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Winthrop Single-Family Homes

The homes for sale in Winthrop MA offer a wide variety of architecture, elegance and quality crafted detail. They date back to the late 1800’s and as recently as 2010. The homes for sale in Winthrop MA are late 1800 Queen Anne Victorians, Colonial Revivals, Greek Revivals, Italianates, Gothic Revivals, Ranches, Colonials and luxury high rise ocean front condominiums. With Winthrop's majestic ocean and Boston harbor and skyline views and its great convenience to Boston, the homes of Winthrop offer incredible value. LIFE IS BETTER IN WINTHROP BY THE SEA!

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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.

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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: 3.09% last updated on Oct 21, 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.

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42 Moore Street Winthrop MA 02152

MLS Number 72913073

  • Single Family Detached
  • Rooms 8
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.06

Welcome to 42 Moore St! Walk through your front door into your open floor plan with gleaming hardwood floors, an updated kitchen with stainless steel appliances, dining area, and in-ceiling speakers for your entertainment. Every nook of this house has the perfect decor and upgrades. The 3-zone heating system has Nest thermostats on each level, perfect for cranking the heat remotely before you get home from a hard day's work, or while lounging in your living room. Head upstairs where you'll find the most perfect primary bedroom with a large walk-in closet and stunning en suite featuring dual vanities and an oversized shower with rain heads. The second bedroom on this level has been converted into the perfect dressing room, but could easily be used a bedroom once again, or a nursery / kid's bedroom. On the third floor you'll find two more graciously sized bedrooms, perfect for kids or guests. The basement is clean & dry, currently set up for additional storage / a home gym.

Listed by The Reference Group and Seth Williams of Ledge & Young Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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.

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50 CLIFF Avenue Winthrop MA 02152

Winthrop, MA50 CLIFF Avenue

Price$799,900

Est. Mortgage: $/month

Open House

MLS Number 72904790

  • Single Family Detached
  • Next Open House: Sun 10/31 11:00 am. to 12:00 pm.
  • Bathroom 2
  • Bedrooms 3
  • Rooms 8

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: 3.09% last updated on Oct 21, 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.

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290 Bowdoin Street Winthrop MA 02152

Winthrop, MA290 Bowdoin Street

Price$779,000

Est. Mortgage: $/month

MLS Number 72880363

  • Single Family Detached
  • Bedrooms 4
  • Bathroom 3
  • Rooms 7
  • Acreage 0.14

Back On Market buyers financing fell through!! This home has a been carefully renovated to mix modern updates while keeping the original beautiful details it originally was built with. Beautifully painted exterior sits on a corner lot with a wrap around porch. New kitchen with tile backsplash and quartz countertop and tile floor. 3 full baths all beautifully renovated with tiled showers and tiled floors. Interior features include hardwood floors throughout. Beautifully detailed working fireplace, detailed staircase, period stainless windows, central AC, and original hardwood floors. Finished basement with walkout to back yard. Laundry room on second floor with 3 bedrooms. Enjoy your master suite on the 3rd floor with full bath and large closet. Nice size fenced in yard with garage and off street parking. This home is close to many amenities that Winthrop has to offer. Walk to the bus stop, Winthrop center, restaurants and many local beaches.

Listed by Elizabeth Ferrara of Cottage Hill Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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.

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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
  • Acreage 0.12

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: 3.09% last updated on Oct 21, 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.

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175 Main Street Winthrop MA 02152

Winthrop, MA175 Main Street

Price$749,000

Est. Mortgage: $/month

Open House

MLS Number 72910635

  • Single Family Detached
  • Next Open House: Sun 10/31 12:00 pm. to 1:30 pm.
  • Rooms 8
  • Bathroom 2
  • Bedrooms 3

Rare extra large corner lot with multi vehicle off street parking. Interior has modern feel with multiple upgrades and a dream kitchen. Three bedrooms up with two additional rooms that can be used as office, workout or dressing room. Hardwoods throughout. Enclosed sun porch and deck off kitchen. This home has so many extras. Dont miss this one.

Listed by Janice Stevens of Century 21 Seaport

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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.

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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: 3.09% last updated on Oct 21, 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.

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10 Cottage Avenue Winthrop MA 02152

MLS Number 72898383

  • Single Family Detached
  • Bedrooms 3
  • Rooms 6
  • Bathroom 2
  • 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: 3.09% last updated on Oct 21, 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.

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106 Washington Avenue Winthrop MA 02152

Winthrop, MA106 Washington Avenue

Price$650,000

Est. Mortgage: $/month

MLS Number 72874090

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

Welcome to 106 Washington Ave built in 1761 this 4 bedroom FEDERAL STYLE 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: 3.09% last updated on Oct 21, 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