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
Immerse yourself in the laid back lifestyle of Tylers Cove community, nestled beside the picturesque Lake Quassapaug.
$899,900
CHOICE LOCATION WITH GORGEOUS VIEWS !
$699,900
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$779,900
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$699,000
Come enjoy a unique, elegant, old world experience designed with artful accents and architectural accentuations throughout.
$1,500,000
Back on Market. Buyer got cold feet and backed out.
$469,000
Come view this beautiful bright and spacious Colonial located on an interior lot in Middlebury, CT !
$895,900
New construction designed to impress the most discerning buyer.
$875,000
Welcome to Christian Road in Middlebury.
$419,000
Welcome to your new home in beautiful historic Middlebury CT.
$530,000
REDUCED ! ! Ultimate privacy in this 8 room, 4 bedroom, 4098 SF Middlebury colonial with a contemporary flair set on a 4.
$749,900
Custom built home on a 1.
$925,000
Welcome to our next phase !
$649,500
Welcome to our next phase !
$665,600
TURN THE KEY AND START COUNTING YOUR RETURNS WHEN YOU ARE THE OWNER OF MIDDLEBURY'S FAVORITE FAMILY RESTAURANT DESTINATION !
$839,500
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$774,900
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$674,900
Welcome Home to Middlebury's newest 23 lot subdivision Hunting Ridge Estates.
$779,900
Welcome to our next phase !
$660,500
Welcome to our next phase !
$655,500
You Will Find At The Top of the Hill a Private Hideaway This 5 level split has a cozy place for each member to cuddle up with a good book.
$375,000
Quick delivery Simsbury Elite with loads of upgrades in Phase 1 !
$629,000
A remarkable opportunity awaits you at 275 Burr Hall Road, Middlebury.
$825,000
Imagine being right outside your front door, and only hearing the birds chirping or trees dancing in the wind.
$684,900
Do not miss this lovely 2 BR cape in desirable Steeplechase.
$499,000
Do not miss this lovely 2 BR cape in desirable Steeplechase.
$499,000
Gorgeous Brookside Colonial !
$575,000
EXCEPTIONAL ! This magnificent 6 bedroom, 4.
$1,995,000
Elegance and stunning curb appeal will pull you into this well maintained colonial home, tucked away in a level, walkable neighborhood.
$589,000
Gorgeous Brookside Colonial !
$575,000
New construction designed to impress the most discerning buyer.
$850,000
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