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Newest Listings in Winchester, MA

4 Bonad Rd, Winchester image
4 Bonad Rd, Winchester $1,099,000

This gorgeous colonial is located in a popular neighborhood on a quiet side street. As you enter the home, you’re greeted by the fireplaced living room with its wall of w...

  • 3 Beds
  • 2 Baths
  • 73005417 MLS
  • NEW Status
Courtesy of Barrett Sotheby's International Realty

Listing courtesy of Anne Spry from Barrett Sotheby's International Realty

241 Cross, Winchester image
241 Cross, Winchester $775,000

Attention contractors, builders, and DIY enthusiasts! Looking for a hidden gem in Winchester with many possibilities. Property is in the RG zone and is a conforming lot w...

  • 73004215 MLS
  • ACTIVE Status
Courtesy of Berkshire Hathaway HomeServices Commonwealth Real Estate

Listing courtesy of Danielle Storella from Berkshire Hathaway HomeServices Commonwealth Real Estate

171 Swanton Street Unit 39, Winchester image
171 Swanton Street Unit 39, Winchester — The Village $669,000

Move in Ready! Freshly painted with many updates including new hardwood floors. This END UNIT has an extra family room. Only end units have this bonus space. The first fl...

  • 2 Beds
  • 3 Baths
  • 73004031 MLS
  • The Village Bldg.
  • ACTIVE Status
Courtesy of William Raveis R.E. & Home Services

Listing courtesy of Stephanie Singer from William Raveis R.E. & Home Services

115 Washington Street Unit 1B, Winchester image
115 Washington Street Unit 1B, Winchester — Church Place Condiminiums $489,000

Welcome to easy living! This is the home you’ve been looking for. There’s nothing to do but move right in and enjoy this meticulously maintained home. This beautifully up...

  • 1 Beds
  • 1 Baths
  • 73003534 MLS
  • Church Place Condiminiums Bldg.
  • ACTIVE Status
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

Listing courtesy of Paula R. Sughrue from Better Homes and Gardens Real Estate - The Shanahan Group

41 Jefferson, Winchester image
41 Jefferson, Winchester $1,550,000

Nestled on Winchester, East Hill location much sought after Jefferson Road. Close to the Fells Reservation, as well as Winchester Center, restaurants and the commuter ra...

  • 4 Beds
  • 4 Baths
  • 73003461 MLS
  • ACTIVE Status
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

Listing courtesy of Mary Price from Better Homes and Gardens Real Estate - The Shanahan Group

108 Arlington St, Winchester image
108 Arlington St, Winchester $1,125,000

Lovely home in delightful Ambrose neighborhood. Move right in to this immaculate cape with two bedrooms on the first floor and an office. Third bedroom is located on the...

  • 3 Beds
  • 2 Baths
  • 73003234 MLS
  • ACTIVE Status
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

Listing courtesy of Nannette Shanahan from Better Homes and Gardens Real Estate - The Shanahan Group

5 Partridge Ln, Winchester image
5 Partridge Ln, Winchester $1,990,000

Quiet cul-de-sac living in a beautiful neighborhood, meticulously maintained & updated Colonial with an exceptionally large level yard. An entertainer’s dream, this home...

  • 5 Beds
  • 4 Baths
  • 73002735 MLS
  • ACTIVE Status
Courtesy of Keller Williams Realty Boston Northwest

Listing courtesy of Andersen Group Realty from Keller Williams Realty Boston Northwest

25 Jefferson Road, Winchester image
25 Jefferson Road, Winchester $1,600,000

Charming, spacious & inviting 3 bedroom, 3.5 bath ranch in much loved neighborhood . A welcoming entry foyer with sky lite leads to a large living room with fireplace. E...

  • 3 Beds
  • 4 Baths
  • 72999074 MLS
  • ACTIVE Status
Courtesy of Realty Executives Boston West

Listing courtesy of Karen Piedra from Realty Executives Boston West

102 Pond Street, Winchester image
102 Pond Street, Winchester $1,175,000

Completely renovated "smart" colonial within walking distance of Lynch elementary school! With seasonal views of Winter Pond, this beautiful sunny home boasts Jerome Bail...

