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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

62 Bacon Street, Winchester image
62 Bacon Street, Winchester $1,499,000

TOP LOCATION! Ravenscroft neighborhood! Move right in to this ideally located 4 story single family attached home close to the town center, Ginn field & Wedgemere train s...

  • 5 Beds
  • 4 Baths
  • 73091866 MLS
Courtesy of Compass

Listing courtesy of Compass .

14 Nassau Drive, Winchester image
14 Nassau Drive, Winchester $2,499,000

This gorgeous 7600 SF 6 bedroom 6 bath custom built colonial is a must see! You will be impressed with its space, natural light and beautiful detail throughout. Enter int...

  • 6 Beds
  • 6 Baths
  • 73091857 MLS
Courtesy of Compass

Listing courtesy of Compass .

15 Pilgrim Dr, Winchester image
15 Pilgrim Dr, Winchester $1,999,000

Welcome to this stunning home, nestled within a charming, established neighborhood of Winchester's coveted Westside. Boasting 4 bedrooms and 3 full baths, this immaculate...

  • 4 Beds
  • 3 Baths
  • 73091553 MLS
Courtesy of Keller Williams Realty Boston Northwest

Listing courtesy of Keller Williams Realty Boston Northwest.

10 Winchester Place Unit 302, Winchester image
10 Winchester Place Unit 302, Winchester — Winchester Place $1,475,000

DOWNTOWN WINCHESTER LOCATION! Move right into desirable Winchester Place! Offering the premiere unit in the building with 2 beds/2 baths plus a giant private deck with sp...

  • 2 Beds
  • 2 Baths
  • 73091177 MLS
  • Winchester Place Bldg.
Courtesy of Compass

Listing courtesy of Compass .

48 Everett Ave, Winchester image
48 Everett Ave, Winchester $4,450,000

Elegance and unparalleled quality abound in this magnificent waterside home that will take your breath away! With its expansive views of the Upper Mystic Lake and a priv...

  • 7 Beds
  • 7 Baths
  • 73091086 MLS
Courtesy of Compass

Listing courtesy of Compass .

20 Westland Avenue, Winchester image
20 Westland Avenue, Winchester $2,149,000

Extraordinary NEW renovation/expansion! 4 bedroom 3.5 bath colonial w/ 2 story rear addition in top west side neighborhood; the most recent project by premier design/buil...

  • 4 Beds
  • 4 Baths
  • 73091085 MLS
Courtesy of Compass

Listing courtesy of Compass .

93 Bacon St Unit 93, Winchester image
93 Bacon St Unit 93, Winchester $899,000

Charm and character highlight this spacious townhouse, located close to the center, schools and trains. It lives like a single family and makes you feel a bit like you're...

  • 4 Beds
  • 3 Baths
  • 73090549 MLS
Courtesy of Leading Edge Real Estate

Listing courtesy of Leading Edge Real Estate.

93 Bacon St, Winchester image
93 Bacon St, Winchester $899,000

This attached townhouse exudes charm and character, located close to the center, schools and trains. Serious Back Bay vibes here, nestled in a suburb just 8 miles from th...

  • 4 Beds
  • 3 Baths
  • 73090548 MLS
Courtesy of Leading Edge Real Estate

Listing courtesy of Leading Edge Real Estate.

15 Alden Ln, Winchester image
15 Alden Ln, Winchester $1,235,000

Welcome to 15 Alden Ln! From the bright, cathedral ceilinged family room, you can go out to the back deck and enjoy the exceptionally spacious backyard or stay inside and...

  • 4 Beds
  • 3 Baths
  • 73090254 MLS
Courtesy of Barrett Sotheby's International Realty

Listing courtesy of Barrett Sotheby's International Realty.

17 Stowell Rd, Winchester image
17 Stowell Rd, Winchester $1,465,000

This bright & airy classic home is completely renovated w/ great attention to detail & hardwood floors throughout. 1st flr has great circular flow between the living rm, ...

