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Southold Real Estate

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    Showing 231 - 240 of 378 results| view:  results per page« first|...|22|23|24|25|...|last »
    • Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner may consider a year-round rental - inquire. Rental Permit# 1216. 27
      Southold, NY 11971
      $30,000
      2 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3588931
      Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner may consider a year-round rental - inquire. Rental Permit# 1216.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Bucolic, airy, and steps from Orient’s Village lane and beaches. Perfect location. Revel in 2605 Orchard Street, Orient’s grandeur and comfort, set against 15 acres of open meadows with stunning 180 degree tranquil views. This light and bright large home has everything you need to have an idyllic stay in the country. Once inside you can relax into a well appointed beautifully decorated and spacious layout with four bedrooms, all ensuite, eat-in kitchen, a formal dining room, front living room with fireplace and back parlor overlooking garden and pool area, and a large den with fireplace next to kitchen. Outside features a large fenced yard with bluestone area and gardens, specimen trees, a large Patio for gathering and al fresco dining, with an independently fenced in-ground heated pool offers fun and relaxation with views extending over 15 acres of expansive meadows beyond. Rental Permit# 1124 62
      Southold, NY 11957
      $30,000
      4 Bedrooms 5 Full Baths Sq. Ft. 4000.00:#
      Single Family For Sale ML# 3554090
      Bucolic, airy, and steps from Orient’s Village lane and beaches. Perfect location. Revel in 2605 Orchard Street, Orient’s grandeur and comfort, set against 15 acres of open meadows with stunning 180 degree tranquil views. This light and bright large home has everything you need to have an idyllic stay in the country. Once inside you can relax into a well appointed beautifully decorated and spacious layout with four bedrooms, all ensuite, eat-in kitchen, a formal dining room, front living room with fireplace and back parlor overlooking garden and pool area, and a large den with fireplace next to kitchen. Outside features a large fenced yard with bluestone area and gardens, specimen trees, a large Patio for gathering and al fresco dining, with an independently fenced in-ground heated pool offers fun and relaxation with views extending over 15 acres of expansive meadows beyond. Rental Permit# 1124
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Introducing your perfect summer retreat for 2025! This stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don’t miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085. 64
      Southold, NY 11971
      $30,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Misc For Sale ML# 3546491
      Introducing your perfect summer retreat for 2025! This stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don’t miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • New to Market FLEET’s NECK Rental! Walk to Beach from your Private FABULOUS SUMMER OASIS. 4 Bedroom and 2 Full Bath Contemporary Home on tucked away Lot Set Well-Back from Road on 1 + acres. Offers Sleek Main Floor Living Area with Fireplace, Chandeliered Dining Area, Foyer, Light Bright Kitchen with All Stainless-Steel Appliances, that leads to a Furnished 2-Level Deck with Both Living and Dining/BBQ Spaces, 2 Spacious Bedrooms and a Full Bath with Walk-In Shower. Lower level has 2 Additional Bedrooms and a Large Full Bath with Separate Living/Entertaining/Gaming Area for more Informal Fun! Air Hockey, FOOSBALL, & Large Flat Screen TV! Two-Car Garage and Plenty of Guest Parking. Bedrooms provide own TVs and plenty of closet space. PLUS: Fenced-in Sprawling Summertime Fun & Relaxation Spot. 20x40 Heated, Lighted, Saltwater Pool, with 4 In-Pool Chaise Loungers, and steps to separate Jacuzzi Spa to warm up before you Cool Down. Also enclosed is an Outdoor BBQ Pavillion with Bar Area and Kitchenette, as well as Outdoor Living Room complete with Wide Screen TV, and outdoor lighting. Live Your Best Life Here or walk a short distance to Bay Beach at End of Street, or a Short Drive to Long Island Sound and Ocean Beaches, and Local Marinas. Nearby to Gourmet Restaurants, Wineries, Breweries, Golf, Shopping, and NF Farm Stands & Easy Access to the LIRR or NYC Jitney. 3rd Story Master Suite and Attic Off-Limits to Tenants. Utilities Not included in Rental Amounts. Landlord takes care of Pool and Lawn; Tenants to Reimburse for Utilities for the Term; One Month Security Deposit and Utility Deposit (50% of Estimated Term) Lease and Proof of Renters Insurance Required and Satisfactory Credit Approval. 31
