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Southold Real Estate

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    • You remember the feeling on some Caribbean isle or on the cliff of a European town. Each morning when your head leaves the pillow you know you are on vacation. Much closer you can recreate that feeling with this very private, 5.7 acre waterfront, meadow-like parcel spanning 175’ along the North Fork’s Long Island Sound. SCHD permits now in place. Bring your building plans to obtain building permit from Town of Southold BD to construct a significant house, waterside pool & tennis court with the low bluff providing easy access to the beach & even purchase the contiguous 5.7 acre parcel creating an almost 12 acre compound with guest house which would provide 350’ of total waterfront. On clear evenings, go for dinner early as you might want to get back for some of the most beautiful sunsets anywhere, as the sun disappears somewhere into the Sound leaving the horizon a purplish haze. Best of all, you won’t need a passport, a pat down or a plane ticket. Just get in your car and head East. 11
      Southold, NY 11939
      $3,750,000
      Unimproved Land For Sale ML# 3566669
      You remember the feeling on some Caribbean isle or on the cliff of a European town. Each morning when your head leaves the pillow you know you are on vacation. Much closer you can recreate that feeling with this very private, 5.7 acre waterfront, meadow-like parcel spanning 175’ along the North Fork’s Long Island Sound. SCHD permits now in place. Bring your building plans to obtain building permit from Town of Southold BD to construct a significant house, waterside pool & tennis court with the low bluff providing easy access to the beach & even purchase the contiguous 5.7 acre parcel creating an almost 12 acre compound with guest house which would provide 350’ of total waterfront. On clear evenings, go for dinner early as you might want to get back for some of the most beautiful sunsets anywhere, as the sun disappears somewhere into the Sound leaving the horizon a purplish haze. Best of all, you won’t need a passport, a pat down or a plane ticket. Just get in your car and head East.
      Presented By: Corcoran  631-288-6900
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Located on a bucolic road, in the heart of wine country. This homestead has 2 acres of vines and incredible vineyard views, a large agricultural barn and is surrounded by development rights sold land. A true chef’s kitchen, 4 spacious bedrooms, 4 bathrooms, 2 half baths, 2 laundry rooms, large living room, and a gorgeous sunroom leading out to a spectacular 40’x25’ heated gunite pool with a slate patio and built-in BBQ, full basement with a wine cellar, and to top it all off, an incredible 8 car garage with an apartment that has a fireplace. You will never want to leave! 30
      Southold, NY 11935
      $3,750,000
      4 Bedrooms 4 Full Baths 2 Half Baths Sq. Ft. 5465.00:#
      Single Family For Sale ML# 3539723
      Located on a bucolic road, in the heart of wine country. This homestead has 2 acres of vines and incredible vineyard views, a large agricultural barn and is surrounded by development rights sold land. A true chef’s kitchen, 4 spacious bedrooms, 4 bathrooms, 2 half baths, 2 laundry rooms, large living room, and a gorgeous sunroom leading out to a spectacular 40’x25’ heated gunite pool with a slate patio and built-in BBQ, full basement with a wine cellar, and to top it all off, an incredible 8 car garage with an apartment that has a fireplace. You will never want to leave!
      Presented By: Corcoran  631-765-1300
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Introducing The Mayor’s House. Built in 1836 by Oliver Wiswall, this stately Greek Revival home sits perched upon a hillside just outside of Hudson, NY in the coveted Mt Merino neighborhood with legendary views up the Hudson River. Pulling into the tree lined driveway and turning to the West, it’s easy to see why this area inspired a generation of artists known as the Hudson River School of Painters, the first native school of painting in the United States. The solid brick home retains the grand feeling of its original prominence with dentil moldings, Doric & Ionic order columns and three stories of living space plus a full basement. The main floor boast high ceilings, beautiful restored moldings, 2 front sitting rooms with fireplaces and a large dining room. A striking 1980’s addition is connected to the rear