56

Homes for Sale near Arthur T. Cummings Elementary School

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  • 148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152
    148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152
    148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152
    /21

    $669,009

    • 2 Beds
    • 2 Baths
    • 971 Sq Ft

    148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152

    Welcome to your slice of coastal paradise just outside of Boston. Nestled in the quaint seaside town of Winthrop, this stunning condo offers an unparalleled living experience with exceptional water views.Step inside to discover a meticulously designed space, with an open-concept layout that seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere flooded with

    Agent Photo

    Nicole Bettano

    Lantern Residential

    (617) 618-6576

    148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152
  • 10 Somerset Ave Unit 204, Winthrop, MA 02152
    10 Somerset Ave Unit 204, Winthrop, MA 02152
    10 Somerset Ave Unit 204, Winthrop, MA 02152
    /13

    $598,395 Open Sat 10AM - 11:30AM

    • 2 Beds
    • 2 Baths
    • 832 Sq Ft

    10 Somerset Ave Unit 204, Winthrop, MA 02152

    Welcome to Unit 204 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 1+-bed, 1-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing and an exterior private balcony. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 204, Winthrop, MA 02152
  • 1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
    /42

    $575,000 Open Sat 11AM - 1PM

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

    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152

    Welcome Home to 1 Seal Harbor! Enjoy the ease of coastal living in this beautiful 2-bed, 2-bath corner unit designed for comfort and convenience. Offering a bright, open space, this home features a private balcony with ocean views—perfect for morning coffee or relaxing at sunset. The spacious primary suite offers an en-suite bath and expansive walk-in closet. Freshly painted with new carpet in

    Camilo & Co. Group Realty One Group Nest

    1 Seal Harbor Rd Unit 415, Winthrop, MA 02152
  • 5 Quincy Ave, Winthrop, MA 02152
    5 Quincy Ave, Winthrop, MA 02152
    5 Quincy Ave, Winthrop, MA 02152
    /41

    $950,000

    • 3 Beds
    • 2 Baths
    • 2,820 Sq Ft

    5 Quincy Ave, Winthrop, MA 02152

    Welcome to 5 Quincy Avenue, an architecturally stunning Bungalow located in Winthrop's highly sought-after Highlands neighborhood . This sun-filled 3-bedroom, 2-bath Craftsman home has an open-concept living and dining area featuring original rich oak woodwork, built-in cabinets, hardwood floors, decorative molding, wainscoting, and a fireplace. The renovated eat-in kitchen, equipped with

    William Raye William Raveis R.E. & Home Services

    5 Quincy Ave, Winthrop, MA 02152
  • 3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 137, Winthrop, MA 02152
    /31

    $729,995 Open Sun 11AM - 12PM

    • 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
  • 3 Seal Harbor Rd Unit 133, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 133, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 133, Winthrop, MA 02152
    /25

    $649,995 Open Sun 11AM - 12PM

    • 1 Bed
    • 1 Bath
    • 910 Sq Ft

    3 Seal Harbor Rd Unit 133, Winthrop, MA 02152

    Enter coastal luxury living at The Seal Harbor Condominiums! This 1 bed/1 bath unique unit doesn't just offer an unbeatable location- it has been meticulously renovated from top to bottom with premium finishes & custom touches throughout. Updates include new tile flooring, all-new wooden six-panel doors with glass knobs, fully rewired living room, kitchen, and entryway for modern convenience.

    Christine Goldstein Lyv Realty

    3 Seal Harbor Rd Unit 133, Winthrop, MA 02152
  • 10 Somerset Ave Unit 201, Winthrop, MA 02152
    10 Somerset Ave Unit 201, Winthrop, MA 02152
    10 Somerset Ave Unit 201, Winthrop, MA 02152
    /29

    $629,000 Open Sat 10AM - 11:30AM

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    10 Somerset Ave Unit 201, Winthrop, MA 02152

    Welcome to Unit 201 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 and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 201, Winthrop, MA 02152
  • 3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
    /30

