Courtesy: Keller Williams Realty Elite
516-795-6900
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.
Courtesy: Signature Premier Properties
631-673-3700
Welcome Home! This charming ranch is perfectly situated in the heart of St. James and offers the ease of one-level living. Featuring 3 bedrooms and 1 full bathroom, the home boasts a welcoming living room with a wood-burning fireplace, a dining area, and an updated kitchen with granite countertops. Additional highlights include vaulted ceilings with skylights, hardwood floors throughout, Andersen windows, 200-amp electrical service, a welcoming front porch, and a full unfinished basement with outside entrance (OSE) offering endless possibilities for additional living space, recreation, or storage. Set on a beautiful, fully fenced corner lot, the backyard is perfect for entertaining with a maintenance-free composite deck and plenty of outdoor space to enjoy. Conveniently located just 0.07 miles from the LIRR and moments from St. James Village, local beaches, Smith Haven Mall, shopping, dining, and major roadways. Located within the Smithtown Central School District, serving St. James Elementary School, Nesaquake Middle School, and Smithtown High School East. Photos have been digitally edited. If you're looking for a ranch offering comfort, convenience, and easy living, look no further—this is the one you've been waiting for!
Courtesy: Compass Greater NY LLC
631-315-7965
A stunning, fully reimagined luxury home where timeless design meets modern living. Completely renovated from top to bottom in June 2026. This exceptional 4-bedroom, 3.5-bath residence showcases magazine-worthy interiors, wide-plank 9.5-inch white oak flooring, custom millwork, designer lighting, and a dramatic double-sided European concrete fireplace that serves as the architectural centerpiece of the home. The chef's kitchen was designed for both everyday living and entertaining, featuring custom two-tone cabinetry, a handcrafted hood, farmhouse sink, oversized gathering island, walk-in pantry, and a suite of premium Miele appliances. The luxurious primary suite and four designer bathrooms offer spa-inspired finishes, custom tilework, bespoke vanities, luxury fixtures, and illuminated backlit mirrors. Outside, professionally landscaped grounds, lush sod, Cambridge walkways, expansive patios, and a custom fire pit create a private setting ideal for entertaining and relaxation. Additional features include a finished basement, main-level laundry room, three-car garage, Andersen 400 Series windows and doors, new roof, new plumbing, new electrical, new irrigation system, and two new Daikin HVAC systems. Every surface, finish, and detail has been thoughtfully curated to create a truly turnkey home that feels custom built. Rarely does a property of this caliber come to market. Set on a beautiful cul-de-sac in the heart of Nissequogue, and minutes from the beach, this move-in ready residence perfectly blends timeless style, comfort, and sophistication. An exceptional opportunity to enjoy one of the North Shore's most sought-after communities!
Courtesy: Stephen Joseph Properties
516-809-9288
Welcome to this beautiful St. James home. This must-see 4 bedroom, 2.5 bath residence offers a wonderful blend of comfort, style, and charm. Spacious living areas, and a perfect layout. Step outside to your very own private backyard oasis, complete with a stunning in-ground pool and a serene setting perfect for relaxing, entertaining and creating lasting memories. A truly special home that offers the perfect combination of indoor elegance and outdoor enjoyment!
Courtesy: Howard Hanna Coach
631-751-0303
Welcome to 259 Woodlawn Avenue in the heart of St. James. This well-maintained and tastefully updated Cape offers 3 bedrooms, 1.5 bathrooms, and a move-in ready interior filled with warmth and character. The open kitchen features granite countertops and flows seamlessly into the main living areas, while updated bathrooms and newer vinyl flooring add modern comfort throughout. Major improvements include a newer boiler, oil tank, hot water heater, updated electric service, younger vinyl replacement windows, and a new composite rear deck. Situated on a flat, fully fenced quarter-acre property with young vinyl fencing, the backyard provides plenty of space for entertaining, gardening, pets, or play. Set back with driveway access from 7th Avenue, the property enjoys a surprisingly private feel while remaining convenient to shopping, restaurants, parks, and transportation. Combining the charm of an older home with the peace of mind of numerous updates, this meticulously maintained residence is ready for its next owner to move right in and enjoy.
