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$779,000
3 Beds ⋅ 3 Baths ⋅ 73523728 MLS ⋅ ACTIVE Status
Stunning 2022 rebuild—taken down to the original foundation and rebuilt with a fresh, nearly-new feel throughout! This townhome-style condo feels like a single-family, nearly 2,000 sq ft, featuring 3 beds, 3 full baths, private outdoor space, and 2-car parking. NO monthly condo or HOA fees; annual master insurance just $1,670. A standout alternative to East/South Boston with quick Downtown Boston access via MBTA and highways. Sun-filled main floor with open living/dining, stylish kitchen boasting high-end appliances, two-tone cabinetry, large island, plus deck access. Upstairs includes two bedrooms with a primary suite showcasing dramatic cathedral ceilings. Finished lower level ideal for media room, gym, or guest space. Near marinas, waterfront parks, transit, and dog-friendly Belle Isle Marsh. Special financing from SIRVA Mortgage.

55 Banks St Unit 2, Winthrop

Listing courtesy of Listing Agent: Cheng Liang from Listing Office: CWQ Realty Group LLC.
$565,000
2 Beds ⋅ 1 Baths ⋅ 73522468 MLS ⋅ ACTIVE Status ⋅ ['Finlayson House On The Point Condominium'] BLDG.
This renovated 2-bedroom, 1-bath condo sits in the heart of Winthrop's Point Shirley, offering single-floor living with vaulted ceilings and skylights that give the space a brightness and openness rarely found at this price point. Natural light pours through every room throughout the day, flowing over hardwood floors that run wall to wall and tie the entire living space together seamlessly. Two private entrances add a level of independence and privacy that sets this home apart from typical condo living. The updated kitchen is well-equipped with gas cooking and stainless steel appliances, and the layout makes everyday living feel easy. In-unit washer/dryer and two off-street parking spots check the boxes that matter most to buyers in this market. Bonus: Private outdoor space add a layer or privacy most condos don't offer. 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.

16 Billows St Unit 2, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 73521657 MLS ⋅ ACTIVE Status
Nestled on a peaceful street between the shoreline of Donovan's Beach and the green space of Ingleside Park, this beautifully renovated single-family home offers exceptional flexibility and comfort across multiple levels. Thoughtfully updated from the rooftop to the lower level, the home is truly move-in ready with modern finishes and inviting spaces throughout. Sun-filled interiors create the perfect balance of open gathering areas and quiet workspaces, while large windows bring in abundant natural light. Designed for both everyday living and entertaining, the layout provides versatility for a variety of lifestyles. Step outside to an incredible outdoor setting ideal for relaxing, dining, and enjoying every season. With coastal charm, nearby recreation, and turnkey convenience, this home presents a rare opportunity to enjoy the very best of Winthrop living.

70 Edgehill Rd, Winthrop

Listing courtesy of Listing Agent: Kelvin Peters from Listing Office: Redfin Corp..
$399,000
1 Beds ⋅ 1 Baths ⋅ 73519126 MLS ⋅ ACTIVE Status
LAST STUDIO AVAILABLE! Discover effortless coastal living at Unit 304 at The Somerset, a boutique condominium community ideally located in the heart of Winthrop. This well-appointed studio offers a bright and airy open layout designed for both comfort and functionality, featuring a flexible bonus room with a sliding barn door ideal for a home office, guest room, or additional living space. The modern kitchen and living area are complemented by quartz countertops, stainless steel appliances, central A/C, and stylish contemporary finishes throughout. Residents enjoy convenient amenities including a fitness center, elevator access, and a welcoming resident lounge perfect for working remotely or gathering with friends. Just minutes from beaches, waterfront parks, local dining, and cafés, with quick access to downtown Boston via the Blue Line or seasonal ferry. Whether you're looking for a primary residence, investment property, or weekend escape, Unit 304 is home.

