Smithtown Real Estate

Welcome to Smithtown, a vibrant community nestled in the heart of Suffolk County, New York. Known for its picturesque landscapes and rich history, Smithtown is not just a beautiful place to live; it’s also home to an exceptional school district that prioritizes the education and development of its students.

The Smithtown Central School District is renowned for its commitment to academic excellence, offering a comprehensive curriculum that caters to diverse learning styles. With a strong emphasis on both academics and extracurricular activities, students are encouraged to explore their interests and talents. From advanced placement courses to a wide range of sports and arts programs, Smithtown schools provide a well-rounded educational experience that prepares students for future success.

Parents will appreciate the dedicated staff and innovative teaching methods that foster a nurturing environment. The district boasts a high graduation rate and a strong college readiness program, ensuring that students are not only prepared for high school but also for the challenges of higher education. Community involvement is highly encouraged, with numerous events and programs that connect families and educators, creating a supportive network for students.

The picturesque town of Smithtown itself offers a charming blend of suburban tranquility and easy access to urban amenities. With beautiful parks, shopping, and dining options nearby, families can enjoy all that this welcoming community has to offer. Whether you're looking for a place to raise a family or simply seeking a vibrant community, Smithtown’s exceptional school district is just one of the many reasons to call this area home. Explore the possibilities in Smithtown today!

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

$725,000

4 Beds ⋅ 3 Baths ⋅ 1031693 MLS

Welcome to this beautifully expanded Cape nestled in a lovely neighborhood in Nesconset within the highly desirable Smithtown School District! Thoughtfully designed for both everyday living and entertaining, this home offers an abundance of space and timeless charm. The heart of the home is the expansive, open-concept first floor featuring a stunning 5 year old kitchen with granite countertops, , double ovens-one with built-in air fryer, stainless steel appliances, a farmhouse sink, gas cooking, pendant lighting, breakfast bar seating, and an abundance of cabinetry. The kitchen flows seamlessly into the dining area, where a gorgeous wood burning stone fireplace creates a warm and inviting atmosphere for family meals and gatherings. A spacious living room where you can also enjoy the cozy fireplace offers the perfect place to relax year-round. The first floor also includes a versatile bedroom that can easily serve as a home office or guest room, along with sliding glass doors that lead to a large deck overlooking the backyard—ideal for outdoor entertaining. Upstairs, the spacious primary bedroom is complemented by a beautifully updated full bath featuring a walk-in shower. Two additional generously sized bedrooms and a hall bathroom with a tub provide plenty of room for family and guests. Car enthusiasts, hobbyists, or those needing extra workspace will appreciate the detached two-car garage, complete with electric and air conditioning. An expanded driveway offers ample parking for multiple vehicles and guests. Additional highlights include a formal dining room for hosting holiday celebrations and special occasions. Home has 4 heat zones, 200 amp electric and Luxury vinyl planking, along with a prime location close to shopping, restaurants, and everyday conveniences Enjoy all the wonderful amenities the Town of Smithtown has to offer, including beautiful parks, recreational facilities, and exclusive access to the Town's private North Shore beaches. This exceptional home combines space, comfort, and location—making it the perfect place to call home.

21 Wilson Avenue, Nesconset

$399,000

1 Beds ⋅ 1 Baths ⋅ 1030363 MLS

Welcome to 1203 Cabot Court, the greatest opportunity in one of Long Island’s most sought-after 55+ developments located in the heart in historic Saint James. This condo features 1 bedroom and 1 full bath. Design your own open layout to your personal taste. Plan where to locate your in-unit laundry & central air vents! Sliding glass doors lead to a private patio plus attached garage with storage & shared driveway with one space. The Fairfield at Saint James community provides resort-style amenities including a clubhouse, fitness center, basketball, tennis & new pickleball courts. Enjoy swimming no matter the season! The indoor pool is open during the winter season & two outdoor pools are open during the summer season. Residents enjoy a vibrant social calendar, there are beautifully manicured grounds, well maintained blacktop trails and benches run throughout this lush community affording residents ability to take in the lake views and water features throughout this secure gated community. The Fairfield which has 675 units built from the early 1970's throughout the 1990's offers low common charges, low taxes and is close proximity to Smith Haven Mall shopping, top dining, golf, Award Winning Stonybrook Hospital 4.7 miles away, beautiful North Shore beaches & major highways. Only 2.1 miles to Saint James LIRR Station for an easy commute to Manhattan. One can experience a comfortable lifestyle within a 30 minute drive to vineyards, farmstands & seasonal resorts throughout the coveted North Fork of Long Island. This opportunity of a lifetime will not last long!

