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$649,990
3 Beds ⋅ 2 Baths ⋅ 1029446 MLS
Charming Ranch on Oversized Lot in Desirable St. James! Welcome home to this warm and inviting 3-bedroom, 2-bathroom Ranch nestled on an oversized property in the heart of St. James. Offering the ease of single-level living paired with incredible expansive outdoor space, this home is perfect for both relaxed daily living and effortless entertaining. Features Main Level with Bright, fluid layout featuring three comfortable bedrooms and one full bathroom. Finished Basement: with Additional finished space and 2nd Full Bathroom. Outdoor Oasis is Set on an unusually deep/large lot. Limitless potential for a pool, outdoor kitchen, or garden expansion. Prime St. James Location: Enjoy proximity to local shops, dining, top-rated schools, and convenient LIRR access. Don’t miss this rare combination of prime St. James property.

101 Lake Avenue, Saint James
$678,000
4 Beds ⋅ 3 Baths ⋅ 1031653 MLS
Classic Colonial home offering spacious, and comfortable living . The expansive living room and beautiful wood floors throughout the home create a warm and inviting atmosphere. The eat-in kitchen flows seamlessly into the den, featuring a cozy wood-burning fireplace—perfect for everyday living and entertaining. The primary bedroom boasts an updated marble en-suite bath, while the additional bathrooms have also been tastefully renovated with quality finishes. In addition there are 3 nicely sized bedrooms on the second floor. The recently remodeled basement features durable luxury vinyl plank flooring and an outside entrance, providing versatile space for recreation, or a home office.. Step outside to enjoy the backyard deck with retractable awning, ideal for relaxing or hosting gatherings. Conveniently located near local shopping, the Long Island Rail Road, area beaches, fine dining, and Stony Brook University, and Stony Brook University Medical Center, this home offers the perfect combination of comfort, and accessibility. Smithtown Schools

322 2nd Avenue, Saint James
$990,000
4 Beds ⋅ 3 Baths ⋅ 1029417 MLS
Set on a beautifully landscaped 0.80-acre corner property, this custom Farm Ranch offers space, comfort, and exceptional versatility. A welcoming entry foyer opens to a recently renovated eat-in kitchen featuring a striking double-sided fireplace. The bright and airy den is surrounded by walls of windows, while the formal dining room provides easy access to the deck through sliding glass doors. The main level also includes a spacious living room with a custom window seat and a convenient powder room. The first-floor primary suite is designed as a private retreat, complete with a sitting area or home office, a walk-in closet, and an oversized bath featuring a soaking tub and separate walk-in shower. Three additional bedrooms and a full hall bath provide plenty of room for family or guests. The full, partially finished basement offers an outside entrance, laundry area, utilities, and abundant storage or expansion potential. Additional highlights include radiant heat, hardwood flooring, central air conditioning, in-ground sprinklers, Andersen windows, a 150-amp electrical service, generator hookup, updated paver walkways, a roof replaced in 2021, burner installed in 2020, and a hot water heater replaced in 2021. Ideally located near town beaches, Landing Avenue Golf Course, the LIRR, shopping, and dining. This spacious home offers endless possibilities and is much larger than it appears.

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

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

6 Navy Drive, Smithtown
$768,000
3 Beds ⋅ 3 Baths ⋅ 1013242 MLS
Move right in...76 Burlington Boulevard offers timeless modern comfort on one of Smithtown's most tranquil and sought-after neighborhoods in the Smithtown school district. This impeccably updated 3-bedroom, 3-full-bath residence showcases rich hardwood flooring throughout the spacious living room, formal dining room, and inviting family room, creating warm spaces for everyday living and entertaining. The thoughtfully designed layout is complemented by a very expansive, beautifully finished, lower level with designer tile flooring, offering exceptional flexibility and space for a media room, home office, play room, fitness studio, or guest retreat. A detached two-car garage with a low maintenance, long cement driveway and beautifully maintained property complete this exceptional offering. Ideally located just a few blocks from the vibrant shops, restaurants, cafes and everyday conveniences of downtown Smithtown, this home offers the perfect blend of tranquility and accessibility. Whether you're a growing family searching for a move-in-ready home or looking to downsize without sacrificing quality, space, or style, 76 Burlington Boulevard presents a rare opportunity to enjoy refined living in one of Smithtown's most sought-after locations.

