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153 Locust St., Winthrop
$680,000
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.
516 Pleasant St, Winthrop
$1,475,000
5 Beds ⋅ 3 Baths ⋅ 73541145 MLS
Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. The units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture.Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

516 Pleasant St, Winthrop

Listing courtesy of Listing Agent: Amanda George from Listing Office: Lamacchia Realty, Inc..
126 Brookfield, Winthrop
$900,000
4 Beds ⋅ 3 Baths ⋅ 73542949 MLS
Two-family home in a prime Winthrop location, directly across from Ingleside Park and minutes from Winthrop Center. Each unit offers 2 bedrooms, 1 full bath, a bright living room, eat-in kitchen, and private porch. Set on a 0.14-acre lot, the property features a partially fenced backyard—ideal for entertaining, gardening, grilling, or relaxing. The lower level, accessible via a private rear entrance, offers excellent potential for flexible use such as a recreation area, home office, gym, workshop, or storage. Recent updates include a roof replacement in 2021. Just a short stroll to Winthrop Center shops and restaurants, and to Donovan Beach, with bus service connecting to the Blue Line and approximately a 30-minute door-to-door commute to Boston via public transit. Whether you're an owner-occupant looking to live in one unit and offset your mortgage with rental income, or an investor seeking rental income in a desirable coastal location, this is an opportunity you won't want to miss.

126 Brookfield, Winthrop

Listing courtesy of Listing Agent: Marissa Amin from Listing Office: Amo Realty - Boston City Properties.
18-20 Fairview Steet, Winthrop
$855,000
5 Beds ⋅ 3 Baths ⋅ 73537768 MLS
Rare opportunity to own a legal 2 family with an inlaw apartment in one of Winthrop's most desirable locations! Completely vacant and ready for its next owner, this brick-front property offers tremendous potential for investors, owner-occupants, or multigenerational living. No flood insurance required. The spacious owner's unit lives like a single-family home, featuring 7 rooms, 3 bedrooms, a sunroom, office, dining room, deck, and a dramatic sunken living room with fireplace. Additional 2-room apartment & in-law apt provide excellent income potential. Set on a beautiful, generously sized lot with a heated 2-car garage, this property is ready for your vision and updates. Enjoy all that Winthrop has to offer—beautiful beaches, scenic waterfront walks, outstanding restaurants, local shops, and a welcoming small-town atmosphere—just minutes to the MBTA, Logan Airport, Boston, and major routes north and south.

18-20 Fairview Steet, Winthrop

Listing courtesy of Listing Agent: The Laura Baliestiero Team from Listing Office: Coldwell Banker Realty - Concord.
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.
95 Marshall St, Winthrop
$500,000
3 Beds ⋅ 2 Baths ⋅ 73539637 MLS
Attention builders, developers, investors & rehabbers! Situated on 4,869 sq ft lot in desirable Winthrop neighborhood, this legal two-family home has been loved for generations & now ready for its next chapter. Originally a single-family, this unique property now offers many options for future use. For ambitious owner-occupants, this could be a great home for multi-generational living or having a rental unit help pay the mortgage. Or it could be converted back to single-family offering at least 3 beds & 2 full baths w/potential to add living space. For investors, fix & flip or hold for rental income & appreciation. For builders, it’s a potential teardown/redevelopment opportunity in one of Greater Boston's most sought-after coastal communities. Features include public water, public sewer, off-street parking, detached garage, fenced yard & level lot. Conveniently located near Main St, town center, beaches, parks, schools & public transportation. Easy access to Boston & Logan Airport.