of the house with a 20+ foot vaulted ceiling and features a modern kitchen, pantry area with laundry, casual dining, sitting area, and access to a stone patio to enjoy the jaw dropping views. Upstairs find a primary ensuite, additional bed and ensuite bath. A third floor provides two additional bedrooms, a third full bath and den. Wood floors, big windows, tons of natural light and views throughout. A recent renovation includes all new heating and cooling, new roof, new septic tank, new kitchen and baths, new landscaping and driveway, new fixtures and finishes. The property is just under 40 acres of open lawn surrounding the home and woods in the back. Located under 2 miles to Warren Street in Hudson, convenient to the Rip Van Winkle Bridge, Amtrak Train, Olana and many of the Hudson Valley’s most popular destinations. 34
      Southold, NY 12534
      $3,700,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 4505.00:#
      Single Family For Sale ML# H6332031
      Introducing The Mayor’s House. Built in 1836 by Oliver Wiswall, this stately Greek Revival home sits perched upon a hillside just outside of Hudson, NY in the coveted Mt Merino neighborhood with legendary views up the Hudson River. Pulling into the tree lined driveway and turning to the West, it’s easy to see why this area inspired a generation of artists known as the Hudson River School of Painters, the first native school of painting in the United States. The solid brick home retains the grand feeling of its original prominence with dentil moldings, Doric & Ionic order columns and three stories of living space plus a full basement. The main floor boast high ceilings, beautiful restored moldings, 2 front sitting rooms with fireplaces and a large dining room. A striking 1980’s addition is connected to the rear of the house with a 20+ foot vaulted ceiling and features a modern kitchen, pantry area with laundry, casual dining, sitting area, and access to a stone patio to enjoy the jaw dropping views. Upstairs find a primary ensuite, additional bed and ensuite bath. A third floor provides two additional bedrooms, a third full bath and den. Wood floors, big windows, tons of natural light and views throughout. A recent renovation includes all new heating and cooling, new roof, new septic tank, new kitchen and baths, new landscaping and driveway, new fixtures and finishes. The property is just under 40 acres of open lawn surrounding the home and woods in the back. Located under 2 miles to Warren Street in Hudson, convenient to the Rip Van Winkle Bridge, Amtrak Train, Olana and many of the Hudson Valley’s most popular destinations.
      Presented By: Rouse + Co Real Estate LLC  845-750-0196
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Down a graceful country road, on the North Fork of Long Island your dream retreat awaits. Spanning over 13 acres with 354 feet of waterfront on Arshamomaque Pond leading out to the Peconic Bay. There is a 20 x 40 gunite pool, a barn with horse stalls, should you choose or for use as an art barn! Plenty of room for tennis. Inside is an exceptional chef’s kitchen with a Wolf range, butler’s pantry and plenty of space to entertain guests, or snuggle up by the stone fireplace and your 3-season porch. There are two wings - one which has 3 ensuite bedrooms, including the primary suite. The other has a full kitchen, two bedrooms and 1 bathroom. This home also features a wine cellar and walkout basement. A property of this caliber does not come to market often in Southold. Make your dreams come true - let this be you! 37
      Southold, NY 11971
      $3,600,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4240.00:#
      Single Family For Sale ML# 3582528
      Down a graceful country road, on the North Fork of Long Island your dream retreat awaits. Spanning over 13 acres with 354 feet of waterfront on Arshamomaque Pond leading out to the Peconic Bay. There is a 20 x 40 gunite pool, a barn with horse stalls, should you choose or for use as an art barn! Plenty of room for tennis. Inside is an exceptional chef’s kitchen with a Wolf range, butler’s pantry and plenty of space to entertain guests, or snuggle up by the stone fireplace and your 3-season porch. There are two wings - one which has 3 ensuite bedrooms, including the primary suite. The other has a full kitchen, two bedrooms and 1 bathroom. This home also features a wine cellar and walkout basement. A property of this caliber does not come to market often in Southold. Make your dreams come true - let this be you!
