Smithtown Real Estate

Welcome to Smithtown, New York, a charming town nestled in the heart of Suffolk County on Long Island. Known for its rich history and vibrant community, Smithtown offers the perfect blend of suburban tranquility and urban convenience. With its picturesque landscapes, top-rated schools, and a variety of recreational activities, it’s no wonder that families, young professionals, and retirees alike are drawn to this delightful area.

Smithtown boasts a unique heritage, dating back to the 1600s when it was first settled by the Smith family. Today, remnants of its storied past can be seen in the town’s historic landmarks and charming architecture. The town is renowned for its beautiful parks, including the expansive Blydenburgh County Park, where residents can enjoy hiking, fishing, and picnicking amidst stunning natural scenery.

In addition to its outdoor attractions, Smithtown is home to a vibrant downtown area filled with local shops, cafes, and restaurants that cater to every palate. Whether you’re in the mood for a cozy brunch spot or a lively dinner with friends, you’ll find plenty of options to satisfy your cravings.

Smithtown’s strong sense of community is evident in its numerous events and festivals held throughout the year, fostering connections among residents and creating lasting memories. With easy access to major highways and the Long Island Rail Road, commuting to New York City is a breeze, making it an ideal location for those who work in the city but desire the serenity of suburban living.

Discover the charm of Smithtown, where a warm community spirit and a wealth of amenities await you!

Newest Listings in Smithtown

$775,000

3 Beds ⋅ 2 Baths ⋅ 1031716 MLS

WHERE TIMELESS CHARM MEETS EXCEPTIONAL OPPORTUNITY. Discover the warmth, character, and enduring appeal of this beautifully maintained Colonial, ideally situated in one of Smithtown’s most desirable neighborhoods. Rich hardwood floors, an inviting fireplace, and flowing floor plan create an atmosphere that feels instantly like home. Offering three spacious bedrooms and one-and-a-half baths, this residence features a gracious living room with fireplace, Dining room, and eat-in Kitchen. The partially finished basement provides abundant storage while offering potential for additional living space. Step outside and experience a setting that feels straight from the pages of a storybook. Meandering stone pathways weave through mature landscaped gardens, leading to an expansive fenced backyard that invites summer gatherings, outdoor celebrations, or simply peaceful evenings surrounded by nature. Perfectly positioned on a quiet residential street, this exceptional home offers the tranquility buyers seek while remaining just minutes from the Long Island Expressway, Northern State Parkway, shopping, dining, and all that the Town of Smithtown has to offer—including its renowned parks, beaches, and recreational amenities. Whether you’re searching for your forever home or a rare opportunity in one of Long Island’s most sought-after communities, this residence offers the perfect blend of charm, comfort, location, and future potential.

20 Brook Lane, Smithtown

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1030904 MLS

This Pristine Dream Home, Nestled on a Meandering Wooded Street in the Pines, is Ensconced in a Peaceful, Perennial Paradise! The Lushly Landscaped & Lovingly Tended Property, as Meticulous Outside as the Home is Inside, Compels you to Linger on the Covered Porch, just to drink in the View! Inside, a Grand Foyer Shines with its Soaring Ceiling, Stunning Imported Crystal Chandelier & Exquisite Custom Millwork, here & throughout the Home. Attention to Detail is Evident in each room, from the Elegant Formal Dining Room with Custom Window Seat to the Chef's Kitchen with new Stainless Appliances and Family Room w/ Garden Views for Summer & Fireplace for cozy Winters. The Radiant Heated Floors on this Floor Welcome the Colder Seasons! Ascend the Open Staircase to the Bedroom floor where sweet dreams are made in Lovely, Spacious Rooms. You begin and end each day gloriously, when your Primary Bedroom is your personal Suite Escape. The New, Custom Designed EnSuite is Resplendent in Marble with Tasteful Accents that Highlight the Soaking Tub & Glass Enclosed Shower in the Most Beautiful Way! This Home's Beauty is not only Seen, it's Felt...from the minute it beckons you in, you know you'll want to stay. If you Need More Practical Reasons to stay, here they are: The "Forever Slate" Metal Roof (home & shed), All New Andersen Windows, Whole House Generator, Whole House Water Filter System, 2 Zone Lennox Elite Central Air, Bosch High Efficiency Boiler & Tankless Water Heater, Electric Car Charger, Owned Solar Panels, Central Vacuum. Move-In Ready! The Season is Ideal to Enjoy All this Home has to Offer. Relax in the Garden, Entertain on the Patio, before the Autumn Colors & Snowfall Holidays begin. It's Time to Stop Dreaming and Start Living the Dream! Your Best Long Island Life Awaits!

35 Pine Ridge Drive, Smithtown

$699,999

3 Beds ⋅ 1 Baths ⋅ 1030650 MLS

Well maintained cozy ranch on tree lined street in Smithtown on .63 property with a detached garage. This home offers a formal living room, dining room, den, eat in kitchen, w/propane cooking as well as 3 bedrooms and 1 full bathroom. There are Anderson windows, hardwood floors in Living room.

