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.
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.
Exceptional 2-family in desirable Winthrop. Same owner for 20 years! Fresh updates + meticulous maintenance equal a 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 STREET 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 and roomy Kitchen, along with exclusive access to a finished heated attic with 2 sunny bonus rooms ideal for WFH/guests/storage/gym. Unfinished basement offers more flex space for storage/hobbies. LONG TERM TENANT HISTORY. Steps to WINTHROP H.S. Close to parks, beaches, restaurants. Minutes from East Boston, Orient Heights MBTA/Buses, Logan, DT Boston. Rare opportunity! Don't miss!
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 value-add 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, two-bedroom, and one studio apartments are currently leased, and the remaining studio will 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.
DEVELOPMENT OPPORTUNITY with existing income property++The Breakwater++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.
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
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.
Discover a unique opportunity at 66 Sunnyside Ave in Winthrop, MA, a 1920 multi-family property offering 2635 square feet of living space. This two-story residence, set on a generous 5227 square foot lot, presents an exceptional blend of classic charm and potential for contemporary living. The property features a total of five bedrooms, providing ample private spaces for residents. Two full bathrooms are thoughtfully integrated throughout the home, ensuring convenience and functionality for multiple occupants. This multi-family dwelling offers a versatile layout, ideal for extended family living or as an income-generating asset. Imagine the possibilities for creating distinct living areas within its expansive footprint. To truly appreciate the lifestyle and potential this property offers, schedule your private viewing today.
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.
Exceptional opportunity to live where you work. Situated on a 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/OFC
Winthrop is located in Massachusetts.
