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.
Welcome to Hickory Hill Orchards, a stunning New England property in Cheshire, CT, featuring a charming 4143 square feet farmhouse nestled in approximately 33 beautiful acres of orchards and woodlands.
$3,500,000
Welcome to Hickory Hill Orchards, a stunning New England property in Cheshire, CT, featuring a charming 4143 square feet farmhouse nestled in approximately 33 beautiful acres of orchards and woodlands.
$3,500,000
Welcome home to 323 Patton Drive in Cheshire, CT !
$435,000
Set on a quiet street in South Cheshire, 1243 Avon Blvd.
$419,900
Introducing Pond's Edge, a planned unit development of 6 exquisite waterfront and water view homes.
$1,129,900
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$454,900
Ready to move in Winter 2025.
$619,900
Look no further ! This lovingly and impeccably maintained 4 Bedroom, 3 Bath Colonial in a sought after Honeypot Glen neighborhood is ready for you !
$519,900
Welcome to 2 Tumblebrook Place at Copper Hill !
$574,900
Nestled on a tranquil cul de sac in the Deaconwood neighborhood of South Cheshire, 190 Nutmeg Pl offers a serene escape.
$630,000
Opportunity awaits at this turnkey 3 unit multifamily with water views of Mixville Lake for both owner occupants or investors and less than a minute walk to Mixville Park.
$499,000
Stately colonial home to be built in this affluent area of Cheshire.
$989,000
Great central CT location, 25 min from Yale downtown New Haven, 35 from Hartford, in a cul de sac w the best of town conveniences country feel.
$485,500
Welcome to this stunning rebuilt in 2024 house that boasts four bedrooms, and three full bathrooms.
$600,000
Welcome to a timeless recently remodeled masterpiece of Tudor design by renowned architect Carina Mortimer.
$795,000
This Beautifully Appointed 4 Bedroom, 2 Bath Cape Style Home Is Ready For You !
$575,000
WHY BUILD ! This completely newly updated Salt Box style home is proudly perched on a corner lot in a great location of Cheshire, CT !
$449,900
Your Cheshire home awaits you !
$649,900
WOW.... House like this one is not available too often.
$1,300,000
This location was once used as a bank site and office space for an insurance company.
$950,000
Gorgeous colonial with inviting front porch and an abundance of privacy.
$789,990
LOCATION ! Welcome to Col home nestled in a prime neighborhood, offering 4 bedr and 2.
$599,900
Welcome to your next business venture !
$875,000
Amazing Opportunity to lease this Prime Route 10 Cheshire location.
$975,000
Available in the Winter of 2024.
$634,225
Welcome to Pond's Edge, a planned unit development of 6 exquisite waterfront and water view homes.
$1,025,900
Available in the Fall of 2024.
$672,275
Welcome home to your 4 bedroom, 2.
$639,000
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$523,275
Generate monthly rental income !
$649,900
Prepare to fall in love with this TO BE BUILT Modern Farmhouse style plan proposed for 8 Melrose Drive !
$1,135,000
Quick move in Carriage home complete with designer appointed finishes !
$803,705
Three bedroom three and a half bath colonial in South Cheshire.
$499,000
Lovely 3 Bedroom Cape with Gleaming Hardwood Floors !
$289,900
This home is located in one of the most desirable sections of Cheshire, the Mount Sanford area.
$499,888
Move right into this fully updated and graciously remodeled Alice Washburn home set on a professionally landscaped picturesque sprinklered lot in the heart of Cheshire.
$749,900
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