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$999,888
5 Beds 2 Baths ACTIVE Status 73529063 MLS 2,635 SqFt.
NEWLY PRICED! PRICED TO SELL! Rare waterfront two-family in Winthrop's sought-after Cottage Park neighborhood, offering stunning views of the Bay, Harbor, marsh, and ocean, a lifestyle feature you simply can't replicate at this price point. Built in 1920, this classic 2,635 sq ft two-story home sits on a 5,227 sq ft lot just steps from the beach. A perfect opportunity for first-time buyers or savvy investors. Unit 1 rents for $3,100/mo and Unit 2 for $4,000/mo, generating $85,200 in gross annual income with a net of $76,900. Five bedrooms, two full baths, and a versatile layout ideal for extended families. The property features an enclosed porch, deck, fenced yard, professional landscaping, and individually metered electric. Minutes from downtown Boston via Rt. 1A. Don't miss this opportunity; schedule your private showing today!

66 Sunnyside Ave, Winthrop

$855,000
3 Beds 3 Baths ACTIVE Status 73526371 MLS 1,837 SqFt.
This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a renovated kitchen with white beadboard cabinetry, quartz countertops, subway tile backsplash, and stainless appliances. The entire 2nd floor is dedicated to a private primary retreat, complete with two closets and a private en suite with glass shower. The sun-filled sitting room connects the suite to the 2nd-floor deck where ocean views make for the perfect spot for morning coffee or evening entertaining. A wood spiral staircase leads to the third-floor bedrooms tucked under vaulted ceilings. Corner lot with 2 driveways & the opportunity to expand the yard practically on the water in Pt. Shirley!

27 Billows St, Winthrop

$839,000
3 Beds 2 Baths UNDER AGREEMENT Status 73525692 MLS 1,736 SqFt.
Set on coveted Winthrop Shore Drive, this meticulously maintained penthouse presents an opportunity for elevated, uncomplicated beachside living with breathtaking ocean views from nearly every window. The expansive one-level layout with 1,736 SF of polished living space offers flow and function, comprising three spacious bedrooms, two full baths, 360 degree exposure, three distinct living areas and a bonus office. Highlights include the wall of Atlantic-facing windows enclosing the open living-dining areas, a turret-like primary suite with oversized bath and the view from the roof, where the deck of your dreams could overlook both the ocean and Boston's skyline. Even while immersed in natural beauty, residents enjoy every comfort & convenience: central AC, recessed lighting, high ceilings, premium appliances, stylish finishes, smart home features, in-unit laundry and easy access parking. Built in 2015, this beloved 3-unit building in A+ location also has extra storage and roof rights.

70 Moore St Unit PH, Winthrop

$399,900
2 Beds 1 Baths ACTIVE Status 73524736 MLS 664 SqFt.
The seller is offering a unique opportunity to lower buyer's payment temporarily for 3 years. The offer is a 3-2-1 temporary rate buy-down that reduces payments years 1-3 by 3% first year, 2% second year, 1% third year.Experience the best of seaside living in Winthrop, just steps from the beach. This beautifully updated two-bedroom corner condo offers stunning ocean views along with breathtaking sunrises and sunsets from nearly every window. Conveniently located close to public transportation and Boston Logan International Airport, this home offers the perfect balance of coastal charm and city accessibility.The bright and sunny third-floor unit features an updated kitchen with granite countertops, stainless steel appliances, and the convenience of an in-unit washer and dryer. HOA fees include heat and hot water. Also a nice size storage unit in the basement for extra storage. The professionally maintained building has undergone extensive recent improvements.

53 Trident Unit 303, Winthrop

$799,986
6 Beds 2 Baths ACTIVE Status 73523937 MLS 2,560 SqFt.
Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience and value for both owners and tenants. The property also offers plenty off-street parking, a paved driveway, and a private outdoor area. Conveniently located near restaurants, shopping, public transportation, beaches, Logan Airport, and major highways, making commuting into Boston quick and easy. Strong rental demand in the area creates excellent income potential and long-term upside. Whether you are looking to expand your investment portfolio, generate steady rental income or occupy one unit while collecting rent from the other, this property checks all the boxes!

