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$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
$739,000
3 Beds ⋅ 2 Baths ⋅ 1028816 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of St. James! Convenient distance to shops, restaurants and transportation with taxes under 9k! The stunning 2025 kitchen renovation is the centerpiece of the home. Showcasing natural quartzite countertops, full height backsplash, a 9 ft island with waterfall, professional grade appliances featuring a 6 burner gas range with vented hood. A bar area with beverage center and secondary workstation sink. Original hardwood floors run throughout the home. The fully enclosed, heated and air-conditioned front porch offers year-round enjoyment. The main level also features a formal living room, a full bathroom, recessed lighting, and efficient 4-zone heating and 3-zone cooling for personalized comfort. Upstairs, you'll find the three bedrooms, and another full bathroom, served by 3-zone heating and 2-zone cooling. The partially finished basement was completed in 2024 and provides additional living space. It has its own dedicated heating and cooling zone, along with a front-loading washer and gas dryer. A new high-efficiency Laars wall-mounted gas boiler was installed in 2025. In 2026, the home was fully insulated and finished with maintenance-free Cedar Impressions vinyl siding. The oversized detached two-car garage is equipped with a 60-amp subpanel, multiple 20-amp outlets, and hot and cold water with waste plumbing—ideal for a workshop or hobby space. The property also features a beautifully designed paver patio complete with a wet bar (2024)—perfect for entertaining, ample driveway parking, RV parking, hot and cold exterior water spigots. Additional highlights include Andersen® Thermopane windows, newer architectural roof, new exterior doors, 200-amp electrical service with generator hookup, wifi smart thermostats & porch lights, and eight surveillance cameras. Ideally located a short walk to Lake Avenues shop and restaurants. This home also offers beach rights to multiple Smithtown beaches, close proximity to parks, hiking trails and nature preserves. Situated in the highly regarded Smithtown Central School District.

116 Railroad Avenue, 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
$700,000
4 Beds ⋅ 2 Baths ⋅ 1027335 MLS
This Hi-Ranch Style Home Features 4 Bedrooms, 2 Full Baths, Formal Dining Room, Kitchen & 1 Car Garage. The information provided is estimated to the best of our abilities at this time.

47 Cleremont Avenue, Saint James
$749,999
3 Beds ⋅ 2 Baths ⋅ 1026215 MLS
Nestled on an expansive 12,195 sq. ft. fully fenced property in the heart of St. James and located within the highly acclaimed Smithtown School District, this beautifully maintained farmhouse style Cape Cod is the perfect place to call home. Offering 3 spacious bedrooms and 2 full bathrooms, this inviting residence blends timeless charm with thoughtful updates throughout. Beautifully refinished hardwood floors, a sun filled living room with recessed lighting, a formal dining room, and an updated kitchen create a warm and welcoming atmosphere that's ideal for both everyday living and entertaining. Main-floor laundry adds everyday convenience. The second-floor features three generously sized bedrooms, a full bathroom, a huge walk-in closet, and a large walk-up attic, providing exceptional storage and flexibility. A full basement offers even more storage space and endless possibilities. Step outside to enjoy your private fully fenced front and backyard, complete with a newly updated patio perfect for summer barbecues, outdoor gatherings, gardening, or simply relaxing while enjoying the oversized yard. Ideally located just minutes from the St. James LIRR station, shopping, restaurants, parks, and major roadways, this exceptional home offers the perfect combination of charm, space, convenience, and location. Don't miss the opportunity to own this move-in-ready gem in one of Long Island's most sought-after communities.

214 1st Street, 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
$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
$685,000
3 Beds ⋅ 2 Baths ⋅ 1020879 MLS
Opportunity awaits in the heart of Saint James! This 4-bedroom, 1.5-bath home offers timeless character and incredible potential. Built in 1900 and in original condition, it's ready for your vision and updates. This historic property also features an oversized detached 3-car garage and a spacious workshop—ideal for hobbyists, contractors, car enthusiasts, or additional storage. Situated on a generous lot in a desirable location close to shopping, restaurants, parks, and transportation, this is a rare chance to restore a classic home and make it your own. Adjacent .13 acre lot included in the sale.

