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63-69 Putnam St, Winthrop
$2,250,000
16 Beds ⋅ 14 Baths ⋅ 73531829 MLS
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

Listing courtesy of Listing Agent: The Bill Butler Group from Listing Office: Leading Edge Real Estate.
63-69 Putnam St, Winthrop
$2,250,000
73490169 MLS
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.

63-69 Putnam St, Winthrop

Listing courtesy of Listing Agent: The Bill Butler Group from Listing Office: Leading Edge Real Estate.
174 Bartlett Road, Winthrop
$2,100,000
5 Beds ⋅ 6 Baths ⋅ 73550891 MLS
One of the most coveted locations in Winthrop, 174 Bartlett Rd is your dream costal retreat where luxury meets seaside living. Completely gut renovated, this exceptional home offers over 6,000 sq ft of beautifully designed living space across four expansive levels. The heart of the home is the stunning chefs kitchen with seamless oversized Brazilian Quartzite island surrounded by premium Sub-Zero, Wolf & Miele appliances, & a fully appointed entertaining bar. Anchored by a striking Valor fireplace, the two thoughtfully designed seating areas & expansive dining room create space for intimate or larger-scale entertaining. The Primary suite is a water view retreat with steam shower & BainUltra therapeutic soaking tub, dual walk-in closets, & private laundry. Welcome guests in the lower level suite, enjoy resort style yard with Gunite in-ground pool, basketball court & grilling island, or end days on the roof top deck with incredible views. This thoughtfully crafted home is unforgettable!

174 Bartlett Road, Winthrop

Listing courtesy of Listing Agent: Atiyeh Cassidy from Listing Office: Blue Sky Realty.
63 Harbor View Ave, Winthrop
$1,500,000
4 Beds ⋅ 2 Baths ⋅ 73582288 MLS
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

Listing courtesy of Listing Agent: Brian Perrin from Listing Office: Brian J. Perrin Real Estate.
129 Strandway, Winthrop
$1,275,000
4 Beds ⋅ 3 Baths ⋅ 73585487 MLS
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

Listing courtesy of Listing Agent: Kyle MacNichol from Listing Office: Redfin Corp..
23-25 Fremont St, Winthrop
$1,250,000
6 Beds ⋅ 3 Baths ⋅ 73588891 MLS
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

Listing courtesy of Listing Agent: Alla Rossi from Listing Office: Coldwell Banker Realty - Boston.
3 Seal Harbor Rd Unit PH33, Winthrop
$1,230,000
3 Beds ⋅ 3 Baths ⋅ 73560746 MLS ⋅ ['Seal Harbor Condominiums'] BLDG.
Experience elevated waterfront living in this stunning 3 bedroom, 3 bath penthouse at the prestigious Seal Harbor III. This exceptional two-level residence features a spacious open-concept floor plan designed to maximize natural light and showcase its spectacular waterfront setting. Entertain effortlessly or simply relax on the massive private deck, offering the perfect space to enjoy ocean breezes and breathtaking views. The kitchen boasts SS appliances, granite counters, Poggenpohl cabinetry and a breakfast bar. Enjoy the beautiful views while cooking. This 2 level unit offers the flexibility of a first floor bedroom and/or office. Nice open staircase. Lovely primary bedroom with en suite. There is a separate jacuzzi room which could become a home office if one chooses to do so. Seal Harbor III offers an unmatched lifestyle with exceptional amenities, including 24/7 concierge, a beautiful fireplaced lobby, an indoor heated pool and hot tub, a recently renovated fitness center, sauna, rooftop deck with panoramic views, outdoor swimming pool, tennis courts and multiple private resident gathering spaces. Additional highlights include a rare heated two-car garage, G9 and G11. Ideally located in the seaside community of Winthrop, you'll enjoy the tranquility of waterfront living while being just minutes from Logan Airport and downtown Boston, providing the perfect balance of coastal charm and city convenience. LUXURY, LOCATION, AND LIFESTYLE come together in this extraordinary waterfront Penthouse.

3 Seal Harbor Rd Unit PH33, Winthrop

Listing courtesy of Listing Agent: Cathie Curran from Listing Office: Charlesgate Realty Group, llc.
94 Winthrop Shore Dr, Winthrop
$1,095,000
2 Beds ⋅ 3 Baths ⋅ 73577096 MLS
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

Listing courtesy of Listing Agent: The Movement Group from Listing Office: Compass.
32 Irwin St, Winthrop
$1,049,900
6 Beds ⋅ 4 Baths ⋅ 73534385 MLS
Multi-family in Winthrop, MA with four apartments and an ocean view, within 1/10 mile of the beach. The mix is a 3-bedroom, 2-bedroom, 1-bedroom and studio, each with 1 full bath, totaling 2,949 sq ft. The third-floor 1-bedroom is leased at $1,500 per month and conveys. The first-floor 3-bedroom and second-floor 2-bedroom are delivered vacant at closing. The second-floor studio with sunroom is listed for rent at $1,700. Rents total $9,300 per month; three of four are projected. All rents include water; the studio and 1-bedroom also include heat, electricity and gas. Heat is gas hot water baseboard on 3 systems, with window AC and town water and sewer. The 1900 building has vinyl siding, an asphalt roof, LVP and hardwood floors, and an unfinished basement with exterior access. The 4,075 sq ft lot has 3 off-street parking spaces. The building department classifies it as 3 units and the assessor as 4; it is used as 4 units. Winthrop Golf Club, Shirley Street and Logan Airport are nearby.