    $525,000 Open Sat 11AM - 12:30PM

    • 1 Bed
    • 1 Bath
    • 840 Sq Ft

    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152

    Situated at the ocean's edge in Winthrop, Seal Harbor is located just fifteen minutes from Boston's financial district. Building is amenity-rich- 24/7 concierge, on-site management, secure underground deeded garage parking, heated outdoor pool with shower, bathrooms, full poolhouse kitchen, outdoor Jacuzzi & 2 gas grills, year-round access to an indoor pool on the 9th floor, complete with

    Mark Carangelo Mark Carangelo

    3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
  • 9 Marshall St, Winthrop, MA 02152
    9 Marshall St, Winthrop, MA 02152
    9 Marshall St, Winthrop, MA 02152
    /34

    $735,000

    • 5 Beds
    • 3.5 Baths
    • 2,475 Sq Ft

    9 Marshall St, Winthrop, MA 02152

    Discover the best of coastal living in this Winthrop waterfront community, where local dining, seaside charm, and effortless access to public transit create a lifestyle of ease and enjoyment. Spanning approximately 2,475 square feet, this expansive 5-bedroom, 3.5-bath home offers three levels of versatile living space along with a private outdoor deck and yard. Ideally situated within walking

    Ricardo Rodriguez Coldwell Banker Realty - Boston

    9 Marshall St, Winthrop, MA 02152
  • 3 Seal Harbor Rd Unit 344, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 344, Winthrop, MA 02152
    3 Seal Harbor Rd Unit 344, Winthrop, MA 02152
    /29

    $695,000 Open Sat 11AM - 12:30PM

    • 2 Beds
    • 2 Baths
    • 1,302 Sq Ft

    3 Seal Harbor Rd Unit 344, Winthrop, MA 02152

    Situated at the ocean's edge in Winthrop, Seal Harbor is located just fifteen minutes from Boston's financial district. Building is amenity-rich- 24/7 concierge, on-site management, secure underground deeded garage parking, heated outdoor pool with shower, bathrooms, full poolhouse kitchen, outdoor Jacuzzi & 2 gas grills, year-round access to an indoor pool on the 9th floor, complete with

    Mark Carangelo Mark Carangelo

    3 Seal Harbor Rd Unit 344, Winthrop, MA 02152
  • 70 Edgehill Rd, Winthrop, MA 02152
    70 Edgehill Rd, Winthrop, MA 02152
    70 Edgehill Rd, Winthrop, MA 02152
    /22

    $1,199,000

    • 4 Beds
    • 3 Baths
    • 2,654 Sq Ft

    70 Edgehill Rd, Winthrop, MA 02152

    Nestled on a peaceful street, this charming single family home presents an incredible opportunity for generational living. Sandwiched between Donavan's Beach and Ingleside Park you can walk and enjoy the coastal living, with space to play. Recently renovated from rooftop to lower level, this is a turn key home. Multiple levels for gathers, private workspace with loads of natural light. Incredible

    Kelvin Peters MIG

    70 Edgehill Rd, Winthrop, MA 02152
  • 10 Beach Rd Unit 1, Winthrop, MA 02152
    10 Beach Rd Unit 1, Winthrop, MA 02152
    10 Beach Rd Unit 1, Winthrop, MA 02152
    /23

    $559,000

    • 3 Beds
    • 1 Bath
    • 1,377 Sq Ft

    10 Beach Rd Unit 1, Winthrop, MA 02152

    Just one block from Winthrop Beach, this spacious and inviting condo offers 1,377 SqFt of comfortable living. With 3 large bedrooms and 1 full bath, there’s plenty of room for working from home, entertaining, or simply relaxing.Step inside to discover an open-concept living and dining area that flows seamlessly into a large, modern kitchen, featuring gas cooking, ample counter space, and a

    Rogelio Zuniga United Brokers

    10 Beach Rd Unit 1, Winthrop, MA 02152
  • 35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    35 Somerset Ave Unit 6, Winthrop, MA 02152
    /31

    $515,000

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    35 Somerset Ave Unit 6, Winthrop, MA 02152

