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Winthrop MA Real Estate

Situated at the north entrance to Boston Harbor, Winthrop is an ocean-side city in the Greater Boston area. Winthrop is located on a peninsula in Suffolk County, offering beautiful views of the Atlantic ocean on the east and the Boston skyline on the west. Winthrop is a suburban community with residents who can enjoy the town’s several beaches and recreational areas. 

Homes For Sale in Winthrop, MA

Discover all real estate for sale in Winthrop, MA. Register to save your favorite Winthrop properties and receive notifications when new listings match your search criteria! Don't hesitate to contact us with any questions or to schedule a private showing.

27 Trident Avenue Winthrop MA 02152

MLS Number 73038576

  • MultiFamily
  • Bedrooms 12
  • Bathroom 3
  • Square Feet 4,254
  • Parking Spaces 6

A unique opportunity awaits with this large 3 family home in such a desirable investment location. The impressive 4 bedrooms and 1 bathroom spacious units are turn key ready with beautiful hardwood floors and an additional enclosed porch for each unit. All the hard work is done with a newer roof and newer furnaces, nothing needed but to start collecting rent in the growing Winthrop rental market. Parking isn't an issue with this property, each unit has the privilege of being assigned two off street parking spaces from the 6 spot paved driveway. Location is said to be where the value lies, and this location shows why. Leave your unit and walk minutes down the street and find yourself on the ocean front. Also enjoy the ability to travel anywhere with easy and quick access to public transportation and Logan International Airport. All this with a number of close by amenities. Currently bringing in a gross rental income of $8,000/mo with room for increase.

Listed by Jordan St. Fort of Divine Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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86 Bowdoin Street Winthrop MA 02152

Winthrop, MA86 Bowdoin Street

Price$1,100,000

Est. Mortgage: $/month

MLS Number 72956123

  • MultiFamily
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,200
  • Parking Spaces 6

YES, OPPORTUNITY KNOCKS!! UNIQUE PROPERTY, TWO SINGLE FAMILY HOMES ON ONE LOT........Great opportunity for Investors to condo or, for Buyers to owner occupy one while having an income from the other. It is also an option for family members to join forces and purchase together while living separately. Large lot and parking for 4+ cars. Both houses have 6 rooms and 3 bedrooms and 1.5 baths on 2 levels. The front house (#86) is very quaint and ready to call home having been freshly painted throughout with beautiful wood flooring, high ceilings, recessed lighting and a great layout.The house in the rear (#88) is contemporary and was completely remodeled 10 yrs. ago. It has an open floor plan, granite and stainless steel kitchen complete with farmer's sink and large island, recessed lighting and hardwood floors. WINTHROP by the SEA with 2 beaches, 3 Yacht Clubs, new schools, 9 hole golf course and Great Restaurants just minutes to Boston and Logan Airport!

Listed by Sharon Tallent and David Tallent of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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876 Shirley Street Winthrop MA 02152

MLS Number 73002099

  • Condo
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,000
  • Neighborhood Point Shirley

Direct Ocean Front Living. Feel like you're on Vacation everyday! This spacious 2 level, 7 room 4 bedroom 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day. Every day the view is different. Featuring Beautiful Dark Cherry hard wood floors, Family room, Formal dining room. (Living room or could be master bedroom) the Beautiful Kitchen, cherry cabinets, granite countertops, stainless appliances, both have sliders to the deck facing the sandy yard and beach. This is one of a kind and Direct ocean front living. All rooms are large with plenty of character. Walk in closets and Laundry room make this for easy living. Bus line to the Blue line and Water shuttle into Boston just a couple minutes away at the Landing next to Winthrop Yacht club. Marinas, shops and restaurants add to this great community. Don't miss this opportunity to live Directly on a Ocean!

Listed by James Iannuzzi of Boston City Properties

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3 Andrew Street Winthrop MA 02152

Winthrop, MA3 Andrew Street

Price$975,000

Est. Mortgage: $/month

MLS Number 73060465

  • Residential
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,662

WAITING FOR THE RIGHT ONE TO COME ALONG? THIS COULD BE THE ONE ON YOUR "WISH LIST" JUST IN TIME FOR THE HOLIDAYS........A hidden gem in Winthrop's Point Shirley, situated on Yirrell Beach. This large, 3 story oceanfront home has a huge open living room/dining combo with an inviting stone fireplace just perfect for family gatherings and entertaining. The second floor has 4 bedrooms and the top floor boasts an open suite/Great room with a living area and a sleeping area overlooking the ocean to one side and views of the harbor from the other......This home has lots of windows ( of course) and lots and lots of ocean! Large lot with yard and garden area too. THERE'S NOTHING BETTER THAN HAVING YOUR OWN SEASIDE ESCAPE! Next Open Houses Sat. & Sun. Dec.3 & 4 from 1-2:30.