  • 4 Beds
  • 3 Baths
  • 73090241 MLS
Courtesy of Barrett Sotheby's International Realty

Listing courtesy of Barrett Sotheby's International Realty.

7 Standish Ln, Winchester image
7 Standish Ln, Winchester $2,300,000

New construction in one of Winchester's most popular neighborhoods near Middlesex Fells, move right in and enjoy. This home was custom designed to provide a main floor of...

  • 5 Beds
  • 4 Baths
  • 73089749 MLS
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

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

4 Valleywood Cir, Winchester image
4 Valleywood Cir, Winchester $1,125,000

Don't miss out on this charming 3 bedroom, 3 bath home in Winchester, situated on over half an acre at the end of a quiet cul-de-sac. The spacious main floor features bea...

  • 3 Beds
  • 3 Baths
  • 73089610 MLS
Courtesy of Coldwell Banker Realty - Lexington

Listing courtesy of Coldwell Banker Realty - Lexington .

73 Thornberry Rd, Winchester image
73 Thornberry Rd, Winchester $1,475,000

From the moment you step inside this 4 bedroom & 2.5 bath home, you’ll be struck by the timeless elegance & warm ambiance of this classic Colonial. Situated on a sprawlin...

  • 4 Beds
  • 3 Baths
  • 73089498 MLS
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

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

5 Manomet Road, Winchester image
5 Manomet Road, Winchester $1,649,000

Swing into Spring in this 4 bedroom, 4 bath new construction home in the Ambrose School District across from fabled Myopia Hill. Come see this transitional, meticulous ho...

  • 4 Beds
  • 4 Baths
  • 73089326 MLS
Courtesy of Marino Real Estate Group

Listing courtesy of Marino Real Estate Group.

118 Wendell Street, Winchester image
118 Wendell Street, Winchester $899,000

Hurry! This charming cape located in desirable Winchester is just waiting to be transformed into the luxurious home of your dreams! Don’t miss out on this meticulously ma...

  • 3 Beds
  • 2 Baths
  • 73085295 MLS
Courtesy of Premium Realty Group LLC

Listing courtesy of Premium Realty Group LLC.

424 S Border Rd, Winchester image
424 S Border Rd, Winchester $749,900

Attention all investors, rehabbers, or buyers looking for a fixer-upper! Introducing 424 S Border Rd located in the heart of Winchester, across from conservation land and...

  • 3 Beds
  • 2 Baths
  • 73084889 MLS
Courtesy of The Presti Group, Inc.

Listing courtesy of The Presti Group, Inc..

8 Niles Lane, Winchester image
8 Niles Lane, Winchester $5,995,000

MAJESTIC LAKEFRONT ESTATE! Situated directly on the Mystic lake w/ expansive yard & breathtaking views offering the most gorgeous and serene setting in all of Winchester....

  • 8 Beds
  • 8 Baths
  • 73083677 MLS
Courtesy of Compass

Listing courtesy of Compass .

30 Symmes Road Unit 30, Winchester image
30 Symmes Road Unit 30, Winchester — Symmes Condominium $1,170,000 ▼

Have the feel of a single-family home with EXCLUSIVE entrance on Symmes Rd and driveway with 2-car garage plus outdoor space with rear yard and patio. Outstanding locatio...

  • 5 Beds
  • 2 Baths
  • 73082439 MLS
  • Symmes Condominium Bldg.
Courtesy of Berkshire Hathaway HomeServices Commonwealth Real Estate

Listing courtesy of Berkshire Hathaway HomeServices Commonwealth Real Estate.

30 Symmes Road, Winchester image
30 Symmes Road, Winchester $1,170,000 ▼

Have the feel of a single-family home with EXCLUSIVE entrance on Symmes Rd and driveway with 2-car garage plus outdoor space with rear yard and patio. Outstanding locatio...

