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$660,000
2 Beds 1 Baths SOLD Status 73512130 MLS 1,304 SqFt.
Penthouse Condo with Harbor Views! Welcome to The Condos at 51 Harborview, ideally perched atop Water Tower Hill where this penthouse residence captures sweeping harbor and Boston skyline views with the ease of just one flight up. The final available home in this boutique collection, Unit 3 offers a rare opportunity for elevated coastal living. Features include 2 bedrooms, 1 bath, plus a bonus top-floor office ideal for work from home or flexible use. Modern kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl flooring. Enjoy a private harbor-facing deck, private yard space, deeded parking, in-unit laundry, gas heat, and mini-split A/C. Minutes to beaches, dining, and ferry service to downtown Boston.

51 Harbor View Ave Unit PH3, Winthrop

$600,000
2 Beds 2 Baths ACTIVE Status 73511795 MLS 1,141 SqFt.
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

$350,000
2 Beds 1 Baths UNDER AGREEMENT Status 73510931 MLS 977 SqFt.
Get ready to discover your next dream home! A fantastic condo for sale in the vibrant town of Winthrop, MA. This inviting residence features two generously sized bedrooms and a modern bathroom, complemented by an open concept living room and kitchen area.Situated in a large, welcoming complex, you'll enjoy excellent amenities including a tennis court and convenient laundry facilities in the building. The location couldn't be better—just a quick drive to Logan Airport and the Blue Line, making your commute and travel plans a breeze. If you’re looking for a blend of comfort, convenience, and community, this condo could be just the place for you! Don’t miss out on the chance to make it yours. Natural trail directly to the beach, fitness center and community pool. Some pictures are virtually staged.

1000 Governors Dr Unit 4, Winthrop

$1,141,500
10 Beds 3 Baths SOLD Status 73510613 MLS 3,978 SqFt.
Located just steps from the Atlantic, 24 Trident Ave delivers the rare combination of ocean lifestyle and investment fundamentals that rarely surfaces at this price point just minutes from Boston. This property delivers immediate income and serious long-term upside. Two leased (TAW) units generate $4,300/mo with the first-floor updated unit delivered vacant — perfect for an owner-occupant who wants tenants covering the mortgage from day one. This well-maintained 3-family sits less than a tenth of a mile to the beach, with ocean views from the upper floors. Each unit is laid out across a single floor with 3 bedrooms, a full bath, and 7 rooms — the kind of space that keeps good tenants in place. Three off-street parking spaces come with the property, and a full unfinished basement adds storage that owners and tenants will both put to use. Downtown Boston, Logan Airport, Route 1A, and public transportation are all minutes away, making this a prime opportunity that won't last.

24 Trident Ave, Winthrop

$1,100,000
3 Beds 2 Baths UNDER AGREEMENT Status 73510262 MLS 2,200 SqFt.
Want to live in Winthrop’s Highlands area? This beautifully renovated 3-BR, 2-Bath home offers the perfect blend of coastal charm and modern upgrades, featuring 2 car parking, water views, hardwood and porcelain tile floors. NO flood insurance required. A recent front room addition with sunset deck enhances both living space and the home’s connection to its surroundings. Chef’s kitchen featuring a Wolf 6-burner stove, built-in microwave, Sub-Zero refrigerator, beverage center, custom cabinetry. A large center island with abundant cabinet space makes this a true focal point of the home. Enjoy ocean views and a short walk to the beach. The outdoor space has been thoughtfully landscaped featuring flower beds in the front and side, vegetable beds, and a beautifully finished backyard with raised beds, perennials, fire pit, water fountain and an all-stone design creating a peaceful, Zen-like setting. Additional generous storage in the basement with potential for future extra living space.

21 Sewall Ave, Winthrop

$465,000
2 Beds 1 Baths SOLD Status 73510155 MLS 1,100 SqFt.
Top floor unit with exposed brick and a private garage, offering the perfect blend of character and modern updates! This sun filled home features a spacious open floor plan with white kitchen cabinetry, quartz countertops, and wood floors throughout. Generous bedrooms include a primary with a large closet and a second bedroom with a brand new custom closet system and washer and dryer for convenience. Freshly painted interior adds a clean, move in ready feel. Enjoy your private back porch deal for relaxing summer evenings. Garage includes electricity and a new door, plus a newly paved driveway. Recent exterior improvements include brick repointing and roof work. Ideally located just 1.5 blocks from the beach, close to restaurants, and convenient to public transportation perfect for commuters or those seeking coastal living!

95 Shirley St Unit 3, 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

$669,999
3 Beds 1 Baths PRICE CHANGED Status 73509184 MLS 1,250 SqFt.
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

$730,000
4 Beds 2 Baths SOLD Status 73508918 MLS 1,833 SqFt.
Where coastal living meets effortless style in the heart of Winthrop. This is more than a home. It’s a lifestyle. Wake up just moments from the ocean, where morning walks along the shoreline become part of your daily routine. Inside, the residence welcomes you with a bright, open flow designed for both comfort and connection—sunlight pouring in, tranquility at its finest, and a layout that simply feels right.The kitchen anchors the space, seamlessly blending into your living and dining areas—perfect for hosting, relaxing, or just enjoying a quiet night in. Every detail is designed for easy living, low maintenance, and maximum enjoyment.Step outside and you’re minutes to beaches, local restaurants, and an easy commute into Boston—giving you the rare balance of city access and coastal escape.Whether you’re a first-time home buyer, downsizing, or looking for that perfect seaside retreat—this is where your next chapter begins.

