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    • Located on picturesque Old Harbor Road in the coveted seaside hamlet of New Suffolk, this irresistibly charming Dutch gambrel home was built by a master craftsman and lovingly referred to by the former owner as The Guest House. The residence features two ensuite bedrooms, three full baths, a sun-drenched dining room with a wood-burning fireplace, a large living room with an additional wood-burning fireplace, a cozy den with built-in shelving, and a beautiful screened-in porch. A single-story chef’s kitchen overlooks the yard, featuring a soaring vaulted ceiling and large French doors that open onto a generous bluestone patio. The property’s highlight is its magical grounds, which include a large in-ground gunite-heated saltwater pool, a handsome barn, and a professionally designed landscape with winding garden paths dotted with century-old trees, mature hollies, and vibrant hydrangeas. The result is a stunning green enclave that creates a private and enchanting setting. A sandy bay beach, Old Cove Yacht Club, and Shagwog Marina are just down the street. The property is two minutes from New Suffolk’s restaurants and business district and minutes to Cutchogue’s downtown. 34
      650 Old Harbor Rd Southold, NY 11956
      $1,795,000
      2 Bedrooms 3 Full Baths Sq. Ft. 2025.00:#
      Single Family For Sale ML# 3591133
      Located on picturesque Old Harbor Road in the coveted seaside hamlet of New Suffolk, this irresistibly charming Dutch gambrel home was built by a master craftsman and lovingly referred to by the former owner as The Guest House. The residence features two ensuite bedrooms, three full baths, a sun-drenched dining room with a wood-burning fireplace, a large living room with an additional wood-burning fireplace, a cozy den with built-in shelving, and a beautiful screened-in porch. A single-story chef’s kitchen overlooks the yard, featuring a soaring vaulted ceiling and large French doors that open onto a generous bluestone patio. The property’s highlight is its magical grounds, which include a large in-ground gunite-heated saltwater pool, a handsome barn, and a professionally designed landscape with winding garden paths dotted with century-old trees, mature hollies, and vibrant hydrangeas. The result is a stunning green enclave that creates a private and enchanting setting. A sandy bay beach, Old Cove Yacht Club, and Shagwog Marina are just down the street. The property is two minutes from New Suffolk’s restaurants and business district and minutes to Cutchogue’s downtown.
      Presented By: Compass Greater NY LLC  
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This beautiful home with in-ground pool and ample private open space exudes beach resort ease and is rarely available for rent. Located in a quiet enclave off the vineyards mile of Southold on the north fork, it is within proximity to farms, town, beaches and restaurants. The home which entered via a tree lined drive, is comprised of two stories, plus a lower level. The first floor features a southeast facing double height living room with woodburning fireplace, a modern kitchen with breakfast counter, a formal dining area which opens to a vast deck for lounging and socializing. A private primary suite is on the first floor with a dedicated full bathroom and closet. Off of the main entry is half bath and another closet. There is an attached one care garage. The second floor has two bedrooms with peek-a-boo waterviews, each with a private balcony.There is a guest bath on this level. The lower level has full glass sliding doors from the family room to outside. There is also a full bath, wine closet, laundry and plenty of storage space. The fenced in backyard has a pool with large patio that provides secure and private space for recreation, and opportunities for gardening. Potential boat dock available. 32
      Southold, NY 11971
      $98,000
      3 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2085.00:#
      Single Family For Sale ML# 3590555
      This beautiful home with in-ground pool and ample private open space exudes beach resort ease and is rarely available for rent. Located in a quiet enclave off the vineyards mile of Southold on the north fork, it is within proximity to farms, town, beaches and restaurants. The home which entered via a tree lined drive, is comprised of two stories, plus a lower level. The first floor features a southeast facing double height living room with woodburning fireplace, a modern kitchen with breakfast counter, a formal dining area which opens to a vast deck for lounging and socializing. A private primary suite is on the first floor with a dedicated full bathroom and closet. Off of the main entry is half bath and another closet. There is an attached one care garage. The second floor has two bedrooms with peek-a-boo waterviews, each with a private balcony.There is a guest bath on this level. The lower level has full glass sliding doors from the family room to outside. There is also a full bath, wine closet, laundry and plenty of storage space. The fenced in backyard has a pool with large patio that provides secure and private space for recreation, and opportunities for gardening. Potential boat dock available.
