Playhouse Square Condos in Westport, CT

Address: 301 Post Road, Westport, CT
Total Units: 20
Year Built: 1982
Style: Townhouse condominium
Bedrooms: 2
MLS Price Range (verified sales): $398,000 – $467,500
HOA Fee: $500/month
Property Tax: approximately $3,804/year

Playhouse Square Condos for Sale

Playhouse Square is a 20-unit community, and units here do not come up often. Five sales have closed in the MLS record over several years, which reflects how infrequently owners move on. When a unit does hit the market, buyers who are already familiar with the complex and have financing in order tend to move faster than those who are just starting their search. If you are watching Westport CT condos for an opening at Playhouse Square, the best approach is to get on The Engel Team’s radar before something lists publicly. Off-market awareness matters in a building this size.

Recently Sold at Playhouse Square

MLS data shows five closed sales at Playhouse Square. Prices ranged from $398,000 to $467,500, with a median of $429,000. Every sale on record involved a 2-bedroom, 2-bath unit at 1,145 square feet, producing a median price per square foot of approximately $375. That is a narrow band of comparable data, which means pricing any individual unit requires careful attention to condition, renovation level, and the specific setting within the complex.

The spread between the lowest and highest recorded sale is roughly $70,000 on identical square footage. In a small building, that gap almost always comes down to interior condition and how well an individual unit was maintained or updated. Buyers should pull the full resale history on any unit they are considering and compare finishes carefully before making an offer.

About Playhouse Square

Playhouse Square sits at 301 Post Road in Westport, CT, built in 1982 as a townhouse-style condominium complex with 20 units. The setting is one of the more distinctive features of this building. Units overlook the lawns and gardens of Playhouse Square, giving the property a landscaped, residential feel that is uncommon for a Post Road address. The complex takes its name from its proximity to the Westport Country Playhouse, one of the oldest and most respected regional theaters in the Northeast. That location places Playhouse Square within walking distance of the Saugatuck train station, which is a real advantage for anyone commuting or running errands without a car. For a 42-year-old building, the address and walkability remain genuine selling points that hold value across market cycles.

Homes and Layouts at Playhouse Square

Every unit in the MLS record at Playhouse Square is a 2-bedroom, 2-bath configuration at exactly 1,145 square feet, which suggests the building was constructed with a consistent floor plan throughout. The townhouse style means buyers get vertical living rather than a flat layout, typically with living and dining areas on one level and bedrooms above or below. Garage parking is included, which is meaningful in a Post Road location where street parking is not a realistic alternative. The complex is small enough that no two units share an identical position relative to the gardens, so setting and light can vary between units even when the square footage is the same.

What Buyers Need to Know

The HOA fee at Playhouse Square is $500 per month. Before closing, buyers should request the current reserve fund balance, the most recent reserve study, and documentation of any special assessments levied in the past five years. A building constructed in 1982 is over 40 years old, and mechanical systems, roofing, and common-area infrastructure require ongoing capital. The reserve position tells you how well the association has planned for those costs and whether a special assessment is likely in the near term.

Property taxes on recent sales have run between approximately $3,610 and $4,152 per year, which is low relative to Westport’s town median, where a $1.5M single-family home carries roughly $19,000 to $20,000 in annual taxes. That tax profile is one of the practical reasons buyers look at Westport CT real estate in condominium form rather than single-family. You get the address and school district at a cost structure that is meaningfully different.

Because units in this building share consistent square footage, resale value here depends heavily on interior condition and upgrade level. A unit that has been renovated recently will price and sell differently from one that has not been touched since the 1980s. Buyers should inspect each unit independently rather than assuming comparability from sale to sale. Ask for the resale package from the association, which should include governing documents, current financials, rules on pets and rentals, and owner-occupancy data. Rental restrictions, if any, affect both your flexibility as an owner and the availability of conventional financing. A lender will require a condo questionnaire, and the answers affect loan approval.

The building’s Post Road location and proximity to the Saugatuck River area mean buyers should verify the flood zone designation for this specific parcel. Even properties that are not directly on the water in this part of Westport can fall within a designated zone that requires flood insurance. Confirm with your attorney and insurer before making assumptions based on address alone.

Buying or Selling at Playhouse Square

Five sales over several years in a 20-unit building means comparables are thin. That cuts both ways. For sellers, a well-renovated unit with a strong presentation can push past prior sales without much resistance from the data. For buyers, the narrow comp set makes it harder to know whether an asking price is reasonable without someone who tracks this building specifically.

The Engel Team monitors small condo communities like Playhouse Square closely, including units that trade off-market or come to market with limited public exposure. If you are looking at Westport homes for sale and this building is on your list, contact us for a current market read. If you own at Playhouse Square and are considering selling, we can tell you exactly how your unit compares to the recorded sales and what buyers in this price range are expecting in terms of condition and finish. Reach out to The Engel Team to start the conversation.

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