Beach Real Estate, Homes, Condos for Sale in Winthrop, MA

3 Beds ⋅ 3 Baths ⋅ NEW Status ⋅ 73600505 MLS ⋅ 2,000 SqFt.

Only 1 unit left! You'll see the ocean from several rooms, and the staircase is stunning, with skylights bringing in lots of natural light. The first floor has an open concept living room, dining room and kitchen, plus a half bath, with a private deck right off the kitchen. On the second floor is the primary suite, with a large bedroom, an oversized shower, a stand-alone tub and an office space. The third floor has two more bedrooms and a full bath. The lower level has enough ceiling height to finish the basement and add extra square footage. The layout is amazing, with a private yard and a separate driveway, it lives like a single family. The only thing shared is the master insurance. Unit B is under agreement, this is your chance to get in and still pick your finishes. This unit is not to be missed. Amazing location, location, location!

28 Thornton Park Unit A, Winthrop

$899,900

NEW Status ⋅ 73600455 MLS

GREAT BUSINESS OPPORTUNITY! Bring your business to this 2-bay mechanic shop on a spacious 6,500 sq. ft. corner lot! This commercial property offers approximately 1,152 sq. ft. of interior space with 2 vehicle lifts, 15-foot ceilings, an office, and 2 half baths. The building features forced hot-air heating with a newer motor and pump installed approximately 6 months ago, 200-amp electrical service.

250- Washington Ave, Winthrop

$675,000

3 Beds ⋅ 1 Baths ⋅ NEW Status ⋅ 73600348 MLS ⋅ 1,354 SqFt.

At the end of a private way, you'll find this cozy, warm & inviting three bedroom single w/off street parking and big garage. You'll enjoy an enclosed porch in the rear of the house as you walk in from the driveway. The oak cabinet eat in kitchen has formica counters, laminate flooring & a piggy back washer/dryer. The full bathroom is off the kitchen. There are three more rooms on the first floor that are being used as a dining room, living room & kids room with natural wood flooring. Three bedrooms on the second floor w/high ceilings which make it light and airy. The small fourth room could be a study, walk in closet or potential bathroom. You get to choose how you want to use it. Access to the partial basement is from the outside bulkhead. Roof is 2002, gas hot water 2017, gas heat 2001, chimney liner 2015. The realistic price reflects the updates that this older home needs. Close to the 713 bus which takes you to the Blue Line as well as schools, shopping & center of Town. Concrete garage adds quite a bit of storage and driveway is enough parking for 2 cars with a potential 3rd spot on the side of the house.

25 North Ave, Winthrop

$699,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73599806 MLS ⋅ 2,053 SqFt.

Marry the location, original trim work and layout, date the finishes. 65 Sunnyside Ave is a classic single family home by the beach in Winthrop’s Cottage Park neighborhood, set away from through traffic and directly across from Fishermen’s Bend, a local nature peninsula with marshes and beach. The neighborhood is surrounded by marinas and yacht clubs, with easy access to Logan Airport and downtown Boston. The first floor offers a bright living room with a fireplace and bay window, a dining room with wainscoting charm, a half bath, and a kitchen with white cabinetry, stainless steel appliances and French doors to a covered deck. Upstairs are three bedrooms, including a generous primary bedroom with a large closet, plus a full bath and a private balcony. Hardwood floors run throughout, the full basement offers storage, and a two car tandem driveway with a Level 2 EV charger adds convenience. Some rooms are ready for your updates, a chance to add value and make the home your own. Check out the virtual tour for examples of efficient finish upgrades.

65 Sunnyside Ave, Winthrop

$730,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73599589 MLS ⋅ 1,406 SqFt.

Welcome to 9 Lincoln St in Winthrop, MA. This traditional single-family residence is move in ready. Beyond its classic silhouette, this property serves as a refined backdrop for a life of comfort and effortless hosting. The kitchen serves as the heart of the home, featuring durable stone counters and a functional peninsula perfect for morning coffee or casual meal preparation. The matching black appliances offer a cohesive, modern aesthetic that blends seamlessly with the home’s traditional roots. The living room invites relaxation with a fireplace that acts as a natural focal point. Detailed built-in shelves provide organized display space, while the rich hardwood flooring adds a sense of warmth and continuity throughout the primary gathering area. The bedrooms continue the refined aesthetic of the home, each finished with hardwood flooring that provides a clean and classic foundation for your personal style. The property has one full bathroom on the 2nd floor and one half bathroom on the main level to accommodate your daily routine. Enjoy bonus space in the partially finished lower level perfect for a family room or home office. Outside, the property maximizes your lifestyle potential with a private outdoor living space with a low maintenance turf yard. Whether you are enjoying a quiet evening watching the sun set over the harbor on the covered front porch or greeting the day with a coffee on your private back deck, the exterior layout ensures you can fully engage with the fresh air and surroundings. This residence offers a rare opportunity to secure a much-loved home that is ready for its next chapter.

9 Lincoln St, Winthrop

$835,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73597515 MLS ⋅ 2,424 SqFt.

COASTAL LIVING WITH INCREDIBLE POTENTIAL! This two family duplex is a must see for any contractor, savvy buyer or owner occupant looking to build equity with improvements. Each side features three levels of living space; three bedrooms, 1.5 bathrooms, in-unit laundry hook ups and separate utilities. Off street assigned parking for two cars and on street with a permit. Ideally located just steps to the ocean, public transportation to the Blue Line, and fun eateries. Whether you envision converting the property into two individual condos, living in one while collecting rental income from the other or adding this property to your investment portfolio, the possibilities are worth exploring, This two family needs updating and the asking price reflects the work needed. Bring your vision and unlock the potential.