Courtesy: Howard Hanna Coach
631-751-0303
Enjoy maintenance-free luxury in the highly desirable Fairfield at St. James community. This pristine 2-bedroom ranch condo is completely updated from top to bottom, featuring a stunning new kitchen, modern baths, and newer AC and hot water tank. With no one living above you and an attached 1-car garage, this home offers rare convenience and privacy. The back patio opens to peaceful views with total rear privacy. A turnkey gem that is an absolute must-see! Community amenities galore!
Courtesy: RE/MAX Integrity Leaders
631-736-2000
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.
Courtesy: Greene Realty Group
888-278-5840
Lovingly maintained 2bd 1 1/2 bath unit located in the desirable Gotham section. Living room with 12ft ceilings and recessed lighting. Primary Bedroom suite, second bedroom with 1/2 bath. Completely updated , including new eat in kitchen with granite counter tops, stainless appliances ,updated baths with Primary bath walk in shower, new flooring, and custom closets. New Anderson windows and sliding glass door that leads to a beautiful patio area with new awning. Garage, which includes above attic storage with stair access. This unit is ready for you to move in settle down and enjoy. A few of the many amenities included in The Fairfield Community are a pool, tennis courts, and clubhouse just to to name a few.
Courtesy: DeBarbieri Assoc Inc
631-862-7447
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.
Courtesy: Compass Greater NY LLC
631-629-7719
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.
Courtesy: Signature Premier Properties
631-422-3100
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.
Courtesy: Signature Premier Properties
631-360-2800
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
Courtesy: STOEBE & CO
631-998-4545
Commanding a position of unrivaled prestige on Long Island’s legendary Gold Coast, this truly distinguished waterfront masterpiece reigns over 6.2 acres of ultra-private Nissequogue land. This rare, generational legacy property seamlessly fuses magnificent estate living with elite equestrian potential and extraordinary development flexibility, offering a potential 3+/- lot subdivision or the option to purchase an additional 4.02 acres of adjacent vacant land. Beyond the threshold of the estate, a breathtaking grand foyer introduces a main level of epic scale and architectural sophistication, where a stately living room anchored by a roaring fireplace, refined sitting room, private library, quiet home office, two sunrooms, and an expansive bonus room flow effortlessly into a culinary epicenter featuring an eat-in kitchen, breakfast area, pantry, and an elegant screened-in porch. The upper levels are a masterclass in private luxury, anchored by a regal master suite boasting a massive walk-in closet, four additional bedrooms gracefully configured into two dual-suite wings with shared full bathrooms, and a large lavish en-suite, bonus room, and an attic staircase that dramatically unveils an elevated sunroom terrace overlooking the sweeping panoramic view of the sound and estate grounds. Below, a connoisseur’s basement level hosts a dedicated wine cellar, rare vintage fur vault, and an expansive laundry room, while a 3-car garage with a half bath sits beneath an ultra-private, 2-bedroom, 1-bathroom guest loft. Surrounding the magnificent manor, the breathtaking grounds open up into a resort-style paradise with majestic, mature landscaping, a sparkling pool with a dedicated pool house, charming garden house, and a classic greenhouse. While completely secluded within its own private sanctuary, this magnificent estate stands as a towering achievement of timeless luxury just mere minutes from the fairway at the exclusive Nissequogue Golf Club, pristine beaches, marinas, and the historic Knox Boarding School. An offering of this caliber is a rare privilege, destined for a discerning buyer ready to inherit one of the North Shore's most definitive luxury properties.
