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Southold Real Estate

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    Showing 1 - 10 of 55 results| view:  results per page« 1|2|3|4|5|...|last »
    • Discover the charm of waterfront living on this 8-acre estate along Southold Bay, boasting 157 feet of pristine shoreline and a private beach for tranquil retreats. The welcoming gates open to a driveway lined with pear trees, leading to a home that celebrates the beauty of its natural surroundings. The foyer unfolds into a living room illuminated by 24-foot windows, offering panoramic views of the bay and easy access to your secluded beach. The heart of the home, the kitchen, is ready for any culinary endeavor and seamlessly connects to the dining and living areas, ideal for casual entertaining. A guest suite on the ground floor provides a quiet escape for visitors. Upstairs holds four ensuite bedrooms, with two featuring balconies that invite the outside in, each morning graced by waterfront vistas. With over 6, 000 square feet, the home offers ample space while maintaining a cozy ambiance. Outdoor life is a breeze with a deck designed for relaxation and gatherings, against the backdrop of your own beachfront. Beyond the tranquility of your estate, downtown Southold beckons with its lively dining scene, shops, and wineries, blending coastal serenity with community vibrancy in this unique Southold bayfront home. 28
      Southold, NY 11971
      $7,750,000
      5 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 6162.00:# Square Feet
      Single Family For Sale ML# 3482756
      Discover the charm of waterfront living on this 8-acre estate along Southold Bay, boasting 157 feet of pristine shoreline and a private beach for tranquil retreats. The welcoming gates open to a driveway lined with pear trees, leading to a home that celebrates the beauty of its natural surroundings. The foyer unfolds into a living room illuminated by 24-foot windows, offering panoramic views of the bay and easy access to your secluded beach. The heart of the home, the kitchen, is ready for any culinary endeavor and seamlessly connects to the dining and living areas, ideal for casual entertaining. A guest suite on the ground floor provides a quiet escape for visitors. Upstairs holds four ensuite bedrooms, with two featuring balconies that invite the outside in, each morning graced by waterfront vistas. With over 6, 000 square feet, the home offers ample space while maintaining a cozy ambiance. Outdoor life is a breeze with a deck designed for relaxation and gatherings, against the backdrop of your own beachfront. Beyond the tranquility of your estate, downtown Southold beckons with its lively dining scene, shops, and wineries, blending coastal serenity with community vibrancy in this unique Southold bayfront home.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Attention Developers and Discerning Investors! Opportunity knocks with this 36-acre parcel, Development Rights in Tact, nestled in the heart of the North Fork. Ideally positioned along Arshamomack Creek with access to both County and Municipal roadways, this property offers a perfect setting for the development of either workforce housing, an exclusive residential enclave or a private estate. A generous tract of land within the R80 zone, allowing for 2-acre zoning. Close proximity to pristine beaches, renowned farmstands, and esteemed wineries. Bring your vision. (see attachments for more info.) 6
      Southold, NY 11971
      $4,495,000
      Unimproved Land For Sale ML# 3520399
      Attention Developers and Discerning Investors! Opportunity knocks with this 36-acre parcel, Development Rights in Tact, nestled in the heart of the North Fork. Ideally positioned along Arshamomack Creek with access to both County and Municipal roadways, this property offers a perfect setting for the development of either workforce housing, an exclusive residential enclave or a private estate. A generous tract of land within the R80 zone, allowing for 2-acre zoning. Close proximity to pristine beaches, renowned farmstands, and esteemed wineries. Bring your vision. (see attachments for more info.)
