Single Family Homes for Sale in Winthrop, MA

Home for Sale

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 bath and sweeping coastal vistas. The fully finished lower level is one of only ten legal Airbnbs in Winthrop, offering exceptional income potential, or use it as an ideal in-law or au pair suite with its family room, bonus room, full bath, and laundry. Parking is effortless with two off-street spots and additional front potential. Low, transferable flood insurance at $1,138.00. Embrace waterfront living at its best.

Home for Sale

Welcome to the Highlands, Winthrop?s most coveted neighborhood where modern design meets sweeping Boston views. This renovated home rises high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main level offers an open layout with a living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area that opens to a skyline deck. A first-floor bedroom, full bath, and mudroom add versatility. Upstairs features three bedrooms, including a luxe primary suite with Juliet balcony, walk-in closet, and a spa bath with steam shower, soaking tub, heated floors, and double vanity. The lower level provides a complete one-bedroom living space with its own kitchen, laundry, French doors to the yard, and private entrance ideal for multi-generational living, an au pair, or added flexibility. With a tiered backyard and three-car parking, this home blends sophistication, versatility and unmatched city views.

Home for Sale

Located in one of the most desirable neighborhoods in town, this grand home has been the home to 4 generations of the same family since it was built. It has been cherished by the same family for over 100 years. Rich original woodwork and timeless character can be found throughout. Step into the sun-filled enclosed front porch before entering the impressive foyer featuring a stunning quarter-sawn oak staircase. The spacious kitchen offers endless potential for renovation and customization. The second floor features a generous landing, 5 large bedrooms, and a three-quarter bath. The third floor offers three additional spacious rooms plus a bonus area leading to a loft space, providing flexibility for extended living, office, or creative use. Situated on a corner lot with ample backyard space, this property is a rare opportunity to restore and personalize a truly special home.

Home for Sale

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 renovate and personalize a property to their own style. A great opportunity to transform a well-located property and bring new life to a classic home.

Home for Sale

Welcome to 62 Cottage Ave, a charming Colonial-style single-family home located in Winthrop?s highly desirable Cottage Hill neighborhood. The first floor features an open-concept layout with a spacious, updated kitchen showcasing quartz countertops, stainless steel appliances, and ample cabinetry. Also on the main level are a full bathroom, living room and a bedroom with a walk-in closet.Second floor consists of 1 full bathroom along with 4 bedrooms. Hardwood floors run throughout the home, complemented by tile flooring in the kitchen and bathrooms.Gas heat. Step outside to a private, fenced backyard, perfect for entertaining, family gatherings, or relaxing outdoors.Ideally situated just steps from the beach, local restaurants, the Boston Ferry, and the yacht club, this home offers the perfect blend of coastal living and convenience. A must-see! Open house dates coming soon!

Home for Sale

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 two bedrooms, a smaller third bedroom, and a full bath. The lower level includes an opportunity to finish basement offering generous bonus space ideal for a family room, guest suite, gym, or creative studio. A small fenced-in backyard below the deck provides room for pets, gardening, or flexible outdoor use. Steps to the beach, coffee shops, restaurants, and public transportation, this home is sold as-is and ready for its next owner to bring their vision to life with meaningful long-term investment potential.

Home for Sale

Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you?ll find newer flooring, fresh interior paint, updated lighting, and a beautifully remodeled kitchen complete with stainless steel appliances. The home also features an updated bathroom, newer windows, and exterior doors throughout. The first floor boasts an open and versatile layout with a modern kitchen, spacious living and dining areas, and a bedroom currently being used a home office?all enhanced by water views. Upstairs, you?ll find two well-appointed bedrooms and a full bathroom. Conveniently located near public transportation, including bus routes with direct access to the MBTA.

Home for Sale

A rare opportunity to create your ideal home in a highly desirable Winthrop location. Offering strong bones, generous living space, and beautiful sunset views, this property is the perfect canvas to add personal style and value. Ideally situated just steps from Winthrop Shore Drive, Winthrop Yacht Club, local restaurants, ice cream shops, Winthrop Golf Club, the High School, and July 4th fireworks in every direction. West-northwest roof views are stunning. While 33 Dolphin requires cosmetic updates and is BEING SOLD STRICTLY AS IS, its location in a well-maintained neighborhood offers exceptional potential. The first floor features a wraparound screened porch, foyer, spacious living and dining rooms, kitchen with deck access, pantry, and ? bath. The second floor offers three bedrooms with hardwood floors and walk-in closets, plus a full bath. The third floor includes beamed ceilings, loft area, walk-in closet, and roof access for sweeping views.

