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365 Van Buren Street, Saint James
$670,000
3 Beds ⋅ 2 Baths ⋅ 1057154 MLS
Welcome to 365 Van Buren Street, a spacious 3-bedroom, 2 full bath ranch, lovingly maintained by the same family since it was built over 55 years ago. Offering a wonderful blend of space, comfort, and opportunity, this move in ready home is ready for its next chapter. The home features a primary bedroom with a private full bath, formal dining room, eat in kitchen, and a spacious family room with a cozy fireplace, solid oakwood floors throughout. Just off the kitchen, a bright sunroom provides additional living space and a perfect spot to relax while overlooking the property. One of the home’s standout features is the additional parcel of land, bringing the total property to over half an acre and offering an abundance of possibilities for outdoor living, entertaining, gardening, growth opportunities, and more. A full basement, one-car garage, and attic provide plenty of additional storage. Additional features include an approximately 6-year-old roof, Peerless oil burner approximately 12 years old, recently serviced central air conditioning, and natural gas available in the area. Conveniently located near the St. James train station, shopping, hospitals, public and private schools, and major roadways. Lovingly cared for through the years, this home offers a wonderful foundation to move right in and add your own special touch.

365 Van Buren Street, Saint James

6 Patricks Way, Saint James
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 1053983 MLS
Welcome to a home where timeless Colonial charm meets comfortable, modern living in the community of St. James. Beautifully designed for both everyday living and effortless entertaining, this exceptional residence offers an abundance of space, amenities, and possibilities. The inviting main level offers generously sized living areas and a formal dining room, creating an elegant setting for dinners, celebrations, and memorable gatherings. Upstairs, you'll find comfortable primary suite and 3 additional bedrooms and downstairs has a layout that allows for the 5th bedroom to serve as a private guest suite, home office, or additional living space to suit your lifestyle. with half Bath The fully finished basement takes the living space to another level, offering endless possibilities for recreation, a home theater, gym, playroom, office, or entertaining area. Whether you're hosting or enjoying a quiet night at home, there's room for it all. Then step outside and discover your own private backyard oasis. The heated , saltwater in ground pool with mood lighting sets the stage for unforgettable summers—spend sunny afternoons poolside, entertaining under the stars, or simply enjoy your own private retreat at the end of the day. Thoughtful features including central air conditioning, gas heat, an in-ground sprinkler system, a generator and a new roof and much more add comfort, convenience, and peace of mind. This is more than just a house—it's a place to gather, entertain, relax, and create memories for years to come. From the spacious interior to the spectacular outdoor setting, this St. James Colonial offers the space, versatility, and lifestyle you've been waiting for.

6 Patricks Way, Saint James

30 Damin Circle, Saint James
$999,000
4 Beds ⋅ 3 Baths ⋅ 1049354 MLS
Welcome to 30 Damin Circle, your beautifully appointed 2,573 sq ft center hall Colonial in the heart of Saint James. Set on a quiet, tree-lined street, this 4 bed, 2.5 bath home offers timeless architectural detail, generous living spaces and a backyard designed for enjoying every season. A covered front porch opens to an impressive center foyer with two closets and elegant crown- moulded openings leading to the formal dining room and oversized formal living room. Crown moulding continues throughout the home, complemented by wainscoting on the staircase and beautiful hardwood floors. French doors connect the cozy den, complete with wood-burning fireplace, to the formal living room, creating a flexible arrangement for entertaining or relaxing. The well-appointed kitchen features granite countertops, undermount sink, stainless steel appliances, double wall ovens, abundant cabinetry and a generous peninsula. The adjoining dining area provides plenty of space for everyday meals and gatherings, while a versatile room just off the kitchen can easily function as a second sitting room, home office, TV room or playroom. An updated tiled powder room completes the first floor. Upstairs, the spacious primary suite features an en-suite bath and walk-in closet. Three additional generously sized bedrooms provide comfortable accommodations for family, guests or home office needs. Both upstairs bathrooms offer under-sink cabinetry, built-in medicine cabinets and laundry hampers. The private, fully fenced backyard is a true extension of the living space, featuring established landscaping, interlocking stone, two decks, a pond and a heated salt-water pool with a new 2026 Loop-Loc cover. Whether hosting summer gatherings or enjoying a quiet afternoon outdoors, this is a space made to be used and enjoyed. A spacious driveway and two-car garage with separate doors provide ample parking and storage. Conveniently located near local amenities and major highways, yet peacefully removed from the bustle, 30 Damin Circle offers the space, character and flexibility to make this home your own.

