The 21 Most-Read Hamptons Real Estate Stories of 2021

The year 2021 was on another top-tier year in real estate on the East End, but we found what readers enjoy most is the stories behind the expensive homes and big deals.

Here are the most-read stories in Hamptons real estate:

1) At Home in the Hamptons – with Joy Behar

The View‘s Joy Behar gave readers a peek inside her Hamptons home filled with lots of artful yard sale treasures in the inaugural standalone issue of Behind The Hedges magazine in May.

2) Ruschmeyer’s in Montauk Has Found a Buyer

The Montauk landmark and summer hotspot overlooking Fort Pond went on the market in the fall of 2020 for $35 million. By April, it found a new owner. Of all our commercial stories this year, this one got the most eyeballs.

Ruschmeyer’s, a hotel and restaurant, went on the market in 2020 for $35 million.Courtesy Brown Harris Stevens

3) Rick’s Crabby Cowboy on Lake Montauk Lassoes a Buyer

While Ruschmeyer’s technically was the most-read commercial real estate story in 2021, Rick’s Crabby Cowboy Cafe was a close second. The restaurant that also has marine and rental units on Lake Montauk was also sold this spring — for $13.98 million we later found out (more than Ruschmeyer’s incidentally).

4) World Pie, a Bridgehampton Mainstay, Closes As Building Sells

The greater Bridgehampton community was devasted to lose World Pie, a Bridgehampton institution. After 22 years, the restaurant abruptly closed its doors for good in September as an off-market deal for the building closed for $7.2 million.

5) At Home in the Hamptons – with Jill Rappaport

Jill Rappaport, an award-winning and passionate animal advocate, television host and best-selling author, podcaster and e-commerce maven, gave Behind The Hedges a tour of her Water Mill log cabin for our September issue. “It’s truly, I think, a one-of-a-kind property in the Hamptons,” she told us — and we think she’s right.

Jill Rappaport at home on the Last Buck Ranch in Water Mill.Jim Lennon

6) Southampton Home Sells for Nearly $43 Million

A home on Meadow Lane in Southampton Village that had been the subject of a recent legal battle changed hands for nearly $43 million back in April in an off-market trade. We later found out that Robert Kraft, owner of the New England Patriots, was the one who bought the modern beauty on Billionaires’ Row in a deal brokered by Hedgerow Exclusive Properties, a Bridgehampton-based firm that specializes in off-market listings, as well as Douglas Elliman Real Estate.

7) At Home in the Hamptons – with Jill Martin

Jill Martin let Behind The Hedges into her Southampton home, where she not only has been living during the pandemic, but has been working too. Her home has been transformed into a studio, where she has filmed countless “steals and deals” and Shop TODAY with Jill Martin for NBC.

The Jungle Room with its fab banana leaf wallpaper and faux plants from HomeGoods and TJ Maxx reflect her ‘splurge and save’ skill set. “I believe in ‘high-low,’” says Martin, enveloped in her best-selling sherpa lounger.Jim Lennon

8) Oceanfront Bridgehampton Home With Storied Past Sells for $50 Million in Off-Market Deal

Way back in early January, we reported that a new Bridgehampton home overlooking the ocean had sold a month earlier in an off-the-market transaction for a whopping $50.15 million, making it one of the priciest sales in the Hamptons in 2020. Records showed that 187 Dune Road, a property that had an interesting past, was sold by developer Ziel Feldman to a limited liability company connected to The Fanatics mogul Michael Rubin. Erica Grossman of Douglas Elliman represented Feldman, while Gary Cooper and Preston Kaye of Hedgerow Exclusive Properties, which specializes in off-market listings, quietly repped the buyer.

9) Cannabis Company Making $42.5M Land Deal on North Fork

A fast-growing cannabis company purchased a 34-acre property in Jamesport for $42.5 million from Van de Wetering Greenhouses in one of the largest purchases in the burgeoning industry. It was the first known marijuana-related real estate buy on the East End since New York State legalized adult-use cannabis in March. Columbia Care Inc., which already operates a medical cannabis dispensary in Riverhead, has plans for a cultivation site at 5784 Sound Avenue with the first harvest and sales for the state’s medical-marijuana program expected later this year.

10) Casa Basso, Westhampton Restaurant With a 117-Year-Old Castle, Up for Sale

Casa Basso, a Westhampton restaurant known not only for its longstanding Italian menu, but also for the 100-year-old castle and two towering sculptures of musketeers that also sit on the Montauk Highway property, was officially listed for sale in November for $6.5 million. Bejto Bracovic and his wife, Zyli Bracovic, whom most know as Julie, have been the owners since 1986. They are only the third owners since the restaurant was established in 1928.

