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$860,000
4 Beds ⋅ 3 Baths ⋅ 1030391 MLS
You must see the amazing layout of this sprawling 4 bedroom, 2 1/2 bath ranch with a separate office, nestled on a beautiful .52-acre property in the desirable Smithtown School District. With the bedrooms just a few steps up from the main living area, it has all the great features of a ranch while providing privacy from the main floor. From the moment you step through the front door, the beautiful foyer sets the tone for the spacious, welcoming feel found throughout. The main level offers wonderful one-floor living, with a formal living room, formal dining room, an expansive den, and a dedicated home office. The eat-in kitchen features granite countertops and stainless appliances with direct access to the deck, backyard and pool area. Just a few steps up, you'll find four comfortable bedrooms and two full baths, including a large primary suite complete with a sunken tub and walk-in closets — a true retreat at the end of the day. A full, partially finished basement adds even more flexible living and storage space. Outside, the backyard is made for entertaining and relaxing alike. Take a dip in the gunite inground pool with a waterfall feature, unwind on the back deck, and enjoy the ease of an inground sprinkler system keeping the grounds lush. A 3-car attached garage and circular driveway offer plenty of room for parking and storage. Gas heat, central air conditioning, and public sewer round out the home's practical comforts. Homes with this much space, on a lot this size, in this location, don't come along often.

29 Ivy Hill Drive, Hauppauge
$899,999
4 Beds ⋅ 2 Baths ⋅ 1028706 MLS
Welcome to 41 Oak Street. This inviting High Ranch offers exceptional curb appeal with stately pillars, shingle style vinyl siding, Fieldstone accents, paver walkways, a charming Arbor enhancing the entrance to the backyard and an oversized Belgian Block lined driveway. The home is surrounded by mature landscaping offering natural privacy and a serene setting. Step inside to discover gleaming hardwood floors, sunlit living spaces enhanced by bay and bow windows, custom hand carved wood detailing and stain glass accents that create a warm inviting ambiance. The beautifully appointed kitchen, expansive den with a large skylight and a tastefully renovated full bathroom further enhance the home’s appeal. The versatile lower level offers excellent potential for extended living with proper permits. The sliding glass doors leads to your own private retreat. Multi-level Trex and wood decking with handcrafted built in benches, tiered wood walkways, a custom awning, tranquil fish pond, and a sparkling 20x40 in ground pool surrounded by stone pavers featuring a new liner complete this thoughtfully designed outdoor space. Additional highlights include a new 275 gallon Roth Oil tank, 200-Amp electrical service, a new first floor central air conditioning system, and a roof and siding that are approximately 10 yrs. old. Conveniently located near Smithtown Beaches, Smithtown Landing Golf and Country Club. All of-this is set on .50 acres in a truly desirable location. Don’t miss this wonderful opportunity to make this home your own and create lasting memories for years to come.

41 Oak Street, 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
$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
$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 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 provides comfort and 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, 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. Note: please see the attached document for a full list of upgrades to this home!

5 Meadow Gate W, Saint James
$949,000
4 Beds ⋅ 4 Baths ⋅ 1020468 MLS
Stunning updated Colonial located in the Smithtown School District. Bright, Open & Inviting! Exceptional Home Combines Elegance and Modern Updates. Resort-style Backyard with Heated Pool. Every Detail has been Thoughtfully Designed for Comfort and Enjoyment! This could be Your New Home!!

8 Robinhood Court, Nesconset
$869,000
4 Beds ⋅ 3 Baths ⋅ 1026666 MLS
Welcome to this exceptional 4-bedroom, 2.5-bath Splanch located in the prestigious East Hill Estates section of Smithtown. Offering approximately 2,380 square feet of beautifully designed living space, this residence seamlessly blends timeless elegance with everyday comfort. A gracious floor plan features sun-filled living areas, a warm and inviting fireplace, spacious formal and casual gathering spaces, and a well-appointed kitchen designed for both entertaining and daily living. The generous primary suite provides a peaceful retreat, while three additional bedrooms offer flexibility for family, guests, or a home office. Enjoy year-round comfort with an updated HVAC system, providing efficient heating and cooling throughout the home. Step outside to your private backyard oasis featuring a heated in-ground salt water swimming pool, expansive patio with gas BBQ connection , and beautifully landscaped grounds—perfect for outdoor entertaining or relaxing all summer long. Additional highlights include an attached two-car garage, a full basement offering abundant storage and future finishing potential, and pride of ownership throughout. Ideally situated in the award-winning Smithtown Central School District, the home is conveniently located near parks, golf courses, shopping, dining, beaches, major parkways, and the Long Island Rail Road. This is a rare opportunity to own a beautifully maintained home in one of Smithtown’s most sought-after neighborhoods, where classic Colonial charm meets modern comfort.

