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$700,000
3 Beds 3 Baths NEW Status 73556640 MLS 1,510 SqFt.
Luxury living with downtown Boston just a few Train stops away! Escape the hustle and bustle of the city and enjoy the best of coastal living, with the beach right down the street. Step inside to a spacious mudroom that opens to a stunning open-concept kitchen—perfect for entertaining. Gleaming hardwood floors, granite countertops, and sun-drenched windows create a warm and inviting atmosphere throughout. With three beautifully finished levels of living space, there is plenty of room to spread out and make yourself at home. At the very top of the home, the charming widow’s peak offers the perfect opportunity to create your own private reading nook—one that would make any book club jealous! The private, fully fenced yard is ideal for relaxing, entertaining, or gathering around a fire after a day at the beach. Completely renovated in 2019, this beautiful home is ready for its new owner. Come join us for the first showing at the open houses this weekend August 1st and 2nd from 10:30-Noon

189 Shirley Unit 2, Winthrop

$849,900
5 Beds 3 Baths NEW Status 73556586 MLS 2,437 SqFt.
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 room currently used as a home office. Upstairs, you'll find three spacious bedrooms, a cozy sitting area, and a full bath. A porch roof patio over looking the ocean is a favorite spot to appreciate the views while you sit back and reflect on your day. A perfect ADU or in-law space in the finished lower level with a oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, with a laundry area, along with a bedroom with a full sized cedar closet. Right out your lower door is an area to have a table or another sitting area under cover. The outdoor shed has doors that open up to the pergola with a bar and tv so you can watch the games during your cookouts. Enjoy the convenience of three off-street parking spaces and easy access to Boston, Logan Airport, scenic waterfront trails, shopping, dining, and more. Don't miss it!

43 Dolphin Ave, Winthrop

$410,000
2 Beds 1 Baths NEW Status 73555750 MLS 902 SqFt.
Coastal living at its best! Just steps from the beach, this beautifully maintained 2-bedroom, 1-bath condominium offers the perfect blend of charm, comfort, and convenience. The bright, open-concept living and dining area flows seamlessly into a spacious kitchen featuring rich cabinetry, granite countertops, and large penninsula—ideal for entertaining. A sun-filled enclosed porch provides the perfect spot to enjoy your morning coffee or unwind after a day by the ocean. Additional highlights include low condo fees, ample street parking, generous private dry storage in the basement, and a small four-unit association. Whether you're looking for a year-round home, weekend retreat, or investment opportunity, this move-in ready condo offers an unbeatable location just moments from Winthrop's beaches, restaurants, and Boston.

25 Winthrop Shore Drive Unit 1, Winthrop

$2,250,000
16 Beds 6 Baths ACTIVE Status 73554183 MLS 5,553 SqFt.
566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been well maintained and features all new common area lighting and carpeting, the foundation (interior and exterior) has been repointed. The Property has new blown-in insulation, and the rear deck system has been updated with refinished decks and new railings. The Property also has a new 11-camera security system and credit card operated washers and dryers. Two of the units have been fully renovated and two units have renovated bathrooms. The Property is separately metered for a mix of gas & electric powered heat & hot water, as well as electrictity. The Landlord provides town water & sewer.

566 Shirley St, Winthrop

$977,700
3 Beds 3 Baths ACTIVE Status 73552912 MLS 2,451 SqFt.
Location, location, location! Welcome to 211 Grovers Avenue, perfectly situated in the highly sought-after ocean community of Winthrop Highlands. This iconic brick-front Cape Cod sits on a 5,227 sq. ft. lot and radiates timeless character. Inside, you'll find an inviting living room featuring elegant tray ceilings and a warm fireplace. The home offers 3 bedrooms and 2.5 bathrooms, with incredible potential for expansion—the finished basement could easily become a teen suite, family room, or even an income-generating apartment. Outside, enjoy the coastal lifestyle with a great back deck, an attached garage, and a driveway, all just steps from the ocean. PRIVATE SHOWINGS START 8/7 through 8/9 PLEASE TEXT OR EMAIL LISTING AGENT

211 Grovers Ave, Winthrop

$489,900
3 Beds 1 Baths ACTIVE Status 73553580 MLS 1,036 SqFt.
Welcome to 16 Underhill Rd. #3, a beautifully updated 3-bedroom, 1-bath condo offering 1,036 sq. ft. of move-in ready living space. This bright and inviting home features modern updates, a functional layout, and private laundry in the basement for added convenience. Enjoy your own private deck, perfect for relaxing or entertaining. The property also includes a private garage plus ample additional parking—a rare find. Ideally located just moments from the beach, you'll love the convenience of coastal living with easy access to local shops, restaurants, and commuter routes. Whether you're looking for a primary residence or a low-maintenance lifestyle near the ocean, this turnkey condo is ready for its next owner.

