The Trailblazing Women Who Sell Prized Properties On Martha’s Vineyard

Massachusetts' Martha’s Vineyard has long been a magnet for high profile home sales given its status as an elite haven for presidents, business magnates and celebrities.

Barack and Michelle Obama live part time on the island, less than an hour ferry ride from southeastern Massachusetts; they purchased their $11.75 million residence in 2019. And former first lady Jacqueline Kennedy Onassis once lived on a 430-acre Aquinnah property that was sold in 2021 for $37 million—save for about 60 acres where members of the Kennedy family maintain a home.

Representing an intriguing mix of residences spread across the island’s six towns, Tea Lane Associates is steeped in the island’s storied history—its pioneering women founders opened the real estate firm in 1967.

With offices in Chilmark and West Tisbury, the family business excels in multi-million dollar deals. In 2023, the 13-member firm represented buyers in the Vineyard’s top two priced land transactions, $4.7 million and $10.5 million. The firm also represented both buyers and sellers in seven of Chilmark’s ten highest sales in 2023, including the top three. Tea Lane Associates recently became a member of Forbes Global Properties.

We spoke with Tea Lane Associates’ co-owner Abby Rabinovitz about her firm’s intrepid founders and the Vineyard’s famed New England homes, some dating to the 1700s.

You and co-owner Leslie D. Pearlson are the nieces of Eleanor D. Pearlson who co-founded the firm with her companion and business partner Julia Green Sturges 57 years ago. We understand that your Aunt Eleanor was a bit fiery.

Oh, she had chutzpah. She was one of the first WAVES in World War II, and was the executive secretary for the Henry Street settlement house on Manhattan’s lower east side, and Julie was a board member—that’s how they met. Julie was old New York society, but she was an outlier, a feminist in a quiet way. You’d start talking to her and realize she had a spine of steel. When they moved here, they fell in love with the Vineyard.

In teaching you the business of real estate, which you’ve been in for 25 years, they must have been superb role models.

Definitely, and especially in the way they took risks. When they arrived, they purchased a large tract of land off Tea Lane in Chilmark and turned it into a subdivision, creating a really wonderful neighborhood of homes. But they were outsiders. Being among the few women in the field at the time, they were challenged. They definitely got pushback, but they never backed down. They were very generous people with big hearts, and people grew to love them. I strive to be as generous as they were.

Martha’s Vineyard conjures the feel of bracing salt air, the taste of steamed lobster and blueberry pie, and enchanting sites: iconic lighthouses, historic towns and quaint harbors.

The natural beauty is incredible. The Vineyard has something for different kinds of people, and they come from all over the world. You can live in town, somewhere fairly isolated, near the beach, or in a country estate. You can live a quiet life, or you can partake in film and music festivals, nightlife, farmer’s markets, book fairs, lecture series …. And there’s kayaking, canoeing, biking, hiking, golf, tennis, fishing, sailing and yachting. Different people come to the Vineyard for such very different things. Some join with friends or family, and others do important cultural and political work here.

Describe the Vineyard’s look and feel, specifically the topography.

The topography varies greatly. Aquinnah has a dune landscape, in Chilmark, it’s rolling hills. And then there are the ponds (15 coastal pond systems and 61 fresh water ponds), with a great variety of homes. There are homes along the north shore, which is calm and good for swimming, versus the south shore that’s along the Atlantic Ocean.

Please describe how the Vineyard is laid out, and also tell us about the architecture.

There’s ‘up island’ with the towns of Chilmark, West Tisbury and Aquinnah, and ‘down island’ with Edgartown, Oak Bluffs, and Tisbury (Vineyard Haven). Generally, up island is more rural and down island has bustling port towns. The Vineyard doesn’t have uniform architecture like Nantucket and other communities. You can find mid century, contemporary, and country and farmhouse style. In Edgartown you’ll find beautiful homes once owned by whaling captains (the town was a major 19th century whaling port). Most are Greek revival style built in the 1800s. Current listings for those range from $3.975 million to $14.95 million. But as far as a beautiful home, you’ll find that anywhere.

We’re especially taken with Oak Bluffs’ 150 year-old gingerbread cottages, more than 300 of them—all candy-colored and dripping with fairy tale ornamentation.

In January, we sold a two-bedroom gingerbread at 25 Butler Avenue. It was built in 1870 with tongue and groove wood construction. Tiny at 697 square feet, but totally charming—and definitely pink! It was sold furnished and turnkey for $740,000. Of course, Oak Bluffs has many other types of architecture.

Detail the Vineyard’s overall real estate trend; we imagine sales volume has been lower, tracking with most other regions.

Yes, it’s been slower the last two years. We’ve had lower inventory, which pushes prices up from high demand. The average price increased 6% from $1.888 million in 2022 to about $2 million in 2023. It’s a seller’s market. Still, there are wonderful properties. And people just want to move here.

What’s your buyer demographic?

The majority are from the U.S., but we get buyers from all around the world. In the U.S., most are from the east coast, and there’s also a very big California contingent. And there are other areas, including Chicago and Texas. People used to view the Vineyard as a place to spend a few weeks. I think more are now wanting to spend longer periods of time here. Many buyers are looking for a second home that they’ll cherish and stay in for a good part of the year. They become members of our community and they contribute to it in many different ways.

Please describe two of your current standout listings.

A 2001 five-bedroom craftsman/contemporary farmhouse style with a guest studio on Menemsha Inn Road in Chilmark—3,241 square feet on 5.6 lush acres. There’s a real serenity to the land. The home has a private waterfront and lovely water views of the Vineyard Sound. Sunsets flood just about every room. I love the realness, the authenticity of this home: cedar shingles, salvaged heart pine floors, handsome old beams. The home is listed for $9.25 million.

By contrast, we have an older 1976 five-bedroom home in Chilmark that was partially renovated in 2019; it includes a two-bedroom guesthouse built in 1999. The view takes your breath away: a very intimate view of Menemsha pond, but from high up. It’s a salt-water pond that eventually leads to the Vineyard Sound. The 4,150 square-foot home is on three acres with 750-plus feet of pond frontage that includes a 48-foot dock. Fourteen of the 16 rooms in the home and guesthouse have those amazing pond views. We’ve listed the home for $9.95 million.

After nearly 60 years selling homes on Martha’s Vineyard, what has kept Tea Lane Associates in the game, one played in such a small competitive market?

Given our history and Tea Lane’s exceptional dedicated team, there’s an authenticity our clients notice which I think is rare. All of us have a deep connection to this island. Some of our agents/brokers have grown up here, many others have settled here and are raising families. We love this island and know it intimately, and we all listen and learn from each other.

MORE FROM FORBES GLOBAL PROPERTIES