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22 Adams St, Winthrop
$1,250,000
7 Beds ⋅ 3 Baths ⋅ 73510154 MLS
Stunning turn of the century three family home in a prime commuter location! Unit 1 &3 offers a spacious layout with large living room, formal dining room, kitchen, 2 bedrooms. Unit 2 offers smilar layout with 3 bedrooms and private deck. Tucked away on a quiet side street just above the town center, yet only a half-block to the bus line, restaurants, and everyday amenities. Enjoy easy access to Deer Island, beaches, and scenic bike trails. Ample on street parking with nearby public lots. Strong rental potential with 2-bedroom units commanding $2,500+. Perfect for investors or owner-occupants seeking location, space, and income opportunity.

22 Adams St, Winthrop

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.
50-52 Wilshire St, Winthrop
$990,000
6 Beds ⋅ 2 Baths ⋅ 73480670 MLS
Outstanding Winthrop investment opportunity offering strong income potential in a highly desirable coastal community. This newly renovated two-family property features two spacious units (2BR and 4BR), ideal for owner-occupants seeking rental income or investors looking to expand their portfolio. Both units provide modern living with off-street parking for four vehicles total. Conveniently located just minutes from major highways, public transportation, shopping, beaches, and local schools, this property combines location, flexibility, and long-term upside in one exceptional offering.1st Open House Sat FEB 28TH (12-2 PM)

50-52 Wilshire St, Winthrop

Listing courtesy of Listing Agent: Lou Markakis from Listing Office: Lynnway Associates.
108 Winthrop St, Winthrop
$835,000
5 Beds ⋅ 3 Baths ⋅ 73500423 MLS
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

Listing courtesy of Listing Agent: Mark Mulkerrin from Listing Office: Coldwell Banker Realty - Sharon.
45 Read Street, Winthrop
$815,000
4 Beds ⋅ 2 Baths ⋅ 73464677 MLS
Welcome to Winthrop this beautiful classic colonial awaits you! This lovingly cared for home has been with one family for the last 29 years and is perfect for the extended family. The original home built in 1920 includes a newer two story addition offering lots of living space. The extra large eat in kitchen was completely remodeled in 2021 and features beautiful white cabinetry, stainless steel appliances and quartz counter tops perfect for all your family gatherings. There are 4 plus big bedrooms with lots of closet space & 2 full baths. There are formal living & dining rooms both with hard wood flooring, a family room, separate first floor laundry room, beautiful entry way, and lots of natural light. There is also a large full unfinished basement with endless possibilities. Outside is a deck, large fenced in yard, and plenty of parking, all situated on a large lot. Come view this home today!

45 Read Street, Winthrop

Listing courtesy of Listing Agent: William Stewart from Listing Office: Sgarzi & Stewart Real Estate, LLC.
34 Fremont St, Winthrop
$685,000
4 Beds ⋅ 2 Baths ⋅ 73460212 MLS
34 Fremont gives you something most homes in town can’t: space to grow into on a bigger-than-normal lot near Winthrop Center. The main level flows the way a home should: kitchen with pantry, dining and living rooms connected, and an office when you need a door closed. Upstairs you’ll find three comfortable bedrooms plus two additional rooms that are perfect for kids’ bedrooms, a second office, future walk-in closets, or even the foundation for en-suite bathrooms as you update over time. The top floor was reimagined into a private retreat, removing a wall to create today’s primary suite. It’s a roomy hideaway with hardwoods and storage you can keep expanding. Screened porch for summer nights. 34 Fremont still has 2-3 off street parking spots & is still close enough to the beach you will actually enjoy it. An 1886 home with solid bones on a 7,390 sq ft lot, ready for someone who wants the neighborhood and the future potential baked right in.

34 Fremont St, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
10 Somerset Unit 306, Winthrop
$634,935
2 Beds ⋅ 2 Baths ⋅ 73528235 MLS
Welcome to The Somerset—Winthrop’s newest boutique condo development! This 2 bed/2 bath designed home offers an open layout with quality finishes and a coastal vibe. Enjoy open-concept living, stainless steel appliances, quartz countertops, central A/C, and stylish modern touches. Most units include garage parking, and select homes feature private decks. The elevator building also offers a fitness room and a welcoming common area—perfect for relaxing or enjoying a coffee. Ideally located in the heart of Winthrop, just a short distance from sandy beaches, local shops, and an easy commute to downtown Boston.

10 Somerset Unit 306, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
10 Somerset Unit 201, Winthrop
$629,000
2 Beds ⋅ 2 Baths ⋅ 73458592 MLS
Welcome to Unit 201 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The Somerset offers garage parking, a fitness room, elevator access, and a cozy resident lounge ideal for remote work or casual connection. Close proximity to sandy beaches, waterfront parks, and local restaurants, with convenient access to downtown Boston via the Blue Line or seasonal ferry. Whether you're seeking your next home or a seaside escape with city access, Unit 201 delivers space, style, and a lifestyle by the sea. Book a tour today!

10 Somerset Unit 201, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
82 Putnam St Unit 2, Winthrop
$615,000
3 Beds ⋅ 2 Baths ⋅ 73547219 MLS ⋅ ['80-82 Putnam St Condominiums'] BLDG.
Your chance to own a beautiful home in vibrant Winthrop by the Sea! Freshly updated 3-bedroom, 2-bathroom townhome-style condo with an entertainer’s floor plan including a modern kitchen with granite and a peninsula, dining area, large living room, full bath, Central A/C, and private deck. 3 well-sized bedrooms upstairs and a shared Jack and Jill bath with herringbone tile. Convenient in-unit laundry on the main floor, basement storage, and 2-car parking in driveway. Steps to Winthrop Center and an effortless commute with easy MBTA bus connection to the Orient Heights Blue Line.

