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$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

$650,000
3 Beds 2 Baths ACTIVE 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

$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

$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

$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.
The seller is offering a unique opportunity to lower buyer's payment temporarily for 3 years. The offer is a 3-2-1 temporary rate buy-down that reduces payments years 1-3 by 3% first year, 2% second year, 1% third year.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

$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

$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

$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

$485,000
2 Beds 1 Baths ACTIVE Status 73515219 MLS 913 SqFt.
Welcome home to this pristine and exceptionally well-kept two-bedroom, one-bath condominium in the heart of Winthrop’s vibrant 02152 community. This inviting home offers comfortable living along with private outdoor space—perfect for relaxing, entertaining, or enjoying coastal breezes. Conveniently located with easy access to Orient Heights, major highways, Logan Airport, and downtown Boston. The location of 43 Sagamore makes commuting simple while still enjoying the charm of a seaside town. Winthrop Beach is just moments away, offering the perfect setting for everything coastal living has to offer. A wonderful opportunity to own and become part of this welcoming waterfront community. Ask about available mortgage options.

43 Sagamore Ave Unit 1A, Winthrop

$585,000
2 Beds 2 Baths PRICE CHANGED Status 73511795 MLS 1,141 SqFt.
Very reasonable condo fee. Newer built condominium in a prime Winthrop Center location, Belle Mer is a professionally managed association with 15 of 16 units owner occupied. Kitchen equipped with stainless Bosch appliances, wine cooler, + wonderful island to gather for enjoyment. Harbor views from the main bedroom, incredible closet space, and inviting window seat. Lofty ceiling height thru out + abundant wall space for art and photos. 2 pets are welcomed. 1 assigned parking space plus multiple guest parking. Convenient 2nd floor laundry. Bathrooms boast timeless designer tile. Ideal access into condo via front and back PRIVATE entries. The picturesque neighborhood is surrounded by natural beauty, a wonderful variety of cafes and eateries, yoga studios, farmers market, and ez access to Boston. This modern 2 bedroom, 2 bath condo on 2 levels Condo fee $300 Dog friendly

142 Pleasant Street Unit 12, Winthrop

$895,000
4 Beds 2 Baths CONTINGENT Status 73509670 MLS 1,755 SqFt.
Wake up every single morning to beautiful, unobstructed water views from this home; sitting proudly on a rare, oversized lot. Positioned directly across the street from the water, this property offers the ultimate coastal lifestyle with endless space to expand, entertain, or build your dream outdoor oasis. Inside, you will find a couple of freshly painted bedrooms to offer a clean start, while the rest of the home is a blank canvas ready for your design ideas and style updates to make this home into your dream coastal escape. Whether you're planning thoughtful updates or a full transformation this is a unique chance to secure both location and land in a premier seaside neighborhood. Bring your vision and unlock the full potential of this remarkable coastal property. Now offered at a new improved price, this is a great opportunity for an oversized lot and water views on the market. Washer, dryer, and refrigerator are being left as gifts!

118 Sunnyside Ave., Winthrop

$659,900
3 Beds 1 Baths ACTIVE Status 73509184 MLS 1,250 SqFt.
Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you’ll find newer flooring, fresh interior paint, updated lighting, and a beautifully remodeled kitchen complete with stainless steel appliances. The home also features an updated bathroom, newer windows, and exterior doors throughout. The first floor boasts an open and versatile layout with a modern kitchen, spacious living and dining areas, and a bedroom currently being used a home office—all enhanced by water views. Upstairs, you’ll find two well-appointed bedrooms and a full bathroom. Conveniently located near public transportation, including bus routes with direct access to the MBTA.

51 Undine Ave, Winthrop

$849,900
4 Beds 3 Baths ACTIVE 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. Plenty of Parking Around The House Because of the corner Lot.5 year old roof. PROPERTY DELIVERED VACANT!