6 Navy Drive, Smithtown
$679,000
3 Beds ⋅ 2 Baths ⋅ 1025884 MLS
Well Maintained Deep Hi Ranch, Hardwood Floors, Updated Windows, Cesspool-6 Years, Oil Tank Above Ground, Spacious Lower Level with 2nd Kitchen, Full Bath and Access to Breathtaking Private Yard- Vacation in Your Own Backyard! Lush Landscape, 16x32 Oval Pool (AG), Built In Barbecue, Stone Patios, Oversized Paver Drive, Paver Walks and Steps; Convenient Location to Everything! Property Taxes with Basic Star $10,096.

82 Sheppard Lane, Nesconset
$849,000
4 Beds ⋅ 2 Baths ⋅ 1023804 MLS
MOTHER DAUGHTER SET UP AND BASEMENT WITH OUTSIDE ENTRANCE! Welcome to this beautifully renovated Saint James home where no expense has been spared. Every detail has been thoughtfully updated, featuring board and batten siding, Andersen windows, and gorgeous hardwood floors throughout. The designer two tone kitchen showcases vanilla and warm brown shaker wood cabinetry, elegant granite countertops, and stainless steel appliances. Both brand new bathrooms have sleek, modern design. Additional upgrades include In ground sprinklers, brand new central air conditioning, new electrical panels for both the house and pool, and a fully finished basement with outside entrance. Step outside to your private backyard oasis featuring a newly updated in ground pool with brand new liner, pump, filter and beautifully landscaped grounds. Ideally located just minutes from Smith Heaven mall, shopping, dining, parks, and major roadways. This home offers both convenience and an exceptional lifestyle. Situated within the highly regarded Smithtown School District! This truly move in ready home delivers luxury finishes, quality craftsmanship, and incredible value.

273 Cambon Avenue, Saint James
$1,890,000
4 Beds ⋅ 4 Baths ⋅ 1022986 MLS
Exceptional custom-built estate nestled on over an acre in one of Kings Park’s most prestigious enclaves. Thoughtfully designed with approx. 4,000 sqft. of elegant living space, this residence blends timeless craftsmanship with modern luxury. From gracious entertaining spaces to beautifully appointed bedrooms.

12 Glenridge Lane, Kings Park
$1,395,000
4 Beds ⋅ 3 Baths ⋅ 1022420 MLS
Step into this stuning coastal sanctuary that offers the ultimate beachside lifestyle. Just a one minute short walk to the water . This property features bright open-concept living, with panoramic views of the harbor and a private outdoor oasis perfect for entertaining. It is a rare opportunity to own a premium slice close to the water. A backyard oasis featuring an in ground free form pool with a jacuzzi spa. Beautiful landscaping and a play ground area. Step inside the upper level to discover a bright, sund-drenched open layout featuring vaulted ceilling and windows with ocean views Large living rooom and dining room with high ceilling and a stone wood-burning fireplace. A large deck on the frond with breathtaking views and a big balcony on the back of the living area. A master bedroom with big closet, and a large private bathroom with skylight. Two additional comfortable bedrooms and a full bathroom. All the bedrooms have closets. Also a beautiful large kitchen with stuning views of the warer and the swimming pool. Amle cabinet space, granite counter tops and stainless steel appliances including a dishwasher, an electric stove, a refregerator and a microwave range. On the first floor there is a large room , a kitchenette with a custum bar and gym, also a utility room and a laundry room. The lot for this property is 75,794 Sq Ft.

