481 houses for sale in Head of the Harbor

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome to 376 Moriches Road in St. James, where small-town charm, North Shore convenience, and everyday comfort come together. St. James is known for its welcoming atmosphere, local restaurants, parks, beaches, shopping, rail access, and its close proximity to Stony Brook University, Stony Brook Hospital, Smith Haven Mall, and the Smithtown School District. This three-bedroom, two-bath ranch offers easy one-level living with hardwood floors, an eat-in kitchen with stainless steel appliances, bay windows in the kitchen and living room, Laundry on the main level just off the kitchen, and a full, partially finished basement that provides flexible space for a den, home office, gym, playroom, media room, guest area, or storage. Out back, the private fenced yard opens the door to a whole new level of everyday living. Picture summer barbecues, morning coffee on the patio, a fire pit area, garden beds, play space, room for pets, or even creating your own outdoor lounge where friends and famil

A Rare Historic Colonial Rich in History, Charm & Timeless Character! Dating back to 1790, this remarkable 12-room Colonial offers a rare opportunity to own a piece of history. Formerly owned by Adam Smith, a descendant of Richard the Bull Smith, this distinguished residence is set on 1.55 acres of level, picturesque property featuring an in-ground pool. Rich in original architectural details, the spacious home welcomes you through a formal entry into a gracious living room featuring a wood-beamed ceiling, wide-plank wood floors, and an open-hearth fireplace with a beautifully paneled mantel, flanked by built-in bookcases. Just off the living room, a sun-filled Florida room provides the perfect retreat, complete with a beamed ceiling and slate flooring. The formal dining room, accented by elegant shadow-box moldings, is ideal for entertaining and holiday gatherings. The generously sized center-island kitchen offers an inviting breakfast area and opens to a cozy den with its own firepla

Two distinct living spaces, one extraordinary property! Tucked down a long, private driveway off of Carrie Court, this home offers 4,198 square feet of living space in the Smithtown School District. The spacious main home and attached second living area each have a separate entrance and driveway, providing generous parking and a flexible layout. Real wood cedar siding, mature landscaping, raised stone flower beds, and custom wood entry details make a memorable first impression. Inside the main home, hardwood floors, crown and door molding, recessed lighting, and skylights set the tone. The formal living room features soaring vaulted ceilings and a dramatic three-sided stone wood-burning fireplace. The chef’s kitchen pairs deep espresso-toned Shaker cabinetry with white upper cabinets, glass-front accents, granite countertops, under-cabinet lighting, stainless steel appliances, a Viking gas cooktop, double ovens, dishwasher, built-in microwave, oversized stainless steel double sink, sep

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 private 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 ligh

Location location location*. Nestled in the heart of the desirable Saint James, this brand-new luxury construction offers the perfect blend of North Shore charm, history, and convenience. This beautifully designed 4-bedroom, 3-bath home boasts high-end finishes, including a chef’s kitchen with a center island, a stone fireplace, luxury chandeliers, wide plank white oak flooring, thoughtful craftsmanship, and modern living throughout. Set within a private, tucked-away neighborhood with only two points of access, this exceptional residence provides a sense of privacy while still being close to the Village of Head of the Harbor and all that St. James has to offer. The inviting front porch, spacious interiors, and full basement with tremendous potential make this home truly special. An attached two-car garage with direct interior access adds to its convenience. Outdoor spaces are equally impressive, featuring a patio, professionally designed landscape beds, and a beautifully constructed re

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Privacy and serenity awaits you. This home is nestled on 2 acres in the heart of Nissequogue. The main floor boasts an entry Foyer, formal Living room w/cathedral ceilings, formal dining room, eat in kitchen with ss appliances and wine cooler. Family room/den has open floor plan and wood burning fireplace. Brand new 1/2 bath and hardwood flooring throughout. The second floor has a stunning primary bedroom with walk in closet, wood burning fireplace, new bamboo flooring, and Full Bath. In addition there is a bedroom, loft, laundry and full bath. Hardwood flooring throughout. The lower level has a walkout, storage, entrance to 2 car garage, 2 bedrooms, and office/Playroom with possibilities of multi generational living. The outdoor space is a resort like setting. Multi level decking and pool area are perfect for outdoor entertaining! The pool is a salt water in ground pool which was updated in 2020 with new liner, filter, pavers and Trex decking. Recent improvements include, new roof, gu