26 Shirley St Unit B, Winthrop

$849,900
5 Beds 3 Baths UNDER AGREEMENT Status 73508827 MLS 2,843 SqFt.
Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms & 2 bed.Kitchen has Induction Stove Top Granite Island & Counter Tops.Stainless Steel Induction Wall Microwave & Wall Oven.Top of the line Stainless Steel Refrigerator & Dishwasher.Granite tile floor. Plenty of Cabinet Space. Beautiful Tiger Hardwood Floors & Natural Woodwork Throughout. Crown Moldings & Chair Rails.Wood Fireplace in Living Room. There's a closet from the kitchen that was used as a staircase to the Basement that's finished with a huge full bath washer & dryer, Family Room & bedroom. That can be added in on the room count to 7 rooms 3 beds 2 full baths. 2nd floor 4 Large Rooms & 2 Bed.Plenty of Cabinet Space.Beautifull Hardwood Floors and All Natural Woodwork Throughout. Huge Living room. Dining Room has a spot for wall A/C. 4 Car Parking, Nice Huge Fenced in Yard with a Large Patio & Shed. Plenty of Parking Around The House Because of the corner Lot.5year old roof

7 Willis Ave, Winthrop

$999,900
7 Beds 3 Baths SOLD Status 73508785 MLS 3,628 SqFt.
This spacious multi-family offers 7 bedrooms and 3 full baths across 3,628 sq ft, with high ceilings on a 6,429 sq ft lot. Rarely available in Winthrop, it delivers exceptional size, flexibility, and strong rental potential. A cabin-style garage plus a driveway for 4 cars adds convenience, while the lot provides inviting outdoor space. Interiors are well maintained and move-in ready.The first-floor unit features 6 rooms and a full bath. The second unit spans two levels, offering 8 rooms and 2 full baths: the second floor includes the main living space, while the third floor adds additional rooms, a full bath, skylights, and wood floors, ideal for extended family or a private guest suite.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking strong income potential.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking income potential.

308 Bowdoin, Winthrop

$639,000
2 Beds 2 Baths PRICE CHANGED Status 73506354 MLS 1,302 SqFt.
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

$541,000
2 Beds 1 Baths SOLD Status 73506269 MLS 1,330 SqFt.
Beautifully refinished condo! Enjoy year-round comfort with central heating and air conditioning. The renovated kitchen is a standout, featuring newer cabinetry, quartz countertops, and a full suite of stainless steel appliances, including a dishwasher and garbage disposal. A spacious walk-in pantry with in-unit washer and dryer adds both convenience and functionality. Hardwood floors run throughout the expansive interior, complemented by abundant natural light. Offering over 1,300 square feet of living space, this home provides exceptional room to spread out, along with ample storage options. Two good size bedrooms, and a versatile office adjacent to the primary bedroom for those work from home days. A large walk-in closet too! Step outside to a private porch and take in beautiful beach views! More shared outside space out back with firepit area. Don't miss this beauty less only 3 doors down from Winthrop Beach!

35 Nevada St Unit #2, Winthrop

$505,000
2 Beds 1 Baths SOLD Status 73505743 MLS 764 SqFt.
Welcome to 101 Summit Ave, a beautifully updated condo offering ocean proximity and stunning views of the Boston skyline, all just a short walk to Winthrop Beach. The bright, open living area is perfect for both relaxing and entertaining. The updated kitchen features a newly installed oversized island, stainless steel appliances, quartz countertops, white shaker cabinets, and a charming coffee nook for your morning routine. Additional highlights include stained hardwood flooring throughout, an updated tiled bath, in-unit laundry, central AC, and recessed lighting. Step outside to your private deck and take in sweeping views of Winthrop and Boston. Dedicated storage space beneath the home, a large shared yard, and garden area add to the home’s appeal. All just minutes to the beach, local shops, and restaurants. A rare opportunity at this price to enjoy both high-end finishes and an unbeatable coastal location with easy access to the city. Open House Sunday, April 26th, 11:00AM-1:00PM.