42 Pineacre Drive, Smithtown

$825,000

4 Beds ⋅ 2 Baths ⋅ 1030021 MLS

Welcome Home to Unmatched Space & Craftsmanship in Smithtown! Nestled in the top-rated Commack School District, this meticulously maintained Hi-Ranch has been dramatically transformed by a huge 2-story extension, offering incredible size, flow, and modern luxury. Step inside to find rich hardwood floors and an open, light-filled layout. The expansive upper level culminates in a jaw-dropping Great Room designed for effortless entertaining, leading seamlessly out through double doors to a grand covered deck. Modern essential utilities include Central Air Conditioning and Natural Gas heating and cooking. Lower level offers immense flex space with bedroom, full bath, and family room. Step into a backyard paradise featuring a custom paver patio and built-in fire pit—ideal for cool nights under the stars. Conveniently located near top schools, parks, and major parkways. Turnkey living at its absolute finest!"

20 Hunter Place, Smithtown

$948,000

1029963 MLS

Exceptional owner-user opportunity in the heart of Smithtown! This well-maintained 1,683 SF professional office building is situated on a 10,890 SF lot with NB (Neighborhood Business) zoning. The first floor is ideal for an owner-occupant, while the income-producing lower-level tenant provides immediate rental income to help offset ownership costs. Conveniently located on Terry Road with easy access to major roadways, shopping, restaurants, and the Smithtown business district. A great opportunity for professional, medical, or service-related businesses seeking to own rather than lease, while benefiting from an existing income stream.

198 Terry Road, Smithtown

$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

$979,000

4 Beds ⋅ 3 Baths ⋅ 1029017 MLS

Under Construction – Your Opportunity to Own a Beautifully Renovated Home in Smithtown! Welcome to this stunning 4-bedroom, 2.5-bath splanch, currently under a full renovation with today's modern buyer in mind. Upon completion, this home will feature a spacious and modern layout with high-quality finishes throughout. With the main floor having a Beautiful modern kitchen and a formal dining room. Also a comfy den and half bath, The Second floor will have a very large living room/family room. Beautifully finished wood floors throughout with all new lighting and central air. New windows and crown moldings throughout. * Cover photo is an AI rendering of finalized renovation* On the 3rd floor The primary suite will include a full bath and walk in closet. The 3rd floor will also have a full bath plus 3 very large bedrooms The house also has a large fenced in yard perfect for entertaining! Finally beautiful landscaping finishes throughout will provide privacy and great curb appeal

30 Glacier Drive, Smithtown

$775,000

3 Beds ⋅ 2 Baths ⋅ 1027993 MLS

Welcome home! This pristine 3-bedroom, 2-bathroom Splanch sits perfectly on a flat, fenced .25-acre lot in a sought-after, sidewalk-lined neighborhood. Beautifully merging modern updates with exceptional energy efficiency, this residence is entirely turn-key. From the moment you arrive, the new double-wide paver driveway provides the convenience for parking multiple cars without the chaos. Enjoy the newer kitchen and updated bathrooms. Bright sliders lead directly from the home to a brand-new deck, perfect for summer barbecues and outdoor dining or relax by the warm gas fireplace in your inviting main living space. Stay comfortable year-round with efficient gas heating and central air conditioning in a home that is fully equipped with solar panels to drastically lower your monthly electric bills. This property is situated in the Smithtown School District. It offers easy access to the town's Main Street, dining, and shopping, as well as gorgeous state and county parks. Commuting is effortless and convenient to major highways and the Long Island Rail Road (LIRR). Everything you could want is waiting for you right here.

11 Sandalwood Drive, Smithtown

$725,000

3 Beds ⋅ 3 Baths ⋅ 1028158 MLS

Welcome to Hidden Ponds, a beautiful gated community in the heart of Smithtown. This end-unit townhouse offers the perfect combination of comfort, style, and convenience with 3 spacious bedrooms, 2.5 bathrooms, and natural gas heating and cooking. The welcoming open-concept main level features a beautifully renovated eat-in kitchen with stainless steel appliances, a massive center island, abundant pantry storage, and seamless flow into the living and dining areas. Hardwood flooring extends throughout the first floor, which also includes a laundry room, powder room, and attached garage. Sliding glass doors lead to a private composite deck overlooking the peaceful greenbelt path, while established flower gardens add charm and privacy. The Upstairs, the expansive primary suite offers a private ensuite bathroom, two walk-in closets, and a versatile office or flex space. Two additional generously sized bedrooms, a full bathroom, and soaring vaulted ceilings complete the second level. Residents of Hidden Ponds enjoy exceptional amenities, including a clubhouse with a kitchen, movie/card room, fitness center, outdoor pool, tennis and pickleball courts, basketball court, bocce ball, playground, mailroom, extended driveway, and ample guest parking. Experience the perfect blend of comfort, convenience, and resort-style living in one of Smithtown’s most desirable gated communities.

300 Pond View Lane, Smithtown

$3,995,000

7 Beds ⋅ 6 Baths ⋅ 1022766 MLS

Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.

38 Landing Meadow Road, Smithtown

$985,000

4 Beds ⋅ 3 Baths ⋅ 1028029 MLS

Welcome home to this stunning, meticulously maintained Colonial in the renowned Commack school district. Thoughtfully expanded with additional living space, this home offers room to grow, entertain, and unwind in style. Step outside into your own entertainer's paradise — a country club-worthy backyard featuring a sparkling saltwater in-ground pool (complete with a brand-new pump). Inside, quality craftsmanship shines throughout: gleaming hardwood floors, a cozy fireplace, energy-efficient Andersen windows, recessed lighting, and a sun-drenched skylight create a warm, elevated living experience. The spacious basement offers even more flexible space for a home gym, media room, or playroom. Outside, practicality meets curb appeal with a double-wide driveway, electric garage door opener, and three sheds for all your storage needs.

29 Sandy Hollow Drive, Smithtown

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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.