16 Underhill St Unit 3, Winthrop

$495,000
2 Beds 2 Baths ACTIVE Status 73550972 MLS 879 SqFt.
This like-new 2-bedroom, 2 bath condo at 34 Underhill Street delivers the finish level of new construction at a fraction of the cost. Gut renovated and converted in 2020, every detail was approached with care, from the white shaker kitchen with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including gas cooking, to the wide plank hardwood floors that run throughout the entire unit. The primary bedroom features a custom walk-in closet with built-in shelving and drawers, and direct access to a full bath. The open living area is bright and generously sized with recessed lighting and mini-split systems for year-round comfort. Ground-floor entry with private access adds convenience rarely found in condo living. Set steps from the Winthrop coastline with the Boston ferry, Rt. 1A, and Logan Airport all just minutes away, this is a turnkey home in a location that continues to attract buyers who want coastal living without sacrificing quality.

34R Underhill St Unit 3, Winthrop

$2,380,000
5 Beds 6 Baths ACTIVE Status 73550891 MLS 6,224 SqFt.
One of the most coveted locations in Winthrop, 174 Bartlett Rd is your dream costal retreat where luxury meets seaside living. Completely gut renovated, this exceptional home offers over 6,000 sq ft of beautifully designed living space across four expansive levels. The heart of the home is the stunning chefs kitchen with seamless oversized Brazilian Quartzite island surrounded by premium Sub-Zero, Wolf & Miele appliances, & a fully appointed entertaining bar. Anchored by a striking Valor fireplace, the two thoughtfully designed seating areas & expansive dining room create space for intimate or larger-scale entertaining. The Primary suite is a water view retreat with steam shower & BainUltra therapeutic soaking tub, dual walk-in closets, & private laundry. Welcome guests in the lower level suite, enjoy resort style yard with Gunite in-ground pool, basketball court & grilling island, or end days on the roof top deck with incredible views. This thoughtfully crafted home is unforgettable!

174 Bartlett Road, Winthrop

$1,260,000
4 Beds 6 Baths ACTIVE Status 73550792 MLS 3,150 SqFt.
Modern living made easy at 21 Hutchinson Street, two family with 3150 SF of living space. Come experience modern finishes in this fully renovated home. Unit 1 offers an easy access layout with first floor main bedroom on-suite bathroom and walking closet. The main area offers a versatile open floor plan with half bathroom and laundry. The second bedroom located in the lower level of this unit to offer full privacy with a sitting area, and generously sized spa bathroom. Unit 2 offers two generously sized bedrooms each with walking closets and on suite bathrooms. The main area features one half bathroom and laundry. New HVAC system offering gas heat and central cooling. Tankless water heaters two thermostat zones for each unit and gas stoves. Outside features 2 car garage, 2 electric car charging stations, new fence, and concrete patio area. All siding, roof, windows, electrical and plumbing are new. Move in Relax and Enjoy your new home in the quaint town of Winthrop!

21 Hutchinson Street, Winthrop

$950,000
3 Beds 3 Baths CONTINGENT Status 73550478 MLS 1,749 SqFt.
OPEN HOUSE CANCELED! Welcome to the Highlands, where coastal living meets modern comfort. This beautifully maintained single-family offers water views, thoughtfully updated living spaces, and the flexibility today's buyers desire. The sun-filled main level features gleaming hardwood floors throughout, an upgraded kitchen, and an open layout that flows seamlessly to the spacious rear deck overlooking the fenced backyard with a private hot tub—perfect for entertaining or relaxing. Upstairs, the spacious primary suite offers a generous walk-in closet, while two additional bedrooms provide comfortable accommodations. The finished lower level provides versatile bonus living space ideal for a family room, home office, gym, or guest suite. Enjoy the best of indoor-outdoor living with inviting spaces designed for both everyday comfort and effortless entertaining. Just moments from the beach, this move-in-ready home combines modern updates, flexible living space, and an exceptional location.