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story. 13
      Southold, NY 11971
      $4,300,000
      Unimproved Land For Sale ML# 3514107
      Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • **Luxurious Coastal Retreat in Southold’s Prestigious Deer Run** Nestled on a private, nearly 2-acre lot within the exclusive Deer Run community, this remarkable 5-bedroom, 9-bathroom cedar shake home epitomizes coastal luxury and refined living. Spanning an impressive 6, 000 square feet and surrounded by 37 acres of preserved land, this home is a haven of grandeur and comfort. Its thoughtful design features transom windows, coffered ceilings, paneled walls, and crown moldings. An open floor plan includes a gourmet kitchen with Carrera marble island, top-of-the-line appliances, and white cabinets with glass accents. The living room is anchored by a fieldstone fireplace with a driftwood mantle. French doors lead to a radiant-heated screened porch with its own wood-burning fireplace, ideal for seamless indoor-outdoor entertaining.The main floor master suite offers expansive walk-in closets and a marble bathroom. Upstairs, find four en-suite bedrooms, a bunk room, and a den. The lower level boasts a theater and a glass-enclosed gym. This property efficiently combines high-performance blow-in insulation with a dual water system, utilizing well water for a comprehensive 16-zone irrigation and municipal water for safe, in-home use. Outdoors, enjoy a 20x40 heated saltwater gunite pool with a waterfall jacuzzi, surrounded by a 1, 500 square foot bluestone patio, an outdoor fire pit, and a pergola. This property also features a lush lawn, a basketball/pickleball court, and proximity to Peconic Bay, beaches, and local wineries. Experience unparalleled luxury in this exquisite Southold home. 36
      Southold, NY 11971
      $3,950,000
      5 Bedrooms 5 Full Baths 4 Half Baths Sq. Ft. 6000.00:# Square Feet
      Single Family For Sale ML# 3544128
      **Luxurious Coastal Retreat in Southold’s Prestigious Deer Run** Nestled on a private, nearly 2-acre lot within the exclusive Deer Run community, this remarkable 5-bedroom, 9-bathroom cedar shake home epitomizes coastal luxury and refined living. Spanning an impressive 6, 000 square feet and surrounded by 37 acres of preserved land, this home is a haven of grandeur and comfort. Its thoughtful design features transom windows, coffered ceilings, paneled walls, and crown moldings. An open floor plan includes a gourmet kitchen with Carrera marble island, top-of-the-line appliances, and white cabinets with glass accents. The living room is anchored by a fieldstone fireplace with a driftwood mantle. French doors lead to a radiant-heated screened porch with its own wood-burning fireplace, ideal for seamless indoor-outdoor entertaining.The main floor master suite offers expansive walk-in closets and a marble bathroom. Upstairs, find four en-suite bedrooms, a bunk room, and a den. The lower level boasts a theater and a glass-enclosed gym. This property efficiently combines high-performance blow-in insulation with a dual water system, utilizing well water for a comprehensive 16-zone irrigation and municipal water for safe, in-home use. Outdoors, enjoy a 20x40 heated saltwater gunite pool with a waterfall jacuzzi, surrounded by a 1, 500 square foot bluestone patio, an outdoor fire pit, and a pergola. This property also features a lush lawn, a basketball/pickleball court, and proximity to Peconic Bay, beaches, and local wineries. Experience unparalleled luxury in this exquisite Southold home.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Boat slip in your backyard. This Bayview waterside estate sits on nearly 2.5 acres of secluded property in the coveted Shellfisher Preserve association comprised of three spectacular custom homes. Water views and 300 feet from your private deeded bay beach and your own 70’ long deep-water stationary dock in a private marina. Huge, detached 1, 800 sqft post-and-beam barn style garage. The property is flanked by a spectacular 650’ long deep water, tidal lagoon owned and maintained through the Peconic Land Trust. This traditional style home was custom built, ground up and features 3 bedrooms upstairs with large master suite, possible first floor bedroom or den. 3 car garage has finished studio space above with exquisite water views. Site plan with room for a 20x40 Gunite pool in the large grassy and level backyard which is fully deer fenced. 30
      Southold, NY 11971
      $3,895,000
      3 Bedrooms 3 Full Baths
      Single Family For Sale ML# 3546951
      Boat slip in your backyard. This Bayview waterside estate sits on nearly 2.5 acres of secluded property in the coveted Shellfisher Preserve association comprised of three spectacular custom homes. Water views and 300 feet from your private deeded bay beach and your own 70’ long deep-water stationary dock in a private marina. Huge, detached 1, 800 sqft post-and-beam barn style garage. The property is flanked by a spectacular 650’ long deep water, tidal lagoon owned and maintained through the Peconic Land Trust. This traditional style home was custom built, ground up and features 3 bedrooms upstairs with large master suite, possible first floor bedroom or den. 3 car garage has finished studio space above with exquisite water views. Site plan with room for a 20x40 Gunite pool in the large grassy and level backyard which is fully deer fenced.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      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 home awaits. Sprawling 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 this magical home is an exceptional chef’s kitchen with a Wolf range, butler’s pantry and plenty of entertaining space - including a generous fireplace and a 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 the market often on the North Fork of Long Island. Let’s make your dreams come true - this could be you!! 36
      Southold, NY 11971
      $3,600,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4500.00:# Square Feet
      Single Family For Sale ML# 3471355
      Down a graceful country road, on the North Fork of Long Island your dream home awaits. Sprawling 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 this magical home is an exceptional chef’s kitchen with a Wolf range, butler’s pantry and plenty of entertaining space - including a generous fireplace and a 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 the market often on the North Fork of Long Island. Let’s make your dreams come true - this could be you!!
