Middlebury, Connecticut is a charming and affluent town located in the western part of the state. It is home to scenic parks, quaint farms, and beautiful historic buildings. Middlebury is a great place to live for those who enjoy a quiet and peaceful lifestyle, while still being close to major cities like New York and Boston.

Best choice of shopping

  1. The Shops at Yale - This upscale shopping center features a variety of high-end fashion brands, jewelry stores, and specialty shops.
  2. Westfield Trumbull - Located just a short drive from Middlebury, this mall features luxury brands like Burberry, Louis Vuitton, and Gucci.
  3. Danbury Fair Mall - This shopping center boasts over 200 stores, including luxury brands like Michael Kors and Swarovski.
  4. Clinton Crossing Premium Outlets - This outdoor shopping center is home to over 70 designer and brand-name outlet stores, offering shoppers discounts of up to 65%.
  5. The Promenade Shops at Evergreen Walk - Located in nearby South Windsor, this open-air shopping center features upscale retailers like Brooks Brothers, Kate Spade, and J.Crew.

Most luxurious hotels

  1. The Mayflower Grace - This historic hotel offers elegant accommodations, a luxurious spa, and fine dining at its award-winning restaurant.
  2. Delamar Southport - This boutique hotel boasts a prime waterfront location, spacious guest rooms, and a full-service spa.
  3. Saybrook Point Resort & Marina - Located in nearby Old Saybrook, this resort offers upscale accommodations, fine dining, and a full-service spa.
  4. The Inn at Stonington - This charming inn offers luxurious rooms with views of the harbor, as well as a cozy library and a gourmet breakfast.
  5. The Study at Yale - This upscale hotel is located in the heart of Yale University's campus and features stylish accommodations and a popular restaurant.

Excellent Dining

  1. Union League Cafe - This French brasserie offers classic dishes like escargots, bouillabaisse, and beef Wellington in an elegant setting.
  2. Osteria Romana - This upscale Italian restaurant serves homemade pasta, fresh seafood, and authentic Roman dishes in a cozy and intimate atmosphere.
  3. Barcelona Wine Bar - This trendy restaurant offers a variety of Spanish-inspired small plates, as well as an extensive wine list.
  4. Roia Restaurant & Cafe - Located in nearby New Haven, this Italian restaurant features upscale cuisine made with local and seasonal ingredients.
  5. The Capital Grille - This steakhouse chain offers prime cuts of beef, fresh seafood, and an extensive wine list in a sophisticated setting.

World class Residences

  1. The Estates at Sherwood - This gated community features large and luxurious homes set on expansive lots, offering privacy and tranquility.
  2. Ridgewood at Middlebury - This upscale development features spacious homes with high-end finishes, located
  3. Hillcrest luxury apartments
  4. The residences at Quarry Walk
Beautifully maintained by its original owners, this stunning home offers a peaceful retreat with thoughtful design throughout.
$599,000
Courtesy of BHGRE Bannon & Hebert
Wow this is it ! The original model home is back on the market for the first time, offering exceptional quality and design.
$680,000
Courtesy of Drakeley Real Estate, Inc.
Luxury living in this stunning 2122 SqFt Portman ELITE END unit in sought Ridgewood community.
$560,000
Courtesy of Serhant Connecticut, LLC
Exceptional Craftsmanship Refined Luxury.
$629,000
Courtesy of Dave Jones Realty, LLC
Welcome to Benson Woods an exclusive community of 78 single family homes designed for active adults.
$569,900
Courtesy of BHGRE Bannon & Hebert
Welcome to this luxury end unit condo built in 2022 w 3 Bed, 2.
$575,000
Courtesy of Serhant Connecticut, LLC
Beautiful Portman Condo in Sought After Ridgewood Community.
$565,000
Courtesy of Serhant Connecticut, LLC
Don't wait to see this turn key home in the desirable Ridgewood of Middlbury, one of the areas newest and most picturesque communities.
$659,000
Courtesy of Berkshire Hathaway NE Prop.
Welcome to Granite Woods 2024 HOBI Award Winner for Best Detached 55 Community.
$721,000
Courtesy of Michaud Real Estate
Middlebury Modern. Authentic c.
$749,000
Courtesy of Klemm Real Estate Inc
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$759,900
Courtesy of Real Estate Two
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$759,900
Courtesy of Real Estate Two
Welcome to Granite Woods 2024 HOBI Award Winner for Best Detached 55 Community.
$619,000
Courtesy of Michaud Real Estate
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$759,900
Courtesy of Real Estate Two
Welcome to 138 Skyline Dr, Middlebury, CT a beautifully maintained ranch style home with a finished basement and in law suite !
$615,000
Courtesy of RE/MAX One
Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more.
$639,000
Courtesy of BHGRE Bannon & Hebert
Welcome to 28 Maple Drive, a classic gem in the heart of Middlebury, Connecticut, where charm and comfort meet timeless design.
$525,000
Courtesy of William Raveis Real Estate
Sitting pretty at 4, 200 square feet, this exquisite property is designed for those ready to embrace a luxury lifestyle, offering the perfect setting for anyone looking to expand their ...
$1,219,900
Courtesy of Coldwell Banker Realty
Antique lovers alert ! Enjoy this quintessential 1803 Colonial on 1.
$599,000
Courtesy of Mary Helen Levine Real Estate LLC
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$729,900
Courtesy of Real Estate Two
TO BE BUILT. One of the most desirable neighborhoods in Middlebury !
$899,000
Courtesy of BHGRE Bannon & Hebert
New construction designed to impress the most discerning buyer.
$899,000
Courtesy of BHGRE Bannon & Hebert
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