50 Floyd St, Winthrop

$899,900
4 Beds 2 Baths CONTINGENT Status 73550227 MLS 1,590 SqFt.
If you've been waiting for the perfect opportunity to live near the ocean - this is it! Located between Winthrop Harbor and Winthrop Beach, with literal steps to the ocean in either direction, this beautiful, completely renovated single family home offers 4 bedrooms, 2 baths, an updated kitchen, hardwood floors, central air and much more! Great back yard, off-street parking and a beautiful wrap-around front porch with water views that New Englanders dream of. Incredible location - just steps to Winthrop Beach and Winthrop Landing with water ferry access to Downtown Boston. Close to restaurants, parks, shops, multiple yacht clubs, public transportation and much more. Minutes to Boston, Logan Airport and points north. Don't miss this amazing opportunity to find your seaside home this summer.

69 Crystal Cove Avenue, Winthrop

$299,900
1 Beds 1 Baths CONTINGENT Status 73549060 MLS 800 SqFt.
Super affordable top-floor 1-bedroom condo located less than a block from Winthrop Beach! This surprisingly spacious unit features fresh paint, hardwood floors, high ceilings, partial water views, private parking lot and an HOA fee that includes heat and hot water. An excellent opportunity for first-time buyers or anyone looking to enjoy coastal living at an exceptional value for less than most rents in the area. Winthrop offers the perfect blend of coastal charm and city convenience. With beautiful beaches, scenic waterfront walking trails, award winning local restaurants, marinas, and a welcoming small-town atmosphere, it's an ideal place to call home. Located just minutes from downtown Boston and Logan Airport by car, train or ferry, Winthrop provides a relaxed seaside lifestyle without sacrificing easy access to everything the city has to offer.

267 Washington Ave Unit 6, Winthrop

$729,900
4 Beds 2 Baths ACTIVE Status 73548082 MLS 1,586 SqFt.
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 and water views. The main level includes a living room with a fireplace, a formal dining room, and a sunroom that opens to a screened porch. Central air and forced air heat keep the home comfortable year-round. A full basement with sump pump offers storage and utility space, and a paved driveway provides two off-street parking spaces. Ocean views and public beach access nearby. Enjoy the best of coastal living, where the beach is just steps away & commuting to Boston is easy with quick access to the ferry, T stations, Rt. 1A, Logan Airport.

52 Pebble Ave, Winthrop

$899,900
3 Beds 3 Baths ACTIVE Status 73546996 MLS 2,125 SqFt.
PRIDE OF OWNERSHIP CAN BE YOURS.......METICULOUSLY CARED FOR AND READY FOR THE NEW OWNERS! Located in one of Winthrop's most desirable areas, this Center Entrance Colonial has Harwood oak floors and a bath on every level. A huge fireplaced living room, eat in kitchen with a slider and deck overlooking the enormous (pool size) yard with a garden area and lots of off street parking. The second level has 3 bedrooms and a full bath and laundry. The Main bedroom is King-sized! The Bonus Room in the basement is multi purposed with another full bath, exrta high ceilings, open floor plan and a direct walk out to the yard. Another separate basement area is a handy workshop/storage area. THIS COULD BE THE ONE! In Winthrop by the Sea boasting 2 beaches, new schools, 3 Yacht Clubs, a nine hole golf course and lots of Great Restaurants!

37 Loring Rd., Winthrop

$875,000
4 Beds 3 Baths UNDER AGREEMENT Status 73542949 MLS 2,016 SqFt.
Two-family home in a prime Winthrop location, directly across from Ingleside Park and minutes from Winthrop Center. Each unit offers 2 bedrooms, 1 full bath, a bright living room, eat-in kitchen, and private porch. Set on a 0.14-acre lot, the property features a partially fenced backyard—ideal for entertaining, gardening, grilling, or relaxing. The lower level, accessible via a private rear entrance, offers excellent potential for flexible use such as a recreation area, home office, gym, workshop, or storage. Recent updates include a roof replacement in 2021. Just a short stroll to Winthrop Center shops and restaurants, and to Donovan Beach, with bus service connecting to the Blue Line and approximately a 30-minute door-to-door commute to Boston via public transit. Whether you're an owner-occupant looking to live in one unit and offset your mortgage with rental income, or an investor seeking rental income in a desirable coastal location, this is an opportunity you won't want to miss.

