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Southold Homes for Sale

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    • A long winding driveway rises to this spectacular 56 acre property and beautifully built five bedroom 3.1 bath home. Commanding unsurpassed views of preserved land and LI Sound beyond- breathtaking! Here you will always have a captivating setting of peaceful pastoral beauty from all directions. The pristine well cared for home has nearly five thousand feet of living area- a grand foyer, spacious living room- perfect for entertaining. The first floor primary ensuite has a fireplace and sitting area with stunning views, The formal dining room opens to the granite chef’s kitchen and there is also a huge four season sunroom with fireplace. Three more bedrooms on the first floor, plus cozy den. Upstairs is an additional bedroom, studio, and bath with both inside and outside entrances- perfect for additional guest area. Enjoy the spectacular views by one of the 4 fireplaces in this home, or outside by the fire pit at sunset. A stones throw to Bailies Beach, and close to wineries, farm to table restaurants, and Love Lane. A historic barn, and possible working farm with large greenhouses as well. This huge property can also serve as your dream equestrian setting. 48 acres have been preserved and 8 acres have development rights in tact. No other Long Island property comes close! Frontage on two of the most beautiful roads on the North Fork- this property is truly special. 66
      Southold, NY 11952
      $7,500,000
      5 Bedrooms 3 Full Baths 2 Half Baths Sq. Ft. 4835.00:#
      Single Family For Sale ML# 3513901
      A long winding driveway rises to this spectacular 56 acre property and beautifully built five bedroom 3.1 bath home. Commanding unsurpassed views of preserved land and LI Sound beyond- breathtaking! Here you will always have a captivating setting of peaceful pastoral beauty from all directions. The pristine well cared for home has nearly five thousand feet of living area- a grand foyer, spacious living room- perfect for entertaining. The first floor primary ensuite has a fireplace and sitting area with stunning views, The formal dining room opens to the granite chef’s kitchen and there is also a huge four season sunroom with fireplace. Three more bedrooms on the first floor, plus cozy den. Upstairs is an additional bedroom, studio, and bath with both inside and outside entrances- perfect for additional guest area. Enjoy the spectacular views by one of the 4 fireplaces in this home, or outside by the fire pit at sunset. A stones throw to Bailies Beach, and close to wineries, farm to table restaurants, and Love Lane. A historic barn, and possible working farm with large greenhouses as well. This huge property can also serve as your dream equestrian setting. 48 acres have been preserved and 8 acres have development rights in tact. No other Long Island property comes close! Frontage on two of the most beautiful roads on the North Fork- this property is truly special.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Southold, Paradise Point Bayfront. Private peninsula in Paradise Point Community. Water on 3 sides with sweeping, open views across Southold Bay to Shelter Island and beyond. This unique waterfront setting includes 994 feet of shoreline and a deep-water dock in a protected boat basin. Approach this 5, 100 sq. ft. home from the circular drive. Beautiful plantings frame the entry. Step into the grand entry foyer of this 2 story, 4 bedroom, 3.5 bath Nantucket style residence, with views through the foyer and house onto the open bay. A dramatic and exquisite first impression. High ceilings, huge gracious rooms. An open first floor design, living room with wood burning fireplace. Expansive windows, glass doors and transoms allow flow to the large outside wrap around waterside porch. Incredible light, and extraordinary sunset views. Oak floors throughout. First floor sitting room with gas fireplace and an office/den alcove. Huge chef’s kitchen, with stainless appliances and granite counters, overlooking the bay and pool. Space for casual dining in kitchen, and a formal dining room overlooking the boat basin. Laundry room, one bayside en-suite primary bedroom, and an additional half bath complete the first floor. Second floor primary en-suite bedroom and sitting room with magnificent views over the pool and open bay. 2 additional large bedrooms with water views and additional full bath. The open second floor landing boasts sweeping water views. Elevator accessed by 3 floors, generator, spacious walkout basement waiting for your imagination with endless possibilities. Waterside heated pool and 2 car garage. 1.8 acres. Specimen plantings. Beautiful shoreline landscaping. If you are looking for an exceptional home and property, this is it. 36