      Presented By: Corcoran  631-765-1300
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Introducing one of the North Fork’s most iconic properties, seamlessly blending historical grandeur with contemporary living. Originally constructed circa 1915, this Georgian estate served as additional living quarters for the family of the former 40-acre waterfront Cosden estate. Today, this exceptional residence offers over 6000 square feet of luxurious living space featuring six bedrooms, all ensuite and is situated on a serene acre of land positioned across from a scenic preserve. An entertainer’s dream, the house welcomes guests with a magical courtyard entrance, setting the stage for epic gatherings with family and friends. Inside, soaring ceilings and abundant windows infuse the home with natural light, creating a bright and inviting atmosphere. A large great room features trayed ceilings, herringbone floors and a huge wood-burning fireplace, adding warmth and character to the space. The recently renovated chef’s kitchen is anchored by an oversized center-island with an enormous custom skylight above. A formal dining room with vaulted ceilings awaits holidays and dinner parties. A large playroom serves as a flex media room. The south-wing of the residence features the original stables with a secluded and private office just beyond. Additionally, a large temperature-controlled wine cellar in the basement caters to connoisseurs and collectors alike. Step outside to the park-like backyard, where a heated gunite pool awaits amidst mature specimen trees and ornamental plantings, offering a private retreat. An outdoor shower is designed to take in the beautiful gardens. A timeless East End investment in the heart of the North Fork. 34
      Southold, NY 11971
      $3,395,000
      6 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 6250.00:# Square Feet
      Single Family For Sale NEWOPEN HOUSE ML# 3550414
      Introducing one of the North Fork’s most iconic properties, seamlessly blending historical grandeur with contemporary living. Originally constructed circa 1915, this Georgian estate served as additional living quarters for the family of the former 40-acre waterfront Cosden estate. Today, this exceptional residence offers over 6000 square feet of luxurious living space featuring six bedrooms, all ensuite and is situated on a serene acre of land positioned across from a scenic preserve. An entertainer’s dream, the house welcomes guests with a magical courtyard entrance, setting the stage for epic gatherings with family and friends. Inside, soaring ceilings and abundant windows infuse the home with natural light, creating a bright and inviting atmosphere. A large great room features trayed ceilings, herringbone floors and a huge wood-burning fireplace, adding warmth and character to the space. The recently renovated chef’s kitchen is anchored by an oversized center-island with an enormous custom skylight above. A formal dining room with vaulted ceilings awaits holidays and dinner parties. A large playroom serves as a flex media room. The south-wing of the residence features the original stables with a secluded and private office just beyond. Additionally, a large temperature-controlled wine cellar in the basement caters to connoisseurs and collectors alike. Step outside to the park-like backyard, where a heated gunite pool awaits amidst mature specimen trees and ornamental plantings, offering a private retreat. An outdoor shower is designed to take in the beautiful gardens. A timeless East End investment in the heart of the North Fork.
