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$369,000
1 Beds ⋅ 1 Baths ⋅ 73562209 MLS
Welcome to Summit View Condominiums. This sunfilled 1 bedroom unit , with private deck with magnificent views overlooking the town of Winthrop. Great neighborhood, steps to the beach, 1 min to bus stop, minutes to Orient heights t-station and just minutes to downtown Boston and easy access to the North Shore. OVERSIZED 1 bedroom, plenty of storage and closet space, walk in cedar closet, separate raw space for expansion, extra storage in basement, shared washer and dryer with only 1 unit, gleaming hardwood, tile and rug in bedroom. Feel like you living in a treehouse with all the mature surrounding trees. Winthrop is surrounded by miles of beaches, shopping, entertainment, bars, restaurants, marinas, Yacht clubs, and so much more

69 Summit Ave Unit 1, Winthrop

Listing courtesy of Listing Agent: Kevin Ferrara from Listing Office: Cottage Hill Real Estate.
$585,000
2 Beds ⋅ 2 Baths ⋅ 73561782 MLS ⋅ ['Seal Harbor'] BLDG.
Sixth-floor waterfront living at Seal Harbor in Winthrop Highlands. This 2-bedroom, 2-bath condo offers 1,203 square feet of single-level living with brand new hardwood floors throughout and direct ocean views from the main living space. The living and dining rooms flow together in an open layout, with a slider out to a private balcony where the water views are the main event morning and night. The kitchen sits just off the dining area with tile flooring and ample cabinet and counter space. Both bedrooms are well proportioned with new hardwood, the main bedroom comfortably fitting a king with room to spare and the second serving easily as a guest room or home office. Two full bathrooms, in-unit laundry, central heat and air, and a garage parking space beneath the building, and additional storage is available on site. Seal Harbor is a professionally managed, 127-unit brick building with a concierge, swimming pool, tennis courts, exercise room, sauna and steam room, clubroom, elevator, walking and jogging trails, professionally landscaped grounds with a gazebo, and beach access. The monthly fee includes water, sewer, master insurance, exterior and road maintenance, landscaping, snow removal, refuse removal, and management. The location puts you minutes from Winthrop Beach and the Deer Island trails, close to shops, restaurants, and public transportation, and a short drive to Logan Airport and downtown Boston. A rare combination of water views, garage parking, and full-service amenities at this price point.

1 Seal Harbor Rd. Unit 615, Winthrop

Listing courtesy of Listing Agent: Kevin Chiles from Listing Office: Charlesgate Realty Group LLC.
$250,000
1 Baths ⋅ 73561045 MLS
TURNKEY ITALIAN BAKERY & CAFÉ — REDUCED TO $250,000Rare opportunity to acquire a beautifully built-out, fully equipped bakery and café with approximately $450,000 invested in the build-out and equipment. Offered at just $250,000, this is an exceptional opportunity to step into an established commercial food-service facility without the substantial cost and time required to build one from scratch.The attractive café/retail area is complemented by a serious commercial production kitchen featuring extensive refrigeration and freezer capacity, refrigerated pastry displays, Blodgett convection and double-deck pizza ovens, commercial dough mixer and sheeter, 8-burner range, twin Pitco fryers, commercial hood with fire suppression, CMA dishwasher, stainless preparation areas, bakery racks, sinks and storage.Ideal for an Italian bakery, café, pizza/focaccia concept, catering operation, commissary kitchen, wholesale bakery, specialty desserts or breakfast/lunch operation.A tremendous amount of the costly infrastructure and equipment is already in place — offering the next operator the opportunity to move in and begin producing.

