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$1,349,000
5 Beds ⋅ 4 Baths ⋅ 1045111 MLS
Move right into this extended, sprawling 6 BR, 4BA ranch, located in highly desired Mills Pond Estates offering an incredible "in-law" space rarely found in the neighborhood. This open concept home, which boasts hardwood floors throughout the main part of the home, is flooded with natural sunlight and is ideal for entertaining. The principle rooms are spacious, open and airy and overlook the resort-style yard which has an IG heated pool with updated liner, (2026) pump, (2025) and filter (2024), as well as a sports court, outdoor kitchen and built-in firepit. Amazing and rare basement allows for additional living space (with proper permits) or storage. This extended model has a classic brick exterior, designated home office, spacious laundry and functional mudroom spaces you wont find in elsewhere. Natural gas hooked up to the home, just needs to be connected. Current heating system can be converted to gas. Some windows redone 2025 and 2026. Oversized garage. 300 amp service. Solar panels are leased and allow for very low electric bills. Don't miss this truly unique opportunity!

9 Elderwood Drive, Saint James
$839,999
4 Beds ⋅ 3 Baths ⋅ 1043611 MLS
Welcome to 163 South Plaisted Avenue in Hauppauge, a beautifully maintained Hi-Ranch offering comfortable, spacious living and a private resort-style backyard retreat. The main level features gleaming hardwood floors, recessed lighting, generous living and dining areas, and a bright eat-in kitchen with direct access to the expansive Trex deck overlooking the backyard. The updated main hall bath was renovated in 2020. The lower level provides additional living and entertaining space with attractive laminate flooring and a striking gas fireplace, along with a beautifully renovated bath completed in 2023. Step outside and discover your own private oasis. Surrounded by mature privacy trees, the backyard showcases a heated in-ground pool, expansive paver patio, manicured lawn, in-ground sprinklers, and an elevated Trex deck—an exceptional setting for entertaining, dining outdoors, or simply relaxing poolside. Additional highlights include a Navien gas heating system, central air conditioning, Generac standby generator, ADT security system, two-car attached garage, and LiftMaster automatic garage doors. Ideally located within the Smithtown School District, this meticulously cared-for home combines indoor comfort, valuable upgrades, and outstanding outdoor living in one exceptional Hauppauge property.

163 S Plaisted Avenue, Hauppauge
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 1050030 MLS
Set on one serene, private acre surrounded by beautifully landscaped grounds, this distinctive four-bedroom, two-and-a-half-bath residence blends warmth, character and craftsmanship with modern comfort and efficiency. Rich architectural details include hardwood floors, custom millwork, exposed beams and coffered ceilings. The expansive kitchen features custom cabinetry, granite countertops, a center island, professional-style appliances, propane gas cooking and radiant heated floors. The primary suite offers a sitting room, two walk-in closets and a spa-like bathroom. Significant upgrades include high-efficiency heat pump heating and central air, a hybrid heat-pump water heater, whole-house insulation, water filtration and air-purification systems, extensive LED lighting and a generator. A family room with brick fireplace, two-car garage and partially finished basement with a separate heating zone and ample storage complete the interior. Outside, enjoy an in-ground gunite pool, deck, bluestone walkway, seven-zone WiFi sprinkler system, front porch and mature gardens.

4 Salt Hay Way, Smithtown
$899,000
4 Beds ⋅ 3 Baths ⋅ 1048941 MLS
Welcome to 17 White Cliff Lane, a picture-perfect four-bedroom, two-and-a-half-bath splanch offering move-in ready living in desirable Dover Hill Estates. Situated in the Smithtown Central School District, this home boasts tremendous curb appeal with a spacious front yard, mature landscaping, new siding (2024), and updated bedroom windows (2024). Inside, the main living spaces flow together through wide, open doorways. The foyer and formal dining room showcase board-and-batten accent walls, complemented by beautiful wood stair railings. The heart of the home features an inviting eat-in kitchen finished with granite countertops and stainless steel appliances opening to a cozy den with a wood-burning fireplace and views of the backyard garden. Everyday comfort is assured with central air conditioning installed in 2023, along with an updated heating system and oil burner. Practical convenience continues with a partial basement, easy-access attic storage, and a two-car garage. The fully fenced, private quarter-acre backyard is an outdoor sanctuary, complete with an updated irrigation system and an in-ground fiberglass swimming pool featuring a brand-new Loop-Loc cover (2024). With the rear property line bordering a forested recharge basin, the property enjoys added privacy and nature while entertaining or relaxing. Positioned just minutes from the Smith Haven Mall and multiple grocery options, this turnkey home balances peaceful suburban living with everyday convenience.

17 White Cliff Lane, Nesconset
$1,199,000
5 Beds ⋅ 4 Baths ⋅ 1049096 MLS
Welcome to this beautiful & Spacious 5 Bedroom Colonial, ideally situated on a cul de sac & offering 3301Sq Ft of living space ,not including the full basement. From the moment you enter you will appriciate the generous room sizes, beautiful oak floors and the comfortable flow throughout this impressive home. The granite Kitchen is designed for both everyday living and entertaining featuring a center island,ample cabinetry,and a covienient butlers pantry. A warm inviting wood burning fireplace creates a perfect setting for relaxing evenings at home. Step outside and discover your own private backyard oasis. Enjoy the oversized paver patio, perfect for outdoor dining and entertaining overlooking the beautiful heated saltwater inground pool. The basement provides valuble additional space and features an outside entrance offering endless possibilties. With aprroximately 3301 sq ft of living space, a Cul de sac location, this home offers the space,comfort and lifestyle you have been looking for !

