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.
They are not making more land !
$2,800,000
Courtesy of Evjen Agency
Located in highly sought after south Cheshire, this stunning estate sits on nearly 3 private acres and offers an ideal combination of space, privacy, comfort.
$699,900
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 your dream home.
$548,000
Courtesy of William Raveis Real Estate
Welcome to Cheshire ! This 3 bedroom, 2 bathroom house is cozy and full of charm.
$499,900
Courtesy of RE/MAX ONE
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
Welcome to your Dream Home !
$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
NEW IMPROVEMENTS not pictured Freshly painted entry and stairway hall, living room, family room, bedroom over garage, primary bedroom and primary bathroom Nestled on a private, level corner lot in ...
$499,900
Courtesy of Berkshire Hathaway NE Prop.
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
Yes, we know, you always wanted to move to Cheshire but could not find the right place.
$499,900
Courtesy of Executive Real Estate Inc.
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.
$499,990
Courtesy of EG Group Realty
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$558,685
Courtesy of EG Group Realty
Discover the perfect blend of functionality and prime location with this exceptional commercial property situated on over an acre of land on bustling Route 10 in Cheshire, CT.
$695,000
Courtesy of Advise Realty Services
Desirable Cheshire Crossing 55 Community built in 2008.
$519,900
Courtesy of Coldwell Banker Premier Real Estate
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.
Seller installing new septic !
$589,900
Courtesy of Calcagni Real Estate
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
Welcome to this well maintained bright single family home in a beautiful neighborhood.
$575,000
Courtesy of Coldwell Banker Realty
Now here's one of the kind take your breath away, completely custom built, 'Modern Colonial Farmhouse' with a brilliant open concept floor plan and top of the line trip package.
$1,300,000
Courtesy of Blue Lighthouse Realty, Inc
Look no further for this one of a kind business opportunity.
$75,000
Courtesy of Laurel Crest Realty, LLC
Builder is Offering a Mortgage Rate Buydown if Under Contract by 1 10 24 !
$854,000
Courtesy of Coldwell Banker Realty
Move Right Into This Bright and Open 3 Bedroom, 1.
$409,000
Courtesy of Coldwell Banker Realty
Stop, look, listen, Sitting on 4.
$1,200,000
Courtesy of Coldwell Banker Realty
What a beautiful Cape Home located on a little over 1 2 acre.
$379,900
Courtesy of Calcagni Real Estate
Inquire immediately ask your agent for a walkthrough video and lock this property up now.
$425,000
Courtesy of Keller Williams Realty Prtnrs.
Nestled in a quiet, no drive through area on 1.
$599,000
Courtesy of Showcase Realty, Inc.
Lovely 3 Bedroom Cape with Gleaming Hardwood Floors !
$289,900
Courtesy of Century 21 AllPoints Realty
Still time to choose your finishes !
$989,900
Courtesy of Century 21 AllPoints Realty
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