32 Irwin St, Winthrop

Listing courtesy of Listing Agent: Michael Giannone from Listing Office: The Aland Realty Group LLC.
250 Washington Ave, Winthrop
$999,900
2 Baths ⋅ 73493587 MLS
2 BAY MECHANIC SHOP. Corner lot commercial building in a great location. Property features a two-bay garage with 2 lifts 15-foot ceilings, approximately 1,152 sq. ft. of interior space, office, and 2 half baths. FHA heating system with new motor and pump installed about 6 months ago. 200-amp circuit breakers. Rubber roof older. Situated on a 6,500 sq. ft. lot.Plot plan is attached. Many possible uses, including car lot, taxi stand or other business opportunities. Potential for future development may exist. Buyer & Buyer agent to do own due diligence.

250 Washington Ave, Winthrop

Listing courtesy of Listing Agent: Phil Consolo from Listing Office: Century 21 North East.
66 Sunnyside Ave, Winthrop
$999,888
5 Beds ⋅ 2 Baths ⋅ 73529063 MLS
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

Listing courtesy of Listing Agent: Mirna Monterrosa Orellana from Listing Office: COM-PRO Real Estate Services, Inc.
44 Bowdoin Street, Winthrop
$989,000
3 Beds ⋅ 4 Baths ⋅ 73592852 MLS
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

Listing courtesy of Listing Agent: Jenny Golic from Listing Office: Bowdoin Real Estate Partners.
316 Bowdoin St, Winthrop
$979,000
4 Beds ⋅ 3 Baths ⋅ 73593881 MLS
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

Listing courtesy of Listing Agent: Jay Karuna Ratne from Listing Office: Venture.
200 Main St Unit 1, Winthrop
$975,000
3 Beds ⋅ 3 Baths ⋅ 73557515 MLS
Brand-new construction in the heart of Winthrop, offering a rare opportunity to own a thoughtfully designed new-build townhome in a coastal setting just outside of the city. As construction progresses, buyers may have the opportunity to personalize select interior finishes, making this home uniquely their own. Spanning approximately 2,100 square feet across two levels, the home features an open-concept kitchen, living, and dining area, along with a first-floor bedroom, full bath, and welcoming entry foyer. Upstairs, two spacious bedrooms each offer a private en-suite bath, with conveniently located second-floor laundry. Enjoy a private yard, city views, and one dedicated parking space. Located just minutes from Boston, Logan Airport, Winthrop Center, beaches, local shops, and restaurants, this is one of only two newly constructed townhomes at this address... a truly uncommon opportunity in Winthrop.

200 Main St Unit 1, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
1001 Shirley St Unit 1, Winthrop
$965,000
2 Beds ⋅ 3 Baths ⋅ 73579972 MLS ⋅ ['The Pearl'] BLDG.
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

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.
28 Thornton Park Unit B, Winthrop
$949,000
3 Beds ⋅ 4 Baths ⋅ 73594122 MLS
Welcome to 28 Thornton Park, a stunning new-construction luxury townhouse in the heart of Winthrop. Spread across three thoughtfully designed levels, this home blends timeless architectural character with the comfort and quality of brand-new construction, all just minutes from Boston. The lower level basement is great height and could be finished.The sun-filled first floor is made for living and entertaining. Graceful arches, custom details and walls of windows fill the open layout with beautiful natural light. The gorgeous living room features soaring cathedral ceilings and flows into the dining area and a chef's kitchen designed for everyday cooking and holiday gatherings alike. Large sliding doors open to the outdoors for easy indoor-outdoor living, and a convenient half bath completes the level. The second floor is home to a true primary suite, a peaceful retreat at the end of the day. A second bedroom and a full bath make this level ideal for family or guests. The third floor adds even more flexibility, with another bedroom, a full bath and a beautiful home office. It's perfect for working from home, a guest suite or a quiet creative space. The home is still under construction, which means you have the rare opportunity to choose your own finishes and make it truly yours. Estimated completion is February 2027.Winthrop offers the best of seaside living with unbeatable convenience. Enjoy miles of beaches, waterfront parks, scenic walking paths, the harbor and a charming town center with local shops and restaurants. Logan Airport is minutes away, and downtown Boston is easily reached by car, the Blue Line or the ferry, making it ideal for commuters and travelers alike.

