The R Report: Retiring? Westport is the Perfect Place!

There are many condos to choose from ranging in price from the $300,000s to more than $1 million.

So many empty-nesters are checking out multiple locations for retirement and Westport is one of those spots.

We enjoy four seasons here — each with a beauty unto its own. Summer fun abounds with beach life, free concerts at the Levitt, water sport programs, including sailing, kayaking or private yacht tours for hire. All other seasons, Westport is home to the Westport Country Playhouse, which is an absolute "theater jewel" open all year long. The Westport Public Library is the hub of the town offering reading rooms, various programs, Internet classes and movie rentals.

Longshore, celebrating its 50th anniversary this year offers residents their own magnificent golf course, driving range and park with marina. Tennis anyone? Multiple tennis courts all over town and at the beach with programs that you are able to sign up at the recreation department are available in several seasons.

Shopping here is fantastic with plentiful chic boutiques and other stores such as Banana Republic, The Gap, Vinyard Vines, Mitchells, and JCrew, just to name a few.

Restaurants abound with offerings such as Splash, located at Longshore overlooking the water, Positano's on the water, Tavern On Main that offers outdoor dining in the summer, and Vs which is a favorite lively bar and restaurant.

So there is plenty to do and many organizations to volunteer your time.

Lets get down to real estate offerings.

Want low maintenance living? Westport has many condos for sale that most do not know exist.

Here is a list of the larger condo communities:

  • Harvest Commons has many amenities such as a pool, pool house, and tennis courts
  • Regents Park is a gated community which won the beautification award for the town last year that has a club house, changing rooms, tennis courts and a pool for residents
  • Lansdowne, includes more than 33 acres, a picturesque gazebo sited on park-like property with a pool house, pool, paddle tennis and tennis court
  • Whitney Glen, centrally located in the heart of Westport
  • Birchwood, boasting a pool and club house
  • Playhouse Square Condos offers a place for a care-free lifestyle
  • Bradley Commons is great for easy access to New York by train and boasts brand new units
  • Edgewater Commons is just a short walk or bike ride to the beach
  • Strathmore offers a pool, paddle tennis and is tucked away yet close to shopping
  • Terra Nova offers larger units, a pool, club house and is a gated community

Prices and personality are different at each condo community, ranging from $319,900 to $1,099,000.

Right now the majority of the units have two bedrooms and two-and-a-half baths and are priced in the middle to high $600,000 range. For $799,000 and up you can get three bedrooms, three-bath units. First-floor masters are at premium and sell for more than $1 million in Regents Park.

Check out the accompanying photos of condos that have sold this year.

So if you are thinking of retiring, Westport is the perfect place. It offers low maintence living, all the amenities and so much to do regardless of the season.


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