      Southold, NY 11971
      $5,350,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 5080.00:# Square Feet
      Single Family For Sale ML# 3563000
      Southold, Paradise Point Bayfront. Private peninsula in Paradise Point Community. Water on 3 sides with sweeping, open views across Southold Bay to Shelter Island and beyond. This unique waterfront setting includes 994 feet of shoreline and a deep-water dock in a protected boat basin. Approach this 5, 100 sq. ft. home from the circular drive. Beautiful plantings frame the entry. Step into the grand entry foyer of this 2 story, 4 bedroom, 3.5 bath Nantucket style residence, with views through the foyer and house onto the open bay. A dramatic and exquisite first impression. High ceilings, huge gracious rooms. An open first floor design, living room with wood burning fireplace. Expansive windows, glass doors and transoms allow flow to the large outside wrap around waterside porch. Incredible light, and extraordinary sunset views. Oak floors throughout. First floor sitting room with gas fireplace and an office/den alcove. Huge chef’s kitchen, with stainless appliances and granite counters, overlooking the bay and pool. Space for casual dining in kitchen, and a formal dining room overlooking the boat basin. Laundry room, one bayside en-suite primary bedroom, and an additional half bath complete the first floor. Second floor primary en-suite bedroom and sitting room with magnificent views over the pool and open bay. 2 additional large bedrooms with water views and additional full bath. The open second floor landing boasts sweeping water views. Elevator accessed by 3 floors, generator, spacious walkout basement waiting for your imagination with endless possibilities. Waterside heated pool and 2 car garage. 1.8 acres. Specimen plantings. Beautiful shoreline landscaping. If you are looking for an exceptional home and property, this is it.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Experience summer camp bliss at 2480 & 2335 Minnehaha Blvd, Southold. This quintessential Nantucket-style cedar shake home offers expansive bayfront views, picturesque sandbars, and a pristine beachy landscape. Featuring charming Dutch doors, expansive decks, and an open floor plan, the gourmet kitchen flows into a cozy living room with a built-in wet bar, ideal for enjoying the serene waterfront vistas. A state-of-the-art golf simulator adds a playful touch, while riparian rights and a private dock accommodate a 66’ yacht. With multiple decks, a man-made beach on Corey Creek, and access to the Laughing Waters HOA beach, this property is a true waterfront retreat. Perfect for nature lovers and their pets, it’s a lifestyle where every day feels like summer camp. 37
      Southold, NY 11971
      $3,456,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2800.00:#
      Single Family For Sale ML# 3559554
      Experience summer camp bliss at 2480 & 2335 Minnehaha Blvd, Southold. This quintessential Nantucket-style cedar shake home offers expansive bayfront views, picturesque sandbars, and a pristine beachy landscape. Featuring charming Dutch doors, expansive decks, and an open floor plan, the gourmet kitchen flows into a cozy living room with a built-in wet bar, ideal for enjoying the serene waterfront vistas. A state-of-the-art golf simulator adds a playful touch, while riparian rights and a private dock accommodate a 66’ yacht. With multiple decks, a man-made beach on Corey Creek, and access to the Laughing Waters HOA beach, this property is a true waterfront retreat. Perfect for nature lovers and their pets, it’s a lifestyle where every day feels like summer camp.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Welcome to 1405 Terry Lane, Orient, a fully renovated waterfront residence with a private beach that extends for miles in each direction and a new, heated 12 x 30in-ground pool with views overlooking the Long Island Sound. Situated on 1.63 acres at the end of a private road, a remote gated entrance opens to a white stone driveway that passes by a private half acre vineyard and consummates at the 3 bedrooms, 2.5 bathroom home with the master bedroom with en-suite bathroom on the first floor. The home has hardwood floors throughout, a modern kitchen with expansive views of the Long Island Sound, a four seasons room that leads to a spacious deck with awnings and all of the amenities one could ask for when entertaining guests. The sprawling lawns have manicured landscaping and plantings, providing privacy, incredible sunsets and a serene environment. 72
      Southold, NY 11957
      $3,395,000
      $3,295,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2200.00:#
      Single Family For Sale PRICE REDUCED ML# 3577749
