Refine Search
Sort by
$905,000
4 Beds 3 Baths 1032833 MLS
Pristine and sophisticated, this beautifully customized 4-bedroom, 2.5-bath ranch offers a spectacular open-concept design perfect for today's lifestyle. Originally built in the 1960s, the home has been thoughtfully updated over the years to reflect timeless elegance and exceptional craftsmanship. The stunning center island kitchen features a dramatic 7-foot black granite island, Sub-Zero refrigerator, Bosch dishwasher, GE appliances, under-counter microwave, and cooktop. Hardwood floors and custom built-ins enhance the home's warmth and character, while the spacious living and entertaining areas flow seamlessly to the rear deck for effortless indoor-outdoor living. A truly special home that is impeccably maintained and a must see.

22 S Lot Road, Smithtown

$859,990
3 Beds 2 Baths 1031558 MLS
Set on 1.25 acres backing directly to the Nissequogue River Preserve this Sprawling Ranch offers a setting that is truly special. Protected woodland replaces neighboring homes, offering a peaceful backdrop where wildlife and changing seasons become part of everyday life. Inside, this inviting ranch features 3 bedrooms, 2 full baths, a farmhouse-inspired kitchen with breakfast nook, separate formal dining room, and beautiful hardwood floors throughout. The spacious family room is filled with natural light and anchored by a brick wood-burning fireplace with removable electric insert, while the formal living room showcases exposed wood beams and a wood-burning stove. Just off the primary suite, a sun-filled sitting room provides the perfect retreat to enjoy your morning coffee while taking in views of the surrounding landscape. Outside, enjoy summer days by the fenced 20x40 in-ground pool with a 2-year-old liner, or relax on the wood deck and brick patio surrounded by mature trees and the peaceful sights and sounds of nature. The fully permitted barn with attached carport and covered patio offers incredible versatility with potential uses including equestrian space, workshop, studio, home gym, or a cottage for extended family or rental income with proper permits. Additional features include a brand-new roof with flashed skylights, new gutters, propane service for cooking and laundry dryer, two-car attached garage, and a full unfinished basement with egress window offering even more possibilities. Conveniently located minutes from Blydenburgh County Park, Caleb Smith State Park Preserve, beaches, shopping, dining, and within the highly acclaimed Smithtown School District, this is a rare opportunity to enjoy the peace of a private setting while staying connected to everything Smithtown has to offer.

16 Landing Meadow Road, Smithtown

$678,000
4 Beds 3 Baths 1031653 MLS
Classic Colonial home offering spacious, and comfortable living . The expansive living room and beautiful wood floors throughout the home create a warm and inviting atmosphere. The eat-in kitchen flows seamlessly into the den, featuring a cozy wood-burning fireplace—perfect for everyday living and entertaining. The primary bedroom boasts an updated marble en-suite bath, while the additional bathrooms have also been tastefully renovated with quality finishes. In addition there are 3 nicely sized bedrooms on the second floor. The recently remodeled basement features durable luxury vinyl plank flooring and an outside entrance, providing versatile space for recreation, or a home office.. Step outside to enjoy the backyard deck with retractable awning, ideal for relaxing or hosting gatherings. Conveniently located near local shopping, the Long Island Rail Road, area beaches, fine dining, and Stony Brook University, and Stony Brook University Medical Center, this home offers the perfect combination of comfort, and accessibility. Smithtown Schools

322 2nd Avenue, Saint James

$990,000
4 Beds 3 Baths 1028829 MLS
Welcome home to this Post Modern Colonial, where an impressive two-story entry foyer creates a grand first impression. Beautiful hardwood floors, finished in a modern gray tone, extend throughout the entry foyer, staircase, formal living room, and formal dining room, creating a warm and cohesive flow. Designed for today's lifestyle, the home features a desirable open-concept kitchen and family room with a wood-burning fireplace flanked by custom built-ins, making it the perfect gathering space. The spacious primary suite offers a walk-in closet and a private ensuite bath, while a conveniently located first-floor laundry/mudroom with a new front-load washer and dryer adds everyday functionality. Set on a landscaped .43-acre property in the heart of St. James, the private, fenced backyard is an entertainer's dream, featuring an expansive paver patio with a built-in firepit plus a separately fenced saltwater inground pool with waterfall. Pool updates include new filter, heat pump, and Loop-Loc cover, as well as new pavers surround the pool area, while the gazebo provides the perfect place to relax. Thoughtfully updated for today's modern lifestyle, the home features a Smart Home system allowing you to control lights, doors, and central air from your smartphone, along with a security system with cameras for added peace of mind. Additional improvements include a 2020 roof, a 2024 natural gas heating system, CAC with the second-floor compressor replaced in 2023, a separate gas hot water heater, 200-amp electric service with a dedicated panel for an EV charger, and owned solar panels installed in 2020, providing lower electric costs and valuable property tax exemptions. (Note: Taxes being professionally grieved with an estimated $3,300 reduction; grievance is transferable to the Buyer.) Ideally located on a cul-de-sac and just a short walk to Lake Avenue's shops and restaurants, including the new Galiano Wine Bar. This home also offers beach rights to multiple Town of Smithtown beaches, proximity to parks, hiking trails, and nature preserves, and is situated within the highly regarded Smithtown Central School District.