5 Keystone Court, Smithtown
$3,575,000
6 Beds ⋅ 7 Baths ⋅ 1048898 MLS
Nestled on two private acres in the Incorporated Village of Nissequogue, this extraordinary estate offers beautifully reimagined living space where luxury, comfort, and timeless design come together. The home underwent a remarkable architectural transformation, completely reimagining the interior and exterior while preserving the character and presence of an established North Shore estate. Every detail was thoughtfully redesigned with an emphasis on exceptional craftsmanship, modern functionality, and elegant living. Rich white oak floors, custom stone surfaces, and exquisite finishes create an atmosphere that is both sophisticated and inviting. Designed for everyday living and exceptional entertaining, the chef’s kitchen features an expansive custom pantry that functions like a second kitchen, built-in wine storage, and a beautifully appointed wet bar. The dramatic great room, highlighted by soaring ceilings and a gas fireplace, serves as the heart of the home, while a separate entertainment room featuring a wood-burning fireplace with easy access to convert to gas provides additional space for gathering and celebrating. Offering six bedrooms and seven baths, including two luxurious suite options with spa-inspired baths, heated floors, generous walk-in closets, and refined finishes, the home provides exceptional flexibility and comfort. A distinctive spiral staircase leads to a charming tower overlooking the estate, creating a truly unique architectural feature. Beautifully integrated infrastructure and modern systems complement the home’s exceptional design, providing the comfort, efficiency, and functionality expected in a residence of this caliber. Outside, a heated saltwater pool with stadium steps and bench seating is surrounded by an expansive paver patio, creating the perfect setting for outdoor entertaining. Mature trees and thoughtfully designed landscaping enhance the privacy and beauty of the level two-acre property. A grandfathered horseshoe driveway with dual Belgian block entrances welcomes you home, a highly sought-after feature in Nissequogue’s renowned horse country. Located less than a mile from two beaches, including one with deeded access, this exceptional property offers a rare opportunity to enjoy luxury North Shore living in one of Long Island’s most renowned communities.

523 Long Beach Road, Nissequogue
$979,000
4 Beds ⋅ 3 Baths ⋅ 1042512 MLS
Welcome to this stunning 4-bedroom, 2.5-bath Colonial, thoughtfully transformed from a Splanch in 2009. Set on a private, meticulously landscaped 1-acre property, this exceptional home offers a perfect blend of classic elegance, modern updates, and resort-style outdoor living. A stone-edged driveway and walkway create a beautiful first impression. Step through the front door into an inviting open foyer, where natural light, rich hardwood floors, and elegant design create an immediate sense of warmth and sophistication. High-hat lighting throughout the home enhances the bright, welcoming atmosphere. The heart of the home is the custom-designed kitchen, featuring quartz countertops and stainless-steel appliances. Conveniently located just off the kitchen are a half bath, laundry area, and an exit leading directly to the spectacular outdoor oasis. The raised formal living room overlooks the den and features a wood-burning fireplace with a removable electric insert, creating a warm and inviting space for relaxing or entertaining. Upstairs, the spacious primary bedroom has been thoughtfully updated and features a luxurious en-suite bathroom, a generous walk-in closet, radiant-heated flooring, and pull-down attic stairs providing convenient storage. The additional three bedrooms offer ample storage, including double closets in each room. Two of the top-floor bedrooms feature beautiful cathedral ceilings. The upstairs hallway includes a walk-in closet and an additional linen closet, providing exceptional storage throughout the home. An updated hall bathroom features quartz countertops, a double vanity, and radiant-heated flooring, combining style and comfort. The fully finished partial basement offers additional living or recreational space, along with enclosed closets for the burner and water tank. During the 2009 renovation, the home was converted to gas-fired hot-water heat. The backyard is truly an entertainer’s and swimmer’s dream, highlighted by a 25-yard official short-course, heated, in-ground saltwater pool, perfect for swimming, relaxing, entertaining, or enjoying your own private resort-like retreat. The beautifully landscaped grounds feature a 13-zone irrigation system and are backed by a private quarter-acre wooded area, creating a peaceful and secluded setting. This exceptional property offers space, style, privacy, abundant storage, and beautifully maintained grounds, along with thoughtful updates throughout. A rare opportunity to enjoy Colonial charm, modern amenities, and an extraordinary outdoor lifestyle all in one.

