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!

9 Marshall Street Winthrop MA 02152
Open House

MLS Number 72749953

  • Single Family Detached
  • Next Open House: Fri 10/30 5:00 pm. to 6:30 pm.
  • Village Ingleside
  • Bathroom 4
  • Rooms 8

Just Move In to this Sun Filled Renovated 4 plus bedroom 3 and Half Bath Home!, Plenty of space for the whole family and the work has been done within the last three years! UPDATED KITCHEN with tall cabinets, granite counter tops, new appliances and CENTER ISLAND with sink, Open concept Living and Dining Room, Hardwood Flooring, Recessed Lighting, Central AC. Lovely Front and Dining Room Bay Windows bring in more light. 1ST FLOOR MASTER with sliders to updated 17*17 deck overlooking Fenced in Yard, Beautiful MASTER BATH with Double Sinks, and quiet sitting/dressing or office area. Main Level also Half Bath and Laundry Area, 2nd Level with 3 bedrooms, Full Updated Tile Bath with Double Sink vanity as well as common Den or Sitting Area. FINISHED BASEMENT, 2 rooms, plank flooring, plenty of lighting w Recessed Lights and Bathroom w Tiled Shower, Great for extended Family. Walk to Ingleside Park, Close to Winthrop Center. Ez access to T. Minutes to Beaches, Boston and Logan Airport.

Listed by Tanya Palmer of Palmer Properties & Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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 Pleasant Park Road Winthrop MA 02152

Winthrop, MA50 Pleasant Park Road

Price$629,900

Est. Mortgage: $/month

Open House

MLS Number 72749271

  • Single Family Detached
  • Next Open House: Fri 10/30 4:30 pm. to 6:00 pm.
  • Bathroom 1
  • Rooms 7
  • Bedrooms 4

Come fall in love with this beautifully maintained waterfront colonial situated on a sizable corner lot overlooking Belle Isle Marsh. This move in ready property boasts 4 bedrooms, open concept living/ dining room , eat-in kitchen with stainless steel appliances and partially finished basement adding additional living space. Enjoy your morning coffee while watching the sunrise from one of the many oversize picture windows. Entertain on the large back deck while the sunset casts a serene golden glow. This home features eye catching hardwood floors throughout. Laundry is conveniently located off the kitchen. off street parking for 3 cars, ample storage in the walk in attic that includes floor plans to convert to master bath. Recent updates include: electrical, plumbing, new roof, water heater and much more. Too many updates to list. Come see for yourself what pride of ownership looks like.

Listed by Danielle Dichiara of United Brokers

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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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9 Woodside Park Winthrop MA 02152
Open House

MLS Number 72748625

  • Single Family Detached
  • Next Open House: Sat 10/31 11:00 am. to 1:00 pm.
  • Bathroom 3
  • Rooms 12
  • Bedrooms 3

Location Location Location! One of Winthrop's most desirable neighborhoods! Come check out this one of a kind single family located at a dead end street in a private park setting. As you enter this charming home with beautiful original details throughout, you will be greeted by a warm & welcoming wood burning fireplace in the foyer. The 1st floor offers a large living room, kitchen, dining room, half bath and additional office. The 2nd floor offers 3 bedrooms, a full bath and an enclosed sun porch with amazing water views! Finished basement features a second full bathroom and additional living space! Large fenced backyard with a salt-water inground pool, perfect for entertaining family and friends. Only one house from the water and beach! Nothing quite like it in all of Winthrop! Must see to appreciate.

Listed by Paul Travaglini of Century 21 Seaport

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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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282 Pleasant Street Winthrop MA 02152

Winthrop, MA282 Pleasant Street

Price$685,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72746554

  • Single Family Detached
  • Bathroom 2
  • Rooms 7
  • Bedrooms 4
  • Square Feet 2,293

Own a Piece of Winthrop's History-282 Pleasant Street is constructed on an oversized 6280 SF lot by the prominent John Sturgis Tewksbury family in the mid 1800s. Being only 1 of 8 Italianate Mansard-roofed homes with classic dormer windowing, particular attention has been devoted to restoration of Dentil molding and installation of copper ridging. Clapboard siding along with 6' decorative fencing makes for an attractive and privacy-enhanced setting. Hardwood flooring throughout. First level presents a 12x24' room that may be utilized as a bedroom, family room or remote work space with 3 bedrooms on upper level. Eat-in kitchen, dining area, full bath and elongated living room complete lower floor. Open the master bedroom door to a most welcome feature: an 488 SF roof deck that is perfect for a quite coffee and newspaper respite or congenial gatherings. Recently-installed, highly-efficient Viessman heating system and water heater. Photos of Tewksbury & farm circa 1885 attached.

