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.
$75,000
Courtesy of Collage Realty
AVAILABLE for acedemic yearFULLY FURNISHED.
$65,000
Courtesy of Collage Realty
ANY TIME AT THE BEACH ! !
$60,000
Courtesy of William Raveis Real Estate
ANY TIME AT THE BEACH ! !
$45,000
Courtesy of William Raveis Real Estate
Enjoy the summer at this well maintained Custom Colonial with a gorgeous pool, expansive covered patio, fabulous yard in the heart of Westport.
$25,000
Courtesy of Coldwell Banker Realty
Get away to it all... Sited on the town line between Fairfield and Westport, this stunning property features the best of all worlds.
$24,000
Courtesy of William Raveis Real Estate
Welcome to your Summer Oasis while you enjoy beautiful Sunrises, Sunsets and Water view's.
$18,000
Courtesy of William Raveis Real Estate
Welcome to your Summer Oasis while you enjoy beautiful Sunrises, Sunsets and Water view's.
$18,000
Courtesy of William Raveis Real Estate
Steps to miles of sandy beaches, breath taking water views, newly remodeled to perfection, and set on an oversized and level.
$13,500
Courtesy of William Raveis Real Estate
Fantastic furnished waterfront rental available for the 25 26 or 26 27 academic year.
$10,000
Courtesy of Brown Harris Stevens
ENJOY A TASTE OF BEACHFRONT LIVING !
$10,000
Courtesy of CRT Property Services, LLC
SUMMER RENTAL. AVAILABLE FOR JUNE ONLY !
$10,000
Courtesy of William Pitt Sotheby's Int'l
NEWLY REMOLDED HOME ON FAIRFIELD BEACH !
$10,000
Courtesy of CRT Property Services, LLC
The tranquil entrance features a stunning 18th century door, archway, and brick floor, setting the tone for a design masterpiece that blends modern amenities with historic elegance.
$8,900
Courtesy of BHHS Darien/New Canaan
LUXURY TOWNHOME ! It's all about location just minutes to the beach, town and train, gorgeous townhome with designer details and high end amenities !
$7,800
Courtesy of Keller Williams Realty
7, 000 for month of December only.
$7,000
Courtesy of William Raveis Real Estate
NEW CONSTRUCTION LUXURY RENTAL !
$7,000
Courtesy of Keller Williams Realty
Enjoy life in this two year young building in downtown Fairfield !
$6,650
Courtesy of Higgins Group Bedford Square
FURNISHED SUMMER RENTAL AVAILABLE JUNE 1 AUGUST 28.
$6,500
Courtesy of William Pitt Sotheby's Int'l
Introducing 1047 Reef Road, a desirable and sought after beach area rental that depicts coastal living.
$6,500
Courtesy of William Raveis Real Estate
Available Starting August 2025 This newly updated waterfront home is located directly on Samp Mortar Reservoir which is the charming centerpiece of the Lake Hills Community.
$6,500
Courtesy of Brown Harris Stevens
4 Bay garage in a prime location, close to highway and major retailers, great for a tire shop, mechanic's shop
$6,000
Courtesy of RE/MAX ONE
Welcome home to this spacious and bright University gem !
$6,000
Courtesy of Scott Kadison Real Estate
Enjoy life in this one year young building in downtown Fairfield !
$5,900
Courtesy of Higgins Group Bedford Square
Enjoy life in this one year young building in downtown Fairfield !
$5,900
Courtesy of Higgins Group Bedford Square
Fairfield Beach area rental with 3 bedrooms 2 full baths and only 2nd block from the beach 0.
$5,500
Courtesy of William Raveis Real Estate
Live two blocks from the beach in a charming two bedroom duplex apartment rental within larger home, located in the heart of The Village of Southport, CT.
$5,500
Courtesy of Coldwell Banker Realty
Enjoy life in this one year young building in downtown Fairfield !
$5,400
Courtesy of Higgins Group Bedford Square
This beautifully maintained 3 bedroom, 2.
$5,200
Courtesy of William Raveis Real Estate
Rent this beautiful 4 bedroom 3 bath lake front colonial.
$5,000
Courtesy of Coldwell Banker Realty
Custom, Like New Townhouse on quiet street close to all of Fairfield Amenities, highways and train station.
$5,200
Courtesy of Re/Max Right Choice
Welcome to this beautifully maintained single family home for rent, where comfort meets modern living.
$4,800
Courtesy of Five Stars Realty
Welcome to this charming Colonial nestled in the heart of downtown Fairfield.
$5,000
Courtesy of Higgins Group Real Estate
Welcome to your Summer Oasis while you enjoy beautiful Sunrises, Sunsets and Water view's.
$5,000
Courtesy of William Raveis Real Estate
Welcome to your Summer Oasis while you enjoy beautiful Sunrises, Sunsets and Water view's.
$5,000
Courtesy of William Raveis Real Estate
Welcome to your dream rental in the heart of Fairfield !
$5,000
Courtesy of Higgins Group Real Estate
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