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26 Forrest St Unit 3, Winthrop
$462,000
3 Beds ⋅ 1 Baths ⋅ 73427739 MLS
Experience coastal living in this spacious 3-bedroom, 1-bath top-floor unit in desirable Winthrop, MA. Offering over 1,300 sq. ft. of living space, this home features the convenience of in-unit laundry, two private decks and two dedicated parking spaces. Enjoy ocean views from your private deck while sipping your morning coffee. Recent updates include, newer windows, newer roof, new oil tank and full blown insulation. Situated only 3 houses away from the beach! With its close proximity to Boston, you'll have the best of both worlds: a serene seaside retreat with easy access to the city. Don't miss this rare opportunity for comfort, location, and lifestyle. Open houses Sat 9/13 & Sun 9/14 11-1. Offers due Monday 9/15 4pm.

26 Forrest St Unit 3, Winthrop

Listing courtesy of Listing Agent: Richard Harkins from Listing Office: EWK Realty.

140 Shirley Street Unit 340, Winthrop
$460,000
1 Beds ⋅ 1 Baths ⋅ 73483298 MLS
Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking. Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

140 Shirley Street Unit 340, Winthrop

Listing courtesy of Listing Agent: Kovacs Savage Team from Listing Office: Byrnes Real Estate Group LLC.

34R Underhill St Unit 3, Winthrop
$450,000
2 Beds ⋅ 2 Baths ⋅ 73550972 MLS ⋅ ['34 Underhill Street Condominium'] BLDG.
This like-new 2-bedroom, 2 bath condo at 34 Underhill Street delivers the finish level of new construction at a fraction of the cost. Gut renovated and converted in 2020, every detail was approached with care, from the white shaker kitchen with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including gas cooking, to the wide plank hardwood floors that run throughout the entire unit. The primary bedroom features a custom walk-in closet with built-in shelving and drawers, and direct access to a full bath. The open living area is bright and generously sized with recessed lighting and mini-split systems for year-round comfort. Ground-floor entry with private access adds convenience rarely found in condo living. Set steps from the Winthrop coastline with the Boston ferry, Rt. 1A, and Logan Airport all just minutes away, this is a turnkey home in a location that continues to attract buyers who want coastal living without sacrificing quality.

34R Underhill St Unit 3, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

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

48 Crystal Cove Ave. Unit 2, Winthrop

Listing courtesy of Listing Agent: Rogelio Zuniga from Listing Office: United Brokers.

86 Undine Ave, Winthrop
$450,000
1 Beds ⋅ 1 Baths ⋅ 73463015 MLS
This offering is about the land, the view, and the opportunity to own an affordable single-family property in an exceptional location. Located in Point Shirley, one of Winthrop’s most sought after waterfront neighborhoods, this shovel ready property sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing single-family structure is currently dilapidated and presents a buyer with two paths: restore the home or pursue new construction. Zoning Board of Appeals approval has already been granted, making this a fully entitled, shovel-ready opportunity. A buyer simply needs to pull a building permit and begin construction. Existing structure is intended for tear down. Zoning Board of Appeals approval has already been granted and the project is fully entitled.

86 Undine Ave, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

140 Shirley Street Unit 240, Winthrop
$449,000
1 Beds ⋅ 1 Baths ⋅ 73470307 MLS
Discover the perfect blend of modern design and seaside charm at 130 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This one-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking (with the option to purchase a second space). Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston’s best-kept secrets.

140 Shirley Street Unit 240, Winthrop

Listing courtesy of Listing Agent: Kovacs Savage Team from Listing Office: Byrnes Real Estate Group LLC.

