Winthrop MA Historical Real Estate, Homes for Sale

2 Beds ⋅ 1 Baths ⋅ NEW Status ⋅ 73595832 MLS ⋅ 1,166 SqFt.

HOME SWEET HOME! Are you ready to become a homeowner in the coastal Town of Winthrop? This well-priced, move-in ready Cape offers two bedrooms, a separate study, one full bath, dining room and an eat in kitchen. Situated on a 3,313 sq. ft. lot, this property also features off-street parking and a convenient location close to schools, shopping, Ingleside Park and the center of Town. With bus service to the Blue Line right on the corner, this home offers comfort, convenience and excellent value. Whether you're a first time homebuyer, downsizing or looking for a home to make your own, 96 Marshall St. is an opportunity you won't want to miss! SHOWINGS WILL START AT SUNDAY'S OPEN HOUSE 11:30-1 p.m.

96 Marshall Street, Winthrop

$625,000

3 Beds ⋅ 2 Baths ⋅ NEW Status ⋅ 73595787 MLS ⋅ 1,281 SqFt.

This wonderful seaside home is ready to welcome its next owner! Located less than a block from Winthrop Beach, this lovingly updated single-family home blends modern style with warmth, comfort, and functionality. The stylish granite-topped kitchen features stainless steel appliances and an island, creating an inviting space for everyday living. Outdoor enjoyment is just as appealing, with a private yard offering room to relax, enjoy the outdoors, and take advantage of ample storage space. A welcoming porch extends the living area and provides a seamless connection between indoor and outdoor spaces. Ample parking is a bonus, including a second driveway. Enjoy the best of beachside living in a fantastic location and community just steps from the beach. Easy to show—don’t miss this opportunity!

17 Hawthorn Ave, Winthrop

$849,000

6 Beds ⋅ 2 Baths ⋅ NEW Status ⋅ 73595333 MLS ⋅ 1,920 SqFt.

Work and Relax from one Prime location in Winthrop - between 2 great beaches, with proximity to the Orient Heights blue line MBTA subway to the airport and downtown Boston, and quick access to Route 1A to I-90 and I-93. Recently renovated 2-Family with new eat-in kitchens, stainless steel appliances, granite countertops, new bathrooms, new decks. The upper unit has 3 bedrooms, 1 bathroom, direct access deck from sliding patio doors off the kitchen - perfect for the alfresco meal and beverages; the first first floor unit has 2 bedrooms, 1 bathroom, rear deck out the common corridor. Separate electric & gas/heat. Just a mile to each beach, either Donovan beach or Winthrop beach, public amenities, golf course, boat club, and so much more. Great for an owner occupant and have your tenants pay your mortgage, or a pure investment, or both.

50-52 Bowdoin St, Winthrop

$1,995,000

5 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 73594447 MLS ⋅ 3,686 SqFt.

Truly exceptional waterfront Victorian, with glorious views of Crystal Cove and direct private access to Boston Harbor and beyond, is historic yet fresh, sophisticated yet wonderfully livable! Head out on your boat to explore beaches and islands, restaurants and bars, or relax and enjoy spectacular water views from almost every room. The bespoke water-facing chef's kitchen, with a welcoming island, bar sink and beverage fridge, coffee bar, and suite of Bosch appliances, is an inviting place to gather, cook and linger. Adjacent, the family room beckons, sliding doors bring the outdoors in, and connect to a deck just steps to your own beach. Natural light changes with the day and seasons; the moody grays of winter will be perfectly offset by a cozy fire in the open living room. Naturally there's a dining room, inviting guests for memorable celebrations, family gatherings, and holidays! Upstairs five thoughtfully located bedrooms are paired with more water views, a roof deck, and three tiled baths with elevated finishes. Charming original details go hand-in-hand with the 2026 updates, including ducted heating and cooling, highly efficient replacement windows, on-demand hot water, 400-amp electrical, hardwood flooring, new kitchen and baths, and more. Bonuses include a two car garage awaiting your roof deck and a clean, dry lower level media room w/ high ceilings and potential for expansion! Close to restaurants, Winthrop Yacht Club, Winthrop Golf Course, five minutes to the blue line, 10 minute drive to Logan Airport and Boston. Enjoy coastal living with easy city access! Anticipated completion by November 15th.

119 Washington Ave, Winthrop

$519,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73594243 MLS ⋅ 1,256 SqFt.

Top-floor, two-level 3 bed / 2 full bath a short walk from Winthrop Beach, fully refreshed in 2026: refinished hardwood, new paint throughout, renovated main-level bath, refinished kitchen cabinets. The main floor opens from a sunny living room into a white kitchen with recent stainless appliances, stone counters, pressed-tin ceiling and a pantry closet, with a back door to the rear deck. Two bedrooms and a full bath complete this level. Upstairs is a skylit primary suite with its own full bath, built-in shelving and in-unit laundry. New windows, new skylights and a new roof take the big-ticket items off the table in this 1900 building, and the condo fee covers heat and hot water. No one above you, ocean glimpses from the front windows, pets welcome, and a dedicated off-street parking space so you never hunt for beach parking. Walk to the sand, Shirley St shops, restaurants, schools and the athletic fields; the bus to the Blue Line puts you downtown in about 25 minutes, and Logan is minutes away.

173-175 Shirley St Unit 6, Winthrop

$839,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73594196 MLS ⋅ 2,204 SqFt.

Welcome home to this spacious and versatile property featuring four generously sized bedrooms, a bonus room, and three full bathrooms! Designed to accommodate a variety of lifestyles, this home offers plenty of room to spread out, work from home, and entertain. The first floor features a large living room that flows seamlessly into the dining room, with direct access to the backyard. The updated kitchen boasts slate appliances, an island, and a wine refrigerator, while hardwood floors and a full bathroom complete this level. On the second floor, you'll find a flexible bonus room ideal for a home office, nursery, or additional living space, along with two generously sized bedrooms, an additional bedroom toward the rear of the home, and a full bathroom. The third floor offers even more possibilities, with a spacious area perfect for creating a private primary suite. This level already includes a full bathroom and dedicated laundry, making it an excellent opportunity to customize the space to suit your needs. Outside, enjoy a spacious driveway accommodating two to three vehicles and a fenced-in backyard perfect for entertaining, outdoor dining, or simply relaxing. Conveniently located near local bus service, coffee shops, restaurants, schools, and one of Winthrop's largest beaches, this home offers space, flexibility, and a fantastic opportunity to enjoy all that Winthrop has to offer!

23 Sagamore, Winthrop

$979,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73593881 MLS ⋅ 2,666 SqFt.

Welcome to Winthrop Center. This well-maintained home combines quality craftsmanship with convenient access to the town center. Inside, sun-filled rooms and refined finishes create a cohesive, inviting feel. Spacious gathering areas provide room to entertain, and the home is move-in ready. Nearby, enjoy conservation trails, beach access, shopping, dining, and major commuting routes. This home offers a blend of character, quality, and town-center convenience.