588 E Long Beach Road, Nissequogue
$999,999
4 Beds ⋅ 3 Baths ⋅ 1021368 MLS
Welcome to Tuscany in Kings Park, an exceptional and rare opportunity on desirable Ernest Court. Situated on approximately half an acre of beautifully landscaped grounds within the highly regarded Smithtown School District, this 4-bedroom, 2.5-bath Colonial offers the perfect blend of elegance, comfort, and resort-style living. A dramatic cathedral-ceiling foyer welcomes you into a sun-filled interior featuring hardwood floors throughout the main living areas. The spacious formal living room with soaring ceilings and a fireplace creates a warm and inviting atmosphere, while the beautifully appointed kitchen showcases granite countertops, custom cabinetry, radiant heated floors, and an open layout that flows seamlessly into the dining area and family room with a wood-burning fireplace, making it ideal for everyday living and entertaining. Additional highlights include a spacious primary suite, main-level laundry room, central air conditioning, and a two-car garage. A three-season room with a hot tub extends the living space, while the private backyard is designed for entertaining with an above-ground pool and multiple outdoor seating areas surrounded by mature landscaping. Offering exceptional privacy, character, and outdoor amenities, this is a rare opportunity to own a truly special home in one of Kings Park's most desirable neighborhoods.

9 Ernest Court, Kings Park
$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
$834,978
4 Beds ⋅ 3 Baths ⋅ 1019198 MLS
Welcome to this Beautiful Renovated 4-bedroom 3-bath home in Smithtown School District !! This house has it all.. Gas Heat, CAC,In ground sprinklers, Anderson windows, New kitchen, new appliances, renovated bathrooms, wood floors, 2 Car Garage with electric open, Inground swimming pool, Great for entertaining just in time for Summer!

14 Stanley Place, Hauppauge
$999,999
4 Beds ⋅ 3 Baths ⋅ 1017743 MLS
Nestled on a quiet cul-de-sac, this timeless Colonial offers the perfect blend of comfort, elegance, and privacy. Featuring 4 bedrooms and 2.5 baths, the home showcases warm wood flooring, abundant natural light, and a neutral palette throughout. he spacious kitchen is designed for both everyday living and entertaining, offering granite countertops, stainless steel appliances, ample prep space, and a tiered breakfast bar that keeps family and guests connected. Formal dining and living rooms each feature their own fireplace, creating inviting spaces for gatherings and quiet evenings alike. Outside, the private backyard is a true retreat. Backing directly onto parkland, the property enjoys exceptional privacy and features an inground pool surrounded by wrought iron fencing, beautiful paver patios, and multiple seating areas for relaxing or entertaining. Completing the package are a large garage, generous driveway parking, and storybook style curb appeal that makes a wonderful, lasting first impression.

14 Sandpiper Court, Smithtown
$799,803
4 Beds ⋅ 3 Baths ⋅ 1012271 MLS
Sprawling Ranch Situated On A Beautiful Half-Acre Property In The Heart Of Smithtown. This Well-Maintained Home Features 4 Bedrooms, 3 Full Baths, Hardwood Floors, Spacious Living Areas, And A Finished Lower Level With Outside Separate Entrance Offering Flexible Space For Recreation, Hobbies, Guests, Or Extended Living Needs. The Eat-In Kitchen Showcases Cherry Wood Cabinetry, Granite Countertops, And Ample Space For Everyday Dining And Entertaining. Enjoy A Formal Dining Room, Wood-Burning Fireplace, 16 x32 In-Ground Saltwater Pool With Outdoor Shower, Paver Patio, Deck, And Mature Landscaping. Additional Features Include In-Ground Sprinklers, Smithtown Water, Attached Garage, And Updated Systems. The Flexible Floor Plan Includes A Possible Fourth Bedroom Or Home Office To Suit Your Needs. Conveniently Located Near Shopping, Restaurants, Parks, And Transportation. Tax grievance letter is to inform you that we are in the process of professionally grieving the taxes at the above address. Based on our analysis indicates annual property tax reduction of approximately $3,200 a year. (Please see attached letter) If the case is won, a reduction would take place for the 2027/2028 tax year.. Move Right In And Enjoy Everything This Exceptional Property Has To Offer.

