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$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

$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

$840,000
3 Beds 3 Baths ACTIVE Status 73526371 MLS 1,837 SqFt.
This gut-renovated home delivers three levels of flexible living that is hard to replicate. The sun-filled entryway with built-in bench seating & ceiling fan sets a relaxed tone from the moment you walk in. The open main level flows seamlessly from the living room with hardwood floors, beamed ceilings, and built-in electric fireplace through the dining area with its own wine cooler and into a renovated kitchen with white beadboard cabinetry, quartz countertops, subway tile backsplash, and stainless appliances. The entire 2nd floor is dedicated to a private primary retreat, complete with two closets and a private en suite with glass shower. The sun-filled sitting room connects the suite to the 2nd-floor deck where ocean views make for the perfect spot for morning coffee or evening entertaining. A wood spiral staircase leads to the third-floor bedrooms tucked under vaulted ceilings. Corner lot with 2 driveways & the opportunity to expand the yard practically on the water in Pt. Shirley!

27 Billows St, Winthrop

$839,000
3 Beds 2 Baths UNDER AGREEMENT Status 73525692 MLS 1,736 SqFt.
Set on coveted Winthrop Shore Drive, this meticulously maintained penthouse presents an opportunity for elevated, uncomplicated beachside living with breathtaking ocean views from nearly every window. The expansive one-level layout with 1,736 SF of polished living space offers flow and function, comprising three spacious bedrooms, two full baths, 360 degree exposure, three distinct living areas and a bonus office. Highlights include the wall of Atlantic-facing windows enclosing the open living-dining areas, a turret-like primary suite with oversized bath and the view from the roof, where the deck of your dreams could overlook both the ocean and Boston's skyline. Even while immersed in natural beauty, residents enjoy every comfort & convenience: central AC, recessed lighting, high ceilings, premium appliances, stylish finishes, smart home features, in-unit laundry and easy access parking. Built in 2015, this beloved 3-unit building in A+ location also has extra storage and roof rights.

70 Moore St Unit PH, Winthrop

$399,900
2 Beds 1 Baths ACTIVE Status 73524736 MLS 664 SqFt.
Experience the best of seaside living in Winthrop, just steps from the beach. This beautifully updated two-bedroom corner condo offers stunning ocean views along with breathtaking sunrises and sunsets from nearly every window. Conveniently located close to public transportation and Boston Logan International Airport, this home offers the perfect balance of coastal charm and city accessibility.The bright and sunny third-floor unit features an updated kitchen with granite countertops, stainless steel appliances, and the convenience of an in-unit washer and dryer. HOA fees include heat and hot water. Also a nice size storage unit in the basement for extra storage. The professionally maintained building has undergone extensive recent improvements.

53 Trident Unit 303, Winthrop

$779,986
6 Beds 2 Baths ACTIVE Status 73523937 MLS 2,560 SqFt.
PRICE REDUCTION! 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

$760,000
3 Beds 3 Baths SOLD Status 73523725 MLS 1,996 SqFt.
Stunning 2022 rebuild—taken down to the original foundation and rebuilt with a fresh, nearly-new feel throughout! This townhome-style condo feels like a single-family, nearly 2,000 sq ft, featuring 3 beds, 3 full baths, private outdoor space, and 2-car parking. NO monthly condo or HOA fees; annual master insurance just $1,670. A standout alternative to East/South Boston with quick Downtown Boston access via MBTA and highways. Sun-filled main floor with open living/dining, stylish kitchen boasting high-end appliances, two-tone cabinetry, large island, plus deck access. Upstairs includes two bedrooms with a primary suite showcasing dramatic cathedral ceilings. Finished lower level ideal for media room, gym, or guest space. Near marinas, waterfront parks, transit, and dog-friendly Belle Isle Marsh. Special financing from SIRVA Mortgage.