      Southold, NY 11935
      $30,000
      4 Bedrooms 2 Full Baths Sq. Ft. 2400.00:#
      Single Family For Sale ML# 3477027
      New to Market FLEET’s NECK Rental! Walk to Beach from your Private FABULOUS SUMMER OASIS. 4 Bedroom and 2 Full Bath Contemporary Home on tucked away Lot Set Well-Back from Road on 1 + acres. Offers Sleek Main Floor Living Area with Fireplace, Chandeliered Dining Area, Foyer, Light Bright Kitchen with All Stainless-Steel Appliances, that leads to a Furnished 2-Level Deck with Both Living and Dining/BBQ Spaces, 2 Spacious Bedrooms and a Full Bath with Walk-In Shower. Lower level has 2 Additional Bedrooms and a Large Full Bath with Separate Living/Entertaining/Gaming Area for more Informal Fun! Air Hockey, FOOSBALL, & Large Flat Screen TV! Two-Car Garage and Plenty of Guest Parking. Bedrooms provide own TVs and plenty of closet space. PLUS: Fenced-in Sprawling Summertime Fun & Relaxation Spot. 20x40 Heated, Lighted, Saltwater Pool, with 4 In-Pool Chaise Loungers, and steps to separate Jacuzzi Spa to warm up before you Cool Down. Also enclosed is an Outdoor BBQ Pavillion with Bar Area and Kitchenette, as well as Outdoor Living Room complete with Wide Screen TV, and outdoor lighting. Live Your Best Life Here or walk a short distance to Bay Beach at End of Street, or a Short Drive to Long Island Sound and Ocean Beaches, and Local Marinas. Nearby to Gourmet Restaurants, Wineries, Breweries, Golf, Shopping, and NF Farm Stands & Easy Access to the LIRR or NYC Jitney. 3rd Story Master Suite and Attic Off-Limits to Tenants. Utilities Not included in Rental Amounts. Landlord takes care of Pool and Lawn; Tenants to Reimburse for Utilities for the Term; One Month Security Deposit and Utility Deposit (50% of Estimated Term) Lease and Proof of Renters Insurance Required and Satisfactory Credit Approval.
      Presented By: Fedun Real Estate Inc  631-722-5000
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep. 12
      Southold, NY 11971
      $30,000
      3 Bedrooms 2 Full Baths Sq. Ft. 2000.00:#
      Single Family For Sale ML# 3236473
      Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep.
      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: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a fireplace, a formal dining room, a den, a large kitchen, and a pantry. Upstairs, there are five bedrooms, three baths, PLUS, an outdoor shower convenient for all to enjoy. The outbuilding, known as The Birdhouse, offers dormitory space for overflow guests with a private bathroom. The estate has a direct beachfront setting, with sugar sand and carefree days awaiting visitors in an old-fashioned East End seaside cottage. Permit# 0996 33
      Southold, NY 11971
      $30,000
      6 Bedrooms 4 Full Baths
      Single Family For Sale ML# 3212687
      Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a fireplace, a formal dining room, a den, a large kitchen, and a pantry. Upstairs, there are five bedrooms, three baths, PLUS, an outdoor shower convenient for all to enjoy. The outbuilding, known as The Birdhouse, offers dormitory space for overflow guests with a private bathroom. The estate has a direct beachfront setting, with sugar sand and carefree days awaiting visitors in an old-fashioned East End seaside cottage. Permit# 0996
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living Spaces. Its Picturesque Waterfront Setting Serving As A Constant Reminder Of The Beauty That Surrounds You. Here, You Can Start Your Day With A Refreshing Morning Jog, Entertain Guests With A Backyard Barbecue, Or Unwind With A Glass Of Wine While Watching The Sunset Over The Water. 1100 Pine Ave Is More Than Just An Address; It’s The Perfect Summer Getaway. Call Today To Schedule Your Private Tour. 37
      Southold, NY 11971
      $28,000
      3 Bedrooms 2 Full Baths
      Single Family For Sale ML# 3532447
      Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living Spaces. Its Picturesque Waterfront Setting Serving As A Constant Reminder Of The Beauty That Surrounds You. Here, You Can Start Your Day With A Refreshing Morning Jog, Entertain Guests With A Backyard Barbecue, Or Unwind With A Glass Of Wine While Watching The Sunset Over The Water. 1100 Pine Ave Is More Than Just An Address; It’s The Perfect Summer Getaway. Call Today To Schedule Your Private Tour.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Escape to your own piece of paradise in this stunning bayfront home, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or heading down to the beach to dip your toes in the sand. This home is a true oasis, perfect for outdoor entertaining and water activities. Whether you’re swimming, kayaking, paddleboarding, or simply lounging on the giant anchored raft, there’s something for everyone. The lush, hydrangea-filled gardens provide a sense of privacy and serenity, making this retreat incredibly enticing. With two spacious living areas and options for dining indoors or out, this home is designed for both relaxation and entertainment. Enjoy cozy evenings by the beach or star gazing, roasting marshmallows over a fire and making memories to last a lifetime. Discover the perfect North Fork getaway, where charm, character, and coastal living come together in harmony. 55
      Southold, NY 11948
      $25,000
      4 Bedrooms 2 Full Baths 1 Half Bath
      Misc For Sale ML# 3575176
      Escape to your own piece of paradise in this stunning bayfront home, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or heading down to the beach to dip your toes in the sand. This home is a true oasis, perfect for outdoor entertaining and water activities. Whether you’re swimming, kayaking, paddleboarding, or simply lounging on the giant anchored raft, there’s something for everyone. The lush, hydrangea-filled gardens provide a sense of privacy and serenity, making this retreat incredibly enticing. With two spacious living areas and options for dining indoors or out, this home is designed for both relaxation and entertainment. Enjoy cozy evenings by the beach or star gazing, roasting marshmallows over a fire and making memories to last a lifetime. Discover the perfect North Fork getaway, where charm, character, and coastal living come together in harmony.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-298-4130
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • Very spacious, sunlight filled custom built beauty just 3 minutes to gorgeous LI Sound beach. 44’ x 24’ heated, saltwater pool. Open concept LR/DR/KI with sliders to expansive deck overlooking private, fully fenced, park-like yard and pool area. Upstairs has a large, 2nd living room with billiards, foosball, tv area & sliders to another deck. 2 primary bedrooms - one on each level. 2nd floor primary has living room, wet bar, refrigerator and wall of sliders to deck. Home impeccably maintained and tastefully furnished throughout. Fine dining & state park just down the road. A scenic 9 mile drive to bustling downtown Greenport. Rental Permit #1117. Exp. 5.6.26. 60
      Southold, NY 11957
      $25,000
      4 Bedrooms 3 Full Baths Sq. Ft. 4000.00:#
      Misc For Sale ML# 3550345
      Very spacious, sunlight filled custom built beauty just 3 minutes to gorgeous LI Sound beach. 44’ x 24’ heated, saltwater pool. Open concept LR/DR/KI with sliders to expansive deck overlooking private, fully fenced, park-like yard and pool area. Upstairs has a large, 2nd living room with billiards, foosball, tv area & sliders to another deck. 2 primary bedrooms - one on each level. 2nd floor primary has living room, wet bar, refrigerator and wall of sliders to deck. Home impeccably maintained and tastefully furnished throughout. Fine dining & state park just down the road. A scenic 9 mile drive to bustling downtown Greenport. Rental Permit #1117. Exp. 5.6.26.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
    • ’ ONLY September onwards is available --- If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025. 55
      Southold, NY 11971
      $25,000
      4 Bedrooms 4 Full Baths
      Single Family For Sale ML# 3528933
      ’ ONLY September onwards is available --- If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025.
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631)298-8760, (631)298-8760, or  Email: Andrew Stype Realty Inc
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    12985 Main Road, P.O. Box 63, Mattituck, NY 11952

    Office: (631)298-8760

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