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Southold Waterfront Properties

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    Showing 11 - 20 of 21 results| view:  results per page« 1|2|3 »
    • Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner offers a furnished year-round rental - $4200 per mo. Rental Permit# 1216., Additional information: ExterioFeatures:Tennis, year rent:4200 26
      150 Hobart Rd Southold, NY 11971
      $30,000
      2 Bedrooms 2 Full Baths Sq. Ft. 1300.00:# Square Feet
      Single Family For Rent ML# 3588931
      Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner offers a furnished year-round rental - $4200 per mo. Rental Permit# 1216., Additional information: ExterioFeatures:Tennis, year rent:4200
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car garage. The 2nd floor has 2 beds, bath, and addit’l laundry with a sprawling bonus room ideal for entertaining or relaxing. CAC ensures comfort on even the hottest days, with a full basement providing plenty of storage for your beach gear. Outside is your private paradise, with a refreshing 16 x 32 in-ground pool and dock. Close proximity to bay beaches, vineyards, farmstands, shopping and restaurants. Don’t miss this opportunity to experience luxury summer living! June 2025 $30, 000. July $35, 000. Aug-LD $45, 000. Off-season dates available. Southold Town Rental Permit #1085. 32
      910 Glenn Rd Southold, NY 11971
      $30,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent ML# 3546491
      Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car garage. The 2nd floor has 2 beds, bath, and addit’l laundry with a sprawling bonus room ideal for entertaining or relaxing. CAC ensures comfort on even the hottest days, with a full basement providing plenty of storage for your beach gear. Outside is your private paradise, with a refreshing 16 x 32 in-ground pool and dock. Close proximity to bay beaches, vineyards, farmstands, shopping and restaurants. Don’t miss this opportunity to experience luxury summer living! June 2025 $30, 000. July $35, 000. Aug-LD $45, 000. Off-season dates available. Southold Town Rental Permit #1085.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • ’ ONLY September onwards is available --- If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025., Additional information: Interior Features:Combo Kitchen, Efficiency Kitchen, Lease Term:August-Labor Day, Flexible, July, July-August, June, Memorial-Labor, Monthly, Interior Features:Separate Thermostat 29
      1205 Lake Drive Southold, NY 11971
      $25,000
      4 Bedrooms 4 Full Baths
      Single Family For Rent ML# 3528933
      ’ ONLY September onwards is available --- If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025., Additional information: Interior Features:Combo Kitchen, Efficiency Kitchen, Lease Term:August-Labor Day, Flexible, July, July-August, June, Memorial-Labor, Monthly, Interior Features:Separate Thermostat
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play., Additional information: Appearance:excellent 30
      3675 Wells Avenue Southold, NY 11971
      $20,500
      4 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3467464
      Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play., Additional information: Appearance:excellent
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Available seasonally, 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. Memorial Day-Labor Day $45, 000; June $8000; July $18, 000; August-LD $20, 000. 22
      355 Midway Rd Southold, NY 11971
      $20,000
      3 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3389441
      Available seasonally, 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. Memorial Day-Labor Day $45, 000; June $8000; July $18, 000; August-LD $20, 000.
      Presented By: Brown Harris Stevens N Fork  631-477-0551
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Now Available for Off Season Rental Until March 31, 2025 and Post Labor Day 2025. Rented June 1 - September 30th. Set Creekfront with Private Dock and Associated Bay Beach Access in Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2 Large Living Rooms, Well Appointed Kitchen with All High-End Appliances. 6 Burner Wolf Stove for Cooking. All Overlooking Dining, Living and Bar Area. All Utilities (Except Electric), Cleaning, Pool, Jacuzzi and Exterior Maintenance Provided by Landlord. Ample Parking. The Home Also Includes a Bocce Court, Ping-Pong and Shuffleboard Tables. All Prospective Tenants to Provide a Completed Application Via RentSpree. Link to be Provided. Rental Permit # 1180, Additional information: Appearance: Beautiful, Interiorr Features: Efficiency Kitchen, Guest Quarters, Interior Features: Separate Thermostat 36
      425 Cedar Point Drive E Southold, NY 11971
      $15,000
      5 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3700.00:#
      Single Family For Rent ML# 3573270
      Now Available for Off Season Rental Until March 31, 2025 and Post Labor Day 2025. Rented June 1 - September 30th. Set Creekfront with Private Dock and Associated Bay Beach Access in Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2 Large Living Rooms, Well Appointed Kitchen with All High-End Appliances. 6 Burner Wolf Stove for Cooking. All Overlooking Dining, Living and Bar Area. All Utilities (Except Electric), Cleaning, Pool, Jacuzzi and Exterior Maintenance Provided by Landlord. Ample Parking. The Home Also Includes a Bocce Court, Ping-Pong and Shuffleboard Tables. All Prospective Tenants to Provide a Completed Application Via RentSpree. Link to be Provided. Rental Permit # 1180, Additional information: Appearance: Beautiful, Interiorr Features: Efficiency Kitchen, Guest Quarters, Interior Features: Separate Thermostat
