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Southold Homes for Sale

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    • 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
    • The Intelligent Choice For Those Who Value A Home Which Embodies Privacy, Luxury And Time Well Spent . Welcome Your Family And Friends Into This Very Tasteful Turnkey Oasis With Amenities Galore Including Professional Kitchen With Patio Service Window, Butler’s Pantry For Proper Wine And Coffee Service, And A Sumptuous Yard. They May Never Want To Leave! No Detail Has Been Spared In This Estate Setting Including A Huge Bunk Room For The Kids And Overflow Guests, Library, Pool, Hot Tub And Expansive Yard. Please Call To Schedule A Private Viewing. 29
      Southold, NY 11971
      $3,100,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 4051.00:# Square Feet
      Single Family For Sale ML# 3515679
      The Intelligent Choice For Those Who Value A Home Which Embodies Privacy, Luxury And Time Well Spent . Welcome Your Family And Friends Into This Very Tasteful Turnkey Oasis With Amenities Galore Including Professional Kitchen With Patio Service Window, Butler’s Pantry For Proper Wine And Coffee Service, And A Sumptuous Yard. They May Never Want To Leave! No Detail Has Been Spared In This Estate Setting Including A Huge Bunk Room For The Kids And Overflow Guests, Library, Pool, Hot Tub And Expansive Yard. Please Call To Schedule A Private Viewing.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Southold, North Fork: Inspirational rural living on a farm by the sea. Nearly 32 acres of land (29 acres in land preservation), abutting farms to the west that are also preserved and just moments to McCabe’s/Horton’s Lane beach. A truly special offering allowing you to pursue North Fork farm-country living and harvest nearly 22 acres of coastal blueberries presently in production on the site. The offering includes two parcels of land: 1.83 acres with a romantic 19th century, recently updated, farmhouse featuring ’rocking chair’ front porch, entry foyer, formal living room, dining room with large bay window, den/office, large eat-in kitchen, 3-season room, pantry and powder room PLUS upstairs, 4 bedrooms and full bath. Also included are several large barns, outbuildings and sheds. 29 acres are preserved in perpetuity and are farmed with over 40, 000 blueberry bushes each yielding pounds of berries in Summer. All of this is just moments to restaurants, shopping and wineries. 34
      Southold, NY 11971
      $2,899,000
      4 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 1900.00:# Square Feet
      Single Family For Sale ML# 3440241
      Southold, North Fork: Inspirational rural living on a farm by the sea. Nearly 32 acres of land (29 acres in land preservation), abutting farms to the west that are also preserved and just moments to McCabe’s/Horton’s Lane beach. A truly special offering allowing you to pursue North Fork farm-country living and harvest nearly 22 acres of coastal blueberries presently in production on the site. The offering includes two parcels of land: 1.83 acres with a romantic 19th century, recently updated, farmhouse featuring ’rocking chair’ front porch, entry foyer, formal living room, dining room with large bay window, den/office, large eat-in kitchen, 3-season room, pantry and powder room PLUS upstairs, 4 bedrooms and full bath. Also included are several large barns, outbuildings and sheds. 29 acres are preserved in perpetuity and are farmed with over 40, 000 blueberry bushes each yielding pounds of berries in Summer. All of this is just moments to restaurants, shopping and wineries.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Meticulously restored and maintained 19th C Italianate style residence, beautifully set on elevated 1.25-acre lot. Built around 1850 by Silas Horton and occupied by his descendants until the 1960’s. original wrap around porch, 17.5’ floor to ceiling windows, ornate Cupula, marble fireplace mantles, original wide floorboards, in-tact period moldings, trims, banisters, and doors. Large, updated kitchen and baths, wood burning fireplace, large walk-up attic. Rarely does a house of this vintage and quality become available. 22