174 Railroad Avenue, Saint James
$600,000
3 Beds ⋅ 2 Baths ⋅ 1020426 MLS
Welcome to 376 Moriches Road in St. James, where small-town charm, North Shore convenience, and everyday comfort come together. St. James is known for its welcoming atmosphere, local restaurants, parks, beaches, shopping, rail access, and its close proximity to Stony Brook University, Stony Brook Hospital, Smith Haven Mall, and the Smithtown School District. This three-bedroom, two-bath ranch offers easy one-level living with hardwood floors, an eat-in kitchen with stainless steel appliances, bay windows in the kitchen and living room, and a full, partially finished basement that provides flexible space for a den, home office, gym, playroom, media room, guest area, or storage. Out back, the private fenced yard opens the door to a whole new level of everyday living. Picture summer barbecues, morning coffee on the patio, a fire pit area, garden beds, play space, room for pets, or even creating your own outdoor lounge where friends and family can gather. Whether you keep it simple or build out the backyard retreat you have always wanted, the space gives the next owner plenty of possibilities. With a newer roof and a great location close to town, parks, restaurants, shopping, beaches, and transportation, 376 Moriches Road is more than a home. It is a chance to enjoy the St. James lifestyle while creating the next chapter exactly the way you want it.

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

15 Stillwater Road, Saint James
$2,699,000
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
$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
$765,000
4 Beds ⋅ 2 Baths ⋅ 1013005 MLS
Welcome To 10 Curlin Lane, A Completely Gut-Renovated 4 Bedroom 2 Full Bathroom Colonial Offering The Perfect Blend Of Modern Design, Comfort, And Convenience In The Heart Of St. James. This Stunning Home Has Been Thoughtfully Redesigned From Top To Bottom With Today’s Buyer In Mind. The Brand-New Kitchen Showcases Elegant White Maple Cabinetry With Crown Moulding And Custom Lighting, Sleek Quartz Countertops, A Custom Tile Backsplash, And Stainless Steel Appliances—Creating A Clean, Sophisticated Space Ideal For Both Everyday Living And Entertaining. Throughout The Home, You’ll Find A Seamless Combination Of Large-Format Tile And Rich Hardwood Flooring, Complemented By Recessed LED Lighting That Enhances The Bright, Open Feel. Both Full Bathrooms Have Been Beautifully Customized With Custom Tile And Quartz Finishes, Delivering A Spa-Like Experience. Major Upgrades Provide Peace Of Mind, Including A New Roof, Cedar Shake Vinyl Siding, Windows, 200 Amp Electric Service And Fully Updated Heating And Cooling HVAC Systems. Additional Conveniences Include A Stackable Washer/Dryer And Flexible First-Floor Bedroom With Generous Closet Space—Perfect For Guests, Home Office Use, Or Multi-Generational Living, And A Finished Lower Level For Playroom, Media Room, Or Creative Space. Step Outside Through Sliding Doors Off The Dining Area To A Convenient Patio And Fully Fenced Quarter-Acre Backyard With Shed, Offering Ample Space For Outdoor Gatherings, Recreation, Or Future Enhancements. A Single-Car Garage Completes The Package. Ideally Located Less Than A Mile From The St. James LIRR Station And Just Minutes From Shopping, Top Tier Dining, And All The Amenities Of The Smith Haven Mall, This Home Delivers Both Lifestyle And Location. A True Turnkey Opportunity—Simply Unpack And Enjoy.

10 Curlin Lane, 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
$699,999
3 Beds ⋅ 2 Baths ⋅ 1006934 MLS
Welcome to 3 Bayberry Drive in the heart of Saint James! This beautifully updated home has been renovated from top to bottom within the last six years and offers the perfect blend of style, comfort, and functionality. The stunning kitchen, renovated in 2022, features quartz countertops, stainless steel appliances, custom tile backsplash, recessed lighting, glass display cabinetry, and thoughtful designer finishes throughout. The main bathroom was also completely updated in 2022. There is a full basement with an outside entrance. For added convenience, washer and dryer hookups are available on both the main level and in the basement. Additional updates include beautifully refinished hardwood floors on the main level (2022), central air conditioning on the main floor, and ductless split units in the basement for year-round comfort. Step outside to enjoy the private backyard retreat featuring a spacious deck leading to a large patio—perfect for entertaining guests, outdoor dining, or simply relaxing after a long day. Nestled in a picturesque, storybook neighborhood, this home offers a prime Saint James location close to everything the community has to offer. With countless updates and amenities throughout, this is truly a home that must be seen to be appreciated. Schedule your private showing today before this exceptional opportunity is gone!

3 Bayberry 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
$839,000
5 Beds ⋅ 3 Baths ⋅ 1007352 MLS
The picture-perfect home with the white picket fence. Extensively renovated in 2022, this beautifully updated 5-bedroom, 2.5-bath residence blends charm with modern finishes throughout. Situated on a rare and expansive .67-acre property in the heart of St. James, the home features an open and inviting floor plan designed for both everyday living and entertaining. The main level offers a formal living room with fireplace, a spacious den with cathedral ceilings, and an open-concept kitchen and dining area. The kitchen is appointed with quartz countertops & custom cabinetry. Two bedrooms (possible first floor primary), full bath and a powder room complete the first floor, while the second level features three additional bedrooms and a renovated full bath. Nearly every aspect of the home was updated in 2022 & 2026, including the kitchen, bathrooms, windows, doors, siding, roof, fencing, mechanical systems, fixtures, and oil tank. The grounds offer exceptional outdoor space with expansive, level lawns, mature landscaping, a new paver patio, in-ground sprinkler system, and plenty of room for entertaining, recreation, or future enhancements. A detached two-car garage provides additional storage and convenience. A turnkey home offering the perfect combination of classic character, modern updates, and generous indoor and outdoor living spaces in a convenient St. James location. Will not last!

