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
Custom built by Harlamon Homes this newly constructed colonial is unsurpassed in quality, detail, and craftsmanship with every imaginable amenity, too many to list !
$689,000
Courtesy of Realty Group of New England, LLC
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
An address that elevates your lifestyle Aberdeen Estates at Benson Woods is a premier 55 Adult Community located in the charming town of Middlebury.
$509,900
Courtesy of Century 21 AllPoints Realty
Benson Woods is the perfect place for active adults seeking a serene and carefree lifestyle.
$599,900
Courtesy of BHGRE Bannon & Hebert
Leave your mower, shovel and hedge clippers behind.
$689,000
Courtesy of William Raveis Real Estate
Great New Price ! Discover the perfect blend of timeless charm and serene natural beauty in this elegant colonial home, set on a private 2.
$559,900
Courtesy of Calcagni Real Estate
Antique lovers alert ! Enjoy this quintessential 1803 Colonial on 1.
$699,000
Courtesy of Mary Helen Levine Real Estate LLC
PRICE REDUCED Fabulous Home with a legal in law apartment, in an ideal commuter location boasts a 4 Bedroom, 3 Bath open plan with hardwood floors, walls of windows, 2 ...
$529,900
Courtesy of Coldwell Banker Realty
Move right into this expansive well appointed home completed in 2013 of Benson Woods development.
$545,000
Courtesy of Litchfield Hills Properties LLC
Welcome to Middlebury's newest subdivision on Leonard Rd !
$899,900
Courtesy of William Raveis Real Estate
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
This sprawling cape sits majestically on nearly an acre of property on Carriage Drive, one of Middlebury's most desirable neighborhoods.
$510,000
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
Come view this beautiful bright and spacious Colonial located on an interior lot in Middlebury, CT !
$849,900
Courtesy of William Raveis Real Estate
House has 4 bedroom 3 full baths.
$649,999
Courtesy of Continental Real Estate
Welcome to 6 Brookside Drive, Middlebury, CT, a meticulously designed residence offering 3, 745 square feet of refined living space.
$725,000
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
You can spend every day on vacation.
$875,000
Courtesy of BHGRE Bannon & Hebert
Rare Middlebury opportunity to purchase over 17 acres of an approved subdivision, lots 1 5 of Trout Estates.
$499,900
Courtesy of Showcase Realty, Inc.
TO BE BUILT. One of the most desirable neighborhoods in Middlebury !
$899,000
Courtesy of BHGRE Bannon & Hebert
You can spend every day on vacation.
$875,000
Courtesy of BHGRE Bannon & Hebert
Gorgeous Brookside Colonial !
$575,000
Courtesy of Showcase Realty, Inc.
Gorgeous Brookside Colonial !
$575,000
Courtesy of Showcase Realty, Inc.
EXCEPTIONAL ! This magnificent 6 bedroom, 4.
$1,995,000
Courtesy of Eagle Eye Realty PLLC
A remarkable opportunity awaits you at 275 Burr Hall Road, Middlebury.
$825,000
Courtesy of BHGRE Bannon & Hebert
Quick delivery Simsbury Elite with loads of upgrades in Phase 1 !
$629,000
Courtesy of Real Estate Two
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
Courtesy of Coldwell Banker Realty
Elegance and stunning curb appeal will pull you into this well maintained colonial home, tucked away in a level, walkable neighborhood.
$589,000
Courtesy of BHGRE Bannon & Hebert
New construction designed to impress the most discerning buyer.
$850,000
Courtesy of BHGRE Bannon & Hebert
Do not miss this lovely 2 BR cape in desirable Steeplechase.
$499,000
Courtesy of BHGRE Bannon & Hebert
New construction designed to impress the most discerning buyer.
$899,000
Courtesy of BHGRE Bannon & Hebert
Do not miss this lovely 2 BR cape in desirable Steeplechase.
$499,000
Courtesy of BHGRE Bannon & Hebert
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