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$975,000
5 Beds 2 Baths SOLD Status 73389456 MLS 3,970 SqFt.
Large two-family home in a highly sought after area in Winthrop on a large lot of land (7500sq feet). The property includes two spacious units and boasts a large backyard. The first-floor unit is a three-bedroom one bath, and the top unit is two bed-room one full bath and an unfinished master bath both units have lots of natural light. Second floor unit also has the added potential of a large unfinished area in the attic waiting to be finished. Tons of potential for owner-occupants looking to live in a coastal community while generating rental income, or for investors seeking a solid asset in a high-demand rental market. Enjoy all Winthrop has to offer including multiple yacht clubs, a golf course and many restaurants.

175 Somerset Ave, Winthrop

$715,000
3 Beds 1 Baths SOLD Status 73388954 MLS 1,269 SqFt.
Do you ever walk into a home and instantly feel at ease—like it was meant for you? 19 Banks Street does just that. From the sun-splashed porch with three walls of windows to the inviting living room with hardwood floors and a fireplace, this classic 3-bed, 1-bath Colonial blends charm and comfort. Enjoy paned windows, an easy flow, and modern updates like a new roof, high-efficiency gas heat, and tankless hot water. The kitchen features granite counters, stainless appliances, and a tile backsplash, and opens to a rare oversized fenced yard with a deck—perfect for relaxing or entertaining. Upstairs, the spacious primary bedroom is joined by two comfortable bedrooms and an updated full bath. A clean basement offers finishing potential, plus there’s a garage and two-car driveway. Set on a quiet Winthrop street near parks, beaches, trails, and transit—just minutes to Boston. This one feels like home.

19 Banks St, Winthrop

$440,000
2 Beds 1 Baths SOLD Status 73388681 MLS 812 SqFt.
Enjoy coastal living just one block from the ocean in this beautifully updated 2-bedroom, 1-bath home nestled in the heart of Winthrop. Step inside to a bright, airy layout featuring tasteful renovations and sleek, modern finishes throughout. The open-concept kitchen and living area is perfect for entertaining guests or relaxing at home. Off the spacious primary bedroom, a private deck offers the perfect perch for morning coffee or evening sunsets with ocean views. The newly renovated bathroom boasts a glass-enclosed shower, ample storage, and the convenience of in-unit laundry. Whether you're seeking a peaceful seaside retreat or a stylish year-round residence, this home offers the ideal blend of charm, comfort, and coastal convenience.

5 Pearl Ave Unit 2, Winthrop

$735,000
2 Beds 2 Baths SOLD Status 73387884 MLS 1,165 SqFt.
Experience the ultimate home getaway in this beautifully renovated 2 bed, 2 bath condo with stunning, unobstructed ocean views and deeded parking in Winthrop's growing community! Enjoy sunsets and sea breezes from your private balcony. Inside, 10+ ft ceilings, white oak floors, central AC, custom blinds, and smart home features offer lots of comfort and style. The chef’s kitchen boasts a waterfall White Quartz island, stainless steel appliances, gas stove, and soft-close cabinets, flowing into a large dining area. The spacious living, dining and kitchen area overlooks the beach. The primary suite includes a custom-tiled Italian shower; the second bath features a tub and in-unit laundry. Sitting as the largest unit it its boutique 7-unit building with private storage, a welcoming lobby, and rear stair access to parking. A rock's throw from beach access, the 712 bus to Orient Heights, and local favorites.

148 Winthrop Shore Dr Unit 4, Winthrop

$369,000
1 Beds 1 Baths SOLD Status 73386362 MLS 725 SqFt.
OCEANFRONT LIVING minutes from Boston! Classic building with wraparound porches across from Winthrop Beach has sweeping views of the Atlantic Ocean. This third floor condominium has 725 square feet and comes with a Full Off-Street Parking Space plus additional Guest Parking and a Brand New Gas Fired Boiler. The spacious living room has 2 south facing windows, wood floors and recessed lighting. The kitchen has white cabinets, tile flooring and a glass door that leads to a private deck/balcony with views of the ocean. The large corner bedroom has windows on 2 sides that offer both southern and western exposure. There is a full bathroom with tiled tub and shower. This home also offers oak floors, ample closets, common laundry and additional basement storage, all located within a short distance to restaurants, The Winthrop Yacht Club and nearby Marina’s, Winthrop Gold Course, Seal Harbor, Fort Heath Park, Revere Beach, Logan Airport & Public Transportation. Location is not in flight path.