Don't miss out on this unique, fully updated 3-bedroom 2-full bath ranch property in the heart of Smithtown! Located on a private country lane, the landscaping and overall curb appeal of this property makes heads turn! Positioned only a few hundred yards from Main Street, you'll enjoy accessability to shops, eateries, the library, and Smithtown Historical Society grounds without even starting your car. Whether you are enjoying morning coffee made at your custom coffee station, or entertaining friends while preparing a meal in your outdoor kitchen, this home is made for relaxing and sharing good times with the people most important to you. For added convenience, you'll find the Smithtown train station to NYC only 1 mile away, Stony Brook University 5 miles, and pristine beaches only a 10 minute drive

It's the best of both worlds! Enjoy The Convenience Of A First-Floor Primary Suite With All The Room And Versatility Of A Spacious 5-Bedroom Colonial! Designed For Everyday Living And Entertaining, The Generously Sized Kitchen Offers Abundant Cabinetry, Along With An Inviting Eat-In Breakfast Area That Flows Into A Large Living Room/Great Room. First-Floor Laundry And Convenient Garage Access Add To The Home's Functionality While A Main-Level Office Offers The Perfect Work-From-Home Setup Or Flexibility As A Possible 6th Bedroom. The Second Floor Also Features Three Additional Bedrooms And A Full Bath – There’s Room For Everyone! This Beautiful Home, Set On A Shy Half-Acre, Features A Large In-Ground Pool, Creating The Perfect Setting For Summer Gatherings And Relaxing Weekends. Located In The Desirable Smithtown School District, This Home Offers An Appealing Combination Of Space, Flexibility, And Outdoor Enjoyment. Don't Miss The Opportunity To Make This Wonderful Home Yours!

Sun-filled living spaces, distinctive character and a thoughtfully designed backyard come together at 20 Buccaneer Lane. Set on approximately 0.52 acres in East Setauket's Three Village School District, this 4-bedroom, 2.5-bath home offers approximately 2,661 square feet living space, a covered front porch, established landscaping, an updated driveway and a distinctive carriage-style architectural roof. Hardwood floors, rich wood trim and Andersen windows complement the home's inviting character. The expansive great room features 10-foot ceilings, two skylights, oversized windows and glass doors connecting the interior to the outdoors. A separate family room with a brick fireplace and a formal dining room provide additional gathering spaces. Four bedrooms include distinctive built-in eave storage in upstairs rooms, while windowed bathrooms feature marble finishes. The eat-in kitchen offers wood cabinetry, granite countertops, a tile backsplash, sensor-operated faucets and a commercial-

Your Own Private Retreat in Stony Brook's Desirable Soundview Community! Discover the possibilities of this sprawling, expanded ranch, beautifully situated on over an acre of property offering space, privacy, and an exceptional resort-style lifestyle. Designed for both everyday living and unforgettable entertaining, this expansive home features a full walk-out basement and a seamless connection to the incredible outdoor amenities. Spend summer days relaxing beside the updated in-ground pool, entertain guests at the pool house, gather around the fire pit under the stars, or enjoy the sprawling grounds complete with a dedicated playground area. Whether hosting lively celebrations or savoring peaceful afternoons, this backyard offers something for everyone! Adding to its appeal are coveted Soundview water rights, providing access to the natural beauty and coastal lifestyle of Long Island's North Shore. With its generous footprint, versatile layout, expansive grounds, and outstanding recre