      Presented By: Compass Greater NY LLC  
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to North Fork Estates in Cutchogue! This new construction Modern Farmhouse-style home offers luxurious living with 4/5 bedrooms and 3 pristine bathrooms. Featuring exceptional craftsmanship and attention to detail throughout, this home boasts a spacious, open-concept eat-in gourmet kitchen, a cozy living area with gas fireplace, and a 2-car garage with a finished bonus room. The private backyard is an entertainer’s dream with a heated 20x40 saltwater pool, professional landscaping, a paver patio, and an outdoor shower. Situated just moments from downtown Cutchogue, local shops, restaurants, and renowned wineries, this home offers the perfect blend of comfort, style, and convenience. 33
      860 Griffing Street Southold, NY 11935
      $1,425,000
      5 Bedrooms 3 Full Baths
      Single Family For Sale ML# 3590333
      Welcome to North Fork Estates in Cutchogue! This new construction Modern Farmhouse-style home offers luxurious living with 4/5 bedrooms and 3 pristine bathrooms. Featuring exceptional craftsmanship and attention to detail throughout, this home boasts a spacious, open-concept eat-in gourmet kitchen, a cozy living area with gas fireplace, and a 2-car garage with a finished bonus room. The private backyard is an entertainer’s dream with a heated 20x40 saltwater pool, professional landscaping, a paver patio, and an outdoor shower. Situated just moments from downtown Cutchogue, local shops, restaurants, and renowned wineries, this home offers the perfect blend of comfort, style, and convenience.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • NEW CONSTRUCTION Spacious and Stylish, in a private Beach community. This thoughtfully designed plan, features 5 beds, 4.5 bath. Two en-suite primary bedrooms. 9ft ceilings thru out. Designer kitchen with island. Second floor has an additional bonus space. Large walkout basement with 9 ft ceilings.Heated pool and outdoor showing add to the North Fork experience.Close to winery’s, shopping and transportation. Additional Information: ParkingFeatures:1 Car Attached, 4
      1855 Greenway East Southold, NY 11957
      $1,895,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 2950.00:#
      Single Family For Sale ML# H6335251
      NEW CONSTRUCTION Spacious and Stylish, in a private Beach community. This thoughtfully designed plan, features 5 beds, 4.5 bath. Two en-suite primary bedrooms. 9ft ceilings thru out. Designer kitchen with island. Second floor has an additional bonus space. Large walkout basement with 9 ft ceilings.Heated pool and outdoor showing add to the North Fork experience.Close to winery’s, shopping and transportation. Additional Information: ParkingFeatures:1 Car Attached,
      Presented By: Corcoran Baer & McIntosh  845-358-9440
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • INDIAN NECK FARM: UNPARALLELED - UNRIVALED - UNSURPASSED Nestled along a deep-water creek on the North Fork of Long Island lies a once-in-a-lifetime, 148-acre waterfront estate. The perfect sanctuary for you and your guests to escape the frantic pace of everyday life. This extraordinary legacy assemblage is also refuge for an abundance of wildlife, including quail, pheasant, songbirds, owl, and red-tailed hawks. Spring and Summer offer some of the best fishing on the Island. Simply leave from your 60’ floating dock located on a sheltered cove along the east end of the property, which also has the designation from New York State, to harvest shellfish on a year-round basis. There is a 60-acre certified organic farm which includes a chef’s variety garden, an attached apothecary and greenhouse. The latest infrastructure includes solar technology, state-of-the-art cooling, vegetable washing and packing equipment. 20 acres of pasture for production and resident animals completes your farm to table experience. Lifestyle activities you and your guests can expect range from a short game golf course, full practice putting green, simulator barn, tennis, swimming, hunting, and fishing. A state-of-the-art fitness and wellness barn, include a Pilates reformer, indoor cycling with a video wall, free weights and strength training equipment, a hyperbaric chamber, cryo-unit, ColdTub, infrared sauna and more. Indian Neck Farm accommodations offer the ultimate in privacy and unsurpassed comfort. Unplug, relax and simply be, uninterrupted. Rustic simplicity and extraordinary luxury offer a unique and memorable experience. Nature is the backdrop and sets the tone for you and your guests. Blending comfort and style, with multiple ensuite guest rooms, common areas, and fireplace lounges. Enjoy exceptional meals from the main house gourmet kitchen or make pizzas in your pizza oven at the poolside covered bar and grill. Indian Neck Farm, make this your dream come true. This Could Be You! 23
      4170/3375+ Indian Neck Lane Southold, NY 11958
      $35,500,000
      11 Bedrooms 10 Full Baths 6 Half Baths
      Single Family For Sale ML# 3590171
