Best Places to Live in Westport - Connecticut -

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About the Lifestyle in Town

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Westport is located in Fairfield County on beautiful Long Island Sound. This coastal Connecticut town was first inhabited by American Indians and so many of the neighborhoods, streets and landmarks still hold historic American Indian names.

The first non-American Indian settlers were a group of five farming families. The "Bankside Farmers" arrived in 1648 and settled in what is now known as Westport's Greens Farms area, named after farmer John Green. Westport continued to grow as colonial settlers from surrounding towns moved to the area.

Saugatuck Village was the first area to be developed, Saugatuck (meaning "mouth of the tidal river") was important to farmers, as it allowed them to distribute their goods to other markets. Other business popped up along Saugatuck's riverbanks, forming a bustling community with stores, wharves and even a tavern.

As the community grew, a center for town meetings and worship was warranted. In 1711 the first church was built in Green's Farm. On April 25, 1777, during the Revolutionary War, British soldiers landed at Compo Beach, which is a very popular modern day beach and recreation complex. After several battles in neighboring towns, the British marched back though Saugatuck and fought with local militia in the Battle at Compo Hill. The Minute Man Statue located on Compo Road honors those who died. A second meetinghouse was erected in 1736, but was burned down in July of 1779 by British soldiers.

Saugatuck still thrived after the Revolutionary War and the villagers sought their own charter. After 130 families came together, Westport was incorporated as a town on May 28, 1835.

Compaug Beach, more commonly referred to as Compo Beach, encompasses 29 acres of beautiful beaches and park areas. It is a picturesque beach, at the mouth of the Saugatuck River. The beach has been a popular destination since early colonial settlers decided to make this land their home in the 1700's. Today, Compo is very popular and exclusive neighborhood.

Today's Westport remains a flourishing town popular with artists and has a vibrant creative scene. A town built on diversity, Westport has many Christian-based churches and is home to five Temples. Westport is filled with many businesses, shops, a theater, and is a popular town from which to commute to New York City.

Westport Demographic Details:

  • Area: 20
  • Population: 26,458
  • Households: 9,955
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Areas and Neighborhoods

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Westport CT Greens Farms

The oldest neighborhood in town, this area is a beautiful place to live, with its exquisite homes and shops. This neighborhood is also home to the prestigious private school,, Greens Farms Academy.

  • 49Homes
  • $3.45MAvg Price
  • 5,302Avg SqFt
  • 1965Avg Year
... more about the homes & lifestyle

Westport CT Saugatuck Island

Located a very convenient distance to both the Metro-North train station and Compo Beach, this area of Westport is brimming with historical charm.

  • 12Homes
  • $3.04MAvg Price
  • 3,533Avg SqFt
  • 1981Avg Year
... more about the homes & lifestyle

Westport CT Compo Beach

Many homes in this neighborhood boast beautiful water views and easy access to the beach.

  • 46Homes
  • $2.75MAvg Price
  • 4,212Avg SqFt
  • 1968Avg Year
... more about the homes & lifestyle

Westport CT Saugatuck

A charming neighborhood located on the shores of Long Island Sound, it is only a short distance to both the Metro-North train station and Compo Beach.

  • 46Homes
  • $2.19MAvg Price
  • 4,049Avg SqFt
  • 1985Avg Year
... more about the homes & lifestyle

Westport CT Old Hill

One of the town's oldest neighborhoods, this historic section features many updated homes from the Revolutionary and Victorian eras.

  • 21Homes
  • $1.86MAvg Price
  • 5,130Avg SqFt
  • 1952Avg Year
... more about the homes & lifestyle

Westport CT Hunt Club

Located near the Fairfield County Hunt Club, tennis, ice skating, and many more activities are just at your fingertips.

  • 29Homes
  • $1.75MAvg Price
  • 5,189Avg SqFt
  • 1986Avg Year
... more about the homes & lifestyle

Westport CT Roseville - North Avenue

This upscale area of town features many beautiful homes from the colonial era. Bordering the Merritt Parkway to the north, this area is perfect for commuters.

  • 39Homes
  • $1.72MAvg Price
  • 5,296Avg SqFt
  • 1974Avg Year
... more about the homes & lifestyle

Westport CT Coleytown

Bordering the Weston town line, this area is home to many colonial houses that still exhibit their original architecture and style to this day.

  • 51Homes
  • $1.66MAvg Price
  • 4,866Avg SqFt
  • 1967Avg Year
... more about the homes & lifestyle

Westport CT Long Lots

This well sought out neighborhood features many homes from the colonial era that have been newly renovated.

  • 26Homes
  • $1.63MAvg Price
  • 4,738Avg SqFt
  • 1978Avg Year
... more about the homes & lifestyle

Westport CT Red Coat

Thi small, private area of town is in close proximity to the Merritt Parkway, making it great for Manhattan commuters.

  • 10Homes
  • $1.57MAvg Price
  • 4,978Avg SqFt
  • 1947Avg Year
... more about the homes & lifestyle
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Condominium Complexes

Westport CT Terra Nova

Built in 2004, this gated community provides residents a community pool and clubhouse.

  • 1Homes
  • $1.08MAvg Price
  • 3,260Avg SqFt
  • 2004Avg Year
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Westport CT Harvest Commons

Residents of these spacious condos are granted rights to Compo Beach and Longshore Country Club.

  • 1Homes
  • $775KAvg Price
  • 2,141Avg SqFt
  • 1981Avg Year
... more about the homes & lifestyle

Westport CT Lansdowne

This gated community offers stunning condos with a clubhouse, pool, and an easy commute to New York City

  • 3Homes
  • $755KAvg Price
  • 2,183Avg SqFt
  • 1985Avg Year
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Westport CT ​Bradley Commons

Located within walking distance to the train, these condos also offer fireplaces and a private deck.

  • 1Homes
  • $679KAvg Price
  • 1,756Avg SqFt
  • 2011Avg Year
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Westport CT Playhouse Square

With gorgeous views of Naugatuck River, these units are within walking distance to Winslow Park and shopping at Main Street.

  • 1Homes
  • $465KAvg Price
  • 1,145Avg SqFt
  • 1982Avg Year
... more about the homes & lifestyle

Westport CT Edgewater Commons

Residents have access to Longshore Country Club, as well as tennis courts and community pool on site.

  • 2Homes
  • $249KAvg Price
  • 952Avg SqFt
  • 1958Avg Year
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Westport CT Birchwood

These ranch style condos feature spacious private decks, in-ground pool, clubhouse, and easy access to public transportation.

  • 9Homes
  • $231KAvg Price
  • 1,426Avg SqFt
  • 1981Avg Year
... more about the homes & lifestyle

Westport CT The Saugatuck

This adult community offers residents plenty of activities, from exercise classes to card nights.

  • 1Homes
  • $199KAvg Price
  • 741Avg SqFt
  • 1995Avg Year
... more about the homes & lifestyle