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$1,175,000
6 Beds 4 Baths SOLD Status 73473241 MLS 4,062 SqFt.
In the sought after Winthrop HIGHLANDS you'll find this quality built THREE FAMILY home. This is your opportunity to become an owner occupied investor! Each unit features a comfortable layout with a generous amount of natural light and functional living spaces. The first floor has three bedrooms, second floor one and the third unit is on two levels with two bedrooms. The property has been well maintained and offers separate utilities, one off street parking space, and a nicely landscaped backyard. You'll enjoy beautiful ocean views and it's just steps to Halford Beach. Pride of ownership is evident throughout. Winthrop by the Sea is just six miles to Boston, has a variety of wonderful restaurants, walk/jog trails, access to the Blue Line and close to Logan Airport - 22 Upland Road is an outstanding opportunity to own a home and collect rental income in one smart investment,

22 Upland Road, Winthrop

$735,000
5 Beds 2 Baths SOLD Status 73470640 MLS 2,254 SqFt.
Located on a quiet, tree-lined street in the desirable Cottage Park district, this 5-bedroom, 1.5-bath single-family home offers seacoast city living at its best. Enjoy a lovely ocean-view park at the end of the cul-de-sac and a private beach just steps away. Inside, the home features beautiful hardwood floors, a fireplace, living and dining rooms, and a renovated kitchen. Outdoor highlights include a wraparound front porch, a spacious rear deck, brick patio in the back yard and a shed/garage ready for your renovation ideas. A new Rinnai wall-mounted hot water and central heating system, along with solar panels and new insulation, provides modern energy efficiency and savings. Don't miss all this home has to offer. Not located in a flood zone.

210 Woodside Ave, Winthrop

$995,000
7 Beds 2 Baths SOLD Status 73470613 MLS 2,604 SqFt.
AMAZING 2 family home that just was updated inside and out! THE LOCATION IS PERFECT side street loca in Winthrop Center & just 1/2 mile to the beach. It will be delivered vacant & ready to MOVE RIGHT INTO. The larger unit (2nd & 3rd Flr) has 4 bedrooms and it's own private rear deck & enclosed front porch. The 1st floor unit is 3 bedrooms & has it's own deck. All decks are maintenance-free composite decks, yard is fenced in, shed for storage, Beautiful lot with a new block wall, & more. Roof is newer, and all utilities are SEPERATE! One of the heating systems is a wall-mount gas Navien system! Washer & dryer hookups in each unit. All appliances are BRAND NEW - never been used. Although it is an older home with "older stuff" - you can move right in without even picking up a paint brush. Located within walking distance to coffee shops, restaurants, schools and parks offering both convenience and town center charm. SELLER PAYING FOR 1 YR HOME WARRANTY!

72 Fremont St, Winthrop

$449,000
1 Beds 1 Baths SOLD Status 73470307 MLS 611 SqFt.
Discover the perfect blend of modern design and seaside charm at 130 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom, one-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 double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking (with the option to purchase a second space). Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

140 Shirley Street Unit 240, Winthrop

$380,000
2 Beds 1 Baths SOLD Status 73469974 MLS 780 SqFt.
FINALLY!!! A Villager unit for sale in the sought after 100 Building! These 2 bedrooms in Governors Park has a renovated bathroom, newer windows and has been freshly painted. Best of all, Unit 118 is on the TOP FLOOR and features a balcony with views of the top of the Boston skyline, where you can also enjoy AMAZING sunsets. This complex features a clubhouse, gym room, in ground pool and tennis courts and is just a short walk from Winthrop beach. Walk across the street and go to the market, grocery store, bakery or to one of the many diverse and delicious restaurants this quaint town has to offer. Live here and live just 15 minutes to Downtown Boston or take the bus and in just 6 minutes you will be at Orient Heights train station. Condo fee INCLUDES heat & hot water. This one REALLY will not last!