Home for Sale

A rare opportunity in one of Winthrop's most sought-after waterfront locations. Ideally set on an expansive lot directly across from the water, this property offers beautiful views from multiple rooms and a setting that truly is hard to replicate. The home is comfortable and livable as-is, while offering exceptional potential to renovate or reimagine into a custom coastal retreat. Whether you're planning thoughtful updates or a full transformation this is a unique chance to secure both location and land in a premier seaside neighborhood. Bring your vision and unlock the full potential of this remarkable coastal property. Estate Sale - being sold strictly as-is. Refrigerator, Washer, & Dryer are being left as gifts!

Home for Sale

Offered for the first time in over 60 years, this meticulously maintained 3-bedroom, 2 full bath home sits on a private corner lot in Winthrop's coveted Point Shirley neighborhood. The main level offers two distinct living areas, a fireplace, eat-in kitchen, a full bathroom and a bedroom or home office. Featuring two spacious bedrooms, the upper level also provides a generous walk-in closet, a second full bath and glimpses of the ocean and Boston Harbor from three windows. The walk-out lower level includes a spacious family room or guest area with two closets, plus utility, storage, laundry area and extra space for a future third bath. Move-in ready with a brand-new retaining wall and expanded driveway. Short distance from Yirrell Beach, Deer Island trails and Coughlin Park - with stunning sunsets and the Boston skyline.?Commuters will value easy access to public transit, Logan Airport and downtown Boston.

Home for Sale

Handymen, fixers and flippers! Beachside location! Less than 100 yards to the beach. This 4-5 Bedroom single will need a total renovation but all the potential is here! There is a yard, off street parking, a garage, and a gas FHW boiler. The home is habitable. Flood insurance is required.

Home for Sale

Want to live in Winthrop?s Highlands area? This beautifully renovated 3-BR, 2-Bath home offers the perfect blend of coastal charm and modern upgrades, featuring 2 car parking, water views, hardwood and porcelain tile floors. NO flood insurance required. A recent front room addition with sunset deck enhances both living space and the home?s connection to its surroundings. Chef?s kitchen featuring a Wolf 6-burner stove, built-in microwave, Sub-Zero refrigerator, beverage center, custom cabinetry. A large center island with abundant cabinet space makes this a true focal point of the home. Enjoy ocean views and a short walk to the beach. The outdoor space has been thoughtfully landscaped featuring flower beds in the front and side, vegetable beds, and a beautifully finished backyard with raised beds, perennials, fire pit, water fountain and an all-stone design creating a peaceful, Zen-like setting. Additional generous storage in the basement with potential for future extra living space.

Home for Sale

Come experience coastal living at its finest in vibrant Winthrop?just minutes from Boston! This seaside single-family home is ideally located just steps from picturesque Winthrop Beach & has been thoughtfully updated for modern living. At the heart of the home is a stunning white quartz kitchen, fully equipped with SS appliances, vent hood, & rich espresso hardwood floors, creating a clean, contemporary aesthetic. The open-concept design flows effortlessly from the radiant-heated entryway into an expansive living room, a bright dining area, & a convenient half bath. French doors lead to a spacious deck overlooking a fenced-in yard?complete with an outdoor shower, perfect for relaxed summer days. Upstairs, you?ll find 3 well-proportioned bedrooms with ample closet space, including a primary walk-in closet, along with a dedicated laundry room & a beautifully renovated oversized bathroom featuring double sinks. Enjoy restaurants, shops, oceanside recreation..your coastal lifestyle awaits!

Home for Sale

Stunning 6-bedroom, 3 full bath single-family home with a private in-law suite offering its own separate entrance and laundry ideal for extended family or additional income potential. Set on a corner lot, this home includes an additional parcel at 16 Elmwood Ave (separate address), adding exceptional value and opportunity. Enjoy beautiful water views from the charming front porch and the primary bedroom. Three finished levels provide flexible living space to fit a variety of needs. The beautifully renovated chef?s kitchen is the centerpiece, showcasing a massive island with seating, coffee bar, and a customized pantry. Opening to a dining area and a warm, inviting living room with fireplace. A fenced backyard and abundant parking complete this rare coastal offering combining seaside serenity with effortless access to Boston.

