Playhouse Square Condo Complex in Westport CT

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About the Complex

Within walking distance to Winslow Park and downtown Westport and the Saugatuck River, Playhouse Square is in a great location with lots of activities and entertainment nearby.
Map of Playhouse Square Condo Complex, in Post Rd Westport CT

If you are looking for a great place to live or an investment, conveniently located in downtown Westport, nearby the beautiful Saugatuck River and the well-kept green space surrounding it, Playhouse Square is the perfect fit for you! 

Built in 1982, many of the condominiums have been completely renovated, featuring upgraded kitchens and baths. Most of these two bedroom and two bathroom townhomes offer cathedral ceilings in the living rooms accompanied by charming wood-burning fire-places. 

The 20 unit complex offers open concept living and dining while also providing sliding doors that open up to your very own patio overlooking the elegant lawns and gardens of Playhouse Square. These units are equipped with everything you would need, including a washer and dryer and a private garage. There is also plenty of extra parking spaces for any visitors you would want to host.

The condos have central air and forced air heat, providing an easy and comfortable year-round living. This complex is within walking distance to Winslow Park, which is beautiful and open year round, providing four seasons of enjoyment. 

If you are unfamiliar with the area of Westport and the surrounding towns, it is safer than 63% of US cities and Post Road East is one of the safest neighborhoods in Westport. Not to mention, the 12 different schools all in the 8 or 9 range, and Staples High School regularly recognized as the #1 public high school in Connecticut. This makes it a wonderful environment to raise a family in.

With it taking just over an hour to get to Grand Central Terminal by train, Playhouse Square is close to many restaurants, churches, temples, shops, businesses and beaches, including Compo Beach which is a very popular 29 acre sand beach along the shore of Long Island Sound. It is even handicap accessible as Westport welcomes diversity in every shape and form.

There are also very many country clubs, Birchwood Country Club being just down the road, which are great places to dine and swim in the extravagant pools which almost all of them have to offer. Longshore Club Park, which is just west of Compo, offers many activities including; sailing, paddleboarding, golfing, and many more that kids and even adults would love!

Downtown Westport is the perfect place to walk around and shop; home to many clothing stores, restaurants, cafes, and salons. You can walk along Jesup Road, Imperial Ave, Post Road and the surrounding area and you will find all of your favorite shops. If you take a drive through town on any given day you will see many bustling and smiling people shopping around Westport town Center.

Bar Taco, a restaurant located right on the Saugatuck River is a Mexican, vegetarian-friendly place that is rated the third best restaurant in all of Westport. Although it is often packed, upon reservation it is a great place to go for a night out.

Today, Westport remains a flourishing town popular with artists and boasting a rather vibrant creative scene. A town built on diversity, Westport has many Christian-based churches and is also home to five different Temples. Westport is filled with many businesses, shops, a theater, and is a popular town from which to commute to New York City. Full of beautiful scenery, a variety of amenities for you and your family to enjoy, and top-notch schools to guide your children to success, Westport is the perfect town for you to develop and thrive. 

Between the schools, location, safety, and updated living spaces, Playhouse Square is the perfect place for you and your family to grow and thrive in a very vibrant and welcoming town in southwestern Connecticut.

Homes for Sale

There are currently no homes for sale in Playhouse Square.
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Homes for Rent

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Recently Rented Homes

1 recently rented

100.0% sale / rent ratio

0 avg days on market

most recent rented homes

Condo Home

301 Post Road, unit 16, Westport CT $ 3,100 Closed
2 Beds 2 Baths 1,145 Sqft Built in 1982 cnt
Courtesy of SmartMLS
Rented on 1 Sep 2020
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Local Information



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.

This complex is 100% below the neighbourhood's $ 1.25M avg price
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Westport, CT

Located on the water, this vibrant town offers beauitful, luxury properties.

This complex is 100% below the town's $ 1.66M avg price
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Fairfield County

Fairfield County is one of the wealthiest communities in Connecticut. Contact Dagny's Real Estate if you are looking to buy a home in Fairfield County CT.

This complex is 100% below the county's $ 549K avg price
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Near-by Condo Complexes

Terra Nova

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

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Harvest Commons

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

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Regents Park

This gated community features spacious and upscale condos with gourmet kitchens, fireplaces, and access to Compo Beach and Longshore Country Club.

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