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$2,250,000
16 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73554183 MLS ⋅ 5,553 SqFt.
566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been well maintained and features all new common area lighting and carpeting, the foundation (interior and exterior) has been repointed. The Property has new blown-in insulation, and the rear deck system has been updated with refinished decks and new railings. The Property also has a new 11-camera security system and credit card operated washers and dryers. Two of the units have been fully renovated and two units have renovated bathrooms. The Property is separately metered for a mix of gas & electric powered heat & hot water, as well as electrictity. The Landlord provides town water & sewer.

566 Shirley St, Winthrop
$1,260,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73550792 MLS ⋅ 3,150 SqFt.
Modern living made easy at 21 Hutchinson Street, two family with 3150 SF of living space. Come experience modern finishes in this fully renovated home. Unit 1 offers an easy access layout with first floor main bedroom on-suite bathroom and walking closet. The main area offers a versatile open floor plan with half bathroom and laundry. The second bedroom located in the lower level of this unit to offer full privacy with a sitting area, and generously sized spa bathroom. Unit 2 offers two generously sized bedrooms each with walking closets and on suite bathrooms. The main area features one half bathroom and laundry. New HVAC system offering gas heat and central cooling. Tankless water heaters two thermostat zones for each unit and gas stoves. Outside features 2 car garage, 2 electric car charging stations, new fence, and concrete patio area. All siding, roof, windows, electrical and plumbing are new. Move in Relax and Enjoy your new home in the quaint town of Winthrop!

21 Hutchinson Street, Winthrop
$780,000
6 Beds ⋅ 2 Baths ⋅ PRICE CHANGED Status ⋅ 73545756 MLS ⋅ 2,000 SqFt.
Ingleside Park 2-unit with oversized 10,000sqft lot and parking for 2 cars that offers plenty of potential in a central Winthrop location. Property is in need of interior updating and the back yard is ready to become either expanded parking, a beautiful yard space, or more. First floor unit has two bedrooms, one full bath, and a large rear deck. Second floor unit has two levels with four total bedrooms and one full bath. Building has separate electric and gas meters. Located next to Ingleside Park and the new Winthrop Center, and one mile to the MBTA Blue Line direct to Logan airport and Boston.

120 Hermon St, Winthrop
$875,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73542949 MLS ⋅ 2,016 SqFt.
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
$1,499,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73541145 MLS ⋅ 2,889 SqFt.
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
$715,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73539167 MLS ⋅ 1,963 SqFt.
FRESH NEW PRICE! Best value in the neighborhood! Charming 1930's two family, originally a seaside cottage, just steps to the beach. Family owned for over 70 years, it's now time for someone else to enjoy this coastal home. 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
$939,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73537801 MLS ⋅ 1,924 SqFt.
NEW PRICE! Fresh Updates! Now Vacant! Exceptional 2-family in desirable Winthrop. Same owner for 20 years! Turnkey opportunity for Investors or Owner-Occupants seeking strong rental income. Great for Multi-Gen living! Both units offer hardwood floors, closets, and spacious Kitchens w/ Pantrys. Windows galore! Gorgeous natural light! Beautifully proportioned rooms, easy floorplans, great storage. Welcoming farmer’s porch, fenced yard, and more! 3 OFF-ST PARKING SPACES. Unit 1 offers 2 BR’s, LR, DR, and huge Kitchen. Upstairs, Unit 2 features 1BR plus a windowed dressing room/WFH office, LR, DR, roomy Kitchen, along with exclusive access to a finished heated attic with 2 sunny bonus rooms ideal for WFH/guests/storage/gym. Unfinished basement with flex space for storage/hobbies. Steps to WINTHROP H.S. Close to parks, beaches, restaurants. Minutes to East Boston, Orient Heights MBTA/Buses, Logan, DT Boston. GPS "Oceanview"