      INDIAN NECK FARM: UNPARALLELED - UNRIVALED - UNSURPASSED Nestled along a deep-water creek on the North Fork of Long Island lies a once-in-a-lifetime, 148-acre waterfront estate. The perfect sanctuary for you and your guests to escape the frantic pace of everyday life. This extraordinary legacy assemblage is also refuge for an abundance of wildlife, including quail, pheasant, songbirds, owl, and red-tailed hawks. Spring and Summer offer some of the best fishing on the Island. Simply leave from your 60’ floating dock located on a sheltered cove along the east end of the property, which also has the designation from New York State, to harvest shellfish on a year-round basis. There is a 60-acre certified organic farm which includes a chef’s variety garden, an attached apothecary and greenhouse. The latest infrastructure includes solar technology, state-of-the-art cooling, vegetable washing and packing equipment. 20 acres of pasture for production and resident animals completes your farm to table experience. Lifestyle activities you and your guests can expect range from a short game golf course, full practice putting green, simulator barn, tennis, swimming, hunting, and fishing. A state-of-the-art fitness and wellness barn, include a Pilates reformer, indoor cycling with a video wall, free weights and strength training equipment, a hyperbaric chamber, cryo-unit, ColdTub, infrared sauna and more. Indian Neck Farm accommodations offer the ultimate in privacy and unsurpassed comfort. Unplug, relax and simply be, uninterrupted. Rustic simplicity and extraordinary luxury offer a unique and memorable experience. Nature is the backdrop and sets the tone for you and your guests. Blending comfort and style, with multiple ensuite guest rooms, common areas, and fireplace lounges. Enjoy exceptional meals from the main house gourmet kitchen or make pizzas in your pizza oven at the poolside covered bar and grill. Indian Neck Farm, make this your dream come true. This Could Be You!
      Presented By: Corcoran  631-765-1300
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Stunning Resort-Style Home with Modern Smart Features on the North Fork Discover a new level of luxury and sophistication in this North Fork masterpiece, the latest in a series of meticulously designed homes with exceptional amenities. This residence captures the essence of resort living, surrounded by tranquil Islands End public golf course, the popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse. This neighborhood beach/park offers paddleboard and kayak stations along the marina, this home is perfect for embracing the North Fork’s outdoor lifestyle. As a state-of-the-art smart home, the apps provide remote access for lighting, heating, and air conditioning, music indoors and outdoors, and televisions strategically placed on the second floor, in the main living areas, and in a private TV room in the basement. The expansive floor plan offers not one, but two luxurious owner’s suites, one on the main level and another on the second floor, complemented by two additional bedrooms with private bathrooms. With a sleek, modern aesthetic, the home is thoughtfully designed for indoor-outdoor living. Outside, an elegant pool with a waterfall and evening lighting package becomes the centerpiece of the outdoor experience, complete with an option for an outdoor kitchen. Stunning dining area, and a lounge with a fireplace-perfect for entertaining or relaxing in style. This property brings the quality of its design and build to the forefront across all three levels, offering a flawless blend of comfort, functionality, and contemporary elegance. Indulge in this rare opportunity to own a slice of resort-like paradise on the North Fork. 37
      250 Osprey Nest Rd Southold, NY 11944
      $3,799,999
      4 Bedrooms 5 Full Baths 2 Half Baths Sq. Ft. 5220.00:#
      Single Family For Sale NEW ML# 3590145
      Stunning Resort-Style Home with Modern Smart Features on the North Fork Discover a new level of luxury and sophistication in this North Fork masterpiece, the latest in a series of meticulously designed homes with exceptional amenities. This residence captures the essence of resort living, surrounded by tranquil Islands End public golf course, the popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse. This neighborhood beach/park offers paddleboard and kayak stations along the marina, this home is perfect for embracing the North Fork’s outdoor lifestyle. As a state-of-the-art smart home, the apps provide remote access for lighting, heating, and air conditioning, music indoors and outdoors, and televisions strategically placed on the second floor, in the main living areas, and in a private TV room in the basement. The expansive floor plan offers not one, but two luxurious owner’s suites, one on the main level and another on the second floor, complemented by two additional bedrooms with private bathrooms. With a sleek, modern aesthetic, the home is thoughtfully designed for indoor-outdoor living. Outside, an elegant pool with a waterfall and evening lighting package becomes the centerpiece of the outdoor experience, complete with an option for an outdoor kitchen. Stunning dining area, and a lounge with a fireplace-perfect for entertaining or relaxing in style. This property brings the quality of its design and build to the forefront across all three levels, offering a flawless blend of comfort, functionality, and contemporary elegance. Indulge in this rare opportunity to own a slice of resort-like paradise on the North Fork.
