53 Winthrop, MA Real Estate Listings

Sort by:
$788,900Est. Payment
7 Beds | 3 Baths | 3,711 Sqft

71 Paine St, Winthrop, MA 02152

Multi Family For Sale

Welcome to 71 Paine Street, an oversized 2-family on a corner lot of Wilshire & Paine. Both units include private decks, off-street parking, separate heating systems, and divided basement space for storage & laundry. Unit 1 has a large footprint featuring 3 sizeable bedrooms, separate dining & living room areas, and an oversized mudroom and main entry. Additional highlights include beautiful hardwood floors throughout and a functional pantry room off the kitchen. Market rent for this unit is 2300-2400 conservatively. Heading up to the owner's unit that starts on the second floor, you'll find the same floor plan with 3 bedrooms. At the front of the house near the stairs is a bonus space perfect for working from home, or to use for remote learning. Head to the top floor where you'll have the owner's suite featuring an oversized bedroom, walk-in closet and bathroom, and a separate area for working out or additional office space. Single Family living in this 2 family, with rental income!

$685,000Est. Payment
5 Beds | 2 Baths | 2,204 Sqft

23 Sagamore Avenue, Winthrop, MA 02152

House For Sale

SPACIOUS, BEAUTIFUL and MOVE IN CONDITION! Three levels of living space starting with a stunning kitchen with granite counters, slate appliances, center island and it has gas cooking! Living room opens into the dining room and both have refinished hardwood flooring. A tiled full bath completes the first floor. The second floor has four bedrooms and a beautiful new tiled full bathroom. Up to the third floor you'll see another bedroom and a great playroom or home office space. This well maintained, tastefully renovated home has a new water line into the house and the roof and hot water tank have been replaced within the past two years. The yard is like a small resort. Fun places for all ages; fire pit/ patio area, garden area, and play area with a swing set which can stay. The retaining wall and fence are all new as is the driveway. Nothing to do but move in and be proud to call 23 SAGAMORE AVENUE your home. Close to so many places that Winthrop has to offer.

$765,000Est. Payment
5 Beds | 3 Baths | 3,957 Sqft

18 Tewskbury Street, Winthrop, MA 02152

Multi Family For Sale

Large 2 Family currently being used as a 3 family. Just steps from the beach and views of the city. This large two family has so many possibilities in which it can be used. Welcoming front porch with beautiful door and side lights. Unit one has beautiful hard wood floors and large living room, two bedrooms, kitchen and dining space open to each other. Unit 2 can be used as one large unit with 3rd floor. Unit 2 has 2 bedrooms, living room, dining room, and family room. 3rd floor can be used for extended family with 2 more bedrooms. Large fenced in yard, 3 car parking, and low maintenance siding. Roof 7-8 years old, 2 new water heaters replaced in 2019 and 2020. Washer & dryer to stay with home. This home would be wonderful for an owner occupied or rental investment. Discover Winthrop and all it has to offer this locations brings you the sunrise at the top of the street and sunset at the bottom of the street with the city as its backdrop. Great public transportation and restaurants.

$400,000Est. Payment
1 Bed | 1 Bath | 1,134 Sqft

15 Townsend St, Winthrop, MA 02152

House For Sale

You do not want to miss out on this opportunity to own a home located in the sought after area and prime location of Point Shirley in Winthrop by the Sea! You are around the corner from the beach, great walking/jogging trails, public transportation and parks. And with the great possibility to expand its a must see! Two lots with the total area of over 6,000 sqft.! The cottage offers an open floor plan with a bedroom, dining room and an office with ocean views. On the second floor you will find a great space that does require work but could be turned into a great size bedroom/office area. Two off street parking spots, a great size flat yard and solar panels are sure some of the highlights of this home! Potential for Investors/Developers/House hackers, neighborhood is designated opportunity zone.

$1,121,000Est. Payment
3 Beds | 1 Bath | 964 Sqft

89 Upland Road, Winthrop, MA 02152

House For Sale

HERE IS AN OCEANFRONT OPPORTUNITY OF A LIFETIME.......A HIDDEN ESCAPE, IN WINTHROP BY THE SEA, JUST MINUTES TO BOSTON! This unique property offers over 8,000 Sq. Ft. of land with a pretty country setting leading to a sweet vacation-style home set high on a hill overlooking the ocean. The first level has lots of large window to capture those amazing views from every room, literally walls of windows! Enter into a bright, eat in kitchen to one side and on the other, an open dining room/living room with wood floors, beam ceilings and a gas fireplace for cozy gatherings and personal enjoyment. There is plenty of off street parking (3+cars) and easy access to Boston by car, ferry and close to the T. Enjoy the incredible sunrises while having your morning coffee and live every day as if you are on vacation. Showings by appointment and pre-approved buyers only. First opportunity is Sunday 9/20 from 11-12:30.***COVID-19 GUIDELINES REQUIRED.

