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$1,050,000
6 Beds 3 Baths SOLD Status 73411596 MLS 2,144 SqFt.
Gorgeous turnkey 2 family home, steps from the beach, could be your dream home or an excellent investment! Both units feature spacious living rooms, three bedrooms each, eat in kitchens two full bathrooms and in-unit laundry! Unit 1 has a second bathroom ensuite. The units have been updated within the last two years with new flooring, new stainless appliances, upgraded cabinetry, and the entire home painted. Unit 1 has ductless mini splits for heating and cooling. The lovely yard features stone walkways, garden, mature pear tree and a private shaded patio for enjoying the outdoors! A short hop to the beach, restaurants, shopping, golf course, enjoy the beautiful setting and amenities of your new home that is so close to everything! One unit will delivered vacant, the other unit produces solid rental income to help cover a chunk of your mortgage. This move in ready home is a must see!

29 Dolphin Ave, Winthrop

$665,000
2 Beds 3 Baths SOLD Status 73410568 MLS 1,404 SqFt.
Welcome to luxury living at Belle Mer! This spacious 2 bed, 2.5 bath condo offers modern comfort and convenience just minutes from Boston and everything Winthrop has to offer—beaches, shops, restaurants, and more. Both bedrooms feature en suite baths, plus there’s a stylish half bath off the chef’s kitchen, complete with Bosch gas appliances and French doors leading to your private patio. Enjoy the feel of single-family living with your own private entrance, two parking spots right outside your door, great closet space, in-unit laundry, and tons of natural light. Converted in 2017, this well-appointed condo offers low-maintenance luxury living in a vibrant seaside community with easy city access.

142 Pleasant Unit 5, Winthrop

$925,000
3 Beds 3 Baths SOLD Status 73410084 MLS 2,341 SqFt.
Historic charm and modern comfort unite in this warm, inviting 3-bedroom, 2.5-bath home in the Ingleside Park neighborhood. Step inside to find stunning original woodwork, a cozy pellet stove perfect for cool summer nights, fresh paint throughout and the High-velocity AC will keep you cool all summer. 31 Lincoln has tons of upgrades...Brand new copper water line, new PVC drain to the street, new 200 amp electrical service and a fully remodeled finished basement. The roof is 10 years old and the exterior was just painted. The oversized lot offers plenty of room for kids, pets lovers, gardening or all of the above! You also have tons of parking for guests, easily park 6-10 cars. The oversized garage with epoxy floors at the rear of the lot is a car lover’s dream and could easily double as a home gym. All this on a quiet street just a short walk from Orient Heights T (Blue Line) and beautiful Ingleside Park. This is the one you’ve been waiting for!

31 Lincoln St, Winthrop

$417,000
2 Beds 1 Baths SOLD Status 73410030 MLS 900 SqFt.
WELCOME TO OCEAN FRONT LIVING ON WINTHROP BEACH. OCEAN VIEWS , OCEAN VIEWS, OCEAN VIEWS ! Wake up every morning and sit and enjoy the beautiful views of Winthrop Beach and the sun rising. Large Massport Windows that let in a ton of sunlight , step out of your door and put your feet in the sand ! This WELL MAINTAINED TOP CORNER UNIT condo boasts scenic views, hardwood thru out, newer tiled bath, freshly painted , 2020 NEW ROOF, FRONT SIDING , AND HOT WATER HEATER. Plenty of private storage in basement, bedrooms can be switched around and extra room can be office space or child bedroom. JUST MOVE RIGHT IN . Come see what Winthrop has to offer , many great restaurants, bars, beaches, waking jogging trails, pet friendly, shopping , so convienent to Boston and the North Shore, just minutes to T-Station , to the airport, and downtown Boston.

