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.
short term furnished flexable terms furnished WATERFRONT DUPLEX.
$80,000
Courtesy of Collage Realty
Beach Area Colonial Walk To Beach.
$80,000
Courtesy of Collage Realty
A Coastal Sanctuary Like No Other Welcome to a breathtaking direct waterfront estate, where every detail has been thoughtfully designed for extraordinary coastal living.
$50,000
Courtesy of William Raveis Real Estate
ANY TIME AT THE BEACH ! !
$60,000
Courtesy of William Raveis Real Estate
AVAILABLE JUNE 1, 2025. RENOVATED and ELEGANT Single home peacefully settled in a very private, tranquil and family section of the Penfield Beach.
$20,000
Courtesy of Preoh, LLC
15K month for term lease.
$15,000
Courtesy of Derek Greene
FURNISHED SUMMER RENTAL. Renovated 5 Bedrooms, 2 full baths Home on a Private Large 0.
$15,000
Courtesy of Preoh, LLC
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
Welcome to Fairfield Beach, available as a student rental from September 1, 2025, to May 21, 2026.
$11,000
Courtesy of Higgins Group Real Estate
Introducing a captivating haven of luxury and comfort a magnificent 3126 sqft.
$10,000
Courtesy of Blue Lighthouse Realty, Inc
STUNNING IMMACULATE Rental steps from the Beach.
$10,000
Courtesy of Preoh, LLC
Coastal Home in Prime Fairfield Beach Town Location Walk to Shops and Train !
$9,950
Courtesy of Keller Williams Realty
STUNNING IMMACULATE Rental steps from the Beach.
$9,500
Courtesy of Preoh, LLC
Stunning Modern Retreat Summer Furnished Home for lease.
$8,800
Courtesy of William Raveis Real Estate
Embrace the ultimate in sophistication and style with this stunning two bedroom, twobath apartment, located in the heart of Downtown Fairfield.
$7,500
Courtesy of Coldwell Banker Realty
Weekly Summer Rental 6 Nights, 7 Days.
$7,500
Courtesy of CRT Property Services, LLC
NEW CONSTRUCTION LUXURY RENTAL !
$7,000
Courtesy of Keller Williams Realty
Academic Year Rental for 2025 2026 ONLY.
$6,500
Courtesy of William Raveis Real Estate
Welcome to Bronson House, Greenfield Hill's best new luxury rental opportunity !
$6,495
Courtesy of Berkshire Hathaway NE Prop.
Enjoy life in this two year young building in downtown Fairfield !
$6,650
Courtesy of Higgins Group Bedford Square
Introducing 1047 Reef Road, a desirable and sought after beach area rental that depicts coastal living.
$6,500
Courtesy of William Raveis Real Estate
Welcome to your dream beach getaway !
$6,000
Courtesy of Compass Connecticut, LLC
Welcome home to this spacious and bright University gem !
$6,000
Courtesy of Scott Kadison Real Estate
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
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
Custom, Like New Townhouse on quiet street close to all of Fairfield Amenities, highways and train station.
$5,500
Courtesy of RE/MAX Right Choice
SUMMER RENTAL ACADEMIC HAS GONE MASSIVE RENOVATION AND IS STUNNING !
$5,500
Courtesy of The Brokerage of New England
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
Welcome to 366 Suburban Avenue, a beautifully updated Colonial nestled in a prime Fairfield location.
$5,000
Courtesy of Higgins Group Real Estate
3 Bedroom, 2 Bath, Cape With Open Floor Plan, Eat In Kitchen And Family Room With French Door Sliders To Back Deck And Fenced in Yard, Newer Heating, Central AC, ...
$5,000
Courtesy of Berkshire Hathaway NE Prop.
A 2 3 Bedroom, Jewel of a Beach house, situated in a prime location just 2 doors from Jennings Beach and South Benson Marina.
$5,000
Courtesy of William Raveis Real Estate
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 charming Colonial nestled in the heart of downtown Fairfield.
$5,000
Courtesy of Higgins Group Real Estate
Welcome to your dream rental in the heart of Fairfield !
$5,000
Courtesy of Higgins Group Real Estate
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