    UPSCALE 2 BEDROOM, 2 BATH TOP FLOOR UNIT WITH ROOFTOP EXCLUSIVE OUTDOOR DECK......A two year old renovation and a must see! Bright sun-filled condo with a spacious kitchen/living room combo with plenty of cabinets and huge center island with pretty pendant lighting......perfect for entertaining and personal enjoyment. Two large bedrooms, one a main suite with it's own full bath and the other

    Sharon Tallent Compass

    35 Somerset Ave Unit 6, Winthrop, MA 02152
  • 62 Lowell Rd, Winthrop, MA 02152
    62 Lowell Rd, Winthrop, MA 02152
    62 Lowell Rd, Winthrop, MA 02152
    /23

    $780,000 Open Sun 12PM - 1:30PM

    • 5 Beds
    • 2.5 Baths
    • 1,923 Sq Ft

    62 Lowell Rd, Winthrop, MA 02152

    Welcome to the "Maze!" This Whittemore designed home is solidly built and filled with character and charm. With great bones and endless potential, this 4+ bedroom, 2.5 bath single is the perfect canvas to create space you've been dreaming of, all in one of Winthrop's most sought after locations. Some of the wonderful features include a wood-burning fireplace, bright eat in kitchen with

    Mary Ann Cash Charlesgate Realty Group, llc

    62 Lowell Rd, Winthrop, MA 02152
  • 2 Deane Ave, Winthrop, MA 02152
    2 Deane Ave, Winthrop, MA 02152
    2 Deane Ave, Winthrop, MA 02152
    /42

    $865,000 Open Sat 11:30AM - 1PM

    • 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
  • 23 Trident Ave Unit 2, Winthrop, MA 02152
    23 Trident Ave Unit 2, Winthrop, MA 02152
    23 Trident Ave Unit 2, Winthrop, MA 02152
    /25

    $499,900

    • 3 Beds
    • 1 Bath
    • 1,369 Sq Ft

    23 Trident Ave Unit 2, Winthrop, MA 02152

    Steps to the BEACH. Minutes to BOSTON. Seconds to fall in LOVE. This isn’t just a condo - it’s a whole new pace of life. Welcome to 23 Trident Ave where you have the opportunity to make your home ownership dreams a reality. This beautiful 4 Bed 1 Bath unit with a heated bonus room has been meticulously maintained. Spacious kitchen with ample cabinet space, granite counters, stainless appliances

    Julian Addy William Raveis R.E. & Home Services

    23 Trident Ave Unit 2, Winthrop, MA 02152
  • 279 Shirley St Unit 2, Winthrop, MA 02152
    279 Shirley St Unit 2, Winthrop, MA 02152
    279 Shirley St Unit 2, Winthrop, MA 02152
    /15

    $529,000 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 1 Bath
    • 1,105 Sq Ft

    279 Shirley St Unit 2, Winthrop, MA 02152

    Like-new 3-bedroom condo near the beach with WATER VIEWS! Built in 2023, this sun-filled home features hardwood floors, central air, a stylish kitchen with white shaker cabinets, high-end appliances, and a deeded off-street parking space. Oversized windows for those envious ocean views in the front and the Boston skyline over Winthrop Golf Club in the back. Just minutes to public transportation

    Adam Mundt Kingston Real Estate & Management

    279 Shirley St Unit 2, Winthrop, MA 02152
  • 550 Pleasant St Unit 307, Winthrop, MA 02152
    550 Pleasant St Unit 307, Winthrop, MA 02152
    550 Pleasant St Unit 307, Winthrop, MA 02152
    /19

    $529,900

    • 1 Bed
    • 1 Bath
    • 1,153 Sq Ft

    550 Pleasant St Unit 307, Winthrop, MA 02152

    Experience waterfront living in this beautifully updated 1-bedroom, 1-bath condo at the Residences at Atlantis Marina. Enjoy stunning marina views from your private balcony, ideal for relaxing or entertaining. The unit features a modern kitchen with stainless steel appliances, granite countertops, and ample storage throughout. Additional highlights include in-unit laundry and two assigned parking

