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$875,000
4 Beds 2 Baths SOLD Status 73550227 MLS 1,590 SqFt.
If you've been waiting for the perfect opportunity to live near the ocean - this is it! Located between Winthrop Harbor and Winthrop Beach, with literal steps to the ocean in either direction, this beautiful, completely renovated single family home offers 4 bedrooms, 2 baths, an updated kitchen, hardwood floors, central air and much more! Great back yard, off-street parking and a beautiful wrap-around front porch with water views that New Englanders dream of. Incredible location - just steps to Winthrop Beach and Winthrop Landing with water ferry access to Downtown Boston. Close to restaurants, parks, shops, multiple yacht clubs, public transportation and much more. Minutes to Boston, Logan Airport and points north. Don't miss this amazing opportunity to find your seaside home this summer.

69 Crystal Cove Avenue, Winthrop

$1,475,000
4 Beds 3 Baths UNDER AGREEMENT Status 73549582 MLS 3,056 SqFt.
Custom built in 2021, 38 Nahant Avenue was put together with real attention to detail and the finishes back it up. This home runs on Savant for full smart home control, plus Ring cameras for security. The kitchen is built around a full Thermador appliance package, including three Thermador columns: a full fridge, a full freezer, and a wine fridge. The exterior is Hardie plank with a 7 inch exposure, oversized black Pella windows, a paver driveway and a rear covered deck for year round use. Inside you get 9 foot ceilings on the main level and 10 foot ceilings on the second floor, with 17 in ceiling speakers wired throughout the first floor alone. The primary suite has its own bath with a walk in shower, freestanding tub, and dual vanity. A first floor master suite and an upstairs office with ocean views wrap the the floor plan on the main living levels. Downstairs there is a fully framed out and roughed basement ready for your finishing touches.

38 Nahant Ave, Winthrop

$295,000
1 Beds 1 Baths SOLD Status 73549060 MLS 800 SqFt.
Super affordable top-floor 1-bedroom condo located less than a block from Winthrop Beach! This surprisingly spacious unit features fresh paint, hardwood floors, high ceilings, partial water views, private parking lot and an HOA fee that includes heat and hot water. An excellent opportunity for first-time buyers or anyone looking to enjoy coastal living at an exceptional value for less than most rents in the area. Winthrop offers the perfect blend of coastal charm and city convenience. With beautiful beaches, scenic waterfront walking trails, award winning local restaurants, marinas, and a welcoming small-town atmosphere, it's an ideal place to call home. Located just minutes from downtown Boston and Logan Airport by car, train or ferry, Winthrop provides a relaxed seaside lifestyle without sacrificing easy access to everything the city has to offer.

267 Washington Ave Unit 6, Winthrop

$715,000
4 Beds 2 Baths ACTIVE Status 73548082 MLS 1,586 SqFt.
Cape-style home in Point Shirley, steps from the beach and within Winthrop's most walkable stretch of coastline. Built in 1900 and updated with a remodeled kitchen featuring granite counters and recessed lighting, plus a remodeled full bath with a tiled tub and shower. Original hardwood floors run through the main level and all four bedrooms, paired with bay windows that bring in natural light and water views. The main level includes a living room with a fireplace, a formal dining room, and a sunroom that opens to a screened porch. Central air and forced air heat keep the home comfortable year-round. A full basement with sump pump offers storage and utility space, and a paved driveway provides two off-street parking spaces. Ocean views and public beach access nearby. Enjoy the best of coastal living, where the beach is just steps away & commuting to Boston is easy with quick access to the ferry, T stations, Rt. 1A, Logan Airport.

52 Pebble Ave, Winthrop

$869,900
3 Beds 3 Baths CONTINGENT Status 73546996 MLS 2,125 SqFt.
PRIDE OF OWNERSHIP CAN BE YOURS.......METICULOUSLY CARED FOR AND READY FOR THE NEW OWNERS! Located in one of Winthrop's most desirable areas, this Center Entrance Colonial has Harwood oak floors and a bath on every level. A huge fireplaced living room, eat in kitchen with a slider and deck overlooking the enormous (pool size) yard with a garden area and lots of off street parking. The second level has 3 bedrooms and a full bath and laundry. The Main bedroom is King-sized! The Bonus Room in the basement is multi purposed and easily works for extended family ( IN-LAW POTENTIAL) with another full bath, exrta high ceilings, open floor plan and a direct walk out to the yard. Another separate basement area is a handy workshop/storage area. THIS COULD BE THE ONE! In Winthrop by the Sea boasting 2 beaches, new schools, 3 Yacht Clubs, a nine hole golf course and lots of Great Restaurants!