203 Winthrop Shore Drive Unit 6, Winthrop

$850,000
3 Beds 2 Baths SOLD Status 73385622 MLS 1,998 SqFt.
Charming seaside living awaits at 81 Lowell Road in Winthrop- this neighborhood is a hidden gem! This beautifully maintained 3-bedroom, 2-bath home blends classic character with modern updates like 2024 central HVAC. Enjoy a sun-filled living and dining room, updated kitchen with stainless steel appliances, gas range, and hardwood floors throughout. Upstairs, the bright bedrooms have spacious designs along with an office or nursery with access to a walk up attic for future expansion! The finished basement adds flexible living space with a full bath, perfect for a media space or home gym. Outside, enjoy dining on your deck just off the kitchen or relax in the fenced yard, perfect for entertaining. Glorious hydrangea and rose bushes are blooming! Located in Winthrop's coveted Maze neighborhood, just steps from the beach, parks, and local amenities, and only a short commute to Boston. Simply wonderful living in an ideal location.

81 Lowell Road, Winthrop

$725,000
3 Beds 2 Baths SOLD Status 73384390 MLS 1,589 SqFt.
Welcome to your seaside retreat in the heart of Winthrop by the Sea! This beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of coastal living and modern comfort. Just steps from the beach, local yacht clubs, waterfront restaurants, and the ferry to Boston, you’ll enjoy the best of both tranquility and convenience, you'll find gleaming hardwood floors throughout, a cozy gas fireplace, and an updated eat-in kitchen perfect for everyday living and entertaining. The full basement offers exciting potential for expansion or extra storage. Outside, enjoy a beautifully landscaped yard with a garden area and a charming patio ideal for summer gatherings plenty of on site parking including a 2 car garage, a walkable neighborhood, and easy access to the city, this home is ideal for those looking to embrace the coastal lifestyle while staying connected. Don’t miss this rare opportunity to own a slice of paradise in Winthrop!

10 Ocean Ave, Winthrop

$615,000
2 Beds 2 Baths SOLD Status 73384246 MLS 1,361 SqFt.
Updated 2 bedroom, 2 bathroom bungalow located in the picturesque Point Shirley neighborhood of Winthrop. This detached single family home, boasting more than 1,300 square feet of living space, was recently renovated throughout to include wood-look porcelain tile, a brand new kitchen with stainless steel appliances and quartz countertops, a brand new master bathroom with a walk in shower including a pebble-stone shower floor and brand new central A/C and heat. This home includes an in unit side-by-side washer and dryer in a dedicated laundry room as well. Walk to beautiful Yirrell Beach in just 6 minutes. Enjoy an afternoon barbecue in your own beautifully manicured private back yard. MBTA Bus Stop located just a 6 minute walk with direct access to Orient Heights T Station.

50 Triton Ave, Winthrop

$540,000
2 Beds 2 Baths SOLD Status 73383627 MLS 773 SqFt.
“The Cove at 600” was converted in 2022 and is located on the site of the historic Crystal Cove Hotel with breathtaking views of the Boston Skyline and the Atlantic Ocean. Unit 3, located on the side of the building with a private entrance, exclusive use patio and exclusive use deck at the front of the building offers many ways to take in the view and the sea air. The open concept living room and dining room are bright and airy. The front bedroom is currently used as an office with striking views of the Boston Skyline. The main bedroom features an en-suite ¾ bath with beautiful tiled shower. This unit has baseboard heat and 3 mini splits for a/c. Full Size, in-unit laundry, great closet space, 2 exclusive use parking spaces and keyless building entry are some additional features. Short distance to bus lines, restaurants, beaches, and so much more. Easy living with the condo association taking care of the exterior maintenance. Now is the time to get in and enjoy the summer in Winthrop!