Courtesy: Coldwell Banker American Homes
631-863-9800
Incredible Opportunity to Enjoy the Lifestyle You’ve Been Waiting For in the Highly Desirable Fairfield 55+ Community in St. James! This exceptional first-floor condominium offers true no-step living, making everyday life effortless and convenient. Ideally located just steps from your assigned parking space, this light-filled home features an open and inviting floor plan designed for comfortable living and entertaining. The spacious living room showcases recessed lighting and a large sliding glass door that fills the space with natural light while providing access to your private patio. The eat-in kitchen offers white cabinetry, white appliances, a stackable washer and dryer, recessed lighting, a ceiling fan, and abundant cabinet and counter space. Custom plantation shutters throughout allow you to enjoy natural sunlight or complete privacy at any time. The oversized primary bedroom features a large walk-in closet, while the updated full bathroom includes a white vanity, black-framed mirror, and spacious walk-in shower. Additional highlights include central air conditioning, an exterior storage closet, assigned parking, and ample guest parking. Enjoy a carefree, resort-style lifestyle with low taxes and access to outstanding community amenities, including indoor and outdoor saltwater pools, a fitness center, clubhouse, library, billiards room, card room, tennis courts, pickleball courts, walking trails, a gazebo, picturesque pond, and a full calendar of social activities. Conveniently located near shopping, dining, and transportation, this is an exceptional opportunity to enjoy active adult living at its finest. HOA approval required. Low taxes.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-584-6600
Nestled on 2.5 private acres in the picturesque Village of Nissequogue, this beautifully remodeled Colonial offers a rare opportunity to enjoy peaceful country-style living with seasonal water views of the Nissequogue River in one of Long Island’s most sought-after communities. This well-maintained home features numerous updates, including a newer roof, siding, driveway, eat-in kitchen, and hardwood flooring throughout the first floor. The interior was freshly painted in March 2026, creating a bright and welcoming atmosphere. The spacious den is highlighted by a cozy wood-burning fireplace with a stove insert, perfect for relaxing on cooler evenings. Updated bathrooms add modern comfort, while the full basement and attached two-car garage provide ample storage and functionality. Enjoy tranquil outdoor living from the rear patio, where partial river views can be appreciated during the summer months. The backyard is surrounded by mature trees, offering privacy, serenity, and a peaceful natural setting. Ideally located near local beaches, hiking and nature trails, fine dining, shopping, and Stony Brook University and Medical Center. This exceptional property combines scenic beauty, modern updates, and convenient access to area amenities. Smithtown Schools
Courtesy: Maison Pawli LLC
631-364-2113
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.
Courtesy: Signature Premier Properties
631-642-2300
Welcome to this charming and beautifully maintained Colonial nestled on a corner property in the heart of St. James. Originally built in the 1800s, this one-of-a-kind home is filled with timeless character and charm while offering modern comforts throughout. Featuring 3 bedrooms and 2 full baths, hardwood floors, central air and stunning wraparound porch adds incredible curb appeal and creates the perfect place to relax and enjoy the beauty of this picturesque property. Located in a desirable neighborhood this home offers the perfect blend of historic charm, space, and convenience with close proximity to local shops, restaurants, parks, and transportation. A rare opportunity to own a truly special home in sought-after St. James.
Courtesy: Douglas Elliman Real Estate
631-751-6000
Welcome to 7 Applewood Road located in the Smithtown School District. This lovely Ranch style home features a spacious eat-in-kitchen with newer appliances and a bay window, living room with a sunny bow window, family room with a wood burning fireplace which leads you into a beautiful four season sun room, a sizable primary bedroom with his/her closets, 2nd bedroom with double closet, 3rd bedroom with a nice size closet, updated full bathroom, hardwood floors, 2014 CAC, Gas heating and cooking, 40 gal. hot water heater, forced hot air heat, appropriate outlet for portable generator, 6 zone sprinkler system, 2015 roof, very sunny .25 acre fully fenced, full basement with newer washer only & dryer, partially finished. This property incorporates peaceful suburban living with easy access to everything North Shore has to offer. There is a lovely park right down the road and playground. Visit down town St. James for a wonderful experience shopping, dining, parks and major roadways, easy access to the Smith Haven Mall. A stones throw away from the beautiful villages of Port Jefferson and Stony Brook. Come and have an ice cream cone down by the Harbor or shop til you drop! Enjoy the summertime concert and all events all year long! Close to public transportation, LIRR, Port Jefferson Ferry to Bridgeport CT, Long Island Expressway, along with Northern State Parkway. Taxes: $12,285.59 - Star Deduction $877.00
Courtesy: Signature Premier Properties
516-799-7100
