Southold, NY Real Estate & Homes for Sale

This is a beautiful new luxury home with water views of the Long Island Sound and adjacent to a picturesque golf course. The high-quality craftsmanship, elegant masonry features, and carefully considered amenities offer a blend of simplicity and luxury. The open floor plan, high ceilings, and custom European windows create a bright and welcoming space. A covered bluestone porch leads to a 16’x32’ heated pool overlooking the stunning vista. Nestled in the charming hamlet of East Marion, the Pebble Beach Farm community has a tree-lined entrance and a private beach on the Long Island Sound. The community also features tennis, bocce, and basketball courts. Enjoy breathtaking sunsets, farm-to-table dining, and nightlife, all easily accessible. Buyers can customize various features and make a la carte requests, subject to review for detail-oriented buyers.

540 The Greenway Southold, NY 11939

$2,495,000

6 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 5040.00:#

Single Family For Sale ML# 3580870

This is a beautiful new luxury home with water views of the Long Island Sound and adjacent to a picturesque golf course. The high-quality craftsmanship, elegant masonry features, and carefully considered amenities offer a blend of simplicity and luxury. The open floor plan, high ceilings, and custom European windows create a bright and welcoming space. A covered bluestone porch leads to a 16’x32’ heated pool overlooking the stunning vista. Nestled in the charming hamlet of East Marion, the Pebble Beach Farm community has a tree-lined entrance and a private beach on the Long Island Sound. The community also features tennis, bocce, and basketball courts. Enjoy breathtaking sunsets, farm-to-table dining, and nightlife, all easily accessible. Buyers can customize various features and make a la carte requests, subject to review for detail-oriented buyers.

Presented By: Douglas Elliman Real Estate 631-288-6244

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

Welcome to this exceptional waterfront oasis! This stunning 4 bedroom, 3 bathroom home is a true gem nestled along the water’s edge, offering unparalleled relaxation and breathtaking views. Step inside and be greeted by an abundance of natural light, illuminating the spacious open-concept living area. The chic design, with its stylish finishes, creates a warm and inviting atmosphere throughout with panoramic windows that showcase the picturesque waterfront scenery. The gourmet kitchen is a chef’s delight, equipped with top-of-the-line appliances, ample counter space, and custom cabinetry. Prepare culinary masterpieces while enjoying the tranquil water views, or simply gather around the large island for casual dining and lively conversations. As you make your way to the bedrooms, you’ll find four generously sized bedrooms, each offering a cozy haven for relaxation and rest. The primary suite is a true sanctuary, featuring its own private balcony overlooking the water, a spacious walk-in closet, and a luxurious en-suite bathroom adorned with premium fixtures and finishes. The highlight of this property is undoubtedly the heated waterside saltwater pool. Whether you’re hosting lively poolside gatherings or enjoying a serene evening dip, the pool area will undoubtedly become your favorite spot to create lasting memories. This waterfront paradise also has a deepwater dock and offers direct access to the water, making it perfect for water enthusiasts. Imagine launching your boat, kayak or paddleboard right from your backyard, or simply enjoying a leisurely boat ride to explore the nearby coves and beaches. Enjoy the tranquility and serenity of waterfront living, while still being just a short drive away from local amenities, restaurants, and entertainment options. Your dream waterfront retreat awaits!

37

900 Fox Hollow Rd Southold, NY 11952

$2,495,000

4 Bedrooms 3 Full Baths

Single Family For Sale ML# 3556934

Welcome to this exceptional waterfront oasis! This stunning 4 bedroom, 3 bathroom home is a true gem nestled along the water’s edge, offering unparalleled relaxation and breathtaking views. Step inside and be greeted by an abundance of natural light, illuminating the spacious open-concept living area. The chic design, with its stylish finishes, creates a warm and inviting atmosphere throughout with panoramic windows that showcase the picturesque waterfront scenery. The gourmet kitchen is a chef’s delight, equipped with top-of-the-line appliances, ample counter space, and custom cabinetry. Prepare culinary masterpieces while enjoying the tranquil water views, or simply gather around the large island for casual dining and lively conversations. As you make your way to the bedrooms, you’ll find four generously sized bedrooms, each offering a cozy haven for relaxation and rest. The primary suite is a true sanctuary, featuring its own private balcony overlooking the water, a spacious walk-in closet, and a luxurious en-suite bathroom adorned with premium fixtures and finishes. The highlight of this property is undoubtedly the heated waterside saltwater pool. Whether you’re hosting lively poolside gatherings or enjoying a serene evening dip, the pool area will undoubtedly become your favorite spot to create lasting memories. This waterfront paradise also has a deepwater dock and offers direct access to the water, making it perfect for water enthusiasts. Imagine launching your boat, kayak or paddleboard right from your backyard, or simply enjoying a leisurely boat ride to explore the nearby coves and beaches. Enjoy the tranquility and serenity of waterfront living, while still being just a short drive away from local amenities, restaurants, and entertainment options. Your dream waterfront retreat awaits!