    Daniel Clucas Reference Real Estate

    550 Pleasant St Unit 307, Winthrop, MA 02152
  • 136 Pauline St, Winthrop, MA 02152
    136 Pauline St, Winthrop, MA 02152
    136 Pauline St, Winthrop, MA 02152
    /42

    $867,000

    • 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
  • 600 Shirley St Unit 3, Winthrop, MA 02152
    600 Shirley St Unit 3, Winthrop, MA 02152
    600 Shirley St Unit 3, Winthrop, MA 02152
    /32

    $549,900

    • 2 Beds
    • 2 Baths
    • 773 Sq Ft

    600 Shirley St Unit 3, Winthrop, MA 02152

    “The Cove at 600” was converted in 2022 and is located on the site of the historic Crystal Cove Hotel with breathtaking views of the Boston Skyline and the Atlantic Ocean. Unit 3, located on the side of the building with a private entrance, exclusive use patio and exclusive use deck at the front of the building offers many ways to take in the view and the sea air. The open concept living room and

    Erika Leigh Pereira Keller Williams Realty Boston Northwest

    600 Shirley St Unit 3, Winthrop, MA 02152
  • 80 Shirley St Unit 2, Winthrop, MA 02152
    80 Shirley St Unit 2, Winthrop, MA 02152
    80 Shirley St Unit 2, Winthrop, MA 02152
    /39

    $499,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft

    80 Shirley St Unit 2, 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 2, Winthrop, MA 02152
  • 130 Shirley St Unit 204, Winthrop, MA 02152
    130 Shirley St Unit 204, Winthrop, MA 02152
    130 Shirley St Unit 204, Winthrop, MA 02152
    /15

    $499,900 Open Fri 3PM - 4:30PM

    • 1 Bed
    • 1 Bath
    • 611 Sq Ft

    130 Shirley St Unit 204, Winthrop, MA 02152

    Discover the perfect blend of modern design and seaside charm at 130 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed

    Kovacs Savage Team Byrnes Real Estate Group LLC

    130 Shirley St Unit 204, Winthrop, MA 02152
  • 130 Shirley St Unit 202, Winthrop, MA 02152
    130 Shirley St Unit 202, Winthrop, MA 02152
    130 Shirley St Unit 202, Winthrop, MA 02152
    /15

    $569,900 Open Fri 3PM - 4:30PM

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    130 Shirley St Unit 202, Winthrop, MA 02152

    Discover the perfect blend of modern design and seaside charm at 130 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This two-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed

    Kovacs Savage Team Byrnes Real Estate Group LLC

    130 Shirley St Unit 202, Winthrop, MA 02152
  • 129 Strandway, Winthrop, MA 02152
    129 Strandway, Winthrop, MA 02152
    129 Strandway, Winthrop, MA 02152
    /42

    $1,324,900 Open Sun 1PM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,640 Sq Ft

    129 Strandway, Winthrop, MA 02152

    Discover true beachfront living at 129 Strandway, where every day feels like vacation. Step from your back door directly into the sand and enjoy panoramic ocean views from the heated sunroom. The main level offers an updated kitchen with marble counters, a cozy fireplaced living room, two bedrooms, and a convenient beach-entry bath. The spacious second-floor primary suite provides its own private

    Kovacs Savage Team Byrnes Real Estate Group LLC

    129 Strandway, Winthrop, MA 02152
  • 41 Summit Ave, Winthrop, MA 02152
    41 Summit Ave, Winthrop, MA 02152
    41 Summit Ave, Winthrop, MA 02152
    /34

    $899,000

    • 4 Beds
    • 2 Baths
    • 2,386 Sq Ft

    41 Summit Ave, Winthrop, MA 02152

    Lovely custom built ranch offering endless possibilities! Perfect for multi-generational living or added income with a fully equipped lower level apartment. The main floor features a cherry wood kitchen with granite countertops, a spacious fireplace living room, tiled bath with separate shower and tub, generous bedrooms, den, and a bright sunroom with ocean views. Enjoy central air and an