37 Loring Rd., Winthrop

$760,000
6 Beds 2 Baths ACTIVE Status 73545756 MLS 2,000 SqFt.
Capitalize on the tremendous potential of this centrally located multi with a rare 10,000sqft lot located one block from Ingleside Park. The untouched backyard is ready for your ideas - transform it into additional garage parking, an outdoor oasis, or more. Complete with off-street parking for 2-3 cars and additional easy parking on this quiet side street. The first floor unit offers a large deck, two bedrooms, one full bath. The second floor bi-level unit has two beds downstairs with 2 beds upstairs, one full bath, and an extra rear sunroom. The building is equipped with separate electric and gas meters for each unit. Located just a few blocks away from Winthrop Center, Ingleside Park, and only one mile to the MBTA Blue Line direct to Logan airport and Boston.

120 Hermon St, Winthrop

$900,000
4 Beds 3 Baths SOLD 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

$994,000
5 Beds 3 Baths SOLD Status 73541368 MLS 2,564 SqFt.
Experience coastal living at its finest at 156 Locust Street. Just steps from the beach, this beautifully renovated 5-bedroom, 3-bathroom home offers over 2,500 square feet of stylish living space with ocean views and exceptional indoor-outdoor living. Renovated in 2022, the home blends modern luxury with timeless coastal charm. The stunning primary suite provides a private retreat, while a versatile first-floor fifth bedroom offers flexibility as a home office, bonus room, guest space, or playroom. Enjoy central air, sun-filled living spaces, and seamless access to the private fenced backyard and expansive deck, perfect for entertaining or relaxing after a day at the beach. Recent updates include heating systems (2024 & 2025), a hot water heater (2025), and upgraded 200-amp electrical service. Wake up to ocean views from the front balcony and enjoy a turnkey coastal lifestyle in one of Winthrop's most desirable seaside locations.

156 Locust St, Winthrop

$1,499,000
5 Beds 3 Baths UNDER AGREEMENT 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

$589,000
2 Beds 2 Baths SOLD Status 73540416 MLS 1,241 SqFt.
Rarely available corner unit at the ultra desirable Seal Harbor Condominiums. Enjoy sweeping views of the Atlantic Ocean and beyond from the comforts of your own living room. This two-bedroom, two-bath unit boasts oversized windows and glass sliders with unobstructed ocean views and great natural light, hardwood floors, updated kitchen and bath, in-unit laundry hook-ups, extra storage space and a deeded garage spot. Enjoy the many amenities that Seal Harbor has to offer including a private, in-ground swimming pool, tennis courts, in-building fitness center, sauna, game room, clubhouse & 24/7 concierge and security services. Great waterfront location that is just steps to Winthrop Beach and close to dining, shopping, boating and public transportation. Minutes to Downtown Boston and Logan Airport. Great opportunity to be moved in this summer and enjoy luxury New England coastal living.

1 Seal Harbor Road Unit 116, Winthrop

$500,000
3 Beds 2 Baths SOLD Status 73539637 MLS 1,351 SqFt.
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

$855,000
5 Beds 3 Baths SOLD 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

$635,000
2 Beds 1 Baths SOLD Status 73537671 MLS 929 SqFt.
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

$635,000
3 Beds 2 Baths PRICE CHANGED Status 73536296 MLS 800 SqFt.
Beautifully maintained and truly move-in ready, this 3-bedroom single-family ranch offers comfortable one-level living with the added bonus of a spacious finished lower level. The first floor features hardwood flooring throughout, with tile flooring in the modern full bath. The inviting living room features a fireplace, while the updated kitchen offers recessed lighting and a functional layout. Three bedrooms feature ceiling fans, and the finished lower level provides two bonus rooms, a full bath, laundry room, and separate storage area for added space and convenience. Abundant closet space throughout provides excellent storage.Pride of ownership is evident throughout this well-cared-for home, offering a clean, inviting interior and a move-in ready opportunity. Outside, enjoy a large backyard and spacious deck, perfect for entertaining, outdoor dining, or relaxing. Potential future ADU possibilities may exist, subject to local zoning and approvals. Ideally located near beaches, waterfront dining, parks, fitness facilities, and just minutes from Boston, this home offers comfortable living in a desirable Winthrop location.