24 Winthrop Shore Dr Unit 2, Winthrop

$462,000
2 Beds 1 Baths SOLD Status 73408390 MLS 1,165 SqFt.
This charming, move-in-ready 2-bed, 1-bath condo in a gorgeous brownstone building offers historic character and modern convenience just minutes from downtown Boston! Beautiful original hardwood floors and bay window add warmth and timeless appeal. Both bedrooms are generously sized and filled with natural light. The second bedroom has a walk-in closet. The spacious, eat-in kitchen features tile flooring, Corian countertops, and direct access to a peaceful, private deck. Two oversized hall closets provide excellent storage options. Additional storage and shared laundry are conveniently located in the basement. Enjoy Ingleside Park at your doorstep, or take a short stroll to Donovan's Beach, shops and restaurants of Winthrop Center. Easy access to MBTA Ferry service to Boston & Quincy. Commuters will appreciate convenient bus service to Blue Line w/ easy access to city. First showing at first Open House this Saturday, 7/26, from 11:00 AM-12:30 PM. Offers due by Tuesday, 7/29, at 2:00 PM

94 Lincoln St Unit 2, Winthrop

$733,000
4 Beds 2 Baths SOLD Status 73406792 MLS 1,870 SqFt.
Back to Market due to buyer financing.....Tucked away on a quiet street, this home boasts stately features and has been meticulously renovated. From the elegant newel post to the timeless kitchen details, nothing was overlooked. During the condo conversion, preserving the home's original integrity was a priority. The first floor offers 2 bedrooms, laundry, and a full bath with marble tile floors. The sunlit living room, complete with a fireplace, opens to the dining room and the first of two decks, offering ocean views. The second deck is covered, perfect for rainy days. The kitchen features high-end appliances and classic white cabinetry. Upstairs, find 2 more bedrooms, including a primary with a large walk-in closet and full bath. Plenty of basement storage, separate entrances, and just minutes from Boston by car, with coffee shops and restaurants within walking distance.

3 Buckthorn Terrace Unit 2, Winthrop

$735,000
4 Beds 1 Baths SOLD Status 73406767 MLS 2,327 SqFt.
Prime corner lot in one of Winthrop’s most desirable neighborhoods! This home has great bones and is ready for new owners to make it their own. With an ideal layout, the second floor offers the perfect space for a primary suite with walk-in closet and full bath. The first floor features a spacious living room, with the opportunity to open up the kitchen and dining area for a large island and modern flow. A side entry leads into a generous mudroom with potential for custom storage. The backyard is perfect for a patio, outdoor kitchen, and entertaining. The garage could be connected to the home with a breezeway. Once renovated, this home could be worth $1.2M+. The price reflects the updates needed—bring your ideas and create your dream home! Builder tie in available if needed. Speak to our agent about financing possibilities from start to finish. This project is more attainable then you make think!

4 Circuit, Winthrop

$620,000
4 Beds 2 Baths SOLD Status 73406145 MLS 1,483 SqFt.
Welcome to this delightful charming home located in the highly sought-after Point Shirley section of Winthrop.With 7+ rooms, 3+ bdrms, and 1¾ 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 room features rich woodwork, wainscoting, and hardwood floors, creating a warm and inviting space.The updated kitchen combines modern convenience with classic charm, showcasing the original tall glass-front cabinets. A slider leads to a private backyard deck with pergola, ideal for entertaining or relaxing in your own outdoor oasis.The main floor also includes two versatile rooms one currently used as a home office and the other as a dining room. Upstairs, you'll find 3 rooms, offering incredible views and the potential to create a stunning primary suite. Don't miss this one! This is a keeper.

54 Townsend, Winthrop

$775,000
3 Beds 3 Baths SOLD Status 73406111 MLS 2,293 SqFt.
Ideally located just steps from the Winthrop Yacht Club, The Landing, 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 wrapped in lava-rock, plus two additional rooms perfect for a family room, guest room, or home office. The updated eat-in kitchen includes a convenient half bath with in-unit laundry and plenty of cabinet space with a Wolf Cooktop, Miele dishwasher and newer range. The upstairs offers three spacious bedrooms including an expansive oversized primary bedroom and a large full bath. The basement has an additional full bathroom, ample storage, and opportunity for future equity plays or extra rooms. 100 Cottage has a brand new 200 amp electrical service, new panel, and the perfect floor plan and is only 20 minutes to Seaport, less by ferry.