The swordsmen statues are part of the property’s charm.Courtesy of Douglas Elliman Real Estate

11) Buy a Unit in Montauk Shores Condominium Trailer Park for $1.675 Million

When a trailer goes on the market for so much money, people want to read about it, of course. The pricetag may have seemed odd, but it is an oceanfront trailer park, we are talking about. The gated community, one of the most coveted on the South Fork, enjoys 900 feet of coastline and access to some of the best surfing and surfcasting spots the island has to offer. Unit 14, a 595-square-foot home, ended up selling for $1.6 million.

12) Peter Brant, Stephanie Seymour Quietly Sell Sagaponack Oceanfront Estate

The billionaire businessman and his supermodel wife sold their oceanfront home in Sagaponack early in 2021 for $26 million. It remains the highest sale in Sagaponack Village of the year. By the way, this was another Hedgerow deal done off-market.

13) Julianne Moore Bids Adieu to Montauk Cottage

The actress and her director husband, Bart Freundlich, sold their cottage on Montauk’s Fort Pond for $2.85 million in February, six years after first listing it for $3.5 million. If you will remember, this was where Moore found a drunken stranger passed out on her couch. Afterward, the pair moved from this modest 1,000-square-foot cottage close to downtown Montauk for a more secure, gated mansion.

Over the summer, the photographer and the ex-wife of the designer Calvin Klein purchased a waterfront parcel on North Haven with a small fishing cottage on it, for $15.9 million. The 1.69-acre property at 31 Cedar Avenue, once owned by former Vermont Governor Howard Dean’s in-laws, Dr. Herman Steinberg and Dr. Ethel Bookhalter Steinberg, offers 250 feet of footage on the Sag Harbor Bay with a deep water dock.

Kelly Klein, inset, bought the waterfront property at 31 Cedar Avenue on North Haven for $15.9 million.
It all became clear why Kelly Klein bought a new place when we found out in August that her ex-husband had quietly sold the oceanfront estate that was still in his name in the spring. While the deal closed on May 17, Kelly Klein’s initials, “K.K.,” were still on a sign at the property’s gate when Behind The Hedges paid a visit after first hearing she was not living on West End Road anymore.

16) A ‘Homebuyer’s Holy Grail,’ the Least Expensive Homes in the Most Expensive Hamptons Zip Codes

Following PropertyShark’s recent list of the 100 most expensive zip codes in the country, on which there were six Hamptons hamlets, some wondered, what is on the low-end of these high-end markets? Analysts from Point2, an online real estate marketplace and sister division to PropertyShark, “set out to discover a homebuyer’s Holy Grail, the least expensive homes the most expensive zip codes,” as writer Andra Hopulele put it in the study of the data found by the analysts. Our readers just loved this.

17) Auction Scheduled for Chris Whittle’s East Hampton Estate

News that an auction was scheduled at the East Hampton home of embattled education entrepreneur Chris Whittle made headlines. In February, Whittle relisted his 11.2-acre property at 90 and 100 Briar Patch Road at $95 million with Bespoke Real Estate, but it seems his time had run out.

18) Joe Farrell’s Sandcastle in Bridgehampton Has a New Owner

After many years on the market, the well-known Hamptons builder sold his personal home for $31 million. Sandcastle, as it is known, was once rented by Jay-Z and Beyoncé. The massive 11.5-acre spread features nearly every conceivable luxurious amenity inside and out, and was last asking $34.995 million when Tal Alexander and Sara Goldfarb of Douglas Elliman Real Estate brought the buyers and closed the deal.

19) Ram’s Head Inn on Shelter Island Changes Hands

The iconic waterfront restaurant and hotel owned by the Eklund family for four decades was sold in March. “We’ve been there for 41 years. This would have been our 42nd summer,” Linda Eklund told Hedges at the time. She confirmed earlier this week that they sold not only the business but also the property, after several years on the market. We later discovered the 4.3-acre property traded for $7.59 million. The restaurant and inn have since reopened.

20) Market Update: The Hamptons Real Estate Shift, Part 2

Adriana Nava of Hamptons Market Data has been sharing her market reports with us all year long. The second in a three-part series on the Hamptons Real Estate shift in April garnered quite a bit off attention. With more people choosing to use their Hamptons home either full time or more often, the nature of participating in the Hamptons real estate market heading into summer 2021 is also evolving, she explains. Worth the read. 

21) Holly Rilinger, Fiancée Nab ‘Dream’ Home in East Hampton Despite Bidding War

Our 21st most read story of 2021 ends with a really happy one. Holly Rilinger, an internationally known health and fitness coach who once starred in the Bravo reality show, Work Out New York, and her partner, Jennifer Ford, finally found a home in the Hamptons in what we know has been extremely difficult market. They shared their journey with us earlier this year.

Holly Rilinger, right, and her partner, Jennifer Ford.Courtesy photo

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