600 Shirley Street Unit 3, Winthrop

$1,250,000
5 Beds 3 Baths SOLD Status 73382376 MLS 2,430 SqFt.
This stunning 5-bed, 3-bath waterfront home offers breathtaking sunrises over the ocean and sunsets over the Boston skyline. The first floor features a bedroom and full bath perfect for guests or single-level living. Large open floor plan with tile floor. Stone fireplace anchors the middle of the room with space for a dining room table over looking the water. The kitchen boasts granite countertops, two islands, pot filler, built-in microwave and oven, and a sink with ocean views. Upstairs, find four spacious bedrooms with large closets and a full bathThe finished basement includes a laundry room, wine storage, pantry, office, ¾ bath, and ample storage. New central AC (March 2025). Outside, enjoy a meticulously maintained exterior with a deck and retractable SunSetter awning, a paved patio with built-in fire pit, and brand-new stairs leading directly to the beach. Move-in ready and just in time for summer! Winthrop has so much to offer restaurants, beach and public transportation.

896B Shirley Street, Winthrop

$383,542
1 Beds 1 Baths SOLD Status 73378713 MLS 475 SqFt.
The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage parking, and select units feature private decks, perfect for enjoying the ocean breeze. The building itself offers convenient amenities like an elevator, fitness center, and a welcoming common lounge—ideal for working remotely or catching up with neighbors over coffee. Moments from Winthrop’s beaches, just a short stroll from shops, restaurants, and the scenic shoreline. Easy commute to downtown Boston via the MBTA Blue Line or the seasonal Winthrop Ferry. Just looking for a seaside retreat with city access, The Somerset offers the best of both worlds.

10 Somerset Unit 403, Winthrop

$830,000
3 Beds 2 Baths SOLD Status 73378423 MLS 2,000 SqFt.
Welcome to 509 Pleasant, where coastal charm meets modern chic. This 3 bed/2 bath cottage style home is located in the ideal spot for both beach and city lovers. It features a smart system including Nest thermostat and Ring doorbell, a newer roof, recessed lighting, two fireplaces, a walk-in closet, in-built cabinets, a fully finished basement, a bonus room ideal for a playroom or gym, and an updated gorgeous wet bar and seating area! There is a large mudroom upon entry of the home, and ample room for storage. The sizeable patio is ideal for additional parking or to entertain your friends and family this summer. Located across the street from a marina, around the corner from parks and restaurants, a 10-minute walk to the blue line, and easy highway access. Come see this gem and everything it has to offer!

509 Pleasant Street, Winthrop

$940,000
4 Beds 3 Baths SOLD Status 73377824 MLS 2,470 SqFt.
Welcome to this timeless 8-room Whittemore Colonial, perfectly situated in the heart of the highly sought-after Cottage Park neighborhood.This spacious home offers 4 bedrooms, 2.5 baths, and the charm and character of classic architecture paired with modern updates.The main level features a gracious LR with a cozy fireplace, a formal DR highlighted by a stunning leaded glass built-in china cabinet, and an updated kitchen with SS appliances and island. A convenient 1/2 bath completes the first floor. Upstairs, you'll find a generously sized primary BDRM along with two additional BDRMS and a full bath.The 3rd floor offers a 4th BDRM and an additional room that could be easily finished. Lower level is ideal for extended living or guest quarters. Outside enjoy a nice backyard with patio and shed as well as 4 car parking. Rare opportunity to own a well maintained home in one of the area's most desirable neighborhoods.

