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Southold Luxury Homes for Sale

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    Showing 11 - 20 of 20 results| view:  results per page« 1|2 »
    • Designer Modern Farmhouse set on over 3.35 Acres with farm and scenic views, Renovated 2023, Open Concept LR/DR/KIT, Gorgeous KIT with quartz countertops, SS Appl., new, new, new, windows, interior and exterior doors, flooring throughout, baths, boiler, well pump and tank, hot water heater, spectacular 20x40 in ground pool with Cambridge paver patio, front porch. Close to McCabe beach or quick drive for incredible sunsets. Access to Resident only Town beaches, boat ramps and parks with town permit. Farm animals permitted. Marina, and airstrip nearby. 28
      3715 Hortons Lane Southold, NY 11971
      $1,850,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3100.00:#
      Single Family For Sale ML# 3582082
      Designer Modern Farmhouse set on over 3.35 Acres with farm and scenic views, Renovated 2023, Open Concept LR/DR/KIT, Gorgeous KIT with quartz countertops, SS Appl., new, new, new, windows, interior and exterior doors, flooring throughout, baths, boiler, well pump and tank, hot water heater, spectacular 20x40 in ground pool with Cambridge paver patio, front porch. Close to McCabe beach or quick drive for incredible sunsets. Access to Resident only Town beaches, boat ramps and parks with town permit. Farm animals permitted. Marina, and airstrip nearby.
      Presented By: Coldwell Banker American Homes  516-302-8500
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 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. 31
      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
    • Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76, 230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the ’tower’ of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!, Additional information: Appearance:immaculate, Interior Features:Lr/Dr 36
      2055 Boisseau Avenue Southold, NY 11971
      $1,599,000
      3 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 2000.00:#
      Single Family For Sale ML# 3590177
      Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76, 230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a spacious living room with a fireplace. The dining room can function as a den and includes pocket doors. The primary floor also offers an eat-in kitchen, a laundry room/pantry, a 3-season room, a full bath, and a back staircase. Upstairs, you will find three large bedrooms and another full bath. The farmhouse retains historic character and details, including original wainscoting, paneled doors, windows, and hardwood floors. Various unique features from a bygone era include a laundry chute, a built-in medicine cabinet, bench seats and cabinets, and a sewing room or nursery that could also serve as a walk-in closet. Additionally, the property includes a two-car garage, a post-and-beam barn (which previously hosted generations of local school dances), a large two-story workshop, and a tool shed, along with the ’tower’ of the windmill that once pumped water for the farm. With approximately 200 linear feet of road frontage, this home offers substantial privacy and is ideal for those seeking a true North Fork residence within a village setting with access to Southold Park District amenities including use of the Wharf House. You can have it all at 2055 Boisseau Avenue, with room for a pool or tennis court, horses, or small-scale farming. The barn can accommodate multiple boats or cars. Follow your dreams and explore this incredible opportunity!, Additional information: Appearance:immaculate, Interior Features:Lr/Dr
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you’re greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1, 400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney’s Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether you are meandering east towards Horton’s Point Lighthouse or west towards Goldsmith’s Inlet, the journey is as captivating as the destination. The nearby 60-acre nature trail just down the beach invites leisurely exploration, enhancing the natural allure of the area. Perfect for those who cherish peace, privacy, and the unique beauty of coastal living, this home offers promising unforgettable sunsets and a tranquil lifestyle nestled in a coveted private beach community. 35
      350 West Drive Southold, NY 11971
      $1,395,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1900.00:#
      Single Family For Sale ML# 3554407
      Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you’re greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1, 400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney’s Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether you are meandering east towards Horton’s Point Lighthouse or west towards Goldsmith’s Inlet, the journey is as captivating as the destination. The nearby 60-acre nature trail just down the beach invites leisurely exploration, enhancing the natural allure of the area. Perfect for those who cherish peace, privacy, and the unique beauty of coastal living, this home offers promising unforgettable sunsets and a tranquil lifestyle nestled in a coveted private beach community.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • A must see secluded water front Compound. Rarely do you find two houses on a one acre lot. Main cottage is 3 BR, Eik, FDR, , LR with fireplace, hardwood floors, basement and inviting water side covered porch, second cottage has Primary ensuite and guest Br with second bath, Eik, LR w/Fireplace hardwood floors full basement. Small out building, Additional information: Appearance:Very good 36
      633 Pine Neck Rd Southold, NY 11971
      $1,349,000
      3 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 1068.00:#
      Single Family For Sale ML# 3487080
      A must see secluded water front Compound. Rarely do you find two houses on a one acre lot. Main cottage is 3 BR, Eik, FDR, , LR with fireplace, hardwood floors, basement and inviting water side covered porch, second cottage has Primary ensuite and guest Br with second bath, Eik, LR w/Fireplace hardwood floors full basement. Small out building, Additional information: Appearance:Very good
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome Home to this sunny 3-bedroom, 2.5-bath Equestrian home built in 2001set on a sprawling 1.94-acre lot with 2-stall horse barn! Full basement with 8ft ceilings & OSE to yard, 2-car attached garage & fenced horse pasture. Formal Living Room with Vaulted ceilings, Formal dining room, large EIK with sliders to rear deck & patio. Large Primary bedroom suite with bathroom, large WIC and views of the yard. 2 Additional Spacious bedrooms & full bath complete the second floor. Oak hardwood flooring throughout house. New CAC system & newer heating coil in burner. Barn is a well-constructed 24 x 24 Pole Barn with electric & water on cement slab with footings w/ Hardie board & T-111 siding. Accessory shed for hay & horse supplies included. Room for Pool!! Act fast! This property will not last!!, Additional information: Appearance:Mint, Separate Hotwater Heater:N 21
      1500 Hortons Lane Southold, NY 11971
      $1,250,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1900.00:#
      Single Family For Sale ML# 3555058
      Welcome Home to this sunny 3-bedroom, 2.5-bath Equestrian home built in 2001set on a sprawling 1.94-acre lot with 2-stall horse barn! Full basement with 8ft ceilings & OSE to yard, 2-car attached garage & fenced horse pasture. Formal Living Room with Vaulted ceilings, Formal dining room, large EIK with sliders to rear deck & patio. Large Primary bedroom suite with bathroom, large WIC and views of the yard. 2 Additional Spacious bedrooms & full bath complete the second floor. Oak hardwood flooring throughout house. New CAC system & newer heating coil in burner. Barn is a well-constructed 24 x 24 Pole Barn with electric & water on cement slab with footings w/ Hardie board & T-111 siding. Accessory shed for hay & horse supplies included. Room for Pool!! Act fast! This property will not last!!, Additional information: Appearance:Mint, Separate Hotwater Heater:N
      Presented By: Gateway to The Hamptons R E  631-325-3449
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Adorable Beach Bungalow Getaway!!! Kenney’s Beach practically at your doorstep. There’s room for everyone in the 4 BR, 2 BA home with two decks to enjoy morning coffee and beautiful sunsets. 13
      65 Lake Drive Southold, NY 11971
      $1,200,000
      4 Bedrooms 2 Full Baths Sq. Ft. 1500.00:# Square Feet
      Single Family For Sale NEW ML# 804563
      Adorable Beach Bungalow Getaway!!! Kenney’s Beach practically at your doorstep. There’s room for everyone in the 4 BR, 2 BA home with two decks to enjoy morning coffee and beautiful sunsets.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Newly renovated home in a coveted private beach community! Classic expanded Saltbox with open concept floor plan and high-beamed ceilings finished in a timeless Nantucket style! Completely renovated in 2020-2021, this move-in ready home boasts 3 bedrooms, including a primary with en-suite bath and, a large second-level loft with clerestory windows that is convertible to a fourth bedroom. The living room has a beautiful wood-burning fireplace and sliders to an antique-style real brick 17x40 outdoor dining, and lounging patio with an integrated firepit! This spectacular pond-front property has unobstructed Southern views across the Bay to the South Shore from the second level. Located in one of the most prestigious areas of Southold in a quiet, private association community with Creek access and a private community beach. The quintessential North Fork Beach house!! NOT IN FLOOD ZONE! 34