69 Summit Ave Unit 2, Winthrop
$445,000
2 Beds ⋅ 1 Baths ⋅ 73562221 MLS
WELCOME TO SUMMIT VIEW CONDOMINIUMS. This sun filled 2 bedroom unit boasts amazing views of the town of Winthrop and Boston skyline. Private deck with magnificent views and a huge back yard space. Great time to get in to be a part of a condo association. Great neighborhood, plenty of off street parking, just steps to Winthrop beach, 1 min to bus stop, just minutes to Orient Height T-Station, and to downtown Boston, easy access to North Shore. Large living and dining combo, newer tile kitchen, large primary bedroom with spacious organized closets, and sunfilled, views off your private deck , extra storage in basement, can install own washer and dryer and dishwasher in unit, or washer and dryer common with unit 1. Winthrop has so much to offer, great access to the city, restaurants, bars, shopping, entertainment, waking/jogging trails, marinas, yacht clubs and so much more

69 Summit Ave Unit 2, Winthrop

Listing courtesy of Listing Agent: Kevin Ferrara from Listing Office: Cottage Hill Real Estate.

25 Winthrop Shore Drive Unit 1, Winthrop
$432,500
2 Beds ⋅ 1 Baths ⋅ 73555750 MLS
Coastal living at its best! Just steps from the beach, this beautifully maintained 2-bedroom, 1-bath condominium offers the perfect blend of charm, comfort, and convenience. The bright, open-concept living and dining area flows seamlessly into a spacious kitchen featuring rich cabinetry, granite countertops, and large penninsula—ideal for entertaining. A sun-filled enclosed porch provides the perfect spot to enjoy your morning coffee or unwind after a day by the ocean. Additional highlights include low condo fees, ample street parking, generous private dry storage in the basement, and a small four-unit association. Whether you're looking for a year-round home, weekend retreat, or investment opportunity, this move-in ready condo offers an unbeatable location just moments from Winthrop's beaches, restaurants, and Boston.

25 Winthrop Shore Drive Unit 1, Winthrop

Listing courtesy of Listing Agent: Jenny Golic from Listing Office: Bowdoin Real Estate Partners.

10 Somerset Unit 404, Winthrop
$420,000
1 Beds ⋅ 1 Baths ⋅ 73456763 MLS
Welcome to Unit 404 at The Somerset—a premier boutique condo community in the heart of Winthrop. This thoughtfully designed studio features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The Somerset offers exceptional amenities, including a fitness room, elevator, and a cozy resident lounge ideal for remote work or casual gatherings. Just moments from sandy beaches, waterfront parks, and local restaurants—with easy access to downtown Boston via the Blue Line or seasonal ferry—this home blends coastal charm with city convenience. Whether you’re seeking your next home or a seaside retreat, Unit 304 delivers style and a lifestyle by the sea. Schedule your tour today!

10 Somerset Unit 404, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.

900 Shirley Street, Winthrop
$415,000
2 Beds ⋅ 1 Baths ⋅ 73430474 MLS
NEW AMAZING PRICE! INCREDIBLE OPPORTUNITY, UNLIMITED POTENTIAL.......Single family living/condo alternative in the quaint oceanside location of Point Shirley in Winthrop by the Sea! A desirable open floor plan consists of Living room, Dining room and kitchen with beautiful oak flooring and a very nice large updated full bathroom and 2 good size bedrooms. All on one level for easy living. Ocean breezes, amazing sunrises and sunsets abound for your peaceful enjoyment and natural beauty! The fun awaits with so many choices to make it your own. Two car off street parking and easy access to the beach! ***This Property has been approved for all new windows and doors**** With the The Massport Soundproofing Program. GREAT INVESTMENT PROPERTY and IDEAL AS A SUMMER HOME TOO!!

900 Shirley Street, Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.

53 Trident Ave Unit 204, Winthrop
$400,000
2 Beds ⋅ 1 Baths ⋅ 73474408 MLS
Ideally situated just a few homes from the beach, this two-bedroom, pet-friendly condo offers the perfect opportunity to enjoy coastal living in Winthrop. Thoughtfully updated and well maintained, the home blends modern comforts with an unbeatable seaside location. This home features a refreshed kitchen with brand-new stainless steel appliances and a stylish tile backsplash. One of the bedrooms enjoys ocean views, adding a true coastal feel to the space. The layout is both comfortable and functional, suitable for a primary residence, second home, or investment. The building has undergone extensive recent improvements, including new carpeting, siding, roof, freshly painted hallways, and a new furnace, providing peace of mind and low-maintenance ownership. After a long New England winter, imagine stepping into warmer months with the beach just steps away. Enjoy Winthrop’s shoreline, waterfront parks, and easy access to Boston, Logan Airport, and public transportation.