11-15 Sturgis Street, Winthrop

$365,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73597184 MLS ⋅ 782 SqFt.

A corner unit with a private balcony, this inviting 2-bedroom, 1-bath condo offers comfortable, low-maintenance living in one of Greater Boston’s most desirable seaside communities. Enjoy a bright, functional layout with flexible living space and the added benefit of outdoor enjoyment. Just minutes from Winthrop’s beautiful beaches, local restaurants, shops, and cafés, with convenient access to Boston. Whether you’re a first-time buyer, downsizing, or looking for coastal living, this is a wonderful opportunity to make Winthrop home!

200 Governors Dr Unit 19, Winthrop

$865,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73596710 MLS ⋅ 1,806 SqFt.

Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy Boston access. Unit is listed for sale and lease!

1001 Shirley St Unit 2, Winthrop

$649,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73596573 MLS ⋅ 1,515 SqFt.

Coastal charm. City connections. Welcome to Winthrop. Set in this oceanside community with convenient access to Logan Airport and downtown Boston, 19 Beal Street pairs classic colonial character with modern living. Hardwood floors, an original staircase, and arched doorways bring warmth to the main level, which includes a bright enclosed front porch and dining room. The eat-in kitchen offers oak cabinetry, a gas range, a breakfast bar, and a sun-filled dining area. Upstairs are three bedrooms and a full bath, while the finished lower level adds a family room, a second full bath, and a kitchenette. An elevated deck overlooks the private fenced yard with a fire pit. Enjoy Winthrop's beaches, Ingleside Park, the Deer Island walking path, and the shops and dining of Winthrop Center, with the Blue Line and Winthrop ferry offering connections to Boston. A coastal setting with the city within reach, don't miss your opportunity to experience this special town.

19 Beal St, Winthrop

$889,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73596305 MLS ⋅ 2,916 SqFt.

Welcome to 115 Read Street! Experience the perfect blend of modern luxury, style, and convenience in this stunning new construction townhouse style condominium in the heart of Winthrop! This beautifully designed 3-bedroom, 2-bath residence offers a spacious, open-concept floor plan featuring a sun filled living area, elegant dining space, and a gorgeous kitchen complete with top of the line appliances and quality finishes throughout. Enjoy the warmth and ambiance of electric fireplaces, generously sized bedrooms, and the comfort of your own private entrance. Thoughtfully designed across multiple levels, this home offers the ideal combination of space, functionality, and privacy. Additional features include off street parking, separate basement storage, and beautifully landscaped grounds. Ideally situated just minutes from Winthrop's beautiful beaches, local restaurants, shops, and downtown Boston, this exceptional property offers the best of coastal living with easy access to the city. Don't miss this incredible opportunity to own brand new construction in one of Winthrop's most desirable communities!

115 Read St Unit 2, Winthrop

$869,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73596306 MLS ⋅ 1,925 SqFt.

Welcome to 115 Read Street! Experience the perfect blend of modern luxury, style, and convenience in this stunning new construction townhouse style condominium in the heart of Winthrop! This beautifully designed 3-bedroom, 2-bath residence offers a spacious, open-concept floor plan featuring a sun filled living area, elegant dining space, and a gorgeous kitchen complete with top of the line appliances and quality finishes throughout. Enjoy the warmth and ambiance of electric fireplaces, generously sized bedrooms, and the comfort of your own private entrance. Thoughtfully designed across multiple levels, this home offers the ideal combination of space, functionality, and privacy. Additional features include off street parking, separate basement storage, and beautifully landscaped grounds. Ideally situated just minutes from Winthrop's beautiful beaches, local restaurants, shops, and downtown Boston, this exceptional property offers the best of coastal living with easy access to the city. Don't miss this incredible opportunity to own brand new construction in one of Winthrop's most desirable communities!

115 Read St Unit 1, Winthrop

$379,000

ACTIVE Status ⋅ 73596053 MLS

Build your Point Shirley home on a lot that already has Winthrop Zoning Board approval for a single family. The zoning work is finished, so you can go straight to design and permitting. Go up two or three stories and the upper floors open to ocean views and a clear line to the Boston skyline. Mornings on the water, evenings watching the city lights, and Logan and downtown Boston only minutes away. Located beside 54 Otis St. Also offered as land MLS 73594294. Fully approved lot for single family build, variance recorded with registry of deeds.

Lot 190 Otis Street, Winthrop

$629,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73595832 MLS ⋅ 1,166 SqFt.

HOME SWEET HOME! Are you ready to become a homeowner in the coastal Town of Winthrop? This well-priced, move-in ready Cape offers two bedrooms, a separate study, one full bath, dining room and an eat in kitchen. Situated on a 3,313 sq. ft. lot, this property also features off-street parking and a convenient location close to schools, shopping, Ingleside Park and the center of Town. With bus service to the Blue Line right on the corner, this home offers comfort, convenience and excellent value. Whether you're a first time homebuyer, downsizing or looking for a home to make your own, 96 Marshall St. is an opportunity you won't want to miss!

96 Marshall Street, Winthrop

$625,000

3 Beds ⋅ 2 Baths ⋅ CONTINGENT Status ⋅ 73595787 MLS ⋅ 1,281 SqFt.

This wonderful seaside home is ready to welcome its next owner! Located less than a block from Winthrop Beach, this lovingly updated single-family home blends modern style with warmth, comfort, and functionality. The stylish granite-topped kitchen features stainless steel appliances and an island, creating an inviting space for everyday living. Outdoor enjoyment is just as appealing, with a private yard offering room to relax, enjoy the outdoors, and take advantage of ample storage space. A welcoming porch extends the living area and provides a seamless connection between indoor and outdoor spaces. Ample parking is a bonus, including a second driveway. Enjoy the best of beachside living in a fantastic location and community just steps from the beach. Easy to show—don’t miss this opportunity!

