Fair Housing Notice Standard Operating Procedure
631.765.5333

Southold Homes with Pools

    to
     
     
     
    Search Search
    » Property Criteria
    » Features
    •  
    » Display Tools
    Search

    95  properties match your search;

    95 with Multiple photos ;  21 with Virtual Tour ;  4 with Videos

    Save Search
    Showing 31 - 40 of 95 results| view:  results per page« first|...|2|3|4|5|...|last »
    • Spanning 3.82 acres, this generous home seamlessly blends luxury with comfort. The formal entry opens to an oversized great room, where a soaring ceiling and a striking stone fireplace are complemented by a wet bar-perfect for entertaining. The kitchen, updated in 2023 with sleek stainless-steel appliances, counters, and backsplash, is a chef’s dream. Two well-sized bedrooms share a large full bath on the main floor, offering flexibility and convenience. Ascend to the second floor to discover a sprawling 1, 300 sq. ft. master suite, complete with walk-in closets, an office, and a luxurious master bath. Designed for an indoor-outdoor living experience, this home features a screened room leading to over 750 sq. ft. of IPE decking. The outdoor space is a true retreat, featuring a heated inground pool with a striking stone surround ideal for lounging and dining, all beautifully fenced and surrounded by meticulous landscaping. All systems in the home are regularly maintained, providing peace of mind. Additional highlights include radiant heated tile floors, ensuring year-round comfort and reliability. 32
      9390 N Bayview Rd Southold, NY 11971
      $1,850,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 3700.00:#
      Single Family For Sale ML# 3576752
      Spanning 3.82 acres, this generous home seamlessly blends luxury with comfort. The formal entry opens to an oversized great room, where a soaring ceiling and a striking stone fireplace are complemented by a wet bar-perfect for entertaining. The kitchen, updated in 2023 with sleek stainless-steel appliances, counters, and backsplash, is a chef’s dream. Two well-sized bedrooms share a large full bath on the main floor, offering flexibility and convenience. Ascend to the second floor to discover a sprawling 1, 300 sq. ft. master suite, complete with walk-in closets, an office, and a luxurious master bath. Designed for an indoor-outdoor living experience, this home features a screened room leading to over 750 sq. ft. of IPE decking. The outdoor space is a true retreat, featuring a heated inground pool with a striking stone surround ideal for lounging and dining, all beautifully fenced and surrounded by meticulous landscaping. All systems in the home are regularly maintained, providing peace of mind. Additional highlights include radiant heated tile floors, ensuring year-round comfort and reliability.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • A stylish, fully renovated ranch with soaring vaulted ceilings, featuring 4 bedrooms and 3 full baths. The generous open living space is highlighted by a gas fireplace, beautiful hardwood floors, and two large sliding doors leading out to the deck. The finished basement adds versatility to the floor plan. The home is complemented by a beautiful fenced-in yard and a brand-new heated saltwater pool. Perfect central location on the North Fork, minutes to beaches, wineries, shops, restaurants and Jitney. 15 minutes to Greenport and 25 minutes to the expressway and Westhampton. 23
      1480 Harbor Lane Southold, NY 11935
      $1,495,000
      4 Bedrooms 3 Full Baths Sq. Ft. 2430.00:#
      Single Family For Sale ML# 3576583
      A stylish, fully renovated ranch with soaring vaulted ceilings, featuring 4 bedrooms and 3 full baths. The generous open living space is highlighted by a gas fireplace, beautiful hardwood floors, and two large sliding doors leading out to the deck. The finished basement adds versatility to the floor plan. The home is complemented by a beautiful fenced-in yard and a brand-new heated saltwater pool. Perfect central location on the North Fork, minutes to beaches, wineries, shops, restaurants and Jitney. 15 minutes to Greenport and 25 minutes to the expressway and Westhampton.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This single-story gem offers three bedrooms and two full bathrooms. Step inside to a welcoming open-concept living area, graced with hardwood floors, beamed cathedral ceilings, and the warmth of a wood-burning fireplace. The kitchen is a delight, equipped with stainless steel appliances, granite counter tops and a second wood burning fireplace. The primary bedroom boasts a private ensuite. An added bonus is the full basement, offering ample storage space. Outside, enjoy the luxury of a Gunite, in-ground swimming pool, Anderson windows, an irrigation sprinkler system and the serenity of a private, dead-end street. Just around the corner, discover the beauty of a long island sound beach, perfect for leisurely strolls and soaking in the picturesque views. 36
      240 Stratmors Rd Southold, NY 11939
      $925,000
      3 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3575996