55 Banks St Unit 2, Winthrop

$1,199,999
4 Beds 4 Baths ACTIVE Status 73521657 MLS 1,904 SqFt.
Nestled on a peaceful street between the shoreline of Donovan's Beach and the green space of Ingleside Park, this beautifully renovated single-family home offers exceptional flexibility and comfort across multiple levels. Thoughtfully updated from the rooftop to the lower level, the home is truly move-in ready with modern finishes and inviting spaces throughout. Sun-filled interiors create the perfect balance of open gathering areas and quiet workspaces, while large windows bring in abundant natural light. Designed for both everyday living and entertaining, the layout provides versatility for a variety of lifestyles. Step outside to an incredible outdoor setting ideal for relaxing, dining, and enjoying every season. With coastal charm, nearby recreation, and turnkey convenience, this home presents a rare opportunity to enjoy the very best of Winthrop living.

70 Edgehill Rd, Winthrop

$960,000
5 Beds 2 Baths SOLD Status 73518328 MLS 2,123 SqFt.
A forever home that doubles as your summer escape. Located in one of Winthrop's most desirable neighborhoods, this beautifully renovated single-family home offers three levels of coastal living. Step through the foyer and you’re greeted by soaring ceilings, a statement fireplace, and a dining space designed for memorable family dinners and entertaining alike. The chef’s kitchen steals the show with quartzite countertops, custom cabinetry, a professional grade Thermador gas range and water views. Completing the main level is a cozy den and heated sunroom. Upstairs offers four spacious bedrooms and a beautifully renovated full bath, while the entire third floor functions as a private guest suite complete with full bathroom and flex space ideal for a home officet, gym, or Peloton setup. Enjoy close proximity to Yirrell Beach, Ingleside Park, Belle Isle Seafood, The Half Cookie, Orient Heights Station, and and countless local cafés and restaurants - all just 6 miles from Boston

57 Loring Rd, Winthrop

$675,000
3 Beds 2 Baths SOLD Status 73518243 MLS 1,690 SqFt.
Spacious 3 bed/2 bath townhouse that lives & feels like a single family w/ oversized garage & expansive backyard located in the heart of Winthrop offering the perfect blend of coastal charm & city convenience. Enter to an open concept floor plan w/ living room & sliding doors that open to the private patio & yard- perfect for indoor/outdoor entertaining. Updated eat-in kitchen boasts abundant cabinetry, S/S appliances, quartz countertops & breakfast bar w/ seating for 3. 2 well-sized bedrooms that easily fit queen beds, generous closet space & a full bath with tub/shower combo complete this floor. The lower level features a spacious family room/office area & a large king-size bedroom w/ walk-in closet. In-unit laundry & a 2nd full bath w/ shower stall complete this floor. This home is complete w/ central air & 2 outdoor parking spaces. Live moments from all Winthrop has to offer-beaches, local shops/cafes/restaurants & easy access to public transit, Logan Airport and downtown Boston.

73 Bartlett Rd Unit 1, Winthrop

$725,000
5 Beds 2 Baths SOLD Status 73517634 MLS 1,935 SqFt.
Located just one block from Winthrop Beach, this spacious single-family home offers an incredible opportunity to own in a highly desirable coastal community with convenient access to the city. Featuring three levels of living space, this home includes 5 bedrooms, 1.5 bathrooms, and a fenced-in yard perfect for outdoor enjoyment. Ideally situated just 15 minutes from Logan International Airport and approximately 20 minutes to downtown Boston. Commuters will appreciate the easy access to public transportation, including the T and bus lines, as well as major highways such as Routes 1, 90, and 93. Situated on a double lot, this property may offer future expansion or development potential with the appropriate approvals and variances. Buyers and buyer’s agents to perform their own due diligence. OFFER DEADLINE MONDAY 5/18 12PM.

