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Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village. This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away. The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches. Seasonal Rates: June $6,000 , July $8,000 , Aug-LD $10,000
…By Daniel Gale Sotheby's International Realty
2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!
…By Daniel Gale Sotheby's International Realty
Rental is Available in 2026: August $75,000. Located in our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities, top-of-the-line appliances, and walls of windows overlooking Coecles Harbor, this home has no comparisons. With 3,800 sq. ft., the home features an open floor plan with sweeping water views from every vantage point, whether dining, cooking, or lounging. Continue entertaining outside on the large outdoor waterfront deck where you become one with nature. The master and one of the guest bedrooms are en-suite, and the 2 additional bedrooms share a bath. All the bedrooms have abundant closet storage. Enjoy this newly constructed private waterfront property this summer!
…By Daniel Gale Sotheby's International Realty
Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered April $6,000; May $6,000; June $15,000; Sept $12,000. Permit #0483.
…By Daniel Gale Sotheby's International Realty
Welcome to 15 Lake View Court in Southampton, a fabulously reimagined pond front home. The vibe is lux organic, the palette soothing. With water-views from every room, it’s easy to embrace the Zen aesthetic. This east-west facing three bedroom, three bath has space to spread out, yet is ideal for gathering together. The upper level features a kitchen, dining, and main living areas, from which you can walk out and enjoy the deck overlooking Little Fresh Pond. This outdoor space is ideal for dining, gathering or relaxing. The lower level enjoys 3 spacious bedrooms with sublime pond views, sumptuous bedding and 2 additional baths. The fully landscaped and irrigated property offers privacy, a path to the water, a private dock, and of course a fire pit. Complete with water toys and fabulous proximity to both Southampton Village and Sag Harbor, this is a sought-after home away from home.
…By Daniel Gale Sotheby's International Realty
So much charm! This fully restored farm house is conveniently located just East of Love Lane and is set far back from the Main Rd offering a quiet country setting as it abuts preserved land to the East. The home has been recently restored and offers EIK, 1st Flr Master Bedroom w/ attached full bath. Living room and dining flow into one another creating an open floor plan. 2nd floor includes 3 additional bedrooms and full bathroom. Exterior features large wrap around deck off of Master Bedroom overlooking rear yard. Look no further for a North Fork year round rental!
…By Daniel Gale Sotheby's International Realty
2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully equipped open kitchen, and spacious backyard with a pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.
…By Daniel Gale Sotheby's International Realty
OFF-SEASON RENTAL | October 15, 2026 - May 15, 2027 Discover the tranquility of Westhampton’s off-season in this exceptional 2020-built contemporary residence at 50 No. Quarter. This immaculate 5-bedroom, 4.5-bath home offers the perfect blend of modern luxury and Hampton sophistication. The heart of the home features a stunning open-concept layout where a gourmet kitchen flows seamlessly into elegant dining and living areas—ideal for both entertaining and everyday living. Ascend to the third floor to find three beautifully appointed en-suite bedrooms, each boasting generous walk-in closets and private bathrooms. The fully finished basement provides versatile additional living space to suit your lifestyle needs. Step outside to your private oasis featuring a heated in-ground saltwater pool, offering a touch of luxury even during cooler months. This pristine property presents a rare opportunity to experience Westhampton’s serene off-season while enjoying all the amenities of a premier Hamptons residence. Available exclusively October 15, 2026 through May 15, 2027
…By Daniel Gale Sotheby's International Realty
2025 Availability & Pricing as Follows: Off Season October 1st - April 30th: $5,500/mo. Memorial Day - Labor Day: $45,000. May (Incl Memorial Day): $10,000. June: $12,000. July: $15,000. August - Labor Day: $18,000. September (not including LD): $10,000. Escape to the North Fork and enjoy the perfect blend of comfort & coastal living in this meticulously maintained 3-bed, 3-full bath home. As you step inside, you'll be greeted by living space adorned with nautical-inspired decor, plenty of natural light, and a gas fireplace. The fully equipped kitchen is a chef's delight, with stainless steel appliances and ample counter space for culinary creations. The open-concept design ensures a seamless flow between the kitchen, dining, and living areas, creating an ideal space for entertaining. Upstairs you'll find the primary king suite with views of Mattituck Inlet and a private spa-like bathroom off the expansive walk-in closet. Two additional well-appointed bedrooms, one w/ a queen bed, the other w/ a full bed, provide plenty of comfort for family members or guests. There's a pull out couch for overflow as well. Theater/media room in the basement, perfect for the rainy days or movie date nights. As you venture outdoors, a pristine landscaped backyard awaits, complete with a patio for outdoor dining, an outdoor BBQ area with a pizza oven, and a cozy fire pit. The home also has a pull out couch for additional overflow, two separate work spaces for those who need to work while on vacation, and split zone Sonos speakers throughout the house and in the backyard. Conveniently located near sought after Love Lane, several renowned wineries, farm-to-table restaurants, several local beaches, and more. Seize the opportunity before someone else does!