Presented By: Engel & Volkers North Fork 631-298-7953

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

Welcome to your dream beach home nestled in a serene beach community on the North Fork! This newly constructed residence offers the perfect blend of modern comfort and coastal charm, presenting an ideal sanctuary for those seeking the quintessential beach lifestyle. Upon entering, you’ll be greeted by an inviting open floor plan, seamlessly connecting the living, dining, and kitchen areas, creating a spacious and airy ambiance perfect for both relaxing and entertaining. The main floor boasts a convenient mudroom/laundry area, providing easy access for one-level living convenience. With four bedrooms, with three of the bedrooms featuring its own attached bathroom, including one on the main floor, this home offers unparalleled comfort and privacy for all occupants. Whether hosting guests or enjoying personal retreats, everyone will appreciate the luxury and convenience of ensuite facilities. Step outside onto the covered porch, where summer dining awaits amidst the gentle sea breezes and tranquil views of the preserved land beyond the backyard. The fenced backyard, featuring a sparkling pool for refreshing dips on hot days and outdoor seating surrounding a cozy fire pit, ideal for gathering under the stars on summerl evenings. The sandy beach community adds to the allure, offering a park area complete with picnic tables, panoramic views of the water, and access to a sandy beach where summer breezes beckon for leisurely strolls along the shoreline. This property presents a rare opportunity to experience the best of North Fork beach living. Whether you’re seeking a seasonal retreat or year-round residence, this home promises a lifestyle of comfort, convenience, and coastal charm. Don’t miss your chance to make memories and create your own slice of paradise in this idyllic seaside haven.

32

700 Gin Lane Southold, NY 11971

$2,474,000

4 Bedrooms 3 Full Baths 1 Half Bath

Single Family For Sale ML# 3539656

Welcome to your dream beach home nestled in a serene beach community on the North Fork! This newly constructed residence offers the perfect blend of modern comfort and coastal charm, presenting an ideal sanctuary for those seeking the quintessential beach lifestyle. Upon entering, you’ll be greeted by an inviting open floor plan, seamlessly connecting the living, dining, and kitchen areas, creating a spacious and airy ambiance perfect for both relaxing and entertaining. The main floor boasts a convenient mudroom/laundry area, providing easy access for one-level living convenience. With four bedrooms, with three of the bedrooms featuring its own attached bathroom, including one on the main floor, this home offers unparalleled comfort and privacy for all occupants. Whether hosting guests or enjoying personal retreats, everyone will appreciate the luxury and convenience of ensuite facilities. Step outside onto the covered porch, where summer dining awaits amidst the gentle sea breezes and tranquil views of the preserved land beyond the backyard. The fenced backyard, featuring a sparkling pool for refreshing dips on hot days and outdoor seating surrounding a cozy fire pit, ideal for gathering under the stars on summerl evenings. The sandy beach community adds to the allure, offering a park area complete with picnic tables, panoramic views of the water, and access to a sandy beach where summer breezes beckon for leisurely strolls along the shoreline. This property presents a rare opportunity to experience the best of North Fork beach living. Whether you’re seeking a seasonal retreat or year-round residence, this home promises a lifestyle of comfort, convenience, and coastal charm. Don’t miss your chance to make memories and create your own slice of paradise in this idyllic seaside haven.