316 Bowdoin St, Winthrop

$989,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73592852 MLS ⋅ 2,180 SqFt.

FULLY GUT-RENOVATED IN 2026 | SINGLE-FAMILY WITH ADU | INCREDIBLE INCOME POTENTIAL! A rare opportunity to own a beautifully renovated home with a separate accessory dwelling unit (ADU) in one of Winthrop's most desirable neighborhoods! Completely gut-renovated in 2026, this unique property offers the feel and convenience of new construction with exceptional flexibility for homeowners and investors alike.The main residence features 2 bedrooms, 2 full bathrooms, a basement, and in-unit laundry. The ADU offers 1 bedroom plus a bonus room, 1.5 bathrooms, in-unit laundry, and two private decks. Two off-street parking spaces behind the property provide added convenience. Location is another standout feature! Situated just around the corner from Winthrop High School, Winthrop Middle School, and the golf course, this property offers incredible convenience in an established neighborhood. Imagine living in one unit while renting the other to help offset today's higher mortgage payments. With the schools just steps away, the ADU could be especially appealing to a local teacher or school employee seeking a convenient commute!Whether you're looking for multigenerational living, additional rental income, or the opportunity to rent both units as an investment, the possibilities are exciting. Two distinct living spaces, a complete 2026 renovation, off-street parking, and a prime Winthrop location make this a truly unique opportunity.

44 Bowdoin Street, Winthrop

$749,974

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73592145 MLS ⋅ 2,520 SqFt.

Attention investors, builders, and contractors! A truly rare opportunity awaits at 104-106 Shirley Street, Winthrop. Situated on an impressive double lot spanning over 10,000 square feet, this property offers incredible upside and potential. The existing home features some fire damage, allowing buyers the flexibility to perform selective renovations, execute a partial demo, or complete a full renovation to suit their vision. Double lots of this footprint are nearly impossible to find in Winthrop, making it an ideal project for tradespeople, savvy investors and whoever looking to add substantial value. Located just minutes from beaches, shops, dining, transit, and a short commute into Boston and Logan Airport, the site and scale are exceptional. Property is being sold strictly in AS-IS, WHERE-IS condition with all faults. Seller or broker make no representations or warranties, express or implied. Buyer to perform all due diligence regarding condition, zoning, permits to able to build , and scope of work

104-106 Shirley St, Winthrop

$425,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73591648 MLS ⋅ 861 SqFt.

Move right into this beautifully updated two-bedroom, one-bath condominium at 29 Seafoam Ave, located less than 500 feet from Winthrop Beach. Recent upgrades include a fully renovated bathroom, fresh interior paint, updated kitchen, and newly refinished hardwood floors, offering a turnkey opportunity from day one. The move-in ready home also features dedicated laundry, direct access to an exclusive-use covered front and side porch, access to a shared backyard, and assigned parking for two vehicles, a rare find in this coastal community. Positioned in a recreation-lover's paradise, this property is just half a mile from the Winthrop Golf Club and Boston Tennis, and under a mile from the Winthrop Yacht Club, boat ramp, and the convenient ferry serving Central Wharf, Logan Airport, and the Seaport. With local restaurants, cafes, and ice cream shops just around the corner, this low-maintenance coastal gem is perfect as a primary residence, seaside retreat, or a sharp addition to any real estate portfolio.

29 Seafoam Ave Unit 1, Winthrop

$498,500

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73591582 MLS ⋅ 1,002 SqFt.

This is your chance to live in Winthrop by the sea. This condo is located in a section of Winthrop known as Point Shirley. This condo is surrounded by amenities. The MBTA. bus to Boston or Logan airport stops directly across the street from your front door at the same place the local school bus stops. Winthrop also has a MBTA. water taxi to Boston. It's a fun ride across Boston harbor. The town beach is only a two-minute walk. Just grab your gear leave the car home and have fun. The neighborhood is great for walking and biking either on the beach or on Grandview ave. You will have on site parking plus curbside parking. Winthrop has three yacht clubs two boat marinas and a golf course. It also have public parks with tennis and basketball and a free boat launching ramp.

1020 Shirley St Unit 1020, Winthrop

$519,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73590903 MLS ⋅ 1,374 SqFt.

Welcome to 23 Trident Avenue, Unit 1, in the desirable seaside community of Winthrop! This spacious first-floor condominium offers approximately 1,374 square feet of living space, featuring 7 rooms, 3 bedrooms, 1 full bathroom, and a versatile bonus room ideal for a home office, creative space, or additional flex space. Thoughtful improvements by the current owner include a new refrigerator, garbage disposal, ceiling fans, bathroom was repainted, and updated light fixtures. Additional highlights include TWO off-street parking spaces and convenient basement storage, providing valuable extra room for your belongings. Enjoy all that coastal living has to offer with nearby beaches, local restaurants, shops, and convenient access to Boston. Whether you’re searching for your first home, need additional living space, or are looking to enjoy the charm of Winthrop, this property offers a wonderful opportunity. Don’t miss your chance to make this condo your own. Schedule your showing today!

23 Trident Unit 1, Winthrop

$665,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73589094 MLS ⋅ 1,413 SqFt.

Welcome to 14 Irwin Street, a charming single-family home in one of Winthrop’s inviting residential neighborhoods. Offering approximately 1,413 square feet of living space, this classic two-story home features 3 bedrooms, 1.5 bathrooms, and 7 total rooms, providing a comfortable foundation for your next chapter. Enjoy the best of Winthrop’s coastal lifestyle with the beach just a short walk away at the end of the street. Plus, with a bus stop just steps away, public transportation is conveniently accessible for an easier daily commute. From morning walks by the water to summer afternoons at the beach, this location makes everyday living feel a little more special. Set on an approximately 4,792-square-foot lot, this home offers room to grow and plenty of opportunity to make it your own. Built circa 1900, the property retains the character of an earlier era while inviting buyers to bring their own vision and personal style. Whether you’re looking for a family home or a place to create lasting memories, 14 Irwin Street offers a wonderful opportunity in a desirable seaside setting. A wonderful combination of coastal charm, convenient public transportation, and neighborhood appeal—truly a must-see property!

14 Irwin St, Winthrop

$1,250,000

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73588891 MLS ⋅ 3,420 SqFt.

Fantastic 3-Family Opportunity in Winthrop Center! Well-maintained and with recent updates, this multi-family property offers an excellent opportunity for investors and owner-occupants alike. The property features a 1-bedroom lower-level unit, a spacious 2-bedroom unit with two bonus flex rooms, and a 3-bedroom unit with two additional flex spaces. Recent improvements include replacement windows, updated electrical, interior and exterior painting, bathroom upgrades, new fencing, landscaping enhancements, soffit and gutter repairs, heating system updates, and added off-street parking. Select units enjoy private outdoor space and all units offer laundry. Ideally located just moments from Winthrop Center's shops, restaurants, beaches, and public transportation. A turnkey investment with strong income potential in one of Winthrop's most desirable neighborhoods.

