South Cheshire Neighborhoods

South Cheshire Neighborhoods


The South Cheshire neighborhoods are always buzzing with excitement.  In fact, South Cheshire is home to the highest single drop waterfall in the state...Roaring Brook Falls! It is absolutely spectacular after a heavy rain or in early spring, but is a beautiful sight to behold any time, and has been perserved in it's natural state by the Cheshire Land Trust.  

South Cheshire is primarily made up of single family homes (83%) mostly 3-4 bedrooms with a median price of $325,474. Most of these homes were built between 1940- 1999, with some being built as early as 1800. Because of it's access to major transportation roads; Routes 10, 42, 68 and 70 it is an excellent choice for commuters who work in or outside of the immediate Cheshire, CT area.

The Neighborhoods:

Roaring Brook

Roaring Brook is a neighborhood in the South End of Cheshire. It borders Towpath, Sorghum Mill, and Bethany Mountain and has easy access to Routes 42, 10, and 70. The neighborhood is made up of several cul-de-sacs off of Mountain Road. The most well-known is Roaring Brook Road which terminates at base of Roaring Brook Falls Park.

Bethany Mountain

Located in the South end of Cheshire, Bethany Mountain by Route 42, which runs through the center of the neighborhood. The Route connects the neighborhood to Cheshire Village, Prospect and Bethany. There are several cul-de-sacs off of the main road with single family, residential homes.


The picturesque neighborhood of Mountaincrest is located within the city of Cheshire, Connecticut. Mountaincrest is made up of many stately, single family homes tucked away in the New England hardwoods. This grand area has an easy access to Route 42 and Cheshire Village and is bordered by neighboring Bethany Mountain, Mountain Brook, and Brooksvale. 

Mountain Brook

Mountain Brook is another area of grand stately homes. These beautiful single family homes are nestled in the New England hardwoods and are bordered by Mountaincrest, Brooksvale and Hamden. This neighborhood is made up of a main loop and many cul-de-sacs and easy access to Route 42 and 10.


Named for Thomas Brooks, the man who renamed the Western Farms as New Cheshire when they were incorporated as a village in 1723. The neighborhood is characterized by its large expanse of open space known as Brooksvale Farm Preserve. The area is made up of many historic homes with an unofficial historical society, as well as some newer homes. It is bordered by Avon, Mountain Brook, Mountaincrest, and Hamden. The neighborhood has easy access to Routes 42 and 10.


Towpath is a neighborhood in the South End of Cheshire. Its main road is Towpath Lane and has several cul-de-sacs extending from it. There is also Winding Trail Lane which extends from Towpath to Ward Lane. The neighborhood borders Brooksvale, Roaring Brook, Oak, and the Cheshire Linear Trail. The neighborhood has easy access to Routes 42 and 10 and the Cheshire Linear Trail.


Avon is a neighborhood in the South End of Cheshire characterized by its interconnected roads. The neighborhood is bordered by Brooksvale, Sharon, and Route 10. The neighborhood has easy access to Cheshire Village and Route 10.

Fresh Meadows

One of the earliest settlements in town, Cook Hill/Fresh Meadows is one of Cheshire most southern neighborhoods. Settled in 1694 by the “west farmers” of Wallingford who were looking for easily farmed land. The neighborhood still retains a rural atmosphere that the rich soil continues to support





Cheshire Schools

Do you have a family? You couldn't have picked a better place to raise your kids! The Cheshire Public School system is second to none! Rating 9 out 10, Cheshire has 3 Elementary Schools, 1 Junior High and 1 High School to serve your children:

Cheshire High School has consistently ranked as a Top 20 Connecticut High School by Niche Research. CHS serve approximately 1,500 students annually and their Teachers were also awarded with a Top 100 Teachers Award in 2015 as well!  Dodd Middle School has 786 students and has a great environment to cultivate reading, math, science and innovative learning techniques. Our elementary schools have also placed in the Top Elementary Schools in the U.S., according to Niche. Each of the elementary schools also have their own area's to highlight; Doolittle school, with an average enrollment of 517 students, is known for their high values in music, arts and physical education.  Highland Elementary, with an average enrollment of 827 students, is Cheshire's largest elementary school and is known for it's dedication to children with Special needs. Norton Elementary is known for it's incredible dedicated teachers to their students. With an average enrollment of 487 students, these young people are getting great individualized attention.

Other Places of interest in Cheshire, CT:

  • Cheshire Historical Society
  • Mattatuck Museum Arts & History Center
  • Lyman Orchards Golf Club
  • The Eli Whitney Museum
  • The Timex Museum
  • Sleeping Giant State Park
  • Castle View Balloons
  • Mount Southington Ski Area
  • Laurel View Country Club

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Contact Information

Sally A. Bowman Broker, Licensed in CT
Sally Bowman Real Estate, LLC
220 Old Towne Rd
Cheshire CT 06410
Phone: 203.272.2828
Cell 203.687.8026
Fax: 203.272.2702