When talk turns to real estate — and when in Westport does it not? — most conversations involve single-family homes.
New homes. Old homes. Teardowns. Renovations. Sustainable homes. White homes with black windows. You know the drill.
Sometimes we talk about apartments. The ones opposite Greens Farms Elementary School, which everyone feared and no one notices anymore. Those coming on Hiawatha Lane and Cross Street (that’s the construction you see at the crest of Post Road West).

After initial controversy, the 1177 Post Road East apartments have become just another part of the landscape.
Especially, the apartments that are nearly finished, at the corner of Wilton Road and Kings Highway North.
No one seems to talk about condominiums.
Except the people buying them.
Right now, lots of folks want to.
The condo market is hot. And I say that not just as a condo owner myself.
Our friends at KMS Team at Compass note the appeal. Condos are “maintenance-free, single-family style living, (for buyers) accustomed to single-family homes but no longer interested in the upkeep – snow removal, lawn care and the like.”
They include empty nesters looking to downsize while staying in Westport (or perhaps keeping a foothold here while spending several months a year elsewhere); older folks moving from other places who want to be close to their adult children and grandkids; divorced or widowed men and women, and young professionals who want to own a home but are not yet ready for a house.
Other condo-buyers are city dwellers looking for a weekend escape, and investors.
Single floor living, first floor primary suites and elevators are sought-after condo features.
For all those buyers, prices are rising quickly.
One KMS agent recently listed a Lansdowne condo. It needed updating.
Yet within days there were multiple offers. It will close early next month — at over the asking price.

Here are median sales prices, for 4 Westport condo complexes:

According to KMS, supply and demand is driving the condo market in several ways.
While on the surface Westport seems to have a fair number of condos, most multi-family new construction in recent years has been in apartments, keeping condo supply tight.
Due to the lack of affordable, single-family homes on the market, many buyers expand their search to condos, raising demand.
Additionally, Westport has a higher-than-national-average percentage of households with someone over 60 (the typical condo buyer).

Source: 2016-2020 American Community Survey, via Partnership for Strong Communities
What’s ahead?
KMS Team’s experts envision smaller, boutique-type developments as the new norm, due to the lack of expansive land.
Large-scale developments like the proposed Hamlet in Saugatuck take substantial funding, and often meet zoning and neighborhood resistance.
Projects like the proposed Glendinning Place off Weston Road (the former Bridgewater office complex) have challenges too. But their smaller scale and lower density make those obstacles easier to overcome.
Connecticut’s 8-30g mandate has had an impact. But with litigation behind us, KMS believes that Westport builders, officials and residents will “move forward in a thoughtful, deliberate manner to stay ahead of 8-30g, preserving the character of Westport while meeting the demands of current and future residents.”
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2ND STORY (ho ho): Westport’s condo history dates to the 1980s. KMS Partners offers this brief history.
Strathmore, on the Norwalk line off Kings Highway South, was built in 1980. Its 64 units consist of 1 or 2 bedrooms in a townhome, 2-story style.
Harvest Commons, built 1980-1983 on the site of a former Post Road East orchard and farm stand (hence the name) has 80 units, with a mix of ranch-style and 2-story townhomes. A clubhouse and gardening area are offered, plus a pool.

Whitney Glen, an age-restricted community (62+), has 62 units off Main Street East, near Compo Shopping Center. It was built between 1982 and 1986.
Lansdowne, on Post Road East on the site of a former mini-golf course and driving range, was constructed in 1983. The 90 Nantucket-style homes are set back far from the road.
Playhouse Square, built in 1983, replaced a former ramshackle boarding house behind the shopping center, next to Winslow Park and the Westport Country Playhouse. Its 20 units are all 2-bedrooms, mostly 2 stories.
Regents Park, on the Post Road near Harvest Commons, was built in 1985. 81 townhomes offer 2 or 3 bedrooms, and 2-car garages.