Set on a quiet street in Poquott Village, this adorable two-bedroom cottage offers a welcoming place to call home in a waterfront community. Life here extends beyond your front door. Poquott’s village amenities include private beaches, a community dock, deep-water mooring, parks, a playground, tennis, and gardens, along with year-round community events and private security. Spend an afternoon by the water, enjoy a game of tennis, or connect with neighbors at a village gathering. Cedar shake siding lends classic character, while recent improvements include a brand new roof and boiler, a newer washer and dryer, and an updated electrical panel. Walk along Setauket Harbor on your way to Se-Port for lunch or Elaine’s for cocktails and dinner, with nearby Port Jefferson Village offering shops, dining, a farmers market, entertainment, and the ferry to New England. A cottage with character, thoughtful updates, and a setting that makes it easy to enjoy this corner of the North Shore

A stony brook lifestyle, reimagined. Some homes offer beautiful spaces. Others offer a way of life. This beautifully updated 4 bedroom, 2.5 bath Stony Brook residence offers both along with access to the water through the private 40 Acres Beach Association. Thoughtfully enhanced, the home features a fully renovated kitchen, updated primary bathroom, mudroom, office, mini-split systems, and 12-zone in-ground sprinklers. Significant 2019 improvements include the roof, hot water heater, oil tank, cesspool, and several windows—offering the ease and confidence of a home that has been thoughtfully cared for. Set on over half an acre of beautiful grounds, the outdoor spaces feel like a natural extension of the home with the fenced-in deck with pavilion and separate patio area with a fire pit. Beyond the home itself is a lifestyle that makes this location truly special. Association membership provides access to West Meadow Creek, along with private kayak storage for effortless days on the wate

Welcome to 52 West Meadow Rd where comfort, style and location come together beautifully. A semi-circular driveway welcome's you to this exceptional property, along with professionally landscaped grounds offering a peaceful, resort-like atmosphere. Step inside to a dramatic foyer with soaring ceilings, providing an abundance of natural light. The open concept kitchen and family room seamless connect to the outdoor living spaces, creating a setting for both relaxing and entertaining. Main floor level features an eat-in-kitchen, family room, formal dining room or flexible office space, a formal living room with gas fireplace and laundry room. Three generously sized bedrooms and full bath complete this well-appointed main level. The spacious primary suite provides a serene private retreat with a stunning updated en-suite bathroom delivering a spa-like experience with radiant heat floors and a steam shower. Need more room to spread out? The Finished lower level offers versatility with a fu

An address worth saying yes to! There are certain streets that make you slow down before you ever reach the house. Swan Place is one of them. Tucked within the coveted Village of Nissequogue, the approach winds past estate-like homes beneath a canopy of mature trees, quietly setting the tone for what awaits. Set on two naturally beautiful and private acres, this is a home with presence, but also one that feels remarkably warm once inside. The sense of occasion begins the moment you step inside. A dramatic two-story foyer is anchored by a grand curved staircase, its sweeping wood balustrade gracefully arcing above the entry and continuing into an elevated, bridge like balcony overlooking the marble floor below. Beyond, the home opens to a spectacular two to three story Great Room, where soaring ceilings, architectural detail and walls of natural light create a space that feels impressive yet inviting. It is a beautiful first impression, sophisticated in design, and unmistakably special.

A Hidden Retreat Where Nature, Comfort and Modern Luxury Come Together! Imagine coming home to your own peaceful escape, tucked back from the road and surrounded by the beauty and tranquility of a wooded setting. This extraordinary 3 bedroom, 2 full bath ranch offers something truly special. The warmth and charm of a rustic retreat combined with the sophistication of a beautifully renovated home. From the moment you enter, you'll appreciate the thoughtful details, beautiful hardwood floors, and inviting atmosphere that makes this home so unique. Extensively renovated in 2021/2022, nearly every corner has been transformed with quality craftsmanship and carefully selected finishes. The heart of the home is undoubtedly the spectacular chefs kitchen. A space where beauty and function come together effortlessly. Stunning quartzite countertops, a marble backsplash, porcelain tile floors, and a generous center island with prep sink create the perfect setting for everything from quiet morning