100 Governors Drive Unit 118, Winthrop

$545,000
2 Beds 2 Baths SOLD Status 73467944 MLS 1,421 SqFt.
Victorian-inspired 2-bed, 1.5-bath condo offering 1,400+ sq ft across two levels, featuring two fireplaces (one outfitted with a working gas insert), one assigned off-street parking, and a sizeable backyard for rare outdoor space in Winthrop. An updated kitchen with vintage accents and quality craftmanship deliver timeless character —charm you simply can’t reproduce in today’s construction. The space immediately provides a single-family feel by opening to a generous living and dining area boasting ten ft. ceilings, with a well-suited half bath on the main level and a full bath adjacent to the primary bedroom. This home combines cozy ambiance and coastal neighborhood living in one standout residence. The property is located directly next to the historic library and near downtown Winthrop, with convenient access to coffee shops, a yoga studio, and local restaurants. HOA covers water, blanket insurance, and snow removal. The stairs and deck are brand new.

270 Winthrop Unit 2, Winthrop

$543,000
2 Beds 2 Baths SOLD Status 73466980 MLS 1,203 SqFt.
SELLER MOTIVATED! AMAZING VALUE! Enjoy the ease of COASTAL LIVING in this beautiful 2-bed, 2-bath unit designed for comfort and convenience. Filled with natural light, it offers an open layout and a private balcony with OCEAN VIEWS—perfect for morning coffee or sunset unwinding. The spacious primary suite includes an EN-SUITE BATH and a generous walk-in closet. FRESHLY PAINTED THROUGHOUT with NEW CARPET in the LR and primary bedroom, this MOVE-IN READY home includes ample storage and in-unit laundry. ENJOY MAINTENANCE FREE LIVING with 24/7 concierge, fitness center, garage parking, private storage, in-ground pool, tennis courts, and a penthouse great room with panoramic city and ocean views. Steps from the entrance, a seaside path leads to a charming gazebo for peaceful starts and finishes to your day. You've got it all and more!! Located on the WINTHROP COAST - MINUTES FROM BOSTON—this condo offers the perfect blend of COASTAL SERENITY and EVERYDAY CONVENIENCE.

1 Seal Harbor Road Unit 415, Winthrop

$815,000
5 Beds 4 Baths SOLD Status 73466654 MLS 2,550 SqFt.
Located in Winthrop’s highly desirable Point Shirley, this renovated single-family home offers generous living space, a flexible layout, and an unbeatable beachside location while still close to Boston & everyday conveniences.The main level features a renovated open floor plan with hardwood floors & tons of natural light, where living & dining flow seamlessly into a spacious, remodeled kitchen with granite countertops, upgraded cabinetry, stainless steel appliances, recessed lighting, shiplap details & a breakfast bar, perfect for everyday living or entertaining.Two bedrooms on the first floor offer added convenience, including a main bedroom with an en-suite full bath. Upstairs, you’ll find additional bedrooms & bathrooms, offering plenty of flexibility for home offices, guest rooms, or growing households, all featuring hdwd floors, natural lighting & ceiling fans. Enjoy Atlantic views, walks to the beach, off street parking & easy access to local amenities in this move-in-ready home.

993 Shirley St, Winthrop

$1,650,000
8 Beds 7 Baths SOLD Status 73465296 MLS 5,362 SqFt.
Deal fell through due to buyer's financing. Rare opportunity to own a spacious waterfront duplex offering versatility, income potential, and breathtaking coastal living just minutes from Boston and Logan Airport. This well-designed property features 4+ bedrooms with finished lower levels on each side, each offering three additional rooms--ideal for extended family, home offices, or flexible living space. With potential for an additional unit ADU(Accessory Dwelling Unit), this property presents an outstanding opportunity for multi-generational living or added rental income(buyer to perform due diligence). Two separate newer boilers , the convenience of a 2 car garage and ample storage, all while taking in serene water views and direct access to the shoreline lifestyle Winthrop is known for. Perfectly located near beaches, marinas, restaurants, and public transportation, this gem combines suburban coastal charm with unbeatable proximity to the city. Floor plans attached.