  • 4 Beds
  • 2 Baths
  • 73002599 MLS
  • ACTIVE Status
Courtesy of Coldwell Banker Realty - Winchester

Listing courtesy of Seeme Moreira from Coldwell Banker Realty - Winchester

241 Cross, Winchester image
241 Cross, Winchester $775,000

Attention contractors, builders, and DIY enthusiasts! Looking for a hidden gem in Winchester with many possibilities. Convenient one-floor living in this ranch style home...

  • 2 Beds
  • 1 Baths
  • 73002145 MLS
  • ACTIVE Status
Courtesy of Berkshire Hathaway HomeServices Commonwealth Real Estate

Listing courtesy of Danielle Storella from Berkshire Hathaway HomeServices Commonwealth Real Estate

7 Conant Road Unit 22, Winchester image
7 Conant Road Unit 22, Winchester $529,000

Awesome opportunity to own a meticulously maintained, one level living 2-BR 2-Bath in the sought after “The Willows” condominium! This south-facing, spacious corner unit ...

  • 2 Beds
  • 2 Baths
  • 73002096 MLS
  • ACTIVE Status
Courtesy of Phoenix Real Estate

Listing courtesy of Wei Fu from Phoenix Real Estate

43 Central St., Winchester image
43 Central St., Winchester $2,050,000

Beautifully renovated colonial with 5 bedrooms and 4 1/2 baths in a quiet and highly desirable neighborhood. Enter into a gorgeous foyer with a beautiful staircase and...

  • 5 Beds
  • 4 Baths
  • 73001958 MLS
  • ACTIVE Status
Courtesy of Coldwell Banker Realty - Back Bay

Listing courtesy of Jayne Zeamer from Coldwell Banker Realty - Back Bay

5 Squire Road, Winchester image
5 Squire Road, Winchester $1,950,000

Prepare to fall in love w/this luxurious 6-bedroom dream home. Modern, open layout, perfect for today’s lifestyle. Comfortably work at home, entertain, & spend time w/fam...

  • 6 Beds
  • 4 Baths
  • 72999744 MLS
  • ACTIVE Status
Courtesy of Coldwell Banker Realty - Concord

Listing courtesy of The Laura Baliestiero Team from Coldwell Banker Realty - Concord

4 Norwood Street, Winchester image
4 Norwood Street, Winchester $1,399,000

HISTORIC HOME & WALK TO TOWN! Spectacular location with plenty of vintage characteristics like the floor to ceiling windows and original hardwood flooring. Generous kitch...

  • 3 Beds
  • 2 Baths
  • 73000824 MLS
  • ACTIVE Status
Courtesy of Coldwell Banker Realty - Winchester

Listing courtesy of The Marrocco Group from Coldwell Banker Realty - Winchester

19 Cedar Street Unit 19, Winchester image
19 Cedar Street Unit 19, Winchester $1,199,999

Come see this beautiful 2400 square feet two unit complex townhouse in lovely Winchester. Built in 2011. This home is on 3 levels plus the basement. It has 4 bedrooms and...

  • 4 Beds
  • 4 Baths
  • 73000515 MLS
  • ACTIVE Status
Courtesy of Berkshire Hathaway HomeServices Commonwealth Real Estate

Listing courtesy of Fintan Doherty from Berkshire Hathaway HomeServices Commonwealth Real Estate

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, landlords 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, leasing or renting 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, leasing or renting. 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.

Search All Winchester Real Estate

The Town of Winchester is approximately 8 miles from Boston and it is the 7th wealthiest community in Massachusetts.  Sought after for it's high ranking schools, whimsical town center, and charming New England neighborhoods, Winchester often makes it's way to the top of the wish list for many home buyers.  It's home to the yummy Gingerbread Construction company, walking trails at Horn Pond, and unique shops and restaurants in the center of town.

Learn More About Winchester:

WINCHESTER SCHOOLS

TOWN HALL

WINCHESTER LIBRARY

HORN POND

WINCHESTER RECREATION PROGRAM

WINCHESTER RESIDENTS FACEBOOK PAGE

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