…By Daniel Gale Sotheby's International Realty
**2026 Rates** May $15K, June $18K, September 8-30 $12K, October $12K. This property is a stunning waterfront home located on West Cove in the exclusive Nassau Point area. Offering breathtaking views of the Great Peconic Bay, Robins Island, and New Suffolk, this home exudes charm and sophistication. The main level boasts two spacious great rooms, an enclosed three-season room, an eat-in kitchen, a dining room, and a primary en-suite bedroom. The finished basement includes two additional bedrooms, a full bathroom, and a media room, while the second floor features two more bedrooms and another full bathroom. The property's grounds are beautifully landscaped and elevated, with a mahogany deck, stone patio, outdoor dining area, and stairs leading to a raised platform beach with a pergola, providing easy access to the Bay for a refreshing dip.
…By Daniel Gale Sotheby's International Realty
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 gatherings. 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 September 2026 through April 2027 for $10K a month, this home is an exceptional option providing the perfect Hamptons home base.
…By Daniel Gale Sotheby's International Realty
Northport | WATERFRONT. Gated and enchanting waterfront retreat unlike no other. Fully FURNISHED & renovated Mediterranean inspired home nestled in the heart of Long Islands famed North Shore. Panoramic water views of the Long Island Sound & Connecticut. Foyer w/ sitting area and access to private deck. Open floor plan w/ views from every room. Large scale living/dining room combination. Upgraded EIK with stainless steel appliances. First floor w/ two en suite bedrooms and half bath. Lower level features large scale primary suite with renovated bathroom & steam shower. Additional en suite bedroom w/renovated bathroom. Lower level laundry w/ exterior access. The property features lush landscaping, in-ground pool and and covered cabana/ summer wet bar. Private Beach Access (HOA).
…By Daniel Gale Sotheby's International Realty
Experience luxury living in this beautifully renovated rental, ideally located near shops, restaurants, park, and access roadways for added convenience and enhanced quality of life. . This exceptional home features elegant finishes, modern amenities, and a thoughtfully designed layout. Wood flooring extends throughout the home, while the stylish living room is highlighted by a sleek linear gas fireplace. The custom kitchen boasts premium wood cabinetry, granite countertops, a six-burner gas range, and a charming breakfast area. A versatile first-floor bedroom offers the flexibility to serve as a guest room, home office, or den. The interior will be freshly painted before occupancy, providing a bright, move-in-ready atmosphere. The spacious primary suite includes a luxurious renovated en-suite bathroom with high-end finishes. Additional features include central air conditioning, a full basement for storage, and an attached two-car garage. Situated on a generous 0.54-acre lot, the property also offers a fully fenced backyard with beautifully manicured lawns, creating the perfect setting for outdoor relaxation and entertaining. Smithtown Schools
…By Daniel Gale Sotheby's International Realty
Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June $25,000; July 1-23 $27,000 (RENTED); Aug 1-15 $20,000; Sept 9-30 $18,000. Permit #1230.