23-25 Fremont St, Winthrop

$599,900

5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73588699 MLS ⋅ 2,200 SqFt.

Two-Family Opportunity Near the Beach! Located in desirable Winthrop, this two-family property offers an exciting opportunity to build equity in a sought-after coastal community—all for under $600,000. This fixer-upper is ready for someone with vision to bring it back to life and unlock its full potential. Whether you’re an investor looking for your next project or a buyer willing to put in the time and effort to create value, this property offers plenty of possibilities. Enjoy the convenience of being close to the beach, local shops, restaurants, and transportation while taking advantage of the income potential and flexibility a two-family home provides. A great opportunity to renovate, customize, and create lasting value in Winthrop!

91 Fremont St, Winthrop

$799,900

5 Beds ⋅ 3 Baths ⋅ CONTINGENT Status ⋅ 73587974 MLS ⋅ 2,437 SqFt.

Charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile room currently used as a home office. Upstairs, you'll find three spacious bedrooms, a cozy sitting area, and a full bath. A porch roof patio over looking the ocean is a favorite spot to appreciate the views while you sit back and reflect on your day. Perfect ADU potential or in-law space in the lovingly finished and conveniently laid out walk out lower level with an oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, a laundry area. Complete with a bedroom and a full sized cedar closet, this is the home for you! Walk out your lower level door to a covered area for a table or another sitting area. The outdoor shed has doors that open up to the pergola with a bar and tv so you can watch the games during your cookouts. Enjoy the convenience of three off-street parking spaces and easy access to Boston, Logan Airport, scenic waterfront trails, shopping, dining, and more. Don't miss it!

43 Dolphin Ave, Winthrop

$1,095,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73587151 MLS ⋅ 2,910 SqFt.

Stunning home in the heart of Winthrop. This exceptional American Foursquare combines timeless architectural character with extensive renovations and modern finishes throughout. Spacious and sun-filled, the home offers beautifully remodeled interiors, off-street parking, and exceptional indoor/outdoor living while preserving its classic craftsmanship. A newly remodeled mudroom with custom storage, new windows, and recessed lighting opens to a gracious living room with hardwood floors and a gas fireplace with a newly constructed surround. The spacious dining room features traditional wainscoting and an elegant setting for entertaining.The fully remodeled kitchen is the centerpiece of the home, featuring a large center island, custom cabinetry, designer tilework, new flooring, and generous workspace. An expansive Trex deck overlooks the fully fenced, professionally landscaped 6,000 sq. ft. lot, creating an exceptional setting for outdoor dining and entertaining. A full bath completes the main level.The second floor offers three generously sized bedrooms, and fourth bedroom currently being used as a home office. A fully remodeled bath with new finishes and fixtures caps off the second floor. The finished third floor provides flexible bonus space ideal for an office, guest retreat, media room, playroom, or library.The newly finished lower level offers a separate in-law suite with a brand-new kitchenette, second gas fireplace featuring hand-built stonework, half bath, dedicated gym, and laundry area—ideal for extended family, guests, or additional work-from-home space. Short distance to schools, Town Center restaurants and cafés, shops, the library, parks, and beaches, with convenient access to Boston, the Seaport, Financial District, and Logan Airport.

61 Read Street, Winthrop

$540,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73586927 MLS ⋅ 1,295 SqFt.

Welcome to this immaculate top-floor corner condo in Chase Condominiums, where privacy, natural light, and effortless one-level living come together beautifully. Abundant corner windows fill the spacious home with light while offering a peaceful sense of privacy. The generously sized primary suite features an updated en-suite bath with a tiled shower, Jacuzzi tub, and walk-in closet. The second bedroom offers its own private bathroom and tall, bright windows. An open-concept layout seamlessly connects the living and dining areas, creating endless possibilities for entertaining, relaxing, and everyday living.The updated kitchen features granite countertops, tall cabinetry, stainless steel appliances, and a brand-new washer and dryer. Step outside to your large private deck—perfect for morning coffee, outdoor dining, or simply enjoying your own private outdoor retreat. Extra Storage unit is deeded with the unit(#5), along with 1 deeded parking spot (#14)The well-maintained complex offers an inviting shared roof deck with ocean views, tables, comfortable seating, and seasonal décor. It’s an exceptional spot to take in the Fourth of July fireworks over Boston or from Winthrop High School. Enjoy beautifully landscaped grounds and a convenient location just moments from marsh trails, playgrounds, dog parks, and access to Winthrop Beach. With its spacious floor plan, abundant natural light, private outdoor spaces, and fantastic coastal lifestyle, this condo offers the perfect blend of comfort, convenience, and privacy.

15 Ocean Unit 206, Winthrop

$569,000

2 Beds ⋅ 1 Baths ⋅ CONTINGENT Status ⋅ 73585619 MLS ⋅ 1,692 SqFt.

Opportunity awaits at 16 Loring Road in Winthrop! This 6-room home offers 2 bedrooms and plenty of potential for buyers looking to renovate, customize, or invest. The property features oil heat, an unfinished basement with convenient walkout access, and a detached two-car garage offering additional parking and storage. Situated on an approximately 5,500 sq. ft. lot. Bring your ideas and vision to unlock the possibilities this property has to offer. Property is being sold strictly AS-IS. Seller makes no representations or warranties regarding the property or its condition. Buyer and buyer’s agent are responsible for conducting their own due diligence and verifying all information to their satisfaction.

16 Loring Rd., Winthrop

$1,275,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73585487 MLS ⋅ 2,599 SqFt.

Welcome to your ultimate beachfront oasis in Winthrop, where every day feels like a permanent getaway with direct access from your back door straight into the sand. This stunning home features an inviting, fireplaced living room, a kitchen boasting sleek marble countertops and tile flooring, a convenient main-floor full bath and an outdoor shower for rinsing off after the beach, and two flexible bedrooms ideal for guests, children, or a home office. Take in breathtaking ocean sunrises over morning coffee from the year-round heated sunroom, and retreat upstairs to a spacious primary suite complete with its own private bath. The finished lower level functions as a fully separate suite—an incredible asset as one of only 10 legal Airbnbs in all of Winthrop, complete with its own family room, bonus space, full bathroom, and laundry. Positioned in an unbeatable location with two off-street parking spots and an EV charger, this property sits less than 1 mile from the Winthrop Landing MBTA ferry for easy transit to Logan, Central Wharf, and the Seaport, perfectly balancing everyday coastal luxury with elite short-term rental potential.