1234 Bakers Delight St, Winthrop

Listing courtesy of Listing Agent: Frank Pasciuto from Listing Office: Pasciuto and Associates.
$1,230,000
3 Beds ⋅ 3 Baths ⋅ 73560746 MLS ⋅ ['Seal Harbor Condominiums'] BLDG.
Experience elevated waterfront living in this stunning 3 bedroom, 3 bath penthouse at the prestigious Seal Harbor III. This exceptional two-level residence features a spacious open-concept floor plan designed to maximize natural light and showcase its spectacular waterfront setting. Entertain effortlessly or simply relax on the massive private deck, offering the perfect space to enjoy ocean breezes and breathtaking views. The kitchen boasts SS appliances, granite counters, Poggenpohl cabinetry and a breakfast bar. Enjoy the beautiful views while cooking. This 2 level unit offers the flexibility of a first floor bedroom and/or office. Nice open staircase. Lovely primary bedroom with en suite. There is a separate jacuzzi room which could become a home office if one chooses to do so. Seal Harbor III offers an unmatched lifestyle with exceptional amenities, including 24/7 concierge, a beautiful fireplaced lobby, an indoor heated pool and hot tub, a recently renovated fitness center, sauna, rooftop deck with panoramic views, outdoor swimming pool, tennis courts and multiple private resident gathering spaces. Additional highlights include a rare heated two-car garage, G9 and G11. Ideally located in the seaside community of Winthrop, you'll enjoy the tranquility of waterfront living while being just minutes from Logan Airport and downtown Boston, providing the perfect balance of coastal charm and city convenience. LUXURY, LOCATION, AND LIFESTYLE come together in this extraordinary waterfront Penthouse.

3 Seal Harbor Rd Unit PH33, Winthrop

Listing courtesy of Listing Agent: Cathie Curran from Listing Office: Charlesgate Realty Group, llc.
$765,000
4 Beds ⋅ 3 Baths ⋅ 73560385 MLS
This is your opportunity to own in beautiful Winthrop by the Sea at an incredible value! This spacious 4+ bedroom, 2.5-bath home offers the perfect blend of character, updates, and an unbeatable location. Relax on warm summer evenings from the inviting wraparound porch, or take a short stroll just one block to Winthrop Beach for sunrise walks and ocean breezes. Inside, you'll find oversized rooms, high ceilings, original hardwood floors, a renovated kitchen, spacious mudroom, and flexible living space, including two bonus rooms on the third floor and a partially finished basement with a bar, built-in shelving, and full bath. Major updates include the electrical system, gas furnace, water heater, most windows, allowing you to move in with confidence. A detached garage with electricity adds even more convenience. Just two blocks from a playground and basketball courts, walking distance to Winthrop's popular restaurants, coffee shops, breakfast spots, the Winthrop Yacht Club, and the seasonal Winthrop Ferry to Boston, this home offers the low-maintenance affordable coastal lifestyle you've been searching for. This is your chance to own a large single family in one of the most desirable seaside communities!

546 Shirley St, Winthrop

Listing courtesy of Listing Agent: Christine D'Ambrosio from Listing Office: Bowdoin Real Estate Partners.
$219,999
1 Beds ⋅ 1 Baths ⋅ 73560224 MLS
Enjoy coastal living in this charming waterfront condominium in Winthrop, offering the perfect balance of convenience and seaside lifestyle. Located just minutes from Boston Logan Airport and with easy access to public transportation including nearby bus routes, the Orient Heights MBTA station, and the East Boston ferry, this home is ideal for commuters seeking quick access to Boston while enjoying a quieter coastal setting.

229 Washington Ave Unit 3A, Winthrop

Listing courtesy of Listing Agent: Marcia De Paula from Listing Office: REMAX Executive Realty.
$397,900
1 Beds ⋅ 1 Baths ⋅ 73559020 MLS
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 U304, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
$975,000
3 Beds ⋅ 3 Baths ⋅ 73557515 MLS
Brand-new construction in the heart of Winthrop, offering a rare opportunity to own a thoughtfully designed new-build townhome in a coastal setting just outside of the city. As construction progresses, buyers may have the opportunity to personalize select interior finishes, making this home uniquely their own. Spanning approximately 2,100 square feet across two levels, the home features an open-concept kitchen, living, and dining area, along with a first-floor bedroom, full bath, and welcoming entry foyer. Upstairs, two spacious bedrooms each offer a private en-suite bath, with conveniently located second-floor laundry. Enjoy a private yard, city views, and one dedicated parking space. Located just minutes from Boston, Logan Airport, Winthrop Center, beaches, local shops, and restaurants, this is one of only two newly constructed townhomes at this address... a truly uncommon opportunity in Winthrop.

200 Main St Unit 1, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$549,000
2 Beds ⋅ 1 Baths ⋅ 73557185 MLS ⋅ ['Finlayson House On The Point Condominium'] BLDG.
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 Street Unit B, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$519,000
1 Beds ⋅ 1 Baths ⋅ 73556652 MLS
Waterfront Living at Its Best! Enjoy breathtaking ocean views from this spacious 8th floor condominium offering 974 sq ft of comfortable living space. Relax on your private balcony overlooking the water, or good size bedroom including a large walk-in closet and a separate tub/shower room. This full service building offers outstanding amenities, including concierge service, an oceanside heated pool with BBQ areas, tennis courts, an exercise room, and a scenic walking path along the shoreline. One garage parking space is included. Ideally located walking distance to restaurants. Minutes to Boston and Logan. This is coastal living with unmatched convenience. A wonderful place to enjoy waterfront living.

