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.

ML# :3548818   Welcome to your Bay Front paradise on the North Fork! This home has every aspect of beach living. Incredible views of Bug Light and Shelter Island. Two lots comprising 1.38 acres and over 286 feet of expansive sugar sand beach. Featuring an open gracious floor plan. 5 bedrooms, 4 baths, wraparound porch, outdoor shower, waterside gunite pool, outdoor kitchen area, a garage that houses a gym, living loft area and a full house generator! The additional lot has a building envelope for a 2700+ square foot home. The beauty of all of this and located in Flood Zone X! Surrounded by North Fork renowned farm stands, restaurants, beaches, marinas, boating, award winning wineries and great shopping.

ML# :3514107   Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story.

ML# :3546951   Boat slip in your backyard. This Bayview waterside estate sits on nearly 2.5 acres of secluded property in the coveted Shellfisher Preserve association comprised of three spectacular custom homes. Water views and 300 feet from your private deeded bay beach and your own 70’ long deep-water stationary dock in a private marina. Huge, detached 1, 800 sqft post-and-beam barn style garage. The property is flanked by a spectacular 650’ long deep water, tidal lagoon owned and maintained through the Peconic Land Trust. This traditional style home was custom built, ground up and features 3 bedrooms upstairs with large master suite, possible first floor bedroom or den. 3 car garage has finished studio space above with exquisite water views. Site plan with room for a 20x40 Gunite pool in the large grassy and level backyard which is fully deer fenced.

ML# :3540145   **Billard-Tuthill House: A Historic Boutique Vineyard Estate** Step Into A Timeless World Of Charm And Elegance At The Billard-Tuthill House, A Historic Farmhouse Dating Back To Pre-1858 Nestled Amidst 17.5 Acres Of Pristine, Sun-Drenched Cutchogue Land In The Sunniest Spot In New York State. This Exquisite Estate Combines The Allure Of A Boutique Vineyard With The Promise Of A Family Compound Offering A Legacy Property That Is Truly Unparalleled. As You Wander Through The Fertile Soils And Lush Vineyards That Stretch As Far As The Eye Can See, You’ll Be Captivated By The Beauty And Tranquility Of This Enchanting Landscape. The Development Rights Intact Land Provides Endless Possibilities For Expansion And Customization Allowing You To Create Your Own Piece Of Paradise In The Heart Of Wine Country. The Lovingly Restored Historic Farmhouse Exudes Warmth And Character At Every Turn. From The Original Hardwood Floors To The Handcrafted Woodwork, Every Detail Tells A Story Of A Bygone Era. With Multiple Bedrooms, Cozy Living Spaces, And A Gourmet Kitchen, This Is The Perfect Place To Create Lasting Memories With Family And Friends. Outside, The Sprawling Grounds Offer A Wealth Of Opportunities For Outdoor Recreation And Relaxation. Take A Stroll Through The Woodlands In The Distance, Enjoy A Picnic Among The Vines, Or Simply Unwind On The Patio As You Take In The Panoramic Views Of The Surrounding Countryside. With Two Road Frontages And A Barn Ripe For Your Vision, This Property Offers Endless Possibilities For The Discerning Buyer. Whether You Dream Of Crafting Your Own Vineyard Estate, Creating A Multi-Generational Sanctuary, Or Simply Escaping The Hustle And Bustle Of City Life, The Billard-Tuthill House Offers The Perfect Blend Of History, Charm, And Natural Beauty.