129 Strandway, Winthrop

$549,995

2 Beds ⋅ 1 Baths ⋅ PRICE CHANGED Status ⋅ 73585000 MLS ⋅ 1,614 SqFt.

Ocean views, salty breezes & beachside living just minutes from Boston! This bright 2-bedroom, two-level condo offers direct ocean views & a deeded patio exclusive to the unit. Across the street, enjoy the beach & a 2-mile walking trail, perfect for morning strolls. Abundant windows fill the open-concept living space with natural light, while a 3 sided gas fireplace adds warmth & charm to the center of the entertaining space. The updated and spacious eat-in kitchen features newer appliances, a coffee bar, and bar seating. Wake up to ocean views in the primary bedroom, complete with a walk-in closet! The updated bath offers a spacious shower & jetted tub with a unique ceiling-mounted water feature and a large steam shower. The lower level adds flexibility with a bonus room, separate office & ample storage. Deeded parking, in-unit laundry, central A/C, a new hot water heater & newer HVAC complete the package. Sip coffee on your deck, unwind to the sounds of waves & seagulls, & make every day feel like a vacation!

54 Trident Ave Unit 54, Winthrop

$649,900

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584839 MLS ⋅ 1,925 SqFt.

A rare opportunity to own a spacious Folk Victorian cherished by the same family for four generations. Tucked away on a quiet dead end street, this 1,925 sq. ft. home welcomes you with a classic screened front porch and an impressive amount of living space inside. The expansive first floor features open concept living and dining with parquet floors and a built in serving cabinet, plus an oversized kitchen with plenty of cabinet and counter space, stainless steel appliances, a gas range and 10 foot ceilings waiting to be revealed. A spacious den with a freestanding gas stove offers another inviting gathering space, along with a full bath and first floor laundry. Sliders lead to the deck and backyard, where an in ground pool and patio with gazebo create a fantastic setting for summer entertaining. Upstairs are three generously sized bedrooms and a second full bath, with one bedroom opening directly onto a flat roof offering potential for a future deck or expansion. The finished third floor adds flexible space for a den, office or playroom, plus ample storage. Central heat and A/C and three car tandem parking add everyday comfort and convenience. Bring your vision and make this special home your own, with Winthrop’s coastal setting right outside your door, a short walk to Fisherman’s Bend, close to Winthrop Center, and minutes from Logan Airport and downtown Boston. Open House, Saturday 10/3 10:30 -12pm, Sunday 10/4 10:30 - 12pm

16 North Ave, Winthrop

$839,900

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584025 MLS ⋅ 1,942 SqFt.

Stunning single family home located in the desirable Town of Winthrop. This completely updated and spacious single family home offers four bedrooms with one and a half baths and plenty of space for everyone. Additional bonus rooms on the attic level and a large unfinished basement provide even more opportunities for expanded living. An open floor plan and a beautiful kitchen, complete with stainless steel appliances and upgraded countertops make this a perfect home for entertaining. Hardwood flooring throughout, central forced air, and ductless mini-splits round out some of the great features this home has to offer. An ample and airy backyard and off-street parking are a huge plus. Incredible location - just steps to the ocean and minutes to Downtown Boston, Logan Airport and the North Shore. See all that Winthrop has to offer - close to beaches, parks, restaurants and much more!

32 Elmwood Avenue, Winthrop

$679,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73582921 MLS ⋅ 1,144 SqFt.

Welcome to 7 Enfield Road, a captivating single-family residence in Winthrop, MA. Built in 1930, this inviting home spans 1144 square feet and is ready for you to move in. It offers a unique blend of classic charm and comfortable living, set on a generous 6969 square foot lot. The living room provides a warm and inviting atmosphere, centered around a charming fireplace, and features elegant hardwood flooring that extends throughout the space. The bedrooms, designed for comfort and tranquility, also boast classic hardwood flooring, creating a cohesive and timeless feel throughout the private areas of the home. This property also includes a convenient one-car garage, a full basement offering ample storage or potential for future customization, and a welcoming porch perfect for enjoying the outdoors. Discover the effortless lifestyle awaiting you at this charming Winthrop address. Convenient location to Winthrop Center and shopping, Cummings Elementary School or walk to Ingleside Park, tennis and basketball courts, pickle ball courts and Donovan's beach.

7 Enfield Road, Winthrop

$1,500,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73582288 MLS ⋅ 2,852 SqFt.

The street name—Harbor View Avenue—says it all! A home any sea captain would be proud to call home! Rare opportunity to own a distinctive multi-family property perched at one of Winthrop’s highest elevations, with sweeping panoramic views of the ocean and Boston Harbor and Skyline. Enjoy spectacular sunrises, sunsets, passing boats, and refreshing ocean breezes from this exceptional coastal setting. Classic Hardie Board siding adds timeless New England character, while public stairs just steps away provide convenient access to Yirrell Beach and its shoreline walks. The flexible multi-family layout offers excellent options for an owner-occupant, multi-generational living, or investment income. The current configuration also provides the potential to convert the property into a spacious four-bedroom single-family home. The owner is currently awaiting Massport approval for replacement windows and doors. Elevated location, exceptional ocean and harbor views, beach access, classic coastal character, and versatile living possibilities make this a truly special Winthrop property. Check out our video with the QR code or cut and paste this link: https://tour.vaulted-media.com/63_harbor_view_ave-4103

63 Harbor View Ave, Winthrop

$449,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73582000 MLS ⋅ 805 SqFt.

Whether you’re buying your first home or looking to simplify your life with easy one-level living, this beautifully renovated and meticulously maintained 2-bedroom condo checks all the boxes! Located entirely on the first floor with no stairs required, the home offers a bright, open-concept layout filled with natural light and an easy, move-in-ready lifestyle, just minutes from Winthrop Beach. The updated kitchen features white shaker cabinetry, granite countertops, stainless steel appliances, peninsula seating and plenty of storage, opening seamlessly into the spacious living area. The living area boasts space for a large sofa and television plus an extra storage closet. The generous primary bedroom is bright and inviting, with a double closet. It’s complemented by a versatile second bedroom, ideal for remote work, guests, or a roommate to help offset the mortgage, or simply a nice, bonus flex space. An updated full bath, in-unit laundry and dedicated parking add the everyday convenience of this home! Outside, enjoy your own exclusive patio space, perfect for morning coffee, summer grilling or relaxing after a day at the beach. An excellent option for a first-time buyer, empty nester or downsizer seeking low-maintenance, single-level living without sacrificing a second bedroom or private outdoor space. Convenient to Boston, Logan Airport and all that Winthrop has to offer, this seaside gem is ready for its next owner!

43 Sagamore Ave Unit 1, Winthrop

$965,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73579972 MLS ⋅ 1,978 SqFt.

The largest residence in the Pearl, loft-style living, high ceilings, oversized windows, and original wood details. The layout offers flexibility, including space that works well for a home office. Premium kitchen, radiant-heated primary bath,2 off-street parking spaces, private storage, and secure entry. Close to beaches, trails, cafes, and an easy ride into Boston. Also being offered for SALE & LEASE!