      Welcome to 1405 Terry Lane, Orient, a fully renovated waterfront residence with a private beach that extends for miles in each direction and a new, heated 12 x 30in-ground pool with views overlooking the Long Island Sound. Situated on 1.63 acres at the end of a private road, a remote gated entrance opens to a white stone driveway that passes by a private half acre vineyard and consummates at the 3 bedrooms, 2.5 bathroom home with the master bedroom with en-suite bathroom on the first floor. The home has hardwood floors throughout, a modern kitchen with expansive views of the Long Island Sound, a four seasons room that leads to a spacious deck with awnings and all of the amenities one could ask for when entertaining guests. The sprawling lawns have manicured landscaping and plantings, providing privacy, incredible sunsets and a serene environment.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • A true coastal paradise where the line between home and horizon blurs into one breathtaking Bayfront panorama. Situated mere steps from the water’s edge, this 4-bed, 2-bath home offers an immersive waterfront experience with the sensation of being aboard a boat providing 180-degree water views that captivate the eye from every vantage point. Whether you’re lounging on the sun-drenched waterside deck or hosting a sunset soiree, the Bay serves as the perfect backdrop to your plans. Inside offers a spacious open floor plan of kitchen, living, and dining, with large windows and a sliding glass door that frame the water. Imagine waking up to the gentle sounds of the waves and opening your eyes to the blue waters as all the spacious bedrooms upstairs have their own beautiful view. Additionally, there’s a dry bar with several refrigeration spaces and an ice maker, a separate 1-car garage with an attached bonus room to provide ample storage and versatility for your needs, and an outdoor shower. Close to North Fork vineyards, farm stands, fine dining, Love Lane, Strong’s Marina, etc. For those who crave the ’coastal living’ life, this is it! 27
      Southold, NY 11952
      $2,200,000
      4 Bedrooms 2 Full Baths Sq. Ft. 1845.00:#
      Single Family For Sale ML# 3552341
      A true coastal paradise where the line between home and horizon blurs into one breathtaking Bayfront panorama. Situated mere steps from the water’s edge, this 4-bed, 2-bath home offers an immersive waterfront experience with the sensation of being aboard a boat providing 180-degree water views that captivate the eye from every vantage point. Whether you’re lounging on the sun-drenched waterside deck or hosting a sunset soiree, the Bay serves as the perfect backdrop to your plans. Inside offers a spacious open floor plan of kitchen, living, and dining, with large windows and a sliding glass door that frame the water. Imagine waking up to the gentle sounds of the waves and opening your eyes to the blue waters as all the spacious bedrooms upstairs have their own beautiful view. Additionally, there’s a dry bar with several refrigeration spaces and an ice maker, a separate 1-car garage with an attached bonus room to provide ample storage and versatility for your needs, and an outdoor shower. Close to North Fork vineyards, farm stands, fine dining, Love Lane, Strong’s Marina, etc. For those who crave the ’coastal living’ life, this is it!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • One of a kind, Orient Village dream home! This converted Firehouse boasts over 4000sf, 4 bedrooms, 4 full bathrooms, an open concept living space on both floors, 12ft ceilings, and unique features you won’t find anywhere else. Conveniently located in the Village with close proximity to the beach. The primary bedroom has an ensuite bathroom and a private screened-in porch. The kitchen was recently updated with Viking appliances, high ceilings with exposed beams, and access to the sun deck. In addition to the updated kitchen, other updates include new electrical, updated central air, new gutters, and new dry wells. There is also a legal second kitchen great for prepping food. This home is truly an entertainer’s or artist’s paradise with easy-to-manage outdoor space. Outdoor Shower. Located on one of the most desirable and charming streets in Orient Village. 68
      Southold, NY 11957
      $2,195,000
      4 Bedrooms 4 Full Baths Sq. Ft. 4000.00:#
      Single Family For Sale ML# 3564345