9 Dillmont Drive, Smithtown
$3,575,000
6 Beds ⋅ 7 Baths ⋅ 1014535 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
$1,099,999
4 Beds ⋅ 3 Baths ⋅ 1014077 MLS
Welcome to this beautifully updated 4 bedroom, 2.5 bath Colonial, nestled at the end of quiet dead-end street in the desirable Town of Smithtown. From the moment you arrive, the newly paved circular driveway, manicured grounds, and exceptional curb appeal set the stage for what awaits inside. Step through the front door into a stunning open foyer where natural light and elegant design create an immediate sense of warmth and sophistication. Rich hardwood floors flow throughout the home, leading you into a custom designed kitchen featuring quartz countertops, glass tile flooring, abundant cabinetry, and thoughtful finishes that make both everyday living and entertaining a pleasure. A newly renovated powder room off the kitchen has direct access to the yard, perfect for guests enjoying the outdoor amenities. Convenience meets luxury with a spacious mudroom, pantry, and laundry room off the two car garage. A living room, family room with wood burning fireplace and formal dining room complete the layout of the first floor. Upstairs, skylights bathe the landing in natural light, creating a bright and welcoming second floor space. . Four generously sized bedrooms offer comfort and privacy, including a serene primary suite complete with an updated en-suite bath with heated floors, skylight, electric fireplace and two spacious closets. The fully finished basement provides exceptional additional living space and includes a cedar closet for storage and wet bar. Recent updates include a brand new tankless hot water heater, offering efficiency and peace of mind. Outside, prepare to be captivated by an exquisitely landscaped backyard designed for both relaxation and entertaining. Multi level grounds with charming gazebos, a built in heated pool, pool house, two storage sheds and a nine zone sprinkler system combine to create a resort like setting you will never want to leave. Whether hosting summer gatherings or enjoying a quiet evening under the stars, this outdoor oasis is truly unforgettable. A rare opportunity to own a meticulously and thoughtfully updated home in Smithtown.

17 Lower Road, Smithtown
$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
$999,999
3 Beds ⋅ 3 Baths ⋅ 1010352 MLS
Set on over half an acre at the end of a quiet Saint James cul-de-sac, this 4 bedroom, 2.5 bath, 3,313 square foot newer construction center hall colonial offers space, flexibility, and a layout that works for the way people actually live. Hardwood floors run throughout the home, starting with a traditional first-floor layout that includes a welcoming foyer, large formal living room, formal dining room, and a comfortable family room with a wood burning fireplace. Off the family room, sliders open to a huge three-season (300 sq ft) room, creating an additional space to relax, gather, or enjoy the view of the property. From there, another set of doors leads outside, giving the home an easy connection between indoor living and the backyard. The eat-in kitchen anchors the main level with a large center island, generous prep space, sliders to the backyard, and a small butler’s pantry connecting the kitchen and dining room. A first-floor laundry room, two-car attached garage, and basement access add function and convenience to the main level. Upstairs, the second floor opens to a beautiful view overlooking the formal living room below, where cathedral ceilings add height and character to the home. The spacious primary bedroom features vaulted ceilings, two large closets, and an oversized primary bath, while the additional bedrooms feel bright and comfortable with large windows that bring in great natural light. The current upstairs setup offers 3 bedrooms, but this level was originally designed as a 4-bedroom layout and can easily be converted back with one simple wall. With generous room sizes and a flexible second-floor layout, the space can adapt to different needs while still keeping an open, connected feel throughout the home. Outside, the .58-acre property offers a private backyard setting with an in-ground pool, paver areas for lounging and entertaining, in-ground sprinklers, and landscaped front and rear grounds. There is room to enjoy the yard in different ways, whether you are hosting, relaxing, or just appreciating having extra space around you. With its cul-de-sac location, generous square footage, newer construction, and flexible layout throughout, this Saint James colonial offers the kind of space that can grow and change with you.

11 Annemarie Drive, 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
$849,000
4 Beds ⋅ 2 Baths ⋅ 1005767 MLS
Expanded Ranch with Open Floor Plan, Huge Family Room with Pellet Fireplace Insert, 4 Bedrooms, 2 baths, Detached Heated 2 Car Garage, Gunite In Ground Salt Water Pool w/ Loop Loc Cover,150 Amp Service with Transfer Switch for Generator, Desirable Gas Heat, Central Air-5 Years Young, In Ground Sprinklers, Wood Floors, Attic Fan, Large Driveway, Smithtown Schools with HS West, New Stove, Granite Counters, Beautifully Landscaped and MORE !