19 Orlando Avenue, Winthrop

$670,000
3 Beds 2 Baths SOLD Status 73377272 MLS 1,413 SqFt.
Don’t miss this rare opportunity to own a well-priced single-family home in the heart of Winthrop by the Sea, under a 5-minute walk to both the beach and Winthrop Middle/High School. This charming home features 3 bedrooms and 2 full baths. The second floor also offers room for expansion to add a 4th bedroom, sellers are including the architectural plans. The main level boasts new appliances, granite countertops, and newer central air and heating (installed within the past 5 years). Enjoy outdoor living with a quaint backyard patio and a large enclosed front lawn with an enclosed white fence — ideal for entertaining, pets, or gardening. Additional features include 4 off-street tandem parking spaces, Versatile lower level with potential for a formal dining room or second family room and spacious, dry basement offering excellent storage. Move-in ready and full of potential!

162 Shirley, Winthrop

$520,000
2 Beds 2 Baths SOLD Status 73377046 MLS 1,219 SqFt.
Nestled in Winthrop’s sought-after Crystal Cove neighborhood, this beautifully maintained two-level condo perfectly combines timeless character with stylish comfort. A grand staircase serves as the home’s architectural showpiece, adding elegance and a sense of grandeur. The sun-filled unit features an updated kitchen, two bedrooms and renovated bathrooms offering modern finishes and functionality. The oversized living room sparkles with views of the marina and Boston skyline. Upstairs is a true retreat bedroom featuring skylights, gleaming floors and another bathroom. Throughout the home, original hardwood floors lend warmth and classic appeal. Step outside to your private deck, ideal for relaxing and enjoying water views. This pet-friendly property also includes two off-street parking spaces and outdoor patio area for convenience. Coastal Charm awaits with easy access to the ferry to Boston, public transportation, yacht clubs, trendy restaurants, beaches, playgrounds and more!

30 Crystal Cove Ave Unit 2, Winthrop

$880,000
4 Beds 2 Baths SOLD Status 73376243 MLS 2,366 SqFt.
Gorgeous farmhouse revival!!! Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge kitchens and natural light throughout. Some of the sunniest units you will see. Bathrooms like spas. High ceilings and great flowing layouts that make sense. The convenience of living in East Boston and the blue line nearby, without the congestion and lack of parking. Huge yard and driveway. Brand new heating systems, central A/C, upgraded plumbing and electrical. All the charm of a Victorian home w modern amenities. This elegant home is sure to turn heads with an aura of style and sophistication. Truly a special place that is not to be missed!

80 Shirley St, Winthrop

$715,000
2 Beds 2 Baths SOLD Status 73376200 MLS 1,738 SqFt.
Seaside living at its finest...welcome to your dream coastal retreat! This charming 2 bedroom, 2 bath bungalow with garage offers the perfect blend of comfort, style and breathtaking water views offering direct bay water access. Thoughtfully designed with an open floor plan and gleaming Brazilian cherry floors, the property features a warm and inviting sunroom that welcomes you with natural light and serene vibes. The heart of the home is the stunning cherry kitchen, complete with a breakfast bar, ss-appliances, granite c-tops and seamless flow into the living room and dining areas-perfect for entertaining or cozy nights in. The lower level offers flexible living space ideal for extended guests, au-pair suite or home office. Out back, take in spectacular sunrises and sunsets over the bay with captivating vistas of the Boston skyline. Out front, enjoy the ever-changing beauty of Yirrell Beach just steps from your door.

831 Shirley Street, Winthrop

$935,000
4 Beds 2 Baths SOLD Status 73376429 MLS 2,124 SqFt.
Excellent investment or owner-occupant opportunity in the heart of Winthrop! This two-family home features over 2,100 sq. ft. of living space, including a first-floor unit with 6 rooms, 2 bedrooms, and 1 bath, and a second-floor unit with 7 rooms, 2 bedrooms, and 1 bath—providing a total of 13 rooms across both units. The 3rd floor, unfinished walk-up attic is already plumbed and ready for future expansion, perfect for adding additional living space or creating a unique owner's suite. The second-floor unit also features a spacious three-season porch, ideal for a home office, sunroom, or relaxation space. Unit 1 (First Floor) is rented at $2,500/month on a Tenancy at Will. Unit 2 (Second Floor) is currently owner-occupied, offering flexibility for future rental or continued owner use. Parking for 4 cars (tandem style) plus a 2-car garage for additional covered parking or storage. Sunday, May 18th from Noon to 2pm.