10 Somerset Unit 304, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
$849,900
2 Beds ⋅ 3 Baths ⋅ 73518550 MLS ⋅ ACTIVE Status
Residence 3 at The Pearl offers a bright, refined take on loft living within a reimagined church conversion. Original hardwood floors, exposed beams, oversized windows, and 15’6” ceilings give the home rare scale and character. The kitchen features white cabinetry, Bosch appliances, green soapstone counters, a waterfall island with seating, farmhouse sink, and architectural hood. The living area is anchored by a floor-to-ceiling fireplace wall with integrated display niches. Sculptural statement chandeliers, a library ladder, and hidden powder room beneath the staircase add thoughtful detail. The primary suite includes a private deck with automated retractable awning, walk-in closet, and modern bath with radiant heated floors. Two parking spaces, private storage, security system, Butterfly entry, and pre-wiring for electric curtains/blinds, sound, cable, and Comcast complete the home. Moments from beaches, shoreline paths, cafés, restaurants, and Boston access.

1001 Shirley Unit 3, Winthrop

Listing courtesy of Listing Agent: The Legacy Group from Listing Office: Serhant.
$299,999
1 Beds ⋅ 1 Baths ⋅ 73517506 MLS ⋅ ACTIVE Status
Welcome to The Cove, a distinguished condominium community in coastal Winthrop, offering a spectacular seaside setting with the Boston skyline as the backdrop for unforgettable sunsets. This renovated second-floor studio features wood flooring throughout, an updated kitchen with dining space, and a private balcony off the living area. The unit includes a modern bathroom with a walk-in shower, laundry in the building, and the rare convenience of two off-street parking spaces.Enjoy a short walk to the seasonal ferry for easy access to downtown Boston, along with additional nearby public transportation options. Two beautiful beaches are just a couple of blocks away in different directions, perfectly capturing the coastal lifestyle. Ideally located minutes from downtown Boston, Logan Airport, and major highways, with easy access to Winthrop’s local shops, restaurants, and waterfront charm. A great opportunity for first-time buyers — why rent when you can own?

600 Shirley St Unit 11, Winthrop

Listing courtesy of Listing Agent: Alla Rossi from Listing Office: Coldwell Banker Realty - Boston.
$819,999
4 Beds ⋅ 2 Baths ⋅ 73517107 MLS ⋅ ACTIVE Status ⋅ ['Seabreeze Condominium'] BLDG.
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.Every day the the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining room, ( Living room-could be master bedroom) the beautiful kitchen has cherry cabinets granite countertops, stainless appliances sliders to the large deck facing the sandy yard and Beach. This is one of a kind and Direct Ocean front living. All the rooms are large with plenty of character. Walk in closets and Laundry room make this for easy living. Bus line to the Blue line and Water shuttle into Boston is just a couple minutes away at the landing next to Winthrop yacht club. Marinas, shops and restaurants add to this great community. Don't miss out on this Opportunity to live Directly on a beach

876 Shirley Street Unit 1, Winthrop

Listing courtesy of Listing Agent: James Iannuzzi from Listing Office: Amo Realty - Boston City Properties.
$485,000
2 Beds ⋅ 1 Baths ⋅ 73515219 MLS ⋅ ACTIVE Status
Welcome home to this pristine and exceptionally well-kept two-bedroom, one-bath condominium in the heart of Winthrop’s vibrant 02152 community. This inviting home offers comfortable living along with private outdoor space—perfect for relaxing, entertaining, or enjoying coastal breezes. Conveniently located with easy access to Orient Heights, major highways, Logan Airport, and downtown Boston. The location of 43 Sagamore makes commuting simple while still enjoying the charm of a seaside town. Winthrop Beach is just moments away, offering the perfect setting for everything coastal living has to offer. A wonderful opportunity to own and become part of this welcoming waterfront community. Ask about available mortgage options.

