17

Winthrop, MA Homes for Sale under $1,000,000

Section Image
  • /37

    $829,900

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,437 Sq Ft

    43 Dolphin Ave, Winthrop, MA 02152

    Welcome to 43 Dolphin Ave, a charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile

    Patricia Nunez Redfin Corp.

    43 Dolphin Ave, Winthrop, MA 02152
  • /41

    $799,986

    $30K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,560 Sq Ft

    50 Main St, Winthrop, MA 02152

    Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience

    Matt Tasgin United Brokers

    50 Main St, Winthrop, MA 02152
  • /42

    $859,900

    • 2 Beds
    • 1.5 Baths
    • 1,674 Sq Ft

    3 Seal Harbor Rd Unit 336, Winthrop, MA 02152

    A rare offering at the prestigious Seal Harbor III, this exceptional corner residence captures breathtaking panoramic water views from an expansive, light filled interior and a private balcony - perfect for enjoying morning coffee, evening sunsets, or simply taking in the every changing waterfront scenery. Completely reimagined with a full gut reno in 2010, the home showcases timeless design, an

    Cathie Curran Charlesgate Realty Group, llc

    3 Seal Harbor Rd Unit 336, Winthrop, MA 02152
  • /42

    $765,000

    Open Sun 12PM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 1,933 Sq Ft

    546 Shirley St, Winthrop, MA 02152

    This is your opportunity to own in beautiful Winthrop by the Sea at an incredible value! This spacious 4+ bedroom, 2.5-bath home offers the perfect blend of character, updates, and an unbeatable location. Relax on warm summer evenings from the inviting wraparound porch, or take a short stroll just one block to Winthrop Beach for sunrise walks and ocean breezes. Inside, you'll find oversized

    Christine D'Ambrosio Bowdoin Real Estate Partners

    546 Shirley St, Winthrop, MA 02152
  • /35

    $758,000

    $6K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    189 Shirley St Unit 1, Winthrop, MA 02152

    Welcome to coastal living at its finest in this truly unique and beautifully appointed townhome residence. Spanning three expansive levels, this exceptional three-bedroom, two-and-a-half-bath home seamlessly blends comfort, style, and privacy in the one and only seaside community of Winthrop 02152. Privately situated with its own separate entrance, this rare offering lives like a single-family

    Tammy Merk Lantern Residential

    189 Shirley St Unit 1, Winthrop, MA 02152
  • /22

    $865,000

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

    1001 Shirley St Unit 2, Winthrop, MA 02152

    Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy

    Vincenzo Caraglia Sciaraffa Real Estate, LLC

    1001 Shirley St Unit 2, Winthrop, MA 02152
  • /23

    $975,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    200 Main St Unit 1, Winthrop, MA 02152

    Brand-new construction in the heart of Winthrop, offering a rare opportunity to own a thoughtfully designed new-build townhome in a coastal setting just outside of the city. As construction progresses, buyers may have the opportunity to personalize select interior finishes, making this home uniquely their own. Spanning approximately 2,100 square feet across two levels, the home features an

    Reserve Team Reference Real Estate

    200 Main St Unit 1, Winthrop, MA 02152
  • /37

    $849,900

    Open Sat 12PM - 1:30PM $100K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,843 Sq Ft

    7 Willis Ave, Winthrop, MA 02152

    Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms & 2 bed.Kitchen has Induction Stove Top Granite Island & Counter Tops.Stainless Steel Induction Wall Microwave & Wall Oven.Top of the line Stainless Steel Refrigerator & Dishwasher.Granite tile floor. Plenty of Cabinet Space. Beautiful Tiger Hardwood Floors & Natural Woodwork Throughout. Crown

    Philip Consolo Century 21 North East

    7 Willis Ave, Winthrop, MA 02152
  • /27

    $710,000

    • 4 Beds
    • 2 Baths
    • 1,193 Sq Ft

    542 Shirley St, Winthrop, MA 02152

    The perfect blend of comfort, convenience, and affordability! Whether you’re a first-time homebuyer, looking to downsize, or searching for an alternative to condo living, this charming 4-bedroom home offers the space you need with the low-maintenance lifestyle you want all just one block from the beach. The main level features a comfortable bedroom and full bathroom with a convenient walk-in

    Christine D'Ambrosio Bowdoin Real Estate Partners

    542 Shirley St, Winthrop, MA 02152
  • /30

    $799,999

    $30K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,000 Sq Ft

    876 Shirley St Unit 1, Winthrop, MA 02152

    Direct Ocean 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 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
  • /42

    $999,888

    $199K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,635 Sq Ft

    66 Sunnyside Ave, Winthrop, MA 02152

    NEWLY PRICED! PRICED TO SELL! Rare waterfront two-family in Winthrop's sought-after Cottage Park neighborhood, offering stunning views of the Bay, Harbor, marsh, and ocean, a lifestyle feature you simply can't replicate at this price point. Built in 1920, this classic 2,635 sq ft two-story home sits on a 5,227 sq ft lot just steps from the beach. A perfect opportunity for first-time buyers or

    Mirna Monterrosa Orellana COM-PRO Real Estate Services, Inc

    66 Sunnyside Ave, Winthrop, MA 02152
  • /39

    $998,900

    • 6 Beds
    • 2.5 Baths
    • 3,263 Sq Ft

    217 Pleasant St, Winthrop, MA 02152

    Open House This Weekend! Sunday 8/30/26 12:00-1:30pm A fantastic value for this home. Its an opportunity to make it your own. Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces

    Louis Bonavita Benton Real Estate Company

    217 Pleasant St, Winthrop, MA 02152
  • /21

    $939,900

    $39K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,371 Sq Ft

    43 Loring Rd, Winthrop, MA 02152

    Single Home, Great Location Great Shape Ready to Move In.

    Jason Saphire www.HomeZu.com

    43 Loring Rd, Winthrop, MA 02152
  • /25

    $840,000

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,837 Sq Ft

    27 Billows St, Winthrop, MA 02152

    This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a

    Reserve Team Reference Real Estate

    27 Billows St, Winthrop, MA 02152
  • /9

    $780,000

    $20K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,000 Sq Ft

    120 Hermon St, Winthrop, MA 02152

    Ingleside Park 2-unit with a rare 10,000sqft oversized lot owned by the same family for over 20 years. Bring your ideas to transform this property into your dream investment or income-producing home with the untouched backyard begging to become either an outdoor oasis, additional parking, or more. Featuring off-street parking for 2 or 3 cars with the first floor unit offering two bedrooms, one

    Steve Binder Binder Residential

    120 Hermon St, Winthrop, MA 02152
  • /24

    $725,000

    • 2 Beds
    • 2 Baths
    • 1,113 Sq Ft

    140 Shirley St Unit 250, Winthrop, MA 02152

    Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This two-bedroom, two-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 Team Compass

    140 Shirley St Unit 250, Winthrop, MA 02152
  • /21

    $715,000

    $15K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,586 Sq Ft

    52 Pebble Ave, Winthrop, MA 02152

    Cape-style home in Point Shirley, steps from the beach and within Winthrop's most walkable stretch of coastline. Built in 1900 and updated with a remodeled kitchen featuring granite counters and recessed lighting, plus a remodeled full bath with a tiled tub and shower. Original hardwood floors run through the main level and all four bedrooms, paired with bay windows that bring in natural light

    Reserve Team Reference Real Estate

    52 Pebble Ave, Winthrop, MA 02152
How to Buy a Home How to Finance a Home How to Sell a Home