7 Willis Ave, Winthrop

$639,000
2 Beds 2 Baths ACTIVE Status 73506354 MLS 1,302 SqFt.
Seal Harbor in Winthrop offers an elevated coastal living experience that is unparalleled. Timeless detail inside & out of this building is complemented by white-glove concierge service. Unit 342 is a luxury residence with ocean & pool views from every window. It is conveniently located a few steps from the new elevators & welcomes you into an open floor plan with striking natural sunlight; hardwood floors & a modern kitchen with island dining. Unit offers 2 spacious bedrooms with marble en-suite baths & walk-in closets. A private oversized balcony is the crown jewel with magnificent views. Conveniences include garage parking, extra storage ideal for seasonal items, in-unit laundry & central A/C. Residents enjoy premium amenities such as game room, club room with full kitchen, hobby room & multiple meeting rooms. Building also showcases a fitness center, sauna, hot tub, indoor pool & roof deck with Boston skyline & ocean views. Seal Harbor is a hidden gem on the Boston City line.

3 Seal Harbor Road Unit 342, Winthrop

$690,000
3 Beds 3 Baths UNDER AGREEMENT Status 73503432 MLS 1,500 SqFt.
***Seller is VERY motivated***Welcome to your fully renovated and updated home on a quiet corner in Winthrop. This home features a brand new kitchen with wide spanning island, open to the living room. Perfect for entertaining. All new electrical, water heater, furnace, plumbing, insulation and hard wired fire alarms. Approximately 250 sqft was added on and 2 bathrooms were also added making this a 3 bedroom 3 bathroom home. Conveniently located primary bedroom on the first floor has ensuite bathroom. All appliances in home are brand new, half bath located off the kitchen makes it easy for guests to use. Smart thermostat that can be controlled from your phone even when you are on the go. It really is a wonderful little corner lot home with ample yard space if you wanted a garden, front of the house gets sun all day. Walking distance to T and beach and other amenities Winthrop has to offer. OPEN HOUSE: 7/10 5:30-6:30PM. 7/11 10:30AM-12PM. OFFERS DUE MONDAY JULY 13th by NOON.

5 Oceanview St, Winthrop

$975,000
4 Beds 2 Baths UNDER AGREEMENT Status 73503359 MLS 2,916 SqFt.
~~PRICE IMPROVEMENT~~ Introducing 24 FAIRVIEW STREET - a charming 4-bedroom, 1.5 bath Victorian in a prime, central location offering inside & outside enjoyment. This beautiful home has been enjoyed & maintained by the same family for many years & offers timeless appeal throughout. First floor has a family room, living room w/ a fireplace, modern kitchen w/ s/s appliances, separate dining area & a butler's pantry leading to a formal dining room. There are two separate staircases leading to the second floor. The sun filled landing has four bedrooms off of it including a spacious main bedroom w/ two closets, a full tiled bathroom & a conveniently located laundry room w/ storage. The third floor offers a full unfinished attic. Utilities are updated. Summer vacation/family fun starts in the fenced in yard which includes an in ground pool, patio, & a garden area. Close to schools, shopping, public transportation & just 6 miles to Boston.

24 Fairview Street, Winthrop

$375,000
2 Baths ACTIVE Status 73500196 MLS
Sports Bar for Sale - located in Winthrop. All Licenses are up to date and fully transferable- Liquor license included. Fully equipped kitchen- 8 burner stove, pizza oven, flat grill, ice maker, double door freezers x2, double door fridges, new 3 mini split ACs, new inter counter dishwasher, new beer cooler26 outdoor seating, 75 indoor seating, 9 TVs, 2 bathrooms with handicap access. Ample parking in the lot - about 15 parking spots. Used as a Sports Bar and Function hall. Owner currently has 2 other businesses and looking to sell this one to focus on the others. Great investment opportunity with everything included. 9 year lease remaining Rent- $5,200 ex utilities. Feel free to reach out for more info or if you’d like to view the establishment let me know to schedule a showing.

59 Putnam St, Winthrop

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