42

Homes for Sale near Winthrop High School

Section Image
  • 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 12:30PM - 1:30PM

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

    10 Somerset Ave Unit 201, 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 201, Winthrop, MA 02152
  • 100 Cottage Ave, Winthrop, MA 02152
    100 Cottage Ave, Winthrop, MA 02152
    100 Cottage Ave, Winthrop, MA 02152
    /37

    $879,900 Open Fri 4PM - 5:30PM

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

    100 Cottage Ave, Winthrop, MA 02152

    Ideally located just steps from the Winthrop Yacht Club, The Landing Marina, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace, plus two additional rooms perfect for

    The Reference Group Reference Real Estate

    100 Cottage Ave, Winthrop, MA 02152
  • 136 Pauline St, Winthrop, MA 02152
    136 Pauline St, Winthrop, MA 02152
    136 Pauline St, Winthrop, MA 02152
    /42

    $899,000 Open Sun 12PM - 2PM

    • 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
  • 17 Edgehill Rd, Winthrop, MA 02152
    17 Edgehill Rd, Winthrop, MA 02152
    17 Edgehill Rd, Winthrop, MA 02152
    /42

    $799,900

    • 5 Beds
    • 3 Baths
    • 2,114 Sq Ft

    17 Edgehill Rd, Winthrop, MA 02152

    Welcome home to 17 Edgehill Road! Nestled in a desirable waterfront community, this spacious single-family is located steps from the harbor & home to some of the most incredible sunset views at Donovan's Beach! Along with being a shoreline neighborhood, Edgehill is known for its charming surroundings next to the lovely Ingleside Park. Here you'll find the kind of space & living that encompasses

    Atiyeh Cassidy Blue Sky Realty

    17 Edgehill Rd, Winthrop, MA 02152
  • 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

    $679,000

    • 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

    Nicole Bettano Lantern Residential

    148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152
  • 32 Hale Ave, Winthrop, MA 02152
    32 Hale Ave, Winthrop, MA 02152
    32 Hale Ave, Winthrop, MA 02152
    /42

    $849,000

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

    32 Hale Ave, Winthrop, MA 02152

    A spectacular hilltop home with unmatched 360 views. A once-in-a-lifetime opportunity to own this exceptional hilltop property offering panoramic views of the Atlantic Ocean, Boston Harbor, Winthrop Harbor, and the Boston skyline. Ocean views from every room and all three decks make this home truly one of a kind. Steeped in history, this site was purposely chosen by Patriot troops during the

    Sharon Tallent Compass

    32 Hale Ave, Winthrop, MA 02152
  • 143 Morton St, Winthrop, MA 02152
    143 Morton St, Winthrop, MA 02152
    143 Morton St, Winthrop, MA 02152
    /24

    $799,900

    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    143 Morton St, Winthrop, MA 02152

    Welcome to this spacious single-family home in Winthrop! Step into a large living room that flows into a formal dining room and an updated kitchen (2016). A full bath on the first floor adds convenience, and a cozy family room off the kitchen offers great bonus space. Step out to the deck and enjoy a generous, fenced-in yard—perfect for outdoor entertaining or relaxing. Upstairs, you'll find four

    The Reference Group Reference Real Estate

    143 Morton St, 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
    /27

    $560,000

    • 2 Beds
    • 2 Baths
    • 823 Sq Ft

    35 Somerset Ave Unit 6, Winthrop, MA 02152

    Welcome to 35 Somerset Ave, Unit #6 (Pent House), nestled in the heart of Winthrop! This stunning newly renovated 2-bedroom, 2 full bathroom condo, offers a perfect fusion of modern comfort and seaside charm. Located just moments from the beach, this inviting unit offers breathtaking views from its massive private roof deck and seamless access to downtown and the beach. Every aspect of this unit

    John Maggio EVO Real Estate Group, LLC

    35 Somerset Ave Unit 6, Winthrop, MA 02152
  • 212 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
    212 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
    212 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
    /16