30 Hutchinson St, Winthrop

$299,999
1 Beds 1 Baths UNDER AGREEMENT Status 73517506 MLS 351 SqFt.
Welcome to The Cove, a distinguished condominium community in coastal Winthrop, offering a spectacular seaside setting with the Boston skyline as the backdrop for unforgettable sunsets. This renovated second-floor studio features wood flooring throughout, an updated kitchen with dining space, and a private balcony off the living area. The unit includes a modern bathroom with a walk-in shower, laundry in the building, and the rare convenience of two off-street parking spaces.Enjoy a short walk to the seasonal ferry for easy access to downtown Boston, along with additional nearby public transportation options. Two beautiful beaches are just a couple of blocks away in different directions, perfectly capturing the coastal lifestyle. Ideally located minutes from downtown Boston, Logan Airport, and major highways, with easy access to Winthrop’s local shops, restaurants, and waterfront charm. A great opportunity for first-time buyers — why rent when you can own?

600 Shirley St Unit 11, Winthrop

$450,000
2 Beds 1 Baths SOLD Status 73517135 MLS 1,083 SqFt.
Beautifully maintained condo in highly desirable Winthrop offering the perfect blend of coastal charm and city convenience. This sun-filled home features a spacious open layout, generous living areas, large bedrooms with ample closet space, and stylish wall-to-wall bamboo laminate flooring throughout. Enjoy the convenience of in-unit washer and dryer, three-car parking, and a back porch perfect for relaxing and enjoying the ocean breeze. Located just steps from the beach, with easy access to local restaurants, public transportation, and downtown Boston. An outstanding opportunity for both owner-occupants and investors alike. Low condo fee of only $240/month makes this property an even greater value.

48 Crystal Cove Ave. Unit 2, Winthrop

$799,999
4 Beds 2 Baths ACTIVE Status 73517107 MLS 2,000 SqFt.
Direct Ocean Front Living. Feel like you're on vacation every day! This spacious 2 level,7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day.Every day the the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining room, ( Living room-could be master bedroom) the beautiful kitchen has cherry cabinets granite countertops, stainless appliances sliders to the large deck facing the sandy yard and Beach. This is one of a kind and Direct Ocean front living. All the rooms are large with plenty of character. Walk in closets and Laundry room make this for easy living. Bus line to the Blue line and Water shuttle into Boston is just a couple minutes away at the landing next to Winthrop yacht club. Marinas, shops and restaurants add to this great community. Don't miss out on this Opportunity to live Directly on a beach

876 Shirley Street Unit 1, Winthrop

$550,000
1 Beds 1 Baths SOLD Status 73517090 MLS 994 SqFt.
Experience refined waterfront living in this fully renovated, ocean-facing residence. The chef’s kitchen is a true centerpiece, featuring a brand-new center island, quartz countertops, and premium appliances—perfect for effortless entertaining. Modern upgrades shine throughout, including new electrical, recessed lighting, and sleek ceiling fans. Relax in the spa-inspired bathroom with a walk-in shower, or retreat to the spacious bedroom offering magnificent ocean views and ample space for a home office. Step onto your private balcony to savor morning coffee or golden hour sunsets over the water. This turn-key home includes garage parking and access to premier amenities: a pool, fitness center, and tennis(pickleball) courts. Embrace the Winthrop lifestyle with it's local beaches, a golfclub, and yacht clubs. Commuting is a breeze via the seasonal city ferry or nearby transit. From vibrant dining to scenic coastal trails, everything is ready for you to move in and enjoy!

1 Seal Harbor Rd Unit 300, Winthrop

$1,317,500
5 Beds 2 Baths SOLD Status 73514990 MLS 3,754 SqFt.
Located in one of the most desirable neighborhoods in town, this grand home has been the home to 4 generations of the same family since it was built. It has been cherished by the same family for over 100 years. Rich original woodwork and timeless character can be found throughout. Step into the sun-filled enclosed front porch before entering the impressive foyer featuring a stunning quarter-sawn oak staircase. The spacious kitchen offers endless potential for renovation and customization. The second floor features a generous landing, 5 large bedrooms, and a three-quarter bath. The third floor offers three additional spacious rooms plus a bonus area leading to a loft space, providing flexibility for extended living, office, or creative use. Situated on a corner lot with ample backyard space, this property is a rare opportunity to restore and personalize a truly special home.

264 Court Rd, Winthrop

$475,000
1 Beds 1 Baths SOLD Status 73514946 MLS 623 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 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

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