30 Damin Circle, Saint James

20 Overton Pass, Saint James
$1,449,999
4 Beds ⋅ 3 Baths ⋅ 1054875 MLS
****LOCATION LOCATION ******Brand-new luxury construction in the heart of St. James beautifully designed 4-bedroom, 3-bath home offering high-end finishes, thoughtful craftsmanship and modern living throughout. Set within a private, tucked-away neighborhood with only two points of access, this exceptional residence offers a sense of privacy while remaining close to the Village of Head of the Harbor and all that St. James has to offer. The home features an inviting front porch, spacious interiors, a full basement. Outdoor spaces are equally impressive with a patio, professionally designed landscape beds and spacious side yard. Conveniently located within the Smithtown Central School District and close to St. James Elementary, Nesaquake Middle School and Smithtown High School East. Current property data places St. James Elementary approximately 0.4 mile away, Nesaquake Middle School approximately 1.5 miles away and Smithtown High School East approximately 1.3 miles away. Ideally situated in the heart of desirable St. James, offering the perfect blend of North Shore charm, history and convenience. Enjoy close proximity to the historic St. James village center, local shops and dining, the landmark St. James General Store, and the St. James LIRR station. Nearby Head of the Harbor, Stony Brook Harbor, scenic beaches, parks and waterfront destinations complete an exceptional lifestyle in one of the North Shore’s most distinctive communities. ******“Photos shown are renderings for illustrative purposes only and are subject to change. Final construction, finishes, materials, landscaping, colors, fixtures and other details may vary from those depicted. Renderings are not intended to be a representation or guarantee of final completion. Buyer to verify all features, specifications and finishes with builder/seller.”****

20 Overton Pass, Saint James

18 Overton Pass, Saint James
$1,449,999
4 Beds ⋅ 3 Baths ⋅ 1053682 MLS
**** LOCATION LOCATION LOCATION***** Nestled in the heart of the desirable Saint James, this brand-new luxury construction offers the perfect blend of North Shore charm, history, and convenience. This beautifully designed 4-bedroom, 3-bath home boasts high-end finishes, including a chef’s kitchen with a center island, a stone fireplace, luxury chandeliers, wide plank white oak flooring, thoughtful craftsmanship, and modern living throughout. Set within a private, tucked-away neighborhood with only two points of access, this exceptional residence provides a sense of privacy while still being close to the Village of Head of the Harbor and all that St. James has to offer. The inviting front porch, spacious interiors, and full basement with tremendous potential make this home truly special. An attached two-car garage with direct interior access adds to its convenience. Outdoor spaces are equally impressive, featuring a patio, professionally designed landscape beds, and a beautifully constructed retaining wall with stone stairs to the back yard. Conveniently located within the Smithtown Central School District, this home is close to St. James Elementary, Nesaquake Middle School, and Smithtown High School East. It’s also close to the historic St. James village center, local shops and dining, the landmark St. James General Store, and the St. James LIRR station. Nearby, you’ll find Head of the Harbor, Stony Brook Harbor, scenic beaches, parks, and waterfront destinations, making it an exceptional lifestyle in one of the North Shore’s most distinctive communities. *****“Photos shown are renderings for illustrative purposes only and are subject to change. Final construction, finishes, materials, landscaping, colors, fixtures and other details may vary from those depicted. Renderings are not intended to be a representation or guarantee of final completion. Buyer to verify all features, specifications and finishes with builder/seller.”***