…By Daniel Gale Sotheby's International Realty
Two week minimum rental. Available in July and August, $4,500 / week. August 16 through Labor Day, $5,500/week. 3% discount for rentals longer than 3 weeks. Perfectly situated in one of the North Fork's most desirable beach communities, this welcoming 4-bedroom, 2-bath, 2-story beach bungalow is just a 3 minute stroll to the sandy shoreline of Kenney's Beach, 7 minutes to the Great Pond, a 10 minute walk to McCabe’s beach and a 2 minute walk over to Little Fish restaurant. Oozing vintage beach-house charm, this gem makes for the perfect seaside getaway with family or friends where you can park your car and leave the city behind. What makes the house special is being surrounded by sandy outdoor space, the comfortable gathering spaces for family and friends, anchored by two levels of patio, an outside fire pit on the sand, and an indoor wood-burning fireplace for cooler evenings. It feels like your own private beach oasis and a private after-hours evening at the beach. The spacious main-level deck is ideal for al fresco dining after a day at the beach, and a private second-floor deck off one of the bedrooms where you can enjoy evening sunsets, and views toward Long Island Sound. Fire up the new grill after a day by the water, unwind with a good book on the deck, or grab the provided beach chairs and umbrella and stroll to Kenney's Beach for swimming, beachcombing, or simply watching the sunset. Beyond the neighborhood, discover the very best of the North Fork, from award-winning wineries and farm stands to waterfront restaurants, galleries, boutiques, and charming village centers. Other nearby favorites are Horton Point Lighthouse, a beach stroll that connects the coast from Horton’s Lane (one of the most picturesque inlets) to MacCabe’s and Kenny’s Beach (40 minute walk), easy hiking and walking trails at Goldsmith Inlet Park, and Little Ram Oysters farm stand. Close proximity to Greenport, East Marion and Southold. Whether you're planning a family vacation or a getaway with friends, this inviting Southold retreat offers the perfect combination of beach bungalow charm, comfort, convenience, walkability and the effortless coastal lifestyle that makes the North Fork such a special destination.
…By Daniel Gale Sotheby's International Realty
2026 Rates: August 1-15 $20,000, September $25,000, October $20,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4 spacious bedrooms—including a luxurious primary en-suite—and 3 full bathrooms, there’s plenty of room for family and guests to unwind in comfort. The heart of the home is a dramatic post and beam Great Room, designed for both relaxing and entertaining, with soaring ceilings and expansive windows that flood the space with natural light. Step out onto the large balcony to take in sweeping views of the Sound, enjoy morning coffee as the sun rises over the water, or end the day with a spectacular sunset. Additional amenities include a 1-car garage, central air, and thoughtfully landscaped grounds that ensure privacy and tranquility. Whether you’re lounging poolside, walking along the shoreline, or enjoying evening breezes from the balcony, this home offers an unforgettable seasonal escape.
…By Daniel Gale Sotheby's International Realty
Enjoy year-round living in this well-maintained 3-bedroom, 2-bath ranch offering a comfortable layout and recent updates throughout. The home features a recently updated kitchen with modern finishes and a beautifully renovated primary bathroom. An inviting all-season room provides additional living space, ideal for relaxing, entertaining, or enjoying the backyard in every season. The property offers a private dock, providing direct access to the water for boating, kayaking, paddleboarding, or simply enjoying the waterfront setting. The spacious yard is complemented by mature landscaping, creating a peaceful outdoor environment. Additional features include hardwood floors, abundant natural light, a private driveway, and an attached two-car garage. Conveniently located near shopping, dining, beaches, and other local amenities while offering the tranquility of waterfront living. Available for year-round lease.
…By Daniel Gale Sotheby's International Realty
2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy ambiance and an abundance of natural light. The home boasts stunning hardwood floors and is elegantly appointed with multiple living areas that provide the perfect balance of open space and private retreats. Ideally situated within walking distance of Kenney’s Beach, you’ll find yourself just moments away from charming local cafes, unique boutiques, renowned wineries, and exceptional dining options. This North Fork gem is truly the ultimate summer haven. Don’t miss your chance to experience the perfect blend of comfort and convenience!
…By Daniel Gale Sotheby's International Realty
Beautiful renovated 2-bedroom, 2 full bath home in Orient Village. Open concept – living/dining/gourmet kitchen. Lower level with screening room, office, full bath. Walk from Jitney. Enjoy all village amenities, bay & sound beaches. Close to Orient Beach State Park & Cross Sound Ferry. Available April $5,000; May $5,000; June $7,000; July $15,000; Aug $15,000; Sept $8,000. Permit# 1364.
