Winthrop MA Homes for Sale

Winthrop, Massachusetts is a beautiful oceanside community 6 miles northeast of Boston. Winthrop features breathtaking views — on one side you have the panoramic view of the outer harbor and on the other is the Boston Skyline. Winthrop is a quaint New England town with plenty of parks, shops, inns, and beaches. Despite being a popular summer destination, Winthrop is a great place to call home regardless of the season.

Check out single family homes for sale in Winthrop, MA. Search through hundreds of listings to find the right real estate for you. Save your favorites when you register with us, and you can get email updates when similar properties that match your criteria are posted. Contact us for more information!

56 Otis Street Winthrop MA 02152
Active With Contract

MLS Number 72908884

  • Single Family Detached
  • Bathroom 1
  • Bedrooms 2
  • Rooms 5
  • Square Feet 1,105

Great curb appeal for this 2 bedroom, 1 bath Ranch style charmer of a home with finished basement situated perfectly between Yirrell Beach and the Harbor allowing for an easy life style. Enjoy a day at the beach, rinse off in your outdoor shower and spend the rest of the day on your deck or entertaining in your nice sized yard. The freshly painted interior and sun filled home has a pretty kitchen featuring granite counters, white cabinets and a tile back splash. The bath is modern and appealing. The finished basement, with recently added porcelain tile flooring and an EZ ventilation system, is spacious with a dedicated home gym area and could be used as a home office, play room or entertainment spot. Winthrop is a beautiful seaside community in close proximity to Boston.

Listed by Susan Doig of Charlesgate Realty Group,llc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

35 Girdlestone Road Winthrop MA 02152

Winthrop, MA35 Girdlestone Road

Price$649,000

Est. Mortgage: $/month

MLS Number 72907648

  • Single Family Detached
  • Bathroom 2
  • Rooms 8
  • Bedrooms 4
  • Lot Description Paved Drive

FIRST SHOWINGS WITH OPEN HOUSES SAT 10/16 & SUN 10/17, 11AM - 1PM. Located within easy walking distance to the beach, this lovely single family home offers lots of charm with upscale features. An enclosed porch off kitchen overlooks the very large backyard. Newly renovated, this house includes newest appliances, less than 1 year old! It is located in a highly desired neighborhood with convenient access to public transportation, parks, schools, and the many restaurants and shops Winthrop has to offer. This house is the perfect home for first time buyers looking for a clean and easy move in. This home features additional bonuses with a partially finished room in basement for more living space, as well as washer/dryer hook ups and plenty of storage in the basement.

Listed by Tyler Hall of Blue Ocean Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

79 Woodside Avenue Winthrop MA 02152

MLS Number 72907737

  • Single Family Detached
  • Bathroom 2
  • Rooms 6
  • Bedrooms 3
  • Acreage 0.09

Magnificently renovated single family home in a desirable part of Winthrop. First level has an open floor plan. Featuring large living room, dining room, completely redesigned kitchen with new cabinets, crown molding, granite counter tops, stainless steel appliances, recessed lighting and new hardwood floors throughout. We added a large full bath with laundry room. Second level has a small foyer at the top of the stairs. Three large bedrooms with ample closet space and large new full bath. Spacious backyard with new composite fence. Property has a new Azek front porch, back entrance and stairs. New roof, new driveway, new central heat and central air. New Rinnai tankless water heating system, all new electrical system throughout the home and updated plumbing. We have done all the work, just move in !

