Refine Search
Map
Sort by
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.
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.
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.
140 Shirley Street Unit 320, Winthrop
$635,000
2 Beds ⋅ 1 Baths ⋅ 73537671 MLS
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, 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 secr

140 Shirley Street Unit 320, Winthrop

Listing courtesy of Listing Agent: Kovacs Savage Team from Listing Office: Byrnes Real Estate Group LLC.
33 Dolphin Avenue, Winthrop
$620,000
4 Beds ⋅ 2 Baths ⋅ 73493754 MLS
Price Improvement! A rare opportunity to create your ideal home in a highly desirable Winthrop location. Offering strong bones, generous living space, and beautiful sunset views, this property is the perfect canvas to add personal style and value. Ideally situated just steps from Winthrop Shore Drive, Winthrop Yacht Club, local restaurants, ice cream shops, Winthrop Golf Club, the High School, and July 4th fireworks in every direction. West-northwest roof views are stunning. While 33 Dolphin requires cosmetic updates and is BEING SOLD STRICTLY AS IS, its location in a well-maintained neighborhood offers exceptional potential. The first floor features a wraparound screened porch, foyer, spacious living and dining rooms, kitchen with deck access, pantry, and ¾ bath. The second floor offers three bedrooms with hardwood floors and walk-in closets, plus a full bath. The third floor includes beamed ceilings, loft area, walk-in closet, and roof access for sweeping views.

33 Dolphin Avenue, Winthrop

Listing courtesy of Listing Agent: Lynn Murray from Listing Office: HUUS One Realty.
35 Nevada St Unit #2, Winthrop
$541,000
2 Beds ⋅ 1 Baths ⋅ 73506269 MLS
Beautifully refinished condo! Enjoy year-round comfort with central heating and air conditioning. The renovated kitchen is a standout, featuring newer cabinetry, quartz countertops, and a full suite of stainless steel appliances, including a dishwasher and garbage disposal. A spacious walk-in pantry with in-unit washer and dryer adds both convenience and functionality. Hardwood floors run throughout the expansive interior, complemented by abundant natural light. Offering over 1,300 square feet of living space, this home provides exceptional room to spread out, along with ample storage options. Two good size bedrooms, and a versatile office adjacent to the primary bedroom for those work from home days. A large walk-in closet too! Step outside to a private porch and take in beautiful beach views! More shared outside space out back with firepit area. Don't miss this beauty less only 3 doors down from Winthrop Beach!

35 Nevada St Unit #2, Winthrop

Listing courtesy of Listing Agent: Maryellen Russo from Listing Office: The Aland Realty Group LLC.
49 Sagamore Ave Unit 3A, Winthrop
$480,000
2 Beds ⋅ 1 Baths ⋅ 73489652 MLS ⋅ ['Sagamore Ocean View Condo Association'] BLDG.
Don’t miss the chance to own this well-maintained 2-bedroom, third-floor condo in Winthrop, Massachusetts. Enjoy being just steps from the ocean while staying only minutes from Boston, a perfect mix of seaside living and city convenience. The unit features an open floor plan with hardwood floors throughout and great natural light. The spacious primary bedroom includes its own private balcony, while the main living area opens to a deck, perfect for enjoying the coastal air. A dedicated in-unit laundry area adds everyday convenience, and the layout offers flexibility for a home office or work-from-home space. Whether you're looking for a primary residence or a chance to own in one of the area's most desirable seaside communities, this condo is a great opportunity to enjoy everything Winthrop has to offer.

49 Sagamore Ave Unit 3A, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
140 Shirley Street Unit 230, Winthrop
$475,000
1 Beds ⋅ 1 Baths ⋅ 73514946 MLS
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 one-bedroom 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. Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

140 Shirley Street Unit 230, Winthrop

Listing courtesy of Listing Agent: Kovacs Savage Team from Listing Office: Byrnes Real Estate Group LLC.
34R Underhill St Unit 3, Winthrop
$450,000
2 Beds ⋅ 2 Baths ⋅ 73550972 MLS ⋅ ['34 Underhill Street Condominium'] BLDG.
This like-new 2-bedroom, 2 bath condo at 34 Underhill Street delivers the finish level of new construction at a fraction of the cost. Gut renovated and converted in 2020, every detail was approached with care, from the white shaker kitchen with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including gas cooking, to the wide plank hardwood floors that run throughout the entire unit. The primary bedroom features a custom walk-in closet with built-in shelving and drawers, and direct access to a full bath. The open living area is bright and generously sized with recessed lighting and mini-split systems for year-round comfort. Ground-floor entry with private access adds convenience rarely found in condo living. Set steps from the Winthrop coastline with the Boston ferry, Rt. 1A, and Logan Airport all just minutes away, this is a turnkey home in a location that continues to attract buyers who want coastal living without sacrificing quality.

34R Underhill St Unit 3, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

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.

How much is your home worth?

Get instant property value now!