…By Daniel Gale Sotheby's International Realty
Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings and filled with natural light and cooling breezes, the home is designed for effortless indoor-outdoor living. Spanning three floors and 2,600 square feet, it features 3 bedrooms, 4 full baths, and multiple spaces for gathering, entertaining, or quiet retreat. Enter from the spacious front deck, with seating for four and views of lush natural landscape and Sound. The main level comprises an open-plan living room with a wood-burning fireplace, dining area, eat-in kitchen, TV room, full bath, and a rear deck with dining table for six overlooking Great Pond. The ever-changing landscape of water, sky, and birdlife makes this a haven for nature lovers. Upstairs are two ensuite bedrooms, both enjoying beautiful water views and brand-new bathrooms, the one in the master suite benefiting as well from a long bathtub. The garden level offers a third bedroom, full bath, laundry area, movie and screening room, and an office/den with glass doors opening onto a rear deck with lounge chair, sauna, and outdoor shower. A private path leads directly to Great Pond, where kayaks and a canoe await exploration. Additional amenities include bicycles, a massage chair, piano, binoculars, telescope, and EV charger. Kenney’s Beach and the beloved Little Fish restaurant are just a short bike ride away, creating an exceptional blend of comfort, privacy, and outdoor adventure in the heart of the North Fork.
…By Daniel Gale Sotheby's International Realty
Summer Rental in New Suffolk! Enjoy summer on the North Fork in this well-appointed New Suffolk rental featuring partial water views, a spacious yard, and easy access to local beaches, dining, wineries, breweries, and farm stands. The home offers flexible living spaces, three bedrooms, two full baths, and multiple indoor and outdoor areas for relaxing and entertaining. Amenities include an eat-in kitchen, dining room, outdoor shower, charcoal grill, fire pit, washer/dryer, dishwasher, parking for four vehicles, and a large yard with outdoor seating. The first-floor layout includes a private bedroom, full bath, and adjoining sunroom, while the second floor offers additional bedrooms, a full bath, and a separate lounge area. Conveniently located near New Suffolk waterfront attractions and just minutes from the many vineyards, restaurants, and recreational opportunities throughout the North Fork. Summer 2026 Availability -June (2 week minimum) - $3000 per week, July and August (2 week minimum) - $4000 per week
…By Daniel Gale Sotheby's International Realty
Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.
…By Daniel Gale Sotheby's International Realty
Escape to your own piece of paradise in this stunning bayfront home, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or heading down to the beach to dip your toes in the sand. This home is a true oasis, perfect for outdoor entertaining and water activities. Whether you're swimming, kayaking, paddleboarding, or simply lounging on the giant anchored raft, there's something for everyone. The lush, hydrangea-filled gardens provide a sense of privacy and serenity, making this retreat incredibly enticing. With two spacious living areas and options for dining indoors or out, this home is designed for both relaxation and entertainment. Enjoy cozy evenings by the beach or star gazing, roasting marshmallows over a fire and making memories to last a lifetime. Discover the perfect North Fork getaway, where charm, character, and coastal living come together in harmony. Permit # 24-3065
…By Daniel Gale Sotheby's International Realty
Recently Remodeled Colonial Home on 2 Acres of Property Overlooking the Nissequogue River with Rocking Chair Front Porch. Many Updates Include New Roof, Siding, Driveway, & Eat In Kitchen. Freshly Painted in March 2026 with Refinished Wood Flooring. Den w Wood Burning Fireplace, Updated Bathrooms, Full Basement, 2 Car Garage. Rear Yard is Surrounded by Mature Trees and is Tranquil and Serene. Nearby are Local Beaches, Hiking Trails, Fine Dining, Local Shopping, and Stony Brook University and Medical Center. Smithtown Schools.
…By Daniel Gale Sotheby's International Realty
Discover the finest rental that Quogue Village has to offer. A Contemporary with Zen vibes, offering 5 bedrooms, 5.5 baths an open floor plan that opens to a dining room to entertain over 10 guests. Chef's kitchen has 2 ranges, a 4-burner gas range and a Viking 6 burner gas range, sub-zero refrigerator, 2 dishwashers, and of course, a wine refrigerator. To top it?off, an island with seating for 6 adds more entertaining space. First floor ensuite bedroom, second floor, primary ensuite with private balcony, designer bathroom with soaking tub, walk-in shower. The fully furnished lower level offers media room, full scale gym, and wet bar. Outside enjoy the heated Gunite pool, tennis, and a hard court with basketball hoop. the 16x16 gazebo offers a fireplace for those special evenings in the Hamptons. Option to rent "mini moke" for those drives to the exclusive Quogue Village Beach. What a spectacular summer in Quogue. Available July 2026 only
…By Daniel Gale Sotheby's International Realty
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