      Presented By: Corcoran  631-765-1300
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Rarely does a farm of this size come on the market on Oregon Road. Successful grower of landscaping material as well as a very active seasonal Christmas Tree Farm business. All planted material is included in the sale of this property. 37.47 ac are DRS, 2.67ac are full rights land 6 barns located on the full rights parcel. There are two wells, one is a deep well and the second is for drip irrigation. 10
      Southold, NY 11935
      $3,500,000
      Unimproved Land For Sale ML# 3577688
      Rarely does a farm of this size come on the market on Oregon Road. Successful grower of landscaping material as well as a very active seasonal Christmas Tree Farm business. All planted material is included in the sale of this property. 37.47 ac are DRS, 2.67ac are full rights land 6 barns located on the full rights parcel. There are two wells, one is a deep well and the second is for drip irrigation.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      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
    • Escape to paradise at this stunning waterfront home nestled on 8.9 acres of land along West Creek, providing access to the beautiful Peconic Bay. This remarkable property offers deeded beach rights just steps away and is situated in a serene setting that is simply irresistible. With seven generously-sized bedrooms, each featuring its own private ensuite bathroom, there is plenty of space for relaxation and privacy. The culinary kitchen is a chef’s dream, boasting a spacious layout that is perfect for entertaining. In addition, the property features a 32-foot indoor pool, complete with an exhilarating water park slide and a soothing hot tub, ensuring year-round entertainment. Whether you’re taking a break from remote work or winding down after a long day, the porch with fireplace is the perfect spot to gather with friends and family, while enjoying the breathtaking views. Speaking of views, nearly every room in this home offers captivating waterviews, allowing you to fully immerse yourself in the natural splendor that surrounds you. Outdoor activities abound, with opportunities for golfing and tennis at the nearby country club, as well as swimming, fishing, and kayaking right from your own backyard. This property also presents an excellent opportunity for a bed and breakfast, with its spacious layout creating an inviting retreat for guests. Immerse yourself in the tranquility and natural beauty of this incredible waterfront home, and experience a lifestyle that seamlessly combines luxury, comfort, and the wonders of nature. This home also features an expansive great room, multiple fireplaces, a theatre room, a gym and has potential for an inground pool and pickleball court. Truly a gem of the North Fork! 31
      Southold, NY 11935
      $3,399,000
      7 Bedrooms 6 Full Baths 4 Half Baths
      Single Family For Sale ML# 3549432
      Escape to paradise at this stunning waterfront home nestled on 8.9 acres of land along West Creek, providing access to the beautiful Peconic Bay. This remarkable property offers deeded beach rights just steps away and is situated in a serene setting that is simply irresistible. With seven generously-sized bedrooms, each featuring its own private ensuite bathroom, there is plenty of space for relaxation and privacy. The culinary kitchen is a chef’s dream, boasting a spacious layout that is perfect for entertaining. In addition, the property features a 32-foot indoor pool, complete with an exhilarating water park slide and a soothing hot tub, ensuring year-round entertainment. Whether you’re taking a break from remote work or winding down after a long day, the porch with fireplace is the perfect spot to gather with friends and family, while enjoying the breathtaking views. Speaking of views, nearly every room in this home offers captivating waterviews, allowing you to fully immerse yourself in the natural splendor that surrounds you. Outdoor activities abound, with opportunities for golfing and tennis at the nearby country club, as well as swimming, fishing, and kayaking right from your own backyard. This property also presents an excellent opportunity for a bed and breakfast, with its spacious layout creating an inviting retreat for guests. Immerse yourself in the tranquility and natural beauty of this incredible waterfront home, and experience a lifestyle that seamlessly combines luxury, comfort, and the wonders of nature. This home also features an expansive great room, multiple fireplaces, a theatre room, a gym and has potential for an inground pool and pickleball court. Truly a gem of the North Fork!
      Presented By: Engel & Volkers North Fork  631-298-7953
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Experience the allure of this stunning custom-built modern shore house, completed in 2023 and nestled in sought-after Rock Cove Estates, just moments from Greenport Village. This extraordinary property has been meticulously designed to showcase unique architectural elements and a phenomenal floor plan that flows seamlessly, perfect for entertaining. Upon entering, you are welcomed by an inviting foyer that leads to a breathtaking Great Room, drenched in natural light from impressive floor-to-ceiling architectural windows. Step outside onto a sprawling stone patio that encircles a luxurious 16x40 heated gunite pool, lush green grass and mature landscaping.The thoughtfully designed kitchen is a chef’s dream, featuring a premium JenAire Rise Series appliance package, a wine fridge, carefully selected stone countertops, and custom-built cabinetry. The main level also offers three generously sized bedrooms, two full bathrooms, a laundry room, and a mudroom that connects to an attached one-car garage. Ascend to the second floor to discover an amazing game/media room, complete with a balcony and catwalk that overlooks the Great Room below. The catwalk leads to the private ensuite bedroom, which boasts soaring ceilings, an en-suite bathroom, a spacious walk-in closet, and a private balcony with peekaboo views of Long Island Sound. Finally, enjoy exclusive access to the pristine private beach of Rock Cove Estates, available only to the 23 homes within this prestigious community. This property is a true gem and an absolute must-see in person! 37