Welcome to 257 Fourth Street, a beautifully maintained and thoughtfully updated Colonial nestled in the heart of Saint James. Offering 4 bedrooms, 3.5 bathrooms, and a floor plan designed for both everyday living and entertaining, this home combines timeless charm with modern amenities in one of Long Island's most desirable North Shore communities. The interior features spacious living areas, an updated kitchen with radiant heated floors, a finished basement complete with a full bathroom and beverage refrigerator, and a luxurious primary suite highlighted by a custom steam shower. Whether you're hosting summer gatherings, relaxing poolside, enjoying a quiet morning coffee on the front porch, or spending an evening around the fire pit with family and friends, 257 Fourth Street offers a lifestyle that's hard to find and even harder to leave. Step outside and discover a private backyard retreat surrounded by mature hedges, creating a tranquil setting for both entertaining and relaxation. The heated saltwater pool with sun shelf, outdoor shower, expansive paver patio, and fully equipped outdoor kitchen featuring a built-in DCS gas barbecue and beverage refrigerator create an exceptional outdoor living experience. The backyard bar provides additional seating and gathering space, making it the perfect setting for memorable celebrations and everyday enjoyment alike. Additional highlights include a 15kW natural gas whole-house generator with automatic transfer switch, landscape lighting, ductless heating and air conditioning in the garage, extensive garage shelving, storage shed, an oversized paver driveway accented with cobblestone curbing, a high-efficiency natural gas boiler, and an 80-gallon hot water heater. Significant improvements include the roof, siding, stonework, pool, pool liner, and pool equipment, providing peace of mind for years to come. Conveniently located near shopping, dining, parks, transportation, and all that Saint James has to offer, this exceptional home delivers the perfect blend of comfort, convenience, and resort-style living. A rare opportunity to own a truly special property with outstanding indoor and outdoor living spaces in one of the North Shore's most sought-after communities.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-427-6600
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!
Courtesy: Coldwell Banker American Homes
631-863-9800
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!
Courtesy: Douglas Elliman Real Estate
631-543-9400
Welcome to 29 Three Sisters Road, a unique custom-built residence that effortlessly blends historical charm with modern elegance. Built in 1847 and completely renovated, this 4-bedroom, 3-bathroom home is a testament to timeless design and quality craftsmanship. The heart of the home, a stylish kitchen, offers gas cooking, granite counters, and an inviting dining area. The den area, adorned with a cozy wood-burning fireplace and meticulously maintained hardwood floors, serve as welcoming spaces for relaxation and entertainment. There is a large formal dining room great for gatherings and dinner party's. The large formal living room which overlooks the beautiful backyard with vaulted ceiling is an absolutely must see entertaining room. The house has been expanded from its original size. The main level hosts the primary bedroom featuring a walk-in closet and a luxurious updated bathroom. There is also a 2nd, first floor bedroom that doubles as a second den with vaulted ceilings. The first floor also has an beautifully updated full bathroom. The second level unveils two additional bedrooms, a full bathroom, and a versatile office space which at one point was used as a small 5th bedroom. Additional features include a beautifully finished basement with laundry room and ample storage space. The roof, Central Air conditioning, gas heating. and the cesspool are all approximately 10 years old. The outdoor spaces are equally impressive, with an inground sprinkler system in the front and back, a spacious shed, and professionally landscaped gardens that surround the brick patio and walkways. The home also boasts two driveways. This home has just received a permit for town-approved circular driveway and a 2-car garage. The house has a full house gas Generac generator. The wrap around front porch is such a quant feature for just relaxing. Taxes are $14,111 plus $1,513 for the Head of the Harbor Village taxes for a total of $15,624 Located in the heart of Harbor NY, you'll enjoy close proximity to beaches, shops, and the iconic Saint James General store.
Courtesy: Signature Premier Properties
631-360-2800
Located on a pristine, tree-lined street north of 25A in highly desired St. James, this spacious 4 BR, 3.5BA colonial boasts hardwood floors throughout, 2 fireplaces, updated natural gas heat, and a full finished basement w OSE offering plenty of room for extended family. First floor offers a separate home office. The spacious 2 car garage has plenty of room for cars and additional storage. Updated Andersen windows, flat usable private yard with land-locked, state-owned property directly behind it, serving a beautiful, natural buffer for privacy. Central air approx 6 years old, 200 amp service, Cesspool is approx 10 years old. Roof approx 10 years old. Generously sized rooms and a primary en-suite with 2 closets and primary bath! This home offers an abundance of closet space and meticulously maintained In-ground sprinkler system. Short drive to beautiful north shore beaches and close to some of the most highly rated restaurants and shops in the area. Do not miss this opportunity!
