Cheshire is a picturesque and affluent town in Connecticut, known for its beautiful homes, charming downtown area, and excellent schools. The town is located just a short drive from New Haven and Hartford, offering easy access to shopping, dining, and entertainment.

Best Choice of Shopping

  1. The Shops at Somerset Square: This open-air shopping center features a variety of upscale retailers, including Anthropologie, Lululemon, and Pottery Barn.
  2. Westfarms Mall: Located just a short drive from Cheshire, this premier shopping destination offers a mix of luxury and high-end retailers, including Nordstrom, Louis Vuitton, and Gucci.
  3. Clinton Crossing Premium Outlets: For those seeking designer deals, this outlet mall is a must-visit, with brands like Michael Kors, Kate Spade, and Coach.
  4. The Promenade Shops at Evergreen Walk: This outdoor shopping center in nearby South Windsor offers a range of luxury and specialty retailers, including Williams-Sonoma, J.Crew, and Brooks Brothers.
  5. Blue Back Square: Located in nearby West Hartford, this upscale shopping district features a mix of local boutiques and national retailers, as well as a movie theater and several restaurants.

Most Luxurious Hotels

  1. The Delamar West Hartford: This elegant boutique hotel features luxurious accommodations, a full-service spa, and an award-winning restaurant.
  2. The Study at Yale: Located in nearby New Haven, this chic hotel offers sophisticated accommodations, a rooftop bar, and easy access to Yale University and downtown New Haven.
  3. Saybrook Point Resort & Marina: This waterfront resort in nearby Old Saybrook offers luxurious accommodations, a full-service spa, and a range of recreational activities.
  4. The Mayflower Inn & Spa: Located in nearby Washington, CT, this luxurious hotel features a world-class spa, elegant accommodations, and an award-winning restaurant.
  5. The Griswold Inn: This historic inn, located in nearby Essex, CT, offers charming accommodations, fine dining, and live music in its cozy tavern.

Excellent Dining

  1. The Farmhouse Restaurant: This farm-to-table restaurant in nearby Newtown offers creative New American cuisine and an extensive wine list.
  2. Union League Cafe: Located in downtown New Haven, this upscale French brasserie offers classic dishes like escargot, steak frites, and bouillabaisse.
  3. Present Company: This chic restaurant in downtown Simsbury offers a modern take on American cuisine, with dishes like pork belly bao buns and truffle fries.
  4. ON20: Located on the 20th floor of a downtown Hartford skyscraper, this elegant restaurant offers stunning views of the city and a sophisticated menu of New American cuisine.
  5. The Whelk: Located in nearby Westport, this seafood-focused restaurant offers fresh, locally sourced dishes like razor clam crudo, grilled octopus, and lobster spaghetti.

World Class Residences

  1. space, with six bedrooms, eight full bathrooms, and two half-bathrooms. The property sits on over five acres of land, offering complete privacy and tranquility. It also includes a pool, a tennis court, a home theater, and a wine cellar.
  2. 1785 Cheshire Street: This breathtaking property sits on over 13 acres of land, featuring a main house with six bedrooms and six full bathrooms, as well as a separate guesthouse with two bedrooms and two full bathrooms. The property includes a pool, a tennis court, a pond, and a four-car garage.
  3. 2221 Cheshire Road: This elegant estate offers over 8,000 square feet of living space, with five bedrooms, six full bathrooms, and two half-bathrooms. The property sits on over four acres of land, featuring a pool, a tennis court, a hot tub, and a three-car garage.
  4. 205 Boulder Road: This spectacular property sits on over 19 acres of land, featuring a main house with four bedrooms and four full bathrooms, as well as a separate guesthouse with two bedrooms and two full bathrooms. The property includes a pool, a tennis court, a pond, and a four-car garage.
  5. 1149 Cheshire Street: This magnificent estate offers over 10,000 square feet of living space, with six bedrooms, six full bathrooms, and two half-bathrooms. The property sits on over three acres of land, featuring a pool, a tennis court, a home theater, and a wine cellar. It also includes a separate guesthouse with two bedrooms and two full bathrooms.
Make your appointment today to view this great Colonial 2 family home with 4 bed, 3 bath, 2, 313 sq ft.
$489,000
Courtesy of Dorrance Realty
Don't miss this beautiful Cheshire home that's been renovated and refreshed while still preserving its charm !
$470,000
Courtesy of Berkshire Hathaway NE Prop.
Nestled on 6. 5 serene acres next to the Fresh Meadows open space in Cheshire, CT, this worldclass property offers privacy, peace and elegance.
$1,750,000
Courtesy of The Greene Realty Group
This impeccably maintained 4 bedroom, 2.
$790,000
Courtesy of Dow Della Valle
A very special custom built ten room Colonial with a brick veneer front, an open porch that is in the Woodland subdivision in the Nob Hill neighborhood of Cheshire and ...
$679,000
Courtesy of Marty Rauch Real Estate
Welcome to 365 Finch Ave, Cheshire, CT a truly exceptional property offering 4 spacious bedrooms and 3.
$925,000
Courtesy of eXp Realty
Wow best location, best outdoor patio for 60, best casual food, best cocktails, best fireplace, landmark oldest restaurant in Cheshire Victorian architecture building circa 1900.
$1,195,000
Courtesy of Agnelli Real Estate
350 South Main Street is an attractive office building located in the center of Cheshire that is available for both sale and lease.
$899,000
Courtesy of Calcagni Real Estate
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$464,900
Courtesy of EG Group Realty
Welcome to Pond's Edge, a planned unit development of 6 exquisite waterfront and water view homes.
$1,025,900
Courtesy of Berkshire Hathaway NE Prop.
Welcome to 1211 Summit Rd.
$410,000
Courtesy of Calcagni Real Estate
Presenting 15 Melrose Drive !
$1,299,000
Courtesy of William Raveis Real Estate
Have you been searching for a new construction home that will provide you with one level living ?
$1,120,000
Courtesy of William Raveis Real Estate
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$558,685
Courtesy of EG Group Realty
Welcome to this spacious 8 room, multifunctional ranch, featuring 3 bedrooms and perfectly designed for a home based office or business.
$449,900
Courtesy of Barrieau Realty Signature Prop
Carriage home complete with designer appointed finishes !
$804,735
Courtesy of EG Group Realty
Discover versatile, modern living at 158 Willow St in Cheshire.
$589,900
Courtesy of Dave Jones Realty, LLC
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$499,990
Courtesy of EG Group Realty
Presenting an exquisite, one of a kind Modern Colonial Farmhouse that seamlessly combines elegance and functionality.
$1,200,000
Courtesy of Berkshire Hathaway NE Prop.
Major price drop ! ! This property was once used as a potato farm.
$1,999,000
Courtesy of Evjen Agency
Available in the Winter of 2024.
$735,400
Courtesy of EG Group Realty
Introducing Pond's Edge, a planned unit development of 6 exquisite waterfront and water view homes.
$1,129,900
Courtesy of Berkshire Hathaway NE Prop.
Ready to move in Winter 2025.
$739,200
Courtesy of EG Group Realty
Welcome to your own piece of heaven on Earth !
$2,200,000
Courtesy of Kelsey & Co. Real Estate
Available in the Fall of 2024.
$719,400
Courtesy of EG Group Realty
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