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
Discover luxury living in this stunning 2122 SqFt Portman ELITE END UNIT in the prestigious Ridgewood community.
$560,000
Courtesy of Showcase Realty, Inc.
Stunning Luxury Townhome in the Desirable Ridgewood Community.
$600,000
Courtesy of Showcase Realty, Inc.
Priced to Sell ! Welcome to this rare new luxury home nestled in sought after Ridgewood community, perfectly situated on a cul de sac.
$629,999
Courtesy of Showcase Realty, Inc.
This bright and sunny home in the desirable 55 community of Benson Woods combines country living with modern convenience.
$590,000
Courtesy of Keller Williams Realty
An address that elevates your lifestyle Aberdeen Estates at Benson Woods is a premier 55 Adult Community located in the charming town of Middlebury.
$499,900
Courtesy of Century 21 AllPoints Realty
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$799,900
Courtesy of Real Estate Two
Enjoy a lifestyle of relaxed sophistication in this captivating home located in an adult community Age 55.
$625,000
Courtesy of RE/MAX Right Choice
Antique lovers alert ! Enjoy this quintessential 1803 Colonial on 1.
$649,000
Courtesy of Mary Helen Levine Real Estate LLC
Come see this immaculate Colonial in Brookside of Middlebury.
$674,900
Courtesy of Berkshire Hathaway NE Prop.
Purchasers default puts this great home back on market.
$529,900
Courtesy of Coldwell Banker Realty
Welcome to Middlebury's newest subdivision on Leonard Rd !
$899,900
Courtesy of William Raveis Real Estate
Welcome to 6 Brookside Drive, Middlebury, CT, a meticulously designed residence offering 3, 745 square feet of refined living space.
$719,000
Courtesy of Corcoran Centric Realty
Welcome home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$799,900
Courtesy of Real Estate Two
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$779,900
Courtesy of Real Estate Two
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$779,900
Courtesy of Real Estate Two
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
Enjoy living a relaxing and luxurious lifestyle in a most desirable community.
$515,000
Courtesy of BHGRE Bannon & Hebert
Welcome to our next phase !
$649,500
Courtesy of Real Estate Two
New construction designed to impress the most discerning buyer.
$899,000
Courtesy of BHGRE Bannon & Hebert
Come view this beautiful bright and spacious Colonial located on an interior lot in Middlebury, CT !
$824,900
Courtesy of William Raveis Real Estate
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