Regents Park
Also built in 1985, Edgewater Commons on Hillspoint Road replaced the former Penguin club and apartments. Its 25 units have high ceilings, skylights and private patios.
It was another 20 years before the next complex was built with a community pool: Terra Nova, in 2004. Its 54 large townhomes include features like finished basements, on Post Road West near the Norwalk line.
With land unavailable to build large scale complexes, builders began building smaller developments.
One example is Daybreak Commons, between Main Street and Weston Road. Named for the florist that once occupied the site, it includes 5 stand-alone townhouses and 4 duplex units, for buyers 55 and older.
Bankside House was the first luxury condo on the Saugatuck River. Sales of its single-floor homes, each with private outdoor living spaces, began last fall. Non-penthouse units sold at an average price per square foot of $1,211, while two penthouse units went for $1,654 per square foot. Two penthouse units are available now, at an average asking price of $1,703/square foot.

Bankside House (Photo/Howard Edelstein)
The Mill Westport — also on the Saugatuck, in a converted mill further east on Richmondville Avenue — has an average selling price of $1,108 per square foot for the 11 units sold in 2024 (mostly off-market). Three units are listed for sale now, with an average asking price of $1,452/square foot.
You may not be talking about condos these days. But plenty of other people are.
And they’re buying them.
(Every day, “06880” explores the diversity of Westport: its people, its institutions, its real estate. We bring the community together — but we need readers’ support. Please click here to help. Thank you!)

Folks don’t talk much about hemorrhoids or colonoscopies either.
That has little to do with the actual feelings about them.
Interesting that “Strathmore” is included in the Westport graphic even though the town of Westport will not recognize the complex as being in Westport. Try to get a beach pass while living on Strathmore Lane. it’ll be fun for you!
Great summation Dan‼️🇺🇸
None of these condos are affordable for people like me.
Thank you for saying it Tracy
Dan, you forgot Indian River Green in Saugatuck and Old Hill off Post Road West, two bedroom condo townhouses of about 20 units each built in 1987.
Not only are many of the condos you mention not affordable for lots of folks, some of them are truly awful looking. Notable among that category are the building at Kings Highway/33 and the 1177 on the Post Road. This trend of filling up whatever land is available with unattractive multi-family housing is upsetting and negatively impacts the town. It would be great if the Architectural Review Board (or someone else in charge) was involved in supervising design to achieve more attractive buildings.
Just a note: The Kings Highway North/Wilton Road and 1177 Post Road buildings are apartments, not condos.
Condos, apts, same thing.. and why builders love them !
The noose around peoples neck of condo association fees which bears no relationship whatsoever to what it actually costs to maintain said covered costs..I’d go so far as to say it is daylight robbery at best probably x3 mark up of actual cost !
So that’s where they get you by the short and curlies.
It’s not ok
It’s where they get an annual payment for nothing.
Money for old rope as my parents say.
Ciara, I live at the Playhouse Condominiums, behind the post office. I was on the board for many years, and I look at every budget presented (then and now) carefully.
I know exactly where every dollar goes: maintenance, roof and elevator repairs, snow plowing, electricity, insurance, management fees, etc., etc., etc.
Our monthly fee is $550. It was raised this year from $500, where it stood for many years. There is no “daylight robbery,” and certainly no “x3 mark up of actual cost!”
If you had a bad experience with a condo, I’m sorry. But please don’t present your personal opinion as an actual fact.
Well Dan, maybe you happen to live in one of the only condos not ripping people off on condo fees !
Most I assure you do ! I have plenty friends living in condos. It is a very commonly expressed frustration. Almost without exception, I might add.
So It’s not my personal opinion it is a fact ! A very known fact what’s more ! Glad you found a condo that doesn’t !
But I like you am entitled to my factual opinion based upon 90% of the opinions of my condo dwelling friends.
Factual opinion based on opinions of others? That’s a head scratcher.
And Ciara your right too. Thx