28 Thornton Park Unit B, Winthrop

Listing courtesy of Listing Agent: Faina Snitkovsky from Listing Office: Core Real Estate.
217 Pleasant Street, Winthrop
$939,000
6 Beds ⋅ 3 Baths ⋅ 73567723 MLS
UNBELIEVABLE VALUE MEETS UNMATCHED OPPORTUNITY. The best value proposition in Winthrop. Sellers are highly motivated and have re-priced the property aggressively to prompt a sale. Buyers can secure instant equity for the newly optimized price point. 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

Listing courtesy of Listing Agent: Louis Bonavita from Listing Office: Benton Real Estate Company.
43 Loring Rd, Winthrop
$919,900
3 Beds ⋅ 2 Baths ⋅ 73513222 MLS
Single Home, Great Location Great Shape Ready to Move In.

43 Loring Rd, Winthrop

Listing courtesy of Listing Agent: Jason Saphire from Listing Office: www.HomeZu.com.
93 1/2 Winthrop Shore Drive, Winthrop
$900,000
3 Beds ⋅ 2 Baths ⋅ 73579256 MLS
**$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

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
93 1/2 Winthrop Shore Drive, Winthrop
$900,000
73577509 MLS
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

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
115 Read St Unit 2, Winthrop
$889,000
3 Beds ⋅ 2 Baths ⋅ 73596305 MLS
Welcome to 115 Read Street! Experience the perfect blend of modern luxury, style, and convenience in this stunning new construction townhouse style condominium in the heart of Winthrop! This beautifully designed 3-bedroom, 2-bath residence offers a spacious, open-concept floor plan featuring a sun filled living area, elegant dining space, and a gorgeous kitchen complete with top of the line appliances and quality finishes throughout. Enjoy the warmth and ambiance of electric fireplaces, generously sized bedrooms, and the comfort of your own private entrance. Thoughtfully designed across multiple levels, this home offers the ideal combination of space, functionality, and privacy. Additional features include off street parking, separate basement storage, and beautifully landscaped grounds. Ideally situated just minutes from Winthrop's beautiful beaches, local restaurants, shops, and downtown Boston, this exceptional property offers the best of coastal living with easy access to the city. Don't miss this incredible opportunity to own brand new construction in one of Winthrop's most desirable communities!

115 Read St Unit 2, Winthrop

Listing courtesy of Listing Agent: Michael Cimmino from Listing Office: Real Broker MA, LLC.
115 Read St Unit 1, Winthrop
$869,000
3 Beds ⋅ 2 Baths ⋅ 73596306 MLS
Welcome to 115 Read Street! Experience the perfect blend of modern luxury, style, and convenience in this stunning new construction townhouse style condominium in the heart of Winthrop! This beautifully designed 3-bedroom, 2-bath residence offers a spacious, open-concept floor plan featuring a sun filled living area, elegant dining space, and a gorgeous kitchen complete with top of the line appliances and quality finishes throughout. Enjoy the warmth and ambiance of electric fireplaces, generously sized bedrooms, and the comfort of your own private entrance. Thoughtfully designed across multiple levels, this home offers the ideal combination of space, functionality, and privacy. Additional features include off street parking, separate basement storage, and beautifully landscaped grounds. Ideally situated just minutes from Winthrop's beautiful beaches, local restaurants, shops, and downtown Boston, this exceptional property offers the best of coastal living with easy access to the city. Don't miss this incredible opportunity to own brand new construction in one of Winthrop's most desirable communities!

115 Read St Unit 1, Winthrop

Listing courtesy of Listing Agent: Michael Cimmino from Listing Office: Real Broker MA, LLC.
1001 Shirley St Unit 2, Winthrop
$865,000
2 Beds ⋅ 3 Baths ⋅ 73596710 MLS ⋅ ['The Pearl'] BLDG.
Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy Boston access. Unit is listed for sale and lease!

1001 Shirley St Unit 2, Winthrop

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.
50-52 Bowdoin St, Winthrop
$849,000
6 Beds ⋅ 2 Baths ⋅ 73595333 MLS
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

Listing courtesy of Listing Agent: Mac Chinsomboon from Listing Office: Coldwell Banker Realty - Boston.
25 Locust St Unit 2, Winthrop
$849,000
3 Beds ⋅ 2 Baths ⋅ 73573332 MLS
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

Listing courtesy of Listing Agent: Sarah Fillmann from Listing Office: Coldwell Banker Realty - Boston.
27 Billows St, Winthrop
$840,000
3 Beds ⋅ 3 Baths ⋅ 73526371 MLS
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

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.
23 Sagamore, Winthrop
$839,000
4 Beds ⋅ 3 Baths ⋅ 73594196 MLS
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

Listing courtesy of Listing Agent: Elizabeth Ferrara from Listing Office: Cottage Hill Real Estate.
194 Washington Ave Unit 3, Winthrop
$825,000
3 Beds ⋅ 3 Baths ⋅ 73575705 MLS
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

Listing courtesy of Listing Agent: Ella Goren from Listing Office: Sunrise Realty & Investment LLC.
1001 Shirley St Unit 4, Winthrop
$815,000
2 Beds ⋅ 3 Baths ⋅ 73579968 MLS ⋅ ['The Pearl'] BLDG.
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

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.
43 Dolphin Ave, Winthrop
$799,900
5 Beds ⋅ 3 Baths ⋅ 73587974 MLS
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

Listing courtesy of Listing Agent: Patricia Nunez from Listing Office: Redfin Corp..

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