4 Patricks Way, Saint James

$775,000
3 Beds 2 Baths 1027993 MLS
Welcome home! This pristine 3-bedroom, 2-bathroom Splanch sits perfectly on a flat, fenced .25-acre lot in a sought-after, sidewalk-lined neighborhood. Beautifully merging modern updates with exceptional energy efficiency, this residence is entirely turn-key. From the moment you arrive, the new double-wide paver driveway provides the convenience for parking multiple cars without the chaos. Enjoy the newer kitchen and updated bathrooms. Bright sliders lead directly from the home to a brand-new deck, perfect for summer barbecues and outdoor dining or relax by the warm gas fireplace in your inviting main living space. Stay comfortable year-round with efficient gas heating and central air conditioning in a home that is fully equipped with solar panels to drastically lower your monthly electric bills. This property is situated in the Smithtown School District. It offers easy access to the town's Main Street, dining, and shopping, as well as gorgeous state and county parks. Commuting is effortless and convenient to major highways and the Long Island Rail Road (LIRR). Everything you could want is waiting for you right here.

11 Sandalwood Drive, Smithtown

$3,995,000
7 Beds 6 Baths 1022766 MLS
Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.

38 Landing Meadow Road, Smithtown

$1,599,999
6 Beds 5 Baths 1021330 MLS
Nestled on over 2 private, level acres in the prestigious Village of Nissequogue, this beautifully maintained center hall Colonial offers 6 bedrooms, 4.5 baths, and an exceptional layout designed for comfortable living and entertaining. A grand entry foyer welcomes you into a home featuring soaring cathedral ceilings, spacious living areas, and a spectacular 20.6' x 30' kitchen with abundant cabinetry and workspace that serves as the heart of the home. The oversized formal dining room is ideal for hosting gatherings, while the versatile floor plan includes two primary suites on the main level and a third primary ensuite upstairs, along with three additional generously sized bedrooms and another full bath. Step outside to your private backyard retreat featuring a heated in-ground pool surrounded by mature landscaping. Additional highlights include a two-car garage, beach access, mooring rights, and an exceptional North Shore location offering privacy, tranquility, and estate-style living.

15 Stillwater Road, Saint James

$2,049,000
4 Beds 4 Baths 1014240 MLS
Exceptional Custom Estate in the Heart of St. James Proper, Situated on 1 Acre of Meticulously Maintained & Landscaped Property with a Resort Style Bucolic Yard. A Covered Front Porch leads into a Double Height Entry Foyer. Offering Four Bedrooms, Four Full Baths, a Family Room with Wood Burning Fireplace, Hardwood Floors, Built-ins & Custom Millwork Throughout. Private Den, First Floor Full Bath, Primary Ensuite with Two Walkin Closets, Propane Fireplace, Private Balcony & Custom Private Bath with Shower, Whirlpool Tub, Bidet & More. Three Additional Bedrooms on Second Floor & Brand-New Full Bathroom. Finished Basement 9' Ceilings with Custom Millwork, Outside Entrance, Custom Bar, Office, Full Bath, Movie Theatre & Much More. Bucolic Rear Yard Encompasses a Double Height Paver Patio, Outdoor Kitchen, Rear Awning, 35x35' Saltwater Heated Inground Pool with Waterfall, Covered Entertainment Area, Tennis Court with Pickleball & Basketball. Rear Stadium Lighting, Built-in Fireplace, Elevated Gazebo, Two Car Detached Garage & Rear Pool House Area. Four Car Garage Total. 400 Amp Electric. Two Zones CAC, two 275 Gallon Oil Tank in Basement. Central Vacuum, Low Line Septic, Built-in Fishtank. Mature Landscaping, Landscape Lighting, Architectural Roof, Pool Table & Much More. Must See to Appreciate. All information to be verified independently by Buyer/Agent. Inquire About CO's.