1001 Shirley St Unit 1, Winthrop

$815,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73579968 MLS ⋅ 1,665 SqFt.

Ready for more space? Unit4 at The Pearl offers 1,665 square feet of loft style living, ideal for buyers who have outgrown a starter condo. Soaring ceilings, oversized windows, original wood details and premium finishes give it character and room to spread out. Premium kitchen, radiant-heated primary bath, 2 off-street parking spaces, private storage and secure entry. All that plus Winthrop’s beaches, trails, cafés and quick access to Boston. Also available for lease see MLS

1001 Shirley St Unit 4, Winthrop

$299,900

1 Beds ⋅ 1 Baths ⋅ CONTINGENT Status ⋅ 73579862 MLS ⋅ 720 SqFt.

HERE IS A GREAT INVESTMENT OPPORTUNITY OR OWNER OCCUPY.....Why rent when this updated seaside condo can give you a start to have a place of your own? Conveniently located on the Bus Line to the Blue Line and just steps to the beach. This unit has been freshly painted, new grey vinyl flooring throughout, new updated fully applianced kitchen with white cabinets, quartz counters and good size rooms. A large main bedroom, generous living room and a bonus room/office all waiting for your personal touches. This area has some of the many great eateries that can be enjoyed around this amazing seaside town. SMALL TOWN LIVING JUST MINUTES TO BOSTON and LOGAN AIRPORT, DON'T MISS OUT !!

483 Shirley St. Unit 6A, Winthrop

$624,995

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73579407 MLS ⋅ 1,690 SqFt.

THIS ONE FEELS LIKE A SINGLE FAMILY HOME!!! Off in the distance you will enjoy spectacular sunsets over the water in this beautifully renovated and spacious two-level condominium offering 3 bedrooms, 2 full baths and an open layout ideal for ease of living and outside enjoy exclusive to this unit yard space with deck, paver patio and fire pit. Highlights include new paint, lighting, an updated kitchen, updated baths, central air, in-unit laundry, a striking staircase and more of those ocean views from various windows. Commuting is easy with the Boston bus line nearby, providing access to the T in approximately 15 minutes and Boston in about 30. The Winthrop Ferry offers another convenient option. Enjoy Winthrop’s beaches, waterfront trails, golf course, yacht clubs, and popular restaurants—all just minutes from Boston. No monthly association fee; owners share the insurance expenses, pets allowed, private outdoor spaces, and 2 car parking round up the benefits of this beautiful townhome! Each unit owner responsible for 1/2 the insurance costs - no condo fee otherwise!

62 Pleasant St Unit 2, Winthrop

$900,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73579256 MLS ⋅ 1,334 SqFt.

**$20k in seller credits available** Rare land offering directly across from Winthrop Beach. This 13,920 square foot (0.32 acre) residential parcel is offered together with the existing structure on it, a two-story gambrel home built in 1880 with 5 rooms, 3 bedrooms, 1.5 baths, forced hot water heat, and vinyl siding. Ocean views across from the beach reservation. Renovate the existing house, build new, or explore other options for the site; buyer and buyer agent to complete their own due diligence with the Town of Winthrop regarding zoning, permitted uses, and redevelopment potential. Public water and sewer serve the site. Quick access to Boston, Logan Airport, and MBTA connections.

93 1/2 Winthrop Shore Drive, Winthrop

$865,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579115 MLS ⋅ 1,564 SqFt.

A rare opportunity to own a lovingly cared for home in a truly special location! For over 50 years, the same owners have cherished this home, and it shows. Offering a flexible layout with first floor living, the main level features a spacious living room, dining room, and large eat-in kitchen, all with beautiful hardwood floors. A first floor bedroom and full bath provide the convenience of single level living. Just off the kitchen, a bright and inviting three season sunroom offers large windows and a peaceful place to relax while taking in spectacular sunsets over the city. Mini-splits on the first floor provide comfortable cooling, while the second level is equipped with central air.Upstairs are two additional cozy bedrooms and a half bath. The finished basement provides additional living space along with a three quarter bath and walk out access to the yard. Step outside to a spacious, private yard featuring a stone patio and garden perfect for entertaining, gardening, or simply enjoying the outdoors. Perhaps one of the property's most unique features is its **riparian rights for a dock**, with this being one of only two remaining homes on the street believed to retain these rights.Enjoy the best of coastal living with the beach just across the street, where you can watch beautiful sunrises, and sunsets from your own backyard. The ferry is also within walking distance, offering an easy commute into the city or a convenient way to head in for dinner and an evening out. Numerous updates provide peace of mind, including windows (2018), mini-splits (2019), water heater (2023), and roof (2008). A wonderful opportunity to own a home with character, history, outdoor space, and an exceptional waterfront lifestyle.

807 Shirley St, Winthrop

$799,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73578454 MLS ⋅ 1,782 SqFt.

**$20k in seller credits available** Sunlight defines this renovated three bedroom home a short, flat walk from the beach and harbor. A 23 foot window wrapped sunroom spans the front entry, and upstairs the primary suite opens to a private pine paneled sun porch with overhead glazing that runs the width of the house. The 2008 renovation opened the first floor into one connected space: a living room anchored by a gas stove, a 21 foot dining area, a dedicated office nook, and a cherry cabinet kitchen with granite counters, tile backsplash, double oven range, and stainless appliances. The first level also features a full bath and oak floors throughout. Upstairs, the spacious primary bedroom features access to a charming balcony-style sunroom - an ideal spot for relaxing, reading, or enjoying a quiet morning - and a tandem bathroom. Two additional bedrooms and a dedicated second-floor laundry room complete the level. Out back, a deck steps down to a paver patio with perennial beds, privacy fencing, and a storage shed. Two heating zones, central air on both floors, central vacuum, tankless hot water, and a poured concrete basement for storage. Three off street parking spaces behind a picket fenced front yard.

35 Triton Ave, Winthrop

$1,095,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73577096 MLS ⋅ 2,649 SqFt.

Welcome to 94 Winthrop Shore Drive, a truly unique home directly across from Winthrop Shore Beach, offering beautiful water views and an incredible coastal setting. The home is highlighted by a dramatic, light-filled main living area with soaring ceilings, expansive windows overlooking the water, hardwood floors, and distinctive architectural details. Generous living and dining spaces provide plenty of room for entertaining, while the flexible floor plan offers multiple possibilities for everyday living, extended family, guests, or a private retreat. Kitchen areas on both the upper and lower levels add convenience and flexibility to the home’s versatile layout. The basement provides valuable storage space along with a private sauna, adding another unique feature to the property. The boiler and water heater were replaced approximately in 2023, and mini-split systems provide cooling in various areas of the home for added comfort and convenience. Enjoy the character, versatility, and coastal lifestyle of this one-of-a-kind home in an exceptional location directly across from the beach and just minutes from Boston.