Listed by Joseph Young of Barsom Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

50 CLIFF Avenue Winthrop MA 02152

Winthrop, MA50 CLIFF Avenue

Price$849,900

Est. Mortgage: $/month

MLS Number 72904790

  • Single Family Detached
  • Bathroom 2
  • Rooms 8
  • Bedrooms 3
  • Acreage 0.17

CUSTOM BUILT MID-CENTURY MODERN 2 LEVEL RANCH, OVER-LOOKING THE OCEAN......ONLY ONE OWNER! Sweeping views of the Atlantic from the wall of windows in the open, dining room/living room combo. The top floor unit offers single family ranch-style living all on one level with an eat-in kitchen, large fireplaced living room and dining room for entertaining, 3 bedrooms and a full bath with laundry. The lower ( basement) level has a 3/4 bath, kitchen, and a large open space with another fireplace to offer a playroom/family room or extended living. Very pretty Highlands setting with a large lot and a very generous back yard, newer roof and 2 car off street parking. Great opportunity to make this home your own in Winthrop by the Sea.......Discover small town living just minutes to Boston with 2 beaches, 3 Yacht Clubs, new schools, a 9 hole Golf Course and lots of great restaurants!

Listed by Sharon Tallent and David Tallent of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

53 Prospect Avenue Winthrop MA 02152

Winthrop, MA53 Prospect Avenue

Price$749,900

Est. Mortgage: $/month

MLS Number 72901668

  • Single Family Detached
  • Bedrooms 3
  • Bathroom 3
  • Rooms 7
  • Square Feet 2,204

Welcome to 53 Prospect Ave, a 2,200+ square foot single-family home with 4+ parking spaces perched upon desirable Cottage Hill in Winthrop. No shortage of water views here - enjoy water views on both front and back of the property. Walk into an open concept dining/kitchen area perfect for entertaining guests. The kitchen features stainless steel appliances, a breakfast bar, and sliding doors for a direct walk out to the back yard and grilling patio. Oversized windows on both the second and third floor give every bedroom breathtaking views of the ocean and an abundance of natural light. With its wrap around porch, and classic Victorian styling, this home is impossible to miss. Just a short walk to the beach, Winthrop Yacht Club, and Winthrop Golf Course makes this already fantastic home that much more desirable.

Listed by Skambas Realty Group and Nicholas Murphy of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

10 Cottage Avenue Winthrop MA 02152

MLS Number 72898383

  • Single Family Detached
  • Bathroom 2
  • Rooms 6
  • Bedrooms 3
  • Acreage 0.13

Beachside living at its finest! This beautiful expanded Colonial is perched on Winthrop's Cottage Hill overlooking the Atlantic Ocean. As you enter the home, you are greeted with a spacious living room with a cozy fireplace and access to a sunroom with ocean views that can also be used as a home office. To your right, a dining room perfect for family dinners. Also on the main level, a charming kitchen with lovely original cabinetry, stainless steel appliances, and a bay window letting in lots of natural light. Upstairs, you will find a spacious primary bedroom with plenty of closet space. French doors in the bedroom open up to a stunning sunroom where you can enjoy morning sunrises over the ocean. Also on the second floor, you will find two good sized bedrooms and a full bathroom. This home is on a large corner lot featuring a fenced-in yard, various garden areas and a detached garage. Winthrop offers a serene, beachy lifestyle all just a couple miles from Downtown Boston.

Listed by Gui Moreira and The Hines Group of Berkshire Hathaway HomeServices Robert Paul Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

43 Seaview Avenue Winthrop MA 02152

Winthrop, MA43 Seaview Avenue

Price$639,000

Est. Mortgage: $/month

MLS Number 72893144

  • Single Family Detached
  • Bathroom 1
  • Rooms 7
  • Bedrooms 3
  • Acreage 0.15

This Fisherman Bend home offers large and open renovated eat-in kitchen featuring new granite countertops, stainless-steel appliances. Sea views, and natural light from the skylight, with added side office workspace. The formal living room has a working fireplace that leads to a den with a built-in corner cabinet. The 2nd floor offers 3 bedrooms, featuring an extra-large master with two extra-large -double closets, a built-in window bench, and an amazing “Seaview”. There is original 1900 hardwood floors throughout and an unrealized 3rd level, with plenty of storage. Featuring a cedar closet, the attic offers endless views with great potential for a writer's studio or teenager sanctuary. This Fisherman Bend home has pathway access through the expansive backyard to secluded Pico Beach. This home is easy commuting distance to Boston, and with many completed upgrades, it could be your own personalized seaside dream.

