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$565,000
2 Beds 1 Baths ACTIVE Status 73522468 MLS 928 SqFt.
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

$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

$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

$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

$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

$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

$1,100,000
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

$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

$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

$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

$549,900
2 Beds 2 Baths ACTIVE Status 73504907 MLS 969 SqFt.
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

$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

$1,450,000
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

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