Listed by Marilyn Jones and D and S Group of Century 21 North East

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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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174 Cliff Avenue Winthrop MA 02152

Winthrop, MA174 Cliff Avenue

Price$840,000

Est. Mortgage: $/month

Open House

MLS Number 72748036

  • Single Family Attached
  • Next Open House: Sun 11/1 11:00 am. to 12:00 pm.
  • Bathroom 4
  • Rooms 7
  • Bedrooms 4

PRIVATE, EXCLUSIVE, WATER VIEWS! Welcome to 174 Cliff Avenue, a pristine townhome that feels like single family living with breathtaking views of Winthrop beach & Winthrop's water tower! 1st floor is an open floor plan with living room, dining area, built-in bar area with wine refrigerator. Kitchen with updated Bosch appliances & GE refrigerator. Formal dining room w wainscoting and chair rail, pocket doors & up-lit crown moulding. Half bath w stackable LG washer/dryer complete the 1st floor. 2nd floor has large master bedroom with beautiful ocean views, sitting area, 2 custom closets with built-ins, large master bath with stand up shower with body sprays. 2 good size bedrooms & a full bath complete the 2nd floor. 3rd floor has 2 skylights is currently being used as game/rec room but could be used as 4th bedroom. Fully finished basement with office, sitting area, workshop, half bath & attached 2 car garage with additional workshop area. Large back yard! Welcome to your dream home!

Listed by Christine D'Ambrosio of Compass

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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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168 Brookfield Road Winthrop MA 02152

Winthrop, MA168 Brookfield Road

Price$725,000

Est. Mortgage: $/month

MLS Number 72741082

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 3
  • Square Feet 1,800

Welcome Home to 168 Brookfield Road. Wonderful curb appeal, corner lot, overlooking Ingleside Park. Meticulously maintained 8 room, 3 bedroom, 2.5 bath. First floor offers open floor concept. This home was fully renovated 18+- years ago. Roof is approximately 8-9 years old. Lower level has a 15X15 (approx) room with 3/4 bath. Seven zone irrigation system, shed, 3 Zone Heating and so much more.

Listed by The Suffolk Group and Mary Curran of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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74 Cross Street Winthrop MA 02152

Winthrop, MA74 Cross Street

Price$499,000

Est. Mortgage: $/month

MLS Number 72739628

  • Single Family Detached
  • Bathroom 1
  • Rooms 6
  • Bedrooms 3
  • Square Feet 1,122

This charming Dutch Gambrel not only is centrally located to everything - shopping, public transportation, parks and beaches - but it boasts 3 bedrooms, a 3-season porch, hardwood flooring throughout, lots of natural light and a private back yard. The main living area offers an open floor plan with an updated kitchen featuring granite countertops, stainless steel appliances, recessed lighting a large kitchen island and formal dining area and spacious living room. A great layout for entertaining! Enjoy the crisp fall mornings while drinking coffee on your Trex deck overlooking the large back yard. Do not miss the opportunity to make this house your home!

Listed by Alexander Montalto of Lamacchia Realty, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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18 AMELIA Avenue Winthrop MA 02152

Winthrop, MA18 AMELIA Avenue

Price$779,900

Est. Mortgage: $/month

MLS Number 72736813

  • Single Family Detached
  • Bathroom 3
  • Rooms 10
  • Bedrooms 4
  • Square Feet 2,084

THIS EXCITING, CUSTOM BUILT MULIT LEVEL MID-CENTURY MODERN GEM AWAITS! This unique architectural classic was proudly built in 1958, owned, maintained and happily lived in by a Winthrop developer and his family.From the moment you walk in, you will be amazed by the timeless and unspoiled character of this home. The flagstone entry opens into an expansive living room with a wall of windows, cathedral ceiling and enormous tiled fireplace and leads to a step-down dining room/kitchen combination with large center island, breakfast bar and indoor barbecue, an entertainer's dream! Step down to a fireplaced family room with sliders to a large outdoor patio and barbecue or step up to 3 generous bedrooms, a full tiled bathroom and a master bedroom en-suite. You will be taken in by the intact and pristine aesthetics of this home. A 2 car attached garage leads to a lower level den/playroom, half bath and office. GREAT LOCATION... Public Trans on one end, the beauty of Belle Isle on the other.

