luxury houses with pool for sale Old Saybrook, United States

Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40 gunite pool flows into a hydrangea-framed landscape. Three bluestone patios for entertaining, dining, and quiet retreat. A newly built two-car garage, wired with new electrical and EV charger-ready. Inside, the transformation is total. A chef's kitchen built around a custom black cherry island with Sub-Zero refrigerator, new double wall oven, and cooktop. A butler's pantry adds a second refrigerator and dedicated wine fridge. Four bedrooms with private en suite bathrooms, including a reimagined primary suite with spa-level finishes. Two home offices. An inviting Family Room. A spectacular Living Room. And a Sunroom - a fully restored 1920s porch with original terra cotta floors and sweeping estate views. Every room is professionally curated with bespoke wallcoverings and custom light fixtures. Steps from the Ivoryton Playhouse, The Copper Beech, and Prive Swiss. Minutes to Connecticut River marinas. Long Island Sound 15 minutes beyond. A truly unique property located in what Yankee Magazine ranks as the #1 small town in New England.

The Benjamin F. Post House, c. 1801, has been thoroughly and thoughtfully updated to provide all the amenities of modern living while respecting the historical integrity of the home. A sidewalk just steps from the property leads directly into the heart of Essex Village, an approximately 20-minute walk to its shops, restaurants, marina, and waterfront. Set on a .48-acre professionally landscaped lot backing up to a quiet wooded area, the fenced-in backyard boasts a beautiful gunite pool and a generous pool deck/patio, perfect for both relaxing and entertaining. Inside on the first floor, there is a light-filled chef's kitchen, well-appointed with upscale appliances including a commercial-grade six-burner range, a large center island, and ample counter space. There is also a formal dining room, a living room with a wood-burning fireplace, and a library with a gas fireplace and built-in floor-to-ceiling bookshelves. An additional room with its own exterior entrance could serve as an office or a potential first-floor bedroom. A lovely four-season sunroom overlooks the pool deck and features a convenient wet bar complete with a beverage chiller. There is also a powder room on the first floor. Upstairs, the primary suite has an updated ensuite bathroom with marble finishes, a large walk-in closet, and a spacious sitting area. There are also two more bedrooms, another den/office area, a second updated bathroom, and laundry. Offering historic character, modern comforts, privacy, and

Tucked away from the road and set above the CT river on over three acres, this amazing waterfront home is also a secluded personal resort, complete with a pool, spa, and private beach. Designed to showcase river views from every vantage point, the home features high ceilings, floor to ceiling windows, and an expansive open-concept floor plan that brings in an abundance of natural light. A living room with a fireplace, formal dining area, and family room all lead out to a large deck, which offers plenty of room for outdoor entertaining or just admiring the scenic waterfront setting. A well-appointed chef's kitchen with a center island and plenty of storage space faces the family room. A first- floor primary bedroom offers an office/sitting area with another fireplace, a generous ensuite bathroom with both a soaking tub and walk-in shower. A spacious laundry/mud room leads from the kitchen to the three-car garage. A sunroom overlooks the pool deck, which includes a gunite in-ground pool, a large patio area, and a fantastic outdoor kitchen with a built-in grill and bar area perfect for al fresco dining. The second-floor landing is open to the first floor below, and has two bedrooms both with ensuite bathrooms, and sitting area. The finished walk-out lower level leads to another patio area overlooking the private beach. A large family room, a full kitchen, two more bedrooms and a full bathroom complete the lower floor, offering plenty of room for visitors.

Welcome to your coastal sanctuary. There's a certain kind of morning that only happens here - sunlight spilling across the water, the breeze carrying in off LIS, and the promise of a day spent outdoors. Set on 1.64 sun-drenched acres w/breathtaking views to the Sound, this 4-bdrm retreat invites you home from the moment you arrive. An open, light-filled floor plan & hardwood floors welcome you, anchored by a kitchen built for gathering: an oversized quartz island, induction stove, and a prep sink for effortless entertaining, and a wine fridge for evening toasts. Warm up by one of two propane log fireplaces in the living room and sitting room, or retreat to the primary suite with its walk-in closet & spa-like bath. Radiant-heated baths, plush upstairs carpet, and central air keep every season comfortable, while a new roof, HVAC system, and new Thermopane windows, (2020), mean this home is move-in ready. Outside is where it comes alive: coffee at sunrise in the three-season sunroom, gatherings on the sprawling Trex deck, evenings in the hot tub, and swims in the deck-framed pool with water views from every angle. Steps from a sandy beach and moments from the Four Mile River Boat Launch, your days can start with sunrise walks and end with sunset sails. With I-95 nearby NYC and Boston.

