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Winchester

The town of Winchester is located 8 miles north of Boston off Route 93. At one time, Winchester was much larger,  encompassing parts of nearby Medford, Arlington and Cambridge.  Winchester real estate is made up of picturesque residential neighborhoods with mostly single family homes that range from mid-sized to grand estates. Downtown has condominiums and multifamily homes mixed in with its shops.  Residents enjoy Winchester's restaurants, the local pub and boutique stores.

Winchester Demographic Stats

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Latest Winchester Listings

27 Mount Pleasant St, Winchester image
27 Mount Pleasant St, Winchester $3,199,000

New construction custom built home-walk to downtown. While the floor plan has been finalized, there is still opportunity to customize the home of your dreams. The finis...

  • 5 Beds
  • 5 Baths
  • 73005441 MLS
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

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

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

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

  • 3 Beds
  • 2 Baths
  • 73005417 MLS
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
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

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

53 Hutchinson Rd, Winchester image
53 Hutchinson Rd, Winchester $2,900,000

Meticulously cared for Colonial with picture perfect golf course views! This stunning "Smart" home has been designed with incredible craftsmanship and to suit today's mod...

  • 6 Beds
  • 5 Baths
  • 73000316 MLS
Courtesy of Keller Williams Realty Boston Northwest

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

115 Washington St Unit 1A, Winchester image
115 Washington St Unit 1A, Winchester — Church Place Condominiums $599,900

Beautiful, highly sought after Church Place Condominium! Centrally located, you will enjoy all of the amenities you would expect of in town living! Just a hop, skip, and...

  • 2 Beds
  • 1 Baths
  • 72999491 MLS
  • Church Place Condominiums Bldg.
Courtesy of RE/MAX On The River, Inc.

Listing courtesy of Kerrilynn Yemma from RE/MAX On The River, Inc.

17 Clark Street Unit 17, Winchester image
17 Clark Street Unit 17, Winchester $824,900

OPEN HOUSE 6/17~4-6PM beautifully RENOVATED townhome that lives and feels like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 ...

  • 3 Beds
  • 2 Baths
  • 72999357 MLS
Courtesy of Wilson Wolfe Real Estate

Listing courtesy of Chrisanne Connolly from Wilson Wolfe Real Estate

17 Clark Street Unit 17, Winchester image
17 Clark Street Unit 17, Winchester $824,900

OPEN HOUSE 6/17~4-6PM beautifully RENOVATED townhome that lives and feels like a single family is the perfect location to enjoy all Winchester has to offer; barely a 1/4 ...

  • 3 Beds
  • 2 Baths
  • 72998841 MLS
Courtesy of Wilson Wolfe Real Estate

Listing courtesy of Chrisanne Connolly from Wilson Wolfe Real Estate

58 Bacon Street, Winchester image
58 Bacon Street, Winchester $1,899,000

VERY SPACIOUS updated 1925 Colonial in incredible location! This thoughtfully designed 6 bed, 5.5 bath home is ideal for family living on 4 finished levels. The main floo...

  • 6 Beds
  • 6 Baths
  • 72998832 MLS
Courtesy of Coldwell Banker Realty - Winchester

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

28 Henry St, Winchester image
28 Henry St, Winchester $749,000

Classic ranch style home with room to grow and expand. Freshly painted inside and out. Family friendly neighborhood in the esteemed Vinson Owen School district. Readi...

  • 2 Beds
  • 1 Baths
  • 72998264 MLS
Courtesy of OwnerEntry.com

Listing courtesy of Dave White from OwnerEntry.com

38 Farrow St, Winchester image
38 Farrow St, Winchester $1,050,000

Quaint Colonial located in close proximity to schools, Horn Pond Bikeway, downtown Winchester Center and the train station for destinations beyond! Nestled in a wonderful...

  • 3 Beds
  • 3 Baths
  • 72996837 MLS
Courtesy of Keller Williams Realty Boston Northwest

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

24 Border, Winchester image
24 Border, Winchester $799,000 ▼

Beautifully renovated 3 bedroom with thoughtful and functional details. The first floor has a spacious open floor plan with a brand new kitchen at the center and convenie...

  • 3 Beds
  • 2 Baths
  • 72994840 MLS
Courtesy of Clockhouse Realty

Listing courtesy of Edward Dudley from Clockhouse Realty

13 Linden St, Winchester image
13 Linden St, Winchester $799,000

Ready to create your dream home? Situated on a dead-end street – this home offers a multitude of opportunities. Live in as-is or create your own vision for this lovely 3 ...

  • 3 Beds
  • 2 Baths
  • 72993962 MLS
Courtesy of Leading Edge Real Estate

Listing courtesy of Pirani & Wile Group from Leading Edge Real Estate

45 Brooks Street, Winchester image
45 Brooks Street, Winchester $2,499,000 ▼

Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300 sf 4 bed 4 bath ...

  • 4 Beds
  • 4 Baths
  • 72993192 MLS
Courtesy of Compass

Listing courtesy of Kim Covino & Co. Team from Compass

14 Nassau Drive, Winchester image
14 Nassau Drive, Winchester $2,599,000

Stunning custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with ...