53 Trident Ave Unit 204, Winthrop

Listing courtesy of Listing Agent: Domenico Barbuto from Listing Office: DJB Realty Corporation.

47 Prospect Ave Unit 47, Winthrop
$400,000
4 Beds ⋅ 3 Baths ⋅ 73446404 MLS ⋅ ['Cottage Hill'] BLDG.
Experience some of the finest views in all of the city from this stunning location on Prospect Avenue. The upper-level kitchen and living area are positioned to take full advantage of the natural light and stunning scenery, featuring an open floor plan that highlights the views from every angle. The roof access provides a one-of-a-kind vantage point overlooking the harbor. The second floor features three comfortable bedrooms, providing space and flexibility for family or guests. With ample off-street parking and a location just a short distance from Winthrop’s beaches, marina, and local restaurants—this home offers the best of coastal living. Estate sale. Property to be sold as-is and will not qualify for conventional financing.

47 Prospect Ave Unit 47, Winthrop

Listing courtesy of Listing Agent: Adam Gustafson from Listing Office: Today Real Estate, Inc..

600 Shirley St Unit 1, Winthrop
$399,000
1 Beds ⋅ 2 Baths ⋅ 73481124 MLS ⋅ ['The Cove At 600'] BLDG.
$6,000 closing cost credit to buyer!!! WATER VIEWS & PRIVATE DECK! Welcome to The Cove at 600, a premier condominium development in Winthrop, situated on the historic site of the Crystal Cove Hotel. This meticulously renovated first-floor unit features 1 bedroom and 2 baths, epitomizing perfect beach town living. Every detail has been updated finishes, including newer kitchen & bathrooms. Your living room offers stunning water views, creating a serene and picturesque setting. This unit offers a generous sized bedroom and ample closet space top to bottom. Two parking spots add to the convenience for commuting. Start your mornings with a coffee on your private balcony, soaking in breathtaking views of Boston and the Crystal Cove Ocean, right across the street. The common lobby is thoughtfully designed to maximize stunning Boston Harbor views. The vibrant Winthrop downtown area, with its charming restaurants and shops, is just a short distance away. Don't miss your chance!

600 Shirley St Unit 1, Winthrop

Listing courtesy of Listing Agent: The Movement Group from Listing Office: Compass.

247 Washington Ave Unit 10, Winthrop
$393,000
1 Beds ⋅ 1 Baths ⋅ 73484073 MLS
Rare opportunity to own a harbor front condo with beautiful marina and water views in desirable Winthrop. This bright second-floor unit features an open layout and updated kitchen with granite countertops, stainless steel appliances, recessed lighting, and a peninsula that opens to the living area. Sliding glass doors lead to a private balcony overlooking the water, perfect for relaxing and enjoying the coastal setting. The spacious bedroom offers a walk-in closet and its own slider with balcony access and the same scenic views. Elevator building with deeded off-street parking and common laundry. Ideally located near beaches, marina, parks, restaurants, shopping, and public transportation with easy access to Boston.

247 Washington Ave Unit 10, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

1000 Governors Drive Unit 25, Winthrop
$385,000
2 Beds ⋅ 1 Baths ⋅ 73445447 MLS
Welcome to Governor’s Park Condominiums in Winthrop! This well-maintained third-level, two-bedroom, one-bath unit offers the perfect balance of city convenience and coastal charm. Featuring an open-concept layout with a spacious living room and kitchen/dining area, this home also includes hardwood floors, granite countertops, SS appliances, a private balcony, and two deeded off-street parking spaces. The professionally landscaped grounds and common areas enhance the appeal of this desirable community. Ideally located just 10 minutes from downtown Boston and Logan Airport, a short distance to Orient Heights T Station, and only a 3-minute walk to the scenic Belle Isle Marsh Reservation, this condo is a commuter’s dream and a rare opportunity to enjoy peaceful, seaside living near the city. Don’t miss your opportunity to own a home in one of Greater Boston’s most charming coastal towns. Schedule your private showing today!