1 Seal Harbor Rd Unit 812, Winthrop

Listing courtesy of Listing Agent: Peggie Gilbert from Listing Office: Coldwell Banker Peggy Carter Team.
$625,000
3 Beds ⋅ 3 Baths ⋅ 73556640 MLS
Luxury living with downtown Boston just a few Train stops away! Escape the hustle and bustle of the city and enjoy the best of coastal living, with the beach right down the street. Step inside to a spacious mudroom that opens to a stunning open-concept kitchen—perfect for entertaining. Gleaming hardwood floors, granite countertops, and sun-drenched windows create a warm and inviting atmosphere throughout. With three beautifully finished levels of living space, there is plenty of room to spread out and make yourself at home. At the very top of the home, the charming widow’s peak offers the perfect opportunity to create your own private reading nook—one that would make any book club jealous! The private, fully fenced yard is ideal for relaxing, entertaining, or gathering around a fire after a day at the beach. Completely renovated in 2019, this beautiful home is ready for its new owner.

189 Shirley Unit 2, Winthrop

Listing courtesy of Listing Agent: Doyle & Waldron Team from Listing Office: Coldwell Banker Realty - Easton.
$829,900
5 Beds ⋅ 3 Baths ⋅ 73556586 MLS
Welcome to 43 Dolphin Ave, a charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile room currently used as a home office. Upstairs, you'll find three spacious bedrooms, a cozy sitting area, and a full bath. A porch roof patio over looking the ocean is a favorite spot to appreciate the views while you sit back and reflect on your day. A perfect ADU or in-law space in the finished lower level with a oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, with a laundry area, along with a bedroom with a full sized cedar closet. Right out your lower door is an area to have a table or another sitting area under cover. The outdoor shed has doors that open up to the pergola with a bar and tv so you can watch the games during your cookouts. Enjoy the convenience of three off-street parking spaces and easy access to Boston, Logan Airport, scenic waterfront trails, shopping, dining, and more. Don't miss it!

43 Dolphin Ave, Winthrop

Listing courtesy of Listing Agent: Patricia Nunez from Listing Office: Redfin Corp..
$859,900
2 Beds ⋅ 2 Baths ⋅ 73554136 MLS ⋅ ['Seal Harbor Three Condominium'] BLDG.
A rare offering at the prestigious Seal Harbor III, this exceptional corner residence captures breathtaking panoramic water views from an expansive, light filled interior and a private balcony - perfect for enjoying morning coffee, evening sunsets, or simply taking in the every changing waterfront scenery. Completely reimagined with a full gut reno in 2010, the home showcases timeless design, an open concept floor plan, and impeccable craftsmanship throughout. Thoughtfully curated with luxurious finishes and custom details, the residence is designed for both elegant entertaining and effortless everyday living. The spa-inspired primary bath features a steam shower, while the versatile second bedroom-equally suited as a den or private office-is enhanced by a striking custom leather accent wall. Seal Harbor III offers an unmatched lifestyle with exceptional amenities, including 24 hour concierge, deeded garage parking 2 spots tandem(D41T), outdoor/guest parking, heated indoor pool/hot tub, outdoor pool, storage closet, clubhouse, tennis courts and so much more.

3 Seal Harbor Unit 336, Winthrop

Listing courtesy of Listing Agent: Cathie Curran from Listing Office: Charlesgate Realty Group, llc.
$489,900
1 Beds ⋅ 1 Baths ⋅ 73551484 MLS ⋅ ['Seal Harbor'] BLDG.
Owner has relocated! Now is your chance. Wake up to SPECTACULAR SUNRISES over the Atlantic and fall asleep to the soothing sound of OCEAN WAVES in this affordable OCEANFRONT UNIT at Seal Harbor Condominiums! Offering UNOBSTRUCTED OCEAN VIEWS from EVERY ROOM, this beautifully maintained home delivers the ultimate coastal lifestyle while being a short drive to Boston & Logan Airport! Gleaming HW FLOORS flow throughout the OPEN CONCEPT LIVING & DINING AREAS, where a PRIVATE BALCONY provides the perfect setting to relax w/the ocean as your backdrop. The updated kitchen features SS APPLIANCES, GRANITE counters, w/a FULL HEIGHT BACKSPLASH complementing the stylish cabinetry. A SPACIOUS BEDROOM & UPDATED FULL BATH with a private shower area with a wall of closets and a NEW WASHER AND DRYER complete the space. Experience RESORT STYLE LIVING w/exceptional amenities including an inground pool, fitness center, sauna, steam room, tennis courts, clubhouse, beautifully manicured gardens with a gazebo, scenic oceanfront walking paths, recreational facilities and the convenience of a 24/7 concierge! This is COASTAL LIVING at its best!