43 Sagamore Ave Unit 1A, Winthrop

Listing courtesy of Listing Agent: Philip Lundberg from Listing Office: Lantern Residential.
$949,900
2 Beds ⋅ 3 Baths ⋅ 73514310 MLS ⋅ ACTIVE Status
Rooted in history and shaped by design, this loft at The Pearl offers something truly rare. Original hardwood floors and exposed beams, oversized windows & 15’6” ceilings create a striking sense of scale and atmosphere. The kitchen is both refined and dramatic, appointed with White shaker cabinetry, a Moonstone island, London Smoke quartzite, Bosch appliances, architectural hood, and a farmhouse sink set against warm wood details. Statement lighting, electric fireplace, library ladder and a hidden powder room tucked beneath the staircase add warmth, depth, and a strong sense of character throughout. The primary suite features a private deck, walk-in closet and a modern bath with radiant heated floors. Two off-street parking spaces, private storage, security system, and Butterfly entry add convenience. Moments from beaches, shoreline paths, local cafés & restaurants, this home offers the kind of lifestyle buyers often hope to find, but rarely expect this close to Boston.

1001 Shirley Unit 2, Winthrop

Listing courtesy of Listing Agent: The Legacy Group from Listing Office: Serhant.
$275,000
2 Beds ⋅ 1 Baths ⋅ 73513443 MLS ⋅ ACTIVE Status
Great opportunity in Winthrop just moments from the beach. This 2-bedroom, 1-bath first-floor condo offers 698 sq ft of single-level living with easy access, hardwood flooring, tile bath, gas heat, and one assigned off-street parking space. The monthly association fee includes heat, hot water, water, sewer, laundry facilities, exterior maintenance, landscaping, snow removal, and refuse removal, helping simplify ownership. Enjoy public beach access nearby, with area amenities including public transportation, shopping, parks, restaurants, schools, and highway access. A great option for buyers looking to enter the Winthrop market, downsize, or add to their portfolio.

173-175 Shirley St Unit 2, Winthrop

Listing courtesy of Listing Agent: The TrustPoint Group from Listing Office: eXp Realty LLC - Corporate Office.
$949,900
3 Beds ⋅ 2 Baths ⋅ 73513222 MLS ⋅ ACTIVE Status
Single Home, Great Location Great Shape Ready to Move In.

43 Loring Rd, Winthrop

Listing courtesy of Listing Agent: Jason Saphire from Listing Office: www.HomeZu.com.
$600,000
2 Beds ⋅ 2 Baths ⋅ 73511795 MLS ⋅ ACTIVE Status ⋅ ['Belle Mer'] BLDG.
Very reasonable condo fee. Newer built condominium in a prime Winthrop Center location, Belle Mer is a professionally managed association with 15 of 16 units owner occupied. Kitchen equipped with stainless Bosch appliances, wine cooler, + wonderful island to gather for enjoyment. Harbor views from the main bedroom, incredible closet space, and inviting window seat. Lofty ceiling height thru out + abundant wall space for art and photos. 2 pets are welcomed. 1 assigned parking space plus multiple guest parking. Convenient 2nd floor laundry. Bathrooms boast timeless designer tile. Ideal access into condo via front and back PRIVATE entries. The picturesque neighborhood is surrounded by natural beauty, a wonderful variety of cafes and eateries, yoga studios, farmers market, and ez access to Boston. This modern 2 bedroom, 2 bath condo on 2 levels Condo fee $300 Dog friendly

142 Pleasant Street Unit 12, Winthrop

Listing courtesy of Listing Agent: Stacey Steck from Listing Office: Gibson Sotheby's International Realty.
$950,000
4 Beds ⋅ 2 Baths ⋅ 73509670 MLS ⋅ ACTIVE Status
Wake up every single morning to beautiful, unobstructed water views from this home; sitting proudly on a rare, oversized lot. Positioned directly across the street from the water, this property offers the ultimate coastal lifestyle with endless space to expand, entertain, or build your dream outdoor oasis. Inside, you will find a couple of freshly painted bedrooms to offer a clean start, while the rest of the home is a blank canvas ready for your design ideas and style updates to make this home into your dream coastal escape. 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. Now offered at a new improved price, this is a great opportunity for an oversized lot and water views on the market. Washer, dryer, and refrigerator are being left as gifts!