Courtesy: Daniel Gale Sothebys Intl Rlty
631-584-6600
Elegant and inviting expanded ranch featuring numerous recent updates and spacious living throughout. Expanded in 2009, the home offers generously sized bedrooms and a layout designed for both comfortable living and entertaining Upon entering, you are welcomed by a spacious formal dining room highlighted by a large picture window that fills the space with natural light. Just beyond, the stunning great room features pegged hardwood flooring, a cozy wood-burning fireplace, and custom built-in bookshelves, creating the perfect gathering space. Recently remodeled in 2024, the kitchen boasts white cabinetry, quartz countertops, stainless steel appliances, and a sunny breakfast nook ideal for casual dining. The private primary suite offers a vaulted ceiling with high hats, a walk-in closet, and its own full bath. Two additional oversized bedrooms share a beautifully maintained full bathroom. Additional features include a partially finished basement, new central air conditioning, a new cesspool, updated heating system, and many new or replaced windows throughout the home. Outside, the fully fenced backyard creates a private retreat complete with an in-ground pool featuring a new liner and new heater — perfect for relaxing or entertaining all summer long. Ideally located near area shopping, fine dining, local beaches, and Stony Brook University and Medical Center. Smithtown Schools
Courtesy: Gateway to The Hamptons R E
631-325-3449
Welcome to this spectacular 5-bedroom, 1.5-bath Colonial nestled on an incredible 1.5-acre property in one of the area's most exclusive locations—north of North Country Road (25A), just steps from the General Store and the charm of Head of the Harbor, and only minutes to Long Beach and Short Beach. This exceptional home combines timeless appeal with extensive modern updates, offering the perfect blend of elegance, comfort, and convenience. A beautifully expanded circular driveway provides parking for 10+ vehicles and leads to a recently renovated 1.5-car garage featuring epoxy floors, abundant storage, a new attic access, and plywood attic flooring for even more storage possibilities. Inside, you'll find an inviting open floor plan with hardwood floors throughout and a stunning granite eat-in kitchen featuring a granite backsplash, a counter-height granite center island with additional storage, and convenient Sweepovac systems in both the kitchen and laundry room. Just off the kitchen is a full laundry room, adding everyday practicality and function. The lower level is enhanced with recessed lighting and elegant crown molding throughout, creating a warm and refined atmosphere. The living room serves as a beautiful gathering space, complete with an electric fireplace with a stunning mantle and wired for 5-in-1 surround sound—perfect for entertaining or cozy nights at home. A full, unfinished basement provides excellent storage space and endless potential for future expansion, a home gym, workshop, or customization to fit your needs. Nearly every aspect of this home has been thoughtfully updated since 2017, creating a truly move-in-ready experience. Major improvements include natural gas conversion with a 5-year-young Navien on-demand tankless boiler and water heater, new sheetrock throughout the lower level, vinyl siding, fencing, and oversized 6-inch gutters installed in 2020. Outdoor living is equally impressive with Trex front deck and rear patio renovations completed in 2021, along with extensive pool upgrades including reconstructed plumbing, a gas heater, and a new liner. The expansive property offers something for everyone, featuring a custom-built predator-proof chicken coop ready for chicks, a playground, two full vegetable gardens, and a 6-year-old hot tub—creating a private backyard retreat with endless possibilities. Whether entertaining, relaxing, gardening, or enjoying the privacy of this extraordinary property, this home delivers exceptional space, thoughtful upgrades, and a truly unmatched lifestyle in one of the area's most sought-after locations. A rare opportunity to own a beautifully updated Colonial in an exceptional setting.
Saint James is located in New York. Saint James 11780 is more family-centric than the surrounding county with 34.47% of the households containing married families with children. The county average for households married with children is 32.94%.
