Cutchogue NY Real Estate & Homes for Rent

Don't miss your chance to experience unparalleled luxury in this magnificent estate, nestled on five picturesque acres amidst some of the region's most prestigious vineyards. This extraordinary home offers a perfect blend of elegance and tranquility, ideal for those seeking a refined living experience. Spanning an impressive 7,000 square feet, the residence is designed with meticulous attention to detail. Floor-to-ceiling windows flood the space with natural light and offer breathtaking views of the surrounding vineyards. The home features seven generously sized bedrooms and seven opulent bathrooms, ensuring ample space and privacy for everyone. One of the standout features is the expansive roof deck, providing panoramic views that stretch across the vineyards to the Long Island Sound. This serene setting is perfect for both entertaining guests and enjoying quiet moments of relaxation. With its unparalleled location and exquisite amenities, this estate offers a living experience unlike anything else on the market.

2024 Rates: October $10,000/2025 Rates MDW-LD $80K, June $15K, July $27K, A1-LD $30K, Sept $17K, October $15K. 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.

Enjoy the quiet country life when you move into this tastefully-furnished honest and adorable history home nearly hidden by mature shrubs and trees on a quiet country lane. Delight in awe-inspiring sunsets and skyscapes and savor fresh produce harvested from your own garden plot. Then wash your cares away in the rustic outdoor shower! Set on two pastoral Cutchogue acres and surrounded by lands of Macari Vineyards and world-renowned greens purveyor Satur Farms, you will be immersed in the North Fork's nearly four hundred year agricultural tradition. Is this the perfect spot for a yearround second home? Nothing compares! Come visit soon!

Newly Renovated Ranch Oasis in the Heart of the North Fork! Embrace the laid-back luxury of living in this stunning 3-bedroom, 2.5-bathroom ranch, completely renovated and move-in ready! This beautiful home is ideally situated in the central part of the North Fork, putting you within easy reach of everything this vibrant region has to offer. Stroll to charming shops, hop on public transportation to explore further, or indulge in fresh produce at farm stands - all just moments away. Craving a taste of the good life? World-renowned vineyards, delectable restaurants, and the picturesque Nassau Point Beach are all at your fingertips. This prime location also grants you access to all Southold town beaches, ensuring endless summer fun. Don't miss this opportunity to live in the heart of the North Fork's magic!

Charming 3-Bed, 2-Bath Home in Cutchogue's Creekfront Community Welcome to this newly renovated gem nestled in a serene Creekfront community in Cutchogue. This home boasts 3 spacious bedrooms and 2 modern baths, set on a sprawling property perfect for nature enthusiasts. The relaxed, sophisticated decor complements the spacious rooms, offering a perfect retreat from the hustle and bustle. A standout feature of this property is the large barn in the yard, ideal for storing bikes and summer recreational toys. The backyard patio provides a lovely setting for outdoor barbecues, while the spacious lawn offers plenty of room for playing and enjoying the outdoors. Inside, you'll find a brand new navy blue kitchen with stainless steel appliances, beautifully coupled with old-world built-in corner cabinets-a welcome mix of modern convenience and timeless charm. Enjoy stunning water views and the convenience of launching your boat, kayak, or paddle boards just at the end of the road. Cutchogue is home to many fine vineyards, perfect for sipping the fruits of the land, and farm-to-table dining experiences. Pristine beaches await for sunbathing and swimming, while quiet country roads are ideal for cycling and connecting with nature. The North Fork boasts plenty of restaurants offering fresh seafood in casual waterside settings. This is an ideal setting to relax and savor the beauty of nature. August: $11,000 September: $9,000

Take A Step Back In Time And Enjoy The Peaceful North Fork In This 3 Bedroom 1 Bath Cottage In A Quaint Beach Community. Perfect For Your Seasonal Getaway. Close To All The North Fork Has To Offer. Stroll To The Beaches Where You Can Kayak Around The Bay, Take A Bike Ride To A Local Vineyard And Sip A Fine Glass Of Wine, Taks A Short Drive To One Of The Farms, Fine Dining.

1830'S Horse Barn Sitting Elegantly In The Village Of Cutchogue. Cathedral Ceilings, Hardwood Floors Throughout, Stainless Steel Appliances, 10' Maple Wood Block Center Isle, Soapstone Countertops, Soaking Tub, Mudroom, Views Of The Apple Orchard, And The Closeness Of Nearby Beaches And Village.

