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Homes for Sale Winchester MA

Browse current homes for sale in Winchester MA. Contact Barrett Sotheby's International Realty or call our Winchester office directly at 781-729-7900 with any questions or to schedule a viewing. Register on the site to save your favorite listings and to receive email notifications when similar listings come to market.

Winchester, Massachusetts is 8 miles north of Boston. Winchester is child-friendly and home to lakes, parks, and trails. Winchester keeps its public spaces well maintained. Winchester is a family-friendly bedroom community. 

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32 Tufts Road Winchester MA 01890
Open House

MLS Number 73161766

  • Residential
  • Next Open House: Sat 09/23 11:00 am. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,139

Nestled in Winchester's prestigious neighborhood, this charming Garrison Colonial home is a suburban paradise! Enjoy unrivaled convenience with its prime location near Muraco School, Leonard Field, and enjoy the natural beauty of the nearby Middlesex Fells Reservation. This home is located on an expansive and flat lot with a generous private yard and play area. The first floor features gorgeous hardwood floors, a beautiful living room with elegant fireplace, a formal dining room, and an upgraded kitchen with granite marble countertops. A bonus office room, doubling as guest space, adds versatility. Upstairs, three spacious bedrooms and a full bath provide comfort. The finished basement offers versatile bonus space with the potential for an expanded office space or home theater, along with a well-organized laundry room. Recent updates include new kitchen and appliances and new bathrooms, enhancing both charm and functionality. Make this prestigious Winchester residence your forever home

Listed by Rose Hall and Sandy Zhang of Blue Ocean Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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28 Henry Street Winchester MA 01890

Winchester, MA28 Henry Street

Price$699,900

Est. Mortgage: $/month

Open House

MLS Number 73161480

  • Residential
  • Next Open House: Thu 09/21 4:30 pm. to 6:00 pm.
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,279

This two bedroom one full bath cape is ready for that savvy buyer trying to get into Winchester willing to put in some sweat equity, or those seeking to “right-size”, and investors too. First floor offers an updated kitchen with SS appliances, recessed lighting, granite dining and prep island, and tons of cabinets. Kitchen leads to the enormous deck and flagstone patio that provides the perfect backyard oasis with great privacy. The living room is centered around the wood-burning fireplace, featuring tons of windows providing lovely natural light and adorned by crown moulding. Two good sized bedrooms and refreshed full bath round out this main living level. The bonus room in lower level hosts a fireplace, WW carpeting and boasts access to one car garage and separate laundry room. Located in the esteemed Vinson-Owen School district and in close proximity to Wright-Locke Farm, Mullen Field and McClennen Park make this a hidden gem in Winchester.

Listed by Alison Socha Group and Heidi Russo of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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22 Grove Place Winchester MA 01890
Open House

MLS Number 73161443

  • Condo
  • Next Open House: Sat 09/23 11:00 am. to 12:30 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 3,045

Welcome to an extraordinary opportunity at White Horse Commons! This is one of just two condos in the community that offers the privacy and convenience of a free-standing townhouse with an attached 2-car garage. Numerous updates and thoughtful features make this property truly special, include a new boiler and HVAC system in March 2021, new Anderson windows & window shades, new appliances, new washer &dryer. A first-floor bedroom with a full bathroom provides convenience and versatility. Enjoy outdoor living with a spacious deck off the kitchen for al fresco dining and a private deck off the living room, both perfect for relaxation and entertainment. Convenient garage access directly from the kitchen makes unloading groceries and everyday tasks a breeze. The lower level offers a family room with built-in cabinets, a wet bar, and a bonus room, providing flexible space for various needs. Don't miss the opportunity to make it your own.

Listed by Peter Cote of Redfin Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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18 Royalston Avenue Winchester MA 01890

Winchester, MA18 Royalston Avenue

Price$2,499,999

Est. Mortgage: $/month

Open House

MLS Number 73161337

  • Residential
  • Next Open House: Sat 09/23 1:30 pm. to 3:00 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 5,535

We don't know if you're ready to be WOW'ed like THIS! This new construction property is beaming with lux, trendy, and statement making features throughout. Let's begin at the entrance where you'll be welcomed by a herringbone highlight in the flooring that leads you to a bridal staircase like one you see in a magazine! To one side of the main level is a home office, full bath, & 1st floor bedroom. The opposite side of the main level boasts a dining room and a family room with 3-sided fireplace to the kitchen, the true gem of this special property. With vaulted ceilings and skylights, top of the line appliances, an oversized pantry, and an eat-in area this truly is the HEART of this HOME. As you make your way upstairs you'll find 3 additional bedrooms, including the primary suite. Perhaps the best feature of the 2nd floor? A front balcony that overlooks the front yard and quiet neighborhood. BONUS; there is a HUGE rear deck & lower level w/ full bath and multiple flex spaces. AMAZING!