496 Winthrop St, Winthrop

$485,000
1 Beds 2 Baths ACTIVE Status 73535636 MLS 591 SqFt.
Stunning water views from every angle make this exceptional condo truly one of a kind. Enjoy breathtaking sunsets over the Boston skyline and harbor from the comfort of your own home. Nestled in the charming seaside community of Winthrop, you'll experience the perfect balance of coastal living and city convenience. The ferry is just one block away, offering a scenic and stress free commute to Boston. Unit features tasteful upgrades, including a custom kitchen marble backsplash, quartz countertop and boasts not one, but two private decks featuring Trex decking. Unit 7 is widely considered the premier residence in the building, featuring the largest private waterfront-facing deck an ideal setting for morning coffee, outdoor dining, or simply taking in the spectacular views. Vinyle double hung windows with thermopane glass. Just in time for summer, this rare offering presents an incredible opportunity to enjoy, waterfront living at its finest.

600 Shirley St Unit 7, Winthrop

$1,325,000
4 Beds 3 Baths SOLD Status 73534719 MLS 2,475 SqFt.
Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive improvements throughout. The open-concept layout is filled with natural light and showcases a beautifully appointed kitchen with custom cabinetry, quartz countertops, stainless steel appliances, a beverage refrigerator, and a large center island. Occupying the entire third level, the private primary suite offers breathtaking water views, a private balcony, a walk-in closet, and a spa-inspired bath. A rare opportunity to own a thoughtfully reimagined coastal home where panoramic water views, abundant natural light, and extensive recent reconstruction come together in one exceptional setting.

89R Upland, Winthrop

$379,000
2 Beds 1 Baths ACTIVE Status 73534695 MLS 677 SqFt.
Welcome to coastal living at its best. HOA FEE INCLUDES HEAT & HOT WATER! This top-floor corner 2-bedroom condo offers ocean views & an ideal vantage point overlooking the water, bringing in incredible natural light throughout. Hardwood floors run throughout the living area, while the kitchen features granite countertops, stainless steel appliances, & ample storage. Recent upgrades include appx. $10K in custom built-ins & thoughtfully designed closet systems to maximize storage & functionality throughout the home. The open living & dining space creates an inviting setting for everyday living or entertaining. Both bedrooms offer generous space, while in-unit laundry provides everyday convenience. Enjoy a professionally managed, well-maintained building with many recent improvements such as a new roof & whole building water heater/boiler. Deeded parking, large locked deeded storage unit, two bus lines incl. a stop at the top of the street w/ direct Blue Line access, ferry access, & walkable walkable restaurants complete this ideal coastal lifestyle

53 Trident Ave Unit 301, Winthrop

$1,100,000
6 Beds 4 Baths ACTIVE Status 73534385 MLS 2,949 SqFt.
A rare opportunity to own a 3-unit multi-family investment property with a fourth apartment 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, one one-bedroom apartment, and one studio unit. The one-bedroom apartment is currently rented and will be conveyed with the property. The two-bedroom and three-bedroom apartments will be delivered vacant at closing. The owner is currently marketing the studio for rent. 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

$1,280,000
9 Beds 3 Baths SOLD Status 73531573 MLS 3,621 SqFt.
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

$747,000
4 Beds 2 Baths SOLD Status 73530454 MLS 2,167 SqFt.
Come discover Winthrop, a charming coastal community just minutes from Boston that feels a world away. This timeless Victorian is filled with natural light, character, and historic charm. Situated on a corner lot just a few homes from the water, you'll enjoy ocean breezes and stunning sunsets from the inviting front porch. Offering generous living space and endless potential, this home is ready for your vision and personal touches. Multiple porches provide opportunities to take in ocean views, while the spacious second floor features generously sized bedrooms. The third floor offers bonus living space and access to a private deck. Located in one of Winthrop's most desirable neighborhoods, this is a rare opportunity to restore a grand Victorian to its former glory. Renovated homes of this size and location have commanded prices exceeding $1.2M. Note some images are AI generated to show homes potential.

