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Winthrop MA Real Estate

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.

Homes For Sale in Winthrop MA

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. 

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799 Shirley Street Winthrop MA 02152

MLS Number 73085449

  • MultiFamily
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,115
  • Parking Spaces 4

Welcome to 799 Shirley Street, a stunning property in Winthrop where you can see the sunrise over the Atlantic Ocean and the sunset over Boston. For sale as either one multifamily with four parking spaces, or two separate condo units with two parking spaces each, this property allows for tremendous opportunity and versatility. Plus, there is a private detracted cabana in the back of the property located near the waterfront. Perfect for entertainers, art studio, music studio or more, this multifunctional space is a perfect for anyone. Unit 1 is a two bedroom, one bathroom home with a large front porch and a private deck off the main bedroom. Unit 2 is a three bedroom, two bathroom upper duplex with a renovated kitchen and private deck. Great location with proximity to the airport and downtown Boston!

Listed by Jamie Gaines and Joseph Castro of Columbus and Over Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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27 Trident Avenue Winthrop MA 02152

Winthrop, MA27 Trident Avenue

Price$1,250,000

Est. Mortgage: $/month

MLS Number 73070029

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

Calling all house hackers & investors! This 3-unit building is a proven money maker and offers an unbeatable location just steps from the beach!The entire property is very low-maintenance, with a newer roof, vinyl siding on the building and a small fenced-in front+side yard. The driveway has been paved & marked so that each unit has 2 designated off-street spots (vital this close to the shore).Inside, each 4-bed unit has a spacious eat-in kitchen & 1 full bathroom. The building still retains a lot of historical charm – from the beautiful hardwood floors to the bay windows & BONUS enclosed porches. Updated mechanicals include new boilers & new water heaters.What a location! The beach, schools, parks, restaurants & golfing are within walking distance, with easy access to the Blue Line T, the airport & downtown Boston.

Listed by Jordan St. Fort of Lion Gate Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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49 Siren Street Winthrop MA 02152

MLS Number 73082822

  • MultiFamily
  • Bedrooms 11
  • Bathroom 7
  • Square Feet 3,272
  • Parking Spaces 12

This 4-unit multifamily complex is being sold in conjunction with 49-R Siren as 1 property with a list price of $2,000,000. (MLS#73082822 and #73082825.) For the combined properties, there are 11 Bedrooms and 7 Bathrooms. In total, 49 Siren Avenue and 49-R Siren generate $162,600 per year in potential annual income. (See rent roll about specific rents.) Properties will be sold with residents remaining. Inspection is for informational purposes only. Properties are being sold “as is”.

Listed by John Young of Ledge & Young Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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29 Brewster Avenue Winthrop MA 02152

Winthrop, MA29 Brewster Avenue

Price$1,200,000

Est. Mortgage: $/month

MLS Number 73089023

  • MultiFamily
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,464
  • Parking Spaces 2

Welcome to 27-29 Brewster Ave, your dream beachfront home in a charming community just a stone's throw away from downtown Boston! This pristine two-family home boasts exceptional ocean views and a well-cared-for interior that's perfect for entertaining.With two-car parking and rental income potential, this property is an excellent investment opportunity. The stunning bi-level unit with a massive upper-level deck that's perfect for enjoying the gorgeous colors of sunsets and sunrises over the ocean, has three bedrooms two bathrooms and a bonus room. The second unit is a cozy newly updated studio layout with a private entrance and one bathroom.Boating enthusiasts will love the nearby marinas, and foodies will appreciate the fabulous restaurants in the area. Whether you're looking for a peaceful retreat or a lively community, this home has it all. Don't miss your chance to make the dream of beachfront and the s living yours, ask about available finance options.

Listed by Nicole Bettano and Robert Murphy of Lantern Residential

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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 73079434

  • 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 has cherry cabinets, granite countertops, stainless appliances, sliders to the large 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 Blue line and Water shuttle into Boston is 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 the Ocean!

Listed by James Iannuzzi of Boston City Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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180 Winthrop Street Winthrop MA 02152

Winthrop, MA180 Winthrop Street

Price$999,900

Est. Mortgage: $/month

MLS Number 73089308

  • MultiFamily
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,000
  • Parking Spaces 6

3,000+or- Square feet of Living Space. 1st floor level has a modern kitchen granite counter tops with dishwasher, huge living room/Dining room Combo. with 1 bedroom master bath with 3/4 bath, 2 wall A/C's one in master bedroom and one in the living room/dining room combo. 2nd floor unit has a Modern kitchen another large living room/dining room Combo, Full Bath and 3 bedrooms, Hardwood floor in a lot area's. Mostly newer windows there maybe one or two that wasn't done. 6 car parking. Front Porch and rear Decks. Slate Roof. This is a single that easily made into a 2 family. Seller already started the process has a the Variance In Hand. 200 amp CB . About 5 year old heating system. Commercial Zoned Location. Could possibly put office on the First Floor and rent out the second Floor. Attached Plot Plan that shows parking, you can get more parking. Also Fisrt and second floor layout. Business District

Listed by Phil Consolo of Century 21 North East

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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