      Southold, NY 11971
      $2,295,000
      4 Bedrooms 3 Full Baths Sq. Ft. 2662.00:# Square Feet
      Single Family For Sale ML# 3540463
      Meticulously restored and maintained 19th C Italianate style residence, beautifully set on elevated 1.25-acre lot. Built around 1850 by Silas Horton and occupied by his descendants until the 1960’s. original wrap around porch, 17.5’ floor to ceiling windows, ornate Cupula, marble fireplace mantles, original wide floorboards, in-tact period moldings, trims, banisters, and doors. Large, updated kitchen and baths, wood burning fireplace, large walk-up attic. Rarely does a house of this vintage and quality become available.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Custom Curated Creekfront Contemporary Privately Set in the Coveted Cedar Beach Park Associated Beach Community with Associated Private Bay Beach Access as well as Public Beach Access, Just Around the Corner. A Private Dock on Cedar Creek Grants Access Out to the Bay, Perfect for a Boston Whaler or the Like, and Great for a Kayak, Canoe, or Paddleboard. The Home and Property are Pristine and have been Meticulously Maintained and Cared for. A True Place of Refuge. Filled with Natural Light and Great Energy. The Entry Foyer is Bright and Open and Flows into the Open Concept Living Room, Dining Room, and Kitchen. Vaulted and Cathedral Ceilings in the Living and Dining. The Kitchen was Beautifully Remodeled in 2022 and Overlooks All with Ample Counter Space, High-End Stainless Appliances, and Wolf Gas Range for Cooking. Great for Entertaining. The Home Further Boasts 3 Bedrooms and 2.5 Baths with Primary Bedroom En-Suites on the First and Second Floors. Both Bedrooms have Sliding Door Access to the Exterior with a Private Balcony on the Second Floor. Picturesque Views from Every Point in the Home. Hardwood Flooring in Main Living Spaces. Anderson Windows and Sliding Doors, Central Air Throughout. Whole House Propane Generator. One Car Attached Garage with Tesla Plug-In. Simply Immaculate and Entirely Turn-Key. Make This Home Yours! 36
      Southold, NY 11971
      $1,825,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2000.00:# Square Feet
      Single Family For Sale NEWOPEN HOUSE ML# 3546245
      Custom Curated Creekfront Contemporary Privately Set in the Coveted Cedar Beach Park Associated Beach Community with Associated Private Bay Beach Access as well as Public Beach Access, Just Around the Corner. A Private Dock on Cedar Creek Grants Access Out to the Bay, Perfect for a Boston Whaler or the Like, and Great for a Kayak, Canoe, or Paddleboard. The Home and Property are Pristine and have been Meticulously Maintained and Cared for. A True Place of Refuge. Filled with Natural Light and Great Energy. The Entry Foyer is Bright and Open and Flows into the Open Concept Living Room, Dining Room, and Kitchen. Vaulted and Cathedral Ceilings in the Living and Dining. The Kitchen was Beautifully Remodeled in 2022 and Overlooks All with Ample Counter Space, High-End Stainless Appliances, and Wolf Gas Range for Cooking. Great for Entertaining. The Home Further Boasts 3 Bedrooms and 2.5 Baths with Primary Bedroom En-Suites on the First and Second Floors. Both Bedrooms have Sliding Door Access to the Exterior with a Private Balcony on the Second Floor. Picturesque Views from Every Point in the Home. Hardwood Flooring in Main Living Spaces. Anderson Windows and Sliding Doors, Central Air Throughout. Whole House Propane Generator. One Car Attached Garage with Tesla Plug-In. Simply Immaculate and Entirely Turn-Key. Make This Home Yours!
