Southold Homes with Waterfront YN

Welcome to Southold, a hidden gem nestled in the heart of Suffolk County, New York. This charming town, located on the picturesque North Fork of Long Island, is renowned for its breathtaking waterfront views, vibrant vineyards, and rich maritime history. With its serene beaches and lush landscapes, Southold offers a tranquil escape from the hustle and bustle of city life, making it an ideal destination for both year-round residents and seasonal visitors.

One of the most alluring features of Southold is its stunning waterfront properties. Imagine waking up to the gentle sound of waves lapping against the shore, with panoramic views of the Long Island Sound right from your window. Homes with waterfront access in Southold provide not just a residence, but a lifestyle filled with outdoor adventures and relaxation. Whether you enjoy sailing, kayaking, or simply basking in the sun on your private beach, these properties offer a unique opportunity to immerse yourself in nature’s beauty.

Beyond the stunning homes, Southold boasts a vibrant community with a rich cultural scene. Explore local farmers' markets, indulge in fresh seafood at waterfront restaurants, or take a leisurely stroll through the charming downtown area, dotted with boutique shops and art galleries. With a strong sense of community and a wealth of recreational activities, Southold is more than just a place to live; it’s a place to thrive.

Discover the magic of Southold and find your dream waterfront home today—where every day feels like a vacation!

Newest Southold Homes with Waterfront YN

$2,650,000

4 Beds ⋅ 4 Baths ⋅ 1023134 MLS

This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany decks invite you to soak in those bay views, entertain friends, or just unwind with the coastal breeze. Effortless, elevated, and ready for summer. This is the one you've been waiting for. Near Cedar and Goose Creek beach, Sophie's Rest, tasting rooms, farm stands, vineyards, and all that the North Fork is known for!

195 Williamsburg Drive, Southold

$2,150,000

3 Beds ⋅ 3 Baths ⋅ 1022803 MLS

Perfectly sited on a protected inlet on West Lake, with direct access to the pristine waters of the Little Peconic Bay, this exceptional waterfront retreat embodies the effortless elegance of North Fork living. Thoughtfully designed to embrace its spectacular setting, the home is filled with natural light and showcases captivating water views from its principal living spaces. The main level offers an inviting open-concept design, where a gracious living room with a gas fireplace, elegant dining area, and beautifully appointed chef's kitchen with premium finishes flow seamlessly onto an expansive waterfront deck, creating an ideal setting for both intimate gatherings and grand-scale entertaining. A private staircase leads to the large dock, with room for multiple boats and a permitted kayak launch, offering immediate access to some of the East End's finest boating, sailing, and fishing. Above, the rooftop observation deck captures sweeping panoramic vistas across Little Peconic Bay, Robins Island, and the ever-changing coastal landscape beyond. The finished lower level encompasses an additional 1,675 square feet of living space and features a spacious family room, two bedrooms, a bathroom, another fireplace, a wine cellar, and walls of sliding glass doors that blur the line between indoors and out, inviting the waterfront into every moment. Complete with private beach access, this is more than a home-it is a rare opportunity to embrace an extraordinary waterfront lifestyle where sunrise boat-rides, paddles, afternoons on the bay, and unforgettable sunsets become part of everyday life.

2245 Little Peconic Bay Lane, Southold

$999,000

2 Beds ⋅ 1 Baths ⋅ 1017744 MLS

The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. This private community on Hashamomuck Pond offers 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy kayaking, paddleboarding, fishing, and swimming right out your back door. This is the lifestyle you have thought about, why not make it happen now!

136 Bayview Avenue, Southold

$2,899,000

4 Beds ⋅ 3 Baths ⋅ 1005049 MLS

Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed living space, plus a finished 1,166-square-foot lower level. Sun-drenched interiors showcase wide-plank wire-brushed white oak flooring, custom millwork and cabinetry, Restoration Hardware lighting, recessed lighting, and Sonos sound throughout both the home and outdoor entertaining spaces. Every room in the home captures stunning water views, creating a seamless connection to the surrounding waterfront setting. The spectacular gourmet kitchen is designed for both everyday living and entertaining, featuring a Sub-Zero refrigerator, Wolf gas cooktop and double ovens, quartz and Caesarstone countertops, oversized center island, Bosch and Fisher & Paykel dishwashers, and a stunning butler’s pantry accented with Cle Tile backsplash. The living room is equally impressive with a custom wood-burning fireplace, built-in cabinetry, and an elegant wet bar complete with Sub-Zero beverage refrigerator, wine refrigerator, ice machine, and designer finishes throughout. The fully finished lower level offers exceptional additional living space with a kitchenette, double egress windows, and Fujitsu mini-split system—ideal for guests, recreation, or extended entertaining. Upstairs, four spacious water-view bedrooms include a luxurious primary suite featuring cathedral planked ceilings, a handmade vintage wood mantel, private deck access, walk-in closet, and spa-inspired bath. Elegant lime-washed walls add warmth and character to every bathroom. Outdoor living is nothing short of extraordinary with expansive first and second floor decking, a rooftop deck with panoramic water views, premium IPE Brazilian hardwood decking, covered outdoor entertaining area with built-in heaters and ceiling fans, outdoor shower, wired railings, cedar shake siding, Andersen 400 Series windows and doors, and beautifully landscaped grounds surrounded by mature privacy hedges. A true boater’s paradise, the property accommodates a large boat and offers direct access to Peconic Bay, Shinnecock Bay, and nearby sandbars for boating, kayaking, paddleboarding, clamming, and enjoying the ultimate North Fork waterfront lifestyle.