1 Seal Harbor Unit 210, Winthrop

Listing courtesy of Listing Agent: Rita Angelesco from Listing Office: LAER Realty Partners.
$2,380,000
5 Beds ⋅ 6 Baths ⋅ 73550891 MLS
One of the most coveted locations in Winthrop, 174 Bartlett Rd is your dream costal retreat where luxury meets seaside living. Completely gut renovated, this exceptional home offers over 6,000 sq ft of beautifully designed living space across four expansive levels. The heart of the home is the stunning chefs kitchen with seamless oversized Brazilian Quartzite island surrounded by premium Sub-Zero, Wolf & Miele appliances, & a fully appointed entertaining bar. Anchored by a striking Valor fireplace, the two thoughtfully designed seating areas & expansive dining room create space for intimate or larger-scale entertaining. The Primary suite is a water view retreat with steam shower & BainUltra therapeutic soaking tub, dual walk-in closets, & private laundry. Welcome guests in the lower level suite, enjoy resort style yard with Gunite in-ground pool, basketball court & grilling island, or end days on the roof top deck with incredible views. This thoughtfully crafted home is unforgettable!

174 Bartlett Road, Winthrop

Listing courtesy of Listing Agent: Atiyeh Cassidy from Listing Office: Blue Sky Realty.
$715,000
4 Beds ⋅ 2 Baths ⋅ 73548082 MLS
Cape-style home in Point Shirley, steps from the beach and within Winthrop's most walkable stretch of coastline. Built in 1900 and updated with a remodeled kitchen featuring granite counters and recessed lighting, plus a remodeled full bath with a tiled tub and shower. Original hardwood floors run through the main level and all four bedrooms, paired with bay windows that bring in natural light and water views. The main level includes a living room with a fireplace, a formal dining room, and a sunroom that opens to a screened porch. Central air and forced air heat keep the home comfortable year-round. A full basement with sump pump offers storage and utility space, and a paved driveway provides two off-street parking spaces. Ocean views and public beach access nearby. 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.

52 Pebble Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
$869,900
3 Beds ⋅ 3 Baths ⋅ 73546996 MLS
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 and easily works for extended family ( IN-LAW POTENTIAL) 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.
$780,000
6 Beds ⋅ 2 Baths ⋅ 73545756 MLS
Ingleside Park 2-unit with a rare 10,000sqft oversized lot owned by the same family for over 20 years. Bring your ideas to transform this property into your dream investment or income-producing home with the untouched backyard begging to become either an outdoor oasis, additional parking, or more. Featuring off-street parking for 2 or 3 cars with the first floor unit offering two bedrooms, one full bath, and a large rear deck while the second floor unit has two levels with four total bedrooms, one full bath, and a rear sunroom. The building has separate electric and gas meters for each unit. Centrally located next to Ingleside Park and Winthrop Center only one mile to the MBTA Blue Line direct to Logan airport and Boston.

120 Hermon St, Winthrop

Listing courtesy of Listing Agent: Steve Binder from Listing Office: Binder Residential.
$699,000
4 Beds ⋅ 2 Baths ⋅ 73539167 MLS
PRICED TO SELL!! Best value in the neighborhood! Charming 1930's two family, originally a seaside cottage, just steps to the beach. This coastal home has been owned by the same family for over 70 years. It offers off street parking and flexible living options. It could be a great single family. Unit 1 is a one bedroom while Unit 2 has three bedrooms. This property is brimming with potential and is priced to reflect the updating needed - an excellent opportunity to create value in a prime location. Don't miss this wonderful chance to become a homeowner.