17 Hawthorn Ave, Winthrop

$849,000

6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73595333 MLS ⋅ 1,920 SqFt.

Work and Relax from one Prime location in Winthrop - between 2 great beaches, with proximity to the Orient Heights blue line MBTA subway to the airport and downtown Boston, and quick access to Route 1A to I-90 and I-93. Recently renovated 2-Family with new eat-in kitchens, stainless steel appliances, granite countertops, new bathrooms, new decks. The upper unit has 3 bedrooms, 1 bathroom, direct access deck from sliding patio doors off the kitchen - perfect for the alfresco meal and beverages; the first first floor unit has 2 bedrooms, 1 bathroom, rear deck out the common corridor. Separate electric & gas/heat. Just a mile to each beach, either Donovan beach or Winthrop beach, public amenities, golf course, boat club, and so much more. Great for an owner occupant and have your tenants pay your mortgage, or a pure investment, or both. Showings limited to open houses only - next being Sunday Nov 8, 12p-1pm.

50-52 Bowdoin St, Winthrop

$379,000

ACTIVE Status ⋅ 73594294 MLS

Buildable lot beside 54 Otis St with Winthrop Zoning Board approval for a single family home. Build up and the second and third floors deliver ocean views plus a direct line to the Boston skyline. The zoning work is done, so a buyer can move straight to permitting. Minutes to Logan and downtown Boston. Also listed as a single family as separate MLS. Fully approved lot for single family build, variance recorded with registry of deeds.

Lot 190 Otis Street, Winthrop

$509,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73594243 MLS ⋅ 1,256 SqFt.

Top-floor, two-level 3 bed / 2 full bath a short walk from Winthrop Beach, fully refreshed in 2026: refinished hardwood, new paint throughout, renovated main-level bath, refinished kitchen cabinets. The main floor opens from a sunny living room into a white kitchen with recent stainless appliances, stone counters, pressed-tin ceiling and a pantry closet, with a back door to the rear deck. Two bedrooms and a full bath complete this level. Upstairs is a skylit primary suite with its own full bath, built-in shelving and in-unit laundry. New windows, new skylights and a new roof take the big-ticket items off the table in this 1900 building, and the condo fee covers heat and hot water. No one above you, ocean glimpses from the front windows, pets welcome, and a dedicated off-street parking space so you never hunt for beach parking. Walk to the sand, Shirley St shops, restaurants, schools and the athletic fields; the bus to the Blue Line puts you downtown in about 25 minutes, and Logan is minutes away.

173-175 Shirley St Unit 6, Winthrop

$839,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73594196 MLS ⋅ 2,204 SqFt.

Welcome home to this spacious and versatile property featuring four generously sized bedrooms, a bonus room, and three full bathrooms! Designed to accommodate a variety of lifestyles, this home offers plenty of room to spread out, work from home, and entertain. The first floor features a large living room that flows seamlessly into the dining room, with direct access to the backyard. The updated kitchen boasts slate appliances, an island, and a wine refrigerator, while hardwood floors and a full bathroom complete this level. On the second floor, you'll find a flexible bonus room ideal for a home office, nursery, or additional living space, along with two generously sized bedrooms, an additional bedroom toward the rear of the home, and a full bathroom. The third floor offers even more possibilities, with a spacious area perfect for creating a private primary suite. This level already includes a full bathroom and dedicated laundry, making it an excellent opportunity to customize the space to suit your needs. Outside, enjoy a spacious driveway accommodating two to three vehicles and a fenced-in backyard perfect for entertaining, outdoor dining, or simply relaxing. Conveniently located near local bus service, coffee shops, restaurants, schools, and one of Winthrop's largest beaches, this home offers space, flexibility, and a fantastic opportunity to enjoy all that Winthrop has to offer!

23 Sagamore, Winthrop

$949,000

3 Beds ⋅ 4 Baths ⋅ CONTINGENT Status ⋅ 73594122 MLS ⋅ 2,000 SqFt.

ONLY 1 Unit Left! Welcome to 28 Thornton Park, a stunning new-construction luxury townhouse in the heart of Winthrop. Spread across three thoughtfully designed levels, this home blends timeless architectural character with the comfort and quality of brand-new construction, all just minutes from Boston. The lower level basement is great height and could be finished.The sun-filled first floor is made for living and entertaining. Graceful arches, custom details and walls of windows fill the open layout with beautiful natural light. The gorgeous living room features soaring cathedral ceilings and flows into the dining area and a chef's kitchen designed for everyday cooking and holiday gatherings alike. Large sliding doors open to the outdoors for easy indoor-outdoor living, and a convenient half bath completes the level. The second floor is home to a true primary suite, a peaceful retreat at the end of the day. A second bedroom and a full bath make this level ideal for family or guests. The third floor adds even more flexibility, with another bedroom, a full bath and a beautiful home office. It's perfect for working from home, a guest suite or a quiet creative space. The home is still under construction, which means you have the rare opportunity to choose your own finishes and make it truly yours. Estimated completion is February 2027.Winthrop offers the best of seaside living with unbeatable convenience. Enjoy miles of beaches, waterfront parks, scenic walking paths, the harbor and a charming town center with local shops and restaurants. Logan Airport is minutes away, and downtown Boston is easily reached by car, the Blue Line or the ferry, making it ideal for commuters and travelers alike.