405 Williamsburgh Drive, Southold

$6,550,000

5 Beds ⋅ 5 Baths ⋅ 999173 MLS

Set on a rare south-facing double lot with 200 feet of direct Peconic Bay frontage, a sandy beach, and a protected dock, this exceptional waterfront offering captures the essence of North Fork living. Perfectly positioned to enjoy all-day sunshine, refreshing southerly breezes, and breathtaking sunsets, the property sits at an ideal elevation that enhances the views while maintaining an effortless connection to the shoreline. The broad waterfront and truly usable beach invite days spent swimming, sunbathing, paddleboarding, or simply unwinding at the water's edge. Directly across the street, a separate waterfront parcel features a newly refurbished dock capable of accommodating a mid-twenty-foot boat, offering convenient access to Shelter Island, Sag Harbor, and the Hamptons. Designed to maximize its remarkable setting, the residence is bathed in natural light, with walls of glass and sweeping views that draw the outdoors into everyday life. Bright, inviting interiors and generously scaled gathering spaces create a relaxed coastal atmosphere equally suited for entertaining or quiet retreats. Outside, the waterside terrace provides an exceptional setting for summer barbecues, al fresco dining, and gathering with family and friends. As the day winds down, vibrant sunsets reflect across the bay, creating unforgettable evenings in one of the North Fork's most picturesque waterfront settings.

920 Cedar Point Drive E, Southold

$4,000,000

3 Beds ⋅ 4 Baths ⋅ 997738 MLS

Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property with meaningful upside. The existing three-bedroom, four-bath home offers a solid foundation for renovation or expansion, allowing a new owner to tailor the property to their vision. The grounds are equally compelling. A tennis court is already in place, and the oversized detached three-car garage adds flexibility for storage, studio space, or future accessory use, leaving ample room to site a pool. Centrally located with easy access to the North Fork’s vineyards, farm stands, restaurants, and marinas, the setting strikes a balance between privacy and convenience. Offerings with this combination of land, beach quality, and potential are increasingly rare, presenting a clear opportunity to create a premier waterfront compound.

1480 Old Wood Path, Southold

$1,199,999

3 Beds ⋅ 2 Baths ⋅ 991901 MLS

Welcome to this One-of-a-Kind 4-Bedroom, Custom Built Colonial, Beachfront Property, ideally located on the North Fork of Long Island along the Beautiful LONG ISLAND SOUND! True Meaning of LOCATION! This Spectacular Waterfront Home offers Breathtaking Panoramic Views, Direct Beach Access (Southold Beach), and the Perfect Blend of Privacy and Coastal Charm. Wake up to Stunning Sunrises and the Sound of Waves! This Beachfront Colonial Home also Features a Spacious 4th Bedroom on the 3rd Floor with Amazing Water Views! Hardwood Floors in all 3 Bedrooms! Two Full Bathrooms, inside you'll walk into the Livingroom with a Custom Granite Fireplace, A Formal Dining Room Surrounded by Water Views, And An Eat-in-Kitchen with a side door to the Wrap Around Deck Overlooking Southold Beach! High Hats Throughout, Brand New Boiler with 2 Heating Zones, 200 Amp Electric, Built on a Pile Foundation which includes a Stand-Up Crawl Space with Plenty of Storage and a Retaining Wall ! Visit the Many Wineries and Farms, Minutes away from the Historic Maritime Village of Greenport ! Experience True Beachfront Living in one of Long Island’s most sought-after locations, A Rare Opportunity to own an Exceptional Home where Every Day feels like a Getaway.

52755 Soundview Avenue, Southold

$1,445,000

3 Beds ⋅ 2 Baths ⋅ 975344 MLS

Boaters Dream! Located in Southold, this 3-bedroom, 2-bathroom canal-front home on Cory Creek offers a well-designed layout and direct access to the water. The creek leads out to the bay, and the property features a deep-water dock suitable for a variety of boating needs. Inside, the home offers an open-concept living, dining, and kitchen area with a comfortable, functional flow. The kitchen includes modern appliances and ample counter space. Large windows provide natural light and water views, with direct access to the rear deck. The outdoor space includes a spacious deck with room for seating and dining, along with a gas grill setup. The dock provides convenient access for boating, kayaking, and other activities. The home includes three bedrooms and two bathrooms, offering flexible space for a variety of living arrangements. Additional features include well-maintained interiors and updated elements throughout. Conveniently located near local wineries, restaurants, and shops, with access to all that the North Fork has to offer.