25 Del Place, Hauppauge
$1,185,000
5 Beds ⋅ 3 Baths ⋅ 1010498 MLS
Welcome to your private retreat, where comfort, space, and timeless charm come together! Set on a beautifully landscaped .71 acre property, this spacious 5 bedroom, 2.5 bath home in the heart of Smithtown, nestled in the beautiful Forestwood section, offers the perfect blend of elegance, functionality, and outdoor living. Featuring gleaming hardwood floors throughout and a thoughtfully designed layout ideal for both everyday living and entertaining. The heart of the home is the beautiful eat-in-kitchen, featuring granite countertops, tons of cabinetry, and plenty of room for casual meals and conversation. For larger gatherings, the formal dining room provides a warm and inviting setting for holidays and special occasions. Relax in the spacious living room, unwind by the wood-burning fireplace in the cozy den, or enjoy movie nights and game days in the separate oversized family room. With five generously sized bedrooms, there’s plenty of space for family, guests, or a home office. Step outside and discover your own backyard oasis. Multiple decks extend the living space outdoors, creating the perfect setting for barbecues, celebrations, or quiet evenings under the stars. The inground freshwater pool invites you to enjoy summer days in style, while the lush gardens, colorful flowers, and mature plantings add beauty and tranquility year round. An amazing standout feature is the large 2 car barn in the backyard, ideal for hobbyists, gardeners, workshop space, extra storage, or parking additional vehicles. This incredible property offers the rare combination of indoor comfort, outdoor enjoyment, and versatile space, all in a setting that feels both welcoming and private. IGS, CAC, 150 Amps

28 Cygnet Drive, Smithtown
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 1006718 MLS
Welcome to your private 1.09-acre retreat, offering the perfect blend of comfort, space, and outdoor living. This beautifully maintained home features wood flooring throughout the main living areas, with tile flooring in the foyer, bathrooms, and laundry room for added durability and convenience. The spacious primary suite is conveniently located on the first floor and includes a walk-in closet and a private en-suite bathroom that features radiant heated floors. An additional first-floor guest bathroom provides added convenience for family and visitors. The large den offers a warm and inviting atmosphere centered around a cozy fireplace, making it the perfect place to relax year-round. The expansive kitchen is designed for both everyday living and entertaining, featuring abundant cabinet storage and generous workspace. Adjacent to the kitchen, the dining room impresses with cathedral ceilings accented by stunning wood beams, creating a bright and elegant setting for gatherings. The laundry room comes complete with a washer and dryer and is neatly enclosed with bifold doors. This room also boasts a radiant heated floor. Upstairs, recent renovations have added modern functionality and charm, including custom built-in shelving in one room and a dedicated built-in TV entertainment area in another. The upstairs bathroom has been tastefully updated with subway tile and a sleek glass partition. Step outside to discover an entertainer's paradise. The backyard showcases a massive 40' x 21' composite deck, ideal for hosting large gatherings, barbecues, and outdoor dining. Beyond the deck, you'll find an expansive 42' x 49' pool area featuring a beautiful L-shaped pool, creating a resort-like setting right at home. The property also includes a large storage shed and is surrounded by a secluded, private yard that offers tranquility and plenty of room to enjoy the outdoors. Set on an impressive 1.09-acre lot, this exceptional property combines spacious indoor living with incredible outdoor amenities, making it the perfect place to call home.

30 Landing Meadow Road, Smithtown
$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
$1,999,999
5 Beds ⋅ 5 Baths ⋅ 992489 MLS
Welcome to this spacious 5-bedroom, 5-bath Colonial set on 1.70 acres in the desirable Head of the Harbor section of Saint James. This 4,788 sq ft home features a functional layout with a first-floor bedroom and full bath, formal dining room, living room, and an open kitchen with granite countertops, center island, and eat-in area leading to a large family room with fireplace. The second level includes a primary suite with walk-in closets and a private bath, along with additional generously sized bedrooms. Additional highlights include hardwood flooring, crown molding, high ceilings, central air, and natural gas heating. The full finished basement offers additional living space with a lavatory. Exterior features include a 3-car garage, private driveway, and an in-ground pool. Conveniently located near major roadways, shopping, and Smithtown schools.