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Contemporary Home with Heated Pool, Less then a 1/2 Mile from a Gorgeous Long Island Sound Beach. Come Enjoy the Great North Fork. The Perfect Getaway Does Exist! With 3 Bedrooms and 2 Full Baths, Close Proximity to the Beach, a Pool Integrated into the Deck, and a Separate Rooftop Deck, This Property Offers an Ideal Mix of Relaxation and Style. The Spacious Gourmet Kitchen (Sub-Zero Fridge, Meile Oven, Wolf Gas Range) and Multiple Living Areas Make it Great for Both Quiet Retreats and Entertaining Guests. The North Fork is Known for its Beautiful Landscapes, Beaches, Wineries, and Local Charm, So This Home is in a Prime Spot to Enjoy All it Has to Offer! Off Season $4, 000 Per Month; Year Round $4, 200 Per Month, Memorial Day to Labor Day $32, 000; June $8, 000; July $12, 000, August to Labor Day $15, 000; $3, 000 Weekly with 2 Week Minimum. Permit #1217. 31
      8200 Soundview Avenue Southold, NY 11971
      $4,000
      3 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3590047
      Contemporary Home with Heated Pool, Less then a 1/2 Mile from a Gorgeous Long Island Sound Beach. Come Enjoy the Great North Fork. The Perfect Getaway Does Exist! With 3 Bedrooms and 2 Full Baths, Close Proximity to the Beach, a Pool Integrated into the Deck, and a Separate Rooftop Deck, This Property Offers an Ideal Mix of Relaxation and Style. The Spacious Gourmet Kitchen (Sub-Zero Fridge, Meile Oven, Wolf Gas Range) and Multiple Living Areas Make it Great for Both Quiet Retreats and Entertaining Guests. The North Fork is Known for its Beautiful Landscapes, Beaches, Wineries, and Local Charm, So This Home is in a Prime Spot to Enjoy All it Has to Offer! Off Season $4, 000 Per Month; Year Round $4, 200 Per Month, Memorial Day to Labor Day $32, 000; June $8, 000; July $12, 000, August to Labor Day $15, 000; $3, 000 Weekly with 2 Week Minimum. Permit #1217.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This meticulously restored Gilded Age shingle-style home presents a rare opportunity to own one of the few remaining large, turn-of-the-century North Fork summer estates. Spanning over 10, 000 sq. ft. on 140 feet of pristine bayfront with a private sandy beach, the main residence seamlessly blends period architecture with modern luxury. Every detail, down to the doorknobs and hardware, has been meticulously curated, resulting in a warm and classic home anchored in refinement and exceptional craftsmanship. Perfect for both grand entertaining and intimate gatherings, expansive living spaces feature soaring ceilings, multiple fireplaces, and thoughtful design moments throughout. Highlights on the first floor include a large waterside living room and dining room with charming fireplace alcoves, a sprawling chef’s kitchen with breakfast room and handsome butler’s pantry, a dedicated flower-cutting room with custom marble sink, and an enormous screened-in outdoor sitting porch complete with an outdoor dining room and kitchen. The second floor houses the large primary suite with an ensuite bath, extensive walk-in closets, a dressing room, and a cozy sitting room with an oversized fireplace. The balance of the second and third floors includes five additional waterside bedrooms, a library, an office, multiple wet bars, a laundry room, and 5 baths with steam showers and soaking tubs. Outside, lush perennial gardens and hedged lawns surround the property. A beautiful, private gunite pool sits on the waterside, offering a serene oasis with sweeping water views. A charming carriage house adds further versatility, featuring a great room, home theater, and gym. The estate also includes a historic icehouse, preserving its rich legacy. Whether sitting by the bay, hosting holidays, or enjoying movie nights in the theater, this extraordinary property promises a lifestyle of elegance and tranquility. 37
      12120 New Suffolk Avenue Southold, NY 11935
      $12,000,000
      6 Bedrooms 5 Full Baths 3 Half Baths Sq. Ft. 9000.00:#
      Single Family For Sale ML# 3587632
      This meticulously restored Gilded Age shingle-style home presents a rare opportunity to own one of the few remaining large, turn-of-the-century North Fork summer estates. Spanning over 10, 000 sq. ft. on 140 feet of pristine bayfront with a private sandy beach, the main residence seamlessly blends period architecture with modern luxury. Every detail, down to the doorknobs and hardware, has been meticulously curated, resulting in a warm and classic home anchored in refinement and exceptional craftsmanship. Perfect for both grand entertaining and intimate gatherings, expansive living spaces feature soaring ceilings, multiple fireplaces, and thoughtful design moments throughout. Highlights on the first floor include a large waterside living room and dining room with charming fireplace alcoves, a sprawling chef’s kitchen with breakfast room and handsome butler’s pantry, a dedicated flower-cutting room with custom marble sink, and an enormous screened-in outdoor sitting porch complete with an outdoor dining room and kitchen. The second