129 Jefferson Avenue, Saint James
$855,000
4 Beds ⋅ 3 Baths ⋅ 1047477 MLS
Welcome to this beautifully appointed 4-bedroom, 2.5-bath Colonial, ideally situated in the highly desirable Royal Woods/Hillside neighborhood and within the acclaimed Smithtown School District. Freshly painted throughout, this inviting home offers a bright, move-in-ready feel from the moment you arrive. Sun-filled interiors showcase beautiful hardwood floors, cathedral ceiling, a charming bay window, and skylights that create an airy and welcoming atmosphere throughout the home. The spacious living area is anchored by a stunning floor-to-ceiling, full-wall granite wood-burning fireplace, creating an impressive focal point that brings warmth, character, and timeless elegance to the space. The well-appointed kitchen features stainless steel appliances just three years old, combining modern convenience with functionality. The spacious primary suite offers a private retreat, complete with a walk-in cedar closet and a full bath. Enjoy year-round comfort with a high-efficiency heat pump installed just one year ago, providing reliable heating and cooling. An oil-fired hot water heating system remains available as an additional heating option. Step outside and discover your own backyard sanctuary. The inviting inground pool features a one-year-old liner, steps, and pump, while the expansive stone-paver patio provides the perfect backdrop for outdoor entertainment, summer gatherings, or simply relaxing in your own peaceful outdoor escape. Ideally located near Smithtown beaches and Smithtown Landing Golf & Country Club, this exceptional home offers a wonderful combination of comfort, style, convenience, and lifestyle. With its spacious interiors, beautiful outdoor setting, and prime location, this is an opportunity not to be missed. Come make this special home your own!

22 Sheryl Crescent, Smithtown
$2,448,000
7 Beds ⋅ 7 Baths ⋅ 1047513 MLS
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. It is a grand introduction, but one that still feels wonderfully livable, the kind of entrance that reminds you immediately that this is no ordinary home. The kitchen was designed for the way a home like this is meant to be enjoyed, open, welcoming, and always connected to what is happening around it. An impressive, oversized center island anchors the space, surrounded by recently renovated designer cabinetry and premium appliances, with plenty of room for everything from morning coffee to a house full of guests. Completely open to the soaring great room on one side and the spectacular, glass filled sunroom, the kitchen becomes the natural gathering place of the home. Sunlight pours in from every direction, while expansive views of the property create an effortless flow from cooking to conversation to the outdoors beyond. Privately positioned on the first floor, the primary suite feels like a retreat of its own. Generous yet intimate, it features a fireside sitting room, beautifully designed dressing spaces and a spa inspired marble bath. French doors open to a private deck with the hot tub just steps away, a wonderfully peaceful escape any time of the day. Additional rooms on the main level offer wonderful flexibility easily imagined as guest quarters, an au pair suite, private offices, or whatever life happens to require. The upper levels unfold with a wonderful sense of privacy and possibility, offering four beautifully proportioned guest bedrooms along with two additional lounging spaces, perfect for quiet reading, late night conversation, a media retreat or simply giving family and guests a place of their own. But the best surprise is found one level higher on the rooftop deck, where the treetops open to spectacular views toward the harbor and Long Island Sound. It is the kind of unexpected perch made for morning coffee, an evening glass of wine, or simply watching the sky change at the end of the day. Outside is where this property becomes something incredibly special. The grounds feel more like a private retreat than a backyard. A heated Gunite pool, framed in stone and brought to life by three cascading waterfalls, creates a wonderfully serene, spa like setting. Expansive decking, a hot tub, outdoor kitchen and two acres of mature landscape provide plenty of places to entertain, and just as many places to disappear with a book and enjoy the quiet. Then there are the unexpected spaces. A tucked-away bonus room above the three-car garage feels like a hidden discovery within the home, an ideal private lounge, game room, studio, or escape, complete with its own Juliet balcony. Life in Nissequogue has always been about having room to breathe. Beaches, boating, the harbor, parks, and the villages of the North Shore are all part of everyday life here, while New York City and the Hamptons remain within reach. 9 Swan Place is an address worth seeing. WHEN THE HOUSE, THE SETTING & THE VALUE ALL SAY YES

9 Swan Place, Nissequogue
$1,249,999
5 Beds ⋅ 4 Baths ⋅ 1048499 MLS
Your resort style paradise you have been waiting for has finally come to market!!! Welcome to 3 Saggese Lane in Nesconset. Tucked away on an oversized cul-de-sac, this beautifully updated 5-bedroom home offers the perfect blend of luxury, comfort, and resort-style living. Inside, enjoy a brand-new kitchen, new flooring throughout, a spacious den with fireplace, mudroom, and an impressive primary suite with walk-in closet and spa-like bath. The partially finished basement adds a BONUS room and another full bath for even more living space. Step outside and experience a true backyard oasis featuring a bi-level yard, lighted waterfall, saltwater in-ground pool surrounded by pavers, outdoor kitchen, fire pit area, and lush landscaping—an entertainer’s dream! Additional upgrades include updated cesspools, central air, PVC fencing, generator hookup, Andersen windows, and a shed with electric. A one-of-a-kind home that feels like a vacation every day! All being within the award winning Smithtown schools. This one will not last!!!