      This single-story gem offers three bedrooms and two full bathrooms. Step inside to a welcoming open-concept living area, graced with hardwood floors, beamed cathedral ceilings, and the warmth of a wood-burning fireplace. The kitchen is a delight, equipped with stainless steel appliances, granite counter tops and a second wood burning fireplace. The primary bedroom boasts a private ensuite. An added bonus is the full basement, offering ample storage space. Outside, enjoy the luxury of a Gunite, in-ground swimming pool, Anderson windows, an irrigation sprinkler system and the serenity of a private, dead-end street. Just around the corner, discover the beauty of a long island sound beach, perfect for leisurely strolls and soaking in the picturesque views.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to your dream home in the heart of North Fork’s renowned wine country! This stunning new construction, completed in 2024, offers the perfect blend of modern luxury and timeless elegance. Nestled just steps away from the serene waterfront and a mere five-minute drive from the charming downtown of Greenport and its surrounding wineries, this custom-built masterpiece is an unparalleled find. Spanning 4, 122 square feet, this home boasts 5 spacious bedrooms and 4.5 beautifully appointed bathrooms. The moment you step inside, you’ll be captivated by the 22-foot vaulted ceilings that create an open, airy ambiance. The living area is anchored by a cozy gas fireplace, perfect for chilly evenings, while the gourmet kitchen is a chef’s delight. It features pristine quartz countertops, a center island with a dramatic waterfall edge, and top-of-the-line appliances. Entertain in style in the elegant dining room, complete with a bar and wine fridge-ideal for holiday gatherings or intimate dinners. The main floor also includes a convenient laundry room and a mudroom with direct access to the backyard porch. Exquisite details abound, from the glass panel railings and custom wood ceiling beams to the rich 7-inch oak wood plank floors that run throughout the home. The primary suite, located on the first floor, is a true retreat with sliding glass doors that open to the outdoor porch-perfect for unwinding with a glass of local wine as you watch the sunset. The suite also features spacious walk-in closets and a luxurious en-suite bathroom with a large soaking tub for ultimate relaxation. The second floor is equally impressive, offering four additional bedrooms, each with ample closet space, and two full bathrooms. Designed with entertainment in mind, the backyard is a private oasis, complete with an outdoor kitchen and a stunning in-ground pool. This home is a sanctuary where family and guests can gather, relax, and create lasting memories. Don’t miss this rare opportunity to own a piece of paradise in one of Long Island’s most sought-after locations. 72
      2060 Shipyard Lane Southold, NY 11939
      $2,099,999
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4122.00:#
      Single Family For Sale ML# 3574213
      Welcome to your dream home in the heart of North Fork’s renowned wine country! This stunning new construction, completed in 2024, offers the perfect blend of modern luxury and timeless elegance. Nestled just steps away from the serene waterfront and a mere five-minute drive from the charming downtown of Greenport and its surrounding wineries, this custom-built masterpiece is an unparalleled find. Spanning 4, 122 square feet, this home boasts 5 spacious bedrooms and 4.5 beautifully appointed bathrooms. The moment you step inside, you’ll be captivated by the 22-foot vaulted ceilings that create an open, airy ambiance. The living area is anchored by a cozy gas fireplace, perfect for chilly evenings, while the gourmet kitchen is a chef’s delight. It features pristine quartz countertops, a center island with a dramatic waterfall edge, and top-of-the-line appliances. Entertain in style in the elegant dining room, complete with a bar and wine fridge-ideal for holiday gatherings or intimate dinners. The main floor also includes a convenient laundry room and a mudroom with direct access to the backyard porch. Exquisite details abound, from the glass panel railings and custom wood ceiling beams to the rich 7-inch oak wood plank floors that run throughout the home. The primary suite, located on the first floor, is a true retreat with sliding glass doors that open to the outdoor porch-perfect for unwinding with a glass of local wine as you watch the sunset. The suite also features spacious walk-in closets and a luxurious en-suite bathroom with a large soaking tub for ultimate relaxation. The second floor is equally impressive, offering four additional bedrooms, each with ample closet space, and two full bathrooms. Designed with entertainment in mind, the backyard is a private oasis, complete with an outdoor kitchen and a stunning in-ground pool. This home is a sanctuary where family and guests can gather, relax, and create lasting memories. Don’t miss this rare opportunity to own a piece of paradise in one of Long Island’s most sought-after locations.
      Presented By: OverSouth LLC  631-770-0030
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Orient, The Hill. Perched high on a hill above the Long Island Sound, is this exceptional offering in the coveted The Hill historic estate enclave. Authentic, classic, grand. Architectural details include 5 fireplaces, 16/1 windows, front entry door with sidelight panes. Beautiful landscape, hardscape, paths and plantings adorn this rolling 1.3 acre property. Swimming pool. 6 bedrooms 4.5 baths. Generous size rooms and waterside screened porch. Stunning sunsets. Owned by the same family for 65 years. The next one could be yours. A truly special Orient property. The possibilities are endless. Set above the stretch where the Sound meets the Bay, it doesn’t get any more North Fork than this! 31