95 Marshall St, Winthrop

Listing courtesy of Listing Agent: Wilson Group from Listing Office: Keller Williams Realty.
117 Revere St, Winthrop
$1,280,000
9 Beds ⋅ 3 Baths ⋅ 73531573 MLS
HIGHLY DESIREABLE TRIPLE DECKER!! 3 Family INCOME PROPERTY Within Walking Distance to The Beach. Each Unit Boasts 3+ Bedrooms, Large Eat-In Modern Kitchens W/ Plenty of Counter & Cabinet Space, Ceramic Tile Floors in 1st & 3rd Units. 1st Floor Unit Renovated 3 Years Ago Has a Modern Kitchen, Granite Counters, Bathroom w/ Ceramic Tile, Quartz Vanity Top, Full Tub Surround, New Paint, Hardwood & Ceramic Tile Floors. The 3rd Floor Was Renovated Several Years Ago w/ Ceramic Tile Floor in Kitchen & Bathroom, as Well as Full Ceramic in The Bathroom and Full Tub Surround. 2nd Needs Cosmetics. Each unit has a Private Rear Deck & Plenty of Off-Street Parking w/ TWO SEPARATE DRIVEWAYS. Conveniently Located On Bus Line and Minutes From the Blue Line Train Make This EZ Access to BOSTON for Tenants Working Both In Boston & at Logan Airport Who Don't Want to Pay Boston Rents, But Still Want to Be Close to Work, Social Life, Arts etc. RENTS ARE BELOW MARKET FOR FAMILY. MARKET RENTS ARE 3200 PER UNIT

117 Revere St, Winthrop

Listing courtesy of Listing Agent: Peter Marino from Listing Office: Peter A. Marino Realty.
44 Cottage Park Rd, Winthrop
$900,000
6 Beds ⋅ 2 Baths ⋅ 73525592 MLS
Discover the potential of multi-family living located in the sought after Cottage Park area, conveniently located close to downtown, near beaches, restaurants, and public transportation. Flexible layout with excellent opportunity to personalize or add value. This spacious two-family home offers strong potential for owner occupants, investors, or extended living arrangements. Live in one unit and rent the other. Unit 1 offer's 2 bedrooms,1-bathroom, large Livingroom, dining room and laundry in the basement. Unit 2 offers a spacious layout, total of 4 bedrooms, 2 bedrooms on the 2nd floor and 2 bedrooms on the 3rd floor,1 bathroom and in unit laundry. Don't miss this great opportunity.

44 Cottage Park Rd, Winthrop

Listing courtesy of Listing Agent: William McLaughlin from Listing Office: Cameron Prestige, LLC.
47 Bellevue Ave, Winthrop
$1,140,000
6 Beds ⋅ 4 Baths ⋅ 73460507 MLS
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

Listing courtesy of Listing Agent: Jessica Pumphret from Listing Office: Blue Sky Realty.
308 Bowdoin, Winthrop
$999,900
7 Beds ⋅ 3 Baths ⋅ 73508785 MLS
This spacious multi-family offers 7 bedrooms and 3 full baths across 3,628 sq ft, with high ceilings on a 6,429 sq ft lot. Rarely available in Winthrop, it delivers exceptional size, flexibility, and strong rental potential. A cabin-style garage plus a driveway for 4 cars adds convenience, while the lot provides inviting outdoor space. Interiors are well maintained and move-in ready.The first-floor unit features 6 rooms and a full bath. The second unit spans two levels, offering 8 rooms and 2 full baths: the second floor includes the main living space, while the third floor adds additional rooms, a full bath, skylights, and wood floors, ideal for extended family or a private guest suite.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking strong income potential.A prime opportunity in one of Winthrop’s most desirable neighborhoods, perfect for investors or owner-occupants seeking income potential.

308 Bowdoin, Winthrop

Listing courtesy of Listing Agent: The Liriano Team from Listing Office: Liriano Realty.
24 Trident Ave, Winthrop
$1,141,500
10 Beds ⋅ 3 Baths ⋅ 73510613 MLS
Located just steps from the Atlantic, 24 Trident Ave delivers the rare combination of ocean lifestyle and investment fundamentals that rarely surfaces at this price point just minutes from Boston. This property delivers immediate income and serious long-term upside. Two leased (TAW) units generate $4,300/mo with the first-floor updated unit delivered vacant — perfect for an owner-occupant who wants tenants covering the mortgage from day one. This well-maintained 3-family sits less than a tenth of a mile to the beach, with ocean views from the upper floors. Each unit is laid out across a single floor with 3 bedrooms, a full bath, and 7 rooms — the kind of space that keeps good tenants in place. Three off-street parking spaces come with the property, and a full unfinished basement adds storage that owners and tenants will both put to use. Downtown Boston, Logan Airport, Route 1A, and public transportation are all minutes away, making this a prime opportunity that won't last.