3 Saggese Lane, Nesconset
$1,350,000
3 Beds ⋅ 2 Baths ⋅ 1048649 MLS
Welcome to a truly extraordinary St. James residence where timeless elegance meets modern luxury. This stunning 3-bedroom, 2-bath ranch has been meticulously transformed from the ground up, creating a home that feels brand new while offering the warmth, character and comfort of an established property. Every inch has been thoughtfully renovated and no detail has been overlooked. From the moment you arrive, the quality and craftsmanship are evident. The home features a new roof, windows, interior and exterior doors, skylights, siding, trim, gutters, driveway and extensive new brickwork. New insulation, 200-amp electric service, HVAC, buried electrical lines and new cesspools provide peace of mind, while a whole-house generator adds another level of convenience. Inside, every space has been beautifully reimagined with new wood flooring, custom closets, plantation shutters and exceptional trim work throughout. The walls and ceilings have been completely redone, creating a pristine backdrop for the home’s luxurious finishes. The gourmet kitchen features premium Wolf and Sub-Zero appliances, Bosch dishwasher and exquisite quartzite countertops, with granite surfaces throughout the remaining areas. The renovated bathrooms offer a spa-like experience, with the primary bath showcasing porcelain tile, a stunning marble shower and heated floors. Technology and convenience are seamlessly incorporated with central vacuum, including a garage connection, whole-home network system with WiFi extenders in the attic, 15-zone IGS system and brand-new washer and dryer. The basement includes a dedicated home gym with its own AC and heat and WiFi readiness. But the true showstopper awaits outside. Step into your own private country club-style retreat featuring a sparkling in-ground pool, tranquil Koi pond, expansive deck and fully equipped outdoor kitchen — the ultimate setting for entertaining, relaxing poolside or enjoying quiet evenings under the stars. The outdoor experience is enhanced by beautiful landscape lighting, extensive brickwork and thoughtfully designed spaces throughout. Pool filter and Koi pond filter have been updated, and the pool heater is approximately four years old. This is a rare opportunity to own a home where the renovation, infrastructure and luxury upgrades have already been completed to an exceptional standard. Truly turnkey. Truly exceptional. And unlike anything else. Welcome home to your own private retreat in the heart of St. James.

7 King Arthurs Court, Saint James
$850,000
4 Beds ⋅ 3 Baths ⋅ 1048431 MLS
Remarkable Custom Built 4 Bedroom, 2.5 Bath Colonial In The Heart Of Saint James. This Classic Residence Has Detailed Architectural Design, Crown Moulding, Mill Work And Elegant Appointments Throughout. Boosting A 2-Story Entry Foyer With Staircase, Formal Dining Room, Formal Living Room with Prominent Gas Fireplace, Family Room With Stone Gas Fireplace, and Siding Glass Doors to Composite Deck. Spacious Eat In Kitchen Complimented With Newer Appliances. Renovated Hall Laundry Area, First Floor Powder Room. Upper Level Includes Primary Bedroom Suite With Vaulted Ceilings, Skylights and His-And-Her Closets, Primary Bath w/ Soaker Tub, Shower and Vanity Counter. All Large Bedrooms with Plush Carpeting and Closet Systems. Upper Level Full Bathroom. All Hardwood Flooring as Seen/Carpet As Seen. Spectacular Fenced Property With Lush Professional Landscape, In-Ground Heated Chlorine Pool. All Composite Decking on Outside Deck, 2 Car Garage and Shed, Valuable Updates Include: 2023 New Roof, Newer Kitchen Appliances, Closets Systems, 2025 Hot Water Heater, Digital Irrigation System, Front Windows Casing Replaced with Azex Trim. Located Close Beaches, Golf Clubs, Renowned Restaurants, Located in the Desirable Smithtown School District.

220 St. James Avenue N, Saint James
$799,000
4 Beds ⋅ 3 Baths ⋅ 1041929 MLS
Welcome to 16 Dogwood Drive, a spacious four-bedroom, 2.5-bath Colonial nestled in the incorporated Village of the Branch. Set on a beautiful .60-acre lot, this home offers a classic Colonial layout, generous living spaces, and wonderful potential to make it truly your own. The main level features a welcoming living room with a wood-burning fireplace, formal dining room, eat-in kitchen, den, and convenient half bath. The spacious layout provides comfortable areas for both everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms with ample closet space, including a primary bedroom with an en-suite full bath, along with an additional full hall bath. The primary bathroom has also been tastefully updated. Thoughtful improvements throughout the home include beautiful wood floors, vinyl siding, a newer cesspool, in-ground sprinkler system, and updated walls with new insulation in most living areas. The inner bedroom walls have also been soundproofed, providing added privacy and peace throughout the home. A full unfinished basement and one-car garage offer plenty of storage and the potential for future living or recreational space. Step outside to your own private backyard oasis, surrounded by mature Leyland cypress that create a peaceful and secluded setting. An in-ground pool and expansive paver-stone patio provide the perfect backdrop for summer relaxation, outdoor entertaining, and making lasting memories. Conveniently located between Smithtown and St. James, this home is close to shopping, restaurants, parks, recreation, and everyday amenities. With its classic Colonial charm, spacious rooms, established landscaping, and numerous updates, 16 Dogwood Drive is the perfect canvas to create the home you’ve always imagined personalized to reflect your own style, vision, and way of living!