101 Summit Ave Unit 1, Winthrop

$540,000
2 Beds 2 Baths SOLD Status 73505007 MLS 1,640 SqFt.
15 Ocean Dr #10 delivers flexible two-level living with dramatic ceiling height and oversized windows, all just minutes from Winthrop Beach. Newly renovated and move-in ready, this condo features two luxurious full baths, in-unit laundry, central A/C, one deeded off-street parking space, and access to a common roof deck with water views. The smart, versatile layout includes a main kitchen and living area on the upper level, plus a finished lower perfect for an office —ideal to work-from-home suite, media room, or private retreat. The well-maintained, professionally managed building includes water and sewer in the condo fee for added convenience. Enjoy an easy commute to both downtown Boston and Logan Airport by car, public transportation, or rideshare while still coming home to a quiet coastal community. This prime walkable location puts you close to Winthrop Beach, Norman Playground, local restaurants and cafés, the Winthrop Golf Club,

15 Ocean Ave Unit 101, Winthrop

$690,000
3 Beds 3 Baths ACTIVE Status 73503432 MLS 1,500 SqFt.
***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

$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

$1,331,000
8 Beds 4 Baths SOLD Status 73502452 MLS 4,260 SqFt.
Prime coastal investment opportunity in highly sought-after Winthrop! This 4-family property is directly across from the ocean with beach access and sits on a rare double lot, offering additional outdoor living, or expansion potential. Ideal for investors, owner-occupants, or multi-generational living. Unit 1 features 2 bedrooms. Unit 2 offers 2-3 bedrooms plus a home office w in-unit laundry hookups (could be used as a 3rd bdrm). Unit 3 consists of 3 bedrooms w a 3 seasons porch that views Boston skyline. Unit 4 is a 1-bedroom unit with the best views in the house. The property benefits from its prime coastal location with easy access to the beach, public transportation, restaurants and local amenities. Whether you’re looking to expand your investment portfolio or live by the water while generating income, this property delivers unmatched versatility and location.

419 Revere St, Winthrop

$835,000
5 Beds 3 Baths SOLD Status 73500423 MLS 4,768 SqFt.
Spacious 5-bedroom, 3-bathroom Craftsman bungalow on a corner lot just moments from Winthrop Center. Timeless Craftsman details include beautifully crafted built-in wood storage, adding warmth, character, and functionality. Oversized windows throughout fill the home with natural light. The top floor features a private primary suite with two walk-in closets and a dedicated makeup room. The first floor includes a kitchen, living room, dining room, two bedrooms, and a home office, offering an ideal layout for everyday living and entertaining. The finished basement adds two additional bedrooms and a large bonus room perfect for a playroom, office, or extra bedroom. A full bathroom on each level adds convenience. Additional highlights include central air and a newer roof. Not located in a flood zone. Rare opportunity to enjoy small-town coastal living just minutes from Boston.

108 Winthrop St, Winthrop

$375,000
2 Baths ACTIVE Status 73500196 MLS
Sports Bar for Sale - located in Winthrop. All Licenses are up to date and fully transferable- Liquor license included. Fully equipped kitchen- 8 burner stove, pizza oven, flat grill, ice maker, double door freezers x2, double door fridges, new 3 mini split ACs, new inter counter dishwasher, new beer cooler26 outdoor seating, 75 indoor seating, 9 TVs, 2 bathrooms with handicap access. Ample parking in the lot - about 15 parking spots. Used as a Sports Bar and Function hall. Owner currently has 2 other businesses and looking to sell this one to focus on the others. Great investment opportunity with everything included. 9 year lease remaining Rent- $5,200 ex utilities. Feel free to reach out for more info or if you’d like to view the establishment let me know to schedule a showing.

59 Putnam St, Winthrop

$1,450,000
6 Beds 6 Baths ACTIVE Status 73499355 MLS 5,278 SqFt.
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

$359,999
2 Beds 1 Baths UNDER AGREEMENT Status 73497859 MLS 723 SqFt.
Open House Sunday 04/26 1-2pm. Rarely available corner-unit condo offering exceptional privacy and abundant natural light. (Situated at the corner of the building, this home benefits from a side entrance that feels like private access). Freshly painted, the unit features a well-designed layout with comfortable living spaces and a seamless flow ideal for everyday living or entertaining.Located in desirable Winthrop, a vibrant seaside community just minutes from Boston, Logan Airport, and major routes. Enjoy easy access to Winthrop Beach, Deer Island, scenic waterfront paths, local shops, restaurants, and public transportation, all while maintaining a quieter residential feel. An excellent opportunity for buyers seeking convenience, coastal charm, and a sense of privacy rarely found in condo living.

300 Governors Dr Unit 21, Winthrop

$569,000
3 Beds 1 Baths ACTIVE Status 73497135 MLS 1,377 SqFt.
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

$515,000
1 Beds 1 Baths SOLD Status 73495543 MLS 840 SqFt.
Situated at the ocean's edge in Winthrop, the Seal Harbor condominium community is located just fifteen minutes from Boston's financial district. The building is amenity-rich offering 24/7 concierge, on-site management, secure underground garage parking, a heated outdoor pool with shower, bathrooms, full poolhouse kitchen, an outdoor Jacuzzi, and two gas grills. Residents also enjoy year-round access to an indoor pool on the 9th floor, complete with dramatic views, a new fitness center, as well as an indoor Jacuzzi and sauna with a large deck-perfect for viewing Independence Day fireworks! 3 Seal Harbor boasts three separate function rooms, where guests are able to enjoy table tennis, billiards and television. And in addition to the mature grounds, owners also have access to tennis courts, basement storage, bicycle storage, water sports storage and a full recycling facility. Unparalleled for its location, value, amenities, breathtaking views and proximity to Boston.NO DOGS PERMITTED.

3 Seal Harbor Rd Unit 634, Winthrop

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