94 Winthrop Shore Dr, Winthrop

$540,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73575716 MLS ⋅ 756 SqFt.

Welcome to coastal living at its best — where ocean views meet beautiful golf course views, and the beach is just a five-minute walk from your front door.Fully rebuilt in 2025, this exceptional first-floor 2-bedroom, 2-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless.Step inside to gleaming hardwood floors, beautiful natural light, and an inviting open living space. The chef’s kitchen is beautifully designed with quality finishes, generous workspace and storage, creating a perfect setting for cooking, entertaining, or simply enjoying a quiet morning at home.The spacious primary suite is its own private retreat, complete with a beautifully designed spa-like bathroom. A second bedroom and full bath offer flexibility for family, guests, or a home office. Both bathrooms have been finished with the same attention to quality, comfort, and detail found throughout the home.And the beauty goes far beyond what you see. The home was completely rebuilt with modern comfort in mind, including hypoallergenic hydro-air heating and cooling, tankless hot water, high-quality systems and finishes, and thoughtful details throughout. This is not a quick renovation — it is a home where everything was considered and done with care.First-floor living makes the home especially convenient, and one dedicated parking space completes the package.But perhaps the best feature is the lifestyle.Wake up by the sea. Walk five minutes to the beach. Enjoy beautiful ocean and golf course views and the peaceful atmosphere of a coastal community, all while remaining incredibly close to Boston.2 bedrooms. 2 full baths. Primary suite. Spa-like bathrooms. Chef’s kitchen. Gleaming hardwood floors. One parking space. First-floor living. Ocean and golf course views. Fully rebuilt in 2025.A beautifully rebuilt coastal home in an extraordinary location — sophisticated, comfortable, and surrounded by the magic of Winthrop by the sea. Ferry to downtown is 3 min walk.

194 Washington Ave Unit 4, Winthrop

$575,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73575711 MLS ⋅ 912 SqFt.

Welcome to coastal living at its best — where ocean views meet beautiful golf course views, and the beach is just a five-minute walk from your front door.Fully rebuilt in 2025, this exceptional first-floor 2-bedroom, 2-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless.Step inside to gleaming hardwood floors, beautiful natural light, and an inviting open living space. The chef’s kitchen is beautifully designed with quality finishes, generous workspace and storage, creating a perfect setting for cooking, entertaining, or simply enjoying a quiet morning at home.The spacious primary suite is its own private retreat, complete with a beautifully designed spa-like bathroom. A second bedroom and full bath offer flexibility for family, guests, or a home office. Both bathrooms have been finished with the same attention to quality, comfort, and detail found throughout the home.And the beauty goes far beyond what you see. The home was completely rebuilt with modern comfort in mind, including hypoallergenic hydro-air heating and cooling, tankless hot water, high-quality systems and finishes, and thoughtful details throughout. This is not a quick renovation — it is a home where everything was considered and done with care.First-floor living makes the home especially convenient, and one dedicated parking space completes the package.But perhaps the best feature is the lifestyle.Wake up by the sea. Walk five minutes to the beach. Enjoy beautiful ocean and golf course views and the peaceful atmosphere of a coastal community, all while remaining incredibly close to Boston.2 bedrooms. 2 full baths. Primary suite. Spa-like bathrooms. Chef’s kitchen. Gleaming hardwood floors. One parking space. First-floor living. Ocean and golf course views. Fully rebuilt in 2025.A beautifully rebuilt coastal home in an extraordinary location — sophisticated, comfortable, and surrounded by the magic of Winthrop by the sea. Ferry to downtown is 3 min walk.

194 Washington Ave Unit 2, Winthrop

$825,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73575705 MLS ⋅ 1,780 SqFt.

Private Deck(400 sq ft ) with full purchase price! Welcome to coastal living at its best — where ocean views meet sweeping golf course views, and the beach is just a five-minute walk from your front door.Fully rebuilt in 2025, this exceptional 3-bedroom, 3-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a home that feels elegant, comfortable, and effortless.Step inside to gleaming hardwood floors and beautiful natural light flowing through the open living space. At the heart of the home is a chef’s kitchen with a large center island, quality finishes, and plenty of room to gather, cook, entertain, or simply enjoy your morning coffee while taking in the surroundings.The layout features TWO primary suites, each with its own beautifully designed, spa-like bathroom — private retreats with the feeling of a boutique hotel. Three full bathrooms throughout the home are finished with the same attention to quality and detail.And the beauty goes far beyond what you see. The home was rebuilt with modern comfort in mind, including hypoallergenic hydro-air heating and cooling, tankless hot water, high-quality systems and finishes, and thoughtful details throughout. This is not a quick renovation — it is a home where everything was considered and done with care.Two garage parking spaces complete the package — an incredible luxury so close to the ocean.But perhaps the best feature is the lifestyle.Wake up to ocean and golf course views. Walk five minutes to the beach. Spend your mornings by the water and your evenings watching the light change over the coast. Enjoy the peaceful feeling of a seaside community while remaining just minutes from Boston.3 bedrooms. 3 full baths. Two primary suites. Two garage spaces. Chef’s kitchen. Spa-like bathrooms. Ocean views. Golf course views. Fully rebuilt in 2025.A beautifully rebuilt home in an extraordinary location — sophisticated, comfortable, and surrounded by the sea. Water ferry to downtown is 3 min walk

194 Washington Ave Unit 3, Winthrop

$979,000

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73574628 MLS ⋅ 2,126 SqFt.

All offers due by Tuesday 9/15 at noon.Situated on one of Winthrops most desirable tree-lined streets in the most sought after neighborhood- the Maze, this charming four-bedroom home blends original character with thoughtful updates and inviting spaces for everyday living.The welcoming living room features a built-in window seat and wood-burning fireplace. An updated kitchen with butler’s pantry opens to the formal dining room with built-in china cabinet. A first-floor bedroom or den, new three-season sunroom, and oversized full bath with laundry add convenience and flexibility to your first floor plan. Upstairs are three spacious bedrooms, including an expansive primary bedroom spanning the length of the home with versatile space that offers endless possibilities for a home office, nursery, or sitting area, its a true private retreat! Or create a future primary suite by adding a private bath and walk-in closet. A partially finished basement provides additional living space, while the large walk-up attic offers tremendous potential for future expansion. Outside, enjoy a fully fenced, paved backyard with patio, built-in fire pit, and grassy area for kids and pets. A three-car driveway and detached garage with electricity heating and air conditioning, provide excellent parking and storage or flex space for a home gym. Located in the heart of the Maze, beloved Emerson Road, known for its strong sense of community and annual Block Party really is a special place to call home!

41 Emerson Rd, Winthrop

$525,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73574430 MLS ⋅ 1,270 SqFt.

