luxury property with pool for rent Orient, United States

AVAILABLE FOR THE MONTH OF AUGUST. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

AVAILABLE FOR THE MONTH OF JULY. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

AVAILABLE FOR THE MONTH OF JUNE. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

AVAILABLE EARLY SEPTEMBER TO THE END OF MAY, 2027. Classic Madison charm meets modern family living in this inviting 4 bedroom Colonial on Wildcat Road. Step through the front door to discover hardwood floors that flow throughout, two fireplaces that add warmth and character, and an extra-large (front to back) Living Room perfect for gatherings large and small. Gardeners will love the Greenhouse, right off the Dining Room! Just off the Living Room leads to a delightful screened porch-ideal for morning coffee or summer dinners-and a spacious patio for outdoor entertaining. The walk-out lower level is completely finished and currently serves as a generous family room, offering a wood burning stove, spacious laundry area, flexible space for play, relaxation, or entertaining. Located close to Madison's charming town center and the Town Campus, this home delivers both convenience and community. As a special bonus, enjoy access to the inground pool next door-a rare perk that makes summer living effortless. Whether you're hosting friends, enjoying quiet evenings by the fire, or exploring all that Madison has to offer, this home provides the perfect backdrop for everyday life and lasting memories.

July is available at $20,000/mo. August has been rented. Also available for April, May and June at $12,000/mo. Academic available at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning 4-bedroom, 5.1-bathroom shoreline retreat. 52 Kelsey Place features a chef-inspired kitchen, central air, 2-car garage, large patio with fire pit and BBQ, inviting fireplace, luxurious steam shower in primary bathroom, outdoor shower, and more. Perfect for entertaining, with room for everyone!

Year-round at $7500/mo or Academic at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning 4-bedroom, 5.1-bathroom shoreline retreat. 52 Kelsey Place features a chef-inspired kitchen, central air, 2-car garage, large patio with fire pit and BBQ, inviting fireplace, luxurious steam shower in primary bathroom, outdoor shower, and more. Perfect for entertaining, with room for everyone! Also available for April, May and June at $12,000/mo and or July and August for $20,000.

Available for April, May and June at $12,000/mo. Could be available year-round at $7500/mo or Academic at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning 4-bedroom, 5.1-bathroom shoreline retreat. 52 Kelsey Place features a chef-inspired kitchen, central air, 2-car garage, large patio with fire pit and BBQ, inviting fireplace, luxurious steam shower in primary bathroom, outdoor shower, and more. Perfect for entertaining, with room for everyone!

STILL AVAILABLE FOR LAST TWO WEEKS OF AUGUST! Panoramic vistas of Long Island Sound and the East River create a breathtaking backdrop for this sophisticated Madison waterfront retreat. Designed for elevated coastal living, the sun-drenched open floor plan flows effortlessly from the main living spaces to expansive water views beyond. Offering 3 bedrooms and 3 full baths, the home comfortably accommodates 8+ guests with thoughtful design and generous gathering spaces. Enjoy easy access to shoreline beaches, perfect for morning swims and evening strolls along the water, while the private heated pool provides a serene setting for long summer afternoons under the Connecticut sky. Available weekly for the last TWO weeks of August at $8,000 per week. A rare opportunity to experience Madison's shoreline lifestyle at its finest - where timeless waterfront beauty meets effortless summer luxury.

Discover the perfect blend of antique charm and modern convenience at 50 Ledge Hill Road. This delightfully updated and maintained antique colonial is available for annual rental, offering a truly peaceful and picturesque retreat on six and a half acres of serene land. Despite the feeling of total privacy and seclusion, you'll remain conveniently located within a fifteen-minute drive of all local amenities. The home features three bedrooms and one and a half baths along with ample living space: a dedicated living room, a comfortable family room, an office, and a den, providing flexibility for working from home or hosting guests. The charming, eat-in kitchen is pleasantly sized, perfect for casual, everyday dining or holiday gatherings. Step outside and enjoy the expansive, sprawling backyard, featuring an inground pool for fun all summer long. The home also features brand-new central air conditioning and landlord-maintained solar energy and professional landscaping. With its blend of historic character, abundant space -inside and out, wonderful amenities and prime location, 50 Ledge Hill Road is a renter's dream. Don't miss this unique opportunity-schedule your private tour today.

Spend your summer in the heart of Westhampton Beach at 9 Ocame Avenue — a chic, four-bedroom, three-bath retreat designed for effortless coastal living. This bright and stylish home offers the perfect blend of charm, comfort and Hamptons convenience, all moments from Main Street, world-class beaches, boutiques and dining. Step inside to sun-filled living spaces, a well-appointed kitchen, and comfortable bedrooms ideal for hosting gatheirngs. Outdoors, enjoy everything that makes summer special: a welcoming front porch, patio for dining and lounging, sparkling pool, pool house and a refreshing outdoor shower for after beach. Available June, July, and August, this home is an exceptional option for those coming out for the U.S. Open in June—providing the perfect Hamptons home base within close reach of Shinnecock Hills and all the excitement surrounding tournament week. Available 2026: June-July $52, June $20k, July-LD $70k, July $34k

Available for an exceptional summer residency, Bois Dor is one of Newport's most distinguished 1920's era estates offering a rare opportunity to live within architectural history while enjoying modern luxury. Beyond its storied linden allee' entrance, this manor house unfolds across elegantly restrained formal rooms including soaring ceilings, and extraordinary period detail. Sunlight pours through oversized French doors, illuminating the elegant salon, garden loggia and dining room. It also sports the largest private ballroom in Newport which opens out to the 66' ft long pool, perfect for entertaining. The manicured gardens, sweeping lawns and natural meadow create a secluded retreat just moments from Bellevue Avenue and the harbor. The heated pool and terrace provide a resort-like setting for summer entertaining from champagne afternoons under the coastal sky. The estate offers generous bedroom accommodations for 20 (including 5 ensuite), multiple entertaining spaces, and a seamless blend of historic grandeur and contemporary comfort. Whether hosting intimate gatherings or enjoying quiet mornings on the grounds, Bois Dor delivers an incomparable Newport lifestyle. Resort-style pool & terrace, Grand ballroom & formal entertaining rooms, Expansive landscaped grounds, Prime Newport location near Bellevue & beaches and Central Air conditioning. A once-in-a-generation summer offering for the most discerning resident seeking legacy, privacy, and architectural distinction.