Home for Sale

Set on a highly desirable corner lot at Sargent & Johnson Ave, this truly one of a kind home offers exceptional space and versatility. Welcoming foyer opens to a spacious living room, while the dining room features a covered porch with ocean views perfect for enjoying sunset evenings. The first floor also includes a bedroom and full bath, plus a kitchen with direct access to the backyard and one of two driveways. Just off the kitchen, a stunning glass walled sitting room overlooks the home?s standout feature: a large 40K gallon indoor in-ground pool. Additional highlights include a generous garage with expansion potential above. Second floor offers multiple baths, including a primary suite with private bath. The third floor functions well as an in-law suite with its own bedroom, full bath, and living area. Previously operated as a successful legal bed and breakfast, this property presents endless possibilities. Updates include roof 2023, newer pool liner. Perfect opportunity for ADU.

Home for Sale

Introducing 24 FAIRVIEW STREET - a charming 4-bedroom, 1.5 bath Victorian in a prime, central location offering inside and outside enjoyment . This beautiful home has been enjoyed and maintained by the same family for many years and offers timeless appeal throughout. First floor has a family room, living room with a fireplace, modern kitchen with s/s appliances, separate dining area and a butler's pantry leading to a formal dining room. There are two separate staircases leading to the second floor. The sun filled landing has four bedrooms off of it including a spacious main bedroom with two closets, a full tiled bathroom and a conveniently located laundry room with storage. The third floor offers a full unfinished attic. Utilities are updated. Summer fun starts in the fenced in yard which includes an in ground pool, patio, and a garden area. Was it you who wanted a barn? It needs to be rebuilt but great potential.

Home for Sale

SPACIOUS, STYLISH AND PRICED TO MOVE! Welcome to the Winthrop Highlands! This beautifully updated home offers three levels of versatile living space, starting with a freshly updated kitchen featuring granite countertops, slate appliances, a center island, and gas cooking?perfect for whipping up meals and memories. The living room flows seamlessly into the dining room, both boasting refinished hardwood floors, while a tiled full bath completes the first floor. Upstairs, you'll find four bedrooms and a stunning full tiled bathroom or three bedrooms and a spacious office. You will find a spacious master ensuite on the third level. Meticulously maintained and thoughtfully updated this home includes a newer water line, roof, hot water tank, kitchen, bathrooms, driveway, and fencing. Outside, the backyard is your private oasis, with a fire pit/patio area, garden space, and a play area. All of this is just a short distance from the seaside charm and amenities of Winthrop. All boxes checked!

Home for Sale

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

Home for Sale

One of a kind! Queen Anne Victorian. Two blocks from Cottage Park Yacht Club. Over 4,400 square feet of living space with 6 bedrooms, 3.5 fully renovated baths, 2nd floor laundry room and 2 finished basement rooms. Stunning details include high ceilings, hand carved newel posts and mantels, 3 Chelsea tile fireplaces, oak flooring and woodworking, wainscoted staircases, window seat, pocket doors, and butlers pantry. Oversized windows provide an abundance of natural light. Bright kitchen featuring custom cherry cabinetry, Vermont soapstone countertops, and SS appliances, including a Sub-Zero refrigerator and a 6 burner Viking gas range. The almost 15,000 square foot lot has a 2 car garage with ample additional parking, a shed, and large private gazebo area. A beautiful copper finial topping the peak of the turret, clapboards, scalloped shingles, 2 wraparound porches, and perennial gardens add to this gem?s curb appeal. Availalbe for the first time in 30 years.

Home for Sale

This offering is about the land and the view. Located in Point Shirley, one of Winthrop?s most sought after waterfront neighborhoods, this shovel ready site sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing structure is intended for tear down. Zoning Board of Appeals approval has already been granted and the project is fully entitled. A buyer simply needs to pull a building permit and start construction. Setbacks and building dimensions are locked in, but the interior layout and all aesthetic choices are yours, from finishes and floor plan to siding style, window color, and design details.The land asking price $500,000, with a rare opportunity to leverage local construction financing. Cambridge Savings Bank offers programs with as little as 10 percent down, financing the full construction costs.

Home for Sale

This offering is about the land, the view, and the opportunity to own an affordable single-family property in an exceptional location. Located in Point Shirley, one of Winthrop?s most sought after waterfront neighborhoods, this shovel ready property sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing single-family structure is currently dilapidated and presents a buyer with two paths: restore the home or pursue new construction. Zoning Board of Appeals approval has already been granted, making this a fully entitled, shovel-ready opportunity. A buyer simply needs to pull a building permit and begin construction. Existing structure is intended for tear down. Zoning Board of Appeals approval has already been granted and the project is fully entitled.

Home for Sale

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 for outdoor relaxation. Additional highlights include a walk-up attic with potential for a roof deck with a little creativity. This thoughtfully cared-for property combines desirable waterside proximity with versatile indoor and outdoor spaces, making it an excellent opportunity for those seeking coastal living convenience.