238 Woodlawn Avenue, Saint James
$1,095,000
4 Beds ⋅ 3 Baths ⋅ 1001456 MLS
Set on .61 acres of flat, beautifully landscaped property in the Hamlet of St. James, this well maintained center-hall Colonial combines timeless charm with spacious living and thoughtful recent updates throughout. The formal living room, dining room, and oversized den are filled with warmth and character, featuring wide-plank pine flooring and generous entertaining space. The den is anchored by a charming wood-burning fireplace, creating the perfect setting for cozy evenings and gatherings. The sun-filled kitchen offers oak cabinetry and is centered around a large island, with a bright breakfast area and sliding doors that open to the backyard oasis. The spacious primary suite provides a peaceful retreat with a walk-in closet and a recently renovated spa-like bath featuring an oversized shower and double-sink vanity. Three additional bedrooms offer wall-to-wall carpeting over hardwood flooring and include custom closet systems. Additional highlights include a large unfinished basement ideal for storage or future finishing, recent updates to the roof, central air conditioning, and bathrooms, offering comfort and peace of mind for years to come. Step outside to your private fully fenced resort-style backyard, complete with an inground saltwater pool with new salt system and paver patio perfect for summer entertaining, relaxing weekends, and outdoor living at its finest. Nearby is local shopping, area beaches, fine dining, and Stony Brook University and Medical Center. Smithtown Schools.

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

14 Hillside Avenue, Saint James
$1,599,000
6 Beds ⋅ 4 Baths ⋅ 948811 MLS
21 Astor Ave Is Located In The Heart Of Saint James Within The Desirable Smithtown School District. This Custom Built And Architecturally Appealing 6 Bedroom, 3.5 Bath Colonial Is Only 25 Years Young & Sits On 3/4 Of An Acre. A Charming Open Front Porch Greets You Before You Enter The Large 2 Story Foyer With Grand Staircase & A Motorized Chandelier. A Bright Formal Living Room Awaits Your Guests Before You Sit Down For A Meal In The Formal Dining Room Featuring A Tray Ceiling. Lovely Hardwood Floors Throughout The Home. The Spacious Custom Kitchen With Island Has Plenty Of Room For A Dining Table And Is Open To The Family Room With Wood Burning Fireplace. There Is Also A Large Enclosed Porch For More Entertaining Space That Leads To The Rear Yard. You And Your House Guests Or In-Laws Will Appreciate The Privacy Of The 1st Floor Guest Quarters With Full Bath & Separate Entrance Complete With Mud Room And Drop Off Station Or This Could Easily Double As A Home Office. The 2nd Level Has 5 Bedrooms, A Full Bath, Laundry Room, And A Large Private En-Suite With Gas Fireplace, Walk-In Closet, And Full Bath With Tub And Separate Shower Stall. If The 4,147 Square Feet Of Living Space Wasn't Enough For You, Then Maybe The Full Finished Basement With A Home Pub & Half Bath Will Help! Wait! Theres More!! Attached 2 Car Garage, Inground Pool, & BONUS Fully Equipped Pool House With CAC & Heat! An Incredible Value For This Much House! Gas Line In Street. Projected ARV $2,300,000 Owner Motivated. Let’s Talk!

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

122 4th Street, Saint James
$990,888
10 Beds ⋅ 5 Baths ⋅ 933897 MLS
Builder special extended family with plenty of living space, Hord wood floor through out on the first floor. Home features 10 bedrooms, 4.5 Bathrooms, 2 car garages fireplace, Gas heat, CAC-system. This unique house sits 032 acre of the flat lot close downtown of Saint James, train station. Needs 24 Hours Noticed to show, Appointment only!

474 Route 25A, Saint James
$775,000
3 Beds ⋅ 3 Baths ⋅ L3591496 MLS
Charming 3 Bedroom, 3 Bathroom Cape With a Thoughtfully Designed Layout. The Main Level Features Two Bedrooms, A Bright Living Room, A Well-Equipped Kitchen, And A Dining Area Perfect For Entertaining. Upstairs, You'll Find A Private Primary Bedroom Suite For Added Comfort. Situated On A Beautifully Landscaped Lot, with a heated in ground pool. This Home Blends Style And Functionality.

10 Marchant Drive, Saint James

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