  • 5 Beds
  • 2 Baths
  • 73082440 MLS
Courtesy of Berkshire Hathaway HomeServices Commonwealth Real Estate

Listing courtesy of Berkshire Hathaway HomeServices Commonwealth Real Estate.

9 Amberwood Dr, Winchester image
9 Amberwood Dr, Winchester $2,499,000 ▼

Newly constructed "smart home" with endless flexible living areas and stunning bits of convenience around every corner! Beautifully landscaped and ideal for children; dir...

  • 5 Beds
  • 5 Baths
  • 73082393 MLS
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

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

200 Swanton St Unit T28, Winchester image
200 Swanton St Unit T28, Winchester — Parkview Condos $329,900 ▼

Welcome to an exceptional opportunity to own a stunning one-bedroom condo on the Terrace Level of Parkview Condominiums, located just outside of Winchester center. Nestle...

  • 1 Beds
  • 1 Baths
  • 73080248 MLS
  • Parkview Condos Bldg.
Courtesy of Century 21 North East Homes

Listing courtesy of Century 21 North East Homes.

22 Chester St, Winchester image
22 Chester St, Winchester $808,000 ▼

Farmhouse style colonial with covered front porch in Muraco Dist. Seller made a multitude of renovations. Look past the clutter and find the appealing original wide pine ...

  • 3 Beds
  • 1 Baths
  • 73078101 MLS
Courtesy of Lamacchia Realty, Inc.

Listing courtesy of Lamacchia Realty, Inc..

40 Elmwood Avenue Unit 10, Winchester image
40 Elmwood Avenue Unit 10, Winchester — Allegro $1,349,999

The CROWN JEWEL of the building! This truly special unit is flooded with light and boasts (2) private decks, (2) master suite options, and (2) garage parking spaces. All...

  • 2 Beds
  • 3 Baths
  • 73073522 MLS
  • Allegro Bldg.
Courtesy of Compass

Listing courtesy of Compass .

40 Elmwood Avenue Unit 4, Winchester image
40 Elmwood Avenue Unit 4, Winchester — Allegro $974,900

The new year is all about starting fresh; pursuing things you may not have achieved during the year before. Perhaps you missed out on an opportunity to live in Winchester...

  • 2 Beds
  • 2 Baths
  • 73068446 MLS
  • Allegro Bldg.
Courtesy of Compass

Listing courtesy of Compass .

8 Glenwood Ave Unit 8, Winchester image
8 Glenwood Ave Unit 8, Winchester $1,500,000 ▲

High Quality New Construction in convenient location easy access to everything. Home features open concept Kitchen, dining area and living room perfect for entertaining....

  • 3 Beds
  • 3 Baths
  • 73066850 MLS
Courtesy of Burns & Egan Realty Group, LLC

Listing courtesy of Burns & Egan Realty Group, LLC.

132 Cambridge St, Winchester image
132 Cambridge St, Winchester $950,000

Welcome to this move in ready Craftsman Colonial Style Home. Walk into an open Living room and Dining room with gleaming hardwood floors. The Kitchen is open and has plen...

  • 3 Beds
  • 3 Baths
  • 73066517 MLS
Courtesy of Premier Property Solutions, LLC

Listing courtesy of Premier Property Solutions, LLC.

1 Socrates Way, Winchester image
1 Socrates Way, Winchester $1,995,000

SPACE GALORE! Welcome to this fantastic 5 BR, 3.5 bath colonial on a little over an acre lot. The comfortable floor plan maximizes space with plenty of room for entertain...

  • 5 Beds
  • 4 Baths
  • 73054183 MLS
Courtesy of Home Shop Properties, Inc.

Listing courtesy of Home Shop Properties, Inc..

39 Everett Avenue, Winchester image
39 Everett Avenue, Winchester $2,300,000

Welcome to 39 Everett Avenue, a classic mid-century modern home situated on a 25,000+ sf lot in the heart of Winchester’s coveted Everett Ave. neighborhood. Embrace the a...

  • 5 Beds
  • 4 Baths
  • 73037552 MLS
Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

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

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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