Smithtown Homes with Landscaped Lot features

Welcome to the vibrant community of Smithtown, nestled in the heart of Suffolk County, New York. Renowned for its exceptional school district, Smithtown offers families an outstanding educational experience that prioritizes academic excellence and personal growth. The Smithtown Central School District is celebrated for its dedicated faculty, diverse curriculum, and a wide array of extracurricular activities that foster well-rounded development. With highly-rated schools, students are encouraged to explore their interests while receiving a robust education that prepares them for future success.

Beyond its educational offerings, Smithtown is a picturesque suburb that boasts beautiful homes with landscaped lot features. Imagine coming home to a serene oasis, where manicured lawns and vibrant gardens create a welcoming atmosphere for family gatherings and outdoor activities. These homes not only provide a comfortable living space but also offer a canvas for your personal touch—perfect for gardening enthusiasts or those who simply appreciate the beauty of nature.

Living in Smithtown means embracing a lifestyle that balances tranquility with community spirit. Enjoy nearby parks, recreational facilities, and charming local shops, all while being just a short drive from the bustling energy of New York City. Whether you're looking for a cozy starter home or a spacious family residence, Smithtown's real estate market has something for everyone. Discover the perfect blend of top-tier education and beautiful living spaces in this enchanting town—your dream home awaits!

Newest Smithtown Homes with Landscaped Lot features

$859,990

3 Beds ⋅ 2 Baths ⋅ 1031558 MLS

Set on 1.25 acres backing directly to the Nissequogue River Preserve this Sprawling Ranch offers a setting that is truly special. Protected woodland replaces neighboring homes, offering a peaceful backdrop where wildlife and changing seasons become part of everyday life. Inside, this inviting ranch features 3 bedrooms, 2 full baths, a farmhouse-inspired kitchen with breakfast nook, separate formal dining room, and beautiful hardwood floors throughout. The spacious family room is filled with natural light and anchored by a brick wood-burning fireplace with removable electric insert, while the formal living room showcases exposed wood beams and a wood-burning stove. Just off the primary suite, a sun-filled sitting room provides the perfect retreat to enjoy your morning coffee while taking in views of the surrounding landscape. Outside, enjoy summer days by the fenced 20x40 in-ground pool with a 2-year-old liner, or relax on the wood deck and brick patio surrounded by mature trees and the peaceful sights and sounds of nature. The fully permitted barn with attached carport and covered patio offers incredible versatility with potential uses including equestrian space, workshop, studio, home gym, or a cottage for extended family or rental income with proper permits. Additional features include a brand-new roof with flashed skylights, new gutters, propane service for cooking and laundry dryer, two-car attached garage, and a full unfinished basement with egress window offering even more possibilities. Conveniently located minutes from Blydenburgh County Park, Caleb Smith State Park Preserve, beaches, shopping, dining, and within the highly acclaimed Smithtown School District, this is a rare opportunity to enjoy the peace of a private setting while staying connected to everything Smithtown has to offer.

16 Landing Meadow Road, 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

$849,000

4 Beds ⋅ 3 Baths ⋅ 1026950 MLS

Contemporary 4-bedroom, 2.5-bath home situated on approximately 0.35 acres in the Smithtown School District. Built in 1967, this spacious residence offers approximately 2,745 square feet of living space, a fireplace, and a partial basement. The generous lot provides ample outdoor space for entertaining, gardening, or recreation. Conveniently located near shopping, restaurants, parks, major roadways, and other everyday amenities. A wonderful opportunity to make this home your own.

12 Kenny Street, Hauppauge

$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

$999,000

4 Beds ⋅ 3 Baths ⋅ 1020597 MLS

When opportunity knocks the door must be opened. Welcome to 57 Brooksite Drive. A stunning single unit home in the heart of Smithtown NY sitting on nearly a half an acre of property. Renovated just over 1 year ago this home is being offered to the market at an amazing opportunity to be purchased as turn key as they come. Enjoy the state of the art renovations throughout the property including a finished basement, a first floor master bedroom, and an open concept dining room & kitchen. Spark up the fire and sit with the entire group as you enjoy the fully functional living room fireplace. Walk out your sliding door and gaze at your massive nearly half acre of land where you can host and entertain your friends. Got a project? Your attached garage gives you plenty of space to park your car and sustain your handyman fix. This property needs absolutely nothing except your willingness to enjoy it's perfection. This is a truly ICONIC home! Showings by appointment only.

57 Brooksite Drive, Smithtown

$2,049,000

4 Beds ⋅ 4 Baths ⋅ 1014240 MLS

Exceptional Custom Estate in the Heart of St. James Proper, Situated on 1 Acre of Meticulously Maintained & Landscaped Property with a Resort Style Bucolic Yard. A Covered Front Porch leads into a Double Height Entry Foyer. Offering Four Bedrooms, Four Full Baths, a Family Room with Wood Burning Fireplace, Hardwood Floors, Built-ins & Custom Millwork Throughout. Private Den, First Floor Full Bath, Primary Ensuite with Two Walkin Closets, Propane Fireplace, Private Balcony & Custom Private Bath with Shower, Whirlpool Tub, Bidet & More. Three Additional Bedrooms on Second Floor & Brand-New Full Bathroom. Finished Basement 9' Ceilings with Custom Millwork, Outside Entrance, Custom Bar, Office, Full Bath, Movie Theatre & Much More. Bucolic Rear Yard Encompasses a Double Height Paver Patio, Outdoor Kitchen, Rear Awning, 35x35' Saltwater Heated Inground Pool with Waterfall, Covered Entertainment Area, Tennis Court with Pickleball & Basketball. Rear Stadium Lighting, Built-in Fireplace, Elevated Gazebo, Two Car Detached Garage & Rear Pool House Area. Four Car Garage Total. 400 Amp Electric. Two Zones CAC, two 275 Gallon Oil Tank in Basement. Central Vacuum, Low Line Septic, Built-in Fishtank. Mature Landscaping, Landscape Lighting, Architectural Roof, Pool Table & Much More. Must See to Appreciate. All information to be verified independently by Buyer/Agent. Inquire About CO's.