50 Main St, Winthrop

$779,000
3 Beds 3 Baths ACTIVE Status 73523725 MLS 1,996 SqFt.
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

$779,000
3 Beds 3 Baths ACTIVE Status 73523728 MLS 1,996 SqFt.
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

$1,899,000
4 Beds 4 Baths ACTIVE Status 73521657 MLS 1,904 SqFt.
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

$399,000
1 Beds 1 Baths ACTIVE Status 73519126 MLS 546 SqFt.
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

$849,900
2 Beds 3 Baths ACTIVE Status 73518550 MLS 1,551 SqFt.
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

$974,900
5 Beds 2 Baths UNDER AGREEMENT Status 73518328 MLS 2,123 SqFt.
A forever home that doubles as your summer escape. Located in one of Winthrop's most desirable neighborhoods, this beautifully renovated single-family home offers three levels of coastal living. Step through the foyer and you’re greeted by soaring ceilings, a statement fireplace, and a dining space designed for memorable family dinners and entertaining alike. The chef’s kitchen steals the show with quartzite countertops, custom cabinetry, a professional grade Thermador gas range and water views. Completing the main level is a cozy den and heated sunroom. Upstairs offers four spacious bedrooms and a beautifully renovated full bath, while the entire third floor functions as a private guest suite complete with full bathroom and flex space ideal for a home officet, gym, or Peloton setup. Enjoy close proximity to Yirrell Beach, Ingleside Park, Belle Isle Seafood, The Half Cookie, Orient Heights Station, and and countless local cafés and restaurants - all just 6 miles from Boston

57 Loring Rd, Winthrop

$675,000
3 Beds 2 Baths SOLD Status 73518243 MLS 1,690 SqFt.
Spacious 3 bed/2 bath townhouse that lives & feels like a single family w/ oversized garage & expansive backyard located in the heart of Winthrop offering the perfect blend of coastal charm & city convenience. Enter to an open concept floor plan w/ living room & sliding doors that open to the private patio & yard- perfect for indoor/outdoor entertaining. Updated eat-in kitchen boasts abundant cabinetry, S/S appliances, quartz countertops & breakfast bar w/ seating for 3. 2 well-sized bedrooms that easily fit queen beds, generous closet space & a full bath with tub/shower combo complete this floor. The lower level features a spacious family room/office area & a large king-size bedroom w/ walk-in closet. In-unit laundry & a 2nd full bath w/ shower stall complete this floor. This home is complete w/ central air & 2 outdoor parking spaces. Live moments from all Winthrop has to offer-beaches, local shops/cafes/restaurants & easy access to public transit, Logan Airport and downtown Boston.

73 Bartlett Rd Unit 1, Winthrop

$725,000
5 Beds 2 Baths SOLD Status 73517634 MLS 1,935 SqFt.
Located just one block from Winthrop Beach, this spacious single-family home offers an incredible opportunity to own in a highly desirable coastal community with convenient access to the city. Featuring three levels of living space, this home includes 5 bedrooms, 1.5 bathrooms, and a fenced-in yard perfect for outdoor enjoyment. Ideally situated just 15 minutes from Logan International Airport and approximately 20 minutes to downtown Boston. Commuters will appreciate the easy access to public transportation, including the T and bus lines, as well as major highways such as Routes 1, 90, and 93. Situated on a double lot, this property may offer future expansion or development potential with the appropriate approvals and variances. Buyers and buyer’s agents to perform their own due diligence. OFFER DEADLINE MONDAY 5/18 12PM.

30 Hutchinson St, Winthrop

$299,999
1 Beds 1 Baths ACTIVE Status 73517506 MLS 351 SqFt.
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

$450,000
2 Beds 1 Baths SOLD Status 73517135 MLS 1,083 SqFt.
Beautifully maintained condo in highly desirable Winthrop offering the perfect blend of coastal charm and city convenience. This sun-filled home features a spacious open layout, generous living areas, large bedrooms with ample closet space, and stylish wall-to-wall bamboo laminate flooring throughout. Enjoy the convenience of in-unit washer and dryer, three-car parking, and a back porch perfect for relaxing and enjoying the ocean breeze. Located just steps from the beach, with easy access to local restaurants, public transportation, and downtown Boston. An outstanding opportunity for both owner-occupants and investors alike. Low condo fee of only $240/month makes this property an even greater value.