96-98 Woodside Ave, Winthrop

$1,120,000
9 Beds 3 Baths SOLD Status 73375590 MLS 5,178 SqFt.
Offers due Mon 5/19@6pm- this wonderful beachside beauty w/ over 5000sf has been cherished & occupied by the same family for over 60 years. This property provides many options to the owner occupant, investor, or developer alike. All three units offer 3 beds, in unit laundry, formal dining rooms, eat-in kitchens, gorgeous original hardwoods, stunning waterviews from front porches and rear porches for additional private outside space (unit 2 &3 rear porches enclosed, U2 heated, and finished). Many upgrades, renovations, and improvements have been made by this family, who have enjoyed decades of The American Dream and love of the ocean in this home. Splendid location near yacht clubs, marinas, world class and family-run restaurants, and only minutes to Boston via car, public transportation, or the Winthrop Ferry. Named after the first Governor of Massachusetts Bay Colony, Winthrop is a gem that offers the perfect blend of small town sensibility, coastal charm, and proximity to Boston.

36 Forrest St, Winthrop

$935,000
4 Beds 3 Baths SOLD Status 73375100 MLS 4,101 SqFt.
Step into timeless charm with this stately 1896 Colonial Revival nestled on a corner lot. Brimming with original detail, this non-conforming two-family offers a flexible layout across 8+ elegant rooms. The grand staircase, French doors, high ceilings, and two fireplaces bring character and warmth throughout. Enjoy four spacious second-floor bedrooms, a sun-soaked landing with a large picture window, and a finished attic with three bonus rooms. A charming butler’s stairwell connects the upper level to the heart of the home—an updated kitchen with Brazilian teak floors, granite island, newer cabinets, and first-floor mudroom. A bonus first-floor room with ensuite bathroom offers versatile living for guests, home office, or multi-generational needs. A heated front porch, finished basement with full bath and steam room, and a fenced-in yard with private patio add comfort and luxury. The two-car garage includes a walk-up storage room. A rare blend of classic elegance and modern convenience!

175 Pleasant St, Winthrop

$480,000
2 Beds 1 Baths SOLD Status 73370480 MLS 694 SqFt.
This sun-filled bungalow offers the perfect blend of city access and coastal charm. Located minutes from Boston & steps from the Beach! This home features a private driveway, backyard, spacious deck & garden area—ideal for relaxing or entertaining. The front sunroom is perfect for morning coffee or a quiet reading nook. Enjoy quick access to local restaurants, shops, beaches, and the scenic trails of Deer Island. Winthrop's vibrant community includes a yacht club, surfing spots, and year-round coastal activities. A fantastic alternative to a condo—ideal for first-time buyers, pet lovers, or professionals seeking easy access to the city while living at the beach. Newer roof, updated insulation, tankless water heater. Under 2 minute walk to the beach. Don’t miss this opportunity!

24 Elliot St, Winthrop

$830,000
4 Beds 2 Baths SOLD Status 73372483 MLS 2,412 SqFt.
Nestled in the heart of Winthrop Head, this 4bed, 2bath Colonial blends timeless charm with a prime location just moments from multiple beaches and the scenic Winthrop Golf Club. Enjoy sweeping ocean views from the spacious front porch—an ideal spot for coffee or evening sunsets. Enter inside to a welcoming foyer featuring a bay window, fireplace & gleaming HW floors that flow seamlessly into a formal dining room perfect for entertaining. The kitchen includes a butler's pantry, offering ample storage and prep space. Upstairs, you’ll find four bedrooms and a full bath, w/ 2 addt'l bonus rooms on the third floor—perfect for a home office or guest space. The finished basement adds even more living space w/ a large family room, kitchenette area, full bath, additional storage, and walkout. Outside, the back patio provides a retreat for relaxation. This home offers the perfect blend of seaside tranquility & convenience, don’t miss your chance to own a piece of Winthrop’s coastal charm!