470 Windy Point Lane, Southold

$6,850,000

5 Beds ⋅ 5 Baths ⋅ 946886 MLS

Welcome to a stunning, one-of-a-kind, luxury modern waterfront home in the highly sought-after hamlet of Southold. This custom, newly constructed, residence is perfectly oriented West on Town Creek. Featuring 160’ of waterfront and expansive views of Peconic Bay, it includes a private 6 x 20' dock and an 82’ Trex catwalk. Constructed with every attention to detail, the home includes maximum structural integrity, energy efficiency and elevated finishes throughout. The sleek open-concept design encompasses approximately 4,500 square feet of living space. The light-filled residence showcases curated architectural features, ranging from floor-to-ceiling glass, floating staircases, bluestone and covered patio, water-view balcony, and a walk-out lower terrace. The Modern custom kitchen is adorned with ceiling-high cabinetry, Thermador appliances, marble countertops and porcelain inlay backsplash. The adjoining great room is anchored by a stunning gas fireplace surrounded by textured porcelain and this main level also includes an office, dining room and junior en-suite offering private access to the water and soon to be built saline heated pool. An upper level primary en-suite includes a private balcony and three additional spacious bedrooms, luxury baths, laundry and unfinished bonus space. The lower level offers 2,000 square feet for new owners to reimagine and personalize. The offering is complete with Founders Landing Beach, wineries, farm to table dining and a vibrant North Fork atmosphere.

1750 Hobart Road, Southold

$2,399,000

3 Beds ⋅ 2 Baths ⋅ 943087 MLS

Waterfront living designed for effortless coastal comfort. Ideally located just moments from one of Southold’s premier beaches, this updated 3-bedroom, 2-bath contemporary home offers open water views, beautiful sunrises and sunsets, and a seamless indoor–outdoor flow. The light-filled main level features a newly built modern kitchen that opens directly to the outdoor entertaining area, along with a waterside first-floor primary suite. Large windows invite the views in, creating a relaxed, airy atmosphere throughout the home. Outside, the property lives like a private shoreline retreat. Enjoy the new heated saltwater pool with automatic cover, an enclosed outdoor shower, and generous patio space perfect for lounging or hosting. The private dock provides more than just waterfront enjoyment—there’s direct boating access to Southold Bay and Peconic Bay, with easy routes to Greenport, Shelter Island, and even Sag Harbor for dining, marinas, and day trips. A turnkey waterfront residence that blends comfort, modern updates, spectacular views and the best of coastal living!!!

470 Goose Creek Lane, Southold

$2,495,000

3 Beds ⋅ 2 Baths ⋅ 932327 MLS

Wake up to endless views of the Peconic Bay — sunlight glimmering off the water, birds gliding over the nearby nature preserve, and the calm rhythm of the deep-water inlet just beyond your deck. This sweet beach cottage captures everything that makes summer on the North Fork unforgettable. With 3 comfortable bedrooms, 2 baths, and an open, easy-flow layout connecting the living, dining, kitchen, and entertainment nook, it’s made for barefoot mornings and breezy afternoons with friends. Step outside to a spacious wraparound deck and 130 feet of pristine waterfront — perfect for soaking in the sun, launching a kayak, or simply taking in the view. Secluded yet steps to the private sandy association beach, this is a rare slice of coastal paradise where summer never really ends.

1455 Cedar Point Drive, Southold

$3,695,000

6 Beds ⋅ 4 Baths ⋅ 928708 MLS

Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6-bedroom, 4-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential. The enormous attic, featuring 8.5+ ft ceilings, offers the possibility of a third-floor buildout. The walk-out basement, with 9+ ft ceilings, two egresses, and plumbing in place, adds even more room for customization. Resort-style amenities continue across the grounds: a 16' x 32' heated saltwater gunite pool with electric cover is set into a 2,100 SF deck, a high-end 6-person hot tub and an outdoor shower. A wide path leads to a fire pit area and the private dock, which previously accommodated a 23' Grady-White and provides direct access to the bay. Inside, a chef’s kitchen, wood-burning fireplace, and generous ceiling heights enhance the home’s warm yet refined ambience. Radiant heat warms the eat-in kitchen, all bathrooms, and additional spaces throughout. Recent upgrades include the new pool and hot tub, a newly constructed circular driveway, freshly painted Hardie board siding, all-new interior paint, updated lighting, and modern hardware. A truly exceptional offering of space, serenity, and waterfront luxury—ideal as a full-time residence or a memorable seasonal escape.

105 Waterview Drive, Southold

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.