67 Sunny Road, Saint James

$2,399,000
6 Beds 5 Baths 1010665 MLS
Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with expansive living spaces filled with natural light of generous proportion and seamless indoor-outdoor flow creating a tranquil retreat just moments from the harbor, beaches, yacht clubs, vineyards and nature preserves. Set on two beautifully landscaped level acres of property designed for both everyday enjoyment and sophisticated entertaining. This private estate seamlessly blends timeless elegance, modern luxury, and resort-style living. A grand two-story foyer introduces the home's sophisticated interiors, where soaring cathedral ceilings, gleaming hardwood floors, abundant natural light, and exquisite architectural details create an atmosphere of warmth and refinement. Thoughtfully updated throughout, every space has been designed with both everyday comfort and effortless entertaining in mind. The recently renovated chef's kitchen serves as the heart of the home, featuring a dramatic Crawford ceiling, custom crown and box moldings, quartzite-topped center island, and a suite of premium appliances including a Sub-Zero refrigerator, Bosch range, double ovens, microwave drawer, and dishwasher. The kitchen flows seamlessly into the impressive great room, highlighted by a floor-to-ceiling stone wood-burning fireplace and walls of windows overlooking the picturesque grounds. Elegant entertaining spaces continue with a gracious formal living room accessed through glass pocket doors, and a spacious dining room perfectly suited for hosting intimate gatherings or larger celebrations. The main level offers five generously proportioned bedrooms and three full bathrooms, including two recently renovated baths appointed with refined finishes. Upstairs, an expansive loft with hardwood floors overlooking the great room provides additional living and entertaining space and leads to the luxurious primary suite. This private retreat features hardwood flooring, custom closets, detailed millwork, and a stunning newly renovated spa-inspired bath complete with a soaking tub, oversized glass-enclosed shower, dual vanity, and exquisite Italian tile. The outdoor setting is nothing short of extraordinary. Professionally landscaped grounds surround a tranquil in-ground pool, complemented by multiple paver patios designed for elegant outdoor entertaining and relaxation. A sprawling Trex deck extends nearly the entire length of the home, creating a seamless connection between indoor and outdoor living. Additional highlights include a fully finished lower level with a full bath, offering exceptional flexibility for recreation, fitness, guest accommodations, or extended living space. Car enthusiasts will appreciate the rare offering of four garage spaces, including two attached and two detached garages. Recent improvements include extensive interior and exterior painting, newer windows, custom closet systems, wood flooring throughout most of the house and numerous thoughtful upgrades throughout. A wonderful opportunity awaits for you to own this property and reap the rewards of resort living in the White Spruce Farm Community within the Village of Head of the Harbor. Taxes Include Village Taxes of $3,199

15 The Chase, Saint James

$775,000
5 Beds 2 Baths 992164 MLS
Stunning 5 possible 6-Bedroom High Ranch in Smithtown East Schools: Welcome Home To This Sprawling And Impeccably Maintained 5-Bedroom, 2-Bathroom High Ranch, Perfectly Situated On An Expansive, Oversized Property Including An Additional Lot. Boasting Incredible Curb Appeal And An Oversized Driveway. This Residence Offers The Rare Combination Of Spacious Interior Living And A Massive Outdoor Oasis. The Heart Of The Home Features A New Updated Gourmet Kitchen Equipped With Modern Finishes, including Soft-Close Cabinets, Stainless Steel Appliances, Center Island, And Quartz Counter Tops, Seamlessly Flowing Into Bright, Open Living Spaces. Both Full Bathrooms Have Been Recently Renovated With Stylish, Contemporary Fixtures. With Five Generous Bedrooms With Ample Closet Space, A Formal Living Room, Dining Room, And Family Room. There Is Ample Space For A Home Office, Guest Quarters, For A Growing Household. Step Outside To Your Private Retreat, Featuring A Sparkling Inground Swimming Pool Surrounded By Professional Landscaping And Vast Green Space, Plus A Screeded-In Patio Space Perfect For Entertaining Or Peaceful Relaxation. Located In The Highly Sought-After Smithtown School District, This Move-In-Ready Gem Offers The Perfect Blend Of Luxury Living, Comfort, And Prime Location. Don't Miss The Opportunity To Own This Unique, Oversized Property!

