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.
$80,000
Courtesy of Collage Realty
short term furnished flexable terms furnished WATERFRONT DUPLEX.
$80,000
Courtesy of Collage Realty
AVAILABLE FOR ACADEMIC YEAR SEPTEMBER MAY.
$80,000
Courtesy of Collage Realty
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
Surrounded by stone walls, this one of a kind, spectacular and private 36 acre Greenfield Hill country compound has had a stunning top level transformation, creating a breathtaking Fairfield County ...
$39,000
Courtesy of William Pitt Sotheby's Int'l
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
Live at the beach ! Welcome to 2123, a spectacular beach front home w a separate dwelling on the creek side.
$16,500
Courtesy of William Raveis Real Estate
Indulge in breathtaking views stretching all the way to New York from this remarkable abode !
$16,000
Courtesy of William Raveis Real Estate
Unique rental opportunity beautifully renovated contemporary classic, long private driveway lighted with scenic pond as you enter, stocked with fish and turtle and frequented by wildlife.
$15,000
Courtesy of The Greene Realty Group
Enjoy living in this expanded renovated modern farmhouse, newly painted and elegantly decorated with a sunny open floor plan.
$15,000
Courtesy of William Pitt Sotheby's Int'l
Wonderful annual furnished rental on one of Fairfield's premier streets.
$14,000
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
Welcome to the newly built beach retreat at 86 French Street in Fairfield, Connecticut.
$12,500
Courtesy of Keller Williams Realty
SUMMER 2025 furnished beach rental available from June 1st to September 1st.
$10,000
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
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
ENJOY A TASTE OF BEACHFRONT LIVING !
$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
2025 SUMMER FURNISHED JUNE AUGUST.
$7,500
Courtesy of William Raveis Real Estate
Weekly Summer Rental 6 Nights, 7 Days.
$7,500
Courtesy of CRT Property Services, LLC
Are you looking to test drive Fairfield ?
$7,500
Courtesy of Brown Harris Stevens
Life Is Better At The Beach !
$7,500
Courtesy of William Raveis Real Estate
SUMMER 2025 June 1st 2025 August 31st 2025.
$7,250
Courtesy of Houlihan Lawrence
Hard to find direct waterfront rental home featuring private dock, Long Island Sound access deeded Fairfield beach access.
$7,200
Courtesy of Compass Connecticut, LLC
Beautifully updated FURNISHED colonial in Greenfield Hill.
$7,000
Courtesy of Berkshire Hathaway NE Prop.
The Shire a Southport compound !
$6,950
Courtesy of William Raveis Real Estate
NEW CONSTRUCTION LUXURY RENTAL !
$7,000
Courtesy of Keller Williams Realty
Available September 1 for academic year 2025 2026.
$6,500
Courtesy of Brown Harris Stevens
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