18 Overton Pass, Saint James

50 Plane Tree Lane, Saint James
$769,990
4 Beds ⋅ 2 Baths ⋅ 1052430 MLS
Welcome to 50 Plane Tree Lane, a gem nestled in the heart of Saint James. This lovingly renovated colonial is a blend of charm, comfort, and convenience, ready to welcome its new owners. Boasting four spacious bedrooms, this home offers ample space for relaxation, work, and play. The converted garage now serves as an additional primary bedroom, providing an extra layer of flexibility to your living arrangements. Two fully updated bathrooms add a dash of modern luxury to this classic home. The bathrooms are tastefully designed, combining functionality with aesthetics for a seamless experience. There is also Gas heat. Step into the updated kitchen, where granite counters meet stainless steel appliances, creating a space that's both stylish and practical. Whether you're a seasoned chef or a culinary novice, this kitchen with gas cooking is designed to inspire your home-cooked meals. The home features beautiful hardwood flooring throughout, adding warmth and character to each room. A 14-year-old roof provides reliable shelter, and the ductless air conditioning ensures you stay cool during the warmer months. The is crown molding throughout. The side walked streets just add to the charm of this home. The double driveway outlined by Brick pavers, adds to the beautiful curb appeal. The fenced backyard is the perfect canvas for your outdoor dreams - be it a garden, a play area, or an outdoor entertainment space. This home is not just about indoor living. Located close to the town center, you'll have easy access to a variety of shopping options and restaurants. Whether you're looking for a quick bite or a leisurely meal, you'll find something to satisfy your palate. The full basement provides extra storage or can be transformed into a recreational room or workspace. The home is equipped with gas heating, ensuring a cozy atmosphere during the colder months. The annual taxes for this property, without any exemptions, come to $14,939.31.

50 Plane Tree Lane, Saint James

4 Huber Place, Saint James
$749,999
3 Beds ⋅ 2 Baths ⋅ 1045238 MLS
Welcome to 4 Huber Place, a charming expanded ranch nestled in a wonderful St. James neighborhood on a beautiful 1/4-acre lot. With 3 bedrooms, 2 full baths, and a comfortable, inviting layout, this home offers the space and setting you've been waiting for. The main living areas include a bright living room, dining room, kitchen, and a cozy den with a wood-burning fireplace — the perfect spot to gather, relax, and make memories. Wood floors are believed to be underneath most of the existing carpeting, offering the opportunity to bring out the warmth and character of the home. A full basement provides abundant storage and possibilities, while the 2-car garage adds everyday convenience. With great bones, generous living space, and a lovely property, this home is ready for your personal vision and finishing touches. Enjoy the charm of an established neighborhood, a desirable school district, and a location close to shopping, dining, parks, transportation, and everything St. James has to offer. Come see the possibilities and imagine making 4 Huber Place your next home!Taxes are approximate due to exemptions , Must be verified.

4 Huber Place, Saint James

16 Arlington Avenue, Saint James
$698,000
5 Beds ⋅ 2 Baths ⋅ 1053418 MLS
Welcome to this spacious high ranch, beautifully situated on a generous quarter-acre in the desirable Hamlet of St. James. A paver-stone driveway and matching front walkway provide excellent curb appeal, while the expansive driveway offers ample parking for multiple vehicles. Inside, you’ll find a freshly painted home featuring hardwood floors throughout the main level. The first floor offers a spacious living room and dining room with vaulted ceilings, creating an open and inviting atmosphere. The thoughtfully designed layout is ideal for multigenerational living, with three bedrooms and a remodeled bathroom on the main floor. The bathroom features an oversized walk-in shower with a glass enclosure, a wood vanity, and convenient access from both the primary bedroom and the hallway. The lower level includes two additional bedrooms, a full bath, and a large recreation room. It also offers a private entrance, providing flexibility for extended family, guests, or additional living space. The updated kitchen features recently remodeled cabinetry and new flooring, and opens directly to a spacious composite deck overlooking the private rear yard—perfect for outdoor dining, entertaining, or relaxing. With its versatile layout, generous property, vaulted ceilings, and excellent indoor-outdoor living spaces, this home offers comfort and flexibility. Conveniently located near local shopping, fine dining, area beaches, LIRR and Stony Brook University and Medical Center. Smithtown Schools