180 Winthrop Street Winthrop MA 02152

Winthrop, MA180 Winthrop Street

Price$999,900

Est. Mortgage: $/month

MLS Number 73089188

  • Residential
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,000

3,000+or- Square feet of Living Space's already started the process, has a the Variance in hand for a 2 Family. 1st floor 4 rooms 1 bed has a modern kitchen, granite counter tops with dishwasher, huge living room/Dining room Combo. with 1 bedroom master bath with 3/4 bath, 2 wall A/C's one in master bedroom and one in the living room/dining room combo. 2nd floor unit has a Modern kitchen another large living room/dining room Combo, Full Bath and 3 bedrooms, Hardwood floor in a lot area's. Mostly newer windows there maybe one or two that wasn't done. 6 car parking. Front Porch and rear decks. This is a single that easily made into a 2 family. 200 amp CB . About 5 year old heating system. Slate Roof. Commercial Zoned Location. Could possibly put office on the First Floor and rent out the second Floor. Attached Plot Plan that shows parking, you can get more parking. Also First and second floor layout. Business District

Listed by Phil Consolo of Century 21 North East

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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

172 Cliff Avenue Winthrop MA 02152

MLS Number 73087603

  • Residential
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3,200
  • High School Middle/High

Welcome to 172 Cliff Avenue here in the Winthrop Highlands. Constructed in 2008, this young townhome is located on the historic site of the famed Cliff House. Spectacular ocean views can be seen from nearly every floor and every room, and south-facing picture windows create a naturally sunny space. Hardwood floors, stainless steel GE Profile appliances, built-in surround-sound, central vac, and central heat and a/c check all of the boxes. This property lives just like a single family home, without the concerns of exterior maintenance. A rare find in Winthrop, two attached garage parking space and a huge driveway offer ample parking for residents and guests. Overlooking Winthrop Beach, the unobstructed views from this home truly cannot be missed. For those unfamiliar, Winthrop a lovely beach community located 2 miles due east from Downtown Boston. One of Greater Boston's last "small town" communities, we enjoy both proximity to the City, and the peace that comes with small town living.

Listed by Stephen Hines of Lantern Residential

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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

144 Main Street Winthrop MA 02152

MLS Number 73091486

  • MultiFamily
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,988
  • Parking Spaces 6

Turn of the century multi family home with lovely formal entry and many period details. The Home consist of three levels plus basement, separate driveways on large lot of land. The rear of the yard has new retaining wall . There have been many updates including large modern eat-in kitchen, gleaming hardwood floors. Owner's unit presently has four bedrooms on two levels with additional unfinished room for more. During ownership heat, hot water, electric, kitchens and baths have been updated : There is storage shed in pool size yard. Conveniently located shopping to parks,schools,and public transportation.

Listed by Janice Stevens of Century 21 Seaport

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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

49 R Siren Winthrop MA 02152

MLS Number 73082825

  • MultiFamily
  • Bedrooms 11
  • Bathroom 7
  • Square Feet 2,970
  • Parking Spaces 6

This 3-unit multifamily complex is being sold in conjunction with 49 Siren Street as 1 property with a list price of $2,000,000. (MLS #73082822 and #73082825.). For the combined properties there are 11 Bedrooms and 7 Bathrooms. In total 49 Siren Avenue and 49-R Siren generate $162,600 per year in annual income. (See rent roll about specific rents.) Properties will be sold with residents remaining. Inspection is for informational purposes only. Properties are being sold “as is”.

Listed by John Young of Ledge & Young Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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

799 Shirley Street Winthrop MA 02152

MLS Number 73085436

  • Condo
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,100
  • Neighborhood Point Shirley

Here it’s all about the views. From this spacious upper duplex you can see water from almost every window in the home. Perfect for entertaining or escaping the hustle & bustle of the city, the spacious living room has an attached sunroom with 8 windows that will make you fall in love with this place. Off of the living room is a dining room flowing into the newly renovated kitchen with all new stainless steel appliances, laundry, a pantry and a breakfast nook. On the main level you will find one bedroom and one bathroom. Ascend to the second level where you will find two more large bedrooms and another full bathroom. This home and flow is perfect for every lifestyle!

Listed by Jamie Gaines and Joseph Castro of Columbus and Over Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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

124 Terrace Avenue Winthrop MA 02152

MLS Number 73085700

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,866
  • High School Whs

Sweeping vista views from this home perched high upon Winthrop's Cottage Hill - from the Atlantic Ocean to Downtown Boston. Spectacular location overlooking Yirrel Beach and Winthrop Harbor. Located on a dead-end street, this single family home needs TLC, but is move-in ready and offers plenty of room for your own personal touches. Incredible potential - Unfinished attic and lower level, great outdoor space off to the side and terraced in the back of the property. Just steps to the beach, close to restaurants, shops and the Winthrop Yacht Club - minutes to Downtown Boston via water ferry or public transportation. Properties in this location are not available often and this home offers you an opportunity to create a perfect oceanside retreat. Easy to show.

Listed by Edward Deveau of Century 21 Mario Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.42% last updated on Mar 16, 2023
* 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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bench facing harbor with moored boats

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