Waterfront Homes for Sale in Winthrop, MA

Rare opportunity just one street from the beach, offering strong rental income potential ideal for investors and owner-occupants alike. This well-maintained two-family offers a flexible layout with a 2-bedroom 1st floor unit and a spacious second unit with 3 bedrooms & 1.5 baths across two levels. The second unit is currently rented for $3,650/month, providing immediate income, while the 1st

Mission Impossible Team United Brokers

Winthrop is one of the last undervalued waterfront towns in Greater Boston, and opportunities like this don't sit long. 11 Pearl Ave is a vacant 3-family just a block from the ocean, generating $10,500/month at market rents with zero displacement headaches. Three floors, 11 bedrooms total, 4,032 sq ft of income-producing space on a town where the average days on market keeps shrinking. 3 separate

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Attention Investors and Contractors – Prime Opportunity! Four-bedroom home with a third-floor in-law suite ready for its next chapter. Set on a charming tree-lined street, this property offers a solid footprint for renovation along with a detached garage and manageable yard space. Vacant and being sold as-is, this home will require a full rehab. Ideal for investors or owner-occupants looking to

Leighann Eruzione Lantern Residential

Corner-positioned harborfront residence at Nautilus Condominiums with unobstructed Boston skyline and water views from every room. This 2-bedroom, 2-bath home spans 1,100+ sq ft and benefits from a south-to-west exposure, delivering consistent natural light throughout the day. A private balcony is set directly over the harbor, extending the living space outward. The layout balances openness and

Federico Creatini eXp Realty

Wonderful opportunity to own a coastal Winthrop home with tremendous potential. A welcoming mudroom opens to a spacious foyer and a large living and dining area with great flow for everyday living. A bonus front room offers flexible space for a home office, playroom, or an expanded open-concept layout. The kitchen leads directly to the back deck for warm-weather entertaining. Upstairs features

Elizabeth Ferrara Cottage Hill Real Estate

Street-Level Coastal Condo with Sweeping Views! Welcome to The Condos at 51 Harborview. This street-level condo offers easy access with sweeping harbor and city skyline views. The home features two bedrooms, one bath, and a modern kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl flooring.Relax or entertain on the front porch, deck off the

Susan Doig Donnelly + Co.

1080 Shirley St presents a rare two-family property with two separate structures, offering exceptional flexibility for owner-occupants or investors seeking strong rental potential. Ideally located just steps from the ocean in Winthrop, the property enjoys beautiful water views and a true coastal setting. The front unit features a spacious sunroom that fills the home with natural light, along with

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Special Financing Available (30yr Fixed @ 4.25%) on this project for some buyers. 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, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style

Kovacs Savage Team Byrnes Real Estate Group LLC

Welcome to Unit 207 at The Somerset—Winthrop’s boutique condo community, where coastal living meets modern design. This spacious 2-bedroom, 1-bath home features an open-concept living and dining area, a well-appointed kitchen with quartz countertops and stainless steel appliances, central A/C, and modern finishes throughout, plus access to a fitness room, elevator, and resident lounge for added

Charlesgate New Development Team Charlesgate Realty Group, llc

Saturday open house cancelled due to weather! This well-maintained 3-bedroom, 2-bath home offers comfortable living in a prime Winthrop location. The freshly painted interior features large, well-proportioned rooms throughout. A fully finished lower level adds valuable living space, while the converted garage provides a unique bar and entertainment area. The private, fully fenced patio is perfect

Bridget Conroy Coldwell Banker Realty - Milton

LAST STUDIO! 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.

Charlesgate New Development Team Charlesgate Realty Group, llc

Half a block from Winthrop Beach, this spacious 2-bedroom first-floor condo offers over 1,300 square feet of character-filled coastal living in a classic 1890 three-family home. From the moment you enter, you’ll appreciate the welcoming foyer and period details, including Chelsea-tiled fireplaces, high ceilings, and hardwood floors throughout the main living areas. A formal living room and a

Clara Arroyave eXp Realty

$6,000 closing cost credit to buyer!!! 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

The Movement Group Compass

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

Special Financing Available (30yr Fixed @ 4.25%) on this project for some buyers. 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

Kovacs Savage Team Byrnes Real Estate Group LLC

Situated just steps from the sand, 304 Shirley presents a rare opportunity to own a fully occupied 6-unit building in one of Winthrop's most desirable seaside neighborhoods. Each unit is a well-maintained 1-bedroom, offering consistent rental income and strong tenant demand. This beachside property is perfectly positioned near local shops, restaurants, and public transportation, making it a

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Welcome to Unit 5 at The Pearl, a boutique coastal residence at 1001 Shirley Street, where refined design meets oceanfront living. This thoughtfully crafted home offers sweeping Atlantic views and a private ocean facing balcony, creating a daily connection to the water that few properties can match. Inside, the space is defined by clean architectural lines, generous ceiling height, and a layout

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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. Featuring beautiful cherry hard wood floors, Family room, Formal dining room, ( Living room-could be master

Jim Iannuzzi Amo Realty - Boston City Properties

Harborview Condo with Sweeping ViewsWelcome to The Condos at 51 Harborview. This beautifully renovated condo is perched high on the hill with stunning harbor and city skyline views. Unit 1 features two bedrooms and one bath, including a spacious primary with walk-in closet, and a brand-new kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl

Susan Doig Donnelly + Co.