Listed by Sharon Tallent and David Tallent of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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39 Cottage Park Road Winthrop MA 02152
Open House

MLS Number 73061784

  • MultiFamily
  • Next Open House: Sun 12/11 11:00 am. to 1:00 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2,795

Welcome to 39 Cottage Park Road. This sought after two family home is in great condition & in an even better location just minutes away from the heart of Winthrop Center. The first floor unit has a living room, dining room, one full bath, a small eat in kitchen, and two bedrooms. The second unit consists of two levels. On the first level, there is a living room, dining room, one full bath, a small eat in kitchen, and two bedrooms. On the second level there is another full bath, one bedroom, and a large open area that would be a great home office or den. All appliances in the units were replaced in 2014. The natural woodwork in the units is in mint condition. Separate gas heating systems. The home has three rear enclosed porches, full basement w/ plenty of storage and a 1/2 bath, and a recently paved driveway with tandem parking that accommodates three cars. The fenced in back yard is half grass and half stone patio - perfect for entertaining!

Listed by Meghan Santoro of Reference Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1001 Shirley Street Winthrop MA 02152

Winthrop, MA1001 Shirley Street

Price$899,900

Est. Mortgage: $/month

MLS Number 73034143

  • Land
  • Acreage 0.35
  • Zoning RES A

Rare opportunity to own oversized lot with brick building in Winthrop's Point Shirley. Point Shirley is a seaside neighborhood, reminiscent of Cape Cod, right here on Boston Harbor. Boston Harbor Island, historical Deer Island, offers walking and jogging trails along it's 2.6 mile perimeter, along with a fishing pier. Enjoy Winthrop's own Yirrell Beach, Coughlin Park, and Grand View Ave for swimming , water sports, and city views! The transit system has a bus stop right across the street which takes you to Orient Heights T Station. Close by Winthrop Landing offers seasonal ferry rides for commuters to The Aquarium and hot spot, Seaport District! SALE IS SUBJECT TO PARISH AND CANONICAL APPROVAL AND REMOVAL OF ALL RELIGIOUS ITEMS. SELLER WILL GO RIGHT TO P&S ONCE AN ACCEPTABLE OFFER IS AGREED UPON. A DECEMBER APPROVAL IS EXPECTED WITH A POSSIBLE JANUARY CLOSING.

Listed by Sheryl Howard of Cottage Hill Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1001 Shirley Street Winthrop MA 02152

Winthrop, MA1001 Shirley Street

Price$899,900

Est. Mortgage: $/month

MLS Number 73034142

  • MultiFamily
  • Bathroom 1
  • Square Feet 6,074
  • Parking Spaces 6
  • Property SubType Multi Family

Rare opportunity to own oversized lot with brick building in Winthrop's Point Shirley. Point Shirley is a seaside neighborhood, reminiscent of Cape Cod, right here on Boston Harbor. Boston Harbor Island, historical Deer Island, offers walking and jogging trails along it's 2.6 mile perimeter, along with a fishing pier. Enjoy Winthrop's own Yirrell Beach, Coughlin Park, and Grand View Ave for swimming , water sports, and city views! The transit system has a bus stop right across the street which takes you to Orient Heights T Station. Close by Winthrop Landing offers seasonal ferry rides for commuters to The Aquarium and hot spot, Seaport District! SALE IS SUBJECT TO PARISH AND CANONICAL APPROVAL AND REMOVAL OF ALL RELIGIOUS ITEMS. ALL OFFERS DUE NOON, SELLER WILL GO RIGHT TO P&S ONCE AN ACCEPTABLE OFFER IS AGREED UPON. A DECEMBER APPROVAL IS EXPECTED WITH A POSSIBLE JANUARY CLOSING.

