Winchester Massachusetts Real Estate – including MLS Listings, Homes, Condos, Townhomes, Land, Investment Property, and Foreclosures for Sale Search

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Winchester Massachusetts Information and Highlights

Winchester is a small suburban town located in Middlesex County, Massachusetts, 8 miles north of downtown Boston. It is an affluent bedroom community for professionals who work in the Greater Boston area. The population was 21,374 at the 2010 United States census.


The land on which Winchester now sits was purchased from Native Americans by representatives of the settlement of Charlestown in 1639, and the area was first settled by Europeans in 1640. In the early years of the settlement, the area was known informally as Waterfield, a reference to its many ponds and to the river which bisected the central village. In its second century, the area was referred to as Black Horse Village, after the busy tavern and hostelry in its center.

Until the middle of the 19th century, parts of Arlington, Medford, Cambridge, and Woburn comprised what is now Winchester. The movement toward incorporation of what, by this time, was called South Woburn was likely precipitated by the rise of the Whig Party in Massachusetts.


The town is roughly bisected by a central valley which is the remnant of the original course of the Merrimack River. After glacial debris effectively rerouted the Merrimack north to its current location, all that remained of its original course through present day Winchester is the Aberjona River and the several ponds it feeds en route to the Mystic Lakes on Winchester's southern border.

On its eastern third, the valley rises steeply into the wooded hills of the Middlesex Fells Reservation, in which lie the North, Middle and South Reservoirs. The western edge of the valley yields to Arlington and Lexington Heights, and the boundaries of those two towns. To the north, the town's longest border is shared with Woburn.


Winchester, Massachusetts, gets 49 inches of rain per year. The U.S. average is 37. Snowfall is 51 inches. The average US city gets 25 inches of snow per year. The number of days with any measurable precipitation is 118.

On average, there are 200 sunny days per year in Winchester, Massachusetts. The July high is around 82 degrees. The January low is 15. The comfort index, which is based on humidity during the hot months, is a 49 out of 100, where higher is more comfortable. The U.S. average on the comfort index is 44.


Shopping is always a pleasant experience when you can pair it with wine and food, all while taking a stroll through the music store.

En ka Exchange – 1037 Main St, Winchester, MA 01890 – (781) 729-6146

Pairings Wine & Food – 600 Main St, Winchester, MA 01890 – (781) 721-9463

Mouradian Guitar Co – 810 Main St, Winchester, MA 01890 – (781) 756-4877

Wine Country Inc. – 741 Main St, Winchester, MA 01890 – 781) 721-1045


The restaurants in Winchester are as unique as the city itself, with your choice of Japanese, Italian conventional or Italian bistro. This is just a sampling of why you should make Winchester one of your top destinations.

A Tavola – 34 Church St, Winchester, MA 01890 – (617) 718-5652

Sakura Restaurant – 910 Main St, Winchester, MA 01890 – (781) 721-4608

Lucia Ristorante – 13 Mt Vernon St, Winchester, MA 01890 – (781) 729-0515

Cafe Piazza Dolce – 831 Main St. #1, Winchester, MA 01890 – (781) 838-6092


The nightlife is just as varied as the day life. The entire premise of spending your late nights at a bar is to be surrounded by good friends and good food. Winchester doesn’t disappoint.

Black Horse Tavern – 32 Waterfield Rd, Winchester, 01890 – (781) 369-1620

TWK – 14 Thompson St, Winchester, MA 01890 – (781) 729-0204

Scoreboard Sports Bar and Grill – 15 Middlesex Canal Park Dr, Woburn, MA 01801 – (781) 897-4000

The Druid – 1357 Cambridge St, Cambridge, MA 02139 – (617) 497-0965


Winchester has five elementary schools (Ambrose, Lincoln, Lynch, Muraco and Vinson-Owen) and one middle school, McCall Middle School. Considered one of Boston's elite public high schools, Winchester High School was founded in 1850. The Winchester High School sports teams are known as the "Sachems" and are a part of the Middlesex league for sports. Their home turf is known as Knowlton Field where the lacrosse, football, soccer, field hockey and other teams practice and host their home games.

McCall Middle School – 458 Main St, Winchester, MA 01890 – (781) 721-7026

Muraco Elementary School – 33 Bates Rd, Winchester, MA 01890 – (781) 721-7030

Winchester High School – 80 Skillings Road Winchester, MA 01890 – (781) 721-7020

Lynch Elementary School – 10 Brantwood Rd, Winchester, MA 01890 – (781) 721-7013


Winchester is a quiet community in a somewhat rural landscape – which is evident when you’re welcomed at a farm with activities for all ages.

Winchester Historical Society – 15 High St, Winchester, MA 01890 – (781) 721-0135

Kidstock Creative Theater – 50 Cross St, Winchester, MA 01890 – (781) 729-5543

Wright Locke Farm – 78 Ridge St, Winchester, MA 01890 – (781) 721-7128


Winchester isn’t just your average, run-of-the-mill, quiet town. It’s bustling full of activity – day or night. This one of the few places in the country where you can look up at the stars in the sky and see it clearly. Winchester is definitely a diamond in the rough.

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Latest Real Estate for Sale in Winchester MA

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.