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
ANY TIME AT THE BEACH ! !
$60,000
Courtesy of William Raveis Real Estate
You'll never want to leave 'Splendido Manor, ' an iconic estate perfect for a sophisticated and active lifestyle.
$17,000
Courtesy of Compass Connecticut, LLC
15K month for term lease.
$15,000
Courtesy of Derek Greene
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
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
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
Summer, winter, short term or annual rental available.
$12,000
Courtesy of William Pitt Sotheby's Int'l
Step into a one of a kind opportunity at 35 Rose Hill Road a charming white brick antique originally built in 1912 as the Southport Telephone Exchange.
$11,000
Courtesy of William Raveis Real Estate
Welcome to Fairfield Beach, available as a student rental from October 1, 2025, to May 25, 2026.
$11,000
Courtesy of Higgins Group Real Estate
Enjoy your rooftop deck overlooking beautiful marshlands of Penfield Mills, perfect for stargazing, or just relaxing.
$10,000
Courtesy of Compass Connecticut, LLC
ACADEMIC 2028 2029 ONLY. Luxury rental fully furnished situated south of the Post Rd.
$9,500
Courtesy of Houlihan Lawrence
Introducing a captivating haven of luxury and comfort a magnificent 3126 sqft.
$9,500
Courtesy of Blue Lighthouse Realty, Inc
Complete interior and exterior renovation is just about finished.
$8,200
Courtesy of Houlihan Lawrence
Embrace the ultimate in sophistication and style with this stunning two bedroom, two bath apartment, located in the heart of Downtown Fairfield.
$7,500
Courtesy of Coldwell Banker Realty
Fairfield Beach area premier rental property !
$7,400
Courtesy of DeLibro Realty Group, LLC
Weekly Summer Rental 6 Nights, 7 Days.
$7,500
Courtesy of CRT Property Services, LLC
Welcome to 121 Woodland Road, a one of a kind, custom built Colonial that blends timeless design, high end finishes, and modern convenience in one of Fairfield's most desirable residential ...
$7,250
Courtesy of Compass Connecticut, LLC
NEW CONSTRUCTION LUXURY RENTAL !
$7,000
Courtesy of Keller Williams Realty
Come and see this Newly Remodeled home located in the fabulous FAIRFIELD Beach location !
$6,700
Courtesy of BHGRE Shore & Country
Enjoy this meticulously maintained custom built end unit townhome in the heart of Fairfield.
$6,500
Courtesy of William Pitt Sotheby's Int'l
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
Move in Just in Time to Enjoy Walking to Sandy Beaches, playing in the park and walking to the Center of Town from this completely renovated 3 Bedroom, 2 Full ...
$6,000
Courtesy of William Raveis Real Estate
Move in ready, well maintained and freshly painted, this 4 bedroom, 2.
$6,000
Courtesy of Coldwell Banker Realty
Welcome to Bronson House, Greenfield Hill's best new luxury rental opportunity !
$5,995
Courtesy of Berkshire Hathaway NE Prop.
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
if you need a short term rental, then you won't find a better location than this one.
$5,500
Courtesy of Compass Connecticut, LLC
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
Don't miss this well maintained 3 bedroom, split level home on a cul de sac conveniently located to Sacred Heart University and highways.
$5,000
Courtesy of Brown Harris Stevens
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
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