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!

251 Court Road, Winthrop, MA

Price$1,545,000

Est. Mortgage: $/month

MLS Number 72329997

  • Single Family
  • Parking Spaces 3
  • Year Built 1930
  • Full Bath 1
  • Bathroom 2

Ocean front property located on Winthrop's most sought-after street! This brick single family offers unobstructed views of the ocean. This property has so much potential. Your own private pier is obtainable with this home. Winthrop by the sea offers a private golf course, beaches, yacht clubs, and multiple new restaurants and shops. It's home to a new middle and high school along with a brand new track and field. Boston is accessible by MBTA buses and our very own water ferry! This home requires extensive renovations but the location and view are priceless. This is a 9000+ sqft Lot and the water views are spectacular.

Listed by Mark Sciaraffa of Century 21 Seaport

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

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$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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153 Court Road, Winthrop, MA

Price$975,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72324156

  • Single Family
  • Parking Spaces 3
  • Village The Maze
  • Year Built 1908
  • Full Bath 2

This distinguished waterfront home features a rare level of craftsmanship and materials, stunning views of Boston Harbor and the City skyline, your own private dock, and a delightful seaside lifestyle. Imagine...just minutes from Boston, you can grab your kayak for a sunset paddle and grill on the deck while drinking in a spectacular sunset and tranquil water views. Who knew?! This Queen Anne masterpiece is set in Winthrop's premier neighborhood, The Maze. Built in the glorious era of the early 20th-century, it exemplifies the grace and high standards of the day. Masterful architectural details abound - carved newels and balustrades, delightful window details, stained glass, glowing fir floors. Handicapped access features and entry ramp may be helpful to some buyers. Outside, mature trees and dappled sunshine grace this oversized quarter-acre fenced lot. The property has riparian rights and steps down to its private waterfront beach. Enjoy easy access to public transport to Boston.

Listed by Brianne Grady of Robert Paul Properties

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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156 Sewall Avenue, Winthrop, MA

Price$970,000

Est. Mortgage: $/month

MLS Number 72313847

  • Single Family
  • Parking Spaces 4
  • Village Highlands
  • Year Built 1962
  • Full Bath 3

Fabulous ocean views from all of the rooms on the first floor; vaulted ceilings provide an open and spacious feel flowing from fireplaced living room to updated kitchen and dining area to cathedral ceiling family room overlooking private yard. Three bedrooms on the second floor with beautiful hardwood floors, two have ocean views, and an updated bath. The third level, added in 2000, features a master suite with fireplaced sitting area, full bath, fabulous walk in closet and additional room for a home office or family room. A four room inlaw suite on the lower level is perfect for college students, au pair or visitors. With lots of space and separate living areas, this ocean view home would be perfect for a multigenerational family. Great location just across from neighborhood beach with access for swimming, kayaking or sunset watching.

Listed by Pat Sullivan of Century 21 Seaport

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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71 Winthrop Street, Winthrop, MA

Price$829,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72365199

  • Single Family
  • Parking Spaces 3
  • Year Built 1970
  • Full Bath 3
  • Bathroom 3

Modern design at its finest! This recently renovated, beautiful home has a strong foundation with a new 2nd and 3rd floor added in 2016. Easily flow from one room to the next in the renovated, open first floor layout, that is ideal for family entertaining and enjoyment. The double sided stair-case leads to a masterfully designed second floor with 3 large bedrooms, each with its own walk-in closet. With extra-large windows throughout the home it creates a light and warm haven even in the cold New England winters. Laundry is a breeze, as its centrally located on the second floor. Hardwood floors throughout. Custom built-in window seats provide a perfect escape for reading the paper or catching up on the latest best seller. Prefer to be out doors? A stamped concrete walk-way connects two large patios with enough green space on either side of the house for the dog and kids to run around. Powered by solar panels, you will never have to pay an electrical bill ever again! This is a must see!

Listed by Michael Eruzione of Robert Paul Properties

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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 Sargent, Winthrop, MA
Open House

MLS Number 72380184

  • Single Family
  • Next Open House: Sat 18th 11:00 am - 1:00 pm
  • Parking Spaces 5
  • Year Built 1900
  • Full Bath 2

Saturday 8/18/18 Open House 11:00-1:00. Come see this beautifully maintain English Cape featuring gleaming hardwood floors throughout.Walking distant to cottage Park yacht club. Stainless steel appliance kitchen with granite counters.Main house boasts 4 bedroom. Bonus In law 1 bedroom Legal apartment in finished basement. Meticulously maintained yard to entertain in. Newer roof and heating system for peace of mind.

Listed by Donald May of Copperwood Real Estate, Inc.

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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550 Pleasant Street, Winthrop, MA

Price$699,000

Est. Mortgage: $/month

MLS Number 72372686

  • Single Family
  • Year Built 2007
  • Full Bath 2
  • Bathroom 2
  • Bedrooms 2

Exceptional quality & smart design define this 2 bedroom, 2 bathroom located on the Harbor's edge commanding unsurpassed, panoramic views overlooking the City skyline. A corner exposure, w/lots of windows create an open, Great Room with several distinctive living areas. The open kitchen, w/walk-in pantry extends into an 8-foot wet bar complete w/sub-zero beverage center & radiant heat, Italian tile flooring. With nearly 2,000 s.f. & two garage parking spaces within walking distance to the Yacht Club & Restaurants, this special offering is a fantastic, maintenance free single family alternative. Enjoy breath-taking sunsets year-round on your oversized balcony. Or, on chillier evenings beside the signature, ice quartz gas fireplace with a mantle fashioned in re-claimed wood. The en-suite master bath invites. Boasting a soaking tub, glass walled shower & river stone wall accents. An easy commute to the heart of Boston via ferry ride or MBTA & home to the many beaches & sea breezes.