    Elizabeth Ferrara Cottage Hill Real Estate

    41 Summit Ave, Winthrop, MA 02152
  • 16 Woodside Park, Winthrop, MA 02152
    16 Woodside Park, Winthrop, MA 02152
    16 Woodside Park, Winthrop, MA 02152
    /25

    $719,900 Open Sat 12PM - 1:30PM

    • 3 Beds
    • 1 Bath
    • 1,654 Sq Ft

    16 Woodside Park, Winthrop, MA 02152

    Discover the charm of the highly sought-after Woodside Park neighborhood! Homes in this area rarely become available, making this opportunity truly special. Nestled in a picturesque setting that evokes a sense of nostalgia, this late 1800's 3-bedroom Farmhouse Colonial captivates with its enchanting Winthrop harbor views from a welcoming veranda. The home features hardwood floors throughout, a

    James Polino Compass

    16 Woodside Park, Winthrop, MA 02152
  • 19 Pleasant Park Rd, Winthrop, MA 02152
    19 Pleasant Park Rd, Winthrop, MA 02152
    19 Pleasant Park Rd, Winthrop, MA 02152
    /36

    $728,900 Open Sun 11AM - 12:30PM

    • 3 Beds
    • 1.5 Baths
    • 1,325 Sq Ft

    19 Pleasant Park Rd, Winthrop, MA 02152

    Welcome to 19 Pleasant Park Road - a beautifully updated coastal retreat that blends timeless character with modern comfort. Step inside to discover warm hardwood floors, sun-filled rooms, and a layout designed for easy everyday living. The inviting dining room flows seamlessly into the living space, while the updated kitchen features stainless steel appliances and classic white cabinetry. Both

    Laura Cohron Fiv Realty Co.

    19 Pleasant Park Rd, Winthrop, MA 02152
  • 1000 Governors Dr Unit 25, Winthrop, MA 02152
    1000 Governors Dr Unit 25, Winthrop, MA 02152
    1000 Governors Dr Unit 25, Winthrop, MA 02152
    /27

    $399,900

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    1000 Governors Dr Unit 25, Winthrop, MA 02152

    Welcome to Governor’s Park Condominiums in Winthrop! This well-maintained third-floor, two-bedroom, one-bath unit offers the perfect balance of city convenience and coastal charm. Featuring an open-concept layout with a spacious living room and kitchen/dining area, this home also includes hardwood floors, granite countertops, SS appliances, a private balcony, and two deeded off-street parking

    Lindita Murrizi Return Realty Group, Inc.

    1000 Governors Dr Unit 25, Winthrop, MA 02152
  • 41 Harbor View Ave, Winthrop, MA 02152
    41 Harbor View Ave, Winthrop, MA 02152
    41 Harbor View Ave, Winthrop, MA 02152
    /27

    $1,055,000

    • 4 Beds
    • 3 Baths
    • 2,028 Sq Ft

    41 Harbor View Ave, Winthrop, MA 02152

    The street name; 'Harbor View Ave" says it all! Sweeping unobstructed views of the open ocean, Boston Harbor, & city skyline! Nestled atop one of Winthrop’s highest elevations, delivering a rare combination of breathtaking coastal scenery & beach access. This sun-drenched 3 unit home offers 4 bedrooms, 3 full baths, garage parking, making it ideal for homeowners, developers, or investors. From

    Brian Perrin Brian J. Perrin Real Estate

    41 Harbor View Ave, Winthrop, MA 02152
  • 550 Pleasant St Unit 11D, Winthrop, MA 02152
    550 Pleasant St Unit 11D, Winthrop, MA 02152
    550 Pleasant St Unit 11D, Winthrop, MA 02152
    /30