105 Ocean View St., Winthrop
$850,000
5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73537768 MLS ⋅ 3,035 SqFt.
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
$1,100,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73534385 MLS ⋅ 2,949 SqFt.
A rare opportunity to own a 4-unit multi-family investment property in one of Winthrop's most sought-after coastal locations, just minutes from downtown Boston and Logan Airport. This asset offers an ideal mix for investors and owner-occupants alike. The property features one three-bedroom apartment, one two-bedroom apartment, and two studio units. The three-bedroom and one studio apartments are currently leased, and the remaining studio and two-bedroom apartments can be delivered vacant. Three off-street parking spaces come with the property. Set on a 4,075± sq ft lot in a supply-constrained market with strong, year-round rental demand, the property delivers a compelling blend of in-place income and future growth potential through both rent increases and value-addition. Steps to the beach, Winthrop Golf Club, and the heart of Shirley Street, come see everything that this property has to offer.

32 Irwin St, Winthrop
$2,250,000
16 Beds ⋅ 14 Baths ⋅ ACTIVE Status ⋅ 73531829 MLS ⋅ 10,000 SqFt.
DEVELOPMENT OPPORTUNITY WITH EXISTING MIXED USE PROPERTY GENERATING $71K NET ANNUAL INCOME.++A rare coastal investment and development opportunity in the heart of Winthrop, Massachusetts. The mixed use property currently consists of a cash-flowing four-unit mixed-use building with stable in-place NOI of 71,300, combined with a Board of Appeals–approved plan to construct a new 12-unit building with podium parking beneath — all on one site steps from the harbor and in the middle of a quaint yet thriving downtown Winthrop. 5-10 min commute to Boston Logan Airport, quick access to the MBTA Blue Line and ferry access to downtown Boston. All dimensions, square footage, parking spaces and building plans are estimated and should be considered for marketing purposes only. Buyers to do all due diligence as this is a development opportunity.

63-69 Putnam St, Winthrop
$4,724,900
10 Beds ⋅ 15 Baths ⋅ ACTIVE Status ⋅ 73531014 MLS ⋅ 9,156 SqFt.
Rooted in history & reimagined with intention, The Pearl is a one-of-a-kind five-unit multifamily property by the coast in Winthrop. Formerly a church, the building has been thoughtfully transformed into five distinct loft-style residences, each with its own layout, character & design identity. Original architectural details including exposed beams, hardwood floors, oversized windows & dramatic ceiling heights are balanced with modern finishes throughout. Each residence features Bosch appliances, electric fireplaces, in-unit laundry, radiant heated primary baths, walk-in closets, hidden powder rooms, concealed storage, private outdoor space with automated retractable awnings, additional storage & two off-street parking spaces. Located near Winthrop’s beaches, harbor walks, cafés, restaurants & commuter access into Boston, The Pearl offers a special opportunity to own a boutique coastal multifamily with historic character, strong design & flexible long-term potential.

1001 Shirley St, Winthrop
$999,888
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73529063 MLS ⋅ 2,635 SqFt.
NEWLY PRICED! PRICED TO SELL! Rare waterfront two-family in Winthrop's sought-after Cottage Park neighborhood, offering stunning views of the Bay, Harbor, marsh, and ocean, a lifestyle feature you simply can't replicate at this price point. Built in 1920, this classic 2,635 sq ft two-story home sits on a 5,227 sq ft lot just steps from the beach. A perfect opportunity for first-time buyers or savvy investors. Unit 1 rents for $3,100/mo and Unit 2 for $4,000/mo, generating $85,200 in gross annual income with a net of $76,900. Five bedrooms, two full baths, and a versatile layout ideal for extended families. The property features an enclosed porch, deck, fenced yard, professional landscaping, and individually metered electric. Minutes from downtown Boston via Rt. 1A. Don't miss this opportunity; schedule your private showing today!

66 Sunnyside Ave, Winthrop
$799,986
6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73523937 MLS ⋅ 2,560 SqFt.
Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience and value for both owners and tenants. The property also offers plenty off-street parking, a paved driveway, and a private outdoor area. Conveniently located near restaurants, shopping, public transportation, beaches, Logan Airport, and major highways, making commuting into Boston quick and easy. Strong rental demand in the area creates excellent income potential and long-term upside. Whether you are looking to expand your investment portfolio, generate steady rental income or occupy one unit while collecting rent from the other, this property checks all the boxes!