Listed by Karen Peters of Douglas Elliman Real Estate

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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146 Grand View Avenue, Winthrop, MA

Price$698,000

Est. Mortgage: $/month

MLS Number 72342781

  • Single Family
  • Parking Spaces 2
  • Year Built 1927
  • Full Bath 2
  • Bathroom 2

ABSOLUTELY STUNNING VIEWS OF BOSTON HARBOR WITH THIS RENOVATED WATERFRONT BUNGALOW - Wake up every morning to the extraordinary and ever-changing panorama of Boston Harbor and the skyline of the city, as you enjoy your coffee on the extraordinary front porch of this Point Shirley gem. Truly incredible and expansive vistas await you in this highly sought-after location. While you will be mesmerized by the incredible views, you will be amazed at the bright,sunny and open concept interior of the quaint environs. Complete down-to-studs renovation include hardwood floors throughout, new mechanical systems, brand new roof, large kitchen with island, central AC, handicap accessible, two full baths and all on one level. This property is enhanced with direct water access, dock rights, a rare two car garage, full basement for your workshop or additional storage area and rear deck overlooking a well groomed yard. Don't miss out on this once-in-a-lifetime opportunity!

Listed by Kevin Lawless of Stone Ridge Properties, Inc.

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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24 Orlando Avenue, Winthrop, MA

Price$689,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72375031

  • Single Family
  • Parking Spaces 3
  • Year Built 1937
  • Full Bath 1
  • Bathroom 2

Winthrop's most sought after neighborhood, Cottage Park! Only steps to the Cottage Park Yacht Club! Pride of ownership shines through in this meticulously maintained 3 plus bedroom, 1.5 bath Colonial. It's truly in move in condition and affords an easy, care fee life style with spacious and modern quartz/stainless kitchen, all open bright floor plan, golden wood floors, inviting fireplaced living room that leads to a charming 3 season ship lap cathedral ceiling sun room that leads to a sprawling deck overlooking a large yard. The dining room offers impressive wood crafted built ins with a large picture window that invites in the outdoors and there is a half bath on the first floor. The sparkling freshly painted second floor offers three good size bedrooms, new designer tile bath and a fourth bedroom or nursery off the master bedroom. This homes offers a real barn with loft, a separate workshop, new roof and heating system. This is a VERY SPECIAL HOME!

Listed by Jonathan Polino of Highland Real Estate

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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24 Maryland Avenue, Winthrop, MA

Price$674,900

Est. Mortgage: $/month

MLS Number 72354969

  • Single Family
  • Parking Spaces 2
  • Year Built 1950
  • Full Bath 2
  • Bathroom 2

***MILLION Dollars views for $674,900??? This amazing brick offers you an open floor plan with panoramic ocean views. Enjoy the breathtaking views of the Boston skyline from the eat in kitchen. Sit in your backyard, patio, or private beach and enjoy the sunset and cool ocean breeze as the sailboats drift by. A once in a lifetime opportunity to create your own oceanfront paradise. Just minutes from Boston, multiple yacht clubs, golf course, and a some of Winthrop's best restaurants. This can be your dream home, one of a KIND***Property needs some updating, brand new heating systems, two car garage with a deck on the top of the garage, lot next to the house is for sale, can be sold as a package. DOCK RIGHTS,BEACH RIGHTS. Seller is fixing the Sea Wall. Property is Lot D as shown in the map.

Listed by Simone Schettino of Century 21 North East

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Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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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156 LOCUST Street, Winthrop, MA

Price$650,000

Est. Mortgage: $/month

MLS Number 72266326

  • Single Family
  • Parking Spaces 3
  • Year Built 1870
  • Full Bath 3
  • Bathroom 3

SEASIDE LIVING CAN BE YOURS, A MUST SEE TO APPRECIATE ALL IT HAS TO OFFER.........This very spacious, Contemporary four plus bedroom home was completely remodeled in 2002 and has 2 gas heating systems and offers central A/C. Great first floor layout for entertaining with a gas fireplaced living room, a full bath, dining room open to the kitchen, sliders to a large deck and private rear yard and off street parking for 3 cars. The second floor offers large bedrooms, a full bath and a master suite with a cathedral ceiling, master bath with jacuzzi tub and seperate shower. Top floor deck with spectacular ocean views........Life is better in Winthrop by the Sea!. Discover and enjoy small town living only minutes to the great city of Boston !!!

Listed by Sharon Tallent and Virginia Brown of Highland Real Estate

{$office->Name}

Highland Real Estate
75 Crest Avenue
Winthrop MA, 02152
Office: (617) 846-8000

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.53% last updated on Aug 16, 2018
* 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 A VisitAsk A QuestionMore Details