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
      Upcoming Open House View Location
      04/27/2024 - 04/27/2024 12:00PM - 2:00PM
      04/28/2024 - 04/28/2024 12:00PM - 2:00PM
    • Southold--Reydon Shores--Beautiful, charming, farmhouse invites you in. 3-bedroom, 2.5 bath home in sought after community of Reydon Shores with easy access to the Association Bay beach and Marina. First floor large primary en-suite bedroom, chef’s kitchen with top shelf stainless appliances including a Thermador cooktop and double oven. Radiant heat in Primary Bath and Kitchen. Closets beyond belief and hardwood floors throughout. Light, bright, and spacious with good flow. The kitchen opens to a great room and dining area Additional living space with a cozy wood burning fireplace. Upstairs-- two oversized guest bedrooms with hall bath and loft area. Immaculately updated and maintained, move-in ready. Doors open to the outdoor space including a large patio, trex deck, 2-car detached garage, and barn offering endless opportunities--workshop, studio, garden work area--let your imagination lead you. Level, landscaped shy half acre property. A perfect North Fork home waiting for you. 36
      Southold, NY 11971
      $1,385,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2492.00:# Square Feet
      Single Family For Sale ML# 3542205
      Southold--Reydon Shores--Beautiful, charming, farmhouse invites you in. 3-bedroom, 2.5 bath home in sought after community of Reydon Shores with easy access to the Association Bay beach and Marina. First floor large primary en-suite bedroom, chef’s kitchen with top shelf stainless appliances including a Thermador cooktop and double oven. Radiant heat in Primary Bath and Kitchen. Closets beyond belief and hardwood floors throughout. Light, bright, and spacious with good flow. The kitchen opens to a great room and dining area Additional living space with a cozy wood burning fireplace. Upstairs-- two oversized guest bedrooms with hall bath and loft area. Immaculately updated and maintained, move-in ready. Doors open to the outdoor space including a large patio, trex deck, 2-car detached garage, and barn offering endless opportunities--workshop, studio, garden work area--let your imagination lead you. Level, landscaped shy half acre property. A perfect North Fork home waiting for you.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • This 5 bedroom, 4 full bathroom home offers a truly luxurious living experience. The open concept design seamlessly connects the kitchen to the dining and living areas, creating a warm and inviting space for gatherings. Step outside and you’ll discover a true oasis. The inground pool invites you to cool off during hot summer days. The beautiful stone hardscape finishes add a touch of elegance and sophistication to the outdoor space, creating a serene atmosphere for outdoor entertaining. Set on a generous .92 acre lot, you’ll have plenty of space to enjoy outdoor activities, whether it’s gardening, playing sports, or simply taking a leisurely stroll. The well-manicured grounds provide a picturesque backdrop for the home. One of the unique features of this property is the accessory apartment with a separate entrance and a fully equipped kitchen. This additional living space offers flexibility and versatility, allowing for multigenerational living or a private guest suite. Close to beaches, wineries, town and restaurants! 23
      Southold, NY 11971
      $1,349,000
      5 Bedrooms 4 Full Baths
      Single Family For Sale ML# 3531156
      This 5 bedroom, 4 full bathroom home offers a truly luxurious living experience. The open concept design seamlessly connects the kitchen to the dining and living areas, creating a warm and inviting space for gatherings. Step outside and you’ll discover a true oasis. The inground pool invites you to cool off during hot summer days. The beautiful stone hardscape finishes add a touch of elegance and sophistication to the outdoor space, creating a serene atmosphere for outdoor entertaining. Set on a generous .92 acre lot, you’ll have plenty of space to enjoy outdoor activities, whether it’s gardening, playing sports, or simply taking a leisurely stroll. The well-manicured grounds provide a picturesque backdrop for the home. One of the unique features of this property is the accessory apartment with a separate entrance and a fully equipped kitchen. This additional living space offers flexibility and versatility, allowing for multigenerational living or a private guest suite. Close to beaches, wineries, town and restaurants!
      Presented By: Engel & Volkers North Fork  631-298-7953
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150. 34
      Southold, NY 11971
      $1,200,000
      6 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 3200.00:# Square Feet
      Single Family For Sale ML# 3509055
      Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its time to relax step outside onto the Patio or front porch for a perfect spot to sit with a cup of coffee to observe the serene nature filled yard or the pool. HOA Fee of $150.