Presented By: Century 21 Albertson Realty 631-765-3800

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

37

800 Lighthouse Rd 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 631-765-1300

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

23

1625 Stars Rd Southold, NY 11939

$2,350,000

4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 4400.00:#

Single Family For Sale ML# 3590402

Just Completed, 100% Turnkey and Fully Furnished New Construction by Premier Builder with First and Second Floor Primary Bedroom Suites Located within East Marion’s Most Exclusive Multi-Million Dollar Development Enclave. Location, Location, Location...Just a Couple of Blocks from the Private Stars Road Beach! Imagine Spending the Holidays and Creating Memories for Years to Come in This Exquisite Estate Home Overflowing with Ultra-Luxury Finishes - Showcased in a Light-Filled Open Concept Design Perfect for Entertaining Family and Friends. The Expertly Crafted Floor Plan Spans Over 4, 400 Sq. Ft. Highlighted by Custom Double Cabinetry Imported from England, 2 Inch Mitered Edge Caesarstone Countertop Island, Artisan Black Staircase Railing Integration, Rare 9-inch-Wide Plank White Oak Flooring, Handcrafted and Expertly Milled Lifestyle Wall, Chef Grade Appliances in Artistic Gourmet Kitchen, Dipped Cedar Shake Siding and more!! The Massive Semi-Finished Lower Level Boasts 10 Ft. volume Ceilings, Chic Flooring, Hi-Hat Lighting, 3 Egress Windows, and an Outside Entrance. Expansive 1 Acre Property Features a 20x40 Heated Saltwater Pool, Spacious Sandstone Patio, Fully Fenced Yard w/Cedar Gates and Cedar Accents and Fully Sodded Front and Backyard w/Irrigation. Synergistic Expandable Smart Hub Easily and Remotely Controls Alarm, Doorbell Camera, and Temperature. Electric Vehicle Charging Station and Custom Navy Shiplap Mudroom Highlight the Oversized Garage. Every Detail and Luxury Infusion Were Thoughtfully Considered and Generously Awarded - Resulting in a Perfect Blend of Modern Design and Rustic Charm. Enjoy the Award-Winning Wineries, Restaurants, and Boutique Shops that the North Fork is Famous For. A Truly World Class Lifestyle Awaits!

Presented By: Aurora Property Group 631-629-6003

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

35

1350 Eugenes Rd Southold, NY 11935

$2,300,000

3 Bedrooms 3 Full Baths Sq. Ft. 1800.00:#

Single Family For Sale ML# 3583141

Discover the perfect blend of modern style and natural beauty in this renovated Contemporary creek front home. Relax by the heated gunite pool and hot tub, paddle on the creek from your own dock, and enjoy al fresco dining under the stars. Surrounded by mature landscaping on .73 acres, this waterfront home offers privacy and seclusion. Inside, you’ll discover a cozy wood-burning fireplace, an open floor plan, perfect for entertaining guests and a first floor guest bedroom. Upstairs, the two ensuite bedrooms offer a private retreat with waterside balconies, providing stunning views of the serene surroundings.

Presented By: Daniel Gale Sothebys Intl Rlty 631-477-0013

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

This extraordinary estate-like property offers a lifestyle of unparalleled grandeur and tranquility. Nestled on 1.06 acres backing up to preserved land, the property features a grand main house, a newly constructed separate cottage, multiple garages, and a stunning in-ground pool. The main house boasts 4 bedrooms, 2.5 baths, an office/flex room, and spacious living areas perfect for entertaining. A welcoming oversized wrap-around porch leads to a spacious interior with a cozy ambiance set with gas fireplaces. Upgraded features include central air, a french drain system, leaf filter gutters, an on-demand generator, security systems, in-ground irrigation, and porch sunshades. A full heated basement provides ample storage or potential for finishing. The attached 2.5-car garage is heated and cooled, and doubles as an entertainment area. For car enthusiasts, an additional detached garage provides even more storage or could be converted into a large pool house, also heated and cooled. The recently completed cottage offers a private retreat with a spacious bedroom, large ensuite bathroom, open-concept kitchen, living room with a fireplace, a front porch, full basement, and outdoor shower. The property’s centerpiece is a 20x40 in-ground saltwater pool, complete with a hot tub, blue glass fire pit, and outdoor shower. Enjoy peaceful relaxation or host unforgettable gatherings. Bay beach access. Marina around the corner. With local eateries, vineyards, parks, and shops right around the corner... this property truly embodies the essence of a true North Fork estate. Don’t miss this opportunity to experience the ultimate in grandeur living.

