By Emily Cahill
With irresistible summer weather around the corner, we’re edging closer to visions of carefree living in sumptuous style. While the Hamptons have long been a quintessential destination for sunbathing New Yorkers, we’ve chosen some of the most captivating retreats in New England and Westchester County to redefine the summer getaway. Skip the Hamptons traffic and ease into relaxation in the picturesque New York waterfront villages of Mamaroneck, Rye and Larchmont, where Long Island Sound beaches, boating, and world-class golf are merely moments away. For beach enthusiasts, the Connecticut shoreline beckons with its quaint coastal towns of Westport, Madison, and Stonington. If countryside living is more your speed, the bucolic Connecticut havens of Kent and New Fairfield boast sprawling lakefront estates, local wineries, and miles of postcard-worthy scenery. You’ll find a vibrant arts community and striking natural beauty in the Berkshires, which attracts visitors throughout the country for peaceful getaways.
As leading experts in luxury real estate, we’ve meticulously reviewed the region’s most remarkable offerings with consideration to amenities, style, and location. While blissfully secluded, each boasts an unbeatable proximity to New York City and Boston. Whether you choose to delight in a seaside beach home, historic cottage, or sprawling lakefront estate, here are the area’s top ten elite hideaways that lift summer living to new heights. From private docks and cabanas to neighboring yacht clubs and golf courses, these dreamy resort-style homes are guaranteed to leave a lasting impression.
1000 Old White Plains Road, Mamaroneck, NY
Reminiscent of an Adirondack chalet, this hillside oasis spans 11.45 acres in a secluded compound with its own private lake in Mamaroneck. “What I love most about my hidden retreat is that I feel like I’m on my own private island,” says owner James Giffin, “yet I’m only 35 minutes from my midtown Manhattan apartment.” From its stone and wood façade to dramatic vaulted ceilings, relaxing terrace and sparkling pool, the five-bedroom vacation home serves as the perfect year-round getaway. Graced by visits from corporate titans and heads of state, this legendary lodge-like estate is beautifully suited for entertaining, both inside and out. “I can drive a mile and a half and sail on the Long Island shore, but usually we just hang out and fish or kayak while marveling at the majestic beauty of our own scenic spring-fed lake,” says Giffen. If you do decide to leave your private paradise, savor world-class recreation at the illustrious Winged Foot Golf Club, located just steps away, plus marinas, yacht clubs and 11 golf courses within a five-mile radius.
803 The Parkway, Mamaroneck, NY
Live, play, and entertain in this exclusive summer escape. Prominently set in a premier coastal locale, this fully renovated sun-lit colonial is your key to lavish relaxation. While the private estate feels like a world away from city life, it’s barely a 35-minute train ride from Manhattan. “Why sit in traffic for 2+ hours to get out of the city for the weekend?” asks owner Lori Gelhard. “Come to Mamaroneck. It has a quaint town to stroll through, amazing restaurants, farmers’ markets, beaches, boating and golf, all a few minutes away.” Located in the sophisticated Shore Acres neighborhood, the home’s 6,000 square feet of living space offers the best in chic modern luxury. Terraces, a heated gunite pool, a covered porch, and sweeping lawns create a private utopia of unrivaled leisure. Move in and enjoy membership to the residents-owned Shore Acres Point Club with pools, a beach, boat slips, moorings, and new clubhouse just steps away. “We don’t have a vineyard down the road,” says Gelhard, “however, there is an excellent wine shop that delivers right to our door!”
Catch a glimpse of this beach lover’s paradise and you’ll know why it’s one of the most sought-after estates in town. Sequestered on a private peninsula in the exclusive Greenhaven section of Rye, this wonderful home enjoys complete seclusion – yet, it’s just 30 minutes to NYC. This sleekly renovated five-bedroom, five and a half-bath home reflects an innovative design with an open floor plan to capture scenic beauty from all principal rooms. Presiding over a protected shoreline lot, the waterfront grounds are enhanced by a unique dining terrace and entertaining patios. An available dock, mooring rights and large private beach are rarely offered in any area residence.
In its coveted waterfront setting, this gracious Georgian home resides in Larchmont Manor, one of the most sought-after private associations in town. “Pryer Lane is a special place,” says owner Suzanne O’Sullivan. “A place where you grow up actually knowing your neighbors. We had summer parties filled with kids, dogs, impromptu lawn baseball games, belly flop contests, firefly catching contests, and an annual 4th of July BBQ,” she recalls. Sited on more than an acre, this lakeside haven offers excellent seasonal recreation at Premium Mill Pond. “We grew up ice skating on the pond during the winters and kayaked and fished off the dock during the summers,” says O’Sullivan. Emerald lawns, an in-ground heated swimming pool and upper and lower entertainment terraces allow residents to savor spectacular sunsets over the lake. Built in 1911, the prominent, 6,000+ square foot brick residence greets with an impressive original leaded stained glass window along with a series of unique period details. “It’s an idyllic location,” says O’Sullivan. “A short distance from the city but feels a world away.”