1000 Governors Drive Unit 25, Winthrop

Listing courtesy of Listing Agent: Lindita Murrizi from Listing Office: Return Realty Group, Inc..

10 Somerset Unit 403, Winthrop
$383,542
1 Beds ⋅ 1 Baths ⋅ 73378713 MLS ⋅ ['The Somerset'] BLDG.
The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage parking, and select units feature private decks, perfect for enjoying the ocean breeze. The building itself offers convenient amenities like an elevator, fitness center, and a welcoming common lounge—ideal for working remotely or catching up with neighbors over coffee. Moments from Winthrop’s beaches, just a short stroll from shops, restaurants, and the scenic shoreline. Easy commute to downtown Boston via the MBTA Blue Line or the seasonal Winthrop Ferry. Just looking for a seaside retreat with city access, The Somerset offers the best of both worlds.

10 Somerset Unit 403, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.

100 Governors Drive Unit 118, Winthrop
$380,000
2 Beds ⋅ 1 Baths ⋅ 73469974 MLS ⋅ ['Governors Park Drive'] BLDG.
FINALLY!!! A Villager unit for sale in the sought after 100 Building! These 2 bedrooms in Governors Park has a renovated bathroom, newer windows and has been freshly painted. Best of all, Unit 118 is on the TOP FLOOR and features a balcony with views of the top of the Boston skyline, where you can also enjoy AMAZING sunsets. This complex features a clubhouse, gym room, in ground pool and tennis courts and is just a short walk from Winthrop beach. Walk across the street and go to the market, grocery store, bakery or to one of the many diverse and delicious restaurants this quaint town has to offer. Live here and live just 15 minutes to Downtown Boston or take the bus and in just 6 minutes you will be at Orient Heights train station. Condo fee INCLUDES heat & hot water. This one REALLY will not last!

100 Governors Drive Unit 118, Winthrop

Listing courtesy of Listing Agent: Pratt Properties Team from Listing Office: Century 21 North East.

1000 Governor's Drive Unit 15, Winthrop
$370,000
2 Beds ⋅ 1 Baths ⋅ 73559730 MLS
This bright 2 bedroom 1 bathroom unit is the perfect space for a new owner to put their stamp on! The main bedroom has laminate flooring which is in excellent condition and the rest of the unit is carpeted. Heating and cooking for the condo is gas and there are 2 in-wall air conditioners...one in the living room and one in the main bedroom. The kitchen appliances are all in great shape. You can also have your coffee out on your private balcony. Governor's Park complex is in a great location close to shopping, the beach and public transportation. There is an in-ground pool for residents to enjoy as well. You are welcome to OPEN HOUSES THIS WEEKEND...Saturday 8/8 from 11am-1pm and Sunday 8/9 from 11am-12:30pm!

1000 Governor's Drive Unit 15, Winthrop

Listing courtesy of Listing Agent: Kenny Kelleher from Listing Office: Compass.

300 Governors Dr Unit 21, Winthrop
$370,000
2 Beds ⋅ 1 Baths ⋅ 73497859 MLS
Open House Sunday 04/26 1-2pm. Rarely available corner-unit condo offering exceptional privacy and abundant natural light. (Situated at the corner of the building, this home benefits from a side entrance that feels like private access). Freshly painted, the unit features a well-designed layout with comfortable living spaces and a seamless flow ideal for everyday living or entertaining.Located in desirable Winthrop, a vibrant seaside community just minutes from Boston, Logan Airport, and major routes. Enjoy easy access to Winthrop Beach, Deer Island, scenic waterfront paths, local shops, restaurants, and public transportation, all while maintaining a quieter residential feel. An excellent opportunity for buyers seeking convenience, coastal charm, and a sense of privacy rarely found in condo living.

300 Governors Dr Unit 21, Winthrop

Listing courtesy of Listing Agent: Alla Rossi from Listing Office: Coldwell Banker Realty - Boston.

