The Boston Penthouse Jaylen Brown Tried to Sell in 2024 Is Back on the Market With a New Price

Some properties sell every few years. This one has not changed hands since Dwight Eisenhower was in the White House.

A 20-acre waterfront estate in Westport, Connecticut has just hit the market for the first time in 65 years, listed at $15 million.

The property sits in the Greens Farms enclave, overlooking Long Island Sound, and borders the 235-acre Sherwood Island State Park, Connecticut’s first state park. Andrew Whiteley and Wendy Ryan of Brown Harris Stevens hold the listing.

The story behind why it is just now available is what makes this one different from every other luxury listing in the state.

The Estate That Westport Never Knew Existed

Richard Stiegler built this compound in the 1940s. He was a shopping center magnate who at one point controlled 51 properties across the country. He bought this land, built a home on it, and created something he clearly never intended to share with the public.

The property sits on a private, unmarked road. There is no signage. No public access. Listing agent Andrew Whiteley put it plainly: “Because it’s unmarked and on a private road, even people who’ve lived in Westport their entire lives don’t know the estate exists.”

That is not a marketing line. That is 65 years of genuine privacy.

Stiegler died in 1967. His widow, Mary Lee Davey Stiegler, along with their two children, kept living there.

Over the following decades, she enlarged the original 1940s house into a 6,215-square-foot mansion, added a Palm Beach Room full of greenery next to an indoor pool, and expanded and renovated the grounds.

What started as a single home became a full family compound with two adjacent three-bedroom guest cottages, both dating to the 1940s.

What You Actually Get for $15 Million

The main house has 7 bedrooms, 6 full bathrooms, and one half bathroom across 6,215 square feet.

The architecture still carries the original 1940s bones: 20-foot entry columns, carved panels around the roofline, beautifully scaled living and dining rooms, and a smaller den with a fireplace.

The primary bedroom and its attached study are on the main floor, along with a second bedroom. Both have en-suite bathrooms.

The indoor pool was originally outdoor, moved inside at some point during the family’s long tenure. The Palm Beach Room sits adjacent to it, filled with greenery. The kitchen is large and windowed, with views of the grounds.

Outside, there is a tennis court and formal gardens across 20 acres that border protected open space on one side and Connecticut’s oldest state park on the other.

The views, according to Whiteley, stretch over marshes and out to Long Island Sound in a way that feels more like Nantucket than coastal Connecticut. He also mentioned a mating pair of bald eagles currently living on the property.

The two guest cottages sit on the same grounds, each with three bedrooms, both original 1940s structures.

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Properties like this rarely appear. When they do, the price has to carry the weight of the story.

Westport’s luxury market is moving fast right now.

According to Zillow data updated through April 2026, the average Westport home value has risen 12.7% over the past year, with homes going to pending in around 15 days. But that is the broader market. In the ultra-luxury tier, the dynamics are different.

The $5 million and above segment in Westport saw a surge in Q1 2026, with closings in that bracket jumping from 1 to 8 year over year.

Price per square foot across Westport jumped 21% year over year, and homes are selling at an average of 101% to 103% of list price. A well-positioned listing at this level moves. One that is hard to price by comparison, because nothing compares to it, moves on its own timeline.

This is a pattern worth watching. Josh Brolin is currently selling his $5 million Atlanta estate for reasons that have nothing to do with the house itself, a reminder that behind every headline-grabbing listing, the context always matters more than the square footage.

There is a channel that tracks exactly these kinds of stories as they develop on WhatsApp. You can follow it here if you want to stay ahead of luxury market moves without waiting on the news cycle.

Why This Matters

A property that has been privately held by one family for over six decades is not just a real estate story. It is a piece of preserved history entering the open market for the first time.

The Stiegler family did not just own this land. They built it out, maintained it through three generations, and kept it entirely off the grid in one of Connecticut’s wealthiest and most well-known towns.

Westport has long attracted names like Keith Richards, Anne Hathaway, Shonda Rhimes, and the late Paul Newman and Joanne Woodward. Bridgewater Associates, one of the largest hedge funds in the world, is headquartered there.

And yet this 20-acre estate remained invisible to all of them.

Whiteley described the neighbors’ relationship to the property with a telling detail: they knew the house through its Christmas parties, because those were the only times outsiders ever really experienced it.

According to Westport real estate market data for 2026, the $5 million and above segment of the market exploded in early 2026, with volume in that bracket up 46.4% year over year.

A 20-acre waterfront compound with no comparable sales history, on a private road, bordering a state park, is exactly the kind of asset that high-net-worth buyers in this market are actively looking for. Supply is structurally constrained. Land like this simply does not come back to market.

It is the same reason properties like Nicholas Hoult’s Hollywood Hills home sat unsold for over a year before finally closing at a significant financial loss and why Lindsey Vonn had to slash another $255K from her Beverly Hills mansion just three weeks after relisting.

Unique inventory at the ultra-luxury level succeeds or struggles based entirely on how well the price matches the reality of the moment.

At $15 million, the Stiegler estate is priced for what it is: irreplaceable.

Key Takeaways

• The estate at Greens Farms, Westport has not been on the market since the early 1960s
• Richard Stiegler originally built the property in the 1940s, when he controlled 51 shopping centers nationally
• After his death in 1967, his widow Mary Lee Davey Stiegler expanded the home and maintained the compound with her children
• The main house is 6,215 square feet with 7 bedrooms, 6 full bathrooms, and one half bathroom
• The property includes two three-bedroom guest cottages dating to the 1940s, a tennis court, indoor pool, and formal gardens across 20 acres
• The estate borders Sherwood Island State Park and has direct sight lines to Long Island Sound
• Andrew Whiteley and Wendy Ryan of Brown Harris Stevens hold the listing at $15 million

Is a property like this worth $15 million, or does the 65-year family history drive the price beyond what the market will actually pay? What do you think happens here? Drop your take in the comments.

Wrapping Up

A 20-acre waterfront estate that no one in Westport knew existed, held privately for 65 years, now asking $15 million. It is the kind of listing that only comes around once, which is exactly what makes it interesting.

If stories like this are your kind of thing, Build Like New covers the human side of high-end real estate, the history behind the listings, and the market context most outlets skip. Worth bookmarking.

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Disclaimer: This article is for informational purposes only. All property details are based on publicly available reports at the time of publication.