82 Hartford Avenue, Madison, CT
Bask in resort-style summer living on the Connecticut shoreline. Located in the charming village of Madison, this breezy Colonial beach house rests on the sandy shores of Long Island Sound. An airy, open floor plan invites stress-free year round living with four bedrooms, sun-drenched living areas and unparalleled outdoor spaces. Savor the scenery with panoramic coastal views from a stunning wall of windows and expansive covered terrace. “You can listen to the waves and have a long nap in the shade,” says listing agent Margaret Muir. Set on more than 0.3 aces, this sun-filled gem is merely steps from an incredible private beach cabana. “Spend the entire day on the sand on this big beautiful beach in the fantastic beach cabana,” says Muir. “It has everything you need,” with a refrigerator, shower, toilet and electricity for complete convenience.
264 Taugwonk Road, Stonington, CT
A celebrated part of Stonington’s past, this 18th century Georgian Colonial upholds the style and sophistication of a bygone era. Wonderfully suited for a private summer retreat, the 12.05-acre pristine landscape exudes complete serenity with rolling meadows, stone walls, sprawling lawns, gardens and a private orchard. Known as Merry Meeting Farm, the estate is named after a freshwater tidal bay in Maine as a symbolic reference to periodic festive gatherings. The residence itself showcases a complete restoration with modern conveniences while preserving its historical significance. Period details, five fireplaces, beamed ceilings, and built-ins are combined with a new heated saltwater pool and top-of-the-line amenities. Several outbuildings include a caretaker’s cottage, heated 1,200 square foot barn, and a three-box stable. This iconic setting will be preserved by Stonington Land Trust for generations to come.
279 North Avenue, Westport, CT
Thirteen majestic acres comprise the setting for one of Fairfield County’s most extraordinary riverfront estates. Bordering the Aspetuck River, this pastoral sanctuary encompasses lush lawns, specimen plantings, an orchard, perennial gardens and 750 feet of spectacular river frontage. Inspired by an 1832 chestnut barn relocated from Weston, the distinctive main residence is an architectural masterpiece of incomparable design and dimension. Soaring ceilings, exquisite craftsmanship, and modern luxuries entice residents for sumptuous year-round living. Seasonal recreation and unrivaled amenities include a tennis court, enormous pool, pool house, gym, wine cellar and artist studio. A world away from city life, this enchanting hideaway conveniently lies midway between Boston and New York.
This stunning lake house is an outdoor enthusiast’s dream. With more than 700 feet of direct water frontage on North Spectacle Lake, the Kent home is completely upstaged by its surroundings. “Kenmont. The name says it all,” notes listing agent, Ira Goldspiel. “Own your own world and enjoy waterfront living, swimming, boating, and gazing at the water as the sunset changes it from blue to sherbet. The greatest value in Litchfield County of the year.” Inspired by the great summer homes on Nantucket, this shingle style residence presides over 72 acres on one of Connecticut’s few private lakes. The home highlights the interplay between natural elements and reveals an intrinsic balance of indoor spaces that emphasize the surrounding landscape. The idyllic compound features a private dock, expansive deck, fieldstone fire-pit, and boat storage. Ideal for a quiet summer getaway, the bucolic Litchfield Hills region boasts quaint vineyards, majestic nature reserves, and fabulous antique shopping.
124 Lake Drive South, New Fairfield, CT
This chic custom-built home is just as awe-inspiring as the landscape that surrounds it. Set at the edge of Candlewood Lake, the residence has been skillfully crafted to reflect its scenic surroundings. Floor-to-ceiling glass panels fill the 20-foot living room with natural light, while two floating staircases lead to the master suite, two additional en suite bedrooms and a state of the art media room. A covered patio streamlines outdoor entertaining with a built-in grill and pizza oven for lively al fresco dining. Dramatic western sunsets and sweeping lake views provide a dazzling backdrop to the modern residence. Embrace the laid-back lake lifestyle with a dip in the stone hot tub and a stroll to the sandy beach and dock. An added perk? The Candlewood Isle Clubhouse offers tennis courts, marina, basketball, bocce, and so much more.
With sweeping hills and lush woodlands, the timeless allure of the Berkshires embodies New England’s inimitable charm. Nestled in the town of Lenox, this lovely cottage retains its classic character while showcasing a stylishly updated interior. “We were drawn to the Berkshires for the local cultural attractions from Shakespeare and Company to Tanglewood and Canyon Ranch,” says owner Lee Munder, “along with all the charm and amenities of downtown Lenox.” Designed by prominent Boston architects Rotch & Tilden, the light-filled residence features beautifully scaled living spaces enriched with luxurious bespoke details. “We were fortunate to find an incredible property within walking distance to town that affords our extended family convenient access from both Boston and New York,” says Munder. “Our home really has it all — modern conveniences with historic renovations on nearly twelve secluded acres, yet right in the heart of Lenox and the surrounding community.” The private grounds envelop the home with exquisitely sculpted gardens, a dazzling pool and pool house. An original carriage house has been immaculately restored as a four-bedroom, three and a half-bath guest home with a wood-paneled great room, entertainment bar, two bedroom suites and a second floor guest apartment.
Access additional property information by clicking each link above. We invite you to contact the listing agents with questions or to schedule a showing to view these magnificent summer escapes. Keep an eye out for our next “Top Ten” list; until then, bask in the onset of summer!