4 Woodside Park, Winthrop

$835,000
4 Beds 3 Baths SOLD Status 73530429 MLS 2,447 SqFt.
Spacious 4-bed, 2.5-bath single-family home in Winthrop—where coastal living meets effortless access to Boston. Set near Belle Isle Marsh, enjoy kayaking in calm waters, nearby ocean beaches, yacht clubs, and a scenic seaside golf course—all part of Winthrop’s rare small-town feel. Easy access to the major route in town means smoother, lower-traffic commutes in and out of the city. Inside, sun-filled living areas, a bright kitchen, a separate bonus family room, and a finished lower level with bar and fireplace offer flexible space for entertaining and everyday living. A large fenced yard adds privacy and room to relax, while owned solar panels provide energy efficiency and long-term savings. A standout opportunity combining lifestyle, convenience, and value.

143 Morton St, Winthrop

$495,000
ACTIVE Status 73530360 MLS 1,900 SqFt.
Priced to Sell! This is your opportunity to purchase a versatile 2 unit commercial building located in Metcalf Sq in the Central Business District. The CB district allows for many possibilities such as mixed use & retail/office, etc.. and is a blank canvas for any investor, business owner or developer to transform/redesign this property to suit their needs with loads of potential to increase revenue. Current use is Office space, featuring a 1st floor unit w/great exposure, full windows, open layout suitable for office or possible retail. The 2nd fl unit has character & is bright and sunny w/2 large open areas, vaulted ceilings, (2) private offices, loft area, kitchenette and a private enclosed porch. The front entry is warm & inviting with 2 common restrooms, a nice size yard and a full walkout basement. Winthrop is a wonderful place to open/relocate a business or to invest in. there is meter-less street parking & municipal lots nearby. Current Rents are below market value. U#1-owner occupied, U#2-TAW.

11-13 Pauline St, Winthrop

$495,000
2 Beds 2 Baths UNDER AGREEMENT Status 73529956 MLS 903 SqFt.
Gut renovated and converted in 2020, this upper-level 2-bedroom, 2-bath condo at 34 Underhill Street brings new construction finishes to one of Winthrop's most sought-after pockets. The white shaker kitchen is fitted with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including electric cooking. Wide plank hardwood floors & high ceilings run throughout, and recessed lighting and energy efficient mini-split systems keep the space comfortable year-round. The primary bedroom includes a custom walk-in closet with built-in shelving and drawers and direct access to a full bath. Upstairs positioning means added privacy and elevated sight lines in a building where no detail was overlooked. The Boston ferry, Rt. 1A, and Logan Airport are all minutes away, and the Winthrop coastline is right at your doorstep. Turnkey condition, standout finishes, and a location buyers keep coming back to.

34 Underhill St Unit 4, Winthrop

$495,000
2 Beds 1 Baths ACTIVE Status 73529631 MLS 1,006 SqFt.
Motivated seller! Wake up to panoramic ocean views and experience coastal living at its finest in this stunning top-floor condo directly across from Winthrop Beach. Featuring two private decks, high ceilings, hardwood floors, and sun-filled living spaces, this home offers the perfect blend of comfort, style, and seaside charm. Enjoy ocean views from your bed, an updated eat-in kitchen, modernized bathroom, and abundant natural light throughout. A versatile lower-level bonus room with a large walk-in cedar closet provides the ideal space for a home office, guest room, or fitness area. Additional conveniences include deeded parking and in-unit laundry.Now attractively priced and ready for its next owner, this is an exceptional opportunity to enjoy beachfront living just minutes from downtown Boston. Whether you're relaxing on the deck with your morning coffee or taking a walk along the shore, every day feels like a getaway.

52 Trident Ave Unit 52, Winthrop

$1,180,000
3 Beds 2 Baths SOLD Status 73529299 MLS 2,214 SqFt.
Panoramic breathtaking views offered with this oceanfront Contemporary home via wall of windows & sliders across the front! From the foyer, step down to the living room with fireplace, cathedral ceiling, sliders to deck overlooking the ocean! The dining room also offers large ocean views with slider to deck & is open to the kitchen designed for both functionality & gathering with a convenient peninsula. The main level full bath is spacious with sauna, whirlpool tub, laundry. The 2nd floor main bedroom has walk-in closet, sink and stunning views plus access to loft area on the third level with storage, unfinished room. Two additional bedrooms, full bath & loft area perfect for home office complete the 2nd floor. Beyond the interior, a large deck extends across the front of the home. Unfinished basement with potential for expansion with bonus room & is plumbed for a bath. Paved drive for off street parking, access to beach from lower level. Enjoy the seasons from your ocean front home!

32 Faun Bar Avenue, Winthrop

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