28 Thornton Park Unit B, Winthrop

$979,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73593881 MLS ⋅ 2,666 SqFt.

Welcome to Winthrop Center. This well-maintained home combines quality craftsmanship with convenient access to the town center. Inside, sun-filled rooms and refined finishes create a cohesive, inviting feel. Spacious gathering areas provide room to entertain, and the home is move-in ready. Nearby, enjoy conservation trails, beach access, shopping, dining, and major commuting routes. This home offers a blend of character, quality, and town-center convenience.

316 Bowdoin St, Winthrop

$989,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73592852 MLS ⋅ 2,180 SqFt.

FULLY GUT-RENOVATED IN 2026 | SINGLE-FAMILY WITH ADU | INCREDIBLE INCOME POTENTIAL! A rare opportunity to own a beautifully renovated home with a separate accessory dwelling unit (ADU) in one of Winthrop's most desirable neighborhoods! Completely gut-renovated in 2026, this unique property offers the feel and convenience of new construction with exceptional flexibility for homeowners and investors alike.The main residence features 2 bedrooms, 2 full bathrooms, a basement, and in-unit laundry. The ADU offers 1 bedroom plus a bonus room, 1.5 bathrooms, in-unit laundry, and two private decks. Two off-street parking spaces behind the property provide added convenience. Location is another standout feature! Situated just around the corner from Winthrop High School, Winthrop Middle School, and the golf course, this property offers incredible convenience in an established neighborhood. Imagine living in one unit while renting the other to help offset today's higher mortgage payments. With the schools just steps away, the ADU could be especially appealing to a local teacher or school employee seeking a convenient commute!Whether you're looking for multigenerational living, additional rental income, or the opportunity to rent both units as an investment, the possibilities are exciting. Two distinct living spaces, a complete 2026 renovation, off-street parking, and a prime Winthrop location make this a truly unique opportunity.

44 Bowdoin Street, Winthrop

$325,000

2 Beds ⋅ 1 Baths ⋅ PRICE CHANGED Status ⋅ 73592520 MLS ⋅ 772 SqFt.

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

$749,974

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73592145 MLS ⋅ 2,520 SqFt.

Attention investors, builders, and contractors! A truly rare opportunity awaits at 104-106 Shirley Street, Winthrop. Situated on an impressive double lot spanning over 10,000 square feet, this property offers incredible upside and potential. The existing home features some fire damage, allowing buyers the flexibility to perform selective renovations, execute a partial demo, or complete a full renovation to suit their vision. Double lots of this footprint are nearly impossible to find in Winthrop, making it an ideal project for tradespeople, savvy investors and whoever looking to add substantial value. Located just minutes from beaches, shops, dining, transit, and a short commute into Boston and Logan Airport, the site and scale are exceptional. Property is being sold strictly in AS-IS, WHERE-IS condition with all faults. Seller or broker make no representations or warranties, express or implied. Buyer to perform all due diligence regarding condition, zoning, permits to able to build , and scope of work

104-106 Shirley St, Winthrop

$425,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73591648 MLS ⋅ 861 SqFt.

Move right into this beautifully updated two-bedroom, one-bath condominium at 29 Seafoam Ave, located less than 500 feet from Winthrop Beach. Recent upgrades include a fully renovated bathroom, fresh interior paint, updated kitchen, and newly refinished hardwood floors, offering a turnkey opportunity from day one. The move-in ready home also features dedicated laundry, direct access to an exclusive-use covered front and side porch, access to a shared backyard, and assigned parking for two vehicles, a rare find in this coastal community. Positioned in a recreation-lover's paradise, this property is just half a mile from the Winthrop Golf Club and Boston Tennis, and under a mile from the Winthrop Yacht Club, boat ramp, and the convenient ferry serving Central Wharf, Logan Airport, and the Seaport. With local restaurants, cafes, and ice cream shops just around the corner, this low-maintenance coastal gem is perfect as a primary residence, seaside retreat, or a sharp addition to any real estate portfolio.

29 Seafoam Ave Unit 1, Winthrop

$498,500

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73591582 MLS ⋅ 1,002 SqFt.

This is your chance to live in Winthrop by the sea. This condo is located in a section of Winthrop known as Point Shirley. This condo is surrounded by amenities. The MBTA. bus to Boston or Logan airport stops directly across the street from your front door at the same place the local school bus stops. Winthrop also has a MBTA. water taxi to Boston. It's a fun ride across Boston harbor. The town beach is only a two-minute walk. Just grab your gear leave the car home and have fun. The neighborhood is great for walking and biking either on the beach or on Grandview ave. You will have on site parking plus curbside parking. Winthrop has three yacht clubs two boat marinas and a golf course. It also have public parks with tennis and basketball and a free boat launching ramp.

1020 Shirley St Unit 1020, Winthrop

$519,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73590903 MLS ⋅ 1,374 SqFt.

Welcome to 23 Trident Avenue, Unit 1, in the desirable seaside community of Winthrop! This spacious first-floor condominium offers approximately 1,374 square feet of living space, featuring 7 rooms, 3 bedrooms, 1 full bathroom, and a versatile bonus room ideal for a home office, creative space, or additional flex space. Thoughtful improvements by the current owner include a new refrigerator, garbage disposal, ceiling fans, bathroom was repainted, and updated light fixtures. Additional highlights include TWO off-street parking spaces and convenient basement storage, providing valuable extra room for your belongings. Enjoy all that coastal living has to offer with nearby beaches, local restaurants, shops, and convenient access to Boston. Whether you’re searching for your first home, need additional living space, or are looking to enjoy the charm of Winthrop, this property offers a wonderful opportunity. Don’t miss your chance to make this condo your own. Schedule your showing today!

