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Southold Real Estate

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    • Welcome to a stunning, one-of-a-kind waterfront home in the highly sought-after hamlet of Southold. This custom, modern residence is perfectly situated on Town Creek, featuring 160 feet of waterfront and expansive views of Peconic Bay. It includes a private 6’ x 20’ floating dock connected by an 82’ Trex catwalk. Constructed with meticulous attention to detail, this home is built to last. It boasts high-end structural integrity, energy-efficient elements, and luxurious finishes throughout its sleek, open-concept design, encompassing approximately 4, 500 square feet of living space. The residence is flooded with natural light and showcases architectural features such as floor-to-ceiling windows, floating staircases, a bluestone-covered patio, and a walk-out lower terrace. The modern custom kitchen is adorned with ceiling-height cabinetry, luxury appliances, marble countertops, and porcelain inlays. The great room is anchored by a gas fireplace surrounded by textured porcelain. The upper-level primary suite includes a private balcony, while the main-floor junior suite offers private access to the backyard. The lower level adds 2, 000 square feet for the new owners to personalize, along with a bonus space on the top floor. The offering is complete with mature landscaping and the potential for a water-facing pool. This residence is located in the heart of the North Fork, with close access to Founders Landing Beach, wineries, farm-to-table dining, and the vibrant town atmosphere. 25
      Southold, NY 11971
      $9,275,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4400.00:# Square Feet
      Single Family For Sale NEW ML# 3587614
      Welcome to a stunning, one-of-a-kind waterfront home in the highly sought-after hamlet of Southold. This custom, modern residence is perfectly situated on Town Creek, featuring 160 feet of waterfront and expansive views of Peconic Bay. It includes a private 6’ x 20’ floating dock connected by an 82’ Trex catwalk. Constructed with meticulous attention to detail, this home is built to last. It boasts high-end structural integrity, energy-efficient elements, and luxurious finishes throughout its sleek, open-concept design, encompassing approximately 4, 500 square feet of living space. The residence is flooded with natural light and showcases architectural features such as floor-to-ceiling windows, floating staircases, a bluestone-covered patio, and a walk-out lower terrace. The modern custom kitchen is adorned with ceiling-height cabinetry, luxury appliances, marble countertops, and porcelain inlays. The great room is anchored by a gas fireplace surrounded by textured porcelain. The upper-level primary suite includes a private balcony, while the main-floor junior suite offers private access to the backyard. The lower level adds 2, 000 square feet for the new owners to personalize, along with a bonus space on the top floor. The offering is complete with mature landscaping and the potential for a water-facing pool. This residence is located in the heart of the North Fork, with close access to Founders Landing Beach, wineries, farm-to-table dining, and the vibrant town atmosphere.
      Presented By: Douglas Elliman Real Estate  631-288-6244
      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
    • 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
    • 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! 36
      Southold, NY 11971
      $3,600,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4240.00:# Square Feet
      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  631-848-7730
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Best of Both Worlds - Enjoy The Seclusion Of This 2 Acre Parcel, Yet Close To Town, Shopping, Beaches & Vineyards. Photos Shown Are From Identical House Recently Completed In Southold. Easy To Preview! 32
      Southold, NY 11971
      $2,995,000
      8 Bedrooms 7 Full Baths Sq. Ft. 5600.00:# Square Feet
      Single Family For Sale ML# 3569381
      Best of Both Worlds - Enjoy The Seclusion Of This 2 Acre Parcel, Yet Close To Town, Shopping, Beaches & Vineyards. Photos Shown Are From Identical House Recently Completed In Southold. Easy To Preview!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • This quintessential vintage farmhouse is the epitome of old-world charm meets modern sophistication! Sited on 1.5 acres of park-like property and lovingly renovated with thoughtful additions including a heated saltwater gunite pool, electric pool cover, pool house with an outdoor fireplace, outdoor kitchen with a Gaucho grill and sink, a separate office studio, 3 bedrooms and 3 bathrooms. Plenty of room for expansion and incredible lush landscape designed with each season in mind and tons of privacy. Southold Park District beach rights, A quarter mile to Horton’s Lighthouse beach, 1 mile to McCabe’s beach and a short stroll to downtown Southold! This is your sunshine on a cloudy day! 36
      Southold, NY 11971
      $2,450,000
      3 Bedrooms 3 Full Baths
      Single Family For Sale ML# 3556367
      This quintessential vintage farmhouse is the epitome of old-world charm meets modern sophistication! Sited on 1.5 acres of park-like property and lovingly renovated with thoughtful additions including a heated saltwater gunite pool, electric pool cover, pool house with an outdoor fireplace, outdoor kitchen with a Gaucho grill and sink, a separate office studio, 3 bedrooms and 3 bathrooms. Plenty of room for expansion and incredible lush landscape designed with each season in mind and tons of privacy. Southold Park District beach rights, A quarter mile to Horton’s Lighthouse beach, 1 mile to McCabe’s beach and a short stroll to downtown Southold! This is your sunshine on a cloudy day!