      825 Munn Lane Southold, NY 11957
      $2,800,000
      6 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Sale ML# 3573568
      Orient, The Hill. Perched high on a hill above the Long Island Sound, is this exceptional offering in the coveted The Hill historic estate enclave. Authentic, classic, grand. Architectural details include 5 fireplaces, 16/1 windows, front entry door with sidelight panes. Beautiful landscape, hardscape, paths and plantings adorn this rolling 1.3 acre property. Swimming pool. 6 bedrooms 4.5 baths. Generous size rooms and waterside screened porch. Stunning sunsets. Owned by the same family for 65 years. The next one could be yours. A truly special Orient property. The possibilities are endless. Set above the stretch where the Sound meets the Bay, it doesn’t get any more North Fork than this!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This Incredible Home is Now Available for Off Season Rental from September 1, 2024 - March 31, 2025 and Memorial - Labor Day 2025. 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 37
      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 Sale ML# 3573270
      This Incredible Home is Now Available for Off Season Rental from September 1, 2024 - March 31, 2025 and Memorial - Labor Day 2025. 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
      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. 29
      11925 Soundview Avenue Southold, NY 11971
      $12,500
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3600.00:#
      Single Family For Sale 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.
      Presented By: Compass Greater NY LLC  516-517-4751
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Charming and inviting property in the Orient By The Sea beach community. Desirable half-acre corner lot property. Three bedroom, one and a half bath Colonial with two car garage. This home boasts a welcoming living room with a wood-burning fireplace, adjacent to a cozy sitting room with a wood-burning stove. Large eat-in kitchen with barstool countertop. The dining area has sliding glass doors that lead to a backyard oasis, which includes an awning-covered deck, a 20x40 in-ground saltwater pool with patio surround, and an outdoor shower. Also full basement with tons of potential! The private community beach is a short distance from the home! Located close to the Cross Sound Ferry, Orient State Park, and 10 mins to the heart of Greenport Village. Nature and serenity abound with nearby hiking trails, glorious beaches, and breathtaking sunsets. 26
      1365 Plum Island Lane Southold, NY 11957
      $995,000
      $975,000
      3 Bedrooms 1 Full Bath 1 Half Bath
      Single Family For Sale PRICE REDUCED ML# 3570792
      Charming and inviting property in the Orient By The Sea beach community. Desirable half-acre corner lot property. Three bedroom, one and a half bath Colonial with two car garage. This home boasts a welcoming living room with a wood-burning fireplace, adjacent to a cozy sitting room with a wood-burning stove. Large eat-in kitchen with barstool countertop. The dining area has sliding glass doors that lead to a backyard oasis, which includes an awning-covered deck, a 20x40 in-ground saltwater pool with patio surround, and an outdoor shower. Also full basement with tons of potential! The private community beach is a short distance from the home! Located close to the Cross Sound Ferry, Orient State Park, and 10 mins to the heart of Greenport Village. Nature and serenity abound with nearby hiking trails, glorious beaches, and breathtaking sunsets.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Best of Both Worlds - Enjoy The Seclusion Of This 2 Acre Parcel, Yet Close To Town, Shopping, Beaches & Vineyards. Photos Shown Are From Identical House Recently Completed In Southold. Easy To Preview! 61
      1350 Hortons Lane Southold, NY 11971
      $2,995,000
      8 Bedrooms 7 Full Baths Sq. Ft. 5600.00:#
      Single Family For Sale ML# 3569381
      Best of Both Worlds - Enjoy The Seclusion Of This 2 Acre Parcel, Yet Close To Town, Shopping, Beaches & Vineyards. Photos Shown Are From Identical House Recently Completed In Southold. Easy To Preview!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Mattituck, North Fork: The House on The Hill - Saltaire Estates Classic Colonial by Bailey Beach. Living Room w/FP and Den w/FP, formal DR, EIK, 4 bedrooms, 3 full baths. Full basement. Inground pool with level yard ideal for entertaining. Moments to Bailey Beach and Saltaire Association Parks on the Sound and tennis and basketball. Convenient to village of Mattituck. 37
      2850 Reeve Rd Southold, NY 11952
      $1,149,000
      4 Bedrooms 3 Full Baths Sq. Ft. 2150.00:#
      Single Family For Sale ML# 3568549
      Mattituck, North Fork: The House on The Hill - Saltaire Estates Classic Colonial by Bailey Beach. Living Room w/FP and Den w/FP, formal DR, EIK, 4 bedrooms, 3 full baths. Full basement. Inground pool with level yard ideal for entertaining. Moments to Bailey Beach and Saltaire Association Parks on the Sound and tennis and basketball. Convenient to village of Mattituck.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 31 - 40 of 95 results| view:  results per page« first|...|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

    Questions? Just Ask!

     Submit
    Office: 52875 Main Road, Southold NY 11971
    631.765.5333     powered by eRealty Media | Admin