153 Locust St., Winthrop

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.
$650,000
3 Beds ⋅ 2 Baths ⋅ 73536296 MLS
Beautifully maintained and truly move-in ready, this 3-bedroom single-family ranch offers comfortable one-level living with the added bonus of a spacious finished lower level. The first floor features hardwood flooring throughout, with tile flooring in the modern full bath. The inviting living room features a fireplace, while the updated kitchen offers recessed lighting and a functional layout. Three bedrooms feature ceiling fans, and the finished lower level provides two bonus rooms, a full bath, laundry room, and separate storage area for added space and convenience. Abundant closet space throughout provides excellent storage.Pride of ownership is evident throughout this well-cared-for home, offering a clean, inviting interior and a move-in ready opportunity. Outside, enjoy a large backyard and spacious deck, perfect for entertaining, outdoor dining, or relaxing. Potential future ADU possibilities may exist, subject to local zoning and approvals. Ideally located near beaches, waterfront dining, parks, fitness facilities, and just minutes from Boston, this home offers comfortable living in a desirable Winthrop location.

496 Winthrop St, Winthrop

Listing courtesy of Listing Agent: Angela Dello Russo from Listing Office: United Brokers.
$485,000
1 Beds ⋅ 2 Baths ⋅ 73535636 MLS ⋅ ['Crystal Cove'] BLDG.
Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to Boston. Unit features tasteful upgrades, including a custom kitchen marble backsplash, quartz countertop and boasts not one, but two private decks featuring Trex decking. Unit 7 is widely considered the premier residence in the building, featuring the largest private waterfront-facing deck an ideal setting for morning coffee, outdoor dining, or simply taking in the spectacular views. Vinyle double hung windows with thermopane glass. Just in time for summer, this rare offering presents an incredible opportunity to enjoy, waterfront living at its finest.

600 Shirley St Unit 7, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.
$615,000
2 Beds ⋅ 2 Baths ⋅ 73535066 MLS ⋅ ['Seal Harbor'] BLDG.
Seal Harbor I Gorgeous ocean views from this sunny corner 8th-floor unit. Spacious living room with slider to a private balcony-This home features two comfortable bedrooms with large closets and beautiful views, a well-appointed kitchen with ample cabinetry and updated appliances, plus a newer washer/dryer. Enjoy resort-style amenities including an in-ground heated pool, fitness area, and a private walking path along the ocean. Winthrop offers miles of beaches, the Deer Island walking path, yacht clubs, golf, great restaurants, and easy access to Boston and Logan Airport. Includes underground parking space D11. If you love coastal living, you will love it here.......

1 Seal Harbor Rd Unit 815, Winthrop

Listing courtesy of Listing Agent: Peggie Gilbert from Listing Office: Coldwell Banker Peggy Carter Team.
$379,000
2 Beds ⋅ 1 Baths ⋅ 73534695 MLS
Welcome to coastal living at its best. HOA FEE INCLUDES HEAT & HOT WATER! This top-floor corner 2-bedroom condo offers ocean views & an ideal vantage point overlooking the water, bringing in incredible natural light throughout. Hardwood floors run throughout the living area, while the kitchen features granite countertops, stainless steel appliances, & ample storage. Recent upgrades include appx. $10K in custom built-ins & thoughtfully designed closet systems to maximize storage & functionality throughout the home. The open living & dining space creates an inviting setting for everyday living or entertaining. Both bedrooms offer generous space, while in-unit laundry provides everyday convenience. Enjoy a professionally managed, well-maintained building with many recent improvements such as a new roof & whole building water heater/boiler. Deeded parking, large locked deeded storage unit, two bus lines incl. a stop at the top of the street w/ direct Blue Line access, ferry access, & walkable walkable restaurants complete this ideal coastal lifestyle

53 Trident Ave Unit 301, Winthrop

Listing courtesy of Listing Agent: Amanda Woodward from Listing Office: Coldwell Banker Realty - Boston.
$1,100,000
6 Beds ⋅ 4 Baths ⋅ 73534385 MLS
A rare opportunity to own a 3-unit multi-family investment property with a fourth apartment in one of Winthrop's most sought-after coastal locations, just minutes from downtown Boston and Logan Airport. This asset offers an ideal mix for investors and owner-occupants alike. The property features one three-bedroom apartment, one two-bedroom apartment, one one-bedroom apartment, and one studio unit. The one-bedroom apartment is currently rented and will be conveyed with the property. The two-bedroom and three-bedroom apartments will be delivered vacant at closing. The owner is currently marketing the studio for rent. Three off-street parking spaces come with the property. Set on a 4,075± sq ft lot in a supply-constrained market with strong, year-round rental demand, the property delivers a compelling blend of in-place income and future growth potential through both rent increases and value-addition. Steps to the beach, Winthrop Golf Club, and the heart of Shirley Street - come see everything that this property has to offer.