floor houses the large primary suite with an ensuite bath, extensive walk-in closets, a dressing room, and a cozy sitting room with an oversized fireplace. The balance of the second and third floors includes five additional waterside bedrooms, a library, an office, multiple wet bars, a laundry room, and 5 baths with steam showers and soaking tubs. Outside, lush perennial gardens and hedged lawns surround the property. A beautiful, private gunite pool sits on the waterside, offering a serene oasis with sweeping water views. A charming carriage house adds further versatility, featuring a great room, home theater, and gym. The estate also includes a historic icehouse, preserving its rich legacy. Whether sitting by the bay, hosting holidays, or enjoying movie nights in the theater, this extraordinary property promises a lifestyle of elegance and tranquility.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to this charming cape, a true gem with its private beach and inviting swimming pool. This sweet home features 4 bedrooms and 2 full baths, combining easy living and casual comfort . Spacious, sunlit rooms provide ample living space for relaxation and entertaining. Cozy up by the fireplace in the living room, or retreat to the den for a quiet evening with a book or movie. The open-concept kitchen seamlessly connects to the living room. Large bedrooms, convenient first-floor laundry and home office complete the interior. The breathtaking backyard steals the show, with a stunning inground pool perfect for hot summer days, lush landscaping ensures privacy, making the firepit area a perfect spot for unwinding and enjoying outdoor serenity. The private community beach offers peaceful moments by the water. This location is ideal for sunset strolls or weekend fun. 22
      130 Tasker Lane Southold, NY 11944
      $1,475,000
      4 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3587176
      Welcome to this charming cape, a true gem with its private beach and inviting swimming pool. This sweet home features 4 bedrooms and 2 full baths, combining easy living and casual comfort . Spacious, sunlit rooms provide ample living space for relaxation and entertaining. Cozy up by the fireplace in the living room, or retreat to the den for a quiet evening with a book or movie. The open-concept kitchen seamlessly connects to the living room. Large bedrooms, convenient first-floor laundry and home office complete the interior. The breathtaking backyard steals the show, with a stunning inground pool perfect for hot summer days, lush landscaping ensures privacy, making the firepit area a perfect spot for unwinding and enjoying outdoor serenity. The private community beach offers peaceful moments by the water. This location is ideal for sunset strolls or weekend fun.
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Stunning Orient retreat with a private heated gunite pool; enjoy an ideal location with a beach and village just down the block. This tranquil home features soaring ceilings, two fireplaces, four ensuite guest rooms, a private office, an enormous eat-in kitchen, a light-filled dining room, a hotel-like master suite with a second-floor balcony, charming front porch, two living rooms, and beautiful design details at every turn. This home is as stylish as it is comfortable and is the perfect summer rental to host family and friends. Mature trees and landscaping dots the exterior with a large outdoor shower. Garage with flex rec room space. Plenty of parking. Just minutes to Greenport Village and all the best amenities Orient and the North Fork has to offer. 36
      400 Youngs Rd Southold, NY 11957
      $50,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3300.00:#
      Single Family For Sale ML# 3585970
      Stunning Orient retreat with a private heated gunite pool; enjoy an ideal location with a beach and village just down the block. This tranquil home features soaring ceilings, two fireplaces, four ensuite guest rooms, a private office, an enormous eat-in kitchen, a light-filled dining room, a hotel-like master suite with a second-floor balcony, charming front porch, two living rooms, and beautiful design details at every turn. This home is as stylish as it is comfortable and is the perfect summer rental to host family and friends. Mature trees and landscaping dots the exterior with a large outdoor shower. Garage with flex rec room space. Plenty of parking. Just minutes to Greenport Village and all the best amenities Orient and the North Fork has to offer.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
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    OneKey™ MLS The data relating to real estate for sale on this web site comes in part from the OneKey™ MLS. Real Estate listings held by brokerage firms other than Beninati are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.
    Office: (631) 765 5333 Fax (631) 765 5225 broker@beninatiassociates.com

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    Office: 52875 Main Road, Southold NY 11971
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