Come and enjoy the privacy that lies behind the doors of this reimagined modern ranch. Once inside you will be thrilled by the level of detail in this 2023 gut renovation. As you enter the home, you are welcomed with expansive views across the large backyard onto the surrounding vineyards. The 14' lofty ceiling highlights the kitchen and dining space creating a bright and airy feel for you to enjoy your morning coffee or breakfast at the 10-person dining table while taking in the surrounding natural beauty. High-end appliances featuring Wolf stove, Subzero fridge and Bosch dishwasher are all in your bright open kitchen. The stylish living space also features a lovely fireplace; the perfect place to curl up with a book. Come out your back door and enjoy the lush gardens with 180 degree views of the vineyards from the stone patio, or venture off to your private fenced in pool area with a 20 x 40 heated vinyl pool and separate patio area. Or perhaps you'd prefer to sit by the fire pit and make s'mores, or have cocktail and watch the sunset. At one end of the home, you have the primary suite facing out to the views, with its own dressing area and private bath with Dornbracht fixtures and radiant heat flooring. Nearby, you have a bedroom with a full bed and a twin day bed with a full bath is just outside the room. From this side of the house, you have access to a 25'x 14' screened in porch. At the other end of the house is a large king guestroom with ensuite bath and space for a small home office area within the bedroom. Next to the bedroom, you will find the den off the kitchen that can also function as a home office or a fourth bedroom with Full pullout couch and closet space. Downstairs you'll find the finished, sun-filled entertainment space with 85" TV and an attached game room with table tennis. This space essentially functions as another full living room, complete with microwave and fridge for movie night. Rainy days are never an issue with this set up. Full marble bath on this level, along with an extra-large laundry area with brand new washer/dryer units and hanging and folding area. The home is equipped with hardwood floors and central air throughout. This 4-bedroom 4-bath home sits on just shy of an acre of land and is conveniently located in the heart of the North Fork, with a quick drive to Love Lane shopping and gourmet market, Strongs Marina for a boat ride, or Magic Fountain for artisanal ice cream flavors. Looking for a beach day? Take your pick of the Sound or Bay beaches; or if you're a land lover, choose one of the many nearby wineries to sit outside and enjoy a glass of wine. You can always get some fresh air fun at the various nearby golf courses, or treat yourself to the easily accessible shops and restaurants of Southold and Greenport. No shortage of options with this property! Rental permit# 1116

This spectacular home on Peconic Bay (Broadwater Cove) features phenomenal views of Nassau Point and Robins Island. The spectacular design includes wall-to-wall windows, an open floor plan, and two large entertaining waterfront decks. There are 4 bedrooms, including the master suite with unobstructed water views. The great room, kitchen, and dining area all open out to the dining deck, beach, and waterfront. The guest cottage has heat and central air, floor to ceiling windows, a large additional master suite with full bath, large living area, and an additional half bath. The oversized, 2-car garage has ample room for storage. The 2 private docks and completely private beach make this property a summer haven. Close to Cutchogue and all the north fork has to offer.

This charming 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, convenience, and seaside serenity. As you step inside, you'll notice the beachy feel that permeates every corner of this home. The spacious living areas invite you to relax and unwind, with ample room and a well-appointed Chef's Kitchen for gatherings and entertaining. Each bedroom is designed to offer tranquility and functionality, featuring windows that flood the rooms with natural light and offer glimpses of the surrounding natural beauty. Venture into the backyard, and you'll discover your own private paradise. A gunite saltwater pool offers a refreshing escape during hot summer days, accompanied by an outdoor shower. The Dave Allison Park is just a short stroll away. Its playground and sandy community beach are ideal destinations for picnics, games, and waterfront fun. East Creek Beach, a private haven, is also within walking distance, offering secluded shores and tranquil waters for swimming and sunbathing. With its unbeatable location and irresistible amenities, this home is the ultimate retreat for those seeking the perfect blend of comfort and coastal living on the North Fork. Within minutes to world-renowned vineyards and local farms! Don't miss your chance to make memories in this seaside sanctuary on the North Fork - Now available in Summer 2024 and off-season.

