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$905,000
4 Beds ⋅ 3 Baths ⋅ 1032833 MLS
Pristine and sophisticated, this beautifully customized 4-bedroom, 2.5-bath ranch offers a spectacular open-concept design perfect for today's lifestyle. Originally built in the 1960s, the home has been thoughtfully updated over the years to reflect timeless elegance and exceptional craftsmanship. The stunning center island kitchen features a dramatic 7-foot black granite island, Sub-Zero refrigerator, Bosch dishwasher, GE appliances, under-counter microwave, and cooktop. Hardwood floors and custom built-ins enhance the home's warmth and character, while the spacious living and entertaining areas flow seamlessly to the rear deck for effortless indoor-outdoor living. A truly special home that is impeccably maintained and a must see.

22 S Lot Road, Smithtown
$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
$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, 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
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 1023260 MLS
Welcome to 20 Oak Tree Drive in the highly desirable Village of the Branch. Proudly offered by the original owners, this lovingly maintained 4-bedroom, 3-bath ranch has been cherished for many years and showcases true pride of ownership throughout. Set on a beautifully landscaped, park-like property, this spacious home offers comfortable one-level living with a functional floor plan designed for both everyday living and entertaining. Generously sized rooms, abundant natural light, a partial basement for additional storage or recreational space, and a two-car garage provide the perfect combination of comfort and convenience. With multiple living areas and a flexible layout, this home offers excellent potential for extended family living or a private space for Mom. Two separate entrances lead to the beautiful backyard, creating added convenience and versatility. Step outside and enjoy the stunning grounds, perfect for entertaining, gardening, or simply relaxing in your own private retreat. The mature landscaping and peaceful setting make this property truly special. Conveniently located near shopping, dining, parks, transportation, and all that Smithtown has to offer, this is a rare opportunity to own a well-cared-for home in one of the area’s most sought-after communities. Come see why this exceptional property has been loved and meticulously maintained by the same family for decades.

20 Oak Tree Drive, Smithtown
$1,374,000
4 Beds ⋅ 3 Baths ⋅ 1014247 MLS
Welcome to one of the most impressive properties to hit the market in The Pines. Set on a private half-acre of beautifully manicured grounds, this extraordinary contemporary ranch offers a perfect blend of luxury, comfort, and resort-style living—all in a beautifully landscaped, private setting. A long paved driveway leads to a spacious two-car garage and a grand entry foyer with soaring vaulted ceilings that create an unforgettable first impression. Inside, rich hardwood floors, custom moldings, skylights, and high-hat lighting create a warm, elegant ambiance, while central air conditioning throughout ensures year-round comfort. The sun-filled living room, highlighted by a stunning stone fireplace and skylights, features vaulted ceilings that enhance the open, airy feel. The formal dining room sets the stage for unforgettable gatherings. At the heart of the home is a breathtaking chef’s kitchen—boasting a massive granite island, farmhouse sink, custom cabinetry, premium Thermador appliances, and a bright dining area with a tray ceiling and a bow window overlooking the backyard oasis. Sliding glass doors open to a covered Trex porch, a patio, and a pool area—perfect for entertaining or unwinding. The luxurious primary suite is a true retreat—featuring a spa-inspired bath with vaulted ceilings, a jetted shower, and a spacious walk-in closet. The home also includes three full baths, a wet bar with a wine cooler, a mudroom with abundant storage, California closets, and a finished lower level with heating, air conditioning, egress windows, and a large walk-in closet. And then, there’s the backyard. This is your private resort—complete with a spectacular 40-by-20 heated pool, rock waterfall, integrated spa, and complete privacy thanks to specimen plantings, landscape lighting, and PVC fencing. With a covered Trex porch, oversized storage shed, and a commercial-grade Generac whole-house generator, this home is a haven of comfort and convenience. Move-in ready and impeccably maintained—this is a rare opportunity to own a slice of paradise. Don’t miss out—this dream home won’t last long!