PRIVATE COASTAL CLINTON, CT RETREAT WITH POOL. Welcome to your private oasis in Clinton! Built in 2003 and set on almost 2 private acres, this beautifully designed 4-bedroom, 2.5-bath home offers an ideal balance of functional interior space and exceptional outdoor living. The main level features a fluid floor plan including formal living and dining rooms, a dedicated home office, and a generous kitchen complete with a walk-in pantry. Gather in the cozy family room anchored by a wood-burning fireplace insert, or relax in the light-filled sunroom overlooking your private backyard. Above the garage is a finished bonus room, ready for all sorts of entertainment. Step outside to an outdoor paradise featuring a back deck leading down to an in-ground vinyl pool surrounded by mature greenery for maximum privacy. Additional features include a whole-house generator for uninterrupted peace of mind, shed for outdoor storage, and an unfinished basement offering massive potential for custom expansion, storage, or a home gym. This home offers comfort, independence, and timeless coastal Connecticut charm.

Selden Farm, a landmark 1690s property steeped in history and set in a picturesque corner of Lyme, is once again available for new stewardship. Upheld by only three families since 1695 when it sat on over 6,000 acres, it presents a rare opportunity to own a beautiful country Antique home now set on 9 pastoral acres abutting conservation land with sweeping views of Selden Cove and the CT. River. At its heart is a gracious and authentic 5-bedroom Colonial which exudes history, charm and character. House features include a tavern room, wide board floors, original paneling & moldings, 6 fireplaces and an abundance of windows which invite lovely views and light into each room. Adjacent to the home is a 3-bay garage with self-sufficient guest accommodation for visiting family and friends. Dotted throughout the property are a renovated barn used as a studio/office/ gym, several outbuildings, a greenhouse and sunny open meadow for animals or farming. Two privately situated guest houses (one needing renovation) are ideally suited for in-law, caretaker, or income purposes. Relax by the large saltwater pool with patio and full-service cabana or play tennis on the all-weather court. The land is open, tranquil, and beautifully sited, offering long views, privacy, and a deep sense of place. Rarely does a property combine this level of authenticity, acreage, outbuildings, and river-valley setting in Lyme. Ideal for buyers seeking history, creative space or a generational retreat.

Gracefully blending timeless architecture with exceptional everyday living, this beautifully appointed Colonial offers thoughtfully designed open spaces both inside and out. A welcoming wraparound porch creates an elegant first impression, while the interior unfolds into an open floor plan ideal for entertaining. The chef-inspired kitchen features a generous center island, double ovens, and a sunny breakfast area that opens seamlessly to the expansive family room. Anchored by a cozy fireplace, this space extends effortlessly through sliding doors to an expansive deck overlooking the private backyard. The outdoor setting is a true retreat. Highlighted by a sparkling inground pool and a built-in fire pit nestled on an upper terrace-creating the perfect setting for summer gatherings, relaxing evenings, and outdoor entertaining. The primary suite offers a peaceful sanctuary with abundant natural light, a spacious walk-in closet, and an ensuite bath featuring a whirlpool soaking tub, separate walk-in shower, and dual vanities. Three additional bedrooms provide exceptional flexibility, including an impressive 23' x 23' suite above the garage with hardwood flooring, double closets, independent heating and cooling, and endless possibilities as a guest retreat, home office, fitness studio or Bonus living space. Upper-level laundry adds everyday convenience, while the walk-out lower level includes a partially finished area ready to be customized to your lifestyle. Welcome Home!

Where Architectural Inspiration Meets the Majesty of the Connecticut River. Perched majestically on 15.22 acres along the eastern bank of the Connecticut River, 89 River Road offers a rare convergence of architectural pedigree, natural beauty, privacy, and fully realized lifestyle design. Designed, owned, and meticulously crafted by one of America's leading architects, this 12,836-square-foot compound, completed in 2018, was conceived to inspire creativity, wellness, and a connection to the outdoors. Protected by parkland, Nature Conservancy, and Land Trust preserves, the heart of the home is defined by extensive, floor-to-ceiling glass walls that command uninterrupted, panoramic vistas of the Connecticut River while a scenic jeep road offers direct access to Chapman Creek and the River beyond. A seamless flow connects the breathtaking entertaining and living areas with a variety of outdoor decks and terraces. The estate offers a rare sanctuary designed to fuel both the mind and the body. It features an unparalleled suite of dedicated, professional- grade spaces that defy the ordinary. The Creative Hub: Fulfill your creative inspirations in one of four dedicated studios: a sky-lit art studio, a sky-lit writing/drawing studio, a fabrication studio, and a fully equipped woodworking shop.