16 Arlington Avenue, Saint James

240 Washington Avenue, Saint James
$724,900
4 Beds ⋅ 1 Baths ⋅ 1053499 MLS
The Charming Covered Porch Welcomes You to this 4 Bedroom New England Style Cape Home. This Home has been Lovingly Maintained by its Original Owners. There are all Wood Floors on the first level as well as the Staircase, except for the kitchen. The Formal Dining Room is Perfect for Holiday Gatherings with Family and Friends. The Bath was Recently Renovated with Fresh Paint, New Flooring, Toilet and Vanity. The Eat in Kitchen has a New Gas Stove and a Door that Leads to the Deck and the Back Yard. The Primary Bedroom could be on the first level of the Home or the Largest Bedroom Upstairs. The laundry is in the Basement and the Washer is less than 6 month's old. Relax and Enjoy Entertaining or a BBQ on the Rear Deck. The Oversized Spacious Flat Yard is Fully Fenced for Pets or Play and it is Very Private Surrounded by Trees. The Shed has a Light and the Huge Carport is Great for Additional Storage or a Car Collection. The Driveway is also Spacious and can Accommodate at Least 6 Vehicles. There are All Andersen Windows, Fans, Natural Gas Heat & Hot Water System (approx 12 yrs. old) Gutter Guards and 150 Amp Electric Service. The Roof is approximately 10 years old, Architectural Style Shingles and was Re-Insulated with New Plywood when it was installed. Located in Saint James it is Close to Schools, Stony Brook University and Hospital, Smith Haven Mall, Boutique Shops, Supermarkets, Local North Shore Beaches for Swimming, Boating and Festivals. It's Close to All Major Roads as well as the LIRR. Nearby is the New Centennial Park, an Ice Cream Parlor and Fine Dining Restaurants, all that makes St. James a Desirable and Wonderful Place to Live!

240 Washington Avenue, Saint James

6 Cedarfield Terrace, Saint James
$1,595,000
5 Beds ⋅ 4 Baths ⋅ 1050942 MLS
Introducing 6 Cedarfield Terrace in the beautiful Saint James community of Point of Woods at Berry Hill. Surrounded by Head of the Harbor and Nissequogue, this distinguished enclave offers a refined setting with exceptional privacy, convenience, and tranquility. Masterfully reimagined, this 5 bedroom, 4 full bathroom residence encompasses approximately 4,000 square feet of sophisticated living space on a builder’s acre lot. Sun filled interiors showcase warm white oak floors, soaring ceilings, new windows, a new roof and siding, and elevated finishes throughout. The first-floor primary suite offers a true hotel-like experience, featuring dramatic vaulted ceilings, two walk-in closets, and a beautifully appointed luxurious bathroom. A private guest wing near the garage provides a secluded retreat for guests, a home office, or flexible living space. At the heart of the home, a stunning chef’s kitchen features skylights, a center island, spacious eat-in area, and walk-in pantry. Upstairs, a spectacular loft with soaring ceilings, exposed wood beams, white oak floors, generous closet space, two additional bedrooms, and a full bathroom creates a versatile setting for a playroom, media room, or additional living area. A gracious, extended driveway welcomes you to the property, while the 9-foot-ceiling basement spanning 1,678 square feet and perfectly situated two-car garage provide exceptional functionality and abundant storage. Located within the highly regarded Smithtown School District, with coveted lower Saint James taxes and an enviable Head of the Harbor location, 6 Cedarfield Terrace offers a rare combination of scale, space, privacy, refined design, and an exceptional setting. Just minutes from Stony Brook Village’s renowned restaurants and shops, and close to Stony Brook University Hospital, the property offers unparalleled convenience. Enjoy easy access to Stony Brook Beach, West Meadow Beach, and the scenic waterfront of the North Shore, perfectly complementing this exceptional coastal lifestyle.