16 Dogwood Drive, Smithtown
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 1047851 MLS
Welcome to 29 Farm Road....nestled in the prestigious Village of Head of the Harbor, where secluded, private & tranquil living awaits! This stunning, beautifully maintained Expanded Ranch features a grand entry foyer, spacious EIK w/ granite countertops, center island, SS appliances, and picturesque views of the surrounding landscape, a warm and inviting Great Room w/ Stone FP and vaulted ceilings w/ 2 skylights and 4 slider doors leading to the wrap around deck, a gorgeous formal dining room, powder room. The 1st floor features 3 spacious bedrooms, including a luxurious Primary Bedroom Ensuite w/ private access to the extensive wrap-around porch, WIC, and primary bath w/ double vanity sink, bathtub, and separate shower. Bedroom 2 features a WIC, chair rail molding, and an ensuite bathroom w/ spa tub. Bedroom 3 offers a private loft space and skylight, and a main floor office space w/ French doors, plus an additional full bath completing the main level. The versatile loft is ideal as a recreation room, home gym, or flex space, with convenient attic access. The lower level offers exceptional flexibility and features a 4th Bedroom (perfect for guests or an in-law suite), a Summer Kitchen w/ quartz countertops, oversized family room, 2 separate gym rooms, full bath, laundry room, ample storage, direct access to the two-car garage, and sliders leading to your own private, resort-like backyard retreat! Additional features include.... CAC (2 zones), Oil Heat (4 zones - burner 2016), 200-amp electric, IGS System (8 zones - redone in 2026), inground saltwater heated pool (Liner - 2025), Whole House Inside & Outside KeyOS wireless app-controlled stereo system, and a portable generator with transfer switch hookup. Surrounded by nature, with an abundance of natural light, oversized windows, and skylights that create a bright, airy, and inviting atmosphere throughout. This exceptional home truly has it all! All this and much more... Set on over 2+ acres of beautiful and secluded property (very private), you do not want to miss this rare opportunity!

29 Farm Road, Head Of Harbor
$824,999
3 Beds ⋅ 3 Baths ⋅ 1042862 MLS
Incredible opportunity to own this magnificent oversized Colonial, ideally situated mid-block on an impressive .40 acre property in St. James! The exterior makes an immediate statement with striking architectural presence, an expanded blacktop driveway with Belgian block border, paving-stone walkway, cedar-impression siding, two-car attached garage, and a beautiful paving-stone front porch offering the perfect setting to relax and enjoy the outdoors. The spectacular, fully fenced backyard is built for entertaining and features a two-year-young saltwater in-ground swimming pool surrounded by an enormous sandstone paver patio, multiple defined entertaining areas, and a raised patio that creates additional outdoor living space. Inside, the home offers a bright, open floor plan that has been freshly painted and showcases gorgeous light hardwood flooring throughout the first floor. The stunning chef’s kitchen features custom white cabinetry extending to the ceiling, contrasting black hardware and finishes, quartz countertops, a beautiful glass-tile backsplash, stainless steel appliances including a built-in Sharp microwave, Sharp range, Sharp dishwasher, and LG refrigerator with water and ice dispenser, plus a large center island providing additional prep space, storage, and seating. The spacious eat-in kitchen also features a sliding glass door providing direct access to the incredible backyard. The kitchen flows seamlessly into an enormous den/great room highlighted by recessed lighting and a custom wood-burning fireplace with a dramatic cultured-stone surround, along with a conveniently located powder room. The first floor also offers a generously sized formal dining room flowing into the formal living room, complete with recessed lighting and abundant natural light. Upstairs, the enormous Primary suite features hardwood flooring, a ceiling fan, walk-in closet, and private Primary full bathroom with a glass-enclosed stand-up shower. The additional two bedrooms are spacious and feature hardwood flooring, ceiling fans, and custom molding. The oversized full basement with high ceilings provides tremendous additional potential and includes black stainless steel front-loading washer and dryer. Additional highlights include a one-year-young state-of-the-art forced-air heating and central cooling system, updated 200-amp electrical service with subpanel, two-car attached garage, and Smithtown School District. From the beautifully updated interior to the resort-style backyard and expansive property, this exceptional St. James Colonial offers an incredible combination of space, updates, functionality, and indoor-outdoor living!

282 6th Avenue, Saint James
$2,399,000
6 Beds ⋅ 5 Baths ⋅ 1046808 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 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 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, newer roof and skylights, 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. A must see! *Taxes Include Village Taxes of $3,199

15 The Chase, Head Of Harbor
$850,000
4 Beds ⋅ 3 Baths ⋅ 1044068 MLS
Beautiful Updated Colonial in a Quiet, Friendly Neighborhood This spacious Colonial home features a fully updated kitchen with a center island, seamlessly opening into a generous formal dining room and an airy living room. A warm and inviting family room with a brick fireplace adds charm and comfort, along with a convenient half bath on the main level. A slider door leads out to a large deck overlooking a fully fenced backyard, complete with an inground pool and slide — perfect for summer fun and entertaining. Upstairs, you’ll find the home’s private living spaces, while the property sits on a quiet, friendly, and picturesque street, close to all shopping, major highways, and transit options for easy commuting.

14 Format Lane, Smithtown
$759,000
4 Beds ⋅ 4 Baths ⋅ 1042725 MLS
Welcome to 23 Dale Lane! This well-maintained 4BR, 3.5BA multi-level home on .25 acre offers exceptional versatility for comfortable single-family or multigenerational living. The inviting entrance foyer leads upstairs to the living room, dining room and eat-in kitchen overlooking the lower-level den, featuring a wood-burning fireplace and sliding glass doors to a Trex deck and inviting in-ground pool. A powder room, laundry and utility rooms complete this level. Upstairs features a spacious primary ensuite with walk-in closet, two additional bedrooms and full bath. An open staircase off the entrance foyer leads to the lower level that offers a fourth ensuite bedroom, providing privacy and flexibility for guests or multigenerational living a versatile office, storage and recreation area with cabinetry, sink and private outside entrance. PVC fencing adds privacy. First and Second Level 1957 Sq. Feet and Lower Level with outside entrance 774 Sq. Feet Come see for yourself and fall in love!