    $569,000 Open Sat 12PM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft

    212 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

    Imagine waking up to the soothing sound of waves and sipping your morning coffee as the ocean stretches out before you. This spacious first-floor condo invites you to live effortlessly by the water, with sunlight pouring through oversized windows and an open-concept living and dining area designed for both quiet moments and lively gatherings. The modern kitchen, outfitted with sleek Viking

    Leighann Eruzione Lantern Residential

    212 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
  • 54 Townsend St, Winthrop, MA 02152
    54 Townsend St, Winthrop, MA 02152
    54 Townsend St, Winthrop, MA 02152
    /42

    $650,000 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,483 Sq Ft

    54 Townsend St, Winthrop, MA 02152

    Welcome to this delightful 1926 Cottage/Bungalow located in the highly sought-after Point Shirley section of Winthrop.With 7+ rooms, 3+ bdrms, and 13⁄4 baths, this lovingly maintained home offers timeless character and stunning views. Begin your day on the charming front porch perfect for morning coffee, a good book, or an evening beverage while soaking in the coastal scenery. Inside, the living

    Cathie Curran Charlesgate Realty Group, llc

    54 Townsend St, Winthrop, MA 02152
  • 72 Sewall Ave, Winthrop, MA 02152
    72 Sewall Ave, Winthrop, MA 02152
    72 Sewall Ave, Winthrop, MA 02152
    /41

    $1,265,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,214 Sq Ft

    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
  • 500 Shirley St, Winthrop, MA 02152
    500 Shirley St, Winthrop, MA 02152
    500 Shirley St, Winthrop, MA 02152
    /36

    $829,900 Open Sat 12PM - 1:30PM

    • 4 Beds
    • 2 Baths
    • 2,088 Sq Ft

    500 Shirley St, Winthrop, MA 02152

    Located just 3.5 miles from the game-changing Suffolk Downs redevelopment, this fantastic two-family home offers incredible long-term upside in one of the fastest-growing areas north of Boston. The project promises millions of square feet of new housing, retail, parks, and life science space—adding immense value & convenience to the surrounding neighborhoods. Just steps from the beach, this

    Jose Zambrano RE/MAX 360

    500 Shirley St, Winthrop, MA 02152
  • 12 Park Ave, Winthrop, MA 02152
    12 Park Ave, Winthrop, MA 02152
    12 Park Ave, Winthrop, MA 02152
    /27

    $699,000 Open Sat 11:30AM - 1PM

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

    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
  • 37-39 Hutchinson St, Winthrop, MA 02152
    37-39 Hutchinson St, Winthrop, MA 02152
    37-39 Hutchinson St, Winthrop, MA 02152
    /41

    $899,000 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 2 Baths
    • 2,958 Sq Ft

    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
  • 10 Somerset Ave Unit 408, Winthrop, MA 02152
    10 Somerset Ave Unit 408, Winthrop, MA 02152
    10 Somerset Ave Unit 408, Winthrop, MA 02152
    /27

    $539,900 Open Sat 12:30PM - 1:30PM

    • 1 Bed
    • 1 Bath
    • 767 Sq Ft

    10 Somerset Ave Unit 408, Winthrop, MA 02152

    Step into a spacious 1-bedroom + den home at The Somerset, Winthrop’s newest boutique condo community blending coastal charm with modern comfort. This thoughtfully designed layout offers an open-concept living space, a versatile den ideal for a home office or guest room, and a walk-in closet in the bedroom.Enjoy upscale finishes throughout—quartz countertops, stainless steel appliances, central

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 408, Winthrop, MA 02152
  • 44 Cliff Ave Unit 3, Winthrop, MA 02152
    44 Cliff Ave Unit 3, Winthrop, MA 02152
    44 Cliff Ave Unit 3, Winthrop, MA 02152
    /33