      Presented By: Richmond Realty Corp  631-727-5500
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Southold-Reydon Shores-Inviting 3/4 acre landscaped property with specimen plantings is the backdrop for this spacious well-maintained ranch in the sought after waterfront community of Reydon Shores. Easy access to the Association Bay Beach and protected Marina. Plenty of room for family and guests to gather in the large living room with a wood burning fireplace and doors to the outside rear deck. Formal dining room, eat-in kitchen open to living room, and an additional sitting room. Two generous ensuite primary bedrooms. Additional guest bedroom and hall bathroom. Hardwood floors. The heated inground swimming pool catches the sun throughout the day and is surrounded by a paver patio. YOU can have a lot of fun here! A move-in ready North Fork home just waiting for you to enjoy. 34
      Southold, NY 11971
      $1,150,000
      3 Bedrooms 3 Full Baths Sq. Ft. 2492.00:# Square Feet
      Single Family For Sale NEW ML# 3544899
      Southold-Reydon Shores-Inviting 3/4 acre landscaped property with specimen plantings is the backdrop for this spacious well-maintained ranch in the sought after waterfront community of Reydon Shores. Easy access to the Association Bay Beach and protected Marina. Plenty of room for family and guests to gather in the large living room with a wood burning fireplace and doors to the outside rear deck. Formal dining room, eat-in kitchen open to living room, and an additional sitting room. Two generous ensuite primary bedrooms. Additional guest bedroom and hall bathroom. Hardwood floors. The heated inground swimming pool catches the sun throughout the day and is surrounded by a paver patio. YOU can have a lot of fun here! A move-in ready North Fork home just waiting for you to enjoy.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Expansive Colonial Style Home Nestled On A Shy 1/2 Acre In The Charming Village Of Southold. With Over 2100 Sq Ft Of Living Space, 4 Bedrooms And 3 Full Baths Including An Ensuite, This Home Offers Ample Space For Family And Guests. As You Step Inside You’ll Be Greeted By The Spacious Living Room, Eat In Kitchen With Breakfast Nook, And Family Room With Fireplace. The Excitement Doesn’t End There! Step Outside To Your Own Private Oasis. The 18x36 In Ground Pool Beckons You To Take A Refreshing Dip On Warm Summer Days, Lounge Poolside Or Enjoy Outdoor Dining With Friends And Family. Just Moments Away From Goose Creek Beach And The Village Where You Can Indulge In A Day Of Sun, Sand, Surf And Some Of The Finest Restaurants And Vineyards On The North Fork. Don’t Miss Out On This Incredible Opportunity To Own A Home With Room For Extended Family And Guests Along With An Abundance Of Activities At Your Fingertips. Schedule A Showing Today And Make This Dream Home Yours! 28
      Southold, NY 11971
      $999,999
      4 Bedrooms 3 Full Baths Sq. Ft. 2184.00:# Square Feet
      Single Family For Sale ML# 3492741
      Expansive Colonial Style Home Nestled On A Shy 1/2 Acre In The Charming Village Of Southold. With Over 2100 Sq Ft Of Living Space, 4 Bedrooms And 3 Full Baths Including An Ensuite, This Home Offers Ample Space For Family And Guests. As You Step Inside You’ll Be Greeted By The Spacious Living Room, Eat In Kitchen With Breakfast Nook, And Family Room With Fireplace. The Excitement Doesn’t End There! Step Outside To Your Own Private Oasis. The 18x36 In Ground Pool Beckons You To Take A Refreshing Dip On Warm Summer Days, Lounge Poolside Or Enjoy Outdoor Dining With Friends And Family. Just Moments Away From Goose Creek Beach And The Village Where You Can Indulge In A Day Of Sun, Sand, Surf And Some Of The Finest Restaurants And Vineyards On The North Fork. Don’t Miss Out On This Incredible Opportunity To Own A Home With Room For Extended Family And Guests Along With An Abundance Of Activities At Your Fingertips. Schedule A Showing Today And Make This Dream Home Yours!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
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