    $89,000

    • 2 Beds
    • 2 Baths
    • 600 Sq Ft

    550 Pleasant St Unit 11D, Winthrop, MA 02152

    Waterfront living at its finest with this live-aboard houseboat, offering all the comforts of a traditional condo. Built in 1989 by Hatteras Boats, one of the most respected names in the industry, this flagship model combines quality craftsmanship and functional charm. Step inside to an inviting open-concept living room and kitchen, filled with natural light, enhanced by high ceilings. The

    Drew Boujoulian Coldwell Banker Realty - Boston

    550 Pleasant St Unit 11D, Winthrop, MA 02152
  • 1001 Shirley St Unit 1, Winthrop, MA 02152
    1001 Shirley St Unit 1, Winthrop, MA 02152
    1001 Shirley St Unit 1, Winthrop, MA 02152
    /25

    $1,200,000

    • 2 Beds
    • 2.5 Baths
    • 1,868 Sq Ft

    1001 Shirley St Unit 1, Winthrop, MA 02152

    As the flagship residence at The Pearl, Unit 1 showcases one of the most spacious layouts in the collection, blending ocean views with striking modern details. Steps from the shoreline in Winthrop’s Point Shirley, it spans two levels with hardwood floors, soaring cathedral beamed ceilings, and a fireplace that anchors the living room while a second warms the primary suite. The chef’s kitchen is

    The Reference Group Reference Real Estate

    1001 Shirley St Unit 1, Winthrop, MA 02152
  • 1001 Shirley St Unit 3, Winthrop, MA 02152
    1001 Shirley St Unit 3, Winthrop, MA 02152
    1001 Shirley St Unit 3, Winthrop, MA 02152
    /21

    $979,000

    • 2 Beds
    • 2.5 Baths
    • 1,561 Sq Ft

    1001 Shirley St Unit 3, Winthrop, MA 02152

    Once a cornerstone of the Point Shirley community, this former church has been completely reimagined into five striking townhomes that blend architectural soul with modern precision. The Pearl is a bold statement... Thoughtful design, coastal light, and space that actually feels like home. Unit 3 offers over 1,500 square feet across two levels with an open main floor that feels expansive but

    The Reference Group Reference Real Estate

    1001 Shirley St Unit 3, Winthrop, MA 02152
  • 308 Bowdoin St, Winthrop, MA 02152
    308 Bowdoin St, Winthrop, MA 02152
    308 Bowdoin St, Winthrop, MA 02152
    /42

    $1,067,000

    • 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 offers exceptional size, flexibility, and strong rental potential. A cabin/garage plus driveway for 4 cars adds rare value, while the lot provides outdoor living space. Interiors are well maintained and move-in ready.The first-floor unit

    James Polino Compass

    308 Bowdoin St, Winthrop, MA 02152
  • 51 Cutler St Unit 3, Winthrop, MA 02152
    51 Cutler St Unit 3, Winthrop, MA 02152
    51 Cutler St Unit 3, Winthrop, MA 02152
    /28

    $685,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 1,283 Sq Ft

    51 Cutler St Unit 3, Winthrop, MA 02152

    Enjoy turn-key living just steps from Winthrop Beach! This stunning condo blends seaside tranquility with modern comfort. A dramatic picture window in the living room frames sweeping ocean views, filling the home with natural light and salt air breezes. Sun-filled open spaces feature hardwood floors and a coastal-modern design. The chef's kitchen offers sleek cabinetry, high-end appliances, and a

    Sobel Group Compass

    51 Cutler St Unit 3, Winthrop, MA 02152
  • 14 Pleasant Park Rd, Winthrop, MA 02152
    14 Pleasant Park Rd, Winthrop, MA 02152
    14 Pleasant Park Rd, Winthrop, MA 02152
    /42

    $729,900 Open Sun 11AM - 1PM

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

    14 Pleasant Park Rd, Winthrop, MA 02152

    WELCOME HOME to 14 Pleasant Park Road...BEEN IN THE SAME FAMILY FOR OVER 17 YEARS!!!...This BEAUTIFUL 4 BEDROOMS/ 1 FULL BATH 'GAMBREL COLONIAL STYLE HOME' is ready for new owners...1st FLOOR offers WELCOMING FOYER w/Hardwood Floors, CHERRY KITCHEN CABINETS w/GRANITE COUNTERS & GRANITE ISLAND w/Tiled Flooring & Recess Lighting, DINING ROOM w/Hardwood Floors, LIVING ROOM w/Hardwood Floors...2nd