Special Financing Available (30yr Fixed @ 5.75% No PMI). 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.

Kovacs Savage Team Byrnes Real Estate Group LLC

Introducing coastal living in this luxurious two-family home set on one of Winthrop’s most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat.

Jessica Pumphret Blue Sky Realty

Penthouse Condo with Harbor Views!Welcome to The Condos at 51 Harborview. This penthouse residence offers sweeping harbor and city skyline views from atop the hill. Unit 3 features two bedrooms, one bath, and a modern kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl flooring.Enjoy a harbor-facing deck, private yard, and one deeded off-street

Susan Doig Donnelly + Co.

811 sq. ft. 2-bedroom, 1-bath condo located less than a mile from the beach. The layout features a large primary bedroom with a spacious walk-in closet and a functional second bedroom. Building amenities include an in-ground pool, gym, sauna, and tennis courts. This unit comes with two off-street parking spaces. Conveniently situated near local shops, public schools, and transportation. A

Ardian Ramadani Keller Williams Realty Boston-Metro | Back Bay

Built in 2023 and still feeling brand new — this 3-bedroom stunner puts you steps from the beach and minutes to Downtown Boston. Sunlight pours across hardwood floors, while the sleek kitchen with white shaker cabinets and high-end appliances anchors the open layout. Central air keeps things comfortable year-round, and deeded off-street parking seals the deal. Coastal living without sacrificing

Adam Mundt Kingston Real Estate & Management

Welcome to Unit 405 at The Somerset, Winthrop’s premier boutique condo community, where coastal charm meets modern design. This bright, open 1-bedroom, 1-bath home features a spacious living and dining area perfect for relaxing or entertaining. The kitchen blends style and functionality with quartz countertops and stainless steel appliances. Enjoy a pet-friendly building, a fitness studio,

Charlesgate New Development Team Charlesgate Realty Group, llc

Welcome to Unit 308 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed 1 + bedroom 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

Charlesgate New Development Team Charlesgate Realty Group, llc

Don’t miss the chance to own this well-maintained 2-bedroom, third-floor condo in Winthrop, Massachusetts. Enjoy being just steps from the ocean while staying only minutes from Boston, a perfect mix of seaside living and city convenience. The unit features an open floor plan with hardwood floors throughout and great natural light. The spacious primary bedroom includes its own private balcony,

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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

WELCOME TO WINTHROP BY THE SEA! THE COVE AT 600 SHIRLEY WAS CONVERTED IN 2022 AND IS LOCATED ON THE SITE OF THE HISTORIC CRYSTAL COVE HOTEL AND HAS AMAZING VIEWS OF BOSTON AND THE ATLANTIC OCEAN! WALK TO THE BEACH, THE YACHT CLUB, VARIOUS RESTAURANTS AND PARKS. THIS 1 BEDROOM UNIT FEATURES NOT ONE BUT TWO BATHROOMS AND 2 DEEDED PARKING SPOTS. ENJOY YOUR IN UNIT LAUNDRY AND EXCLUSIVE REAR PATIO ON

Peggy Pratt Century 21 North East

This move in unit is waiting for you! Unit 210 has an unobstructed view of the ocean and the town of Nahant. as well as a long expanse of lawn and the gazebo. Enjoy your beautiful fully applianced custom kitchen with granite counters and stainless steel appliances , in unit laundry and full bath The hardwood floors throughout add to the value of this condo and the open floor living room/dining

James Lonergan Lonergan Real Estate

Recently reduced and priced to sell! Sun-filled 1BR condo with 900+ sq ft, updated flooring, new appliances, central A/C, private basement space & parking. Prime Winthrop location near beaches, dining & Boston. Ideal for buyers or investors. Don’t miss it!

Esmerlyn Diaz eXp Realty

Stop renting, start owning your slice of the coast! Welcome to The Cove at 600 Shirley Street in Winthrop! This charming studio offers stunning, unobstructed ocean views from your own private deck, perfect for enjoying morning coffee or evening sunsets. Inside, you’ll find warm wood flooring throughout and an updated kitchen with space for a dining table, creating both functionality and comfort.

Christine Goldstein Lyv Realty

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

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Waterfront stunning ocean views from this corner unit with breathtaking sunrises and sunsets. This bright and relaxing 1,005 square foot residence has been lovingly enjoyed by the same owner for 25 years. Spacious living room opened to separate dining room. One bedroom, full bath & generous walk-in closet. Captivating views of the ocean, beach, and boats passing by. Private balcony and

Peggie Gilbert Coldwell Banker Peggy Carter Team

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

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