67 Sunny Road, Saint James

$999,999

3 Beds ⋅ 3 Baths ⋅ 1010352 MLS

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

11 Annemarie Drive, Saint James

$2,399,000

6 Beds ⋅ 5 Baths ⋅ 1010665 MLS

Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with expansive living spaces filled with natural light of generous proportion and seamless indoor-outdoor flow creating a tranquil retreat just moments from the harbor, beaches, yacht clubs, vineyards and nature preserves. Set on two beautifully landscaped level acres of property designed for both everyday enjoyment and sophisticated entertaining. This private estate seamlessly blends timeless elegance, modern luxury, and resort-style living. A grand two-story foyer introduces the home's sophisticated interiors, where soaring cathedral ceilings, gleaming hardwood floors, abundant natural light, and exquisite architectural details create an atmosphere of warmth and refinement. Thoughtfully updated throughout, every space has been designed with both everyday comfort and effortless entertaining in mind. The recently renovated chef's kitchen serves as the heart of the home, featuring a dramatic Crawford ceiling, custom crown and box moldings, quartzite-topped center island, and a suite of premium appliances including a Sub-Zero refrigerator, Bosch range, double ovens, microwave drawer, and dishwasher. The kitchen flows seamlessly into the impressive great room, highlighted by a floor-to-ceiling stone wood-burning fireplace and walls of windows overlooking the picturesque grounds. Elegant entertaining spaces continue with a gracious formal living room accessed through glass pocket doors, and a spacious dining room perfectly suited for hosting intimate gatherings or larger celebrations. The main level offers five generously proportioned bedrooms and three full bathrooms, including two recently renovated baths appointed with refined finishes. Upstairs, an expansive loft with hardwood floors overlooking the great room provides additional living and entertaining space and leads to the luxurious primary suite. This private retreat features hardwood flooring, custom closets, detailed millwork, and a stunning newly renovated spa-inspired bath complete with a soaking tub, oversized glass-enclosed shower, dual vanity, and exquisite Italian tile. The outdoor setting is nothing short of extraordinary. Professionally landscaped grounds surround a tranquil in-ground pool, complemented by multiple paver patios designed for elegant outdoor entertaining and relaxation. A sprawling Trex deck extends nearly the entire length of the home, creating a seamless connection between indoor and outdoor living. Additional highlights include a fully finished lower level with a full bath, offering exceptional flexibility for recreation, fitness, guest accommodations, or extended living space. Car enthusiasts will appreciate the rare offering of four garage spaces, including two attached and two detached garages. Recent improvements include extensive interior and exterior painting, newer windows, custom closet systems, wood flooring throughout most of the house and numerous thoughtful upgrades throughout. A wonderful opportunity awaits for you to own this property and reap the rewards of resort living in the White Spruce Farm Community within the Village of Head of the Harbor. Taxes Include Village Taxes of $3,199

15 The Chase, Saint James

$1,200,000

5 Beds ⋅ 3 Baths ⋅ 1011636 MLS

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

451 River Road, Nissequogue

$1,890,000

4 Beds ⋅ 3 Baths ⋅ 1008414 MLS

Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a professional contractor as his personal home with attention to detail and premium materials throughout. Situated on a private 1-acre property, this exceptional 4-bedroom, 2 1/2 bath home welcomes you with a striking stone façade and dramatic arched entryway that sets the tone for the extraordinary craftsmanship found throughout. Features include oak hardwood floors, solid hardwood interior doors, custom millwork, marble and tile mosaics, a custom detached 2-car garage with handcrafted garage doors built by the homeowner and features its own electrical panel. The fully finished basement includes an outside entrance, laundry area and epoxy flooring. The large, open kitchen includes custom cabinetry, granite countertops, stainless steel appliances, and custom designed tile work. A breathtaking handcrafted marble fireplace with carved lion statuary serves as the centerpiece of the home and features a heat-circulating system with dedicated venting to the primary suite above. Built with 2x6 construction and blown-in insulation for exceptional energy efficiency, the home was also strategically positioned above grade to promote superior drainage. Smart home features include remote thermostat controls with separate zones in each bedroom and an automatic leak-detection water shutoff system. Extending the living space outdoors, a covered patio overlooks the private grounds and is already pre-wired for cable and has a water line in place, providing a seamless opportunity to create the outdoor kitchen and entertainment area of your dreams. From the handcrafted architectural details to the thoughtful engineering and modern conveniences, no expense was spared in creating this truly exceptional residence. A rare opportunity to own a luxury home unlike anything else on the market.

225 Old Willets Path, 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

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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.