23 Dale Lane, Smithtown
$759,900
4 Beds ⋅ 3 Baths ⋅ 1043024 MLS
Welcome to this spacious 4 bedroom with 2.5 baths Raised Ranch offering plenty of room to enjoy. This home boasts beautiful hardwood floors and a wood burning fireplace creating a warm and inviting atmosphere. The home features year-round comfort with gas heating and central A/C. The lower level has additional living space for entertainment with an outside entrance. The garage was converted to additional versatile living space. Step outside to your own backyard retreat featuring a deck and above ground pool which is perfect for relaxing on summer days. Ideally located in close proximity to Gaynor Park, schools, Lake Ave shopping and the train station for your convenience. This is a true dream to call home!

49 McKinley Street, Saint James
$738,000
3 Beds ⋅ 2 Baths ⋅ 1043090 MLS
WARMTH, COMFORT AND CHARM ON .56 ACRE OF MAGNIFICENT PROPERTY WITH LOW LOW TAXES Welcome to this expanded ranch in the sought after Smithtown School District. This home boasts a large, sunlit family room, hardwood floors, 3/4 bedrooms, a separate office/library room, newly renovated kitchen and baths and a large full finish basement with den, nanny's room, full bath, and storage galore, 2yr Burner Washer and Dryer. The oversized shy 2/3 acre property is a true backyard oasis with 1,000 sq ft of paver patios, a fire-pit, gazebo, pool, shed and PVC fencing. There’s also a separate area with outside entrance, perfect for extended family that come to visit. Taxes with Basic Star $10,515 Gas right on corner on Gilbert. Pool as gift

19 Ridgeley Road, Smithtown
$999,000
4 Beds ⋅ 4 Baths ⋅ 1041490 MLS
Great Cul De Sac Setting for this Center Hall Colonial, Spacious Rooms, Large Windows, Hardwood Floors, Hi Hats, Vaulted Bathrooms, Radiant Heat, Full Finished Basement, Refreshing Salt Lagoon Water Heated(Propane) Pool with Hot Tub, Central Vacuum, 200 Amp, Inground Sprinklers-8z, Fireplace and MORE !

11 Raphael Boulevard, Nesconset
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 1041795 MLS
Spacious home on an equestrian estate (Horse property has small barn and tack room.) featuring handcrafted vaulted wood ceilings throughout and refined natural stone detailing. Guest suite with private bath, Situated within a private wooded landscape, surrounded by timeless natural beauty. Beautifully positioned windows frame breathtaking scenic views, with a private barn enjoying panoramic views. Three generous driveways and an impressive circular driveway enhance the estate-like setting. A truly exceptional property offering privacy, natural beauty, and timeless architectural character.

135 Oakside Drive, Smithtown
$1,950,000
4 Beds ⋅ 4 Baths ⋅ 1039294 MLS
Welcome to 38 Riverview Terrace, an exceptional custom-built Colonial offering five bedrooms, three full bathrooms and one half bath, with an extensive array of high end finishes, entertainment spaces and resort-style outdoor amenities. A grand foyer welcomes you with wainscoting, chandelier and stunning maple hardwood flooring that continues throughout the first floor. The main level features an elegant formal dining room and a spacious den anchored by a wood-burning fireplace. The expansive eat-in chef’s kitchen is designed for both cooking and entertaining, featuring a large 7'10" center island, quartz countertops throughout, skylights, a breakfast area and modern farmhouse sink. High-end Sub-Zero and Wolf appliances include an eight-burner Wolf range with double ovens, a massive custom hood with pot filler, an additional wall oven, warming drawer, built-in microwave, ice maker and wine cooler. Radiant heated flooring completes the kitchen. A powder room with radiant heated flooring is conveniently located on the main level for guests, along with a dedicated first-floor laundry room. Upstairs, the spacious primary suite features an impressive custom walk-in closet and spa-inspired bath with a soaking tub, radiant heated flooring and heated towel rack. Four additional bedrooms and beautifully appointed bathrooms provide plenty of space throughout the home. Skylights throughout bring an abundance of natural light into the residence. The finished lower level is designed for recreation and entertainment, offering an expansive recreation area with a wet bar and dedicated media room/home theater with its own home entertainment system. The home is wired for seven televisions, while a Sonos sound system with outdoor speakers extends the entertainment outdoors. The backyard offers private country club style amenities, beginning with a spectacular heated in-ground pool with cascading waterfall surrounded by expansive armortec paving stones. Professionally landscaped grounds and dramatic landscape lighting create a beautiful setting for outdoor entertaining. A fully equipped outdoor kitchen with built-in grill, pergola and pavilion provide additional gathering spaces, while a pickleball court and basketball court offer recreation right at home. An attached two car garage completes this extensively appointed Smithtown residence, offering exceptional indoor and outdoor living with amenities designed for entertaining, recreation and everyday enjoyment.