    $679,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,849 Sq Ft

    44 Cliff Ave Unit 3, Winthrop, MA 02152

    Welcome to this expansive 1,850 sq ft condo that lives like a single-family home, perfectly perched in the highly desirable Winthrop Highlands. Enjoy breathtaking panoramic ocean views from not one, but two private decks. Inside, you're greeted by sun-drenched spaces, soaring ceilings, and a wide open floor plan that makes entertaining effortless. The modern eat-in kitchen features direct access

    Jenny Golic Lantern Residential

    44 Cliff Ave Unit 3, Winthrop, MA 02152
  • 876 Shirley St Unit 1, Winthrop, MA 02152
    876 Shirley St Unit 1, Winthrop, MA 02152
    876 Shirley St Unit 1, Winthrop, MA 02152
    /40

    $859,999

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    876 Shirley St Unit 1, Winthrop, MA 02152

    Direct Beach Front Living. Feel like you're on vacation every day! This spacious 2 level, 7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day. Every day the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining

    Jim Iannuzzi Amo Realty - Boston City Properties

    876 Shirley St Unit 1, Winthrop, MA 02152
  • 123 Buchanan St, Winthrop, MA 02152
    123 Buchanan St, Winthrop, MA 02152
    123 Buchanan St, 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
  • 45 Highland Ave, Winthrop, MA 02152
    45 Highland Ave, Winthrop, MA 02152
    45 Highland Ave, Winthrop, MA 02152
    /42

    $1,400,000

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

    45 Highland Ave, Winthrop, MA 02152

    ***OPEN HOUSE SUN 1-2:30pm ***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

    Jonathan Mathews Legacy Realty Advisors LLC

    45 Highland Ave, Winthrop, MA 02152
  • 26 Enfield Rd, Winthrop, MA 02152
    26 Enfield Rd, Winthrop, MA 02152
    26 Enfield Rd, Winthrop, MA 02152
    /41

    $849,900

    • 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
  • 56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    56 Main St, Winthrop, MA 02152
    /19

    $799,900

    • 4 Beds
    • 2 Baths
    • 2,103 Sq Ft

    56 Main St, Winthrop, MA 02152

    OPPORTUNITY KNOCKS.......Two family with large yard located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! The home was gutted in 2001. The owner's unit is on the second and third floors with an open floor plan and loads of natural lighting. It contains a living room, dining area, kitchen, bath and bedroom on the second floor and a

    Sharon Tallent Compass

    56 Main St, Winthrop, MA 02152
  • 328-330 Revere St, Winthrop, MA 02152
    328-330 Revere St, Winthrop, MA 02152
    328-330 Revere St, Winthrop, MA 02152
    /42

    $1,170,000

    • 5 Beds
    • 2 Baths
    • 2,151 Sq Ft

    328-330 Revere St, Winthrop, MA 02152

    This property is what the competition see as a "Triple Threat" *TURN KEY *LOCATION & *BIG LOT OF LAND! The first floor's Craftsman style details have had restoration, preserving the stain glass windows, hardwood floors, working wood fireplace, beamed ceilings & built-ins to really embody the character of days gone by. A gas stove with hood vent, & sliders to a deck off the kitchen, makes this

    Debra Messana LAER Realty Partners

    328-330 Revere St, Winthrop, MA 02152
  • 88 Grand View Ave, Winthrop, MA 02152
    88 Grand View Ave, Winthrop, MA 02152
    88 Grand View Ave, Winthrop, MA 02152
    /35

    $665,000

    • 2 Beds
    • 1 Bath
    • 1,262 Sq Ft

    88 Grand View Ave, Winthrop, MA 02152

    Welcome to the beach! Enjoy breathtaking sunset views over the city your nightly show from home. This charming property is a perfect condo alternative offering rare first-floor living. The open layout features a brand-new kitchen with polished quartz countertops, two bedrooms, and a beautifully renovated full bath. The second bedroom includes in-unit laundry for added convenience. Step out to a