Available for an exceptional summer residency, Bois Dor is one of Newport's most distinguished 1920's era estates offering a rare opportunity to live within architectural history while enjoying modern luxury. Beyond its storied linden allee' entrance, this manor house unfolds across elegantly restrained formal rooms including soaring ceilings, and extraordinary period detail. Sunlight pours through oversized French doors, illuminating the elegant salon, garden loggia and dining room. It also sports the largest private ballroom in Newport which opens out to the 66' ft long pool, perfect for entertaining. The manicured gardens, sweeping lawns and natural meadow create a secluded retreat just moments from Bellevue Avenue and the harbor. The heated pool and terrace provide a resort-like setting for summer entertaining from champagne afternoons under the coastal sky. The estate offers generous bedroom accommodations for 20 (including 5 ensuite), multiple entertaining spaces, and a seamless blend of historic grandeur and contemporary comfort. Whether hosting intimate gatherings or enjoying quiet mornings on the grounds, Bois Dor delivers an incomparable Newport lifestyle. Resort-style pool & terrace, Grand ballroom & formal entertaining rooms, Expansive landscaped grounds, Prime Newport location near Bellevue & beaches and Central Air conditioning. A once-in-a-generation summer offering for the most discerning resident seeking legacy, privacy, and architectural distinction.

STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a comfortable and chic look. Long distant views and rolling, verdant lawns add to the magic of this property. Close to top restaurants, art galleries, shopping and outdoor recreation. Only 90 minutes to NYC. Note: Field card indicates that there are 3 bedrooms but the house has 4 bedrooms and a 1250 tank.

A quiet country lane near the Lake Club (pool lake and tennis club) introduces this lovely Colonial set back on a beautiful, level property. The desirable open floor plan encompassing a warm and inviting kitchen and family room w/ a stone fireplace encourages lingering and relaxation. The gracious living room also with a fireplace and an expansive dining room are perfect for more formal entertaining. A large bonus room, 1st floor office, laundry and mudroom complete this level. The master suite enjoys a full bath and walk-in closet. Down the hall are three additional bedrooms and large hall bath. Finished walk-out lower level. Convenient location.

198 Hemlock Hill Road, New Canaan, CT. Perfectly blending classic charm with high-end amenities, this home offers a private summer escape, just moments from the heart of town on desirable Hemlock Hill. Enjoy 2.5 acres of sweeping lawns and secluded pool. This special property offers many lovely outdoor spaces to enjoy, the inviting covered porch, complete with Adirondack chairs and dining, convenient stone terrace with wood burning fire pit and of course, poolside relaxation. This private pool retreat features a seasonal changing cabana with outdoor shower, half bath and laundry facilities. Warmth and charm welcome you indoors. The well appointed kitchen and family room are open and inviting, the nucleus of this home. A sunny breakfast nook and fireplace complete this gathering space. Four additional fireplaces, including the private wood panelled study, library, living room and primary suite. The primary suite has tray ceilings, door to deck, lovely bath and a handsome fireplace. There are 3 additional bedrooms (one ensuite) and two baths on the second floor. On the third floor, two more delightful bedrooms and bath, ideal for guests or a quiet getaway. Enjoy a peaceful summer in New Canaan on Hemlock Hill!

TIME TO PLAN YOUR SUMMER VACATION! OR RENT YEARLY! Available June and July. Call for Summer Pricing! Enjoy country living in this stunning location with spectacular views and total privacy. Only 90 minutes from NYC. Swim in the heated gunfire pool. Explore the homes 142 acres. Plenty of room for family and friends who want to experience the beauty of Litchfield County. There is a 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and 4 Full baths. Can sleep 19 with every bed filled. Explore 142 acres of open fields and forest. The house has a chic modern interior that is tastefully decorated. There is easy access to Litchfield County's many private schools. Enjoy the hiking trails at local land trust, canoeing or kayaking on the Housatonic river or Lake Waramaug. There are country fairs, art shows, local theatre, great restaurants and many fine shops to explore. Available starting September $12k per month for yearly lease. Call for Summer Rental pricing. Minimum 24 hour notice to view.

Welcome to this stunning furnished 1999 Colonial situated on 2 picturesque, level and private acres. Outdoor features include a heated gunite pool/hot tub, stone terraces and a summer kitchen. A gracious entry hall offers a view through arched entry into the formal dining room. An elegant living room with fireplace and adjacent terrace connects to the office. The gourmet chef's kitchen opens into the breakfast area and Family room. French doors throughout the 1st floor and garden level offer access to the stone patios, summer kitchen and gorgeous grounds. A dramatic curved staircase leads to a stately Primary Suite with fireplace and balcony and 4 additional bedrooms, 3 of which are en suite. The lower level offers a 2nd family room and accommodates exercise, art projects and has a bedroom and full bath. This home abounds in luxuries and is ideal for cozy family events as well as large-scale entertaining. The ideal location is convenient to schools, the Purchase Community House, train stations and the Towns of Rye, Harrison and Greenwich. Come and take a look. You won't want to leave!