48 Crystal Cove Ave. Unit 2, Winthrop

$819,999
4 Beds 2 Baths ACTIVE Status 73517107 MLS 2,000 SqFt.
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

$550,000
1 Beds 1 Baths CONTINGENT Status 73517090 MLS 994 SqFt.
Experience refined waterfront living in this fully renovated, ocean-facing residence. The chef’s kitchen is a true centerpiece, featuring a brand-new center island, quartz countertops, and premium appliances—perfect for effortless entertaining. Modern upgrades shine throughout, including new electrical, recessed lighting, and sleek ceiling fans. Relax in the spa-inspired bathroom with a walk-in shower, or retreat to the spacious bedroom offering magnificent ocean views and ample space for a home office. Step onto your private balcony to savor morning coffee or golden hour sunsets over the water. This turn-key home includes garage parking and access to premier amenities: a pool, fitness center, and tennis(pickleball) courts. Embrace the Winthrop lifestyle with it's local beaches, a golfclub, and yacht clubs. Commuting is a breeze via the seasonal city ferry or nearby transit. From vibrant dining to scenic coastal trails, everything is ready for you to move in and enjoy!

1 Seal Harbor Rd Unit 300, Winthrop

$1,199,900
5 Beds 4 Baths ACTIVE Status 73515977 MLS 2,799 SqFt.
$2,500 bonus to buyer or buyer broker* Exceptional opportunity to live where you work. Corner lot with off-street parking, this unique property offers endless possibilities for investors, developers, or owner-occupants.The ground level features professional office space complete with a reception area, conference room, workspace, and 1/2 bath. Also included is a vacant 2-level, 2-bedroom, 1.5-bath unit that has been beautifully and completely renovated, featuring ocean views from the bedrm.In addition, the property offers a spacious 5-room, 3-bedroom, 1-bath unit and a large basement for added flexibility and storage.Conveniently located in a high-traffic area near schools, restaurants, and shops, just minutes from the public beach and major highway access. Potential to expand to 8-12 micro units. Buyers are encouraged to consult the Winthrop Bldg Dept. regarding the pot. expansion.Current tenants at will Ofc $2,500 U2 (3)bed $2,500 unit 3vacant *PLANS ATTACHED FOR POSS. 1BED UNITS W/O

193-195 Winthrop St, Winthrop

$1,199,900
ACTIVE Status 73515709 MLS
$2,500 bonus to buyers agent or buyer credit** opportunity in this mixed use in Central District. corner lot with off-street parking, this unique property offers endless possibilities for investors, developers, or owner-occupants.The ground level features professional office space complete with a reception area, conference room, workspace, and 1/2 bath. The vacant 2-level, 2-bedroom, 1.5-bath unit that has been beautifully and completely renovated, featuring ocean views from the bedrm.In addition, the property offers a spacious 5-room, 3-bedroom, 1-bath unit and a large basement for added flexibility and storage.Conveniently located in a high-traffic area near schools, restaurants, and shops, just minutes from the public beach and major highway access. Buyers are encouraged to consult the Winthrop Bld Dept. regarding potential expansion. Current taw Ofc $2500,U2 3bed $2,500 u3 vacant, total area 5548 liv area 2799 per public rec *PLANS ATTACHED FOR POSS. 1BED UNITS W/Ofc

193-195 Winthrop St, Winthrop

$485,000
2 Beds 1 Baths ACTIVE Status 73515219 MLS 913 SqFt.
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

$1,299,000
5 Beds 2 Baths UNDER AGREEMENT Status 73514990 MLS 3,754 SqFt.
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.

264 Court Rd, Winthrop

$475,000
1 Beds 1 Baths UNDER AGREEMENT Status 73514946 MLS 623 SqFt.
Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking. Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

140 Shirley Street Unit 230, Winthrop

$899,900
2 Beds 3 Baths PRICE CHANGED Status 73514310 MLS 1,806 SqFt.
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

$550,000
2 Beds 1 Baths SOLD Status 73513260 MLS 1,267 SqFt.
OPEN HOUSE CANCELED!! Perched on the top floor, where the light lingers and views stretch toward the water, this two-bedroom condo in Winthrop’s Highlands feels quietly elevated from the moment you arrive. Sunlight pours through oversized windows, drawing your eye to the ocean and filling the open living and dining space with an easy, natural flow.The kitchen is thoughtfully updated, offering both style and function at the center of the home, while hardwood floors and timeless details add warmth and character throughout. Step outside to front and back decks—two private spots to take in the coastal air, from morning coffee to evening unwind. A flexible bonus room offers space to work, create, or store, while two comfortable bedrooms and renovated bath complete the home. Below, a shared yard adds a bit of green, and off-street parking brings everyday ease. Set in one of Winthrop’s most sought-after neighborhoods, this is a home where character and ocean views come together effortlessly.

173 Grovers Ave Unit 3, Winthrop

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