      Presented By: Corcoran  631-848-7730
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • This prime Southold property offers a fantastic opportunity for subdivision and development! Spanning over 4 acres, surrounded by development rights sold land and only half a mile to McCabes Beach, this idyllic North Fork property is ready to change hands, and this rare offering has incredible potential. Some ideas include subdividing the property and building another home on the back piece or updating and expanding the current residence to create a spectacular estate! The property includes a solid, well-built home from 1967 with a modernized kitchen and updated bathrooms (2020), oak wood floors throughout the first floor (under the carpets), Central Air Conditioning (on the first floor, but can be easily added to the second floor), generator, and a cozy living room with wood burning fireplace. The dining area has sliders to a large wood deck overlooking forever farm views. Other amenities include a two-car garage and a full, dry basement. The home is currently on well water with a filtration system, but public water in the street is available for hookup if desired. The roof was replaced about 10 years ago with 30-year shingles & the driveway was repaved within the last year. This property is not only well-maintained but also ready for your vision. Opportunities like this are rare, so don’t miss out! 28
      Southold, NY 11971
      $2,200,000
      4 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3584997
      This prime Southold property offers a fantastic opportunity for subdivision and development! Spanning over 4 acres, surrounded by development rights sold land and only half a mile to McCabes Beach, this idyllic North Fork property is ready to change hands, and this rare offering has incredible potential. Some ideas include subdividing the property and building another home on the back piece or updating and expanding the current residence to create a spectacular estate! The property includes a solid, well-built home from 1967 with a modernized kitchen and updated bathrooms (2020), oak wood floors throughout the first floor (under the carpets), Central Air Conditioning (on the first floor, but can be easily added to the second floor), generator, and a cozy living room with wood burning fireplace. The dining area has sliders to a large wood deck overlooking forever farm views. Other amenities include a two-car garage and a full, dry basement. The home is currently on well water with a filtration system, but public water in the street is available for hookup if desired. The roof was replaced about 10 years ago with 30-year shingles & the driveway was repaved within the last year. This property is not only well-maintained but also ready for your vision. Opportunities like this are rare, so don’t miss out!