23 Trident Unit 1, Winthrop

$665,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73589094 MLS ⋅ 1,413 SqFt.

Welcome to 14 Irwin Street, a charming single-family home in one of Winthrop’s inviting residential neighborhoods. Offering approximately 1,413 square feet of living space, this classic two-story home features 3 bedrooms, 1.5 bathrooms, and 7 total rooms, providing a comfortable foundation for your next chapter. Enjoy the best of Winthrop’s coastal lifestyle with the beach just a short walk away at the end of the street. Plus, with a bus stop just steps away, public transportation is conveniently accessible for an easier daily commute. From morning walks by the water to summer afternoons at the beach, this location makes everyday living feel a little more special. Set on an approximately 4,792-square-foot lot, this home offers room to grow and plenty of opportunity to make it your own. Built circa 1900, the property retains the character of an earlier era while inviting buyers to bring their own vision and personal style. Whether you’re looking for a family home or a place to create lasting memories, 14 Irwin Street offers a wonderful opportunity in a desirable seaside setting. A wonderful combination of coastal charm, convenient public transportation, and neighborhood appeal—truly a must-see property!

14 Irwin St, Winthrop

$1,250,000

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73588891 MLS ⋅ 3,420 SqFt.

Fantastic 3-Family Opportunity in Winthrop Center! Well-maintained and with recent updates, this multi-family property offers an excellent opportunity for investors and owner-occupants alike. The property features a 1-bedroom lower-level unit, a spacious 2-bedroom unit with two bonus flex rooms, and a 3-bedroom unit with two additional flex spaces. Recent improvements include replacement windows, updated electrical, interior and exterior painting, bathroom upgrades, new fencing, landscaping enhancements, soffit and gutter repairs, heating system updates, and added off-street parking. Select units enjoy private outdoor space and all units offer laundry. Ideally located just moments from Winthrop Center's shops, restaurants, beaches, and public transportation. A turnkey investment with strong income potential in one of Winthrop's most desirable neighborhoods.

23-25 Fremont St, Winthrop

$449,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73588727 MLS ⋅ 623 SqFt.

NEW CONSTRUCTION WITH GARAGE PARKING — JUST ONE BLOCK FROM WINTHROP BEACH! Opportunities like this are increasingly difficult to find. This is not a dated condo or a quick cosmetic renovation. 140 Shirley Street is true ground-up construction, designed and built by a reputable local builder with quality, durability, and long-term value in mind. Enjoy modern finishes, low-maintenance living, and the peace of mind that comes with new construction—all without the typical new-construction price tag. Enjoy easy access to Winthrop Beach, local restaurants, shops, and waterfront amenities, while downtown Boston is just a short commute away. It’s the perfect combination of coastal living and city convenience. New construction. One bedroom. Garage parking. One block to the beach.

130 Shirley Street Unit 8, Winthrop

$599,900

1 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73588722 MLS ⋅ 1,005 SqFt.

Oceanfront living at One Seal Harbor! Welcome to this beautifully renovated 1-bedroom, 1-bath condominium offering breathtaking ocean views from the living room, dining room and bedroom. Tastefully updated throughout, this inviting home features a bright and open living space designed to take full advantage of its stunning coastal setting. Step out onto your private deck and enjoy sweeping views of the ocean. The spacious bedroom offers a generous walk-in closet, while the convenience of in-unit laundry adds to the ease of everyday living. Additional amenities include one deeded garage parking space, private storage, fitness center, sauna, game room and concierge service. Ideally located just moments from Winthrop Beach, local restaurants, shopping, and all that Winthrop has to offer. Enjoy easy access to Boston and Logan international Airport while coming home to the peaceful beauty of oceanfront living. A wonderful opportunity to enjoy a low-maintenance coastal lifestyle in a desirable Winthrop location!

1 Seal Harbor Rd Unit 601, Winthrop

$599,900

5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73588699 MLS ⋅ 2,200 SqFt.

Two-Family Opportunity Near the Beach! Located in desirable Winthrop, this two-family property offers an exciting opportunity to build equity in a sought-after coastal community—all for under $600,000. This fixer-upper is ready for someone with vision to bring it back to life and unlock its full potential. Whether you’re an investor looking for your next project or a buyer willing to put in the time and effort to create value, this property offers plenty of possibilities. Enjoy the convenience of being close to the beach, local shops, restaurants, and transportation while taking advantage of the income potential and flexibility a two-family home provides. A great opportunity to renovate, customize, and create lasting value in Winthrop!

91 Fremont St, Winthrop

$799,900

5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73587974 MLS ⋅ 2,437 SqFt.

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. Perfect ADU potential or in-law space in the lovingly finished and conveniently laid out walk out lower level with an oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, a laundry area. Complete with a bedroom and a full sized cedar closet, this is the home for you! Walk out your lower level door to a covered area for a table or another sitting area. 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

$491,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73587738 MLS ⋅ 691 SqFt.

Welcome to The Somerset unit 205, an elevated boutique condominium in the heart of Winthrop, where refined modern living meets a relaxed coastal lifestyle. This beautifully designed 1+ bedroom, 1-bath residence features an open-concept layout with sophisticated finishes, including a sleek kitchen with quartz countertops and stainless steel appliances. Central A/C and elevator access add everyday comfort, while the building’s fitness room and inviting common area create an effortless sense of community. Ideally located near Winthrop’s beaches, waterfront, shops, restaurants, and cafés, The Somerset offers a stylish coastal retreat with convenient access to downtown Boston.