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see.

Welcome to 150 Hillcrest Dr N, located in Hillcrest Estates. This offering is a "to be built" opportunity and the images are of another Orient property that this builder wrapped up in 2023. At this point, a very similar style home can be built on this lot or the builder can be hired to do a custom build and tailor the property to a buyer's specifications. The property is elevated, slopes gently SW and will offer sweeping farm/water-views over Orient and out to Narrow River and Long Beach Bay. More information on previous Orient projects can be provided by request or bring your plans and allow your vision for your forever home to come to life!

Located in the quaint town of East Marion this beautifully appointed ranch offers effortless one level living. Set on an acre property, bordering preserved land, this renovated home has been thoughtfully designed with four bedrooms, two of which are ensuite and three full bathrooms.Step inside to an open, light-filled layout where the kitchen flows seamlessly into inviting living room with fireplace and a dining room with vaulted ceiling. There is also a seamless flow between indoor and outdoor spaces-Step outside to a manicured yard with a Gunite heated saltwater pool, a serene private fenced backyard bordering preserved land - a peaceful and tranquil retreat-just moments to Rocky Point Beach, Greenport Village’s shops, restaurants, transportation and the North Fork’s best wineries and farm stands. This is North Fork living at its finest.

This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

Welcome to 177 Warpas Road, a beautifully rebuilt 4 bed, 2.1 bath coastal colonial set on 1.84 acres, bordered by 185 acres of protected land trust. A lighted stone column entrance sets the tone for this home where New England style meets thoughtful modern updates. Set well back from the road, enjoy a rare sense of privacy, complemented by a fresh, updated exterior with new windows, siding, entrance portico, roof and refinished flooring (all 2025). Inside, the 1st floor layout is designed for easy living and effortless entertaining. The den with custom built-ins opens to a bright, eat-in kitchen with captivating property views. The dining area, living room and family room also offer views of the perfectly manicured and landscaped grounds. A stone fireplace and cathedral ceiling detail the family room and a wall of glass frames views of the resort-like backyard. The second floor offers an updated primary bedroom with tray ceiling. A newly created attic space provides a valuable head start for expansion with potential to add additional square footage. A roomy two-car garage adds convenience year round. Outdoors, an expansive two level patio incorporates a 2-year-old 630 square foot Timbertech deck with automatic awning that creates a shady outdoor living space. Across the lush lawn, a saltwater pool and a putting green create a true country club atmosphere. A full property irrigation system keeps the professionally maintained lawn and landscaping looking beautiful!

Welcome To 5-7 Haddam Dock Road Located in Haddam, Connecticut. Discover A Rare Riverfront Opportunity Offering Two Homes On One Lot, Breathtaking River Views Of The Connecticut River, and Your Own Private Boat Dock. This Property Is Perfect For Multi-Generational Living, Guest Accomodations, Or Rental Income. The Main House Showcases Soaring Windows That Frame The Picturesque Waterfront, Filling The Living Spaces With Natural Light While Creating A Seamless Connection To The Outdoors. This Home Offers 4 Large Bedrooms With Private Baths and Plenty Of Closet Space For Storage. Step Outside To An Expansive Entertaining Area Featuring A Sparkling Gunite in Ground Pool, Spacious Patio, Full Outdoor Kitchen, and Multiple Areas Designed For Relaxing Or Hosting Family and Friends. The Second House Provides Privacy and Flexibility, Making It Ideal For Visitors, Extended Family, A Home Office, Or An Income-Producing Rental. This High Ranch Style Home Has An Open Concept Floor Plan With High End Wolf Appliances, Wide Plank Tile Throughout, and Custom Built Ins Accenting Most Of The Rooms, and Has Double His and Her Walk in Closets. Situated On Beautifully Landscaped Grounds, This Exceptional Prroperty Also Features Direct River Access With A Private Dock, Allowing You To Enjoy Boating On The Connecticut River, Fishing, Kayaking, Or Simply Taking in The Peaceful Waterfront Setting From Your Own Backyard.