201-203 Cliff Avenue, Winthrop

$815,000
4 Beds 2 Baths SOLD Status 73464677 MLS 2,317 SqFt.
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

$450,000
1 Beds 1 Baths SOLD Status 73463015 MLS 620 SqFt.
This offering is about the land, the view, and the opportunity to own an affordable single-family property in an exceptional location. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready property sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing single-family structure is currently dilapidated and presents a buyer with two paths: restore the home or pursue new construction. Zoning Board of Appeals approval has already been granted, making this a fully entitled, shovel-ready opportunity. A buyer simply needs to pull a building permit and begin construction. Existing structure is intended for tear down. Zoning Board of Appeals approval has already been granted and the project is fully entitled.

86 Undine Ave, Winthrop

$1,140,000
6 Beds 4 Baths SOLD Status 73460507 MLS 3,400 SqFt.
Introducing coastal living in this luxurious two-family home set on one of Winthrop’s most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat. Enjoy updated electric, beautiful updated countertops, top-of-the-line appliances, new plumbing fixtures, sun-filled rooms, wood restored fireplaces, front/back porches, fenced in yard and flexible layouts designed for comfort and value. Coastal breezes, nearby beaches, marinas, and shoreline paths capture Winthrop’s coveted seacoast charm. A private 3–4 car driveway completes this versatile property—ideal as a luxury residence, premier investment, or both. Don’t miss this smart investment opportunity. More pictures coming soon!!

47 Bellevue Ave, Winthrop

$850,000
4 Beds 2 Baths SOLD Status 73460239 MLS 2,103 SqFt.
OPPORTUNITY KNOCKS.......Two family with large yard is located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! Some renovations as of 2001. The owner's unit is on the second and third floors with an open floor plan and lots of natural lighting. It contains a living room, dining area, kitchen, bath and one bedroom. The top floor consists of a sprawling main bedroom large enough to become 2 rooms. There are Boston skyline and marina views from the the top floor. The owner's unit has a great layout and good size rooms with lots of windows and laundry area of the kitchen. The first floor unit consists of a living room, kitchen, bath and two bedrooms. THIS IS A GREAT OWNER OCCUPY OR, INVESTMENT PROPERTY!

56 Main Street, Winthrop

$685,000
4 Beds 2 Baths SOLD Status 73460212 MLS 1,864 SqFt.
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

$1,600,000
5 Beds 4 Baths SOLD Status 73458947 MLS 3,866 SqFt.
Welcome to the Highlands, Winthrop’s most coveted neighborhood- where modern design meets sweeping Boston views. This newly renovated two-family sits high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main unit offers an open layout with living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area opening to a skyline deck. A first-floor bedroom, full bath, and mudroom add versatility. Upstairs features three bedrooms, including a luxe primary suite with Juliet balcony, walk-in closet, and spa bath with steam shower, soaking tub, heated floors, and double vanity.The lower-level one-bedroom unit includes its own kitchen, laundry, French doors to the yard, and private entrance—perfect for multi-generational living, au pair, or income. With a tiered backyard, three-car parking, and one of Winthrop’s premier addresses, this home blends sophistication, flexibility, and unmatched city views.

144 Quincy Ave, Winthrop

$580,000
2 Beds 2 Baths SOLD Status 73458762 MLS 1,141 SqFt.
Belle Mer is a newer built 16 unit condo association just on the outskirts of vibrant Winthrop Center, Nearby bountiful dining options, a best of North Shore boutique, coffee shops, fitness studios, book store, and unlimited conveniences. The unit is completely modernized with a timeless aesthetic. Seldom available,modern design 2 level floor plan with oversized windows, dramatic tall ceilings, exquisite appointments, 2 bedrooms, 2 bathrooms, charming window seats and ultimately desired PRIVATE front and back entries and assigned parking space 25. The association has curated wonderful professionally landscaped grounds creating a beautiful ambience nearby Boston Harbor. Hardwood floors, recessed lighting. Chef ready kitchen with Bosch appliances and fabulous island. In unit laundry. . 2 pets max. Easy access to Boston. Professionally managed. Your furry pet will love the harbor at low tide end of Woodside.