    Elizabeth Ferrara Cottage Hill Real Estate

    88 Grand View Ave, Winthrop, MA 02152
  • 247 Washington Ave Unit 9, Winthrop, MA 02152
    247 Washington Ave Unit 9, Winthrop, MA 02152
    247 Washington Ave Unit 9, Winthrop, MA 02152
    /24

    $520,000

    • 2 Beds
    • 2 Baths
    • 1,116 Sq Ft

    247 Washington Ave Unit 9, Winthrop, MA 02152

    Beautiful corner end-unit condominium in the desirable Nautilus Building offering panoramic views of Boston, the marina, Winthrop Yacht Club, and Elks from every room. This spacious 2-bedroom, 2-bathroom condominium features a private balcony that spans the entire length of the unit, perfect for relaxing and watching the boats go by. Inside this bright and airy unit, is a white kitchen, hardwood

    Erica Gore Century 21 Seaport

    247 Washington Ave Unit 9, Winthrop, MA 02152
  • 19 Banks St, Winthrop, MA 02152
    19 Banks St, Winthrop, MA 02152
    19 Banks St, Winthrop, MA 02152
    /29

    $735,000 Open Sat 11:30AM - 12:30PM

    • 3 Beds
    • 1 Bath
    • 1,269 Sq Ft

    19 Banks St, Winthrop, MA 02152

    Price improvement! 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

    Susan Doig Charlesgate Realty Group, llc

    19 Banks St, Winthrop, MA 02152
  • 60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, Winthrop, MA 02152
    60 Waldemar Ave, 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
  • 10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    10 Somerset Ave Unit 405, Winthrop, MA 02152
    /29

    $551,633 Open Sat 12:30PM - 1:30PM

    • 1 Bed
    • 1 Bath
    • 683 Sq Ft

    10 Somerset Ave Unit 405, 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 405, Winthrop, MA 02152
  • 993 Shirley St, Winthrop, MA 02152
    993 Shirley St, Winthrop, MA 02152
    993 Shirley St, Winthrop, MA 02152
    /23

    $839,000

    • 6 Beds
    • 3 Baths
    • 2,184 Sq Ft

    993 Shirley St, Winthrop, MA 02152

    Located near Yirrell Beach, this updated single-family home is ready for its next chapter. Inside, you’ll find an open-concept layout with gorgeous hardwood floors that flow throughout. The modern kitchen is a standout, complete with a shiplap ceiling, granite countertops, and stainless-steel appliances-perfect for daily living and entertaining. The first floor offers one bedroom and a versatile

    Leighann Eruzione Lantern Residential

    993 Shirley 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
  • 35 Somerset Ave Unit 5, Winthrop, MA 02152
    35 Somerset Ave Unit 5, Winthrop, MA 02152
    35 Somerset Ave Unit 5, Winthrop, MA 02152
    /21

    $599,000

    • 2 Beds
    • 2 Baths
    • 969 Sq Ft

    35 Somerset Ave Unit 5, Winthrop, MA 02152

    Welcome to 35 Somerset #5 in Winthrop! This stylish 2-bed 2-bath condo offers 969 square feet of well-designed living space. With two private outdoor areas, including a rare rooftop deck, this home is absolutely perfect for enjoying the warmer months ahead. This home offers an open layout, hardwood floors, and high end finishes including updated lighting, modern bathroom fixtures, and a

    Danielle DeGrazia Choose Boston, LLC

    35 Somerset Ave Unit 5, Winthrop, MA 02152
  • 136 Locust Way, Winthrop, MA 02152
    136 Locust Way, Winthrop, MA 02152
    136 Locust Way, Winthrop, MA 02152
    /14

    $654,900

    • 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
  • 162 Shirley St Unit 164, Winthrop, MA 02152
    162 Shirley St Unit 164, Winthrop, MA 02152
    162 Shirley St Unit 164, Winthrop, MA 02152
    /25