82 Putnam St Unit 2, Winthrop

Listing courtesy of Listing Agent: Team Ladner from Listing Office: RE/MAX Harmony.
10 Somerset Unit 206, Winthrop
$594,900
2 Beds ⋅ 2 Baths ⋅ 73401775 MLS
Welcome to The Somerset—Winthrop’s newest boutique condo development, where coastal charm meets modern luxury. This spacious 2-bedroom, 2-bath home is designed for effortless living, featuring a sun-drenched open layout, private balcony, and oversized walk-in wardrobes in both bedrooms. Enjoy a sleek kitchen with stainless steel appliances, quartz countertops, and soft-close cabinetry, flowing seamlessly into the living space—perfect for entertaining or unwinding. Retreat to the primary suite with a spa-like bathroom and generous closet space. Central A/C, in-unit laundry, and garage parking offer everyday convenience. The elevator building also includes a fitness center, stylish common lounge, and professional management. Located just moments from sandy beaches, shops, and dining, with easy access to downtown Boston—The Somerset is where coastal living meets city convenience.

10 Somerset Unit 206, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
54 Wilshire St, Winthrop
$530,000
73490066 MLS
Rare Winthrop duplex development opportunity offering the chance to build ground-up new construction in a highly desirable coastal community. The project allows for two spacious 2,500+ sqft units, ideal for resale as luxury condos or as long-term income-producing properties. Each unit includes two off-street parking spaces, a valuable amenity in this sought-after location. With strong buyer demand and limited new inventory in the area, this is a prime opportunity for builders, investors, or owner-occupants looking to create value. Whether you plan to sell both units or hold for rental income, the flexibility and upside potential make this a standout project.

54 Wilshire St, Winthrop

Listing courtesy of Listing Agent: Lou Markakis from Listing Office: Lynnway Associates.
10 Somerset Unit 408, Winthrop
$530,000
1 Beds ⋅ 1 Baths ⋅ 73401776 MLS
Welcome to Unit 408 – a spacious 1-bedroom + den home at The Somerset, Winthrop’s newest boutique condo community blending coastal charm with modern comfort. This thoughtfully designed layout offers an open-concept living space, a versatile den ideal for a home office or guest room, and a walk-in closet in the bedroom. Enjoy upscale finishes throughout—quartz countertops, stainless steel appliances, central A/C, and sleek modern details. The Somerset is an elevator building featuring a fitness room, resident lounge, and garage parking. Located in the heart of Winthrop, just minutes from beaches, neighborhood shops, and an easy commute to downtown Boston. Schedule your tour today— and see why so many are choosing The Somerset as their new home.

10 Somerset Unit 408, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
10 Somerset Unit 211, Winthrop
$505,000
1 Beds ⋅ 1 Baths ⋅ 73376494 MLS
Welcome to The Somerset—Winthrop’s newest boutique condo development! This collection of 29 thoughtfully designed homes offers studios, 1-bed, 1+ bed, and 2-bedroom layouts with quality finishes and a coastal vibe. Enjoy open-concept living, stainless steel appliances, quartz countertops, central A/C, and stylish modern touches. Most units include garage parking, and select homes feature private decks. The elevator building also offers a fitness room and a welcoming common area—perfect for relaxing or enjoying a coffee. Ideally located in the heart of Winthrop, just a short distance from sandy beaches, local shops, and an easy commute to downtown Boston.

10 Somerset Unit 211, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.
2 Edgar Terrace Unit 3, Winthrop
$480,000
2 Beds ⋅ 1 Baths ⋅ 73567471 MLS
With modern qualities and the charm and character of a classic home, this two bedroom, one bath condo in an ultra convenient Winthrop location is a true hidden gem. Tucked away from the street and perched on the top floor, this spacious and breezy condo offers an updated kitchen with brand new stainless steel appliances, completely refurbished hardwood floors throughout, Harvey windows, private outdoor space and deeded off-street parking complete with a garage. Private laundry, ample closet space - including a pantry, and custom woodwork round out some of the features this property has to offer. Great location - just steps to shops and restaurants in Winthrop Center, close to parks, beaches and all the Winthrop has to offer. Just minutes to Downtown Boston, Logan Airport and Points North. Incredible opportunity to get into Winthrop at a very competitive price - one of the best deals in town!

2 Edgar Terrace Unit 3, Winthrop

Listing courtesy of Listing Agent: Edward Deveau from Listing Office: Century 21 Mario Real Estate.
10 Somerset Unit 404, Winthrop
$420,000
1 Beds ⋅ 1 Baths ⋅ 73456763 MLS
Welcome to Unit 404 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed studio features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The Somerset offers exceptional amenities, including a fitness room, elevator, and a cozy resident lounge ideal for remote work or casual gatherings. Just moments from sandy beaches, waterfront parks, and local restaurants—with easy access to downtown Boston via the Blue Line or seasonal ferry—this home blends coastal charm with city convenience. Whether you’re seeking your next home or a seaside retreat, Unit 304 delivers style and a lifestyle by the sea. Schedule your tour today!

10 Somerset Unit 404, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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