6 Cedarfield Terrace, Saint James

9 Swan Place, Saint James
$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, Saint James

15 The Chase, 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, Saint James

49 McKinley Street, Saint James
$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

4 Sunny Road, Saint James
$749,990
3 Beds ⋅ 1 Baths ⋅ 1041719 MLS
Situated on a dead end street, nearly an acre of property in the heart of St. James, this unique 3-bedroom ranch offers space, versatility, and an incredible opportunity for horse lovers! The property is zoned for up to two horses and features a fully functional 12' x 26' barn with electricity—a standout feature! The property also includes an oversized 18' x 23' garage, providing plenty of additional space for vehicles, storage, a workshop, hobbies, or equipment. Inside, you'll find a charming and inviting home featuring a renovated kitchen, beautiful hardwood floors, and a stunning floor-to-ceiling indoor/outdoor fireplace that brings warmth and character to the living space. Enjoy the privacy and possibilities that come with having nearly an acre of land, all while being conveniently located in the heart of St. James. Whether you're an equestrian, need room for your hobbies and toys, or simply dream of having more property, this is a rare opportunity you won't want to miss!

4 Sunny Road, Saint James

29 Hamlet Woods Drive, Saint James
$1,498,000
5 Beds ⋅ 5 Baths ⋅ 1033980 MLS
Built in 2018, this custom Colonial offers approximately 4,300 square feet of thoughtfully designed living space on a beautifully landscaped 0.53-acre property within the prestigious gated community of Hamlet Estates in Saint James. Combining quality construction, modern energy-efficient design, and an exceptional floor plan, the residence features five bedrooms, four full bathrooms, one half bath, a three-car attached garage, and spacious interiors designed for comfortable everyday living and entertaining. The welcoming entry leads to bright, open living spaces highlighted by a dramatic family room with cathedral ceilings, creating an impressive sense of volume and natural light. Formal living and dining areas, a home office, and a first-floor guest suite provide flexibility for today's lifestyle, while the thoughtfully designed layout accommodates both daily living and large gatherings. The gourmet eat-in kitchen is appointed with custom cabinetry, granite countertops, stainless steel appliances, and generous workspace, making it equally suited for casual meals and entertaining. The adjoining family room serves as the heart of the home, while the expansive paved patio and professionally landscaped backyard offer serene views of a picturesque lake, creating a tranquil backdrop for seamless indoor-outdoor living. The primary suite offers a private retreat complete with a spa-inspired bath featuring a Jacuzzi tub, while a second primary-style suite on the first floor enhances the home's versatility for multigenerational living or long-term guests. The remaining bedrooms are generously sized and well served by the home's four-and-a-half-bath layout. Additional highlights include a full basement with approximately 10-foot ceilings offering exceptional finishing potential, ENERGY STAR-qualified construction and mechanical systems, insulated windows and doors, smart thermostat technology, central air conditioning, natural gas heating, central vacuum system and an attached three-car garage. These features combine to provide both long-term efficiency and modern comfort. Hamlet Estates is an exclusive gated community offering 24-hour guard-staffed security and an outstanding collection of resort-style amenities, including a clubhouse, outdoor swimming pool, fitness center, sauna, tennis courts, basketball court, putting green, paddle boats, and beautifully maintained common grounds. Residents also benefit from the highly regarded Smithtown Central School District, making this one of the area's premier luxury communities. HOA common charges apply.