ML# :3549432   Escape to paradise at this stunning waterfront home nestled on 8.9 acres of land along West Creek, providing access to the beautiful Peconic Bay. This remarkable property offers deeded beach rights just steps away and is situated in a serene setting that is simply irresistible. With seven generously-sized bedrooms, each featuring its own private ensuite bathroom, there is plenty of space for relaxation and privacy. The culinary kitchen is a chef’s dream, boasting a spacious layout that is perfect for entertaining. In addition, the property features a 32-foot indoor pool, complete with an exhilarating water park slide and a soothing hot tub, ensuring year-round entertainment. Whether you’re taking a break from remote work or winding down after a long day, the porch with fireplace is the perfect spot to gather with friends and family, while enjoying the breathtaking views. Speaking of views, nearly every room in this home offers captivating waterviews, allowing you to fully immerse yourself in the natural splendor that surrounds you. Outdoor activities abound, with opportunities for golfing and tennis at the nearby country club, as well as swimming, fishing, and kayaking right from your own backyard. This property also presents an excellent opportunity for a bed and breakfast, with its spacious layout creating an inviting retreat for guests. Immerse yourself in the tranquility and natural beauty of this incredible waterfront home, and experience a lifestyle that seamlessly combines luxury, comfort, and the wonders of nature. This home also features an expansive great room, multiple fireplaces, a theatre room, a gym and has potential for an inground pool and pickleball court. Truly a gem of the North Fork!

ML# :3550414   Introducing one of the North Fork’s most iconic properties, seamlessly blending historical grandeur with contemporary living. Originally constructed circa 1915, this Georgian estate served as additional living quarters for the family of the former 40-acre waterfront Cosden estate. Today, this exceptional residence offers over 6000 square feet of luxurious living space featuring six bedrooms, all ensuite and is situated on a serene acre of land positioned across from a scenic preserve. An entertainer’s dream, the house welcomes guests with a magical courtyard entrance, setting the stage for epic gatherings with family and friends. Inside, soaring ceilings and abundant windows infuse the home with natural light, creating a bright and inviting atmosphere. A large great room features trayed ceilings, herringbone floors and a huge wood-burning fireplace, adding warmth and character to the space. The recently renovated chef’s kitchen is anchored by an oversized center-island with an enormous custom skylight above. A formal dining room with vaulted ceilings awaits holidays and dinner parties. A large playroom serves as a flex media room. The south-wing of the residence features the original stables with a secluded and private office just beyond. Additionally, a large temperature-controlled wine cellar in the basement caters to connoisseurs and collectors alike. Step outside to the park-like backyard, where a heated gunite pool awaits amidst mature specimen trees and ornamental plantings, offering a private retreat. An outdoor shower is designed to take in the beautiful gardens. A timeless East End investment in the heart of the North Fork.

ML# :3527549   This lovingly restored 1902 shingle-style beach house on the Peconic Bay is a great place to relax, and enjoy the beauty of the North Fork. Step back into an era of gracious living, with all the amenities of modern life. Boasting incredible southern views, bay breezes, and generous proportions, this beautiful home is sure to exceed your expectations. The four bedrooms in the main house, two with balconies overlooking the Bay, provide plenty of space for your family and guests. And if you need a little extra room, the separate cottage is sure to come in handy. Some of the original features include high ceilings, tall windows, and hardwood flooring. The sunny, updated kitchen has a large center island, leading to a generous formal dining space. Open to the generous living room with wood-burning fireplace, your gaze is drawn towards the water views and the fully enclosed sun porch for lounging, dining and entertaining. A den/study on the first floor is complete with built-in bookcases and cabinetry, and the first floor bath has both a claw-footed tub and walk-in shower. With 106’ of waterfront, the double bulkheading allows for a private beach area and (bonus!) winch to help you get your water toys in and out of the bay. This charming historic retreat is close to shopping, farmstands, and vineyards. Breathe deep and relax.

ML# :3525611   Here is the quintessential New Suffolk guest house. This cottage is the guest house for property 3120 Grathwohl Road Please see the listing MLS 3525609. Two for the price of one! It will not being sold separately. It will be sold as part of the 3120 Grathwohl Rd. property (1000-8-110-7)

ML# :3525609   Discover charm in New Suffolk with two inter-connected residences. Nestled on the property is a charming year-round cottage see MLS listing 3525611 Enjoy the serenity year-round, whether by the fireplace in the winter or in your gunite pool with cascading waterfalls and a fully equipped outdoor kitchen- perfect for al fresco dining and entertaining. Both residences are fully permitted as legal Southold Town rentals. Together these two homes offer the perfect balance of space and privacy for you and your loved ones.