10 Somerset Unit 205, Winthrop

$1,095,000

4 Beds ⋅ 3 Baths ⋅ SOLD Status ⋅ 73587151 MLS ⋅ 2,910 SqFt.

Stunning home in the heart of Winthrop. This exceptional American Foursquare combines timeless architectural character with extensive renovations and modern finishes throughout. Spacious and sun-filled, the home offers beautifully remodeled interiors, off-street parking, and exceptional indoor/outdoor living while preserving its classic craftsmanship. A newly remodeled mudroom with custom storage, new windows, and recessed lighting opens to a gracious living room with hardwood floors and a gas fireplace with a newly constructed surround. The spacious dining room features traditional wainscoting and an elegant setting for entertaining.The fully remodeled kitchen is the centerpiece of the home, featuring a large center island, custom cabinetry, designer tilework, new flooring, and generous workspace. An expansive Trex deck overlooks the fully fenced, professionally landscaped 6,000 sq. ft. lot, creating an exceptional setting for outdoor dining and entertaining. A full bath completes the main level.The second floor offers three generously sized bedrooms, and fourth bedroom currently being used as a home office. A fully remodeled bath with new finishes and fixtures caps off the second floor. The finished third floor provides flexible bonus space ideal for an office, guest retreat, media room, playroom, or library.The newly finished lower level offers a separate in-law suite with a brand-new kitchenette, second gas fireplace featuring hand-built stonework, half bath, dedicated gym, and laundry area—ideal for extended family, guests, or additional work-from-home space. Short distance to schools, Town Center restaurants and cafés, shops, the library, parks, and beaches, with convenient access to Boston, the Seaport, Financial District, and Logan Airport.

61 Read Street, Winthrop

$540,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73586927 MLS ⋅ 1,295 SqFt.

Welcome to this immaculate top-floor corner condo in Chase Condominiums, where privacy, natural light, and effortless one-level living come together beautifully. Abundant corner windows fill the spacious home with light while offering a peaceful sense of privacy. The generously sized primary suite features an updated en-suite bath with a tiled shower, Jacuzzi tub, and walk-in closet. The second bedroom offers its own private bathroom and tall, bright windows. An open-concept layout seamlessly connects the living and dining areas, creating endless possibilities for entertaining, relaxing, and everyday living.The updated kitchen features granite countertops, tall cabinetry, stainless steel appliances, and a brand-new washer and dryer. Step outside to your large private deck—perfect for morning coffee, outdoor dining, or simply enjoying your own private outdoor retreat. Extra Storage unit is deeded with the unit(#5), along with 1 deeded parking spot (#14)The well-maintained complex offers an inviting shared roof deck with ocean views, tables, comfortable seating, and seasonal décor. It’s an exceptional spot to take in the Fourth of July fireworks over Boston or from Winthrop High School. Enjoy beautifully landscaped grounds and a convenient location just moments from marsh trails, playgrounds, dog parks, and access to Winthrop Beach. With its spacious floor plan, abundant natural light, private outdoor spaces, and fantastic coastal lifestyle, this condo offers the perfect blend of comfort, convenience, and privacy.

15 Ocean Unit 206, Winthrop

$569,000

2 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73585619 MLS ⋅ 1,692 SqFt.

Opportunity awaits at 16 Loring Road in Winthrop! This 6-room home offers 2 bedrooms and plenty of potential for buyers looking to renovate, customize, or invest. The property features oil heat, an unfinished basement with convenient walkout access, and a detached two-car garage offering additional parking and storage. Situated on an approximately 5,500 sq. ft. lot. Bring your ideas and vision to unlock the possibilities this property has to offer. Property is being sold strictly AS-IS. Seller makes no representations or warranties regarding the property or its condition. Buyer and buyer’s agent are responsible for conducting their own due diligence and verifying all information to their satisfaction.

16 Loring Rd., Winthrop

$1,275,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73585487 MLS ⋅ 2,599 SqFt.

Welcome to your ultimate beachfront oasis in Winthrop, where every day feels like a permanent getaway with direct access from your back door straight into the sand. This stunning home features an inviting, fireplaced living room, a kitchen boasting sleek marble countertops and tile flooring, a convenient main-floor full bath and an outdoor shower for rinsing off after the beach, and two flexible bedrooms ideal for guests, children, or a home office. Take in breathtaking ocean sunrises over morning coffee from the year-round heated sunroom, and retreat upstairs to a spacious primary suite complete with its own private bath. The finished lower level functions as a fully separate suite—an incredible asset as one of only 10 legal Airbnbs in all of Winthrop, complete with its own family room, bonus space, full bathroom, and laundry. Positioned in an unbeatable location with two off-street parking spots and an EV charger, this property sits less than 1 mile from the Winthrop Landing MBTA ferry for easy transit to Logan, Central Wharf, and the Seaport, perfectly balancing everyday coastal luxury with elite short-term rental potential.

129 Strandway, Winthrop

$549,995

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73585000 MLS ⋅ 1,614 SqFt.