4 Florence Street, Nesconset

$6,800,000
5 Beds 10 Baths 000034 MLS
Waterfront – Set along 243’ of pristine Long Island Sound frontage, this extraordinary waterfront estate offers a truly rare combination of sweeping unobstructed water views, direct access to a sandy beach, and beautifully manicured level grounds with no high bluff — creating an unparalleled coastal setting rarely found on the North Shore. Privately nestled at the end of a private cul-de-sac on 2 lush acres, this over 7,000 square foot custom residence plus an unbelievable entertainment lower level is surrounded by magnificent specimen plantings, manicured gardens, and expansive Ipe Brazilian walnut decking designed to embrace the breathtaking waterfront backdrop from every angle. Nearly every room captures stunning water views, creating a seamless connection to the shoreline while filling the home with natural light and tranquility. Custom built with uncompromising quality and craftsmanship, the residence showcases high-end custom finishes, exquisite detailed moldings, elegant designer touches, and only the finest materials and systems throughout. Sophisticated yet inviting, the home offers an exceptional blend of refined luxury and relaxed coastal living. Every detail has been thoughtfully curated with no expense spared. Designed for both grand-scale entertaining and intimate everyday living, the property offers exceptional indoor and outdoor gathering spaces where unforgettable memories are waiting to be made. Enjoy breathtaking sunsets over the Long Island Sound with unobstructed views stretching to Connecticut, all from the privacy of your own extraordinary waterfront retreat. Ideally located approximately 60 miles from Manhattan and moments from fine dining, shopping, marinas, Stony Brook University, and Stony Brook University Hospital, the property offers a rare blend of private coastal living and everyday convenience A true private oasis, this remarkable estate offers the feeling of being worlds away while enjoying the beauty, serenity, and prestige of luxury waterfront living at its absolute finest.

6 Pheasant Run, Nissequogue

$6,750,000
6 Beds 10 Baths 990237 MLS
Soundview Haven is nestled on 11.2 Acres of verdant lawn, lush plantings and mature trees in the picturesque Incorporated Village of Nissequogue. Perfectly positioned on the property with magical views of the Long Island Sound and 322 feet of beachfront, this exceptional estate creates its own secluded enclave-ideal for those seeking privacy and tranquility. The gated entrance opens to a long bluestone drive that leads to this exquisite Hamptons shingled styled residence with fine architectural details and remarkable craftsmanship. Measuring more than 9000 square feet, this custom residence features a grand entrance hall with a spiral staircase, fine millwork and wood flooring throughout. Additional spaces include formal living room and dining room, butler's pantry, great room with soaring ceiling and floor to ceiling stone fireplace, Chef's kitchen with gathering Island and top of the line appliances, breakfast room, movie theater, conservatory with stone fireplace, 6 bedrooms, 7 full baths, 3 half baths, 2 laundry rooms, and 3 car garage that can accommodate lifts. The finished lower level offers additional space for recreation, a gym, and has an entrance to the outside. Professionally landscaped outdoor areas include Laykold tennis court, sparkling heated inground pool and spa, outdoor kitchen, firepit, cabana, slate patio and walkways. Smart home integration and a Briggs and Straton generator provide convenience and safety. Relax in this peaceful setting, stroll down to your beachfront and enjoy a swim, or delight in entertaining guests in these pleasant surroundings. Soundview Haven will captivate the most discerning buyer with its luxurious amenities, breathtaking water views and tranquility.

