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.
Indulge in breathtaking views stretching all the way to New York from this remarkable abode !
$60,000
Courtesy of William Raveis Real Estate
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
Welcome to Blue by the Sea, a stunning retreat on the shores of Long Island Sound !
$50,000
Courtesy of William Raveis Real Estate
SUMMER RENTAL ACADEMIC Escape to 2154 Fairfield Beach Road for the ultimate summer getaway !
$50,000
Courtesy of The Brokerage of New England
ANY TIME AT THE BEACH ! !
$60,000
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
This newly renovated, fully furnished home is available for rent for the month of August.
$20,000
Courtesy of Brown Harris Stevens
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
List price of 15, 000 is for ENTIRE SEASON, 6 4 25 8 20 25.
$15,000
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
Tucked away on a quiet cul de sac, this 8, 000 sq.
$12,500
Courtesy of Farnam Realty Group
Introducing Tiny Blue by the Sea a charming Colonial beach cottage boasting captivating sunset vistas through its expansive wall of windows.
$12,000
Courtesy of William Raveis Real Estate
Breathtaking panoramic views await from the stunning rooftop deck of this remarkable house !
$12,000
Courtesy of William Raveis Real Estate
Location, luxury, and style come together in this beautifully renovated Cape Cod home, ideally located in the highly sought after Fairfield Beach area.
$12,000
Courtesy of William Raveis Real Estate
Spectacular Fairfield Beach Academic Year Rental Available September 1st 2027 May 29th 2028.
$12,000
Courtesy of Berkshire Hathaway NE Prop.
SUMMER 2025 furnished beach rental available from June 1st to September 1st.
$10,000
Courtesy of William Raveis Real Estate
Nestled in the desirable beach area of Fairfield, this beautifully updated Colonial home is a perfect blend of classic charm and modern convenience.
$9,500
Courtesy of William Raveis Real Estate
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
Located in Southport's highly desirable neighborhood, this renovated colonial home on 0.
$8,500
Courtesy of Coldwell Banker Realty
Student rental available for the 2025 2026 school year.
$8,000
Courtesy of William Raveis Real Estate
Welcome to your dream rental !
$7,500
Courtesy of Realty ONE Group Connect
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
Fairfield Beach area premier rental property.
$7,400
Courtesy of DeLibro Realty Group, LLC
FURNISHED SUMMER RENTAL Welcome to your dream beach escape conveniently located between Faifield Center and the beach.
$7,250
Courtesy of Coldwell Banker Realty
NEW CONSTRUCTION LUXURY RENTAL !
$7,000
Courtesy of Keller Williams Realty
NEW CONSTRUCTION LUXURY RENTAL !
$7,000
Courtesy of Keller Williams Realty
Discover your private waterfront oasis with this charming rental in the exclusive Lake Hills Neighborhood.
$6,750
Courtesy of Realty ONE Group Connect
Discover urban coastal lifestyle in this fully renovated Fairfield Cape Cod home, located on a quiet, tree lined street.
$6,500
Courtesy of William Raveis Real Estate
Available September 1 for academic year 2025 2026.
$6,500
Courtesy of Brown Harris Stevens
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
This spacious 4 bedroom, 2.
$6,075
Courtesy of Keller Williams Prestige Prop.
Come Experience 2107 North Benson, a versatile property offering exceptional living spaces.
$6,000
Courtesy of Keller Williams Realty
Be the first to live in this absolutely gorgeous BRAND NEW CONSTRUCTION 4 Bedroom, 2 Full Bath, incredible rental, just completed by a well known local builder with no expense ...
$5,900
Courtesy of Higgins Group Real Estate
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