Fairfield, located in the southwestern part of Connecticut, is a picturesque coastal town known for its historic charm and beautiful beaches. The town boasts numerous boutiques, art galleries, and restaurants, making it a popular destination for locals and visitors alike. Fairfield is also home to several top-rated hotels and luxurious residences, offering visitors a comfortable and lavish stay.

Best Choice of Shopping

  1. Fairfield Center: This charming shopping district features a variety of boutiques, jewelry stores, and art galleries, as well as upscale dining options.
  2. The Brick Walk: This outdoor shopping center features a mix of luxury retailers and fine dining options, including J. McLaughlin, Steven Alan, and Terrain Garden Café.
  3. Post Road Plaza: This shopping center is home to a variety of stores, including high-end retailers like Talbots, Chico's, and J. Crew.
  4. Fairfield University Bookstore: Located on the Fairfield University campus, this bookstore offers a unique selection of gifts, clothing, and books.
  5. The Village Green: This outdoor shopping area features a mix of local and national retailers, including Lululemon, Madewell, and Anthropologie.

Most Luxurious Hotels

  1. The Delamar Southport: This luxurious hotel features elegant guest rooms and suites, a full-service spa, and a gourmet restaurant.
  2. The Inn at Longshore: This waterfront hotel features spacious rooms and suites with stunning views of the Long Island Sound, as well as an on-site restaurant and bar.
  3. The Roger Sherman Inn: This historic inn features luxurious guest rooms and suites, a fine dining restaurant, and beautiful gardens.
  4. The Circle Hotel Fairfield: This boutique hotel features stylish guest rooms and suites, an on-site restaurant and bar, and easy access to Fairfield's downtown area.
  5. The Hi-Ho Motel: This retro-chic motel features fun, themed guest rooms and suites, a seasonal outdoor pool, and a lively bar and lounge.

Excellent Dining

  1. Artisan Restaurant: This farm-to-table restaurant features seasonal New American cuisine, craft cocktails, and a stylish dining room.
  2. Paci Restaurant: This cozy Italian restaurant features homemade pasta, fresh seafood, and an extensive wine list.
  3. The Whelk: This trendy seafood spot offers a menu of fresh, locally sourced seafood, oysters, and craft cocktails.
  4. The Chelsea: This waterfront restaurant and bar features stunning views of the Long Island Sound, as well as a menu of creative New American cuisine.
  5. The Gray Goose Café: This cozy café offers a menu of classic American fare, including burgers, sandwiches, and salads, as well as a great selection of craft beers and wines.

World Class Residence

  1. 1353 Pequot Avenue: This stunning waterfront estate features 8 bedrooms, 7 bathrooms, and breathtaking views of the Long Island Sound.
  2. 125 Sasco Hill Road: This elegant estate features 5 bedrooms, 5 bathrooms, and a private pool and tennis court.
  3. 233 Sasco Hill Road: This exquisite colonial-style home features 6 bedrooms, 7 bathrooms, and a pool house with a fireplace and wet bar.
  4. 2745 North Street: This sprawling estate features 7 bedrooms, 10 bathrooms, and a private pool and tennis court.
  5. 9 Willowmere Circle: This stunning lakefront home features 5 bedrooms, 6 bathrooms, and a private dock and boathouse.
Beach Area Colonial Walk To Beach.
$85,000
Courtesy of Collage Realty
This newly renovated, fully furnished home is available for rent for the month of August.
$23,000
Courtesy of Brown Harris Stevens
Beautifully renovated and refined, this elegant single family home is peacefully nestled in a private and tranquil section of Penfield Beach.
$20,000
Courtesy of Ogents, LLC
Experience the best of coastal living at 1016 Fairfield Beach Road, a quintessential beachside retreat perfectly positioned for an unforgettable summer.
$15,000
Courtesy of Compass Connecticut, LLC
Available for summer from June August 28th seasonal rental situated on direct creek waterfront, walk across street through private gate to beach Can be combined with 2142 Fairfield Beach Road.
$14,000
Courtesy of Collage Realty
STUNNING Rental steps from the Beach.
$13,000
Courtesy of Ogents, LLC
STUNNING Rental steps from the Beach.
$13,000
Courtesy of Ogents, LLC
STUNNING IMMACULATE Rental steps from the Beach.
$12,000
Courtesy of Ogents, LLC
FURNISHED ACADEMIC YEAR 2028 2029 AVAILABLE.
$11,500
Courtesy of William Raveis Real Estate
CURRENTLY RENTED THROUGH JULY ACADEMIC YEARS 2026, 2027 2028.
$9,850
Courtesy of William Raveis Real Estate
Summer, winter, short term or annual rental available.
$10,000
Courtesy of William Pitt Sotheby's Int'l
Bring the whole family ! This 5 bedroom home has everything you need for the perfect summer getaway.
$7,000
Courtesy of Century 21 AllPoints Realty
Available for Winter AY Rental August of 2027 June 2028.
$7,000
Courtesy of Brown Harris Stevens
Welcome to 1908 Stratfield Road !
$6,500
Courtesy of Coldwell Banker Realty
Enjoy the best of Fairfield living with this home's prime location close to both the beach and vibrant Fairfield Center !
$6,000
Courtesy of William Raveis Real Estate
Be the first to occupy this brand new townhome !
$5,800
Courtesy of ERA Insite Realty Services
Welcome to this beautifully maintained three bedroom, two full bath, one half bath home offering three levels of spacious living.
$4,500
Courtesy of William Raveis Real Estate
Charming and classic in town, two dwelling property with hardwood floors fireplace.
$4,950
Courtesy of RV3 Realty
Tucked away on a picturesque six acre estate between Fairfield and Westport, this restored vintage Carriage House offers a rare blend of privacy, charm, and modern convenience just minutes from ...
$5,000
Courtesy of Berkshire Hathaway NE Prop.
Welcome to 709 Tunxis Hill Road !
$4,300
Courtesy of Coldwell Banker Realty
Welcome to 131 Old Elm Road spacious off campus style living in a prime Fairfield location.
$4,750
Courtesy of Milas Realty Advisors
Beautiful and spacious townhome close to the center of Fairfield and all the amenities the town has to offer.
$4,500
Courtesy of William Raveis Real Estate
Ideally located in one of Fairfield's most walkable neighborhoods, this spacious and stylish townhome is just steps from the train, Whole Foods, a fitness center, and the scenic Ash Creek.
$4,100
Courtesy of Berkshire Hathaway NE Prop.
This spacious and bright 3 bedroom 2nd Floor apartment in 3 family home is ready for occupancy.
$4,356
Courtesy of Brown Harris Stevens
Beautifully designed and filled with natural light, this immaculate 3 story townhouse offers 2 3 bedrooms, 2 full and 1 half baths, soaring ceilings, and a spacious open floor plan ...
$4,200
Courtesy of Berkshire Hathaway NE Prop.
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