697 Short Beach Road, Nissequogue

$1,169,000
4 Beds 3 Baths 966893 MLS
Set on 1.25 beautifully maintained, level acres within the highly desirable community of St. James, this exceptional property offers the perfect balance of space, privacy, and versatility — with a rare equestrian component that elevates it beyond the ordinary! The impeccably maintained Center Hall Colonial features 4 bedrooms and 2.5 baths with a gracious, flowing floor plan designed for both comfortable everyday living and effortless entertaining. Rich wood floors run throughout the home, complemented by tasteful neutral décor and abundant natural light. The custom updated eat-in kitchen is thoughtfully appointed with stainless steel appliances, granite countertops, and a charming dinette area overlooking the expansive property — creating a seamless indoor-outdoor connection. Formal living and dining rooms provide an elegant gathering space, while the warm and inviting den has a wood burning fireplace and offers a cozy retreat. The primary bedroom features a private ensuite bath, and three additional generously sized bedrooms complete the second level. Updated windows and bathrooms, central air conditioning, a full finished basement with outside entry, and a two-car garage enhance everyday convenience. Additional improvements include low-maintenance vinyl siding, and a generator transfer switch for added peace of mind. Pride of ownership is evident throughout. For those seeking additional flexibility, the property is thoughtfully equipped for equestrian use. A center aisle working barn includes four 12x10 matted breeding stalls, 50-amp electric service, water, heat and ventilation fans, loft exhaust system, and phone lines. Outdoor amenities feature a riding ring with lighting, sprinkler system for dust control, paddock and grazing areas, wash rack, and full secondary fencing. The grounds provide a private and versatile environment suitable for training, conditioning, or leisure riding — all within the comfort of your own property. Located within the Smithtown School District, this unique property is just minutes from shopping, restaurants, parks, transportation, Stony Brook University, Stony Brook Hospital, and the beaches of the Long Island Sound. Offering a rare combination of space, flexibility, and convenience, this exceptional St. James property presents an outstanding opportunity to create something truly special. Whether enjoyed as-is or tailored to suit your vision, this remarkable offering is ready for its next chapter.

14 Hillside Avenue, Saint James

$1,099,000
4 Beds 3 Baths 936825 MLS
Why settle for someone else’s dream when you can build your own? Welcome to this brand-new TO BE BUILT colonial-style home designed with today’s lifestyle in mind. Set on a deep 15,840 sqft lot, this to-be-built beauty will offer over 2,400 square feet of fresh, functional living space and the kind of craftsmanship and energy efficiency only new construction can deliver. Inside, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and private bath, plus two additional full bathrooms—plenty of space for guests, or a growing household. The open-concept kitchen will shine with granite countertops, stainless steel appliances, and flows right into the formal dining room for easy entertaining. This home will be built with Energy Star-rated systems, a separate hot-water storage tank, and high-quality materials throughout. You’ll also get a full basement with customization potential and a scenic south-facing backyard that’s perfect for relaxing or creating your own outdoor retreat. Located in the Smithtown School District and close to parks, shopping, and transportation—it checks every box for modern living. Now’s the time to secure your future in a brand-new, energy-efficient home in a prime Long Island location. Ask about our Builder Incentives

122 4th Street, Saint James

$2,476,666
7 Beds 7 Baths 885277 MLS
HUGE PRICE REDUCTION OF $223,000! SELLERS ARE MOTIVATED! Make this home yours today! 9 Swan Place is a renovated estate offering over 8,300 square feet of luxurious living space in one of Long Island’s most coveted areas. Nestled in a pristine area, just across from Stony Brook Harbor, this private sanctuary embodies the best of North Shore living. The home is surrounded by the charm of Nissequogue, Smithtown, Head of the Harbor, and Stony Brook. Imagine days spent exploring local beaches, enjoying waterfront activities, or unwinding at nearby fine dining establishments, vineyards and local parks. For boating enthusiasts, this lifestyle is a dream come true. This elegant home features 7 spacious bedrooms and 6.5 baths, including 5 newly updated bathrooms in marble and quartz. The sprawling first-floor primary suite is a true retreat, boasting his-and-hers walk-in closets, a marble fireplace-accented sitting room, and a spa-like marble bathroom with a hot tub just steps away on your private deck. Two additional bedrooms and a full bath on the main floor make this home ideal for multigenerational living. Vaulted ceilings and natural light define the expansive great room, sunroom, and chef’s kitchen, complete with premium stainless steel appliances, a granite-topped island, and updated light wood cabinetry. The sunroom’s new French doors lead to a sprawling 3,000 sq. ft. deck, perfect for entertaining or simply soaking in your serene surroundings. Outside, the 2-acre professionally landscaped property offers resort-style amenities: a heated gunite pool with three waterfalls, a fire pit, volleyball court, stone patio, and an outdoor kitchen. Whether hosting or relaxing, this home has it all. RECENTLY RENOVATED: KITCHEN CABINETS, BATHROOMS, ENTERTAINMENT ROOM, HVAC, HARDWOOD FLOORS, LANDSCAPING, POOL & DECKS. Located in the sought-after Smithtown School District and surrounded by the vibrant lifestyle of the North Shore, this home is the epitome of luxury and comfort. Hidden halfway between NYC and The Hamptons, this glorious home is meticulously renovated while overflowing with natural light. Don’t miss the chance to make it yours.

9 Swan Place, Nissequogue

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.