Ocean views, salty breezes & beachside living just minutes from Boston! This bright 2-bedroom, two-level condo offers direct ocean views & a deeded patio exclusive to the unit. Across the street, enjoy the beach & a 2-mile walking trail, perfect for morning strolls. Abundant windows fill the open-concept living space with natural light, while a 3 sided gas fireplace adds warmth & charm to the center of the entertaining space. The updated and spacious eat-in kitchen features newer appliances, a coffee bar, and bar seating. Wake up to ocean views in the primary bedroom, complete with a walk-in closet! The updated bath offers a spacious shower & jetted tub with a unique ceiling-mounted water feature and a large steam shower. The lower level adds flexibility with a bonus room, separate office & ample storage. Deeded parking, in-unit laundry, central A/C, a new hot water heater & newer HVAC complete the package. Sip coffee on your deck, unwind to the sounds of waves & seagulls, & make every day feel like a vacation!

54 Trident Ave Unit 54, Winthrop

$339,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73584904 MLS ⋅ 811 SqFt.

Welcome to 900 Governors Dr, Unit 37, Winthrop, MA, where easy condo living meets the charm of one of Greater Boston’s most desirable seaside communities. Just minutes from the water, this inviting 2-bedroom, 1-bath condo offers a bright, comfortable interior, a functional layout, and the low-maintenance lifestyle today’s buyers are looking for. Whether you’re a first-time buyer ready to make the move from renting to owning, a downsizer looking for simplicity, or someone who wants to live close to Boston while enjoying a coastal setting, this home offers an excellent opportunity. Inside, you’ll find comfortable living space with plenty of flexibility for everyday life. The two bedrooms provide options for a primary bedroom, guest room, home office, or additional living space. The thoughtful layout makes the condo feel welcoming and functional while still offering the opportunity to add your own personal style. One of the biggest advantages is the convenience of condo living. Spend less time worrying about exterior maintenance and more time enjoying everything Winthrop has to offer. Outside you will experience the lifestyle that makes this location so appealing. Winthrop’s beaches and shoreline are just minutes away, along with local restaurants, shops, cafés, and everyday conveniences. And with Boston only a short commute away, you can enjoy the best of both worlds — the relaxed atmosphere of a coastal community with easy access to the city. Move-in ready, conveniently located, and full of potential, Unit 37 is ready for its next owner. Come experience Winthrop living and see what makes 900 Governors Dr so wonderful.

900 Governors Dr Unit 37, Winthrop

$649,900

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584839 MLS ⋅ 1,925 SqFt.

A rare opportunity to own a spacious Folk Victorian cherished by the same family for four generations. Tucked away on a quiet dead end street, this 1,925 sq. ft. home welcomes you with a classic screened front porch and an impressive amount of living space inside. The expansive first floor features open concept living and dining with parquet floors and a built in serving cabinet, plus an oversized kitchen with plenty of cabinet and counter space, stainless steel appliances, a gas range and 10 foot ceilings waiting to be revealed. A spacious den with a freestanding gas stove offers another inviting gathering space, along with a full bath and first floor laundry. Sliders lead to the deck and backyard, where an in ground pool and patio with gazebo create a fantastic setting for summer entertaining. Upstairs are three generously sized bedrooms and a second full bath, with one bedroom opening directly onto a flat roof offering potential for a future deck or expansion. The finished third floor adds flexible space for a den, office or playroom, plus ample storage. Central heat and A/C and three car tandem parking add everyday comfort and convenience. Bring your vision and make this special home your own, with Winthrop’s coastal setting right outside your door, a short walk to Fisherman’s Bend, close to Winthrop Center, and minutes from Logan Airport and downtown Boston. Open House, Saturday 10/3 10:30 -12pm, Sunday 10/4 10:30 - 12pm

16 North Ave, Winthrop

$637,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73584622 MLS ⋅ 1,233 SqFt.

Introducing Unit 307 at Somerset Winthrop, where refined design, modern convenience, and effortless comfort come together in a beautifully appointed residence. Ideally situated in the heart of Winthrop, this spacious 2-bedroom, 2-bath home offers an inviting retreat just moments from local shops, restaurants, and neighborhood amenities.The thoughtfully designed interior features an open-concept living space and a modern kitchen appointed with quartz countertops, stainless steel appliances, and a convenient breakfast bar. The private primary suite offers a generous walk-in closet, while the additional bedroom and full bath provide exceptional flexibility for guests, a home office, or everyday living. In-unit laundry adds to the ease and convenience. Residents also enjoy access to a well-equipped exercise room and meeting room, with carport parking. With its sophisticated finishes, generous living spaces, and prime Winthrop location, Unit 307 offers an exceptional opportunity to enjoy a polished, low-maintenance lifestyle.

10 Somerset Unit 307, Winthrop

$839,900

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584025 MLS ⋅ 1,942 SqFt.

Stunning single family home located in the desirable Town of Winthrop. This completely updated and spacious single family home offers four bedrooms with one and a half baths and plenty of space for everyone. Additional bonus rooms on the attic level and a large unfinished basement provide even more opportunities for expanded living. An open floor plan and a beautiful kitchen, complete with stainless steel appliances and upgraded countertops make this a perfect home for entertaining. Hardwood flooring throughout, central forced air, and ductless mini-splits round out some of the great features this home has to offer. An ample and airy backyard and off-street parking are a huge plus. Incredible location - just steps to the ocean and minutes to Downtown Boston, Logan Airport and the North Shore. See all that Winthrop has to offer - close to beaches, parks, restaurants and much more!

32 Elmwood Avenue, Winthrop

$220,000

1 Beds ⋅ 1 Baths ⋅ SOLD Status ⋅ 73583670 MLS ⋅ 664 SqFt.

New price! Rare one bedroom unit in desirable 100 building at Governors Park entrance. Recently vacated by tenant of over 10 years. Short walk to local restaurants and shops, bus line to T.