Beautifully renovated from top to bottom in 2026, this 4-bedroom, 2.5-bath home offers a rare combination of modern luxury, timeless character, and a wonderfully private setting on. 95 acres, tucked back on Old Field Road. The thoughtfully designed first floor features a stunning primary suite with a luxurious marble-tiled shower, a walk-in closet, and two additional closets. A dedicated laundry room with first floor laundry and mudroom create a functional entrance in the back of the house. A warm and inviting living room centered around a wood-burning fireplace with a custom mantle connects to the formal dining room and a sunroom providing an effortless connection to the outdoors and brick patio—perfect for morning coffee, casual gatherings, or entertaining. Freshly painted interiors and newly refinished beautiful hardwood floors create a timeless backdrop throughout the home. The custom kitchen features white shaker cabinetry, quartz countertops with a large island to accommodate ext

Welcome to this rare, custom-designed Raised Ranch offering complete modern luxury in Setauket-East Setauket! Located in the top-rated Three Village Central School District, this magnificent 4-bedroom, 3-bathroom home is fully renovated from top to bottom, delivering flawless craftsmanship, modern design, and high-end finishes throughout. Step inside to an expansive open-concept living area featuring rich hardwood floors, warm wood accent paneling, modern globe pendant light fixtures, and a statement fireplace wrapped in custom tile. The designer chef's kitchen features waterfall quartz countertops, under-cabinet/under-island LED lighting, clean white shaker cabinetry paired with custom wood island cabinetry, stainless steel appliances, a farmhouse sink, and a tiled backsplash. Each of the three luxurious full bathrooms is styled with custom tiled finishes, modern matte black hardware, wood vanities, rainfall shower heads, and back-lit LED mirrors. Enjoy complete peace of mind with maj

This Yablonski Built Home is Located In The Village of Nissequogue and is Nice Center Hall Colonial with Some Renovations, (Kitchen) Done 5 years ago. The Foyer Floor is Original Parquet and the Banister Leading up The Stairs is Quite Impressive. There are 4 Large Bedrooms, Primary Has its Own En-Suite and a Walk In Closet. All Located on the second Floor. There is Also A Half Bath Up There as Well. A Large Kitchen with Tons of Storage and a Sit Down Island and The Perfect Banquet Bar with a Sink and Eating Area with a Fireplace, Where a Wall of Windows Fill The Room With Light. There is Also a Large Dining Room For Gatherings. The Extra Large Living Room Has Many Windows as Well, it Also Has a Window Seat For Curling Up and Reading a Book, Here is Where you Will Find Another Fireplace. To Top it Off The Original Hardwood Floors are Still in Perfect Condition. There is a Large Full Basement That is Unfinished That Can Be Accessed From Inside The Home and The Garage. There are 2 Acres T

Welcome to 22 Gemini Lane, Nesconset — An Incredible Expanded Ranch on a Beautiful Property! *. This custom home is much larger than you can imagine, offering extensive living space, multiple additions, and numerous updates throughout. Set on a picturesque tree-lined property, the home welcomes you through a spacious foyer that leads into a thoughtfully designed interior. The oversized kitchen is truly the heart of the home, featuring high-end cabinetry, upgraded appliances, abundant storage, and a convenient laundry area just off the kitchen. The adjoining breakfast area is the perfect spot to enjoy your morning coffee and start the day. The private, expanded primary bedroom offers a peaceful retreat with double closets and a beautifully appointed en-suite bath. Multiple skylights throughout the home fill the living spaces with wonderful natural light. Enjoy every season in the spacious all-season room — perfect for relaxing, entertaining, or gathering around the table for board games

Huge Splanch in Convenient location. 4-5 Bedrooms 4 baths. Front and rear drives. Side road access. Close to Stores Schools and LIRR

One level living at its best! This is the spacious, move in ready LARGE RANCH you have be waiting for! A true 4 bedroom, 2 1/2 bath, with hardwood floors throughout and laundry all on one floor! Finished Heated 2-car garage. Full finished basement. Den with Pellet insert fireplace. Spacious Eat in Kitchen. Beautiful flat backyard that is great for entertaining. New roof. Newer appliances, New driveway. Central Air. Generator. This home truly is not one to miss!