Listed by Sheryl Howard of Cottage Hill Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1001 Shirley Street Winthrop MA 02152

Winthrop, MA1001 Shirley Street

Price$899,900

Est. Mortgage: $/month

MLS Number 73034137

  • Residential
  • Square Feet 6,074

Rare opportunity to own oversized lot with brick building in Winthrop's Point Shirley. Point Shirley is a seaside neighborhood, reminiscent of Cape Cod, right here on Boston Harbor. Boston Harbor Island, historical Deer Island, offers walking and jogging trails along it's 2.6 mile perimeter, along with a fishing pier. Enjoy Winthrop's own Yirrell Beach, Coughlin Park, and Grand View Ave for swimming , water sports, and city views! The transit system has a bus stop right across the street which takes you to Orient Heights T Station. Close by Winthrop Landing offers seasonal ferry rides for commuters to The Aquarium and hot spot, Seaport District! SALE IS SUBJECT TO PARISH AND CANONICAL APPROVAL AND REMOVAL OF ALL RELIGIOUS ITEMS. ALL OFFERS DUE NOON, SELLER WILL GO RIGHT TO P&S ONCE AN ACCEPTABLE OFFER IS AGREED UPON. A DECEMBER APPROVAL IS EXPECTED WITH A POSSIBLE JANUARY CLOSING.

Listed by Sheryl Howard of Cottage Hill Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

921 Shirley Street Winthrop MA 02152

MLS Number 73055711

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,786
  • High School Winthrop Sr. Hs

Welcome home to this beautiful seaside location. You will fall in love with this community full of shops, restaurants, cafes, 3 yacht clubs, and golf course. This single-family home boasts 3 bedrooms, with the option of a 4th on the 1st floor, Two floors featuring a full bath on each level, washer/dryer on main floor. Freshly painted interior, and sweeping views of the bay. You will feel serene in your sunflooded primary bedroom overlooking the bay. Enjoy stepping out of your kitchen onto a composite deck, with 40x90 private waterfront access. An additional deck, and if desired, rights to a dock or boat mooring. Don't miss this rare opportunity to own a waterfront property within close proximity to downtown Boston.

Listed by Christine Koutrobis of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

55 Banks Winthrop MA 02152
Open House

MLS Number 73057352

  • Condo
  • Next Open House: Sat 12/10 11:00 am. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,929

This brand new 3 bed 3 bath townhome is a ground-up rebuild with high end materials throughout. The exterior is Hardy plank siding in white with black windows for a modern look. The lofted ceilings and open floor plan give the home a spacious feel, and the closeness to the gym, local marinas, and Orient Heights Blue Line T Stop make it a great value compared to Boston condos. 2 townhomes are available, each with 2 car parking & private yards. Enter into the main floor and be greeted with an open floor plan and a gorgeous kitchen feauturing high end appliances & a two tone color kitchen, with an ocean slate colored island and white cabinetry. On the main floor there is a bedroom / office, and upstairs two large bedrooms with lofted ceilings, a full bath & owners suite. The lower level has a great sized room with tile finish, great for a play room, gym, or movie room.

Listed by The Reference Group and Seth Williams of Reference Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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116 Grovers Avenue Winthrop MA 02152

Winthrop, MA116 Grovers Avenue

Price$774,000

Est. Mortgage: $/month

MLS Number 73052545

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,306

PRICE REDUCED - MOTIVATED SELLER! Welcome to 116 Grovers Ave in beautiful Winthrop by the Sea. In this desirable highland's neighborhood, you will find this large 4-bedroom home with ocean views, beautiful natural light, and gleaming hardwood floors. The eat in kitchen with SS appliances opens to a large back yard to entertain guests, BBQ, garden and let the kids play. Off the kitchen you will find a formal dining room and 2 fireplaced living/family rooms. The second-floor features 4 generous bedrooms. OPPORTUNITY AWAITS as you are captivated by the views on the 3rd floor where you will find 3 additional semi-finished rooms. MAKE THIS YOUR DREAM HOME OR YOUR NEXT INVESTMENT PROJECT!

Listed by Rachel Gallant of Century 21 North East

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

65 Beacon Street Winthrop MA 02152

Winthrop, MA65 Beacon Street

Price$749,000

Est. Mortgage: $/month

MLS Number 73048222

  • MultiFamily
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,360

Nestled at the bottom of the desirable Water Tower area of Winthrop, this 2 family property would be a great buy for anyone looking to owner-occupy or invest, located next to the beach with a bus stop just at the end of the street for an easy access to Boston and Logan Airport.Here you will find two side by side units, with three levels of living space, with a half bath, living room and dining room on the first floor, a full bath and two bedrooms on the second and a third bedroom on the third floor. Great size yard and opportunity for parking.The most recent updates include GREE heat pumps installed in both units this year, the house insulated all throughout, triple pained windows and weather sealed doors makes it very energy efficient! Take advantage of the rental market and benefit from having tenants pay top dollar to be able to enjoy the beautiful ocean views with breathtaking sunrises, miles of beaches, 3 yacht clubs, 2 marinas, shops, golf course and fine restaurants of Winthrop.

Listed by Alla Rossi of Cameron Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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 or leasing 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 or leasing. MLSPIN 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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