1203 Cabot Court, Saint James

$499,000

2 Beds ⋅ 2 Baths ⋅ 1031076 MLS

Welcome to Fairfield at St. James, a desirable 55+ gated community! This spacious first-floor corner condo offers 2 bedrooms and 2 full baths with no one above. Enter into a foyer with large coat closet from your covered front porch. Enjoy an eat-in kitchen with stone countertops, dishwasher and electric oven with Microwave hood. A formal dining room comfortably fits a large table to seat 6+ and hutch. Spacious living room with sliders to a private patio. This unit has an in-unit washer and dryer, central air and electric heat. The patio features an awning and a charming garden area. Ideally located directly across from the clubhouse, pool and tennis courts!

302 Bentley Court W, Saint James

$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

$860,000

4 Beds ⋅ 3 Baths ⋅ 1030391 MLS

You must see the amazing layout of this sprawling 4 bedroom, 2 1/2 bath ranch with a separate office, nestled on a beautiful .52-acre property in the desirable Smithtown School District. With the bedrooms just a few steps up from the main living area, it has all the great features of a ranch while providing privacy from the main floor. From the moment you step through the front door, the beautiful foyer sets the tone for the spacious, welcoming feel found throughout. The main level offers wonderful one-floor living, with a formal living room, formal dining room, an expansive den, and a dedicated home office. The eat-in kitchen features granite countertops and stainless appliances with direct access to the deck, backyard and pool area. Just a few steps up, you'll find four comfortable bedrooms and two full baths, including a large primary suite complete with a sunken tub and walk-in closets — a true retreat at the end of the day. A full, partially finished basement adds even more flexible living and storage space. Outside, the backyard is made for entertaining and relaxing alike. Take a dip in the gunite inground pool with a waterfall feature, unwind on the back deck, and enjoy the ease of an inground sprinkler system keeping the grounds lush. A 3-car attached garage and circular driveway offer plenty of room for parking and storage. Gas heat, central air conditioning, and public sewer round out the home's practical comforts. Homes with this much space, on a lot this size, in this location, don't come along often.

29 Ivy Hill Drive, Hauppauge

$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

$799,000

4 Beds ⋅ 2 Baths ⋅ 1029526 MLS

Welcome Home To This Legal Mother Daughter & Beautifully Constructed Nesconset Colonial Nestled On An Expanded Corner Lot In The Award Winning Smithtown School District Featuring 4 or 5 Bedrooms, 2 Full Bathrooms, Welcoming Entry Foyer, Eat-In Kitchen w/ 3 Skylights, Granite Countertops & Double Sliders Leading Out To Back Deck, Hardwood Floors Throughout, Central AC, Full Basement w/ Tons Of Storage, New Roof, One Car Attached Garage, In-Ground Sprinklers & A Private Resort-Like Backyard w/ Oversized In-Ground Pool Perfect For Entertaining And/Or Relaxing, Plus Much, Much More! You Do Not Want To Miss This One!

26 Heritage Place S, Nesconset

$1,489,999

4 Beds ⋅ 4 Baths ⋅ 1027742 MLS

Welcome to 21 Wilderness Road, an exceptional Colonial set on two private acres in the Village of Nissequogue, where timeless design and thoughtful updates come together in a private, serene setting. Offering 4 bedrooms and 4 bathrooms, this residence delivers generous living spaces, refined finishes, and effortless everyday comfort. Hardwood floors, detailed crown molding, and an inviting floor plan create a warm yet elegant atmosphere throughout. The updated kitchen is appointed with granite countertops, abundant cabinetry, and flows seamlessly into the main living areas, making it ideal for both entertaining and everyday living. A fireside sitting area offers the perfect place to gather, while a dedicated home office provides the flexibility to function as a fifth bedroom, guest suite, or private study. One of the home’s most desirable features is its private deeded access to the pristine Long Island Sound, where scenic water views and shoreline access offer an exceptional coastal lifestyle. Additional highlights include an oversized two-car garage with attic storage, a newer Peerless boiler with a Riello burner, and an indirect hot water system for added efficiency. Surrounded by mature trees and lush landscaping, yet just minutes from the Nissequogue Golf Club, scenic nature preserves, and the charming village of St. James, this exceptional property offers a rare opportunity to enjoy privacy, recreation, and coastal living in one of Long Island’s most distinguished waterfront communities.

21 Wilderness Road, Nissequogue

$649,000

3 Beds ⋅ 2 Baths ⋅ 1028618 MLS

Charming 3-bedroom, 2-full-bath ranch in the heart of Nesconset! Lovingly maintained and ready for its next chapter, this home offers a functional layout, a private backyard, and endless potential to make it your own. Conveniently located near shopping, restaurants, parks, and major roadways. Don’t miss this wonderful opportunity!

150 Shenandoah Boulevard N, 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.