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented with dramatic vaulted ceilings, fireplace and wet bar. A wall of oversized sliding glass doors allow for plenty of natural light and lead to a 2, 000 sq. ft mahogany deck and heated gunite pool - ideal for comfort and relaxation. Two generously sized bedrooms and 1.5 baths complete the first floor. The second floor boasts an expansive primary suite with two walk-in closets and a luxurious bath including radiant heated floors, soaking tub, water closet, rain shower & body jets. Enjoy an early morning cup of coffee or star gaze in the evenings from your private water view balcony, making this room the perfect retreat. You will also find two additional bedrooms and two full baths on this floor. Enjoy all the North Fork has to offer and more with the deeded right of way that comes with this home which provides convenient access to sought-after McCabe’s Beach! Kenney’s Beach is also just a stone’s throw away! Don’t miss the opportunity to create a vacation to remember with this special home! Two-week terms are also available. Appearance: Mint 15
      11925 Soundview Avenue Southold, NY 11971
      $12,500
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3600.00:#
      Single Family For Rent ML# 3571029
      Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented with dramatic vaulted ceilings, fireplace and wet bar. A wall of oversized sliding glass doors allow for plenty of natural light and lead to a 2, 000 sq. ft mahogany deck and heated gunite pool - ideal for comfort and relaxation. Two generously sized bedrooms and 1.5 baths complete the first floor. The second floor boasts an expansive primary suite with two walk-in closets and a luxurious bath including radiant heated floors, soaking tub, water closet, rain shower & body jets. Enjoy an early morning cup of coffee or star gaze in the evenings from your private water view balcony, making this room the perfect retreat. You will also find two additional bedrooms and two full baths on this floor. Enjoy all the North Fork has to offer and more with the deeded right of way that comes with this home which provides convenient access to sought-after McCabe’s Beach! Kenney’s Beach is also just a stone’s throw away! Don’t miss the opportunity to create a vacation to remember with this special home! Two-week terms are also available. Appearance: Mint
      Presented By: Compass Greater NY LLC  516-517-4751
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY’S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY!, Additional information: Appearance:excellent!, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor, Off Season, Weekly, Weekly Rent Amt:3000 29
      250 Wesland Rd Southold, NY 11971
      $10,500
      2 Bedrooms 2 Full Baths Sq. Ft. 1400.00:#
      Single Family For Rent ML# 3478213
      NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY’S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY!, Additional information: Appearance:excellent!, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor, Off Season, Weekly, Weekly Rent Amt:3000
      Presented By: Beninati Associates  631-765-5333
      Call Today: 631-235-8980, 631-765-5333, or  Email: Marie Beninati
      Call Today: 631-765-5333, or  Email: Lee Beninati
    • Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Call for off-season rates. Close to all North Fork amenities. 35
      800 Goose Creek Lane Southold, NY 11971
      $9,500
      3 Bedrooms 3 Full Baths Sq. Ft. 2032.00:#
      Single Family For Rent ML# 3526789
      Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Call for off-season rates. Close to all North Fork amenities.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold Town Rental Permit #1016. Cozy Northern White Cedar Log Style Chalet With Heated Saltwater Pool. It is the juxtaposition between the rustic qualities and the elegant essence of this home that makes it so unique! Covered Wrap Around Porch. 2 Car Garage Attached, 1 Detached. Open Floor Plan. Two Spacious Bedrooms, The Primary Is En-Suite. Extra Loft Style Bedroom With Two Single Beds. Two Full Baths. Unique Smoke House. Appointed Details Inside This Home Were Skillfully Created By The Hands Of A Master Craftsman. Tucked Away On An Acre Property With Ample Privacy. The Perfect Home For Those Seeking A Secluded Vacation On The North Fork. Close Proximity To A Private Beach(Cedar Beach), Easy Access To The Water For Kayak Enthusiasts And A Ramp For Launching Small Crafts. Very Close To Goose Creek & Peconic Bay. Be Part Of What The North Fork Has To Offer: Pristine Beaches, Delectable Restaurants, Local Produce & A Burgeoning Wine Country. . May = $4000 per 2 week stay) (June = $5000 per 2 week stay) (July = $7500 per 2 week stay) (August = $10, 000 per 2 week stay) (September = $9000 per 2 weeks) (October Through April = $3500 per 2 week stay), Additional information: Appearance:Diamond+++, Weekly Renta Amt:1750 31
      380 Private Rd Southold, NY 11971
      $7,000
      2 Bedrooms 2 Full Baths Sq. Ft. 1500.00:#
      Single Family For Rent ML# 3517331
      Southold Town Rental Permit #1016. Cozy Northern White Cedar Log Style Chalet With Heated Saltwater Pool. It is the juxtaposition between the rustic qualities and the elegant essence of this home that makes it so unique! Covered Wrap Around Porch. 2 Car Garage Attached, 1 Detached. Open Floor Plan. Two Spacious Bedrooms, The Primary Is En-Suite. Extra Loft Style Bedroom With Two Single Beds. Two Full Baths. Unique Smoke House. Appointed Details Inside This Home Were Skillfully Created By The Hands Of A Master Craftsman. Tucked Away On An Acre Property With Ample Privacy. The Perfect Home For Those Seeking A Secluded Vacation On The North Fork. Close Proximity To A Private Beach(Cedar Beach), Easy Access To The Water For Kayak Enthusiasts And A Ramp For Launching Small Crafts. Very Close To Goose Creek & Peconic Bay. Be Part Of What The North Fork Has To Offer: Pristine Beaches, Delectable Restaurants, Local Produce & A Burgeoning Wine Country. . May = $4000 per 2 week stay) (June = $5000 per 2 week stay) (July = $7500 per 2 week stay) (August = $10, 000 per 2 week stay) (September = $9000 per 2 weeks) (October Through April = $3500 per 2 week stay), Additional information: Appearance:Diamond+++, Weekly Renta Amt:1750
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 11 - 20 of 21 results| view:  results per page« 1|2|3 »
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    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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