$689,000Est. Payment
4 Beds | 1 Bath | 1,997 Sqft

217 Pleasant St, Winthrop, MA 02152

House For Sale

For the first time in many years this Whittemore built home which is full of love, memories and an abundance of charm is being offered to you.This well maintained home still has originals such as natural woodwork,built-ins and a pocket door between LR/DR to name a few of the things that bring out the true beauty of this home. To anyone with a desire for craftsmanship and detail this home is sure to please and will not disappoint. The large living room with a fireplace and the dining room with built-ins make a great space for family time. Public record shows 4 BR however with 2 additional on the 3rd level and all with closets this could be considered 6 BR. Every room is great size.The front porch which comes with custom made screens is another great place to sit back and relax with a good book and your favorite beverage.The driveway leads to your 2 car garage and plenty of off st parking which is a bonus in this town. Massport windows and newer roof. Must see to appreciate !!

$249,000Est. Payment
2 Beds | 1 Bath | 937 Sqft

1100 Governors Dr #8, Winthrop, MA 02152

Condominium For Sale

location! location! location! Winthrop is the hidden gem of the immediate North Shore. Only a 30 minute commute via public transportation or car to downtown Boston. Winthrop is a lovely seaside community with lots of outdoor activities to enjoy. Walking distance to local food market and lots of terrific restaurants. Home to Robin's Nest, voted the North Shore's best gift shop! Governors Park is in the center of it all and is a very desirable place for renters and owners alike. This unit has been owned by the same family since 1986 and until recently, had the same tenant for over 10 years. The unit is being delivered vacant and "as is"...ready for someone to make a wise investment! With affordable upgrades it would make a great first home for someone looking to get into this beautiful town or a great opportunity to start or increase your existing rental property portfolio.

$829,900Est. Payment
5 Beds | 2 Baths | 2,471 Sqft

278 Winthrop Street, Winthrop, MA 02152

Multi Family For Sale

Winthrop by the Sea, just minutes to Boston. Well maintained 2 family in the heart of Winthrop. This sprawling 2 family sits on over 8000 square feet of land, featuring a 2 car garage and long drive way, with front and back yard space. Owners unit features generous sun bathed living room, open eat in kitchen perfect for entertaining, stainless steel appliances, dishwasher, and large separate pantry. Three bedrooms and separate sizable laundry room with space for a desk gives you all the space you need. Rental unit features 2 bed rooms large living room and separate dinning room. Both units feature a mix of Hardwood, tile, and laminate flooring. Explore the possibilities with unfinished attic in the 2nd floor unit. Come visit this lovely 2 family home in Winthrop by the Sea offering an easy commute to Boston by auto, the T, or water shuttle. Winthrop offers a golf club, boating, new schools, miles of beaches and great walking and bicycling routes. You don't want to miss this!!

$499,000Est. Payment
2 Beds | 2 Baths | 1,183 Sqft

67 Pleasant Street #1, Winthrop, MA 02152

Condominium For Sale

Enjoy the stress free living by the sea! TOTALLY BRAND NEW construction to newly renovated 2 bedroom 2 full bath with 2 exclusive use entries including beautiful private patio w/entry from living room. Hardwood flooring throughout, custom tiled baths, master bath w/double vanity, custom cabinets in kitchen and baths with quartz dining island and granite counters in kitchen and baths, high efficiency SS appliances and cozy electric fireplace, "Nest" thermostat, high efficiency on demand hot water and forced warm air with cent. A/C. The stacked washer & dryer are in the unit and there's ample closet space for bedrooms and extra storage. All the quaint town's amenities are within a stones throw to, restaurants, coffee and specialty shops, parks, walking trails, views of the Boston skyline, and resident public beaches. SHOWINGS to begin Monday Sept. 7, 2020

$569,900Est. Payment
3 Beds | 3 Baths | 1,826 Sqft

370 Revere Street, Winthrop, MA 02152

House For Sale

Step inside & immediately be whisked away to your own personal oasis! This well maintained 3 bedroom 2.5 bath colonial offers hard to find extra space along with majestic views of Short Beach Creek & the big city lights of Boston. First floor has a beamed ceiling dining room, a bright sunny kitchen with warm quartz counters & white custom cabinetry. Hardwood floors, crown moulding, & ductless AC are found in the large living room. The sunroom leads to a large new composite deck perfect for entertaining & over looking the spacious country like yard with stunning views. Finish off the day in the extended master with gorgeous sunsets from the inviting sitting area. Additional lower level space good for a family room & office, and a brand new full bath. A lifetime guaranteed interlocking roof & blown in insulation make this young home a smart choice. An easy commute or a beautiful background make this home a perfect fit for todays changing work style. Move right in and enjoy!

$519,000Est. Payment
3 Beds | 3 Baths | 1,788 Sqft

58 Banks St, Winthrop, MA 02152

House For Sale

Beautiful single family home with a finished basement. Two large bedrooms and washer and drier on second floor. Master bedroom includes a full bathroom as well. Third bedroom on first floor could also be used as an office or playroom. Large kitchen with a lot of natural light. Fenced in yard with a paved driveway that can easily fit 2 cars. Great walking paths just minutes away. Walking distance to the gym as well. Finished basement perfect for extended family living. Flood insurance required.

