5 Best Places to Retire in the Hamptons

Midlam Ryan Team June 7, 2023

5 Best Places to Retire in the Hamptons

Tucked away along Long Island’s South Fork, the Hamptons are known for their luxury and relaxation. The affluent beach community is popular with people looking to escape the summer heat of New York City and enjoy the stunning golden beaches along the Atlantic Ocean. Wind rustles the leafy green trees, and cool ocean waves lap along the soft sandy beaches. The Hamptons are filled with alluring estates tucked into the scenery, with private beach access and plenty of seclusion. It’s the perfect place to relax and enjoy amazing restaurants, high-end shopping, and charming beaches right outside of New York City.

It’s no surprise that with so much to enjoy here, the Hamptons are one of the best places to retire in the U.S. There are beautiful homes of all sizes, with easy access to enjoy the best parts of retirement, such as visiting the beach, relaxing on the golf course, and enjoying high-quality fine dining. Yet the Hamptons are just a short drive away from the glitz and glamour of New York City, making it easy to experience the theatre, restaurants, and culture whenever it calls.

If you’re curious about retirement in the Hamptons, this guide is for you. Our guide will walk you through the best neighborhoods in the Hamptons for a luxurious retirement and the best Hamptons real estate on the market.

#1 Westhampton

Westhampton is the perfect spot for those seeking a short commute from the city. This part of the Hamptons is closest to New York City, making the drive in and out a bit less arduous. Westhampton has the perfect mix of a small-town feel and glamorous, luxury living. There are stunning, large single-family homes along the famed Dune Road, each with personal beach access.

There’s also a cute downtown area filled with locally owned shops and restaurants, giving this part of the Hamptons a charming small-town feel. The quiet village streets that border Main Street feature cozy beach cottages just a short walk from the ocean and new-construction condominiums with modern amenities.

Westhampton Beach offers resort-style living and is filled with boutique shops and restaurants featuring local and international cuisine fueled by fresh, locally sourced ingredients. The real estate in Westhampton is some of the hottest in the area, and for good reason.

#2 East Hampton

East Hampton is one of the most exclusive areas in the Hamptons. This historical town has worked hard to preserve its small-town past while offering luxurious amenities that draw the most affluent clientele. Historic windmills and shake-shingle cottages line the streets that wind around the ocean, while the downtown brings a modern feel with boutiques and shops that rival anything offered on Madison Avenue.

The real estate in East Hampton is a collaboration of history and modern construction. There are beach cottages lining Egypt Lane with green lawns and manicured gardens, as well as expansive oceanfront mansions along Apaquogue Road. There’s something for everyone here, including some of the best beaches in the Hamptons, which continue to make East Hampton one of the most exclusive areas to retire.

#3 Southampton

Founded in 1640, Southampton is the epicenter of Hamptons beach living. There are miles of sandy shorelines and plenty of history preserved in the charming village architecture. The downtown area is situated around Main Street and Jobs Lane and offers charming boutique shops, high-end restaurants, and elegant shopping. The tree-lined streets are filled with beautiful, single-family homes showcasing manicured lawns and gardens. There are also plenty of expansive mansions along the coast with beachfront access to some of the best beaches in the Hamptons.

If you love private resort-style living, Southampton is the perfect location. Billionaires love the privacy and luxurious living Southampton affords, and many have private estates visited with their own helicopters via the village’s helipad.

#4 Sag Harbor

If you love boating life, then Sag Harbor is the perfect retirement destination for you. In the 1800s, Sag Harbor was one of the busiest ports in the country and was famed for its whaling business. Today, Sag Harbor remains one of the most historic areas in the country, and the charm of the old-world port still is maintained. The main streets are lined with mom-and-pop stores, classic bars and restaurants that serve American favorites, and lots of entertainment that keep the party going late into the evening.

Sag Harbor also has a literary past, as author John Steinbeck wrote “The Winter of Our Discontent” here. Today, the harbor is filled with stunning boats that allow visitors to experience the best of the Hamptons from the water.

#5 Montauk

Montauk is located along the easternmost tip of Long Island, and the rugged geography and varied waves draw many people to “The End,” from surfers enjoying the adrenaline rush of the cool Atlantic to artists trying to capture the never-ending beauty of the Hamptons. Montauk is a prominent commercial fishing village, making it a favorite for anyone who enjoys recreational fishing or boating.

In addition to the stunning rocky beaches, Montauk also offers golf, horseback riding, historical sightseeing, and opulent spa days. There’s never a shortage of things to do and enjoy when you retire in Montauk.

With so much easy access to both beaches and bays, Montauk real estate is in high demand. It’s a favorite destination with families, but it also draws a younger crowd that keeps the evenings lively and fun.

Enjoy your retirement in the Hamptons

If the amazing Hamptons real estate tempts you, you will want to work with a great realtor. In the Hamptons, one of the best groups is Midlam Ryan Team. The Midlam Ryan Team has extensive experience in the luxury market in the Hamptons and is ready to help you find the perfect retirement property.

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