32 Irwin St, Winthrop

Listing courtesy of Listing Agent: Michael Giannone from Listing Office: The Aland Realty Group LLC.
$2,250,000
16 Beds ⋅ 14 Baths ⋅ 73531829 MLS
DEVELOPMENT OPPORTUNITY WITH EXISTING MIXED USE PROPERTY GENERATING $71K NET ANNUAL INCOME.++A rare coastal investment and development opportunity in the heart of Winthrop, Massachusetts. The mixed use property currently consists of a cash-flowing four-unit mixed-use building with stable in-place NOI of 71,300, combined with a Board of Appeals–approved plan to construct a new 12-unit building with podium parking beneath — all on one site steps from the harbor and in the middle of a quaint yet thriving downtown Winthrop. 5-10 min commute to Boston Logan Airport, quick access to the MBTA Blue Line and ferry access to downtown Boston. All dimensions, square footage, parking spaces and building plans are estimated and should be considered for marketing purposes only. Buyers to do all due diligence as this is a development opportunity.

63-69 Putnam St, Winthrop

Listing courtesy of Listing Agent: The Bill Butler Group from Listing Office: Leading Edge Real Estate.
$495,000
73530360 MLS
Priced to Sell! This is your opportunity to purchase a versatile 2 unit commercial building located in Metcalf Sq in the Central Business District. The CB district allows for many possibilities such as mixed use & retail/office, etc.. and is a blank canvas for any investor, business owner or developer to transform/redesign this property to suit their needs with loads of potential to increase revenue. Current use is Office space, featuring a 1st floor unit w/great exposure, full windows, open layout suitable for office or possible retail. The 2nd fl unit has character & is bright and sunny w/2 large open areas, vaulted ceilings, (2) private offices, loft area, kitchenette and a private enclosed porch. The front entry is warm & inviting with 2 common restrooms, a nice size yard and a full walkout basement. Winthrop is a wonderful place to open/relocate a business or to invest in. there is meter-less street parking & municipal lots nearby. Current Rents are below market value. U#1-owner occupied, U#2-TAW.

11-13 Pauline St, Winthrop

Listing courtesy of Listing Agent: Lisa Leonard from Listing Office: Century 21 Mario Real Estate.
$495,000
2 Beds ⋅ 1 Baths ⋅ 73529631 MLS
Motivated seller! Wake up to panoramic ocean views and experience coastal living at its finest in this stunning top-floor condo directly across from Winthrop Beach. Featuring two private decks, high ceilings, hardwood floors, and sun-filled living spaces, this home offers the perfect blend of comfort, style, and seaside charm. Enjoy ocean views from your bed, an updated eat-in kitchen, modernized bathroom, and abundant natural light throughout. A versatile lower-level bonus room with a large walk-in cedar closet provides the ideal space for a home office, guest room, or fitness area. Additional conveniences include deeded parking and in-unit laundry.Now attractively priced and ready for its next owner, this is an exceptional opportunity to enjoy beachfront living just minutes from downtown Boston. Whether you're relaxing on the deck with your morning coffee or taking a walk along the shore, every day feels like a getaway.

52 Trident Ave Unit 52, Winthrop

Listing courtesy of Listing Agent: Alla Rossi from Listing Office: Coldwell Banker Realty - Boston.
$999,888
5 Beds ⋅ 2 Baths ⋅ 73529063 MLS
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

Listing courtesy of Listing Agent: Mirna Monterrosa Orellana from Listing Office: COM-PRO Real Estate Services, Inc.
$840,000
3 Beds ⋅ 3 Baths ⋅ 73526371 MLS
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.
$340,000
2 Beds ⋅ 1 Baths ⋅ 73525062 MLS
Bright and updated 2-bedroom condo at Governors Park featuring an open floor plan, renovated kitchen with granite countertops and stainless steel appliances, and spacious bedrooms with ample closet space. Professionally managed complex offers on-site laundry, swimming pool, tennis courts, and off-street parking. Conveniently located near public transportation, Winthrop Beach, shopping, dining, and just minutes to Boston and Logan Airport. Ideal for owner-occupants or investors seeking coastal living with city convenience.

800 Governors Dr Unit 6, Winthrop

Listing courtesy of Listing Agent: Fiorella Marte from Listing Office: Coldwell Banker Realty - Beverly.

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