9 Atlantic St Unit 2, Winthrop
$362,500
2 Beds ⋅ 1 Baths ⋅ 73454898 MLS ⋅ ['9 Atlantic Street'] BLDG.
Priced Well Below Market Price - Experience the best of coastal living just minutes from Boston—close to the city without the high prices! This bright and spacious home features soaring ceilings, abundant natural light, large rooms, and hardwood floors. The traditional dining room with a built-in cabinet adds classic charm, while the fully applianced kitchen offers warm wood cabinetry and an oversized pantry. Enjoy morning coffee or evening breezes on either of two private porches. Each unit includes its own washer and dryer in the basement, and the pet-friendly building is well-maintained with a low condo fee. Perfectly located near Winthrop’s beautiful beaches, scenic trails, and popular local restaurants. Priced to sell quickly—come see why this is the best value on the coast!

9 Atlantic St Unit 2, Winthrop

Listing courtesy of Listing Agent: Mark Anderson from Listing Office: Redfin Corp..

1000 Governors Dr Unit 4, Winthrop
$360,000
2 Beds ⋅ 1 Baths ⋅ 73510931 MLS ⋅ ["Governor's Park Codominium"] BLDG.
Get ready to discover your next dream home! A fantastic condo for sale in the vibrant town of Winthrop, MA. This inviting residence features two generously sized bedrooms and a modern bathroom, complemented by an open concept living room and kitchen area.Situated in a large, welcoming complex, you'll enjoy excellent amenities including a tennis court and convenient laundry facilities in the building. The location couldn't be better—just a quick drive to Logan Airport and the Blue Line, making your commute and travel plans a breeze. If you’re looking for a blend of comfort, convenience, and community, this condo could be just the place for you! Don’t miss out on the chance to make it yours. Natural trail directly to the beach, fitness center and community pool. Some pictures are virtually staged.

1000 Governors Dr Unit 4, Winthrop

Listing courtesy of Listing Agent: Jose Rojas from Listing Office: William Raveis R.E. & Home Services.

203 Winthrop Shore Dr Unit 2, Winthrop
$357,000
1 Beds ⋅ 1 Baths ⋅ 73485475 MLS ⋅ ['Grandview Shore Condominium Association'] BLDG.
Oceanfront living just minutes from Boston! This bright first-floor one-bedroom condo sits directly across from Winthrop Beach in a classic seaside building with wraparound porches offering sweeping Atlantic views. With windows on three sides, the 725 sqft home is filled with natural light all day. The living room features hardwood floors and recessed lighting, while the kitchen with white cabinetry and durable flooring opens to a private porch—perfect for enjoying the salty ocean air. The spacious corner bedroom easily accommodates a queen or king bed and offers beautiful light throughout the day. Full bath with tiled tub/shower. Pet friendly with reasonable HOA fees! Additional highlights include off-street assigned parking plus guest parking, new gas-fired boiler, ample closets, basement storage and common laundry. Close to beaches, marinas, Winthrop Yacht Club, restaurants, Logan Airport and public transportation—yet outside the flight path.

203 Winthrop Shore Dr Unit 2, Winthrop

Listing courtesy of Listing Agent: Molly Walker from Listing Office: Coldwell Banker Realty - Scituate.

800 Governors Drive Unit 30, Winthrop
$357,000
2 Beds ⋅ 1 Baths ⋅ 73445405 MLS ⋅ ['Governors Park Condominium'] BLDG.
Move in ready, bright top floor 2 bedroom corner unit with lots of natural light! Freshly painted, beautiful sparkling hardwood floors throughout! White painted kitchen cabinets with newer appliances that include SS refrigerator, stove, dishwasher, and disposal. Two new built in wall a/c units. Newly rebuilt balcony with a partial Marsh water view. Governors Park is located in the small town of Winthrop, surrounded by the Atlantic Ocean and Boston Harbor with miles of beaches, marinas, yacht clubs and a 9 hole golf course! Additional amenities include all new schools, new athletic field and numerous renowned restaurants. Convenient Bus stop at the entrance of this complex takes you to the Blue Line Train at Orient Heights and on to downtown Boston, literally in minutes! Exceptional opportunity to own this affordable condo in Winthrop by the Sea.

800 Governors Drive Unit 30, Winthrop

Listing courtesy of Listing Agent: Linda Calla from Listing Office: Cottage Hill Real Estate.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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