    Regina Paratore RE/MAX 360

    14 Pleasant Park Rd, Winthrop, MA 02152
  • 191 Court Rd Unit 3, Winthrop, MA 02152
    191 Court Rd Unit 3, Winthrop, MA 02152
    191 Court Rd Unit 3, Winthrop, MA 02152
    /38

    $1,125,000 Open Sun 12PM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,575 Sq Ft

    191 Court Rd Unit 3, Winthrop, MA 02152

    Coastal luxury meets modern elegance in this completely renovated 4-bed, 3.5-bath waterfront condo with breathtaking ocean and Boston skyline views. Unit 3 at 191 Court features two private owner’s suites on separate levels, sleek modern bathrooms, and an open-concept living/dining area filled with natural light and ocean breezes. The chef’s kitchen boasts premium Samsung stainless steel

    Kristen Karshis Keller Williams Realty Evolution

    191 Court Rd Unit 3, Winthrop, MA 02152
  • 483 Shirley St Unit 4, Winthrop, MA 02152
    483 Shirley St Unit 4, Winthrop, MA 02152
    483 Shirley St Unit 4, Winthrop, MA 02152
    /13

    $290,000

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft

    483 Shirley St Unit 4, Winthrop, MA 02152

    LOWEST PRICED CONDO IN WINTHROP. If you’ve been looking for a 1 bed 1 bath condo in the heart of Winthrop Shore, look no further. Conveniently located next to some of the best restaurants & shops in town, and only a street away from Winthrop Beach. HOA fee includes heat, hot water, and much more. Come make this hidden gem your own - and yes your pets are welcome! Just minutes from Boston, a

    Team Lillian Montalto Lillian Montalto Signature Properties

    483 Shirley St Unit 4, Winthrop, MA 02152
  • 10 Somerset Ave Unit 304, Winthrop, MA 02152
    10 Somerset Ave Unit 304, Winthrop, MA 02152
    10 Somerset Ave Unit 304, Winthrop, MA 02152
    /11

    $399,000 Open Sat 10AM - 11:30AM

    • 1 Bed
    • 1 Bath
    • 546 Sq Ft

    10 Somerset Ave Unit 304, Winthrop, MA 02152

    Welcome to 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. The

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 304, Winthrop, MA 02152
  • 142 Pleasant St Unit 2, Winthrop, MA 02152
    142 Pleasant St Unit 2, Winthrop, MA 02152
    142 Pleasant St Unit 2, Winthrop, MA 02152
    /14

    $549,000

    • 1 Bed
    • 1.5 Baths
    • 1,039 Sq Ft

    142 Pleasant St Unit 2, Winthrop, MA 02152

    This two-level corner unit offers a rare blend of comfort and convenience in a well-constructed building just minutes from Boston. The open layout features a modern kitchen, gas fireplace, and hardwood floors throughout, with a freshly painted interior that feels move-in ready. Two outdoor spaces—a private roof deck and patio—extend your living options, while deeded parking plus abundant visitor

    Federico Creatini eXp Realty

    142 Pleasant St Unit 2, Winthrop, MA 02152
  • 144 Quincy Ave, Winthrop, MA 02152
    144 Quincy Ave, Winthrop, MA 02152
    144 Quincy Ave, Winthrop, MA 02152
    /33

    $1,800,000

    • 5 Beds
    • 4 Baths
    • 3,866 Sq Ft

    144 Quincy Ave, Winthrop, MA 02152

    Welcome to the Highlands, Winthrop’s most coveted neighborhood- where modern design meets sweeping Boston views. This newly built two-family sits high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main unit offers an open layout with living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area opening

    Leighann Eruzione Lantern Residential

    144 Quincy Ave, Winthrop, MA 02152

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