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$977,700
3 Beds ⋅ 3 Baths ⋅ 73552912 MLS ⋅ ACTIVE Status
Location, location, location! Welcome to 211 Grovers Avenue, perfectly situated in the highly sought-after ocean community of Winthrop Highlands. This iconic brick-front Cape Cod sits on a 5,227 sq. ft. lot and radiates timeless character. Inside, you'll find an inviting living room featuring elegant tray ceilings and a warm fireplace. The home offers 3 bedrooms and 2.5 bathrooms, with incredible potential for expansion—the finished basement could easily become a teen suite, family room, or even an income-generating apartment. Outside, enjoy the coastal lifestyle with a great back deck, an attached garage, and a driveway, all just steps from the ocean. PRIVATE SHOWINGS START 8/7 through 8/9 PLEASE TEXT OR EMAIL LISTING AGENT

211 Grovers Ave, Winthrop

Listing courtesy of Listing Agent: Concetta Cicolini from Listing Office: Lamacchia Realty, Inc..
$899,900
3 Beds ⋅ 3 Baths ⋅ 73546996 MLS ⋅ ACTIVE Status
PRIDE OF OWNERSHIP CAN BE YOURS.......METICULOUSLY CARED FOR AND READY FOR THE NEW OWNERS! Located in one of Winthrop's most desirable areas, this Center Entrance Colonial has Harwood oak floors and a bath on every level. A huge fireplaced living room, eat in kitchen with a slider and deck overlooking the enormous (pool size) yard with a garden area and lots of off street parking. The second level has 3 bedrooms and a full bath and laundry. The Main bedroom is King-sized! The Bonus Room in the basement is multi purposed with another full bath, exrta high ceilings, open floor plan and a direct walk out to the yard. Another separate basement area is a handy workshop/storage area. THIS COULD BE THE ONE! In Winthrop by the Sea boasting 2 beaches, new schools, 3 Yacht Clubs, a nine hole golf course and lots of Great Restaurants!

37 Loring Rd., Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.
$1,480,000
4 Beds ⋅ 3 Baths ⋅ 73534719 MLS ⋅ ACTIVE Status
Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive improvements throughout. The open-concept layout is filled with natural light and showcases a beautifully appointed kitchen with custom cabinetry, quartz countertops, stainless steel appliances, a beverage refrigerator, and a large center island. Occupying the entire third level, the private primary suite offers breathtaking water views, a private balcony, a walk-in closet, and a spa-inspired bath. A rare opportunity to own a thoughtfully reimagined coastal home where panoramic water views, abundant natural light, and extensive recent reconstruction come together in one exceptional setting.

89R Upland, Winthrop

Listing courtesy of Listing Agent: David Cody from Listing Office: Orchard Park Realty.
$750,000
4 Beds ⋅ 3 Baths ⋅ 73534235 MLS ⋅ ACTIVE Status
Steps from the shore, this corner lot offers coastal living w a wide, expansive front porch perfect for catching the harbor breeze or entertaining. This move-in ready home features 2,700 sq.ft. of spacious living and an unbeatable beachside location. The interior boasts hardwood floors throughout most of the home, featuring four bedrooms and 2.5 bathrooms. Additionally, a finished third floor offers a versatile space for a home office or yoga studio, while the finished lower level is perfect for a home gym . The airy first floor features 8' ceilings and a seamless flow between the fireplaced living and dining rooms. The kitchen comes fully equipped with granite countertops, and the upper levels offer bedrooms with select water views. The property includes a driveway and a one-car garage. It is ideally situated just steps from the beach, parks, dining, and the MBTA water shuttle, providing easy access to Boston's Waterfront, the Seaport, and Logan Airport. Minutes into Boston.

546 Shirley St, Winthrop

Listing courtesy of Listing Agent: Melissa Flamburis from Listing Office: Redfin Corp..
$764,000
3 Beds ⋅ 3 Baths ⋅ 73530174 MLS ⋅ PRICE CHANGED Status
Welcome to coastal living at its finest in this truly unique and beautifully appointed townhome residence. Spanning three expansive levels, this exceptional three-bedroom, two-and-a-half-bath home seamlessly blends comfort, style, and privacy in the one and only seaside community of Winthrop 02152 Privately situated with its own separate entrance, this rare offering lives like a single-family home and features direct access to an enchanting secluded backyard retreat — a perfect escape for relaxing, entertaining, or enjoying quiet moments outdoors.Inside, thoughtfully designed living spaces are filled with natural light and offer the ideal balance of elegance and functionality. Just one block from the beach, enjoy the very best of coastal living while remaining only minutes from Boston, Logan Airport, and public transportation for an effortless daily commute.A

189 Shirley St Unit 1, Winthrop

Listing courtesy of Listing Agent: Nicole Bettano from Listing Office: Lantern Residential.
$855,000
3 Beds ⋅ 3 Baths ⋅ 73526371 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$779,000
3 Beds ⋅ 3 Baths ⋅ 73523725 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.
$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.
$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.
$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.
$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..
$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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