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

17 Lower Road, Smithtown
$775,000
5 Beds ⋅ 2 Baths ⋅ 992164 MLS
Stunning 5 possible 6-Bedroom High Ranch in Smithtown East Schools: Welcome Home To This Sprawling And Impeccably Maintained 5-Bedroom, 2-Bathroom High Ranch, Perfectly Situated On An Expansive, Oversized Property Including An Additional Lot. Boasting Incredible Curb Appeal And An Oversized Driveway. This Residence Offers The Rare Combination Of Spacious Interior Living And A Massive Outdoor Oasis. The Heart Of The Home Features A New Updated Gourmet Kitchen Equipped With Modern Finishes, including Soft-Close Cabinets, Stainless Steel Appliances, Center Island, And Quartz Counter Tops, Seamlessly Flowing Into Bright, Open Living Spaces. Both Full Bathrooms Have Been Recently Renovated With Stylish, Contemporary Fixtures. With Five Generous Bedrooms With Ample Closet Space, A Formal Living Room, Dining Room, And Family Room. There Is Ample Space For A Home Office, Guest Quarters, For A Growing Household. Step Outside To Your Private Retreat, Featuring A Sparkling Inground Swimming Pool Surrounded By Professional Landscaping And Vast Green Space, Plus A Screeded-In Patio Space Perfect For Entertaining Or Peaceful Relaxation. Located In The Highly Sought-After Smithtown School District, This Move-In-Ready Gem Offers The Perfect Blend Of Luxury Living, Comfort, And Prime Location. Don't Miss The Opportunity To Own This Unique, Oversized Property!

4 Florence Street, Nesconset
$830,000
3 Beds ⋅ 3 Baths ⋅ 984501 MLS
Move right into this renovated, Townhouse, with 3-bedrooms, 2.5 bathrooms, full basement, 1-car garage, with updated designer kitchen with quartz counters and stainless-steel appliances, updated bathrooms, new flooring/carpeting, fresh paint, etc. Close to local shopping, transportation and amenities. Don’t miss out on this opportunity! Grass photos were digitally enhanced.

26 Stone Gate Court, Smithtown
$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
$2,599,000
6 Beds ⋅ 8 Baths ⋅ 952372 MLS
Paradise on the Nissequogue River with 65 feet of waterfront, ideal for canoeing, kayaking, and serene relaxation. This impressive 5,500+ sq ft contemporary with traditional accents offers 15 rooms and two fully separate living quarters, each with its own basement—perfect for extended or multi-generational living. Both residences feature updated granite eat-in kitchens with wood cabinetry and stainless-steel appliances, formal dining rooms, living and sitting rooms, and spacious primary suites with baths. Additional living space includes two additional bedrooms and a full bath, plus a lower-level spacious guest suite, entertainment rooms, abundant storage, and outside separate entrance (OSE) with its own designated parking. Set on 1.09 beautifully landscaped acres with specimen trees, brick patios, decks and exterior lighting, a spectacular salt water heated gunite in-ground pool (approx. 43’ x 25’) with waterfall, spa, lighting, and natural rock diving board—perfectly positioned to capture sweeping river views. Enjoy evenings by the wood-burning fire pit, surrounded by nautical wildlife and breathtaking sunsets. Located in the highly sought-after Smithtown community, close to fine dining, boutique shopping, theatre, mall, Caleb Smith Preserve, Sunken Meadow Park, beaches, golf, and Smithtown schools. Smithtown offers a blend of tranquil suburban life, historic charm and easy access to parkways and the LIRR/NYC. Additional Features: 2-car garage, North Wing: electric heat exchanger, CAC, heat/AC, South Wing: 3 mini-splits, 5-ton compressor, oil burner, forced hot air/CAC, 60-panel solar system (shared by both wings), In-ground sprinklers, Central vacuum, Two propane tanks, Two fireplaces (one gas, one wood-burning), Two separate hot water heaters, Additional electric panels, Laundry room with slop sink and storage, Brick patio with built-in BBQ

2 Riverview Terrace, Smithtown

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.