      One of a kind, Orient Village dream home! This converted Firehouse boasts over 4000sf, 4 bedrooms, 4 full bathrooms, an open concept living space on both floors, 12ft ceilings, and unique features you won’t find anywhere else. Conveniently located in the Village with close proximity to the beach. The primary bedroom has an ensuite bathroom and a private screened-in porch. The kitchen was recently updated with Viking appliances, high ceilings with exposed beams, and access to the sun deck. In addition to the updated kitchen, other updates include new electrical, updated central air, new gutters, and new dry wells. There is also a legal second kitchen great for prepping food. This home is truly an entertainer’s or artist’s paradise with easy-to-manage outdoor space. Outdoor Shower. Located on one of the most desirable and charming streets in Orient Village.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Welcome to 12910 Main Road, located in the heart of East Marion. This recently updated waterfront property boasts over 70 feet of pristine beachfront along Gardiners Bay, offering breathtaking panoramic water views and stunning sunrises to the southeast. The main house features a luxurious primary en suite bedroom on the second floor, complete with a private balcony, while the open kitchen and living area provide captivating water views from every angle. Enhancing this exceptional property is a charming, fully updated legal guest cottage, which includes a summer kitchen, spacious living areas with high vaulted ceilings, and a bonus room on the second floor. Imagine soaking up the summer sun on the stone patio, perfectly designed for beachside living. There is also potential for installing an in-ground pool on the premises, further elevating your outdoor oasis. Don’t miss your chance to own this piece of paradise on the North Fork and start living the dream today! 34
      Southold, NY 11939
      $1,949,000
      3 Bedrooms 3 Full Baths Sq. Ft. 2200.00:#
      Single Family For Sale ML# 3578605
      Welcome to 12910 Main Road, located in the heart of East Marion. This recently updated waterfront property boasts over 70 feet of pristine beachfront along Gardiners Bay, offering breathtaking panoramic water views and stunning sunrises to the southeast. The main house features a luxurious primary en suite bedroom on the second floor, complete with a private balcony, while the open kitchen and living area provide captivating water views from every angle. Enhancing this exceptional property is a charming, fully updated legal guest cottage, which includes a summer kitchen, spacious living areas with high vaulted ceilings, and a bonus room on the second floor. Imagine soaking up the summer sun on the stone patio, perfectly designed for beachside living. There is also potential for installing an in-ground pool on the premises, further elevating your outdoor oasis. Don’t miss your chance to own this piece of paradise on the North Fork and start living the dream today!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • 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
      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)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • 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
      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)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Wonderfully reimagined water view cottage in Goose Bay Estates beachfront community. Unique architectural details, hardwood floors, new carpet, and fresh paint enhance the charm of this home, with attention drawn to the beautiful landscaping and views. A large screened porch extends the living space, while the terraced patio includes a fire pit area and grilling nook for your entertaining pleasure. Mature plantings include a climbing hydrangea arbor, perennials and stately trees. The bonus features of an outdoor shower, shed, and enhanced heated garage add to the appeal of this coastal cutie. 31
      Southold, NY 11971
      $825,000
      2 Bedrooms 2 Full Baths Sq. Ft. 1000.00:#
      Single Family For Sale ML# 3558403
      Wonderfully reimagined water view cottage in Goose Bay Estates beachfront community. Unique architectural details, hardwood floors, new carpet, and fresh paint enhance the charm of this home, with attention drawn to the beautiful landscaping and views. A large screened porch extends the living space, while the terraced patio includes a fire pit area and grilling nook for your entertaining pleasure. Mature plantings include a climbing hydrangea arbor, perennials and stately trees. The bonus features of an outdoor shower, shed, and enhanced heated garage add to the appeal of this coastal cutie.
      Presented By: The Agency Northshore NY  631-870-0753
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
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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 Andrew Stype Realty Inc are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.

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    12985 Main Road, P.O. Box 63, Mattituck, NY 11952

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