Just moments from Winthrop Beach, this charming three-bedroom condo offers a bright and inviting place to call home in a wonderful coastal setting. Inside, a thoughtfully designed layout features spacious living and dining rooms that flow together, filled with natural light. Charming details, including dentil molding, add character throughout. The kitchen features updated countertops and stainless steel appliances, while three comfortable bedrooms, generous closet space and in-unit laundry add to the home’s functional layout. Newly rebuilt front and rear porches offer space to enjoy a morning coffee or unwind after a day at the beach. One off-street parking space and additional basement storage add everyday convenience. Close to the shoreline, local restaurants, schools and playgrounds, this home offers a wonderful opportunity to enjoy the relaxed coastal lifestyle of Winthrop, all within easy reach of Boston.

111 Locust St Unit 2, Winthrop

$849,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73573332 MLS ⋅ 1,770 SqFt.

Welcome to 25 Locust, a beautifully appointed 2023-built condo offering modern coastal living just one street from the beach in sought-after Winthrop by the Sea. Thoughtfully designed for both style and comfort, this impressive home features a bright, open-concept main living level perfect for everyday living and entertaining. At the heart of the home is a sleek designer kitchen featuring Bosch appliances, quartz countertops, white shaker cabinetry, and elegant brass hardware.The lower level is dedicated to a private and spacious primary suite, creating a true retreat from the rest of the home. A custom walk-in closet built out by California Closets provides exceptional storage, while the gorgeous en suite bath offers a spa-like experience with an oversized walk-in shower featuring dual shower heads. Upstairs you have generously sized bedrooms and a beautifully finished full bath providing flexible space for family, guests, or a home office. Outdoor living is equally inviting. An oversized composite deck with a motorized Sunsetter awning installed in 2025 offers the perfect setting for morning coffee, summer dinners, entertaining, or unwinding after a day at the beach. A common fenced yard provides additional outdoor space, while one off-street parking space adds everyday convenience. Set in the seaside community of Winthrop, 25 Locust delivers the coastal lifestyle so many buyers are searching for while keeping Boston within easy reach. Enjoy nearby beaches, ocean breezes, waterfront scenery, and Winthrop’s local dining scene and neighborhood favorites—all with convenient access to Boston and the surrounding Greater Boston area.

25 Locust St Unit 2, Winthrop

$899,000

7 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73573129 MLS ⋅ 4,251 SqFt.

PRICE IMPROVEMENT! Welcome to 190 Pleasant Street, a spacious two-family home offering approximately 4,251 square feet of living space across three levels. Featuring 13 total rooms, seven bedrooms, two full bathrooms and two half bathrooms, this property presents an excellent opportunity for an owner-occupant, investor or multigenerational household. Each unit offers generous living space, while the home’s flexible layout provides plenty of potential to customize and add value. Conveniently located near Winthrop’s beaches, local shops, restaurants, public transportation and Boston. Bring your vision and discover everything this well-located two-family property has to offer!

190 Pleasant St, Winthrop

$499,900

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73572947 MLS ⋅ 1,210 SqFt.

A True Pride of Home Ownership!!! LOW CONDO FEE comes w/This Meticulously Maintained 2 Bed 2.5 Bath Penthouse Condo w/ 2 OFF STREET PARKING SPACES is Nestled in a Quiet Residential Neighborhood Just Steps from 4 Beaches, EZ ACCESS TO Public Transportation, Fine Shops and Dining and is Only a 10 Minute Drive to Downtown Boston/Logan Airport. Natural Light Spills Into This Unit Through the Over Sized Windows and 3 Sky Lights on the 2nd Level. Other Notable Features Include Newly Installed Waterproof Vinyl Plank Flooring , Fresh Paint Throughout, Central Heat /AC, Custom Blinds, Galley Kitchen, In Unit Washer and Dryer, Recessed Lighting, Newer Oversized Windows on 2nd Level, Private Balcony Off Both Bedrooms w/ Ocean Views, Common Roof Deck w/ Ocean Views, Extra DEEDED Storage in Basement and Much Much More!!!

15 Ocean Ave Unit 203, Winthrop

$529,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73571733 MLS ⋅ 969 SqFt.

Welcome to 35 Somerset Avenue, Unit 3, a sophisticated two-bedroom, two-bath residence offering modern design and effortless coastal living in the heart of Winthrop. Thoughtfully renovated in 2023, the home features beautiful oak flooring and a bright, open-concept layout ideal for both everyday living and entertaining. The stylish kitchen is anchored by an oversized island and finished with quartz countertops, stainless steel appliances, subway tile accents, and contemporary pendant lighting. The spacious primary suite offers a private retreat with a beautifully appointed marble bath, while the second bedroom provides flexibility for guests, a home office, or additional living space. Step outside to your exclusive private deck, perfect for morning coffee or summer evenings. In-unit laundry, basement storage, and off-street parking complete the offering. Ideally situated near Winthrop Center's restaurants, cafés, shops, parks, and the waterfront, this turnkey home delivers the perfect blend of style, convenience, and coastal charm.

35 Somerset Ave Unit 3A, Winthrop

$580,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73569960 MLS ⋅ 931 SqFt.

Welcome to 33 Bay View Ave, a charming coastal bungalow offering the perfect blend of comfort, convenience, and seaside living in Winthrop. This 3-bedroom, 1-bath home features hardwood floors, a bright and inviting living space, dedicated dining area, and a functional kitchen with new appliances. Enjoy water views and take advantage of the spacious fenced in yard, ideal for entertaining, gardening, or relaxing outdoors. Additional highlights include an enclosed porch, wood deck, patio, first-floor laundry, and off street parking. Located just moments from the beach, parks, walking and biking trails, public transportation, and all that Winthrop has to offer. A great opportunity to enjoy the coastal lifestyle while remaining just minutes from Boston and Logan Airport.

33 Bay View Ave, Winthrop

$629,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73568805 MLS ⋅ 1,200 SqFt.

Opportunity knocks to own a beachside property!!! This highly desirable "tight knit" community have many homes that are passed down through the generations! This 3 bdrm, 1 3/4 bath Beach Bungalow is the perfect condo alternative with room to grow! The Main BDRM & FR have been fully renovated offering a Classic timeless design! New doors, recessed lighting, smooth ceilings, custom trim & crown molding, walk in closet, built in seating/cabinet, custom made covers for radiators, electric fireplace w/natural wood mantel & shiplap on the walls! Spacious bright and cheery Kitchen offers water views, New HDWD, New Paint throughout, Natural Gas range, New SS Refrigerator, DW and dining area! There's 2 additional rooms off of kitchen with water views, crown molding, new paint and HDWD. Large unfinished walkout (separate entry) basement has full bath w/shower stall, laundry, 3 door cedar closet offering endless possibilities to add an add'l 1200 sq.ft of living space! Updates also include Roof (2016), Washer & Dryer (2023), Hot water tank (12/2023). Conveniently hooked up to Town water & Town sewer. Front porch sunroom highlights beadboard ceiling, recessed lighting, HDWD flooring, surrounded by windows and adds an additional 144 sq ft of unheated space! Entertain friends, grill out, relax on your newly built expansive rear deck with steps to the beach! Start your day by catching the natural beauty of the "sunrise", swim, surf, sunbathe, kayak, paddleboard or head down the street in the evening for the amazing "sunset" views of the Boston skyline! Perfect year round or vacation home! Imagine living in a coastal neighborhood on a peninsula! Point Shirley residents enjoy all the amenities at Coughlin Park and the "Deer Island" walking path ~ both with it's city views! Bus service to Orient Heights train station, seasonal Ferry Service from Winthrop Landing to Seaport /Aquarium and only 5.6 miles to Logan Airport!