100 Cottage Ave, Winthrop

$1,175,000
4 Beds 4 Baths SOLD Status 73404847 MLS 2,214 SqFt.
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, fenced in backyard. The main suite opens to a private side deck and features a primary bath. Enjoy central air, second-floor laundry, a large basement for storage, a newer furnace and water heater (2022). The top floor offers a ocean views, and there's a hidden beach at the end of the street. Come discover the highlands of Winthrop. Winthrop offers many yacht clubs, marinas, parks, tennis courts, a golf course, and a seasonal ferry to Boston. Only 2 miles from Blue line. Come see this gem in a charming seaside town!

72 Sewall Ave, Winthrop

$720,000
3 Beds 2 Baths SOLD Status 73403913 MLS 1,172 SqFt.
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 bathroom. Don't worry about the summer heat, there is central AC. Would you like more space, down to the basement you'll enjoy the family room, dedicated laundry area and an additional storage room. Playground, beach, public transportation and great fun eateries are all close by as is easy access to Logan Airport and downtown Boston! Great opportunity to live in Winthrop by the Sea!

12 Park Avenue, Winthrop

$830,000
5 Beds 2 Baths SOLD Status 73403400 MLS 2,958 SqFt.
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 the home includes a full unfinished basement—ideal for storage or future expansion. Enjoy the convenience of off-street parking and a private backyard, perfect for outdoor entertaining or quiet relaxation.With its prime location near the ocean, beaches, and all that Winthrop has to offer, 37-39 Hutchinson is brimming with possibilities. Don’t miss your chance to own a large multi-family in a thriving coastal town just minutes from Boston!

37-39 Hutchinson St, Winthrop

$594,900
2 Beds 2 Baths SOLD Status 73401775 MLS 985 SqFt.
Welcome to The Somerset—Winthrop’s newest boutique condo development, where coastal charm meets modern luxury. This spacious 2-bedroom, 2-bath home is designed for effortless living, featuring a sun-drenched open layout, private balcony, and oversized walk-in wardrobes in both bedrooms. Enjoy a sleek kitchen with stainless steel appliances, quartz countertops, and soft-close cabinetry, flowing seamlessly into the living space—perfect for entertaining or unwinding. Retreat to the primary suite with a spa-like bathroom and generous closet space. Central A/C, in-unit laundry, and garage parking offer everyday convenience. The elevator building also includes a fitness center, stylish common lounge, and professional management. Located just moments from sandy beaches, shops, and dining, with easy access to downtown Boston—The Somerset is where coastal living meets city convenience.

10 Somerset Unit 206, Winthrop

$530,000
1 Beds 1 Baths SOLD Status 73401776 MLS 767 SqFt.
Welcome to Unit 408 – 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 A/C, and sleek modern details. The Somerset is an elevator building featuring a fitness room, resident lounge, and garage parking. Located in the heart of Winthrop, just minutes from beaches, neighborhood shops, and an easy commute to downtown Boston. Schedule your tour today— and see why so many are choosing The Somerset as their new home.

10 Somerset Unit 408, Winthrop

$679,000
3 Beds 2 Baths SOLD Status 73400042 MLS 1,849 SqFt.
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 to a large fenced-in yard, perfect for pets, gardening, or outdoor relaxation. The flexible second floor offers endless possibilities — use it as a spacious family room and guest suite with full bath, or transform it into a luxurious primary retreat with a walk-in closet and ensuite bath. Condo docs also give Unit 3 the right to expand/construct a roof deck without HOA approval. Additional highlights include: Hardwood floors being refinished prior to closing, basement storage, 2 off street parking, Dog-friendly building with only 3 owner-occupied units

