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
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
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
Come live your best life at 129 Periwinkle Dr.
$649,500
Courtesy of William Raveis Real Estate
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$759,900
Courtesy of Real Estate Two
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
Middlebury Modern. Authentic c.
$775,000
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 to 138 Skyline Dr, Middlebury, CT a beautifully maintained ranch style home with a finished basement and in law suite !
$649,900
Courtesy of RE/MAX One
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
Beautiful Portman Condo in Sought After Ridgewood Community.
$565,000
Courtesy of Showcase Realty, Inc.
Welcome to this stunning luxury end unit condo w 3 Bed, 2.
$575,000
Courtesy of Showcase Realty, Inc.
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 ...
$1,249,900
Courtesy of Coldwell Banker Realty
Discover luxury living in this stunning 2122 SqFt Portman ELITE END UNIT in the prestigious Ridgewood community.
$560,000
Courtesy of Showcase Realty, Inc.
Antique lovers alert ! Enjoy this quintessential 1803 Colonial on 1.
$649,000
Courtesy of Mary Helen Levine Real Estate LLC
Welcome to 6 Brookside Drive, Middlebury, CT, a meticulously designed residence offering 3, 745 square feet of refined living space.
$699,000
Courtesy of Corcoran Centric Realty
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$729,900
Courtesy of Real Estate Two
New construction designed to impress the most discerning buyer.
$899,000
Courtesy of BHGRE Bannon & Hebert
TO BE BUILT. One of the most desirable neighborhoods in Middlebury !
$899,000
Courtesy of BHGRE Bannon & Hebert
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