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
Stunning colonial style home situated on a beautifully landscaped acre lot on a serene cul de sac in a desirable south side location !
$689,900
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.
ALMOST FINISHED and ready for occupancy soon !
$1,295,000
Courtesy of William Raveis Real Estate
Nestled on a private, level corner lot in a peaceful cul de sac, this marvelous Colonial style home exudes charm and functionality.
$499,900
Courtesy of Berkshire Hathaway NE Prop.
Welcome to your Dream Home !
$1,299,000
Courtesy of William Raveis Real Estate
Available for a limited time.
$1,000,000
Courtesy of William Raveis Real Estate
DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles.
$469,900
Courtesy of EG Group Realty
Must See Updated Ready to move in Raised Ranch was fully remodeled in 2016 which included roof, windows, siding, electrical, plumbing, Forced Air Propane Furnace with Central Air, kitchen, bathrooms, ...
$499,988
Courtesy of Blue Lighthouse Realty, Inc
Spectacular move in ready South Cheshire two year young Contemporary Colonial.
$1,570,000
Courtesy of William Raveis Real Estate
Welcome to 454 Castle Glenn, Cheshire, CT an enchanting 2 story custom castle built in 1930, meticulously updated for 2024 while preserving its timeless elegance, seamlessly blending vintage charm with ...
$799,900
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.
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
PRICED TO SELL ! ! Welcome to Your Lovely New Home situated on a secluded 1.
$459,900
Courtesy of Parkview Properties LLC
Imagine hosting your holiday parties at this 7, 973 square foot Georgian Colonial that echoes luxury within two luminous acres.
$1,380,888
Courtesy of William Raveis Real Estate
Look no further for this one of a kind business opportunity.
$75,000
Courtesy of Laurel Crest Realty, LLC
Minutes to town, shops, dining Cheshire Academy, Quinnipiac and highways.
$469,900
Courtesy of William Raveis Real Estate
Welcome to 1000 Wolf Hill Road, this stunning contemporary ranch home will not disappoint !
$369,000
Courtesy of eXp Realty
This Custom built 2876 SF 4 bed 4 bath Colonial with impressive brick front offers an open distinctive floor plan.
$689,000
Courtesy of Beycome of Connecticut
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
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
Move in December 2023 ! DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location, to its variety of home styles, and EG Home s quality and experience, The Reserve at ...
$520,280
Courtesy of EG Group Realty
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
Three bedroom three and a half bath colonial in South Cheshire.
$499,000
Courtesy of Skyview Realty LLC
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
Courtesy of Coldwell Banker Realty
This home is located in one of the most desirable sections of Cheshire, the Mount Sanford area.
$499,888
Courtesy of William Raveis Real Estate
Available in the Summer of 2024.
$579,900
Courtesy of EG Group Realty
Nestled within a tranquil suburban neighborhood, this deceivingly spacious updated split level home beckons with its unassuming exterior.
$450,000
Courtesy of RE/MAX RISE
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