This is your Zen oasis! Unwind and connect with nature in this lush Zen water view cottage. The perfect getaway from hectic daily life. Lounge poolside or stargaze on the deck overlooking Little Creek. 4 bedrooms, 3.5 baths, including a jacuzzi in the primary bedroom, fabulous outdoor shower, incredible pool house, chef's kitchen, outdoor BBQ and dining area and a close drive or stroll to the Causeway Beach! Close to North Fork boating, marinas, farmstands, award winning vineyards, renowned restaurants, and great shopping. Permit # 1089

Permit# 0019. . Privacy And Views Abounds with This Beautiful Reproduction Of 19th Century Waterfront Barn. Wonderful Open Great Room with Streaming Light from Large Doors and Transom Windows. Mbr Lower Level, Bath, Grand Staircase to Sleeping Loft and Sitting Area.

North Fork summer living at its best on coveted Nassau Point. Sprawling lawns and manicured gardens define this 3-acre property featuring a stylish, spacious home with a large ensuite master, two ensuite guest bedrooms, and a charming guest cottage with an additional bedroom and full bathroom. A large eat-in kitchen flows to a dining room accommodating ten people or more. The bright living room features a wood-burning fireplace and looks out over a large park-like front lawn. The 50-foot gunite pool is the highlight of the outdoor living, with a nearby screen porch, deck, and patios offering lounging, reading, yoga, and dining options. A library/office allows for a work-for-home space or overflow for guests. Choose from two nearby beaches less than 5 minutes away. Even closer is a path to access Peconic Bay. Washer & dryer on site. June: $25,000; July: $27,500; August: $32,500; September: $25,000

Your Summer Waterfront Retreat Is Now Available And Waiting For You! Gourmet Chef's Kitchen With Stainless Steel Appliances. Gas Stove. Open Plan Living, Filled With Natural Light. Built In Closets In All 3 Bedrooms. Studio/Extra Bedroom On Ground-floor. Wood Burning Stove. Recent Upgrades Include The Following: New Anderson Windows Throughout In 2021. New Pool Liner And Travertine Pavers Installed Around The Perimeter Of The Pool In 2022. Ground-floor Bathroom Was Renovated In 2022. Hardwood Floors Throughout. Outdoor In-Ground Pool. Owners Canoe & BBQ Are Available For Use Upon Request. Break Away From All The Stress And Join Us Here On The North Fork For Some Well Deserved Rest & Recreation. We Have Some Of The Most Beautiful Beaches In The World, Michelin Star Restaurants, High Street Stores, Surrounded By Award Winning Vineyards/Tasting Rooms, Fishing, Swimming, You Name It... It's All Here Waiting For You. Now Book Your Waterfront Summer Retreat Today! June: $10,000 | July: $15,000 | Aug - LD: $20,000 | July/August: $32,000 | Sept: $8000 | Oct: $4000. Rental Permit #: 0081

#NeverMissASunset. Enjoy Breath Taking Sunsets high on the Bluff overlooking the Long Island Sound With Your Own Private Sandy Beach and Community Stairs. Spacious Bedrooms with California closet (entire room) off Primary Bedroom, 2 Sun Rooms, Incredible Water Views From Nearly All The Rooms. Updated Baths And Kitchen With Granite Counter Tops, Spectacular Landscaping, Outdoor Shower. The Perfect Summer Getaway Or Year Round Home! Great For Entertaining & an ideal setting for summer stargazing. Permit#1029

Sprawling Nassau Point estate with open floor plan, 4 ensuite bedrooms and beautiful pool area. Enjoy summer days by the pool or beach directly across the street. 1st floor features an open floor plan with living, dining and large chef's kitchen. Also on the 1st floor, a large great room for gathering or watching movies. The hotel-like primary bedroom features peek-a-boo water views and a large primary ensuite bath. Plenty of room to stretch out and relax while retreating to the North Fork summer! Private mooring is available for guests' use.

Be surrounded by the peaceful beauty of nature while spending your summer in this stylish mid-century modern style home. You will enjoy lazy days in the pool or paddling on the creek, al fresco dining at night under the stars and many hours relaxing in this beautiful waterfront retreat. Mem. Day - Labor Day $75,000. June $20,000. July $30,000. Rented for Aug Permit #0087

Perfect summer getaway! 3 bedrooms, 2.5 bathrooms, in-ground pool, close to beach, business district, vineyards and restaurants. Two week minimum stay.

Perfect summer cottage. Location can't be beat! A stone's throw to serene Pequash beach. Nestled in quiet Fleet's Neck with 2 bay beaches within walking distance. Well maintained home. Available for summer or short term off-season rental.