Listed by Vita Realty Group and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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46 Edward Drive Winchester MA 01890
Open House

MLS Number 73161166

  • Condo
  • Next Open House: Sat 09/23 1:00 pm. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,859

Step right into this spacious townhouse at Pepper Hill Estates, situated in the coveted Vinson Owen elementary school district. This fully renovated home, with over $120,000 invested in upgrades, offers an open living room and dining area with a fireplace, while maintaining a separate kitchen and den/office for added privacy.The lower level boasts a large family room, a third bedroom, a full bath, and laundry facilities, all with walk-out access to the outdoors. Upstairs, two generously sized bedrooms each come with their own full baths, including a master suite with his and hers walk-in showers.With the added convenience of an attached garage, this property provides modern comfort and style. Don't miss your opportunity to live in one of Winchester's top school areas. Take the leap into homeownership in this fantastic neighborhood, all for the incredible price of $950,000. Your new home awaits!All Offer will be review on 9/25/2023 7PM

Listed by Zhonghui Zhu of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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18 Alden Lane Winchester MA 01890

Winchester, MA18 Alden Lane

Price$2,595,000

Est. Mortgage: $/month

Open House

MLS Number 73160998

  • Residential
  • Next Open House: Sat 09/23 1:30 pm. to 3:00 pm.
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 6,338

Treetop views and top of the line construction! This 5+ bedroom, 5.5 bathroom beauty is located in the coveted Lincoln Elementary School District. The first level consists of a formal living room, open concept family room and dining room, gourmet kitchen with pantry, 1.5 bathrooms, 1st floor bedroom/home office, and a large mudroom directly off of the 2 car garage. The second level is home to 4 additional bedrooms, including one junior suite and the primary with HUGE walk-in closet, spa-like bathroom and private deck with gorgeous views. Additional living space can be found in the finished walk-out lower level with wet bar and possibilities galore! A gym, media room, additional bedroom, and recreation room are all possible in this space! You won't want to miss out on this beautiful home that is near completion by a premier local builder.

Listed by Vita Realty Group and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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16 Marshall Road Winchester MA 01890

Winchester, MA16 Marshall Road

Price$1,595,000

Est. Mortgage: $/month

Open House

MLS Number 73160861

  • Residential
  • Next Open House: Fri 09/22 5:00 pm. to 6:30 pm.
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,866

This meticulously maintained 4 bedroom, 3 bath modern home opens with a thoughtful, sunlit layout featuring multiple living spaces including, a stone fireplace, oversized skylights, rich hardwood floors and an updated kitchen equipped with premium appliances. Easily transition from the main living area to a covered porch and spacious deck, revealing outdoor living with a peaceful pond and waterfall. The huge master suite boasts a vaulted ceiling, cozy fireplace and private deck. The luxurious dressing room and full bath with skylight complement this distinguished space. Two additional bedrooms and full bath with cathedral ceilings and skylight complete the upper level. The lower level has been designed as an ideal guest suite, incorporating a comfortable bedroom, full bathroom and versatile main room with laundry and direct access to a generous two-car garage and extra storage space. Conveniently located near the Wedgemere train station, Winchester Center, commuter routes and schools.