24 Trident Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
201-203 Cliff Avenue, Winthrop
$1,650,000
8 Beds ⋅ 7 Baths ⋅ 73465296 MLS
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

Listing courtesy of Listing Agent: Constance Doto from Listing Office: Connie Doto Realty Group.
419 Revere St, Winthrop
$1,331,000
8 Beds ⋅ 4 Baths ⋅ 73502452 MLS
Prime coastal investment opportunity in highly sought-after Winthrop! This 4-family property is directly across from the ocean with beach access and sits on a rare double lot, offering additional outdoor living, or expansion potential. Ideal for investors, owner-occupants, or multi-generational living. Unit 1 features 2 bedrooms. Unit 2 offers 2-3 bedrooms plus a home office w in-unit laundry hookups (could be used as a 3rd bdrm). Unit 3 consists of 3 bedrooms w a 3 seasons porch that views Boston skyline. Unit 4 is a 1-bedroom unit with the best views in the house. The property benefits from its prime coastal location with easy access to the beach, public transportation, restaurants and local amenities. Whether you’re looking to expand your investment portfolio or live by the water while generating income, this property delivers unmatched versatility and location.

419 Revere St, Winthrop

Listing courtesy of Listing Agent: Regina McKennon from Listing Office: 117 Realty.
11 Pearl Ave, Winthrop
$1,107,000
11 Beds ⋅ 3 Baths ⋅ 73491764 MLS
Winthrop is one of the last undervalued waterfront towns in Greater Boston, and opportunities like this don't sit long. 11 Pearl Ave is a vacant 3-family just a block from the ocean, generating $10,500/month at market rents with zero displacement headaches. Three floors, 11 bedrooms total, 4,032 sq ft of income-producing space on a town where the average days on market keeps shrinking. 3 separate heat systems, and 200-amp electric. Flood insurance runs about $2,600/year. Live in one, rent two, or hold all three. Priced at $1,050,000 with a cap rate that pencils with room for improvement and valuate add. Don't sleep on Winthrop.

11 Pearl Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
56 Main Street, Winthrop
$850,000
4 Beds ⋅ 2 Baths ⋅ 73460239 MLS
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

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.
1080 Shirley St, Winthrop
$650,000
3 Beds ⋅ 3 Baths ⋅ 73486096 MLS
1080 Shirley St presents a rare two-family property with two separate structures, offering exceptional flexibility for owner-occupants or investors seeking strong rental potential. Ideally located just steps from the ocean in Winthrop, the property enjoys beautiful water views and a true coastal setting. The front unit features a spacious sunroom that fills the home with natural light, along with a bright and inviting living area. Originally built in 1930 and well maintained over the years, the property offers a combined 2,278 square feet of living space across both units, providing comfortable living and income potential. Outdoor space offers the perfect place to relax and enjoy the ocean breeze. Located moments from beaches, the marina, parks, restaurants, and local shops, the home also offers convenient access to public transportation and an easy commute to Boston. A rare chance to own a versatile coastal property in one of Winthrop’s most desirable seaside locations.

1080 Shirley St, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
19 Moore St, Winthrop
$844,000
5 Beds ⋅ 3 Baths ⋅ 73484508 MLS
Rare opportunity just one street from the beach, offering strong rental income potential ideal for investors and owner-occupants alike. This well-maintained two-family offers a flexible layout with a 2-bedroom 1st floor unit and a spacious second unit with 3 bedrooms & 1.5 baths across two levels. The second unit is currently rented for $3,650/month, providing immediate income, while the 1st floor unit is vacant & ready for an owner-occupant or new tenant. Both units feature hardwood floors and fresh interior paint. Unit 1 includes a decorative fireplace in the living room, while Unit 2 offers in-unit laundry & a well-maintained kitchen. Major updates include a 2020 roof, 2024 water heater, and 2024 boilers with separate gas heating systems. Basement space offers additional storage, plus a rear porch and low-maintenance yard. Ideally located one street from the beach with easy access to Boston via ferry, bus, and MBTA, & close to restaurants and marinas. Schedule a showing today

19 Moore St, Winthrop

Listing courtesy of Listing Agent: Kevin Ochoa from Listing Office: United Brokers.

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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