Listed by Grace Antunes of Keller Williams Realty Boston-Metro | Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

114 Pleasant Street Winthrop MA 02152

Winthrop, MA114 Pleasant Street

Price$849,000

Est. Mortgage: $/month

MLS Number 72888563

  • Single Family Detached
  • Bathroom 3
  • Rooms 11
  • Bedrooms 6
  • Acreage 0.16

One of a kind spacious historic single-family home in a lovely neighborhood. Maintained by generations of prudent live-in owners. This home features 2 car garage and full size basement along with 6 bedrooms and 2 1/2 bathrooms. 3rd floor comes with a separate bathroom which offers nice alternative to be used as living room and bedroom for your in-laws or family members. Entry foyer has original stainless glass windows and a one of a kind hardwood floor design. Working fireplace provides for special family dinners. Recently remodeled kitchen offers stainless stell appliances, granite tops and brand new custom made cabinets. Plenty of storage space, closets, hardwood flooring and original craft woodwork and eye-catching details throughout. The house features newer roof, newer composite decking / porches front and back, newly paved driveway and recently installed brick patios and walkway. Whether you like entertainment or prefer some quiet time this is a home for you.

Listed by Dalibor Konchar of Argos Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

39 Moore Street Winthrop MA 02152

Winthrop, MA39 Moore Street

Price$519,000

Est. Mortgage: $/month

MLS Number 72881879

  • Single Family Detached
  • Bathroom 2
  • Rooms 6
  • Bedrooms 3
  • Acreage 0.04

Great investment opportunity! The basement can be finished to add some extra living space as well as the attic providing beautiful ocean views! Steps to Winthrop Beach from this 3-4 bedroom home! Needs some remodeling, but has a ton of potential! Come make this home your own!

Listed by Jessica Pumphret of Blue Sky Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

143 Court Road Winthrop MA 02152

MLS Number 72877762

  • Single Family Detached
  • Village Cottage Park
  • Bathroom 3
  • Rooms 10
  • Bedrooms 5

WATERFRONT Living at it's FINEST! Oceanfront w/2 Boat Slips & DOCK! This Stunning Colonial Style Single Family Home boasts a First Floor Reception Area that leads to the spacious Living Room w/HW Floors, Beamed Ceiling & Electric Fireplace! Formal Dining Room w/Built-In China Cabinet, SS Fully Applianced Kitchen with Granite Counters, Ceramic Tile Flooring, Breakfast Bar & Recess Lighting! Beautiful BONUS ROOM w/Magestic Ocean Views & Sliders to Deck. Second Floor Features: 4 Bedrooms w/HW Flooring & Full Ceramic Tile Bath. Third Level: Over-Sized Master Bedroom Suite Ceiling Fan Duo. Garage, Alarm System, Sprinkler System, Lush Backyard w/HUGE DECK< Beach Area< Dock: Rare Find!!!! YOUR DREAM HOME AWAITS YOU minutes away from Boston!!!

Listed by Victoria Laws of Victoria Laws

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

993 Shirley Street Winthrop MA 02152

Winthrop, MA993 Shirley Street

Price$550,000

Est. Mortgage: $/month

MLS Number 72874129

  • Single Family Detached
  • Bathroom 3
  • Rooms 10
  • Bedrooms 4
  • Acreage 0.09

Winthrop's By The SEA Point Shirley... a community with in a community! This neighborhood offers Yirrell Beach, Coughlin Park, access to Deer Island walking path, and next to Winthrop Landing with Ferry service to Quincy and Boston. So much potential, this spacious home awaits your personal touches. Ten rooms and three bathrooms allows for a flexible living area. First floor offers den and family room or bedroom options(as seen in floor plans attached). Hardwood floors under carpet! The second floor offers water views of the beach.