    $699,000 Open Sat 11AM - 12PM

    • 3 Beds
    • 2 Baths
    • 1,413 Sq Ft

    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
  • 80 Shirley St, Winthrop, MA 02152
    80 Shirley St, Winthrop, MA 02152
    80 Shirley St, Winthrop, MA 02152
    /29

    $1,100,000

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

    80 Shirley St, Winthrop, MA 02152

    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 kitchens and natural light

    Nick Burnes Red Tree Real Estate

    80 Shirley St, 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

    $649,900

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

    80 Shirley St Unit 2, Winthrop, MA 02152

    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 kitchen and natural light

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 2, Winthrop, MA 02152
  • 80 Shirley St Unit 1, Winthrop, MA 02152
    80 Shirley St Unit 1, Winthrop, MA 02152
    80 Shirley St Unit 1, Winthrop, MA 02152
    /29

    $449,900

    • 1 Bed
    • 1 Bath
    • 836 Sq Ft

    80 Shirley St Unit 1, Winthrop, MA 02152

    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 kitchen and natural light

    Nick Burnes Red Tree Real Estate

    80 Shirley St Unit 1, Winthrop, MA 02152
  • 115 Almont St, Winthrop, MA 02152
    115 Almont St, Winthrop, MA 02152
    115 Almont St, Winthrop, MA 02152
    /37

    $995,500 Open Sat 10AM - 11:30AM

    • 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
  • 600 Shirley St Unit 16, Winthrop, MA 02152
    600 Shirley St Unit 16, Winthrop, MA 02152
    600 Shirley St Unit 16, Winthrop, MA 02152
    /26

    $525,000

    • 2 Beds
    • 2 Baths
    • 865 Sq Ft

    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
  • 138 Grand View Ave, Winthrop, MA 02152
    138 Grand View Ave, Winthrop, MA 02152
    138 Grand View Ave, Winthrop, MA 02152
    /21

    $721,000

    • 3 Beds
    • 1.5 Baths
    • 1,792 Sq Ft

    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
  • 600 Shirley St Unit 1, Winthrop, MA 02152
    600 Shirley St Unit 1, Winthrop, MA 02152
    600 Shirley St Unit 1, Winthrop, MA 02152
    /31

    $415,000 Open Sat 11AM - 12:30PM

    • 1 Bed
    • 2 Baths
    • 604 Sq Ft

    600 Shirley St Unit 1, Winthrop, MA 02152

    WATER VIEWS & PRIVATE DECK! Welcome to The Cove at 600, a premier condominium development in Winthrop, situated on the historic site of the Crystal Cove Hotel. This meticulously renovated first-floor unit features 1 bedroom and 2 baths, epitomizing perfect beach town living. Every detail has been updated finishes, including newer kitchen & bathrooms. Your living room offers stunning water views,

    The Movement Group Compass

    600 Shirley St Unit 1, Winthrop, MA 02152
  • 43 Loring Rd, Winthrop, MA 02152
    43 Loring Rd, Winthrop, MA 02152
    43 Loring Rd, Winthrop, MA 02152
    /42

    $949,000

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    43 Loring Rd, Winthrop, MA 02152

    Welcome to this spacious center-entrance home in the highly desirable Maze neighborhood of Winthrop, 02152. This three-bedroom, one-and-a-half-bath home is brimming with charm, featuring beautiful original woodwork and a fantastic layout that offers plenty of space to entertain or simply stretch out and relax.Inside, you’ll find a traditional dining room, a cozy fireplace, and a lower-level

    Nicole Bettano Lantern Residential

    43 Loring Rd, Winthrop, MA 02152

Showing Results 1 - 40, Page 1 of 2

Massachusetts Winthrop Winthrop High School

Real Estate & Homes for Sale near Winthrop High School

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group