100 Governors Drive Unit 2, Winthrop

$629,900

2 Beds ⋅ 1 Baths ⋅ PRICE CHANGED Status ⋅ 73582921 MLS ⋅ 1,144 SqFt.

Welcome to 7 Enfield Road, a captivating single-family residence in Winthrop, MA. Built in 1930, this inviting home spans 1144 square feet and is ready for you to move in. It offers a unique blend of classic charm and comfortable living, set on a generous 6969 square foot lot. The living room provides a warm and inviting atmosphere, centered around a charming fireplace, and features elegant hardwood flooring that extends throughout the space. The bedrooms, designed for comfort and tranquility, also boast classic hardwood flooring, creating a cohesive and timeless feel throughout the private areas of the home. This property also includes a convenient one-car garage, a full basement offering ample storage or potential for future customization, and a welcoming porch perfect for enjoying the outdoors. Discover the effortless lifestyle awaiting you at this charming Winthrop address. Convenient location to Winthrop Center and shopping, Cummings Elementary School or walk to Ingleside Park, tennis and basketball courts, pickle ball courts and Donovan's beach.

7 Enfield Road, Winthrop

$1,500,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73582288 MLS ⋅ 2,852 SqFt.

The street name—Harbor View Avenue—says it all! A home any sea captain would be proud to call home! Rare opportunity to own a distinctive multi-family property perched at one of Winthrop’s highest elevations, with sweeping panoramic views of the ocean and Boston Harbor and Skyline. Enjoy spectacular sunrises, sunsets, passing boats, and refreshing ocean breezes from this exceptional coastal setting. Classic Hardie Board siding adds timeless New England character, while public stairs just steps away provide convenient access to Yirrell Beach and its shoreline walks. The flexible multi-family layout offers excellent options for an owner-occupant, multi-generational living, or investment income. The current configuration also provides the potential to convert the property into a spacious four-bedroom single-family home. The owner is currently awaiting Massport approval for replacement windows and doors. Elevated location, exceptional ocean and harbor views, beach access, classic coastal character, and versatile living possibilities make this a truly special Winthrop property. Check out our video with the QR code or cut and paste this link: https://tour.vaulted-media.com/63_harbor_view_ave-4103

63 Harbor View Ave, Winthrop

$555,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73582183 MLS ⋅ 848 SqFt.

Welcome to The Somerset, Winthrop’s newest boutique condominium community. Unit 210 is a beautifully designed 1-bedroom, 1-bath residence offers modern living with a relaxed coastal feel. The open-concept floor plan features quality finishes throughout, including stainless steel appliances, quartz countertops, central A/C, and stylish contemporary details. The elevator building offers a fitness room and inviting common area for residents to enjoy. Most residences include garage parking, and select homes feature private decks. Ideally located in the heart of Winthrop, The Somerset is close to sandy beaches, local shops, restaurants, and everyday amenities, with convenient access to downtown Boston. Enjoy the ease of low-maintenance condo living in a vibrant coastal community just outside the city.

10 Somerset Unit 210, Winthrop

$449,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73582000 MLS ⋅ 805 SqFt.

Whether you’re buying your first home or looking to simplify your life with easy one-level living, this beautifully renovated and meticulously maintained 2-bedroom condo checks all the boxes! Located entirely on the first floor with no stairs required, the home offers a bright, open-concept layout filled with natural light and an easy, move-in-ready lifestyle, just minutes from Winthrop Beach. The updated kitchen features white shaker cabinetry, granite countertops, stainless steel appliances, peninsula seating and plenty of storage, opening seamlessly into the spacious living area. The living area boasts space for a large sofa and television plus an extra storage closet. The generous primary bedroom is bright and inviting, with a double closet. It’s complemented by a versatile second bedroom, ideal for remote work, guests, or a roommate to help offset the mortgage, or simply a nice, bonus flex space. An updated full bath, in-unit laundry and dedicated parking add the everyday convenience of this home! Outside, enjoy your own exclusive patio space, perfect for morning coffee, summer grilling or relaxing after a day at the beach. An excellent option for a first-time buyer, empty nester or downsizer seeking low-maintenance, single-level living without sacrificing a second bedroom or private outdoor space. Convenient to Boston, Logan Airport and all that Winthrop has to offer, this seaside gem is ready for its next owner!

43 Sagamore Ave Unit 1, Winthrop

$699,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73581893 MLS ⋅ 1,113 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 two-bedroom, two-bath 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 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.

130 Shirley Street Unit 250, Winthrop

$965,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73579972 MLS ⋅ 1,978 SqFt.

The largest residence in the Pearl, loft-style living, high ceilings, oversized windows, and original wood details. The layout offers flexibility, including space that works well for a home office. Premium kitchen, radiant-heated primary bath,2 off-street parking spaces, private storage, and secure entry. Close to beaches, trails, cafes, and an easy ride into Boston. Also being offered for SALE & LEASE!

1001 Shirley St Unit 1, Winthrop

$665,000

2 Beds ⋅ 2 Baths ⋅ SOLD Status ⋅ 73579929 MLS ⋅ 1,471 SqFt.

Penthouse-level two bedroom, two bath condominium at The Residences at the Atlantis Marina, a 44-unit elevator building on Winthrop's waterfront. West-facing with harbor views of the Boston skyline and nightly sunsets from a private covered balcony. Open layout with high ceilings, a granite kitchen with gas range and stainless appliances, in-unit laundry, central air, and wood floors. Two deeded parking spaces in the heated underground garage. Five miles from downtown Boston with quick access to Route 1A and Logan Airport, in a seaside community with beaches and parks close by.

550 Pleasant St Unit 510, Winthrop

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