Experience a rare combination of privacy, architecture, open water, and resort-like amenities at 66 Gardiners Bay Drive, an exceptional waterfront offering on Shelter Island. Set against sweeping views of Gardiners Bay, the property features a private beach, expansive lawns and gardens, and a spectacular gunite pool positioned directly along the water. The main residence was designed by renowned architect Andrew Geller, whose distinctive modernist vision is reflected in the home's thoughtful relationship to its extraordinary setting. The five-bedroom residence features five en-suite bathrooms, an open living and kitchen floor plan, and walls of windows that bring in abundant natural light while capturing panoramic Bay views. Both the main residence and guest house underwent a comprehensive renovation in 2022, with every aspect carefully considered. The renovation encompassed the kitchen, all bathrooms, major systems, and numerous other elements of both properties. Nothing was overlooked, with an emphasis throughout on quality, craftsmanship, and the finest materials and fixtures. Outdoor living is at the heart of the property. A generous deck, fully equipped outdoor kitchen, waterside lounge, and gunite pool create an exceptional setting for entertaining or simply enjoying the beauty of the Bay. The property also benefits from a grandfathered irrigation system, helping maintain lush green lawns and established gardens throughout the summer-an especially valuable amenity for a waterfront property of this scale. A beautifully renovated two-bedroom, three-bath guest house provides exceptional accommodations for family and guests, while maintaining privacy from the main residence and enjoying its own stunning water views. A full, newly refinished basement in the main house adds further living and recreational space. What makes 66 Gardiners Bay Drive particularly compelling is the remarkable breadth of what is offered in one property: privacy, expansive lawns and gardens, a private beach, sweeping open-water views, a waterside pool, sophisticated outdoor entertaining spaces, a renowned architectural pedigree, a beautifully renovated guest house, and a comprehensive renovation already completed. Rarely at this price point can one find so much on the water. The combination of setting, amenities, privacy, architectural significance, and turnkey condition makes 66 Gardiners Bay Drive a truly unique and compelling Shelter Island offering.

Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the lens of effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island’s premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.

CUSTOM MADISON ESTATE: Private 2.11-Acre Oasis with Heated Inground Pool. Custom-built in 2001 for the original owners, this exceptional Madison estate offers over 5,400SF of meticulously designed living space set on a private 2.11-acre lot. Designed for both refined daily living and high-end entertaining, the home boasts 4 bedrooms, 4.5 bathrooms, and an ideal layout for modern flexibility. At the heart of the main level, an oversized family room features dramatic vaulted ceilings and a cozy wood-burning fireplace, creating an inviting space to gather. Distanced remote work is effortless with two dedicated home office spaces. The expansive floor plan spans 4,421 square feet between the 1st & 2nd floors, supplemented by an additional 998 square feet in the partially finished basement-perfect for a rec room, craft area, home gym, or media center. A rare highlight is the versatile bonus room above the garage, complete with its own dedicated full bath and laundry area-making it ideal for an au-pair suite, guest quarters, or a private creative studio. Outdoors, step into your own private New England retreat. The professionally landscaped grounds feature a heated inground pool surrounded by lush greenery, offering complete tranquility and an idyllic summer setup. Over 7 acres of Land Trust are located behind the home. Conveniently located near Rt 80, for easy access to New Haven and all points north, this turn-key custom home represents shoreline living at its finest!

Welcome to your own private retreat! This exceptional custom 3-bedroom Cape Cod home sits on 2 sprawling, peaceful acres and offers the perfect blend of modern upgrades and ultimate outdoor living. Step inside to a main floor designed for both everyday comfort and effortless entertaining. Remodeled Kitchen: The heart of the home features updated cabinetry and finishes, anchored by a cozy wood-burning stove. Family Room: Highlighted by a handsome warm fireplace, creating an inviting space to gather. Formal Dining Room: Elegant layout perfect for hosting dinners and holiday gatherings. Formal living room ,also with wood burning fireplace adds to your entertaining experience Primary Suite: Features a warm fireplace and a beautifully remodeled full en-suite bath. Additional Bedrooms: Two generously sized bedrooms, each featuring direct access to an attached full bathroom. Resort-Style Backyard & Grounds Step outside to an outdoor haven engineered for relaxation, recreation, and pet-friendly living. In-Ground Pool Compound: Complete with a stone waterfall feature, expansive barbecue area, separate dressing room, and a summer kitchen for poolside dining. Outdoor Entertaining: Enjoy crisp evenings around the fire pit or relax in the covered picnic area. Covered Porch: Overlooks the entire pool area, offering a shady vantage point to unwind. Fully Fenced in back yard keep your furry friends close by