      Southold, NY 11944
      $3,395,000
      4 Bedrooms 3 Full Baths Sq. Ft. 3600.00:#
      Single Family For Sale ML# 3582641
      Experience the allure of this stunning custom-built modern shore house, completed in 2023 and nestled in sought-after Rock Cove Estates, just moments from Greenport Village. This extraordinary property has been meticulously designed to showcase unique architectural elements and a phenomenal floor plan that flows seamlessly, perfect for entertaining. Upon entering, you are welcomed by an inviting foyer that leads to a breathtaking Great Room, drenched in natural light from impressive floor-to-ceiling architectural windows. Step outside onto a sprawling stone patio that encircles a luxurious 16x40 heated gunite pool, lush green grass and mature landscaping.The thoughtfully designed kitchen is a chef’s dream, featuring a premium JenAire Rise Series appliance package, a wine fridge, carefully selected stone countertops, and custom-built cabinetry. The main level also offers three generously sized bedrooms, two full bathrooms, a laundry room, and a mudroom that connects to an attached one-car garage. Ascend to the second floor to discover an amazing game/media room, complete with a balcony and catwalk that overlooks the Great Room below. The catwalk leads to the private ensuite bedroom, which boasts soaring ceilings, an en-suite bathroom, a spacious walk-in closet, and a private balcony with peekaboo views of Long Island Sound. Finally, enjoy exclusive access to the pristine private beach of Rock Cove Estates, available only to the 23 homes within this prestigious community. This property is a true gem and an absolute must-see in person!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Welcome Home to your Oceanfront Paradise! Nestled along the sun-kissed shores of North Fork’s Orient Point, lies a haven cherished by one family for over two decades. Step into the warmth of tradition, where every sunset paints a new memory, and the rhythm of the waves serenades your soul. With spacious living areas, panoramic views, and direct access to the beach, this oceanfront home isn’t just a property; it’s a legacy of love, laughter, and endless summer days. As its next chapter unfolds, the owners hope it finds someone who will cherish it as much as they have, someone who will fill its rooms with their own dreams and memories. So, to the next custodian of this cherished home, It’s not just a property being offered but a piece of legacy, love and laughter waiting to be continued. Create your own story in this timeless retreat, where every day feels like a holiday. Where memories are made to last a lifetime. Features: One Owner. The offering presents a rare opportunity to acquire at a price point significantly below replacement cost. 6-BR, 4.5-Baths & Office Room. The High-Ceilinged, Unfinished Basement offers endless possibilities: Entertainment Zone, Game Room, Home Gym, Creative Studio, Golf Simulator, or Wine Cellar. Seller Financing Available. 37
      Southold, NY 11957
      $3,394,999
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 4000.00:#
      Single Family For Sale ML# H6303191
      Welcome Home to your Oceanfront Paradise! Nestled along the sun-kissed shores of North Fork’s Orient Point, lies a haven cherished by one family for over two decades. Step into the warmth of tradition, where every sunset paints a new memory, and the rhythm of the waves serenades your soul. With spacious living areas, panoramic views, and direct access to the beach, this oceanfront home isn’t just a property; it’s a legacy of love, laughter, and endless summer days. As its next chapter unfolds, the owners hope it finds someone who will cherish it as much as they have, someone who will fill its rooms with their own dreams and memories. So, to the next custodian of this cherished home, It’s not just a property being offered but a piece of legacy, love and laughter waiting to be continued. Create your own story in this timeless retreat, where every day feels like a holiday. Where memories are made to last a lifetime. Features: One Owner. The offering presents a rare opportunity to acquire at a price point significantly below replacement cost. 6-BR, 4.5-Baths & Office Room. The High-Ceilinged, Unfinished Basement offers endless possibilities: Entertainment Zone, Game Room, Home Gym, Creative Studio, Golf Simulator, or Wine Cellar. Seller Financing Available.
      Presented By: Keller Williams NYC  212-301-1140
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • A rare opportunity to acquire one of Orient’s oldest operating farms, held in the Terry family since 1730. The farmhouse was built by Marcus Terry in 1850 and operated as the Orient Point Post office until 1913. A large barn with loading dock and original outbuildings complete the offering. Development rights for 14.4 acres have been sold, with development rights intact for an additional 5 acres. There are sound beach rights. 27
      Southold, NY 11957
      $3,350,000
      3 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 2086.00:#
      Single Family For Sale ML# 3570534
      A rare opportunity to acquire one of Orient’s oldest operating farms, held in the Terry family since 1730. The farmhouse was built by Marcus Terry in 1850 and operated as the Orient Point Post office until 1913. A large barn with loading dock and original outbuildings complete the offering. Development rights for 14.4 acres have been sold, with development rights intact for an additional 5 acres. There are sound beach rights.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    Showing 21 - 30 of 379 results| view:  results per page« 1|2|3|4|5|...|last »
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    12985 Main Road, P.O. Box 63, Mattituck, NY 11952

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