Listed by Sharon Tallent and David Tallent of Compass

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$
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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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111 Winthrop Shore Drive Winthrop MA 02152

MLS Number 72733108

  • Single Family Detached
  • Bathroom 3
  • Rooms 9
  • Bedrooms 3
  • Square Feet 2,152

Beautifully appointed Ocean front property on Winthrop Beach !! Amazing views from the brand new oversized 2nd floor deck overlooking the Atlantic. First Floor: Brand new kitchen. New stainless steel appliances and cabinets. Brand new hardwood floors. 1st floor Bedroom !!. Living Room with charming fire place and panoramic windows for perfect ocean views. Bonus room can serve as a home office. Second Floor: Large foyer. Plenty of space to furnish as an additional entertainment room. Master BR w/ full bath and walkout to deck overlooking the ocean. 3rd BR is Spectacular !! Enjoy the Ocean view from your BR, complete with own fireplace. Bonus room on 2nd floor as well !! Leads to a brand new 2nd floor deck in the rear of the home for additional peace and quiet. Driveway space for 2 cars (rare). Brand new Water Heater and Furnace. Must see !!!

Listed by Anthony Freni of Freni Realty Associates

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$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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 Upland Road Winthrop MA 02152

Winthrop, MA89 Upland Road

Price$1,060,000

Est. Mortgage: $/month

Price Changed

MLS Number 72727810

  • Single Family Detached
  • Bathroom 1
  • Rooms 6
  • Bedrooms 3
  • Square Feet 964

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. Showings by appointment and ***COVID-19 GUIDELINES REQUIRED.

Listed by Sharon Tallent and David Tallent of Compass

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$
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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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251 Court Road Winthrop MA 02152

Winthrop, MA251 Court Road

Price$874,900

Est. Mortgage: $/month

MLS Number 72712141

  • Single Family Detached
  • Bathroom 2
  • Rooms 7
  • Bedrooms 3
  • Square Feet 1,914

Have you ever dreamed of waking up to the breathtaking views of the Boston skyline from your oceanfront property? Now is your chance to own your next dream home on top of the hill in Winthop's most sought after neighborhood. This solid brick, single family home is just only a few minutes away from the heart of Boston and Logan airport. The ability to build your own dock in the back gives this property potential beyond your wildest dreams. The deck right off the living room lets you just sit and enjoy the breeze with your amazing unobstructed harbor views of the city! Inside renovations are required but the potential is limitless.

Listed by Robert Carroll of Cameron Prestige, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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17R Thornton Park Winthrop MA 02152

MLS Number 72702820

  • Single Family Detached
  • Bathroom 1
  • Rooms 4
  • Bedrooms 2
  • Square Feet 1,021

Something from a fairy tale. This historic home was originally built as one of Winthrop's Narrow Gauge Railroad stations, and is one of the last remaining remnants of the entire rail system here in town. Featuring just over 1000 square feet of living area, this turn-key abode is the perfect condo alternative for someone who enjoys the privacy and autonomy of owning a single family home. NO CONDO FEES! Many of the systems have been recently replaced including windows, heat, air conditioning, hot water, and roof. Both the bathroom and kitchen feature radiant heat flooring. While this property does not have a basement, there is plenty of storage in an enormous unfinished attic space on the second floor. Please note: there is a 9ft wide easement to access the lot from the driveway of 15 Thornton Park, which is referenced in the deed.

Listed by The Hines Group and Stephen Hines of Robert Paul Properties

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$
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$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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5 Oceanview Street Winthrop MA 02152

Winthrop, MA5 Oceanview Street

Price$399,000

Est. Mortgage: $/month

MLS Number 72669593

  • Single Family Detached
  • Bathroom 1
  • Rooms 6
  • Bedrooms 3
  • Square Feet 1,114

Charming 3 bedroom cottage on level corner lot. Wide pine plank flooring in great condition. Spacious fenced in yard with planting beds and well established birch tree. Walk to the beach in minutes. Close proximity to shops, restaurants and highway.

Listed by Chad Smith of Mariano Smith & Co.

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$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 2020
* 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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