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$977,700
3 Beds 3 Baths ACTIVE Status 73552912 MLS 2,451 SqFt.
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

$950,000
3 Beds 3 Baths CONTINGENT Status 73550478 MLS 1,749 SqFt.
OPEN HOUSE CANCELED! Welcome to the Highlands, where coastal living meets modern comfort. This beautifully maintained single-family offers water views, thoughtfully updated living spaces, and the flexibility today's buyers desire. The sun-filled main level features gleaming hardwood floors throughout, an upgraded kitchen, and an open layout that flows seamlessly to the spacious rear deck overlooking the fenced backyard with a private hot tub—perfect for entertaining or relaxing. Upstairs, the spacious primary suite offers a generous walk-in closet, while two additional bedrooms provide comfortable accommodations. The finished lower level provides versatile bonus living space ideal for a family room, home office, gym, or guest suite. Enjoy the best of indoor-outdoor living with inviting spaces designed for both everyday comfort and effortless entertaining. Just moments from the beach, this move-in-ready home combines modern updates, flexible living space, and an exceptional location.

50 Floyd St, Winthrop

$994,000
5 Beds 3 Baths UNDER AGREEMENT Status 73541368 MLS 2,564 SqFt.
Experience coastal living at its finest at 156 Locust Street. Just steps from the beach, this beautifully renovated 5-bedroom, 3-bathroom home offers over 2,500 square feet of stylish living space with ocean views and exceptional indoor-outdoor living. Renovated in 2022, the home blends modern luxury with timeless coastal charm. The stunning primary suite provides a private retreat, while a versatile first-floor fifth bedroom offers flexibility as a home office, bonus room, guest space, or playroom. Enjoy central air, sun-filled living spaces, and seamless access to the private fenced backyard and expansive deck, perfect for entertaining or relaxing after a day at the beach. Recent updates include heating systems (2024 & 2025), a hot water heater (2025), and upgraded 200-amp electrical service. Wake up to ocean views from the front balcony and enjoy a turnkey coastal lifestyle in one of Winthrop's most desirable seaside locations.

156 Locust St, Winthrop

$939,000
3 Beds 2 Baths ACTIVE Status 73537801 MLS 1,924 SqFt.
NEW PRICE! Fresh Updates! Now Vacant! Exceptional 2-family in desirable Winthrop. Same owner for 20 years! Turnkey opportunity for Investors or Owner-Occupants seeking strong rental income. Great for Multi-Gen living! Both units offer hardwood floors, closets, and spacious Kitchens w/ Pantrys. Windows galore! Gorgeous natural light! Beautifully proportioned rooms, easy floorplans, great storage. Welcoming farmer’s porch, fenced yard, and more! 3 OFF-ST PARKING SPACES. Unit 1 offers 2 BR’s, LR, DR, and huge Kitchen. Upstairs, Unit 2 features 1BR plus a windowed dressing room/WFH office, LR, DR, roomy Kitchen, along with exclusive access to a finished heated attic with 2 sunny bonus rooms ideal for WFH/guests/storage/gym. Unfinished basement with flex space for storage/hobbies. Steps to WINTHROP H.S. Close to parks, beaches, restaurants. Minutes to East Boston, Orient Heights MBTA/Buses, Logan, DT Boston. GPS "Oceanview"

105 Ocean View St., Winthrop

$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

$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

$949,900
2 Beds 3 Baths ACTIVE 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

$950,000
4 Beds 2 Baths ACTIVE Status 73509670 MLS 1,755 SqFt.
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

$975,000
4 Beds 2 Baths ACTIVE Status 73503359 MLS 2,916 SqFt.
~~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

$989,000
7 Beds 4 Baths UNDER AGREEMENT Status 72706576 MLS 3,800 SqFt.
A rare opportunity with a 2 family home on one of the best streets in Winthrop! One block to the ocean. Several locale yacht clubs. A few blocks to the town center with many shops, a few great cafes, several excellent restaurants, Great sized yard with a basketball court. One car garage and 4 car off street tandem parking. Refinished hardwoods throughout the entire home. Tiled bathrooms, kitchen, and second unit. Granite countertops and stainless appliances, Brand new Orient Heights T station off the blue line is a short bus ride away. (1.4 miles) Only a short 15 minute car ride to Boston. Washer / dryer room in both units. Central AC in 3rd floor. HUGE living room with a large wood burning fireplace. Comfortable three season front porch and generous sized open air rear deck.Third floor can be an oversized Master Suite or used as an in-law for extended family! There are not many homes like this in Winthrop.

170 Cottage Park Rd, Winthrop

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