118 Sunnyside Ave., Winthrop

Listing courtesy of Listing Agent: Donna Scalfani from Listing Office: William Raveis R.E. & Home Services.
$509,000
1 Beds ⋅ 1 Baths ⋅ 73509555 MLS ⋅ ACTIVE Status
Welcome to Unit 309—a bright corner 1-bedroom, 1-bath home featuring an open-concept layout, high-quality finishes, and a relaxed coastal style. The kitchen features stainless steel appliances, quartz countertops, central A/C, and modern design touches throughout. Residents enjoy elevator access, a fitness room, and a stylish common area—perfect for relaxing or savoring a morning coffee. Ideally located in the heart of Winthrop, you’re just minutes to sandy beaches, local shops, and an easy commute to downtown Boston.

10 Somerset Unit 309, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
$670,000
3 Beds ⋅ 1 Baths ⋅ 73509184 MLS ⋅ ACTIVE Status
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.

51 Undine Ave, Winthrop

Listing courtesy of Listing Agent: The Caceda Team from Listing Office: Coldwell Banker Realty - Lynnfield.
$649,000
2 Beds ⋅ 2 Baths ⋅ 73506354 MLS ⋅ ACTIVE Status ⋅ ['Seal Harbor'] BLDG.
Seal Harbor in Winthrop offers an elevated coastal living experience that is unparalleled. Timeless detail inside & out of this building is complemented by white-glove concierge service. Unit 342 is a luxury residence with ocean & pool views from every window. It is conveniently located a few steps from the new elevators & welcomes you into an open floor plan with striking natural sunlight; hardwood floors & a modern kitchen with island dining. Unit offers 2 spacious bedrooms with marble en-suite baths & walk-in closets. A private oversized balcony is the crown jewel with magnificent views. Conveniences include garage parking, extra storage ideal for seasonal items, in-unit laundry & central A/C. Residents enjoy premium amenities such as game room, club room with full kitchen, hobby room & multiple meeting rooms. Building also showcases a fitness center, sauna, hot tub, indoor pool & roof deck with Boston skyline & ocean views. Seal Harbor is a hidden gem on the Boston City line.

3 Seal Harbor Road Unit 342, Winthrop

Listing courtesy of Listing Agent: Nancy Ciampa McLaughlin from Listing Office: Redfin Corp..
$219,999
1 Beds ⋅ 1 Baths ⋅ 73505052 MLS ⋅ ACTIVE Status
Enjoy coastal living in this charming waterfront condominium in Winthrop, offering the perfect balance of convenience and seaside lifestyle. Located just minutes from Boston Logan Airport and with easy access to public transportation including nearby bus routes, the Orient Heights MBTA station, and the East Boston ferry, this home is ideal for commuters seeking quick access to Boston while enjoying a quieter coastal setting.

229 Washington Ave Unit 3A, Winthrop

Listing courtesy of Listing Agent: Vivian DaSilva-Braga from Listing Office: REMAX Executive Realty.
$549,900
2 Beds ⋅ 2 Baths ⋅ 73504907 MLS ⋅ ACTIVE Status
MAJOR NEW RENOVATION IN 2023.......EXCITING 2 BEDROOM, 2BATH UPSCALE CONDOMINIUM AT WINTHROP CENTER. Stunning oak floors and state of the art quartz and stainless kitchen, fully applianced with subway tile accents and an over sized island with pendant lighting. All open to a generous living area and access to an exclusive deck for personal outdoor space. A beautiful main suite with an amazing custom marble bath along with another room as a 2nd bedroom or bonus room. Incredible guest bath has stackable laundry as well. Basement storage and off street parking provide all the extras you hope for! A very convenient location near restaurants, coffee shops, banks, bakery, schools and lots more! Discover all of the natural beauty of WINTHROP by the SEA, WHERE PRIDE OF OWNERSHIP CAN BE YOURS!