126 Brookfield, Winthrop

$994,000
5 Beds 3 Baths UNDER AGREEMENT Status 73541368 MLS 2,564 SqFt.
Experience coastal living at its finest at 156 Locust Street. Just steps from the beach, this beautifully renovated 5-bedroom, 3-bathroom home offers over 2,500 square feet of stylish living space with ocean views and exceptional indoor-outdoor living. Renovated in 2022, the home blends modern luxury with timeless coastal charm. The stunning primary suite provides a private retreat, while a versatile first-floor fifth bedroom offers flexibility as a home office, bonus room, guest space, or playroom. Enjoy central air, sun-filled living spaces, and seamless access to the private fenced backyard and expansive deck, perfect for entertaining or relaxing after a day at the beach. Recent updates include heating systems (2024 & 2025), a hot water heater (2025), and upgraded 200-amp electrical service. Wake up to ocean views from the front balcony and enjoy a turnkey coastal lifestyle in one of Winthrop's most desirable seaside locations.

156 Locust St, Winthrop

$1,499,000
5 Beds 3 Baths ACTIVE Status 73541145 MLS 2,889 SqFt.
Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. The units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture.Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

516 Pleasant St, Winthrop

$939,000
3 Beds 2 Baths ACTIVE Status 73537801 MLS 1,924 SqFt.
NEW PRICE! Fresh Updates! Now Vacant! Exceptional 2-family in desirable Winthrop. Same owner for 20 years! Turnkey opportunity for Investors or Owner-Occupants seeking strong rental income. Great for Multi-Gen living! Both units offer hardwood floors, closets, and spacious Kitchens w/ Pantrys. Windows galore! Gorgeous natural light! Beautifully proportioned rooms, easy floorplans, great storage. Welcoming farmer’s porch, fenced yard, and more! 3 OFF-ST PARKING SPACES. Unit 1 offers 2 BR’s, LR, DR, and huge Kitchen. Upstairs, Unit 2 features 1BR plus a windowed dressing room/WFH office, LR, DR, roomy Kitchen, along with exclusive access to a finished heated attic with 2 sunny bonus rooms ideal for WFH/guests/storage/gym. Unfinished basement with flex space for storage/hobbies. Steps to WINTHROP H.S. Close to parks, beaches, restaurants. Minutes to East Boston, Orient Heights MBTA/Buses, Logan, DT Boston. GPS "Oceanview"

105 Ocean View St., Winthrop

$850,000
5 Beds 3 Baths UNDER AGREEMENT Status 73537768 MLS 3,035 SqFt.
Rare opportunity to own a legal 2 family with an inlaw apartment in one of Winthrop's most desirable locations! Completely vacant and ready for its next owner, this brick-front property offers tremendous potential for investors, owner-occupants, or multigenerational living. No flood insurance required. The spacious owner's unit lives like a single-family home, featuring 7 rooms, 3 bedrooms, a sunroom, office, dining room, deck, and a dramatic sunken living room with fireplace. Additional 2-room apartment & in-law apt provide excellent income potential. Set on a beautiful, generously sized lot with a heated 2-car garage, this property is ready for your vision and updates. Enjoy all that Winthrop has to offer—beautiful beaches, scenic waterfront walks, outstanding restaurants, local shops, and a welcoming small-town atmosphere—just minutes to the MBTA, Logan Airport, Boston, and major routes north and south.

18-20 Fairview Steet, Winthrop

$650,000
3 Beds 2 Baths UNDER AGREEMENT Status 73536296 MLS 800 SqFt.
Beautifully maintained 3-bedroom single-family ranch in desirable Winthrop offering comfortable one-level living plus the bonus of a spacious finished lower level, providing versatile additional rooms for a variety of needs. The main floor features a welcoming living room with fireplace, updated eat-in kitchen, recessed lighting, modern full bath with tile flooring, and three bedrooms with hardwood floors and ceiling fans. The finished basement includes two bonus rooms, a full bath, laundry room, and separate storage area. Abundant closet space provides excellent storage throughout. Enjoy the large backyard and deck, perfect for entertaining, relaxing, or outdoor dining. Potential future ADU possibilities may exist, subject to local zoning and approvals. Conveniently located near beaches, waterfront dining, parks, a local fitness center, and just minutes from Boston, this home offers the best of beach-town living.

496 Winthrop St, Winthrop

$485,000
1 Beds 2 Baths ACTIVE Status 73535636 MLS 591 SqFt.
Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to Boston. Unit features tasteful upgrades, including a custom kitchen marble backsplash, quartz countertop and boasts not one, but two private decks featuring Trex decking. Unit 7 is widely considered the premier residence in the building, featuring the largest private waterfront-facing deck an ideal setting for morning coffee, outdoor dining, or simply taking in the spectacular views. Vinyle double hung windows with thermopane glass. Just in time for summer, this rare offering presents an incredible opportunity to enjoy, waterfront living at its finest.