36

1125 Ole Jule Lane Southold, NY 11952

$2,299,999

5 Bedrooms 3 Full Baths 1 Half Bath

Single Family For Sale ML# 3579870

This extraordinary estate-like property offers a lifestyle of unparalleled grandeur and tranquility. Nestled on 1.06 acres backing up to preserved land, the property features a grand main house, a newly constructed separate cottage, multiple garages, and a stunning in-ground pool. The main house boasts 4 bedrooms, 2.5 baths, an office/flex room, and spacious living areas perfect for entertaining. A welcoming oversized wrap-around porch leads to a spacious interior with a cozy ambiance set with gas fireplaces. Upgraded features include central air, a french drain system, leaf filter gutters, an on-demand generator, security systems, in-ground irrigation, and porch sunshades. A full heated basement provides ample storage or potential for finishing. The attached 2.5-car garage is heated and cooled, and doubles as an entertainment area. For car enthusiasts, an additional detached garage provides even more storage or could be converted into a large pool house, also heated and cooled. The recently completed cottage offers a private retreat with a spacious bedroom, large ensuite bathroom, open-concept kitchen, living room with a fireplace, a front porch, full basement, and outdoor shower. The property’s centerpiece is a 20x40 in-ground saltwater pool, complete with a hot tub, blue glass fire pit, and outdoor shower. Enjoy peaceful relaxation or host unforgettable gatherings. Bay beach access. Marina around the corner. With local eateries, vineyards, parks, and shops right around the corner... this property truly embodies the essence of a true North Fork estate. Don’t miss this opportunity to experience the ultimate in grandeur living.

Presented By: Daniel Gale Sothebys Intl Rlty 631-298-4130

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

34

945 New Suffolk Avenue Southold, NY 11952

$2,295,000

4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3300.00:#

Single Family For Sale ML# 3569691

Captivating Old-World Colonial set on a generous 1.25 acres, complete with a guest cottage and a separate art studio. Retaining period details, the main home has been thoughtfully updated and features two wood-burning fireplaces, wood floors throughout, a living room and family room bathed in natural light, a dining room with exquisite wainscoting, and a brand-new chef’s kitchen. The second floor boasts charming guest rooms and a primary bedroom overlooking the sprawling backyard, complete with a walk-in closet and an updated ensuite bath. The attic, though unfinished, includes two separate rooms ideal for future expansion. The property offers complete privacy with impressive hedges, garden beds, and specimen trees. There’s ample space on the grounds for a pool or tennis court. Nearby to New Suffolk coveted bay beaches and 1 minute to Mattituck’s Love Lane. A unique North Fork offering that must be seen to be fully appreciated. Aerial photos to follow, Not in a fema flood zone.

Presented By: Compass Greater NY LLC 631-251-8644

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

29

6005 Hortons Lane 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) 765 5333, or Email: Beninati Associates Real Estate

27

4235 Camp Mineola Rd Southold, NY 11952

$2,200,000

4 Bedrooms 2 Full Baths Sq. Ft. 1845.00:#

Single Family For Sale ML# 3552341

A true coastal paradise where the line between home and horizon blurs into one breathtaking Bayfront panorama. Situated mere steps from the water’s edge, this 4-bed, 2-bath home offers an immersive waterfront experience with the sensation of being aboard a boat providing 180-degree water views that captivate the eye from every vantage point. Whether you’re lounging on the sun-drenched waterside deck or hosting a sunset soiree, the Bay serves as the perfect backdrop to your plans. Inside offers a spacious open floor plan of kitchen, living, and dining, with large windows and a sliding glass door that frame the water. Imagine waking up to the gentle sounds of the waves and opening your eyes to the blue waters as all the spacious bedrooms upstairs have their own beautiful view. Additionally, there’s a dry bar with several refrigeration spaces and an ice maker, a separate 1-car garage with an attached bonus room to provide ample storage and versatility for your needs, and an outdoor shower. Close to North Fork vineyards, farm stands, fine dining, Love Lane, Strong’s Marina, etc. For those who crave the ’coastal living’ life, this is it!

Presented By: Daniel Gale Sothebys Intl Rlty 631-477-0013

Call Today: (631) 765 5333, or Email: Beninati Associates Real Estate

Southold Homes for Sale

121 properties match your search;

Questions? Just Ask!

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Southold Homes for Sale

121 properties match your search;

121 with Multiple photos ; 26 with Virtual Tour ; 8 with Videos

Questions? Just Ask!