35 Somerset Ave. Unit 3, Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.
$690,000
3 Beds ⋅ 3 Baths ⋅ 73503432 MLS ⋅ ACTIVE Status
***Seller is VERY motivated***Welcome to your fully renovated and updated home on a quiet corner in Winthrop. This home features a brand new kitchen with wide spanning island, open to the living room. Perfect for entertaining. All new electrical, water heater, furnace, plumbing, insulation and hard wired fire alarms. Approximately 250 sqft was added on and 2 bathrooms were also added making this a 3 bedroom 3 bathroom home. Conveniently located primary bedroom on the first floor has ensuite bathroom. All appliances in home are brand new, half bath located off the kitchen makes it easy for guests to use. Smart thermostat that can be controlled from your phone even when you are on the go. It really is a wonderful little corner lot home with ample yard space if you wanted a garden, front of the house gets sun all day. Walking distance to T and beach and other amenities Winthrop has to offer. OPEN HOUSE: 7/10 5:30-6:30PM. 7/11 10:30AM-12PM. OFFERS DUE MONDAY JULY 13th by NOON.

5 Oceanview St, Winthrop

Listing courtesy of Listing Agent: Nezihe Hewson from Listing Office: Mariano Smith & Co..
$975,000
4 Beds ⋅ 2 Baths ⋅ 73503359 MLS ⋅ ACTIVE Status
~~PRICE IMPROVEMENT~~ Introducing 24 FAIRVIEW STREET - a charming 4-bedroom, 1.5 bath Victorian in a prime, central location offering inside & outside enjoyment. This beautiful home has been enjoyed & maintained by the same family for many years & offers timeless appeal throughout. First floor has a family room, living room w/ a fireplace, modern kitchen w/ s/s appliances, separate dining area & 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 w/ two closets, a full tiled bathroom & a conveniently located laundry room w/ storage. The third floor offers a full unfinished attic. Utilities are updated. Summer vacation/family fun starts in the fenced in yard which includes an in ground pool, patio, & a garden area. Close to schools, shopping, public transportation & just 6 miles to Boston.

24 Fairview Street, Winthrop

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.
$1,450,000
6 Beds ⋅ 6 Baths ⋅ 73499355 MLS ⋅ ACTIVE Status
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.

100 Sargent Street, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.
$569,000
3 Beds ⋅ 1 Baths ⋅ 73497135 MLS ⋅ ACTIVE Status
Just one block from Winthrop Beach, this spacious and inviting condo offers 1,377 SqFt of comfortable living. With 3 large bedrooms and 1 full bath, there’s plenty of room for working from home, entertaining, or simply relaxing.Step inside to discover an open-concept living and dining area that flows seamlessly into a large, modern kitchen, featuring gas cooking, ample counter space, and a dedicated laundry area with access to your private deck. Outdoors, you’ll enjoy multiple spaces to unwind — a fenced yard, a charming farmer’s porch, and a garden area that sets the home back beautifully from the street.Conveniently located on the first floor, this home makes carrying groceries a breeze and provides easy access to the common yard and an oversized basement with abundant storage. Recent updates include a new hot water tank (2022), boiler (2020), and front porch (2018).Experience the perfect blend of coastal living and city convenience, with the newly improved Winthrop beach.

10 Beach Rd Unit 1, Winthrop

Listing courtesy of Listing Agent: Rogelio Zuniga from Listing Office: United Brokers.
$388,888
1 Beds ⋅ 2 Baths ⋅ 73464942 MLS ⋅ ACTIVE Status
8**Back on market due to out of state sale contingency falling through*** 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 WARM DAYS. JUST 5 MINUTES TO THE AIRPORT..GOOD INVESTMENT OR PERFECT FOR EMPTY NESTER OR TRAVEL BUG!

600 Shirley Unit 4, Winthrop

Listing courtesy of Listing Agent: Pratt Properties Team from Listing Office: Century 21 North East.
$1,324,900
4 Beds ⋅ 3 Baths ⋅ 73452093 MLS ⋅ ACTIVE Status
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.

129 Strandway, Winthrop

Listing courtesy of Listing Agent: Mark Savage from Listing Office: Byrnes Real Estate Group LLC.

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