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Winchester Homes and Condos for Sale

Winchester is a lovely small town in Middlesex County, Massachusetts. Established in 1640 and incorporated in 1850, today Winchester sits eight miles north of Boston and is home to over 25,000 people spanning just over six square miles across the 01890 zip-code. Known as a bedroom community, or commuter town, of Boston, Winchester is highly accessible via the Wedgemere and Winchester Center stations on the Lowell Line of the MBTA Commuter Rail. 

The town of Winchester focuses on being a “green” community and with that, aims to preserve the miles of beautiful outdoor space. Homeowners in Winchester are encouraged to get into nature and visit, picnic, and walk along places like the Mystic Lakes, Aberjona River, Davidson Park, and the vast Middlesex Fells Reservation. Folks can relax on the Leonard Field and Beach looking onto the Aberjona after a long day at work, or they can take loved ones or meet friends at the youth and recreation centers. Athletes have a dozen fields and open space in which to practice solitarily or with teams, and avid golfers will love the terrain at the Winchester Country Club.

Winchester real estate in Massachusetts beckons forth buyers looking for classically-stunning architecture and spacious, private properties. Condos and houses in Winchester can be found with floor plans of 1,000-3,000 square feet while estates promoting grandeur boast up to 7,000 square-foot layouts with lakefront views. If you are interested in buying one of the gorgeous Winchester homes for sale in Massachusetts, please contact us today. 

Newest Winchester Homes and Condos for Sale

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
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.
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.
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
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
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
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
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
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
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
Courtesy of Phoenix Real Estate

Listing courtesy of Wei Fu from Phoenix Real Estate

45 Winford Way, Winchester image
45 Winford Way, Winchester $839,000

Welcome to 45 Winford Way, a beautiful full dormered Cape overlooking the Fells on the Winchester/Medford border that gives you the best of both worlds! Cozy up next to t...

  • 4 Beds
  • 2 Baths
  • 73002067 MLS
Courtesy of Barrett Sotheby's International Realty

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

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
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
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
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
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.

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Victoria Kustov
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Burlington, MA 01803

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