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

$1,999,999

3 Beds ⋅ 3 Baths ⋅ 1022803 MLS

Rarely does a Southold waterfront property offer such a compelling combination of privacy, direct bay access, and expansive water views. Set on a protected inlet with a permitted dock and kayak launch, this three-bedroom, three-bath home is designed around its extraordinary setting. Sun-filled rooms open to a supersized waterfront deck, with a chef's kitchen with soapstone counters, a welcoming living room with fireplace, and water views throughout. The first-floor primary suite is a quiet retreat, and a rooftop observation deck captures sweeping vistas across Little Peconic Bay. The permitted lower level adds two bedrooms, a bath, a den, a second fireplace, and a wine cellar, with sliding doors opening to the water. The next owner also inherits a head start. The sellers have applied for a pool permit, so approvals are already in motion, and they have applied for a Grant toward a new IA septic system that transfers with the property. Approximately 3,900 square feet of finished living space on a half-acre, plus a one-car garage and shed, in a truly special Southold waterfront setting.

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. Located on a dead-end street on Hashamomuck Pond, this home offers a private dock, 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy boating, kayaking, paddleboarding, fishing, and swimming right out your back door. Surrounded by the gorgeous Southold beaches, over 40 wineries, and local farms, the North Fork has it all. Make it a vacation or year-round home, 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

$5,995,000

5 Beds ⋅ 5 Baths ⋅ 999173 MLS

Welcome to 920 Cedar Point E in Southold, a spectacular 1.4-acre waterfront estate overlooking one of the most breathtaking stretches of the Peconic Bay, complete with a private deeded dock slip just steps from the property. Featuring 200 feet of pristine sugar-sand beachfront, this exceptional setting offers privacy, serenity, all-day sunshine, and the gentle prevailing southwest breezes for which the Peconic Bay is known. As day turns to evening, breathtaking sunsets create an ever-changing display of color across the water before giving way to a starlit night sky. Designed to complement its remarkable surroundings, the cedar-shake residence stretches across the property's 200 feet of waterfront, positioned remarkably close to the Bay while protectively perched approximately 25 feet above sea level. From nearly every vantage point, the home offers a front-row seat to a uniquely nautical backdrop of passing boats, maritime activity, and local wildlife. Inside, the approximately 3,500-square-foot, five-bedroom, four-and-a-half-bath home is light and airy, with wide-plank wood floors and generously scaled living spaces. A more recently added Great Room features soaring, sun-soaked ceilings and is anchored by an oversized fireplace, creating an inviting gathering space with a strong connection to the surrounding landscape. The primary suite is truly one of a kind, extending even closer toward the water's edge and capturing panoramic Bay views from nearly every angle. The spa-like en-suite bathroom is equally captivating, perfectly framed by an ever-changing canvas of sea and sky. Outside, the grounds are meticulously landscaped with mature plantings, sprawling lawns, and specimen trees that create an exceptional sense of privacy. There is ample room for an in-ground pool in multiple locations, as well as significant opportunity for future expansion of the existing residence should additional space be desired. For those seeking that quintessential beachfront North Fork home without sacrificing the convenience of boating on the Peconic Bay, 920 Cedar Point E represents a truly exceptional offering.

920 Cedar Point Drive E, Southold

$3,695,000

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

$1,149,999

3 Beds ⋅ 2 Baths ⋅ 991901 MLS

Welcome to this One-of-a-Kind 3-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

$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

$1,425,000

3 Beds ⋅ 4 Baths ⋅ 924424 MLS

Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, located in the prestigious Willow Point community. With panoramic water views, a private dock, and access to a secluded beach, this property combines timeless coastal charm with modern luxury. Buyers can choose from two exclusive paths to own this exceptional property: Option 1: New Construction Package – $3,300,000 Partner with the highly regarded North Fork Building Company to create a custom 2,900 sq ft modern waterfront home, expertly designed to showcase water views and deliver a luxurious coastal lifestyle. Planned Features Include: 3 en suite bedrooms, additional full bath off the mudroom, main-floor flex room (ideal for a 4th bedroom, home office, or den), Heated waterside pool, covered outdoor living room with kitchen and wood-burning fireplace, private dock + floating swim dock, detached two-car garage with unfinished attic space and breezeway. Interior Highlights: Gourmet kitchen with custom cabinetry, quartz countertops, Thermador appliances, gas fireplace in the living room with custom built-in bookcases, 10’ ceilings on the main level, 9’ ceilings upstairs, white oak flooring throughout, Kohler fixtures, Andersen windows, and recessed lighting. Custom molding package, Walk-in closets in all bedrooms and upstairs laundry room. With final plan approvals nearing completion and permits ready to issue, now is the ideal time to customize your finishes and build your North Fork dream home. Option 2: Purchase As-Is with Approved Plans – $1,499,000 Prefer to build on your own schedule or with your own team? The existing home is also available as-is . This includes: Fully approved architectural plans, ready-to-issue building permits, .37-acre lot on a quiet canal with private dock. Prime opportunity to invest in a trophy location with a head start on construction. Whether you're ready to break ground now or planning for the future, 535 Bay Home Road is a rare chance to own one of the North Fork’s most prestigious waterfront streets — just steps to a private beach and directly across from a scenic vineyard.

535 Bay Home Road, 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.