50 Main St, Winthrop
$1,199,900
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73515977 MLS ⋅ 2,799 SqFt.
$2,500 bonus to buyer or buyer broker* Exceptional opportunity to live where you work. Corner lot with off-street parking, this unique property offers endless possibilities for investors, developers, or owner-occupants.The ground level features professional office space complete with a reception area, conference room, workspace, and 1/2 bath. Also included is a vacant 2-level, 2-bedroom, 1.5-bath unit that has been beautifully and completely renovated, featuring ocean views from the bedrm.In addition, the property offers a spacious 5-room, 3-bedroom, 1-bath unit and a large basement for added flexibility and storage.Conveniently located in a high-traffic area near schools, restaurants, and shops, just minutes from the public beach and major highway access. Potential to expand to 8-12 micro units. Buyers are encouraged to consult the Winthrop Bldg Dept. regarding the pot. expansion.Current tenants at will Ofc $2,500 U2 (3)bed $2,500 unit 3vacant *PLANS ATTACHED FOR POSS. 1BED UNITS W/O

193-195 Winthrop St, Winthrop
$1,299,000
7 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73510154 MLS ⋅ 3,989 SqFt.
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
$849,900
5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73508827 MLS ⋅ 2,843 SqFt.
Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms & 2 bed.Kitchen has Induction Stove Top Granite Island & Counter Tops.Stainless Steel Induction Wall Microwave & Wall Oven.Top of the line Stainless Steel Refrigerator & Dishwasher.Granite tile floor. Plenty of Cabinet Space. Beautiful Tiger Hardwood Floors & Natural Woodwork Throughout. Crown Moldings & Chair Rails.Wood Fireplace in Living Room. There's a closet from the kitchen that was used as a staircase to the Basement that's finished with a huge full bath washer & dryer, Family Room & bedroom. That can be added in on the room count to 7 rooms 3 beds 2 full baths. 2nd floor 4 Large Rooms & 2 Bed.Plenty of Cabinet Space.Beautifull Hardwood Floors and All Natural Woodwork Throughout. Huge Living room. Dining Room has a spot for wall A/C. 4 Car Parking, Nice Huge Fenced in Yard with a Large Patio & Shed. Plenty of Parking Around The House Because of the corner Lot.5year old roof

7 Willis Ave, Winthrop
$1,650,000
6 Beds ⋅ 6 Baths ⋅ UNDER AGREEMENT Status ⋅ 73489316 MLS ⋅ 4,122 SqFt.
Situated just steps from the sand, 304 Shirley presents a rare opportunity to own a fully occupied 6-unit building in one of Winthrop's most desirable seaside neighborhoods. Each unit is a well-maintained 1-bedroom, offering consistent rental income and strong tenant demand. This beachside property is perfectly positioned near local shops, restaurants, and public transportation, making it a convenient and attractive location for tenants year-round. Unit 2 has the following updates: new flooring, new paint, updated kitchen, new light fixtures.

304 Shirley Street, Winthrop
$989,000
7 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 72706576 MLS ⋅ 3,800 SqFt.
A rare opportunity with a 2 family home on one of the best streets in Winthrop! One block to the ocean. Several locale yacht clubs. A few blocks to the town center with many shops, a few great cafes, several excellent restaurants, Great sized yard with a basketball court. One car garage and 4 car off street tandem parking. Refinished hardwoods throughout the entire home. Tiled bathrooms, kitchen, and second unit. Granite countertops and stainless appliances, Brand new Orient Heights T station off the blue line is a short bus ride away. (1.4 miles) Only a short 15 minute car ride to Boston. Washer / dryer room in both units. Central AC in 3rd floor. HUGE living room with a large wood burning fireplace. Comfortable three season front porch and generous sized open air rear deck.Third floor can be an oversized Master Suite or used as an in-law for extended family! There are not many homes like this in Winthrop.

170 Cottage Park Rd, Winthrop

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