84 Tafts Ave., Winthrop

$947,900

6 Beds ⋅ 3 Baths ⋅ REACTIVATED Status ⋅ 73567723 MLS ⋅ 2,650 SqFt.

At this attractive new price, this is more than just a home, it’s a chance to embrace the coastal lifestyle that makes Winthrop so special! Just moments from the beach, this beautifully updated 6-bedroom Colonial offers the rare combination of timeless character, modern comfort, and a lot of room for everyone. Featuring over 2,600 square feet of living space (plus additional 600+ sq ft in finished basement) gleaming hardwood floors, fireplaces, a partially finished lower level, and a very welcoming front porch, every space invites you to relax, gather, and create lasting memories. Extensive upgrades, including updated electrical, plumbing, heating, central A/C and very efficient mini spit system. Outside, enjoy a good sized, fenced backyard, large 2-car detached garage, and plenty of off-street parking. At this price, opportunities like this are hard to find in this section of Winthrop! Come experience the charm, space, and value for yourself! Very easy to view! Book your appointment now before it is too late!

217 Pleasant Street, Winthrop

$723,999

3 Beds ⋅ 3 Baths ⋅ PRICE CHANGED Status ⋅ 73566786 MLS ⋅ 1,800 SqFt.

**To directly address high mortgage rates, SELLER WILL PAY CONCESSIONS of up to two discounted points to buy down the buyer's interest rate!** Welcome to coastal living at its finest in this truly unique and beautifully appointed townhome residence. Spanning three expansive levels, this exceptional three-bedroom, two-and-a-half-bath home seamlessly blends comfort, style, and privacy in the one and only seaside community of Winthrop 02152. Privately situated with its own separate entrance, this rare offering lives like a single-family home and features direct access to its own secluded backyard retreat — a perfect escape for relaxing, entertaining, or enjoying quiet moments outdoors. Inside, thoughtfully designed living spaces are filled with natural light and offer the ideal balance of elegance and functionality. Just one block from the beach, enjoy the very best of coastal living- and only minutes from downtown Boston, Logan Airport, and public transportation MBTA Orient Heights Blue Line for an effortless daily commute. CLOSING COST CREDITS available with purchase.

189 Shirley St Unit 1, Winthrop

$335,000

2 Beds ⋅ 1 Baths ⋅ PRICE CHANGED Status ⋅ 73563869 MLS ⋅ 649 SqFt.

If you are a beach person or enjoy a short commute to the city you've come to the right place. Take this opportunity to live in the perfect location at a price that is ideal. Your two bedroom one bath is the perfect size at just under 700 square feet with an additional 300 square feet in the attic that is deeded exclusively to you to use as you like. Enjoy fresh air on your roof deck or a view of the ocean down Neptune Ave. Hardwood floors, stainless appliances, recessed lights, newer kitchen and bath are just the beginning. Close to shopping, restaurants, library, book / coffee shops, golf, tennis, beach, conservation areas. Nearby bus to blue line / Orient Heights provides convenient access to Logan International Airport and surrounding communities, with Boston's downtown in 30 minutes.

175 Shirley Street Unit 5, Winthrop

$629,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73563678 MLS ⋅ 1,463 SqFt.

Completely renovated to the core with quality craftsmanship throughout, this exceptional property blends modern sophistication with the relaxed coastal lifestyle that makes Winthrop so special. This beautifully finished two-level unit offers a bright, open layout designed for comfortable everyday living and easy entertaining. The main level features a gorgeous white kitchen with modern appliances, quartz countertops and backsplash, and crisp, timeless finishes that flows seamlessly into the living area. Also on this level, a generously sized bedroom offers a private ensuite bathroom with double vanity and bathtub, along with a spacious walk-in closet. A convenient guest half bath, high ceilings, hardwood flooring, and in-unit laundry add to the ease and functionality of the home. Upstairs, the impressive primary suite offers a generous retreat with an oversized private bathroom featuring a double vanity, beautifully tiled shower, and spacious walk-in closet. Outside, dedicated garage parking and an electric vehicle charging station make coming and going effortless. Located within walking distance of some of Winthrop’s favorite neighborhood spots for coffee, lunch, and dinner, this home also offers easy access to transportation and major routes into Boston and beyond. When it’s time to unwind, Winthrop Beach is just moments away, offering the perfect setting for a peaceful shoreline walk, a relaxing beach day, or simply enjoying the calming ocean breeze. Winthrop isn’t just a place to live—it’s a lifestyle. This is a rare opportunity to own a completely move-in-ready property that combines modern luxury, thoughtful design, and the relaxed coastal lifestyle so many dream of.

21 Hutchinson St Unit 2, Winthrop

$549,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73563560 MLS ⋅ 874 SqFt.

Imagine coming home to the relaxed rhythm of coastal living, where the water is just moments away and the best of Winthrop is right outside your door. This beautifully renovated 2-bedroom, 2-bath condominium has been thoughtfully transformed into a stylish and welcoming retreat, offering partial water views and a fresh, move-in-ready interior. Enter to warm hardwood floors that flow throughout the home and a bright, inviting layout designed for both everyday living and entertaining. At the heart of the home, the updated kitchen pairs timeless style with modern convenience, featuring quartz countertops, custom cabinetry, and stainless steel appliances. Whether you’re enjoying a quiet morning, preparing dinner, or gathering with friends, the space feels both polished and comfortable. Two beautifully renovated bathrooms continue the home’s clean, contemporary aesthetic, while the two bedrooms offer flexibility for overnight guests, a home office, or additional living space. Private basement storage with direct access provides plenty of room for beach gear, bikes, and seasonal items, and a deeded parking space adds everyday ease. Beyond the front door, enjoy the charm and character that make Winthrop such a special place to live- from waterfront walks and days at the beach to neighborhood restaurants, local shops, and easy access to Boston. Beautifully updated and perfectly positioned to enjoy life by the coast, this is a home where you can settle in, slow down, and make the most of every season.

12 Sewall Ave Unit 2B, Winthrop

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