142 Pleasant Street Unit 12, Winthrop

$629,000
2 Beds 2 Baths SOLD Status 73458592 MLS 1,036 SqFt.
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

$420,000
1 Beds 1 Baths SOLD Status 73456763 MLS 546 SqFt.
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

$855,000
2 Beds 2 Baths SOLD Status 73456380 MLS 1,975 SqFt.
Penthouse Waterfront Luxury at Atlantis Marina – Oversized Boat Slip Included!Experience sophisticated coastal living in this stunning top-floor corner penthouse at Atlantis Marina, offering sweeping water views and panoramic Boston skyline vistas. This rare fifth-floor residence combines luxury, space, and an unbeatable location in the charming seaside town of Winthrop.This exceptional 2-bedroom, 2-bath home features an open-concept layout perfect for entertaining, complete with private deck overlooking the marina and city. Gourmet kitchen with stainless steel appliances, gas cooking, stone counters, and an oversized refrigerator. Gas fireplace, recessed lighting, and abundant natural light.In-unit washer/dryer and central heat/air conditioning. A highlight of this residence is the assigned large boat slip lease ideal for boating enthusiasts and available for use with a small yearly maintenance fee. Located just minutes from downtown Boston.This is coastal living at its finest

550 Pleasant St Unit 506, Winthrop

$362,500
2 Beds 1 Baths SOLD Status 73454898 MLS 1,092 SqFt.
Priced Well Below Market Price - Experience the best of coastal living just minutes from Boston—close to the city without the high prices! This bright and spacious home features soaring ceilings, abundant natural light, large rooms, and hardwood floors. The traditional dining room with a built-in cabinet adds classic charm, while the fully applianced kitchen offers warm wood cabinetry and an oversized pantry. Enjoy morning coffee or evening breezes on either of two private porches. Each unit includes its own washer and dryer in the basement, and the pet-friendly building is well-maintained with a low condo fee. Perfectly located near Winthrop’s beautiful beaches, scenic trails, and popular local restaurants. Priced to sell quickly—come see why this is the best value on the coast!

9 Atlantic St Unit 2, Winthrop

$1,050,000
4 Beds 4 Baths SOLD Status 73454724 MLS 2,575 SqFt.
Don’t miss this luxury oceanfront penthouse style condo with unbeatable views in one of Winthrop’s most sought after neighborhoods. Enjoy sunset views from BOTH your ocean private decks, perfect for relaxing or entertaining overlooking the Atlantic. Gutted & converted in 2022 from top to bottom, 191 Court has modern smart-home features including smart thermostats, WiFi-connected blinds, and Ring security system for comfort & energy efficiency. Take in the expansive floor plan beaming with sunlight & original restored hardwood floors throughout. The kitchen features top of the line smart appliances, a wine fridge & oversized island opening to the living room. Custom shutters & blinds hang on every window. Each bedroom features custom California closets, stunning on suites, and the main living space has a view of the ocean, no matter what window you look out. The current sellers have enjoyed living here for years, and you will too. Do not miss 191 Court Road!

191 Court Rd Unit 3, Winthrop

$719,000
3 Beds 2 Baths SOLD Status 73454720 MLS 1,449 SqFt.
Welcome to this pristine home in a prime neighborhood w/ the harbor and its stunning views at the end of the street. Close to transportation and a quaint center of town.The freshly painted interior has hardwood fls, living room w/ fireplace and sliding doors opening to a fenced-in backyard w/ a patio and garden perfect for relaxing and entertaining. A room off of the living room is flexible space for work or leisure.This home has been thoughtfully updated with modern comforts, incl. a state-of-the-art 5-head heat pump system(for efficient cooling and full heating), a tankless water heater, new refrigerator and dishwasher, recessed lighting, new garage door. The exterior painted in 2024 and the basement is fully dried-in, and has excellent storage, and finishing potential.This home is truly turnkey! Avoid the Spring market rush and secure this rare find before the competition heats up. Enjoy the seaside charm of Winthrop w/ its 3 yacht clubs, marinas, golf course, and a ferry to Boston

92 Plummer Ave, Winthrop

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