44 Cliff Unit 3, Winthrop

$575,000
4 Beds 2 Baths SOLD Status 73394500 MLS 1,785 SqFt.
Step back in time, a stately 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 opportunity for commuters and history lovers alike. Enjoy the charm of small-town living with easy access to the city—a perfect choice for those priced out of Boston but still craving its energy and culture. Inside, the home offers a true canvas of preserved historical features awaiting your vision. With thoughtful cosmetic updates and restoration, you can breathe new life into this gem—blending vintage elegance with modern flair while retaining its original soul. This is more than a property—it’s a chance to create your dream home within the framework of history. Seller will not entertain low ball offers

123 Buchanan Street, Winthrop

$1,325,000
10 Beds 4 Baths SOLD Status 73396488 MLS 4,671 SqFt.
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 dining room. Owner’s unit, spanning the 2nd and 3rd floors, this enormous 5-bedroom, 2-bathroom unit can be delivered vacant for owner occupancy or new tenants. Enjoy a paved driveway with ample off-street parking. The property directly abuts Crest Ave Park, offering green space right next door. Commuter-friendly location with easy access to Boston and points North/South via major routes. Public transit is a breeze. Don't miss this massive 3-family gem

45 Highland Ave, Winthrop

$355,000
2 Beds 1 Baths SOLD Status 73396075 MLS 860 SqFt.
WELCOME HOME TO THE WINTHROP CHAMBERS CONDOMINIUM. Penthouse level - 2 bed, 1 bath unit with open floor plan. The views are incredible, whether it be of Lewis Lake and/or the Harbor/City, you will not be disappointed. There are coin operated washer/dryers in the building as well as a storage closet. The condo fee includes heat and hot water and this unit controls its own heat. Enjoy the back patio which is set up with high top table/chairs, gas grills for your use and your very own private beach. Parking is nearby at the Municipal lot. You are steps to the bus line which takes you directly to the Blue Line. Seasonal ferry is a few minute walk. Lots of great restaurants, walking trails and so much more that Winthrop By The Sea has to offer. Don't miss out on this wonderful opportunity to make this unit your own coastal retreat!

235 Washington Ave Unit 6, Winthrop

$920,000
3 Beds 2 Baths SOLD Status 73394225 MLS 1,831 SqFt.
Step inside this farmhouse-style gem and feel right at home. The first floor offers a spacious layout featuring a cozy eat-in kitchen with stainless steel appliances, a formal dining room, and a full bath with direct access to the backyard, perfect for easy pool days. Hardwood floors flow throughout, adding warmth and charm to every room. Character shines at every turn with thoughtful details that make everyday living feel extra special. Upstairs, you’ll find three comfortable bedrooms and a second full bath. The primary bedroom features two closets, offering plenty of space to create a private retreat. Outside is where the magic happens, your own private pool oasis awaits. The pool house with built-in sound sets the vibe and can double as a garage for storage or parking. Finished basement offers bonus space for an office, gym, playroom, or guests. Curb appeal tops it all off with a classic farmer's porch with a charming porch swing—perfect for morning coffee or winding down the night.

94 Circuit Rd, Winthrop

$948,888
5 Beds 2 Baths SOLD Status 73393038 MLS 2,532 SqFt.
Incredible opportunity to own a well-maintained 2-family home perfectly suited for investors or owner-occupants in seaside Winthrop! Conveniently located within steps to the water as well as the Center Business District, this property combines location, functionality, & value. Renovated in 2016 & over 2,500 sq ft of living space between two 6+ room units, this multi-family ensures comfort & peace of mind. The 1st floor offers an open floor plan with a fully equipped kitchen, 2 bedrooms, 1 full bath, den & 3 season porch. 2nd floor mirrors the 1st with an additional 3rd smaller bedroom & porch. The 3rd floor is home to an additional room currently used with unit 1, but the new owner can choose which unit uses the 3rd floor! A huge unfinished attic with high ceilings is ideal for future expansion. Outside enjoy the fenced in yard, oversized garage & parking. Whether you're looking to generate strong rental income or live in one unit while renting the other, this home offers flexibility!