2 Deepwells Lane, Saint James
$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
$2,399,999
8 Beds ⋅ 8 Baths ⋅ 976021 MLS
New Price. Fresh Presentation. One Extraordinary Opportunity. *A Private Resort Where Luxury Meets Everyday Living* Motivated seller has thoughtfully repositioned this exceptional estate with a compelling new price, creating a rare opportunity to own one of Head of the Harbor's most distinctive luxury residences. Hidden at the end of a quiet cul de sac in the prestigious Incorporated Village of Head of the Harbor, 9 Watercrest Court is more than a home. It is a private retreat where holidays become traditions, generations gather, and every weekend feels like a vacation. Thoughtfully designed for exceptional entertaining and everyday living, every space encourages connection while offering the privacy and comfort of a true estate. Spanning approximately 10,000 square feet across all levels, the residence seamlessly blends timeless architecture with modern luxury. A dramatic two story foyer leads to expansive living spaces filled with natural light, soaring ceilings, radiant heated floors, custom millwork, and walls of windows. At the center of it all is a spectacular chef's kitchen featuring Wolf, Sub Zero, and Miele appliances, an oversized island, walk in pantry, coffee bar, and effortless flow into the surrounding gathering spaces. The primary suite offers a peaceful retreat with a spa inspired bath and oversized walk in closets, while the private guest residence, complete with its own kitchen, living room, bedroom, full bath, and separate entrance, provides exceptional flexibility for multigenerational living, extended family, long term guests, live in support, or a private executive suite. Designed for entertaining on a level rarely found in residential real estate, the lower level features a professionally designed private bowling alley, fitness area, recreation spaces, and multiple gathering areas that make birthdays, holidays, game nights, and family celebrations unforgettable. Outside, the resort style backyard offers an in ground pool, expansive patios, beautifully landscaped grounds, and multiple outdoor living spaces designed for everything from peaceful mornings with coffee to summer barbecues and evenings with family and friends. Ideally located in one of Long Island's most sought after North Shore communities, Head of the Harbor offers estate living just minutes from Stony Brook University, renowned hospitals, yacht clubs, golf courses, beaches, fine dining, and major transportation. This is more than a luxury home. It is where your family's next chapter begins. Notable Features • Approximately 10,000 square feet across all levels • Private guest residence with separate entrance • Professionally designed private bowling alley • Resort style in ground pool with expansive outdoor entertaining areas • Chef's kitchen with Wolf, Sub Zero, and Miele appliances • Radiant heated floors • Whole house generator • Fitness area and expansive recreation spaces • Located in the prestigious Incorporated Village of Head of the Harbor

9 Watercrest Court, Head Of Harbor
$1,250,000
5 Beds ⋅ 4 Baths ⋅ 975603 MLS
Welcome to this stately and impressive Colonial, ideally situated in one of Smithtown's most sought after and picturesque neighborhoods. This exceptional property offers a rare opportunity to create a custom luxury home in a truly premier setting. Boasting generous living space the home features a traditional and functional layout with a spacious Living Room, Dining Room, and inviting Den-perfect for everyday living and entertaining. The Kitchen with its Brazilian granite countertops offers generous space and serves as the perfect canvas to design the heart of your dream home. A beautiful feature of the home is a 280 ft expansive SunRoom extension, complete with hot tub, providing a unique space to unwind and relax all year long while overlooking the yard. Upstairs are 5 well appointed bedrooms including the Primary Bedroom with a huge ensuite full bathroom as well as an additional 1/2 bath. The backyard features a newly renovated 20x40 inground pool with new liner and all new coping (1 year old), and approx 3 year old filter, trex decking for low maintenance outdoor living, a beautiful pavillion to entertain under, and a gazebo. A 2 car garage, a young roof, an above ground 550 gallon oil tank, a 4 zone in-ground sprinklers, a tranquil rock waterfall, lightning rods and an expansive stone wall all around the front of the property. With its grand scale, coveted Smithtown location and proximity to the water, this is a rare find for someone to create a truly exceptional home in a prestigious neighborhood.

2 Three Pond Road, Smithtown
$849,000
4 Beds ⋅ 3 Baths ⋅ 977202 MLS
Lovely Colonial Split, 3/4 Bedroom (4th Bedroom or Office), Spacious Throughout, Updated Eat in Kitchen with Granite/.Stainless Steel Appliances, Attractive Great Room for Gatherings, Updated Baths, Upgraded Recessed Lighting, Updated Windows and Pella Doors, Custom Moldings/Trim, Renovated Entry Level Laundry Room, Central AC- 3 Yrs, 3 Zone Heating System- 3 Yrs, Expanded Primary BR Suite with Full Bath and Walk-In Closet, Country Club Yard, Prof. Landscaped, 20x40 In Ground Pool (5 Yr Liner, Loop-Loc Cover and New Filter), Widened Drive, Partial Garage Space for Storage, Property Tax with Basic Star $14,619.47. NOTE: Natural Gas Line in Street.

43 Hallock Avenue, Smithtown

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