      55 Cedar Point West Drive Southold, NY 11971
      $1,199,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1650.00:#
      Single Family For Sale ML# 3585163
      Newly renovated home in a coveted private beach community! Classic expanded Saltbox with open concept floor plan and high-beamed ceilings finished in a timeless Nantucket style! Completely renovated in 2020-2021, this move-in ready home boasts 3 bedrooms, including a primary with en-suite bath and, a large second-level loft with clerestory windows that is convertible to a fourth bedroom. The living room has a beautiful wood-burning fireplace and sliders to an antique-style real brick 17x40 outdoor dining, and lounging patio with an integrated firepit! This spectacular pond-front property has unobstructed Southern views across the Bay to the South Shore from the second level. Located in one of the most prestigious areas of Southold in a quiet, private association community with Creek access and a private community beach. The quintessential North Fork Beach house!! NOT IN FLOOD ZONE!
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150., Additional information: Interior Features:Lr/Dr 32
      1755 Yennecott Drive Southold, NY 11971
      $1,100,000
      6 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 3200.00:#
      Single Family For Sale ML# 3509055
      Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150., Additional information: Interior Features:Lr/Dr
      Presented By: Richmond Realty Corp  631-727-5500
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to this beautiful, fully renovated home, where classic charm meets modern luxury. Nestled in a serene neighborhood, this exceptional property offers an inviting open floor plan, highlighted by elegant finishes and thoughtful updates throughout. The main level features a spacious living room with a cozy fireplace, seamlessly flowing into a brand new beautiful kitchen equipped with top-of-the-line stainless steel appliances, sleek countertops, and custom cabinetry. Adjacent to the kitchen, the dining area is perfect for both everyday meals and entertaining guests. The main level also includes a luxurious bedroom and a spa-like en-suite bathroom, as well as an additional family room and half bathroom. Upstairs, you’ll find three generously sized bedrooms with ample closet space, as well as a beautiful brand new full bathroom. Outside, the expansive backyard provides a private oasis with a patio area, perfect for outdoor gatherings and summer barbecues. Additional Highlights include New siding, New roof, New doors, New floors, New electrical and plumbing systems, New kitchen, New bathrooms, New Anderson windows and a Two Car Garage. Don’t miss the opportunity to make this beautifully renovated home yours! 36
      1475 Oaklawn Avenue Southold, NY 11971
      $1,024,000
      4 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Sale ML# 3573918
      Welcome to this beautiful, fully renovated home, where classic charm meets modern luxury. Nestled in a serene neighborhood, this exceptional property offers an inviting open floor plan, highlighted by elegant finishes and thoughtful updates throughout. The main level features a spacious living room with a cozy fireplace, seamlessly flowing into a brand new beautiful kitchen equipped with top-of-the-line stainless steel appliances, sleek countertops, and custom cabinetry. Adjacent to the kitchen, the dining area is perfect for both everyday meals and entertaining guests. The main level also includes a luxurious bedroom and a spa-like en-suite bathroom, as well as an additional family room and half bathroom. Upstairs, you’ll find three generously sized bedrooms with ample closet space, as well as a beautiful brand new full bathroom. Outside, the expansive backyard provides a private oasis with a patio area, perfect for outdoor gatherings and summer barbecues. Additional Highlights include New siding, New roof, New doors, New floors, New electrical and plumbing systems, New kitchen, New bathrooms, New Anderson windows and a Two Car Garage. Don’t miss the opportunity to make this beautifully renovated home yours!
      Presented By: Keller Williams Points North  516-865-1800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 11 - 20 of 20 results| view:  results per page« 1|2 »
    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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