27 Crystal Cove Avenue, Winthrop

$960,000
5 Beds 3 Baths SOLD Status 73373237 MLS 3,272 SqFt.
115 Almont, where coastal vibes meet versatile living areas to offer something for everyone. Don't miss your chance to see this expansive 5 bedroom 3 bathroom colonial just minutes to Winthrop Beach, fantastic restaurants, schools & more. Upon entry, you are greeted with a beautiful living room with working fireplace, updated eat-in kitchen, full bathroom and first floor bedroom. This setup would be perfect for multi generational living or home office. Upstairs you will find a huge great room with floor to ceiling windows, high ceilings and wet bar- perfect for entertaining or relaxing (possibility of a ADU as well). Four generously sized bedrooms can be found on the second floor including a lovely primary suite w/ a private bath and ample closet space. Don't miss the attached 2 car garage w/ additional storage as well as driveway parking. This beautiful professionally landscaped corner lot home is ready for the next lucky owners to call "Winthrop By The Sea" their next forever home!

115 Almont St, Winthrop

$265,000
1 Beds 1 Baths SOLD Status 73371408 MLS 400 SqFt.
Looking for the perfect balance of city convenience and suburban tranquility? This newly renovated 1-bedroom, 1-bathroom condo is just a quick ride to the Orient Heights T stop, making your commute to downtown Boston easy. Plus, you're only 5 minutes from Boston Logan Airport, perfect for travel. Enjoy stunning views of the Boston skyline and harbor right from your door. Stroll to nearby oceanfront beaches where you can relax and unwind by the water whenever you wish. The condo offers a bright, open living space with modern finishes, ideal for a busy professional. Enjoy 2 private entrances! Updates: new kitchen, new bathroom, refinished hardwood floors, tile, new windows, updated electric, new stainless appliances, etc. Winthrop's local restaurants, a charming coffee shop, and a nearby yoga studio are just around the corner. Vibrant nightlife in Boston a short ride away. Renovated, move-in ready, and in a prime location. Perfect for Invester, 1st time buyer, or downsizing beach lover!

265 Washington Ave Unit 2A, Winthrop

$800,000
4 Beds 2 Baths SOLD Status 73371237 MLS 1,769 SqFt.
Welcome to coastal living on Point Shirley. This beautifully renovated 4BD, 2BA home invites you to slow down and enjoy life by the beach. Start your day watching the sun rise from your yoga/sunroom, or with a cup of coffee on your front porch. With tall ceilings and an open-concept layout you'll have sight lines from the living room to the dining room to the modern kitchen with quartz counters, gas cooktop, and pull-up breakfast bar. A full bath, laundry room, designated office, and two bedrooms complete the first floor. Upstairs, unwind in the lofted family room or retreat to one of the other two large bedrooms, one with a sunny bonus space where you can enjoy views of the Boston Harbor. Host friends and family on your back deck which overlooks the fenced in yard, perfect for games, grilling & lounging. All systems and roof are just 6 years young. Two blocks to Yirrell Beach, Deer Island walking paths, and vibrant Coughlin Park. Ferry and public transportation to Boston nearby.

77 Otis St, Winthrop

$525,636
3 Beds 1 Baths SOLD Status 73370999 MLS 1,120 SqFt.
Welcome to 66 Plummer Ave, a well-appointed 3-bedroom, 1-bath condo that offers the perfect blend of comfort, space, and convenience. This sun-filled home features beautiful hardwood floors and a spacious layout with a separate living room, dining room, and kitchen—ideal for both daily living and entertaining. Enjoy your morning coffee or unwind in the evening on either of the two private decks. Downstairs, you’ll find laundry and a large private storage area in the basement. Two deeded parking spaces and a shared outdoor space complete the package. Just a 5-minute walk to Winthrop Center and Pico Park, where you’ll find local shops, restaurants, and other town amenities—this is coastal living with everything right at your doorstep.

66 Plummer Ave Unit 2, Winthrop

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