38 Riverview Terrace, Smithtown
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 1038256 MLS
A Coastal Setting That Makes Every Day Feel Like an Escape. Set on 1.74 beautifully private acres in a private beach community, this distinctive 4-bedroom, 3-bath home captures the relaxed rhythm of coastal living, surrounded by water views and beautiful natural surroundings, with easy access to town beaches and the marina. The property extends to Stony Brook Harbor, creating a peaceful natural backdrop, while mature plantings, gardens and a rare gunite in-ground pool enhance the sense of privacy and connection to the landscape. Inside, a light and bright open floor plan is defined by oversized windows and walls of glass that frame the surrounding beauty and bring nature into nearly every living space. The impressive great room takes full advantage of the setting with a dramatic wall of windows, vaulted ceilings and a stone wood-burning fireplace. Open to the dining room, this inviting space also features sliders to an expansive, updated Trex deck—a wonderful place for outdoor dining, entertaining or simply enjoying the views of Stony Brook Harbor. The spacious eat-in kitchen offers generous counter space, granite countertops, updated stainless steel appliances and a wonderful dinette area overlooking the pool and lush natural property. The primary bedroom suite provides a private retreat with a beautifully appointed ensuite bath featuring tumbled marble, a double vanity with granite counters, Jacuzzi tub and oversized shower with dual shower heads and multiple body sprays. Two additional generously sized bedrooms and a full bath with a custom vanity and granite countertop complete the second floor. Adding exceptional versatility, first-floor guest quarters with a separate private entrance and covered patio features a bedroom, full bathroom and living area, providing a comfortable and private space for guests or additional living space. The finished lower level offers even more room to gather and entertain, with wood floors, a comfortable den, wet bar and separate entry with direct access to the outdoors. Outdoors, the peaceful setting takes center stage. The rare gunite in-ground pool, surrounded by stone patios and complemented by a convenient changing room, creates an inviting place to spend summer days, entertain or simply relax amid the beautiful gardens and natural coastal plantings. Updated vinyl siding, a carport and ample driveway parking add everyday convenience. More than simply a home near the water, this is a property that embraces the character and ease of coastal living. With privacy, harbor views and the natural beauty of its 1.74-acre setting, every season offers another reason to enjoy being here—a coastal retreat that feels wonderfully removed from everyday life.

588 E. Long Beach Road, Nissequogue
$799,990
3 Beds ⋅ 2 Baths ⋅ 1037737 MLS
Welcome to this beautifully impeccably styled turnkey 3-Bedroom, 2- bath home on.23 acres professionally landscaped property with a 16x32 inground pool, gazebo and beautiful stonework patio. This home offers the perfect blend of modern style and effortless living. Thoughtfully updated throughout this sun-drenched home features a bright open layout which flows seamlessly from the living room into the open dining room, and kitchen. Three generous sized bedrooms- including a large primary bedroom with ample closet space and a beautifully updated full hall bath complete the main level. Enjoy the partially finished lower level with new carpeting which provides additional living space and a full bath. Whether you envision outdoor entertaining in your 16x32 inground pool or simply enjoy the privacy in your serene fenced in backyard- this is truly your next home!

116 Shenandoah Boulevard N, Nesconset
$1,649,000
5 Beds ⋅ 4 Baths ⋅ 1037441 MLS
Welcome to this beautiful 5 bedroom 3.5 Bath Colonial perfectly positioned on a quiet cul-de-sac set within Yellow Top Estates, a rare gated enclave of luxury single-family homes. From the covered front porch and beautiful paver and asphalt driveway to the 3-car garage, this home makes an incredible first impression. Enter inside to a dramatic two-story entry foyer with soaring ceilings, beautiful moldings and hardwood floors throughout. The spacious living room features custom built-ins surrounding a gas fireplace, creating the perfect place to gather and relax. The completely renovated kitchen is truly the heart of the home, featuring quartz countertops, a gas range, double ovens, wine fridge and plenty of space for entertaining. A private office or 5th bedroom is perfectly situated away from the main living areas, offering great flexibility for guests or working from home. Upstairs, the spacious primary suite is a true retreat with a beautifully appointed primary bath, including a soaking tub overlooking the backyard. And the backyard is where this home really shines. Designed for resort-style living, it features a freeform saltwater inground pool surrounded by beautiful pavers, an incredible outdoor kitchen with a gas grill, gas pizza oven, granite countertops and an oversized bar ready for summer BBQs and entertaining. A covered Trex deck offers the perfect spot to relax and enjoy the private setting, while a separate hot tub provides the perfect place to unwind and can be enjoyed year-round. Lovingly maintained, thoughtfully updated and ideally located within Yellow Top Estates. Don't miss this special home!

6 Hayloft Court, Smithtown
$589,000
2 Beds ⋅ 3 Baths ⋅ 1033652 MLS
Spectacular Townhouse Nestled in a private setting in "The Woods" Development in Blue Ribbon Smithtown School District features tasteful renovations throughout - A Decorators delight! Spacious living area perfect for entertaining. This Bright Chef's Kitchen with all the upgrades and stainless steel appliances is a show stopper. Formal Dining Room leads to oversized deck for additional entertaining space. Head upstairs to a luxury primary suite oasis complete with separate sitting room, balcony, walk in closets and ensuite. Additional second bedroom perfect for a home office or guest quarters. Amenities include Outdoor Pool, Fitness room/Gym, Tennis, Library, Clubhouse and plenty of activities for all ages. Woof/Meow - pets welcome!........ Amended Special Assessment Based on the finalized loan terms, the amended special assessment will be: • $470 per month per homeowner • Effective: September 1, 2026 • First Payment Due: September 1, 2026 • The assessment will remain in effect through August 2036, consistent with the 10-year loan term.