29 Hamlet Woods Drive, Saint James

35 Monterrey Drive, Saint James
$1,589,000
5 Beds ⋅ 4 Baths ⋅ 1024519 MLS
Spectacular 5 BR, 3.5 Bath Post-Modern Colonial in a premier 24hr gated community. This home has been extensively updated with incredible attention to detail. Features include brand-new solid oak hardwood floors throughout the entire house. The spacious kitchen is beautifully updated with a brand-new dishwasher, a high-efficiency exhaust fan, and sleek new countertops with a deep-basin sink. Enjoy a grand open layout, sun-drenched principal rooms, a family room with a fireplace, and a massive primary suite. Pristine 0.41-acre property with a 3-car garage and full basement. Resort-style community amenities include a private clubhouse, sparkling pool, fitness center, and Playground. Smithtown School District. Impeccably maintained with too many updates to list—this turn-key gem feels brand new!

35 Monterrey Drive, Saint James

301 Old Mill Road, Saint James
$2,499,000
6 Beds ⋅ 4 Baths ⋅ 1019623 MLS
Welcome to 301 Old Mill Road, a masterfully crafted custom-built new construction nestled on a private lot backing directly to protected preserve land, offering exceptional privacy in the heart of Saint James. Designed with extraordinary attention to detail, this exceptional 6-bedroom, 4-bath residence blends timeless architecture with refined modern luxury, showcasing soaring ceilings, elegant living spaces, thoughtfully curated finishes, distinctive copper roof accents, and impeccable craftsmanship throughout. Additional highlights include a gourmet chef’s kitchen and an expansive lower level with 9-foot ceilings and egress, offering endless possibilities. Every detail reflects quality, comfort, and thoughtful design, creating a truly one-of-a-kind home that must be experienced in person. Available color upgrade through builder.

301 Old Mill Road, Saint James

67 Sunny Road, Saint James
$1,999,000
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

38 Hamlet Woods Drive, Saint James
$1,699,000
4 Beds ⋅ 8 Baths ⋅ 1008427 MLS
Built in 2010 by Quality Features Inc. to a specification meaningfully above the base community standard, this is a 4,610-square-foot colonial on three above-grade levels with a full walk-out basement, three-car attached garage, and a build quality that is visible in every room: oak, marble, and porcelain floors throughout; custom millwork and moldings on every level; Wolf appliances and granite counters in the kitchen; three gas fireplaces, including one anchoring the Lynx outdoor kitchen on the rear terrace; a whole-house generator sized for a home this large; and a residential three-stop elevator serving all levels. The home is fully ADA-compliant and handicapped accessible, engineered into the original build from the foundation up, not retrofitted as an afterthought. The entry foyer establishes the scale immediately — two-story ceiling, custom staircase, hardwood flooring, millwork that carries through the entire main level. The kitchen is organized around Wolf cooking equipment, Sub-Zero-class refrigeration, granite counters, and custom cabinetry built to ceiling height. The rear of the house opens to the pond from the kitchen and main living areas — the sightline was designed deliberately, so the view is part of the daily experience of the home, not reserved for the terrace. Two gas fireplaces on the upper levels; the third anchors the outdoor Lynx kitchen, which turns the rear terrace into a four-season entertaining space with the pond as a backdrop. The lower level is a finished, walk-out floor in its own right. It houses an endless pool and resistance swim system, a dedicated spa room, and a full bathroom — with natural light, grade-level access to the rear yard, and direct sightlines to the pond. This is not a converted storage space. It is a fourth functional level with a specific purpose. Four bedrooms, seven full baths and one half bath. Every bedroom has a private bath. The primary suite is pond-facing on the upper floor. Ten total rooms. The three-stop elevator eliminates the vertical movement problem that makes most three-story homes harder to live in than they look on paper — groceries, luggage, laundry, and daily circulation across levels all become straightforward. The accessible design and flexible floor plan make this home genuinely adaptable across any configuration of use. Hamlet Estates is a gated community of approximately 85 homes with 24-hour guard-staffed entry, a 9,300-square-foot clubhouse, resort-style pool and spa, lighted tennis courts, full fitness center, basketball court, bocce, playground, lakeside putting green, and two community lakes with paddle boats. The pond this home sits on is one of them — a community amenity that 38 Hamlet Woods has exclusive proximity to. HOA common charges apply.

38 Hamlet Woods Drive, Saint James

2 Deepwells Lane, Saint James
$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

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