600 Shirley St Unit 7, Winthrop

$1,480,000
4 Beds 3 Baths ACTIVE Status 73534719 MLS 2,475 SqFt.
Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive improvements throughout. The open-concept layout is filled with natural light and showcases a beautifully appointed kitchen with custom cabinetry, quartz countertops, stainless steel appliances, a beverage refrigerator, and a large center island. Occupying the entire third level, the private primary suite offers breathtaking water views, a private balcony, a walk-in closet, and a spa-inspired bath. A rare opportunity to own a thoughtfully reimagined coastal home where panoramic water views, abundant natural light, and extensive recent reconstruction come together in one exceptional setting.

89R Upland, Winthrop

$385,000
2 Beds 1 Baths ACTIVE Status 73534695 MLS 677 SqFt.
Welcome to coastal living at its best. HOA FEE INCLUDES HEAT & HOT WATER! This top-floor corner 2-bedroom condo offers ocean views & an ideal vantage point overlooking the water, bringing in incredible natural light throughout. Hardwood floors run throughout the living area, while the kitchen features granite countertops, stainless steel appliances, & ample storage. Recent upgrades include appx. $10K in custom built-ins & thoughtfully designed closet systems to maximize storage & functionality throughout the home. The open living & dining space creates an inviting setting for everyday living or entertaining. Both bedrooms offer generous space, while in-unit laundry provides everyday convenience. Enjoy a professionally managed, well-maintained building with many recent improvements such as a new roof & whole building water heater/boiler. Deeded parking, large locked deeded storage unit, two bus lines incl. a stop at the top of the street w/ direct Blue Line access, ferry access, & walkable walkable restaurants complete this ideal coastal lifestyle

53 Trident Ave Unit 301, Winthrop

$1,100,000
5 Beds 4 Baths ACTIVE Status 73534385 MLS 2,949 SqFt.
A rare opportunity to own a 4-unit multi-family investment property in one of Winthrop's most sought-after coastal locations, just minutes from downtown Boston and Logan Airport. This asset offers an ideal mix for investors and owner-occupants alike. The property features one three-bedroom apartment, one two-bedroom apartment, and two studio units. The three-bedroom and one studio apartments are currently leased, and the remaining studio and two-bedroom apartments can be delivered vacant. Three off-street parking spaces come with the property. Set on a 4,075± sq ft lot in a supply-constrained market with strong, year-round rental demand, the property delivers a compelling blend of in-place income and future growth potential through both rent increases and value-addition. Steps to the beach, Winthrop Golf Club, and the heart of Shirley Street, come see everything that this property has to offer.

32 Irwin St, Winthrop

$750,000
4 Beds 3 Baths ACTIVE Status 73534235 MLS 2,700 SqFt.
Steps from the shore, this corner lot offers coastal living w a wide, expansive front porch perfect for catching the harbor breeze or entertaining. This move-in ready home features 2,700 sq.ft. of spacious living and an unbeatable beachside location. The interior boasts hardwood floors throughout most of the home, featuring four bedrooms and 2.5 bathrooms. Additionally, a finished third floor offers a versatile space for a home office or yoga studio, while the finished lower level is perfect for a home gym . The airy first floor features 8' ceilings and a seamless flow between the fireplaced living and dining rooms. The kitchen comes fully equipped with granite countertops, and the upper levels offer bedrooms with select water views. The property includes a driveway and a one-car garage. It is ideally situated just steps from the beach, parks, dining, and the MBTA water shuttle, providing easy access to Boston's Waterfront, the Seaport, and Logan Airport. Minutes into Boston.

546 Shirley St, Winthrop

$4,724,900
10 Beds 15 Baths ACTIVE Status 73531014 MLS 9,156 SqFt.
Rooted in history & reimagined with intention, The Pearl is a one-of-a-kind five-unit multifamily property by the coast in Winthrop. Formerly a church, the building has been thoughtfully transformed into five distinct loft-style residences, each with its own layout, character & design identity. Original architectural details including exposed beams, hardwood floors, oversized windows & dramatic ceiling heights are balanced with modern finishes throughout. Each residence features Bosch appliances, electric fireplaces, in-unit laundry, radiant heated primary baths, walk-in closets, hidden powder rooms, concealed storage, private outdoor space with automated retractable awnings, additional storage & two off-street parking spaces. Located near Winthrop’s beaches, harbor walks, cafés, restaurants & commuter access into Boston, The Pearl offers a special opportunity to own a boutique coastal multifamily with historic character, strong design & flexible long-term potential.

1001 Shirley St, Winthrop

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