5 Jeremy Circle, Nesconset
$800,000
4 Beds ⋅ 3 Baths ⋅ 1030391 MLS
Sprawling Smithtown Ranch on .52 Acre with Gunite Pool & 3-Car Garage! Space, flexibility and a backyard built for summer living come together in this distinctive 4-bedroom, 2.5-bath home set on a beautiful .52-acre property in the desirable Smithtown School District. Offering the ease and open feel of ranch-style living with a thoughtfully designed split-level bedroom wing, this home provides an exceptional layout for both everyday living and entertaining. A welcoming foyer opens to generously sized living spaces, including a formal living room, formal dining room, expansive den and a separate home office—ideal for working from home or creating a quiet flex space. The eat-in kitchen features granite countertops, stainless steel appliances and direct access to the deck, backyard and pool, making indoor-outdoor entertaining easy. Just a few steps above the main living area are four bedrooms and two full baths, creating separation and privacy without sacrificing the convenience of a ranch-style layout. The spacious primary suite features walk-in closets and a private bath with a sunken tub. The partially finished basement provides additional flexible space along with plenty of storage. Outside is where this property truly shines. Enjoy more than half an acre with a gunite inground pool and waterfall feature, a spacious deck for outdoor dining and entertaining, and an inground sprinkler system. A circular driveway and rare 3-car attached garage provide abundant parking and storage. Gas heat, central air conditioning and public sewer add to the home's everyday comfort and convenience. If you've been searching for generous living space, a private backyard retreat and an exceptionally versatile layout in the Smithtown School District, 29 Ivy Hill Drive deserves a closer look.

29 Ivy Hill Drive, Smithtown
$799,000
4 Beds ⋅ 2 Baths ⋅ 1029526 MLS
Welcome Home To This Legal Mother Daughter & Beautifully Constructed Nesconset Colonial Nestled On An Expanded Corner Lot In The Award Winning Smithtown School District & It's Original Owner Featuring 4 or 5 Bedrooms, 2 Full Bathrooms, Welcoming Entry Foyer, Eat-In Kitchen w/ 3 Skylights, Granite Countertops & Double Sliders Leading Out To Back Deck, Hardwood Floors Throughout, Central AC, Full Basement w/ Tons Of Storage, New Roof, One Car Attached Garage, In-Ground Sprinklers & A Private Resort-Like Backyard w/ Oversized In-Ground Pool Perfect For Entertaining And/Or Relaxing, Plus Much, Much More! You Do Not Want To Miss This One!

26 Heritage Place S, Nesconset
$2,375,000
5 Beds ⋅ 4 Baths ⋅ 1027926 MLS
Tucked away on two acres at the end of a quiet cul-de-sac, in the prestigious enclave of Head of the Harbor, this magnificent five-bedroom, four-bath estate offers an unparalleled blend of modern luxury and serene privacy. The entire residence has undergone a comprehensive transformation over the past six years, resulting in a home that feels brand new while retaining its sophisticated, timeless character. The heart of the home is the stunning new kitchen, designed with a modern aesthetic that features sleek finishes, built-in Sub-zero refrigerator, Wolf oven, Jenn Air cooktop- with an intuitive layout perfect for both daily living and large-scale hosting. The large center island with seating, waterfall-edge quartz countertop and second sink invites entertaining on a grand scale, or just a perfect intimate gathering. The new picture window provides a panoramic view of the pristine outdoor, resort-like grounds. Off the kitchen, enjoy casual meals in the glass-enclosed dining area. The main floor also features a formal dining room, a bedroom and full bathroom, in addition to the entertaining spaces, which include an expansive family room with fireplace and access to the patio, an adjacent living room, and a bright, open sitting room off the kitchen with floor-to-ceiling windows looking out to the parklike property. Each of the four full bathrooms has been exquisitely renovated with designer fixtures, heater floor in the primary suite, and contemporary tiling, providing a spa-like experience in every corner of the house. The home's electric service has been upgraded to 450 amp in 2022, and also has a whole house natural gas generator, providing comfort along with style across the entire living space! Beyond the interior, the property serves as a private sanctuary. A brand-new patio leads to a sparkling pool with all new equipment installed in 2022, creating an outdoor oasis framed by mature trees and fenced-in expansive greenery across the 2 acre property. You will also find a dining pavilion offering shade and comfort, a bar, and a cabana with a changing area, bath and outdoor shower for added convenience. The commitment to quality is evident in the structural upgrades as well, including a new balcony off of the primary suite, new roof and the addition of owned solar panels for exceptional energy efficiency. The lower level reveals a fully finished basement, offering versatile space including a summer kitchen, new full bathroom, home gym, media room and recreation area. With every detail meticulously addressed—from the expansive living spaces to the secluded acreage—this estate represents a rare opportunity to enjoy a turnkey lifestyle in one of the most sought-after locations on the North Shore. This Head of the Harbor home is surrounded by the charm of Nissequogue, Smithtown, Saint James 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. Note: please see the attached document for a full list of upgrades to this home!

5 Meadow Gate W, Head Of Harbor

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