 Summit Ave Unit 1, Winthrop, MA 02152

  Coastal charm meets timeless elegance in this spacious 3-bedroom, 2-bath first-floor condo just moments from Winthrop’s stunning shoreline. Nestled within a beautifully maintained Victorian, this one-of-a-kind home blends historic character with everyday convenience. From the moment you enter, you’ll appreciate the soaring ceilings, intricate dental crown molding, sunlit bay windows, and

  Alison ludwig Keller Williams Realty-Merrimack

  110 Summit Ave Unit 1, Winthrop, MA 02152

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