Listed by The Petrowsky Jones Group and Nicholas Mescia of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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89 Wildwood Street Winchester MA 01890

Winchester, MA89 Wildwood Street

Price$2,499,000

Est. Mortgage: $/month

MLS Number 73160639

  • Residential
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 4,800
  • High School Winchester Hs

NEW CONSTRUCTION!! Must see this gorgeous 7 bed 5.5 bath home w/ thoughtful design & high end finishes! This luxury home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen features an oversized island with seating/ quartz countertops, high-end professional appliances, breakfast nook/morning dining area. Direct access off the kitchen w/ sliders leading out to the large & private rear yard. Off the kitchen is a spacious family room with gas fireplace. The first floor also has a formal dining room & 7th bed OR home office with 3/4 bath. The second level master suite is spacious & offers an oversized walk-in closet, a lavish bath with tiled shower/glass enclosure, double vanities & soaking tub! The 2nd level also includes 3 additional beds & 2 baths; two beds with adjoining bath plus laundry room. Finished lower level media/ rec room and additional bedroom w/ full bath. Oversized 2 car garage, mudroom~ close to town!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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20 Bellevue Avenue Winchester MA 01890

Winchester, MA20 Bellevue Avenue

Price$2,699,000

Est. Mortgage: $/month

MLS Number 73160636

  • Residential
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 6,300
  • High School Winchester Hs

NEW CONSTRUCTION! This spacious 6 bed, 6.5 bath home by a top local builder has it all! With over 6,300sf of living space you won't want to miss this stunning home. The first flr offers a gourmet kitchen w/ oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dining area. Off the kitchen is a spacious family rm w/gas fireplace & direct exterior access w/ sliders leading to a large patio & great yard. The first floor also offers a guest bedrm or home office w/ full bath, mudroom and powder rm. The second level primary suite includes huge walk-in closet, lavish bath w/double vanities, oversized shower & soaking tub! Three additional beds, 2 full baths & laundry room finish this level. The finished third flr is a large loft/playroom/gym w/ full bath. Finished lower level media/ rec room, additional bedroom w/ full bath and wine cellar. 2 car garage direct entry to great mudroom! Conveniently located just 7 miles north of Boston nr Hospital & the Fells!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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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12 Ardley Place Winchester MA 01890

Winchester, MA12 Ardley Place

Price$1,849,000

Est. Mortgage: $/month

Open House

MLS Number 73160572

  • Residential
  • Next Open House: Sat 09/23 1:00 pm. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,846

Rare opportunity to own this newly renovated 3/4 bedroom home in a truly special, picturesque neighborhood! This spacious home with stunning great room featuring walls of windows & vaulted ceilings, has been tastefully updated combining modern amenities with 1930s charm. A lovely front entry with stone walkway & perennial gardens welcomes you into the home. A large formal living room w/ fplc, family/great room, newly updated eat in kitchen w/Thermador appliances,1/2 bath & french door access to fabulous patio, yard & firepit; the maturely landscaped level yard offers privacy, peace and tranquility. The second floor offers three bedrooms, a primary bedroom w/ ensuite tiled bath, plus a spacious hall bath w/ designer finishes. The third offers a large bonus room, the basement is ground level with direct/private entrance offering 4th bed or rec room. and half bath. Must see this great home just a short distance to Lynch school, Big & Little Winter ponds, Horn Pond and Winchester center!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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

246 Washington Street Winchester MA 01890
Open House

MLS Number 73159657

  • Condo
  • Next Open House: Sat 09/23 11:00 am. to 12:00 pm.
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,660

Move right in and enjoy this lovely home close to downtown with incredible curb appeal and feel of a single family! You will love to call this great property home, with beautiful flowing first floor, high ceilings & original detail blended with tasteful updates throughout. Spacious bedrooms, updated bath and finished lower level offers a cozy bonus /family room. The lush back yard is private with a lovely yard & patio surrounded by perennial plantings plus a 1 car garage and plenty of parking. Located just minutes away from the towns center, train, restaurants, Fells Reservation and more! Don't miss this sunny & happy home!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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

246 Washington Street Winchester MA 01890
Open House

MLS Number 73159656

  • Residential
  • Next Open House: Sat 09/23 11:00 am. to 12:00 pm.
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,660

Move right in and enjoy this lovely home close to downtown with incredible curb appeal and feel of a single family! You will love to call this great property home, with beautiful flowing first floor, high ceilings & original detail blended with tasteful updates throughout. Spacious bedrooms, updated bath and finished lower level offers a cozy bonus /family room. The lush back yard is private with a lovely yard & patio surrounded by perennial plantings plus a 1 car garage and plenty of parking. Located just minutes away from the towns center, train, restaurants, Fells Reservation and more! Don't miss this sunny & happy home!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 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

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