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.
Exciting opportunity to build your very own 2001 sqft ranch with wonderful curb appeal.
$829,000
Courtesy of Coldwell Banker Realty
Welcome to the scenic Blackberry Woods in Cheshire.
$910,000
Courtesy of Coldwell Banker Realty
Welcome to Blackberry Woods.
$987,000
Courtesy of Coldwell Banker Realty
Discover this beautifully updated ranch style home, offering modern comforts and stylish finishes throughout.
$409,900
Courtesy of eXp Realty
This 5 bedroom, 3 1 2 bath, beautifully designed home welcomes you in with all the features and updates that you crave inside and out.
$798,000
Courtesy of Real Broker CT, LLC
Have you been looking for new construction in a neighborhood setting ?
$869,000
Courtesy of Coldwell Banker Realty
Immaculate and well maintained Industrial Flex facility, offering high end finishes through out.
$1,500,000
Courtesy of Press/Cuozzo Realtors
Welcome to 365 Finch Ave, Cheshire, CT a truly exceptional property offering 4 spacious bedrooms and 3.
$919,900
Courtesy of eXp Realty
Nestled on 6. 5 serene acres next to the Fresh Meadows open space in Cheshire, CT, this worldclass property offers privacy, peace and elegance.
$1,400,000
Courtesy of The Greene Realty Group
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.
$939,000
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
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.
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 THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$573,570
Courtesy of EG Group Realty
Presenting an exquisite, one of a kind Modern Colonial Farmhouse that seamlessly combines elegance and functionality.
$1,175,000
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.
$701,050
Courtesy of EG Group Realty
Ready to move in Winter 2025.
$704,850
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.
Welcome to your own piece of heaven on Earth !
$2,200,000
Courtesy of Kelsey & Co. Real Estate
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