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Discover your dream home in this turn key and meticulously maintained waterfront property situated on 1.25 sprawling acres. This home has been recently expanded and completely renovated throughout, all while preserving the unique charm of a scallop shack in the 1800’s and its 1930’s design. As you enter, you’ll be greeted by bright, airy spaces that highlight the home’s exquisite design and attention to detail. Large windows provide picturesque views of the surrounding gardens and waterfront. The spacious living areas are perfect for gatherings, while the well-appointed kitchen features custom cabinetry and enhanced amenities that any home chef would appreciate. The sunroom, newly built in 2021, provides an escape to a cozy atmosphere that can be enjoyed year round. New mudroom and stone patio also completed in 2021 as well. With an abundance of closets throughout this home, there is plenty of storage space available. The primary ensuite is a luxurious retreat that seamlessly combines comfort and elegance with the brand new primary bathroom as a standout feature newly completed in 2023. A private balcony off the primary invites you to unwind and soak in breathtaking views. Step outside to enjoy the lush gardens and expansive grounds, where you can relax amidst the vibrant flora or host summer barbecues on the spacious deck with an outdoor wood burning stone fireplace. The property also includes a private dock with bay access, allowing you to indulge in boating, fishing, or simply soaking in the stunning waterfront. In addition to its idyllic outdoor spaces, this home offers a garage that provides ample storage and additional recreational uses, making it ideal for those with hobbies or outdoor equipment. And there is plenty of room for a pool. The surrounding area also offers opportunities for golfing, cycling and exploring quaint shops and local eateries. Experience the ultimate in waterfront living in this Southold gem, where comfort and charm meet the beauty of nature! This home is meticulously maintained! 36
      Southold, NY 11971
      $1,999,000
      3 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3377.00:# Square Feet
      Single Family For Sale ML# 3573033
      Discover your dream home in this turn key and meticulously maintained waterfront property situated on 1.25 sprawling acres. This home has been recently expanded and completely renovated throughout, all while preserving the unique charm of a scallop shack in the 1800’s and its 1930’s design. As you enter, you’ll be greeted by bright, airy spaces that highlight the home’s exquisite design and attention to detail. Large windows provide picturesque views of the surrounding gardens and waterfront. The spacious living areas are perfect for gatherings, while the well-appointed kitchen features custom cabinetry and enhanced amenities that any home chef would appreciate. The sunroom, newly built in 2021, provides an escape to a cozy atmosphere that can be enjoyed year round. New mudroom and stone patio also completed in 2021 as well. With an abundance of closets throughout this home, there is plenty of storage space available. The primary ensuite is a luxurious retreat that seamlessly combines comfort and elegance with the brand new primary bathroom as a standout feature newly completed in 2023. A private balcony off the primary invites you to unwind and soak in breathtaking views. Step outside to enjoy the lush gardens and expansive grounds, where you can relax amidst the vibrant flora or host summer barbecues on the spacious deck with an outdoor wood burning stone fireplace. The property also includes a private dock with bay access, allowing you to indulge in boating, fishing, or simply soaking in the stunning waterfront. In addition to its idyllic outdoor spaces, this home offers a garage that provides ample storage and additional recreational uses, making it ideal for those with hobbies or outdoor equipment. And there is plenty of room for a pool. The surrounding area also offers opportunities for golfing, cycling and exploring quaint shops and local eateries. Experience the ultimate in waterfront living in this Southold gem, where comfort and charm meet the beauty of nature! This home is meticulously maintained!
      Presented By: Engel & Volkers North Fork  631-298-7953
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Located just a stone’s throw away from Kenney’s Beach, this 6 bedroom, 4 bath stately brick beauty was built in 2007 and sits on 2+ bucolic acres. This home is adorned with luxurious features including radiant heat throughout the kitchen and foyer, designer appliances, custom cabinetry and a lovely balcony located off of one of the bedrooms. There is a grand two-story entry, a spacious eat-in kitchen adjacent to the great room with a cozy wood-burning fireplace, plus a first floor bedroom. The paved rear yard, stone fire pit and new inground pool with built in sitting area and table are to name just a few attributes of this incredible home. Come and make it your own! 30
      Southold, NY 11971
      $1,985,000
      6 Bedrooms 4 Full Baths Sq. Ft. 4000.00:# Square Feet
      Single Family For Sale ML# 3577500
      Located just a stone’s throw away from Kenney’s Beach, this 6 bedroom, 4 bath stately brick beauty was built in 2007 and sits on 2+ bucolic acres. This home is adorned with luxurious features including radiant heat throughout the kitchen and foyer, designer appliances, custom cabinetry and a lovely balcony located off of one of the bedrooms. There is a grand two-story entry, a spacious eat-in kitchen adjacent to the great room with a cozy wood-burning fireplace, plus a first floor bedroom. The paved rear yard, stone fire pit and new inground pool with built in sitting area and table are to name just a few attributes of this incredible home. Come and make it your own!
      Presented By: Compass Greater NY LLC  516-672-1577
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    Showing 1 - 10 of 16 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 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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