Listed by Sheryl Howard of Cottage Hill Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

106 Washington Avenue Winthrop MA 02152

Winthrop, MA106 Washington Avenue

Price$699,000

Est. Mortgage: $/month

MLS Number 72874090

  • Single Family Detached
  • Bedrooms 4
  • Rooms 8
  • Bathroom 2
  • Acreage 0.11

Welcome to 106 Washington Ave built in 1761 this 4 bedroom center entrance colonial was once the residence of Winthrop sea captain and founding father George W. Tewksbury. The original and restored floor to ceiling brick fireplace in the dining room will become the centerpiece of your family & friend gatherings. Adorned with much original details such as, 4 original fireplaces, original wood floor, beautifully detailed coffered ceilings and built in casings. The rail and baluster staircase create the perfect reception. The front veranda is the perfect place for relaxation and reflection and offers some harbor views! The exterior of the home has a stunning slate looking interlock metal roof and the siding is all updated. There is a two car garage, plenty of parking, and rear deck overlooking a spacious yard. Newer gas furnace. An historic home with lots of yesteryear detail. Winthrop by the Sea, only minutes to Boston with so much to offer!

Listed by Christine D'Ambrosio of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

56 Beach Road Winthrop MA 02152

Winthrop, MA56 Beach Road

Price$499,900

Est. Mortgage: $/month

MLS Number 72865491

  • Single Family Detached
  • Bathroom 1
  • Rooms 7
  • Bedrooms 2
  • Acreage 0.07

Location! Location ! Location! Smell the sea air! Steps to the beach. First level features living room, dinning room, galley kitchen, full bath and laundry. One more room off the dinning room on this level, need a home office space? Two bedrooms on second level with large bonus area with storage, this space offers endless possibilities. Beautiful fenced in backyard, 2 car garage and driveway parking. Bring your vision and creative ideas for updating this home, as opportunity is knocking!

Listed by Diana Butler of Coldwell Banker Realty - Beverly

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

83 Lincoln Street Winthrop MA 02152

Winthrop, MA83 Lincoln Street

Price$549,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72862490

  • Single Family Detached
  • Bathroom 3
  • Bedrooms 3
  • Rooms 6
  • Acreage 0.11

A chance to own a piece of property in a fantastic Winthrop neighborhood. This spacious single-family property with an open floor plan, large bedrooms, and plenty of natural light has a ton of potential. On the first level, there is a kitchen, dining room, living room, family room, and one full bathroom. The second floor has 2 cozy bedrooms, a bathroom, and 1 master bedroom with another bathroom. Enjoy being minutes from Winthrop beach, and plenty of restaurants. With some TLC and creativity, this house has a chance to be a charming home.

Listed by The Ponte Group and Clifford A. Ponte of Keller Williams South Watuppa

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

36 Coral Avenue Winthrop MA 02152

Winthrop, MA36 Coral Avenue

Price$469,000

Est. Mortgage: $/month

MLS Number 72856365

  • Single Family Detached
  • Bathroom 2
  • Rooms 6
  • Bedrooms 3
  • Acreage 0.09

SELLER REDUCED!! STEPS TO THE BEACH!! This charming and partially demo'd property clears the way for your creative touches. Kitchen awaits your choice of cabinetry/appliances and flooring! Open and spacious fireplace living room has hardwood floors and coffered ceiling and opens into a front entry with Double doors to porch and views of the ocean. First floor set up for bathroom install. With 2 ample sized bedrooms and smaller 3rd bedroom on the second floor, front bedroom has beautiful ocean views and a door leading to the roof, where you can envision a rooftop balcony to soak up the gorgeous views and warm ocean breezes. This property is well worth the effort. If submitting offers, please sign and attach paper-clipped docs. See Firm Remarks. MASKS ARE REQUESTED TO ENTER.

Listed by The Apex Team of Apex Realty Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

89-R UPLAND Road Winthrop MA 02152

Winthrop, MA89-R UPLAND Road

Price$839,900

Est. Mortgage: $/month

MLS Number 72810741

  • Single Family Detached
  • Bathroom 1
  • Rooms 6
  • Bedrooms 3
  • Acreage 0.2

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. ***NO FLOOD INSURANCE NEEDED***

Listed by Sharon Tallent and David Tallent of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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. from third party sources, including sellers, lessors 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 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. 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.