6 Averly Place, Smithtown
$799,803
4 Beds ⋅ 3 Baths ⋅ 1012271 MLS
Sprawling Ranch Situated On A Beautiful Half-Acre Property In The Heart Of Smithtown. This Well-Maintained Home Features 4 Bedrooms, 3 Full Baths, Hardwood Floors, Spacious Living Areas, And A Finished Lower Level With Outside Separate Entrance Offering Flexible Space For Recreation, Hobbies, Guests, Or Extended Living Needs. The Eat-In Kitchen Showcases Cherry Wood Cabinetry, Granite Countertops, And Ample Space For Everyday Dining And Entertaining. Enjoy A Formal Dining Room, Wood-Burning Fireplace, 16 x32 In-Ground Saltwater Pool With Outdoor Shower, Paver Patio, Deck, And Mature Landscaping. Additional Features Include In-Ground Sprinklers, Smithtown Water, Attached Garage, And Updated Systems. The Flexible Floor Plan Includes A Possible Fourth Bedroom Or Home Office To Suit Your Needs. Conveniently Located Near Shopping, Restaurants, Parks, And Transportation. Tax grievance letter is to inform you that we are in the process of professionally grieving the taxes at the above address. Based on our analysis indicates annual property tax reduction of approximately $3,200 a year. (Please see attached letter) If the case is won, a reduction would take place for the 2027/2028 tax year.. Move Right In And Enjoy Everything This Exceptional Property Has To Offer.

9 Dillmont 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
$762,990
3 Beds ⋅ 2 Baths ⋅ 1015455 MLS
Disclaimer: Agent Owned Property Note: Some listing photos have been virtually staged 28 Dartmouth Drive sits in College Estates, one of Smithtown's most established neighborhoods. Quiet streets, strong neighbors, and one of Long Island's top-rated school districts right outside your door. The home has been thoughtfully maintained and strategically updated where it counts. The home received a full house-wide plumbing replacement and renovated primary bath in 2024, followed by a new furnace and water heater in 2025. While most homes in this price range and era are carrying decades-old systems, this one is not. The home is on natural gas service throughout. Inside, the main floor flows from a formal living room into a separate dining room, den, and eat-in kitchen, well-proportioned spaces filled with natural light from original Anderson windows. The south-facing front of the home draws sun through the main living spaces for most of the day. Hardwood floors and handcrafted wood finishes run throughout, giving the home a warmth and character that's hard to manufacture. Central air keeps things comfortable year round. A bonus room off the main living area works equally well as a home office or extra bedroom. The finished basement adds close to 1,000 square feet of additional space, suited for a home gym, media room, extended family setup, or serious storage. A Cambridge paver stoop greets you at the front entry and a one-car garage rounds out the package. The backyard is private and generous. A quarter-acre lot enclosed by mature trees with one beautiful old anchor tree at the center that gives the space a presence most yards don't have. Minutes to town beaches on the Nissequogue River, Avalon Nature Preserve, Stony Brook University Hospital, downtown Smithtown, and Port Jefferson village. Quick access to the LIE, Route 347, and the St. James LIRR station. Smithtown East school district.

28 Dartmouth Drive, Smithtown
$775,000
3 Beds ⋅ 3 Baths ⋅ 1014086 MLS
***Located in the desirable Smithtown Pines area and within the Hauppauge School District, this spacious 3-bedroom, 3-full-bath ranch is set high on a picturesque half-acre property and offers tremendous potential for customization.Spacious 3-bedroom, 3-full-bath ranch offers incredible potential and a flexible floor plan ready for your personal touch. Featuring vaulted ceilings and an open-concept layout, the kitchen flows seamlessly into the living room, where a fireplace serves as the centerpiece of the space. The home also offers a formal dining room and a separate family room, providing plenty of room for everyday living and entertaining. The full finished basement with outside separate entrance (OSE) adds valuable additional living space and presents endless possibilities for recreation, a home office, guest accommodations, or extended family. Set on a generous, elevated lot, the property boasts both an attached 2-car garage and a detached 2-car garage—an uncommon feature ideal for car enthusiasts, hobbyists, or those seeking ample storage and workspace. Create your dream residence in a desirable setting with great bones, abundant space, and exceptional potential. Bring your vision and make this property truly your own.

61 Ledgewood Drive, Smithtown
$725,000
5 Beds ⋅ 3 Baths ⋅ 984398 MLS
Welcome to 20 Veronica Court, Smithtown — a spacious ranch-style home nestled on a quiet cul-de-sac in a desirable residential setting. This 5-bedroom, 3-bathroom ranch offers comfortable single-level living with additional space to grow. The primary bedroom features a private en-suite bathroom and direct access to its own secluded deck — the perfect spot to enjoy your morning coffee or unwind in the evening. The home also boasts a second deck off the kitchen, ideal for outdoor dining and entertaining in the backyard. A full basement expands the home’s versatility, complete with an additional bedroom and bathroom, providing excellent potential for extended living space, guests, or recreational use. The property offers solid bones and a functional layout, while presenting a great opportunity for buyers to add their personal touches and updates to make it truly their own. Located on a peaceful cul-de-sac, this home combines privacy, convenience, and potential — all within close proximity to shopping, dining, parks, and major roadways.

20 Veronica Court, 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.