Cutchogue North Fork: Spend August-LD 2025 in this beautifully appointed & very private Long Island Sound front home at 2430 Dignans Road, Cutchogue: come find out why the owners call it North Cliff. Spectacular decks & pool set high on the cliffs overlooking the LI Sound - private easy steps to beach. On the other side forever views of Oregon Road farmland. Published in international Fashion Magazines. Chique but casual Summer home. Inside Outside living. Endless beaches to take in and at night follow the lights from Horton's Lighthouse over the crescent coastline. Primary Suite with gorgeous long water views from large private sundeck. RP# 0579

Spectacular updated Cape with a heated pool at 25 Moose Trail, Cutchogue. Enjoy the chefs' kitchen & many spacious living and entertaining areas, including dining room, game room with pool table & arcade games, bedroom, & a full bath on the first floor, all tastefully furnished. Outside you have an expansive deck off the kitchen that takes you to the heated pool surrounded by a paver patio & professionally landscaped yard. This home also has beach rights to a beautiful sandy bay beach and park. Many wonderful vineyards, restaurants, and farm stands are close by. This is the perfect home for entertaining & family gatherings! RP# 0422 , AVAILABLE 2025 Memorial Day thru LD $59,000, June $12,000, July $22,000, August $25,000.

Cozy ranch home with a backyard overlooking a farm available to rent year-round. Heated pool completely updated furniture, paver patio, fire pit, and BBQ. Amazing location with water access for small boats, kayaks, and paddle boards down the road. A beautiful sandy beach less than one mile from the home. Multiple beaches to enjoy! Many extraordinary vineyards less than a mile from the home. Available to move in on August 1st. Southold Town Rental Permit #0934

New to Market FLEET's NECK Rental! Walk to Beach from your Private FABULOUS SUMMER OASIS. 4 Bedroom and 2 Full Bath Contemporary Home on tucked away Lot Set Well-Back from Road on 1 + acres. Offers Sleek Main Floor Living Area with Fireplace, Chandeliered Dining Area, Foyer, Light Bright Kitchen with All Stainless-Steel Appliances, that leads to a Furnished 2-Level Deck with Both Living and Dining/BBQ Spaces, 2 Spacious Bedrooms and a Full Bath with Walk-In Shower. Lower level has 2 Additional Bedrooms and a Large Full Bath with Separate Living/Entertaining/Gaming Area for more Informal Fun! Air Hockey, FOOSBALL,& Large Flat Screen TV! Two-Car Garage and Plenty of Guest Parking. Bedrooms provide own TVs and plenty of closet space. PLUS: Fenced-in Sprawling Summertime Fun & Relaxation Spot. 20x40 Heated, Lighted, Saltwater Pool, with 4 In-Pool Chaise Loungers, and steps to separate Jacuzzi Spa to warm up before you Cool Down. Also enclosed is an Outdoor BBQ Pavillion with Bar Area and Kitchenette, as well as Outdoor Living Room complete with Wide Screen TV, and outdoor lighting. Live Your Best Life Here or walk a short distance to Bay Beach at End of Street, or a Short Drive to Long Island Sound and Ocean Beaches, and Local Marinas. Nearby to Gourmet Restaurants, Wineries, Breweries, Golf, Shopping, and NF Farm Stands & Easy Access to the LIRR or NYC Jitney. 3rd Story Master Suite and Attic Off-Limits to Tenants. Utilities Not included in Rental Amounts. Landlord takes care of Pool and Lawn; Tenants to Reimburse for Utilities for the Term; One Month Security Deposit and Utility Deposit (50% of Estimated Term) Lease and Proof of Renters Insurance Required and Satisfactory Credit Approval.

This is your perfect getaway! Amazing location with water access steps away. 2 bedrooms, 2 bathrooms and an open floor plan with a wonderful yard for quiet evenings sitting outside on the patio! A short drive to the Causeway Beach and supermarkets, Braun's Fish Market, restaurants, and great shopping (you must go to North Fork Apothecary!) all within 5 minutes. Permit # 0754

Pristine and newly renovated craftsman home in Nassau Farms. Easy access to Nassau Point Beach. Bright and sunny great room with open floor plan; kitchen featuring granite counter tops, custom cabinetry, and high end appliances. Private backyard with bluestone patio, built-in outdoor sound system, stone fireplace, and outdoor cooking. Ideal vacation home on the North Fork. Private path to nearby kayaking. Convenient to all North Fork activities. Rented through May 31, 2025- Permit # 0283