      Presented By: Compass Greater NY LLC  516-330-6086
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
      Upcoming Open House View Location
      05/18/2024 - 05/18/2024 11:00AM - 1:00PM
    • Welcome to 630 Calves Neck Road! This new construction North Fork diamond boasts 4, 400 square feet of luxury with 4 en-suite bedrooms, 5.5 baths and a huge bonus room with skylights. Set on .75 acres and offering seamless architectural details, the meticulous craftsmanship is evident in a gorgeous EIK with center island, high end finishes including Wolf and Sub-zero appliances, marble and porcelain baths, radiant heat, and double washer/dryers. One sun-filled room flows into the next for the ultimate in comfort, convenience and modern day living. Each detail has been thoughtfully designed from the vaulted ceilings, built-ins, cabled railings and pantry, to a fully fenced heated salt water in-ground pool, first floor primary bedroom, gas fireplace, and gleaming hardwood floors. Close to marinas, beaches, boating, golf, shopping and world class restaurants, farms and vineyards. Don’t miss out on the opportunity to make it all yours! 36
      Southold, NY 11971
      $3,149,000
      4 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 4400.00:# Square Feet
      Single Family For Sale ML# 3537102
      Welcome to 630 Calves Neck Road! This new construction North Fork diamond boasts 4, 400 square feet of luxury with 4 en-suite bedrooms, 5.5 baths and a huge bonus room with skylights. Set on .75 acres and offering seamless architectural details, the meticulous craftsmanship is evident in a gorgeous EIK with center island, high end finishes including Wolf and Sub-zero appliances, marble and porcelain baths, radiant heat, and double washer/dryers. One sun-filled room flows into the next for the ultimate in comfort, convenience and modern day living. Each detail has been thoughtfully designed from the vaulted ceilings, built-ins, cabled railings and pantry, to a fully fenced heated salt water in-ground pool, first floor primary bedroom, gas fireplace, and gleaming hardwood floors. Close to marinas, beaches, boating, golf, shopping and world class restaurants, farms and vineyards. Don’t miss out on the opportunity to make it all yours!
      Presented By: Compass Greater NY LLC  516-319-3274
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Beautiful custom home located in the hamlet of Southold captures amazing views of the LI Sound. Architectural details include an open floor plan, floating staircase, private roof-top, mahogany decks with horizontal cable railings, and all custom European windows and doors. An expansive luxury kitchen, a chic water-view lounge, and a first-floor ensuite bedroom provide a sophisticated North Fork retreat. The exterior is board and baton mixed with cedar. The pool is 20 x 40 with room for a pool house or cabana. The full basement provides an additional 1500 sq ft that can be finished. Southold Town Beach is less than 0.5 miles, approximately 10 min walk. Close to all that the East End has to offer. Professional photos will be coming soon. 4
      Southold, NY 11971
      $2,995,000
      5 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Sale ML# 3538082
      Beautiful custom home located in the hamlet of Southold captures amazing views of the LI Sound. Architectural details include an open floor plan, floating staircase, private roof-top, mahogany decks with horizontal cable railings, and all custom European windows and doors. An expansive luxury kitchen, a chic water-view lounge, and a first-floor ensuite bedroom provide a sophisticated North Fork retreat. The exterior is board and baton mixed with cedar. The pool is 20 x 40 with room for a pool house or cabana. The full basement provides an additional 1500 sq ft that can be finished. Southold Town Beach is less than 0.5 miles, approximately 10 min walk. Close to all that the East End has to offer. Professional photos will be coming soon.
      Presented By: Douglas Elliman Real Estate  631-288-6244
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Southold, North Fork: Over 30 acres of active farmland planted with nearly 40, 000 blueberry bushes and approximately 10 acres of fallow, open farmland for expansion or other agricultural uses... well cared for farmhouse and barns on approximately 1.83 acres just up from Horton’s Lane Beaches/Horton’s Point on the LI Sound. Sublime setting just moments to village amenities. Pursue your agricultural desires today and establish your North Fork legacy. 10
      Southold, NY 11971
      $2,899,000
      Unimproved Land For Sale ML# 3470462
      Southold, North Fork: Over 30 acres of active farmland planted with nearly 40, 000 blueberry bushes and approximately 10 acres of fallow, open farmland for expansion or other agricultural uses... well cared for farmhouse and barns on approximately 1.83 acres just up from Horton’s Lane Beaches/Horton’s Point on the LI Sound. Sublime setting just moments to village amenities. Pursue your agricultural desires today and establish your North Fork legacy.
      Presented By: Town And Country Real Estate  631-298-0600
      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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