Welcome to 12 Clinton Avenue, a distinguished waterfront estate nestled in the heart of Shelter Island Heights, NY. This remarkable property spans 1.5 acres along the serene Dering Harbor, offering an unparalleled lifestyle marked by elegance and tranquility. With 10,000 square feet of meticulously designed living space, this gated estate presents a rare opportunity to own a piece of paradise. The residence boasts seven spacious bedrooms and six and a half luxurious bathrooms, each adorned with high-end finishes and extensive use of natural marble. The grandeur of the home is immediately apparent upon entering the soaring great room, which doubles as a library, complete with a massive fireplace that serves as the focal point. The walnut flooring throughout adds warmth and sophistication to the expansive layout. The kitchen is a chef's dream, featuring a vast prep area and top-of-the-line appliances, seamlessly connected to a formal dining room perfect for hosting intimate gatherings. The screened-in porch, equipped with storm shutters, offers breathtaking views of the harbor, creating an ideal space for relaxation and entertainment. Outdoor amenities are equally impressive, including a private dock, a water-side gym, and a pool with an automatic cover. The magical landscaping enhances the property's allure, while the garden and irrigation system with a cistern ensure year-round beauty. The block paver driveway leads to a two-car garage, providing ample parking and storage. For those seeking leisure and community engagement, the estate offers access to community tennis courts and a beach club. The village lifestyle is serene, with no need for a car to access local restaurants, shops, coffee bars, and the post office, all within walking distance. Additional features include a bar, sauna, and an office room lined with bookcases offering stunning water views. The entry foyer sets the tone for the home's elegance, while the extensive use of luxury finishes throughout ensures a sophisticated living experience. This property is a testament to refined living, combining privacy, luxury, and convenience in one of New York's most coveted locations. Don't miss the opportunity to own this exceptional estate, where every detail has been thoughtfully curated to provide an unmatched living experience.

This 2024 constructed 5,800-square-foot modern waterfront residence, built by Fountainhead Construction Inc., offers 250 feet of sandy beach and extraordinary panoramic water views. 180 degrees of sweeping water views from Crab Creek to North Haven Point and across Great Peconic Bay, with 250 feet of sandy beach along the shoreline. Walls of glass in the kitchen, dining area, living room, and select bedrooms frame the remarkable water views and glowing sunsets, creating a seamless connection between indoors and out. Step onto the waterfront patio or terrace to experience the setting even more fully. The sleek five-bedroom home includes six full baths and two half baths, with sophisticated finishes and amenities throughout, including 10-foot doors, a kitchen with custom Italian cabinetry and natural stone countertops, a fireplace, media room, and heated waterside pool. Set on 2.12 secluded acres, this exceptional property offers a rare opportunity for refined waterfront living

Discover a rare and compelling offering on Shelter Island where historic character and modern sophistication exist in perfect harmony. 7 Stearns Point Road presents a unique opportunity to live expansively-either as a private family compound or as an owner-occupied five-bedroom Bed & Breakfast. The residence is set on 0.70 acres in the heart of Shelter Island Heights, just moments from Crescent Beach and Sunset Beach. Spanning approximately 5,838 square feet, with an additional 2,588-square-foot full-height basement, the home seamlessly blends timeless architectural details with contemporary comfort. Arranged across two distinct structures connected by a covered breezeway, the property's nine bedrooms and nine bathrooms are thoughtfully distributed between the original Annex-offering seven bedrooms-and a recently completed extension featuring two additional ensuite bedrooms. The new wing is further distinguished by a dramatic double-height living area and a dedicated wellness room, equally suited for private residential use or boutique hospitality. Generous entertaining spaces include two living rooms and a well-equipped kitchen designed to accommodate both intimate gatherings and larger-scale hosting. Outdoors, the grounds evoke a private resort atmosphere, featuring a heated 40' x 18' gunite pool, mature landscaping, and multiple areas for relaxation and entertaining. Two separate driveways provide added convenience and privacy for owners and guests alike. With zoning and approvals allowing for an owner-occupied five-bedroom Bed & Breakfast, along with the benefit of an existing liquor license for guest use, the property offers a rare level of versatility. Whether envisioned as a legacy family retreat, a refined island escape, or a boutique hospitality venture, the possibilities are both flexible and compelling.

Shelter Island Ranch style home with 3 bedrooms and 2 bathrooms. Situated close to town and easy access to all beaches and either ferry this adorable home is currently configured as a 2 bedroom (large oversize primary bedroom with sliders to deck, guest bedroom, 2 newly renovated bathrooms, kitchen with new appliances, open living and dining area has stone surround fireplace and sliders to deck area. The lower level has finished space, laundry area, and doors to steps to access pool area. Large attic space and a separate garage with second level storage space.

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.