200 Woodside Ave, Winthrop

$625,000
4 Beds 2 Baths SOLD Status 73392910 MLS 2,130 SqFt.
Rare opportunity to own two 4,000 Sq ft lots side by side in the beautiful Point Shirley neighborhood. 54 Otis Street and O Otis Street to be sold together in this sale.54 Otis Street in Winthrop, Massachusetts. This charming single-family home built in 1900, offering 2,130 sq ft of living space on a 4,000 sq ft lot. This residence features 8 rooms, providing ample space for comfortable living. The property is classified as a single-family residential home in the "Old style" category, reflecting its classic architectural design. 54 Otis Street presents an opportunity to own a piece of Winthrop's history. Its proximity to the beach and its location within a historic district makes it an attractive option for buyers interested in a home with character and coastal charm. 0 Otis Street that is included in the sale consists of a 4,000 sq ft lot, flat, with tandem 2 car garage. Property to be sold as is.

54 Otis Street, Winthrop

$605,000
2 Beds 1 Baths SOLD Status 73390944 MLS 1,262 SqFt.
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 large back deck, perfect for summer nights, overlooking a fenced yard with a new shed and freshly paved driveway. Up the rustic charming open wood staircase to find new carpeting and a flexible space ideal for an office or guest area, plus a third-floor loft for additional storage. Just minutes to the beach and nearby parks, this home invites you to experience Winthrop's coastal charm and peaceful lifestyle—just in time for summer! This home is perfect for 1st time homebuyers or down sizers.

88 Grand View Ave, Winthrop

$492,500
3 Beds 2 Baths SOLD Status 73390843 MLS 1,595 SqFt.
Coastal charm meets timeless elegance in this spacious 3-bedroom, 2-bath first-floor condo just moments from Winthrop’s stunning shoreline. Nestled within a beautifully maintained Victorian, this one-of-a-kind home blends historic character with everyday convenience. From the moment you enter, you’ll appreciate the soaring ceilings, intricate dental crown molding, sunlit bay windows, and ornamental fireplace. Thoughtful updates pair seamlessly with vintage features, including pocket doors, gleaming wood floors, in-unit laundry and ample storage tucked discreetly. Step outside and enjoy your own gardened yard-ideal for those who love light gardening or simply savoring the sea breeze. The lush outdoor space is a rare find for coastal condos and perfect for morning coffee or evening unwinding. Located just blocks from beaches, dining, with quick access to Logan Airport and public transit, this home offers the ease of city proximity with the peaceful pace of coastal living.

110 Summit Avenue Unit 1, Winthrop

$777,000
3 Beds 2 Baths SOLD Status 73390649 MLS 1,418 SqFt.
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 Revolutionary War as a fortification point to best view the British Ships in the ocean and Boston Harbor—commemorated today by a historic marker at the front of the property. Fully updated and move-in ready. This home on a private dead end street features: a spacious main suite with private bath, sweeping ocean views, an octagon lookout room, an upper top deck with breathtaking 360° vistas, an outside shower for beachgoers. A very short walk to Yirrell Beach, Deer Island State Park, and Coughlin Playground. This is a rare chance to own a scenic and historic gem. Schedule your private showing today

32 Hale Avenue, Winthrop

$900,000
5 Beds 3 Baths SOLD Status 73389581 MLS 2,946 SqFt.
Come look at this duplex 2-unit home in a prime location. The property is a great opportunity for investors looking to grow their portfolio in a strong rental market or the savvy owner looking to live in the property and enjoy rental income from the other unit. Other opportunities include conversion to condos or to a single residence. The larger unit at #86 has 8 rooms in total, 3 bedrooms, 1.5 baths, beautiful oak fireplace, 2nd fl laundry room, enclosed front porch, its own basement and attic. The other unit at #88 has 5 rooms in total, 2 bedrooms, 1 bathroom, side deck, enclosed front porch, its own attic and basement. The large back yard and mature plantings offer lovely green space and a 2-car garage. At the end of the street, enjoy a harbor beach, views of sunsets, the Boston Skyline, and boats in summer. Winthrop offers 3 yacht clubs, a marina, golf course, and a seasonal ferry to Boston. Very close to Winthrop Center shops and restaurants and public transportation.

86-88 Sargent St, Winthrop

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