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.
Private Cape Estate on 6.
$860,000
Courtesy of Coldwell Banker Realty
Welcome to 454 Castle Glenn Cheshire's storybook stone castle with timeless charm and smart modern updates, nestled near the center of town on a private, tree lined lot.
$789,900
Courtesy of Berkshire Hathaway NE Prop.
Spacious and grand contemporary colonial on a spectacular level one acre lot in a desirable, well regarded neighborhood.
$760,000
Courtesy of Calcagni Real Estate
Who will be the first to find 259 and begin their new life in this perfect home.
$525,000
Courtesy of Century 21 AllPoints Realty
Welcome to this charming Colonial nestled on a flat half acre lot in the heart of Cheshire.
$499,000
Courtesy of Calcagni Real Estate
Welcome to 689 S Meriden Rd, This stunning 4 bedrooms and 2 bathrooms colonial is located on Tranquille neighborhood.
$649,000
Courtesy of Eagle Eye Realty PLLC
Charming Ranch style home offering 3 bedrooms and 1 1 2 baths, including a convenient half bath in the primary bedroom.
$485,000
Courtesy of Berkshire Hathaway NE Prop.
Inspiring country home. Inground pool, tennis court and equestrian features.
$1,759,900
Courtesy of Divine Realty, LLC
Welcome to Blackberry Woods.
$987,000
Courtesy of Coldwell Banker Realty
Welcome to Blackberry Woods, Cheshire's newest neighborhood !
$1,299,000
Courtesy of New England Prestige Realty
Architect designed newer Dutch colonial situated on almost 4 acres in the estate area of South Cheshire.
$996,000
Courtesy of William Raveis Real Estate
You will love this address in the south end of Cheshire.
$929,000
Courtesy of Botti Realty
Build Your Dream Home at The Reserve at Stonebridge Crossing !
$669,900
Courtesy of EG Group Realty
Prime Commercial Property for Sale High Traffic Location !
$1,390,000
Courtesy of Lamacchia Realty
Welcome to Blackberry Woods, Cheshire's newest development.
$1,060,000
Courtesy of Coldwell Banker Realty
Wonderful opportunity to build in the south end of Cheshire.
$950,000
Courtesy of Coldwell Banker Realty
Exciting opportunity to build your very own 2001 sqft ranch with wonderful curb appeal.
$799,000
Courtesy of Coldwell Banker Realty
Wonderful opportunity to build in the south end of Cheshire.
$859,000
Courtesy of Coldwell Banker Realty
Welcome to the scenic Blackberry Woods in Cheshire.
$910,000
Courtesy of Coldwell Banker Realty
Exciting opportunity to build your very own 2001 sqft ranch with wonderful curb appeal.
$829,000
Courtesy of Coldwell Banker Realty
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
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
Presenting 15 Melrose Drive !
$1,299,000
Courtesy of William Raveis Real Estate
Carriage home complete with designer appointed finishes !
$814,735
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.
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.
Major price drop ! ! This property was once used as a potato farm.
$1,999,000
Courtesy of Evjen Agency
Welcome to your own piece of heaven on Earth !
$2,200,000
Courtesy of Kelsey & Co. Real Estate
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