On the Market: Poolside Living in Connecticut, Massachusetts & New Jersey
by Grace Cassidy
June 2025
358 Lukes Wood Road, New Canaan, Conn. | $10,995,000 | Jennifer Crowley
Found in beautiful New Canaan, this 1941 home offers over 16,000 square feet of interior living space with seven bedrooms, eight full bathrooms, and three half-baths. Residents will love the original details including the reclaimed oak flooring imported from France, custom millwork, fireplaces, and high ceilings. A golf simulator and putting green, bar, gym or yoga studio, wine cellar, and home theater are found in the finished lower level. The property spans nearly five acres and is complete with a guest house, sparkling pool, renovated barn, sport court, and tennis court.
51 Oenoke Lane, New Canaan, Conn. | $4,395,000 | Melissa Engel
Originally built in 1938, this renovated home offers the best of historic charm and modern convenience. Spanning 5,844 square feet are six bedrooms, five full bathrooms, two half-baths, fireplaces, hardwood flooring, stylish built-ins, a well-equipped kitchen, and a finished lower level with additional living and entertaining space. Outside, the 1.15-acre property features an expansive patio complemented by a fireplace, spacious lawns, beautiful gardens, a cabana, and a pool that’s perfect for cooling off in the warm summer months.
180 Ash Street, Weston, Mass. | $38,000,000 | Mark Doherty
Sited on nearly 19 acres of land in Weston, this 21,000-square-foot, six-bedroom, 12-bathroom estate is the ultimate experience in luxury living. High ceilings, custom moldings, wide windows, and grand entertaining rooms come together to offer an elegant and refined mansion. Other features include a generous chef's kitchen, two offices, a sunroom, and a luxe primary suite with dual dressing rooms, private sitting room, office, and spa-like bathroom. Enjoy entertaining during the summer in the screened-in porch with a built-in grill and fireplace complemented by sprawling grounds with a sparkling pool, pool house with kitchen and bathroom, basketball court, and oversized four-car garage.
8 Conant Road, Weston, Mass. | $8,999,999 | Megan Francese and George Sarkis
Dating back to 1931, this Tudor Revival-style home offers great charm and curb appeal. The 7,382-square-foot retreat has five bedrooms, five full bathrooms, four half-bathrooms, custom design work, fireplaces, large windows, and a chef’s kitchen with top-line appliances and a spacious center island. The three-acre property will be the place to entertain during the summer with a beautiful pool, lush gardens, patios, a full cabana, and outdoor shower. A renovated detached carriage house includes an apartment, gym, and steam room – and a custom-built treehouse with electricity.
10 Maxey Pond Road, Nantucket, Mass. | $15,995,000 | Nicole Tirapelli and Michael Passaro
Located on beautiful Nantucket, this three-acre property offers a brand-new 7,200-square-foot home with six bedrooms, six full bathrooms, and three half-baths. The adjacent 20-acre land bank property offers great privacy and beautiful views over Maxey Pond, plus distant ocean views and gorgeous sunsets. Tall ceilings, wide windows, and an open floorplan define the newly constructed estate, complete with desirable features such as a chef’s kitchen, butler’s pantry, entertaining spaces, sustainable design, and solar power. Summer entertaining is a breeze with an incredible outdoor space outfitted with a saltwater pool, oversized jacuzzi, landscaped grounds, and lawn space perfect for croquet and badminton.
27 N Ward Avenue, Rumson, NJ | $11,995,000 | Suzanne Veninata
With over 17,000 square feet of interior living, this Rumson estate (above, bottom) offers expansive gathering spaces for residents and their loved ones, providing seemingly endless room for entertaining. The home features eight bedrooms, nine full bathrooms, four half-baths, fireplaces, arched windows, a spacious well-equipped kitchen, and a luxurious primary suite. Sited on 3.25 gated acres, residents will appreciate the 120 feet of private water frontage, beautiful grounds, a resort-style pool, pool house, generous patio, fire pits, manicured lawns, and ocean views.
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