  • 6 Beds
  • 7 Baths
  • 72989634 MLS
Courtesy of WINN Real Estate & Consulting

Listing courtesy of Weidong Li from WINN Real Estate & Consulting

73 Sheridan Cir, Winchester image
73 Sheridan Cir, Winchester $1,790,000 ▼

Stunning 4 bedroom 3.5 bath Colonial home from premier builder resides in a desirable neighborhood is a must see! Only a few minutes walk to Horn Pond. This beautiful hom...

  • 4 Beds
  • 4 Baths
  • 72989773 MLS
Courtesy of Coldwell Banker Realty - Lexington

Listing courtesy of Alina Wang from Coldwell Banker Realty - Lexington

43-A Chester Street, Winchester image
43-A Chester Street, Winchester $1,050,000

Don't miss this hidden split-level gem located in the Muraco school district and near the wonderful town center of Winchester. Tucked at the end of a long driveway this ...

  • 4 Beds
  • 2 Baths
  • 72989740 MLS
Courtesy of Compass

Listing courtesy of Team Patti Brainard from Compass

3 Alice Lane, Winchester image
3 Alice Lane, Winchester $2,699,000

NEW CONSTRUCTION!! Must see this gorgeous 4/5 bedroom home with thoughtful design & high end finishes! This luxurious home is spacious and inviting, offering a grand open...

  • 5 Beds
  • 5 Baths
  • 72986324 MLS
Courtesy of Compass

Listing courtesy of Kim Covino & Co. Team from Compass

54 Johnson Rd, Winchester image
54 Johnson Rd, Winchester $4,175,000

Presenting a new construction masterpiece that's a refreshing break from the ordinary, it's extraordinary! This exceptional home was designed to be beautiful yet casual, ...

  • 7 Beds
  • 8 Baths
  • 72984802 MLS
Courtesy of Compass

Listing courtesy of Team Suzanne and Company from Compass

22 Amberwood Drive, Winchester image
22 Amberwood Drive, Winchester $1,999,999 ▼

Stunningly renovated with curated items from around the world, this renovation project was done thoughtfully for peaceful moments. Whether you have a large family, a mult...

  • 5 Beds
  • 5 Baths
  • 72984377 MLS
Courtesy of Keller Williams Realty Boston Northwest

Listing courtesy of Beth Sager Group from Keller Williams Realty Boston Northwest

22 Glenwood Avenue, Winchester image
22 Glenwood Avenue, Winchester $1,199,000 ▼

Magnificent oversized lot! This spacious 4/5 bedroom home was recently updated and expanded & offers a new direct entry 2 car garage w/mudroom! Open airy kitchen with map...

  • 4 Beds
  • 2 Baths
  • 72984302 MLS
Courtesy of Compass

Listing courtesy of Kim Covino & Co. Team from Compass

11 Chesterford Road East, Winchester image
11 Chesterford Road East, Winchester $1,799,000 ▼

MUST SEE this delightful WATERFRONT home nestled alongside Little Winter (skating) pond with fabulous views! This updated contemporary designed home features a stunning e...

  • 4 Beds
  • 4 Baths
  • 72981610 MLS
Courtesy of Compass

Listing courtesy of Kim Covino & Co. Team from Compass

10 Sheffield Rd, Winchester image
10 Sheffield Rd, Winchester $3,550,000 ▼

Refined, elegant and turnkey, this Colonial Revival is on one of Winchester’s premier streets. Steps to train, town, and the desirable Ambrose school. Designed for entert...

  • 7 Beds
  • 6 Baths
  • 72978329 MLS
Courtesy of Keller Williams Realty Boston Northwest

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

21 Clearwater Rd, Winchester image
21 Clearwater Rd, Winchester $1,299,000

Adorable 4 bedroom 2 bath cape in top East side neighborhood! Situated across from the fells, this nicely updated home is a nature lovers dream! Offering an optional fir...

  • 4 Beds
  • 2 Baths
  • 72966331 MLS
Courtesy of Compass

Listing courtesy of Kim Covino & Co. Team from Compass

40 Elmwood Avenue Unit 1, Winchester image
40 Elmwood Avenue Unit 1, Winchester — Allegro $999,000

ATTENTION: THIS IS THE ONLY UNIT REMAINING AT ALLEGRO!! Spring has sprung! After a long winter we all get restless and are ready to be enjoying the outdoors! We can’t thi...

  • 2 Beds
  • 2 Baths
  • 72956654 MLS
  • Allegro Bldg.
Courtesy of Compass

Listing courtesy of Vita Realty Group from Compass

11 Niles Lane, Winchester image
11 Niles Lane, Winchester $3,099,000 ▼

TOP Waterside neighborhood! This custom, impeccably renovated and re-designed home offers a top location across from Mystic lake with direct private/ deeded water access ...

  • 5 Beds
  • 6 Baths
  • 72952069 MLS
Courtesy of Compass

Listing courtesy of Kim Covino & Co. Team from Compass

7 Brantwood Rd, Winchester image
7 Brantwood Rd, Winchester $979,900 ▼

Price Reduced!. Charming Colonial is within walking distance to Horn Pond. Exceptionally well cared for home with LANDSCAPED YARD. The 1st floor has a four-season enclose...

  • 3 Beds
  • 2 Baths
  • 72947675 MLS
Courtesy of Coldwell Banker Realty - Back Bay

Listing courtesy of Boston RE Group from Coldwell Banker Realty - Back Bay

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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