$690,000Est. Payment
6 Beds | 3 Baths | 2,191 Sqft

177 Pauline St, Winthrop, MA 02152

Multi Family For Sale

Prime location! This two family home is located close to the center of town, winthrop beach, and MBTA bus stop with easy access into Boston/Logan Airport. First floor unit consists of two bedrooms, open living room/dining room layout, newer galley kitchen and hardwood flooring throughout. Second floor unit consists of 4 bedrooms, two of which are located in finished attic space. Large master bedroom with two good size closets and hardwood flooring throughout. Washer/dryer hookup in basement. All utilities are separate. Shared driveway with parking for up to 4 cars. The perfect home for owner occupied or investor.

$725,000Est. Payment
4 Beds | 2 Baths | 2,016 Sqft

7 Paine Street, Winthrop, MA 02152

Multi Family For Sale

Winthrop by the Sea, just minutes to Boston! Well maintained ranch style 2 family offers single family living style with the benefit of income. Owner's unit has open floor plan with a 23 foot family room filled with natural light, new gas fireplace, picture window living room invites in the sunshine and a private screen porch for relaxation and outdoor enjoyment. Custom kitchen cabinets and granite counters, hardwood floors, central air, private work at home office and four car off street parking. Tucked away rental unit allows for owner's privacy and will generate good income to help with the mortgage. This is a easy maintenance two family. Come visit this inviting home in Winthrop by the Sea offering an easy commute to Boston by Auto, the T, or water shuttle. Winthrop offers a golf club, boating, new schools, miles of beaches and great walking and bicycling routes.

$295,000Est. Payment
2 Beds | 1 Bath | 780 Sqft

100 Governor'S Drive #16, Winthrop, MA 02152

Condominium For Sale

Governor's Park most sought after building. Very proudly maintained building. This unit is exceptional! All new and quite gorgeous quartz/stainless fully applianced kitchen, under the counter sink, new designer bath, all new quality oak floors, air conditioned, all freshly painted, walls and ceilings like new! balcony. This unit is only steps to the bus line to the T. Governor's Park is professionally managed, pool, and fitness center. Come visit Winthrop by the Sea! Only minutes to the great city of Boston. Beaches and boating abound! Golf course! New schools and great walking and biking paths.

$389,000Est. Payment
3 Beds | 1 Bath | 1,325 Sqft

26 Forrest Street 1, Winthrop, MA 02152

Condominium For Sale

Just steps to Winthrop Beach describes this 3 bedroom 1st floor condo which offers over 1300+ square feet of living in this 3 family home. Amenities include Three Chelsea tiled fireplaces with detailed mantles, a formal living and dining room, eat in kitchen with center isle and stainless steel appliances, pantry and laundry area right off the kitchen, Full bath with claw foot soaking tub, hardwood floors throughout home, two porches which include front enclosed and back porch which has shades for privacy. Pet friendly building, gas heat...Large Basement storage area...One car off-street parking....Condo fee includes flood insurance, water and master insurance. This won't last!!

$729,900Est. Payment
2 Beds | 3 Baths | 1,987 Sqft

1 Seal Harbor Rd #Ph3, Winthrop, MA 02152

Condominium For Sale

Welcome to Penthouse 3 at Seal Harbor 1. Here is your opportunity to own a slice of heaven. Unobstructed views from this magnificent unit consisting of nearly 2000 square feet of living space. Two levels of living, open concept main level to be designed and used as you choose. The are two bedrooms and 2 baths on the second level. It could be converted to 3 bedroom if someone wanted to. This Penthouse has the largest private outdoor space, close to 500 square feet, of all the units in this luxury complex. 2 Garage spots (A41 and A43) next to the main entrance. Stunning front lobby, 24 hour concierge, newly upgraded gym, outdoor in-ground pool, function room with kitchen, extra storage space and so much more. All this, for a fraction of what it would cost you to live in Boston. Open House by appointment on Sunday, 9/20 beginning at 12:00 and ending at 1:30. Call/Text for a time slot.

$450,000Est. Payment
3 Beds | 1 Bath | 1,562 Sqft

72 Harbor View Ave #3, Winthrop, MA 02152

Condominium For Sale

OPEN HOUSE SUNDAY 09/27 12:00-2:00. Soak up the sun and sea with this 3 bedroom, 1 bath, sun-drenched penthouse unit. Enclosed sun room with panoramic views of the ocean and harbor, as well as the gorgeous Boston skyline! Enjoy the Boston Harbor scenery, walk down to the local ferry service that brings you to the Seaport District, Aquarium, and Quincy's Marina Bay. This unit includes unique crown molding, original hardwood flooring throughout, french doors, and a large master bedroom with a large custom closet. If you're working from home at the moment, you can appreciate how important it is to have a serene space; this unit is all that and more! Come visit us for our open house this weekend and see for yourself!

version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >