North Haven NY Real Estate & Homes for Rent

Nestled in the charming enclave of Sag Harbor, 15 Mt Misery Drive offers a perfect blend of tranquility and sophistication. This thoughtfully designed property features 3 bedrooms, 3 bathrooms, and a chic style throughout. Enjoy the seamless flow of indoor-outdoor living, with an expansive back deck for lounging or grilling and fire pit set beside the tranquil koi pond. Relax in the privacy of Sag Harbor south with close proximity to downtown Sag Harbor, Wolffer estates and Bridgehampton. 15 Mt Misery Drive is the perfect summer getaway in Sag.

Lovely Hay Beach Home with Pool. Nicely appointed seasonal 4 bedrooms, 3 bath home with in-ground 9' diving pool awaiting your arrival. Spacious home on a shy acre with deck and patio for outdoor entertaining. Close to beaches, shopping, restaurants and ferries to both forks! Come to Shelter Island this summer and enjoy the natural beauty of it all~ Fire pit, gazebo, chairs, and lounges are included. Well-behaved dog-friendly home. Permit # 2023-V-0005

Large and bright 4 bedroom, 2.5 bath home with pool in a private waterfront community. Property has path that brings you ten houses from the most beautiful beach. A great place to spend any season and year-round. Great open kitchen with table that seats 8. Adjacent to the dining room which can seat 10+. Host the holidays. Primary suite is oversized with a seating area and a separate sunroom. Upstairs are all of the guest rooms and a den. The property is just shy of 3 acres and offers plenty of room to roam. A great escape from the city, and a tranquil place from which to work. Available multiple time periods; any two available weeks in the summer $8k/week, July12- Aug 8 $30k, Sept.3-30 $25k, Oct. $20k, Nov. $20k, Winter Sept. 3- May 1 $48k, may be available year-round after Labor Day.

Privacy abounds in this beautifully renovated Wainscott traditional home. Sited on 5.5 acres with deco turf tennis/basketball this 4500 Sq ft with 2500 sq ft lower level 7 bed /6.5 bath is the perfect summer rental. As you enter the grand open living areas, you are greeted with tons of natura light from a wall of French doors that open to expansive outdoor deck area. The living room flows into dining area and huge eat in renovated chef's kitchen with island seating, marble counter tops, stainless steel appliances and breakfast area with window seating. Bedrooms and baths consist of a first floor primary suite with vaulted ceilings, access to the backyard and a renovated expansive en -suite bathroom. There is another main floor bedroom as well. The second floor boast an additional primary bedroom with double granite vanity and soaking tub and access to a 2nd floor decked balcony. There are 3 other oversized en-suite guest bedrooms. The newly finished lower level consists of two more bedrooms, movie/media room and gym. The back deck has expansive covered seating and dining areas with outdoor kitchen with DCS grill that looks onto a beautifully landscaped yard and 20X40 heated gunite swimming pool. Beyond the pool lies the tennis court with basketball net that is perfect for all sports lovers. Other features include a new Jacuzzi, a two-car garage, and an outdoor shower. There's easy access to East Hampton and Sag Harbor villages! Awesome location and close proximity to both bay and the ocean beaches.

AVAILABLE JULY, 2024 (open to first two weeks of Aug-inquire for pricing). Located off a quaint private road this stately +/- 4,790 square foot 5 bedroom, 4.5 bath home makes for a fabulous retreat that can be enjoyed 365 days a year. Boasting a free-flowing, versatile floor plan that feels 'just right,' guests are met with a stunning double height entry hall giving way to a two-story great room accented by soaring ceilings and partial bay views. Prime for entertaining yet spacious enough to offer privacy for one and all, no detail was spared in this masterful build. Standout features include two primary bedroom suites (one upstairs, one downstairs), three guest bedrooms, gourmet kitchen, 800 square foot bonus room, screened in porch, palatial deck leading to a heated pool, Har-tru tennis court, bay views from the 2nd floor, and private access to a secluded bay front beach with the ability to moor a boat. 4-Zone central air/heat, 2,200+/- square foot basement, and 2 car garage. 16 Bittersweet is filled with sunlight from oversized multiple windows and is ready to make you feel right at home. Minutes to Sag Harbor, Bridgehampton, and Water Mill.

Available for the delightful North Fork off-season, this impeccable modern 3 bedroom 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a primary suite, all have water views. The private bay beach is a short stroll away. Easy access to renowned North Fork wineries, farmstands, restaurants and shops. Winter $6000 per month.

Over 5 Acres of Perfection with Tennis! Available for last 2 weeks of August for $56,000. Terrific location with convenient access to Sag Harbor Village, East Hampton Village and ocean beaches. Sited on 5.4 +/- acres and adjacent to a 24 acre reserve, this home has all of the amenities that are sought after in a Hamptons summer home. A dramatic entry foyer leads to the spacious double height living area with fireplace, dining area, an open up to date chef's kitchen, that are all highlighted by walls of glass bringing the outdoors in. There are a total of 5 bedrooms and baths including 3 stately suites. The finished lower level is complete with a tv lounge and gym. Once outside enjoy a heated swimming pool and spa, outdoor shower, all weather tennis court with separate basketball court. The home itself is a meticulously maintained 3,800+/- sq. ft Pos Modern style home that is uniquely crafted for entertaining and privacy. The driveway has ample space to park and the approach to the home is beautifully landscaped. This vacation home will become the one you will come back to year after year. Recently decorated by Restoration Hardware, relax and take in all that summer has to offer!

The perfect summer spot ! Plenty of room in this beautiful home and enjoy the Reydon Shores private beach too! This comfortable home features a spacious kitchen which leads out into a grand deck for outdoor dining. There are 4 bedrooms and 3 bathrooms which includes a first floor master bedroom en-suite, living/dining room and a large family room. The amenities continue outside on the park-like backyard setting with an outdoor shower, basketball hoop, badminton and ping pong. The home is located just 9 homes away from the beach - 2 kayaks included. Available starting Sept $7,000 off season months $3300. Southold Town Rental Permit #0641

ALL NEW EAST HAMPTON 9.2acres RR# 22-1028 This is one of the most beautiful houses in the Northwest offering 5000+/- sq ft situated on 9.2 privates acres, minutes from the Village and beaches. The light filled entryway leads to an expansive main floor featuring a very gracious open living area with a state of the art kitchen, counter seating, breakfast nook, adjacent intimate seating area, a living room with a two-sided fireplace, and huge formal dining room easily seating 12. The main floor Primary Suite includes an oversized sleeping chamber with tons of glass and light, The ensuite spa bathroom, separate private home office space, and custom walk-in closet, adds to the elegance of this gracious home. A powder room, pantry and mudroom complete the first floor. Up the stunning open staircase you reach the 4 guest bedrooms with two baths, one on either end of the large hallway. Back to the main level through a glass atrium just above the attached 2 car garage is the BONUS BUNK/MEDIA/GAME ROOM with its own full bathroom, great for overflow, guests or a teens dream. Outside there's a large attached deck area off the living area with ample seating and an oversized table for al fresco dining, a gigantic grassy yard leading to the resort style heated swimming pool with lounging for many, is adjacent to a pool cabana with a half bath, outdoor shower and wet bar. This is elegant comfortable yet easy living. You will never want to leave! Listing ID: 891772

Beautiful and inviting are words that come to mind when describing this welcoming vacation home in the charming private beach community of Paradise Shores. Only 200' to the community's private beach, and picnic area, the home has water views, 5 bedrooms, 2 baths, a screened in porch for lazy days, an upstairs balcony to take in the view, a large outdoor shower w/changing room, an outdoor kitchen on the back deck for entertaining and a cozy firepit area. Central air and ceiling fans in each bedroom for comfort. All tastefully decorated with a relaxed vacation vibe. Oh, and Kayaks are available too! Every inch of this home feels like your dream vacation! (Southold Town Rental Permit #0984). 2024 Rates: June $16k or $4k/week, July $25k or $5k/wk, First 3 weeks in August $6k/week. September, after LD, $4,500/week. Two week minimum applies to all stays.

Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street. There are three bedrooms, two full bathrooms, open floor plan from kitchen through the dining area into the vaulted ceiling living room, Enjoy the beautiful screened in porch which overlooks the private back yard with slate patio, grass lawn, and outdoor shower. Prime location for easy access to numerous beaches, wineries and town shops, restaurants and transportation. Off season, summer season and weekly (2 week minimum) available. Weekly $3000, June $7,500, Off season $5000 Southold Town Rental Permit #0600

Welcome to this fabulous vacation home located at 1275 The Esplanade, in Southold's coveted "Angel Shores" private bay beach community. The private bay beach is so close you can hear the waves and feel the bay breeze from your porch. There is a glorious free form, heated, saltwater pool, with a sparkling fountain and waterfall. Outdoor shower, patio fire pit, BBQ and plenty of outdoor lounge areas complete the private backyard. The interior is stunning! Stylish decor and furnishings, central air and a house generator, a huge sun room that overlooks the pool. Sleek and spacious rooms, with hardwood floors throughout. The first floor was totally renovated , completed in April 2024. The large kitchen has quartz countertops and high-end appliances, open concept living room, spacious dining area, and a brand-new powder room. The second floor was renovated in 2023 with upscale spa like bathrooms and a second-floor laundry room for your convenience. The finished lower level has an entertainment area and game room with a pool table and arcade game. Also, there are 3 kayaks and 5 bicycles available for you to fully enjoy all the North Fork has to offer. Available 2024 ...April $8,500, May $8,500, Memorial Day Weekend Thru June $16,500 (5 Weeks). Your Best Summer Vacation Poolside and By the Sea Shore!

Beautiful Post and Beam located in sought after Landfall Association in Northwest Woods. This impressive four bedroom three bath home has soaring ceiling that spill in warm beams of light from the expansive windows. The bedrooms are cozy and restful for family and friends. A bonus loft area is ideal for rainy day projects. A heated 20x40 pool adds to an afternoon of bbq's parties and in the dog days of summer there is also an association beach access perfect for paddleboarding and swimming. Quiet, relaxing and the perfect home to unplug!

This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach! Surrounded by marinas, award winning vineyards, restaurants, farm stands & great shopping. Make this absolutely mint home your North Fork summer rental, you will not want to leave! Permit #1002

Upon entering this recently renovated home, you are immediately impressed by the open, airy design with vaulted ceilings providing ample natural light and a spacious feel. This exquisite contemporary home boasts 3 bedrooms and 3.5 bathrooms, a sun-drenched family room with two-story windows, hardwood floors throughout and partially finished basement featuring a game room and bar, full bathroom, and additional space for entertaining. A separate office with a sofa bed and WiFi throughout the home is available for those who need to stay connected during their stay. The primary bedroom features an en-suite bathroom with an oversized shower along with a large walk-in closet. Sliding doors from the primary suite and family room lead to the large deck overlooking the heated pool and professionally landscaped one-acre lot. Outdoors, you will find an outdoor shower, perfect for rinsing off after a day at the private beach just a stone's throw away from the property. The home is also in close proximity to a nature preserve, providing a serene environment for a morning walk or run. This stunning contemporary residence is fully fenced and features a gated driveway for added privacy and security. Located just minutes from transportation, schools, parks, shopping, and restaurants, this home is truly the ideal place to call home during your summer vacation. Now available July $45k, August $45k, August-Labor Day $52k, July/August - Labor Day $97k

Summer Beckons At This Spacious Retreat In A Private, Park-Like Setting In A Very Desirable Cul-de-Sac Community Of Southold. Featuring Large Gunite Swimming Pool, Deeded Beach, Multiple Bedrooms, Large Sun-Drenched Living Areas That Open To Backyard. Rental Available First 2 Weeks Of August. Come And Get It. Permit#0848

Newly Renovated Unit W/Spectacular Views Of Bay, Beach & SI Beyond. 2 Bed/ 2 Bath. Styled Elegantly. Open Plan W/ Views From Every Window. Waterfront Balcony On Beach. Complex has a Waterfront Pool, Tennis & Pickle Ball Court & Over 200 Ft of Bay Beach. Rental Includes a Boat Slip in Marina. In Heart Of Village. Close To Restaurants, Transportation, Ferry & Shops. (Southold Town Rental Permit #21-063) June $13500; July $18500; Aug-LD $23000.

Trees, foliage, and a long driveway await you as you open the gates to 170 Northside Drive. Located Conveniently 5 mins to Sag Harbor Town Beach! As the door opens, you are greeted by a grand foyer with vaulted ceilings and an elegant chandelier. Off the foyer is a living room with a wood-burning fireplace, a gracious dining room with floor-to-ceiling French doors leading to a stone patio, an office and a guest powder room. Not to be missed is an open kitchen and dining area which enjoys views of the rear garden and pool. Off the kitchen sits a beautiful great room with another wood-burning fireplace, wet bar, mini-fridge, and wood shelving for your entertaining convenience. As you travel to the upper level landing, you experience a sense of balance, openness, and light-architecture at its best-with three bedrooms, two bathrooms (en-suite in master), and a large laundry room with a window of its own. Each level of this home opens to the outside area that looks at beautiful gardens. The middle and lower levels are fitted with French doors and the upper level with an extensive terrace. On the lower level, a beautiful Japanese garden and pond are adjacent to an apartment of its own with a bedroom, office, a full bathroom, a recreational room and a pool table too! A two car attached garage leads out to more arbor beauty. If this is not enough, come and enjoy the 20x40 pool-lounge and relax in a magnificent pool house, equipped with kitchen, fireplace, and living area.

Escape to the breathtaking beauty of the Hamptons and indulge in the ultimate vacation experience! This stunning property offers the epitome of luxury living, whether you're seeking a month-to-month rental, a summer escape, or year-round bliss. Step into a world of elegance and comfort as you enter this spacious, bright, and immaculately maintained home. The open floor plan and soaring vaulted ceilings create an atmosphere of grandeur and serenity, while the generously sized rooms provide ample space for relaxation and entertainment. Summer Rental, month to month,, or year round! Find yourself enjoying the beautiful vacation life that the Hamptons has to offer! Super spacious, bright, clean, open floor plan and vaulted ceilings with generous sized rooms. All 4 Bedrooms have ensuite baths. Exercise room complete with equipment, sauna makes this retreat the perfect quintessential vacation home. Private Heated Pool (Seperate Charge). with spacious deck for outdoor dining and entertaining or just chaise lounging. Located between Southhampton, Bridgehampton, and Sag Harbor Village which is the closest. All Beaches are also nearby!

Ideally located between the villages of East Hampton and Sag Harbor is the perfect summer getaway for family and friends. Take the 375-foot-long private driveway to this beautiful and secluded 4,800 sq ft home, situated on a quiet 1.5 acres that has so much to offer by way of both luxury and entertainment. As you enter the house there is an expansive great room filled with natural light. The open kitchen was designed with a great open floor plan which is perfect for entertaining. The main floor primary bedroom is en suite with a private deck, walk-in-closet, double sinks and a soaking tub. There are 3 additional en suite guest bedrooms that are all nicely-appointed on the main floor. The finished lower level with full egress is a wonderful bonus. There is an oversized en suite guest bedroom, home theater, office space, wet bar, cedar closet and lots of extra open space for fun. There is a 2-car garage with plenty of parking and a walk in mudroom with a washer and dryer and room to store all of your gear. The home is equipped with solar panels installed by Tesla to help keep down your energy costs and has 3 maintenance-free Tesla power walls to run the house as a generator. The outdoor space is fantastic with spacious decking in the yard for entertaining, an oversized heated pool, an outdoor shower and, of course, a U.S. Open-sized tennis court with appropriate colors! Hamptons vacation at its best!

Rental Reg. # 22-1,364. This world class retreat by renowned architect Bruce Nagel is an entertainers dream home. Located equidistant between Sag Harbor and East Hampton Village shops, restaurants, and world-class beaches, this striking residence expertly blends simple, sleek, modern aesthetics with classic, country-barn architectural style. The result is a magnificent compound of 3 cohesive contemporary barns that are seamlessly joined with flawless open interior spaces and stunning outdoor elements. This immaculate home epitomizes casual sophistication, equally comfortable for residents and their guests alike with four luxurious living areas for chic entertaining or for tranquil reflection. Sited on 2 very private acres, the expansive grounds with specimen gardens, fountains, and private patios equally impresses. The home features 6 bedrooms, 6 full and 1 half baths across 7,000+ sq ft of light-filled living space. Walls of glass surround the living/dining/kitchen+great room with fireplace and showcase outdoor dining and lounging patios that surround a heated, gunite, salt-water swimming pool. The primary suite is set in its own private structure with 25' ceilings, a fireplace with lounge area, en suite bath with soaking tub, and an exclusive outdoor courtyard with spa. Five comfortable en suite guest bedrooms are located in an additional structure which also includes a library/sitting room with high ceilings, a wood-burning fireplace, and views of the grounds. The professional chef's kitchen is fitted with double Wolf ovens, side-by-side Sub-Zero refrigeration units, two dishwashers, stone countertops, and a wet bar with a beverage center. The finished lower level features a large comfy den and office, a gym with Peleton, a sauna with private bath, a cedar wood & glass wine cellar and a double stacked laundry room. Additional amenities include a gated entrance providing privacy and security, fabulous landscape lighting for your evening enjoyment, a formal entrance with reflecting pools, a 3-car garage, outdoor shower and a house manager provided at the owners expense. 7 Rolling Wood is your ticket to an unforgettable summer in the Hamptons.

Greenport village 5 bedrooms, 2 baths with sweeping Water Views, adjacent to 6th St bay beach & park. Architect-designed & decorated interiors, chef's kitchen, 2nd floor sundeck and large yard with garden & outdoor dining area. Huge water-facing sun porch with wall of windows looking out on the bay. Short distance to farmers markets, wineries, shopping, LIRR & Jitney. RP# 22-298

Welcome to your luxurious retreat in Sagaponack, where tranquility meets sophistication. This newly built, eight-bedroom, seven-bath home is a testament to modern elegance, boasting high-end finishes and designer furnishings throughout. Situated on nearly 3 acres of lush vibrant landscaping, privacy abounds in this sanctuary, offering a serene escape from the hustle and bustle of everyday life. Step inside to discover a spacious interior adorned with exquisite details and thoughtful design. The open-concept living spaces seamlessly flow from one room to the next, creating an inviting atmosphere for gatherings and relaxation. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and ample counter space for culinary creations. Outside, a gunite and saltwater pool beckons for leisurely afternoons spent basking in the sun or cooling off with a refreshing swim. Surrounded by meticulously landscaped grounds and expansive decks, the outdoor oasis provides the perfect backdrop for alfresco dining, entertaining guests, or simply unwinding in nature's embrace. Located in the prestigious Sagaponack area, this residence offers proximity to the ocean and all the amenities the Hamptons have to offer. Whether you're seeking adventure or relaxation, this idyllic summer getaway promises an unforgettable experience for discerning travelers seeking the ultimate in luxury living. Now available for Summer 2024!