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$2,250,000
16 Beds ⋅ 6 Baths ⋅ 73554183 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Stephen Girolamo from Listing Office: Horvath & Tremblay.
$1,260,000
4 Beds ⋅ 6 Baths ⋅ 73550792 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Matthew Gallego from Listing Office: Gallego Realty.
$780,000
6 Beds ⋅ 2 Baths ⋅ 73545756 MLS ⋅ PRICE CHANGED Status
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

Listing courtesy of Listing Agent: Steve Binder from Listing Office: Binder Residential.
$1,499,000
5 Beds ⋅ 3 Baths ⋅ 73541145 MLS ⋅ ACTIVE Status
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..
$715,000
4 Beds ⋅ 2 Baths ⋅ 73539167 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Mary Ann Cash from Listing Office: Charlesgate Realty Group, llc.
$939,000
3 Beds ⋅ 2 Baths ⋅ 73537801 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Claudia Perkins from Listing Office: William Raveis R.E. & Home Services.
$1,100,000
5 Beds ⋅ 4 Baths ⋅ 73534385 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Michael Giannone from Listing Office: The Aland Realty Group LLC.
$2,250,000
16 Beds ⋅ 14 Baths ⋅ 73531829 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: The Bill Butler Group from Listing Office: Leading Edge Real Estate.
$4,724,900
10 Beds ⋅ 15 Baths ⋅ 73531014 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: The Legacy Group from Listing Office: Serhant.
$999,888
5 Beds ⋅ 2 Baths ⋅ 73529063 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Mirna Monterrosa Orellana from Listing Office: COM-PRO Real Estate Services, Inc.
$799,986
6 Beds ⋅ 2 Baths ⋅ 73523937 MLS ⋅ ACTIVE Status
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

Listing courtesy of Listing Agent: Matt Tasgin from Listing Office: United Brokers.
$1,199,900
5 Beds ⋅ 4 Baths ⋅ 73515977 MLS ⋅ ACTIVE Status
$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

Listing courtesy of Listing Agent: Lisa Licata-Schepici from Listing Office: L.L.S. Realty LLC.

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