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Southold Homes for Rent

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    Showing 11 - 20 of 53 results| view:  results per page« 1|2|3|4|5|...|last »
    • Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep. 11
      470 Goose Creek Lane Southold, NY 11971
      $30,000
      3 Bedrooms 2 Full Baths Sq. Ft. 2000.00:#
      Single Family For Rent ML# 3236473
      Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a fireplace, a formal dining room, a den, a large kitchen, and a pantry. Upstairs, there are five bedrooms, three baths, PLUS, an outdoor shower convenient for all to enjoy. The outbuilding, known as The Birdhouse, offers dormitory space for overflow guests with a private bathroom. The estate has a direct beachfront setting, with sugar sand and carefree days awaiting visitors in an old-fashioned East End seaside cottage. Permit# 0996 32
      1695 Old Woods Path Southold, NY 11971
      $30,000
      6 Bedrooms 4 Full Baths
      Single Family For Rent ML# 3212687
      Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a fireplace, a formal dining room, a den, a large kitchen, and a pantry. Upstairs, there are five bedrooms, three baths, PLUS, an outdoor shower convenient for all to enjoy. The outbuilding, known as The Birdhouse, offers dormitory space for overflow guests with a private bathroom. The estate has a direct beachfront setting, with sugar sand and carefree days awaiting visitors in an old-fashioned East End seaside cottage. Permit# 0996
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living Spaces. Its Picturesque Waterfront Setting Serving As A Constant Reminder Of The Beauty That Surrounds You. Here, You Can Start Your Day With A Refreshing Morning Jog, Entertain Guests With A Backyard Barbecue, Or Unwind With A Glass Of Wine While Watching The Sunset Over The Water. 1100 Pine Ave Is More Than Just An Address; It’s The Perfect Summer Getaway. Call Today To Schedule Your Private Tour. 19
      1100 Pine Avenue Southold, NY 11971
      $28,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3532447
      Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living Spaces. Its Picturesque Waterfront Setting Serving As A Constant Reminder Of The Beauty That Surrounds You. Here, You Can Start Your Day With A Refreshing Morning Jog, Entertain Guests With A Backyard Barbecue, Or Unwind With A Glass Of Wine While Watching The Sunset Over The Water. 1100 Pine Ave Is More Than Just An Address; It’s The Perfect Summer Getaway. Call Today To Schedule Your Private Tour.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      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. 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.
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it’s own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental’s paddle board, 2 kayaks, and beach buggy wagon. July $17, 000, August to Labor Day $24, 000, September $12, 000. 30
      6430 Hortons Lane Southold, NY 11971
      $24,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent ML# 3556906
      Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it’s own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental’s paddle board, 2 kayaks, and beach buggy wagon. July $17, 000, August to Labor Day $24, 000, September $12, 000.
      Presented By: Town And Country Real Estate  631-288-3030
      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. 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.
      Presented By: Brown Harris Stevens N Fork  631-477-0551
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Beachfront, located in Southold Shores, this architect’s own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite, seaside floor to ceiling windows overlooking the Bayfront, Chefs kitchen leading to large outdoor deck and lovely garden. It is truly stunning. A special summer oasis. Available August $40K, Sept $20K RP# 0857 34
      950 Blue Marlin Drive Southold, NY 11971
      $20,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3200.00:#
      Single Family For Rent ML# 3376195
      Beachfront, located in Southold Shores, this architect’s own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite, seaside floor to ceiling windows overlooking the Bayfront, Chefs kitchen leading to large outdoor deck and lovely garden. It is truly stunning. A special summer oasis. Available August $40K, Sept $20K RP# 0857
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107 RATES: MD-LD $19, 000 ; June $3500; July $7, 000’ Aug-LD $8, 000 July/Aug-LD $15, 000 - off season/Fall 2025 available. 13
      Southold, NY 11971
      $19,000
      1 Bedroom 1 Full Bath Sq. Ft. 750.00:#
      Single Family For Rent ML# 3525718
      Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107 RATES: MD-LD $19, 000 ; June $3500; July $7, 000’ Aug-LD $8, 000 July/Aug-LD $15, 000 - off season/Fall 2025 available.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with ’bar’ area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26 31
      50 Wabasso Street Southold, NY 11971
      $18,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1200.00:#
      Single Family For Rent ML# 3559692
      Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with ’bar’ area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 11 - 20 of 53 results| view:  results per page« 1|2|3|4|5|...|last »
    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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