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$725,000
6 Beds ⋅ 2 Baths ⋅ 1038388 MLS
Welcome to this beautifully and completely updated expansive home in renowned Smithtown school district. This home is thoughtfully designed for modern living and multigenerational flexibility. The home features a private separate entry setup, ideal for an in-law suite, or extended family. The interior has been extensively updated with finishes throughout, including beautiful, refinished hardwood floors, and a sophisticated kitchen featuring quartz countertops. The spacious layout provides an abundance of room for entertaining, relaxing, and everyday living. Also, upstairs features two spacious walk-in closets Outside, enjoy multiple patios and decks that create exceptional outdoor living and entertaining spaces. Two separate driveways provide generous parking and added convenience the one driveway is shared adjoining with the neighboring property plus a huge separate private driveway on the other side of the property. In addition, the property is located on almost 1/2 acre. A rare combination of size, style, flexibility, and functionally, this exceptional property is ideal for buyers seeking a move in home with room for everyone.

653 Meadow Road, Smithtown
$769,803
4 Beds ⋅ 3 Baths ⋅ 1037822 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
$1,649,000
5 Beds ⋅ 4 Baths ⋅ 1037441 MLS
Welcome to this beautiful 5 bedroom 3.5 Bath Colonial perfectly positioned on a quiet cul-de-sac set within Yellow Top Estates, a rare gated enclave of luxury single-family homes. From the covered front porch and beautiful paver and asphalt driveway to the 3-car garage, this home makes an incredible first impression. Enter inside to a dramatic two-story entry foyer with soaring ceilings, beautiful moldings and hardwood floors throughout. The spacious living room features custom built-ins surrounding a gas fireplace, creating the perfect place to gather and relax. The completely renovated kitchen is truly the heart of the home, featuring quartz countertops, a gas range, double ovens, wine fridge and plenty of space for entertaining. A private office or 5th bedroom is perfectly situated away from the main living areas, offering great flexibility for guests or working from home. Upstairs, the spacious primary suite is a true retreat with a beautifully appointed primary bath, including a soaking tub overlooking the backyard. And the backyard is where this home really shines. Designed for resort-style living, it features a freeform saltwater inground pool surrounded by beautiful pavers, an incredible outdoor kitchen with a gas grill, gas pizza oven, granite countertops and an oversized bar ready for summer BBQs and entertaining. A covered Trex deck offers the perfect spot to relax and enjoy the private setting, while a separate hot tub provides the perfect place to unwind and can be enjoyed year-round. Lovingly maintained, thoughtfully updated and ideally located within Yellow Top Estates. Don't miss this special home!

6 Hayloft Court, Smithtown
$765,000
3 Beds ⋅ 3 Baths ⋅ 1036970 MLS
Welcome to Smithtown Pines! I am excited to share this beautifully maintained 3-Bedroom, 2.5-Bathroom Colonial home which was totally rebuilt from the foundation up in 2003 with a full basement. The exterior features a charming covered porch and a deep backyard complete with a large deck and a pond, perfect for outdoor relaxation. Inside, the first floor boasts a Living Room with a dual-sided gas fireplace that opens into the Dining area, which features sliding glass doors. The large Kitchen comes equipped with stainless steel appliances and leads to a convenient Mudroom featuring a stackable washer/dryer, a side entrance, and a half bath. The second floor offers a Primary Bedroom with two large closets and a spacious bathroom featuring a large Tuscan shower, alongside two additional generously sized bedrooms. Additional features include oil heat, an inground sprinkler system, and completed ductwork ready for central air conditioning.

149 Grassy Pond Drive S, Smithtown
$749,990
3 Beds ⋅ 2 Baths ⋅ 1036406 MLS
Nestled on over half an acre of beautifully manicured property, 271 Terry Road in Smithtown offers charm, flexibility, and exceptional indoor-outdoor living. This well-maintained home features a thoughtfully designed layout with a finished basement that includes a private outside entrance, a full designer bathroom, office space, additional living area, laundry area, wet bar, walk-in closet, extra storage, and direct access to the backyard - ideal for extended living, guests, or work-from-home flexibility. The main floor offers a warm and inviting flow with a kitchen, two bedrooms, full bathroom, dining room, and living room with a wood-burning fireplace. Additional highlights include a front deck, beautiful breezeway for memorable family gatherings, a detached garage, and a stunning backyard retreat complete with a pool and plenty of room to entertain, relax, and enjoy the property. This home combines comfort, versatility, and outdoor beauty in a desirable Smithtown location

271 Terry Road, Smithtown
$875,000
4 Beds ⋅ 4 Baths ⋅ 1035540 MLS
Colonial located in the desirable Smithtown Hillside (formerly known as Royal Woods). Welcome to this well-maintained 4-bedroom, 3.5-bathroom This spacious home offers a wonderful combination of comfort, functionality, and entertaining space. The inviting step-up living room features vaulted ceilings, a sunburst window, and an abundance of natural light. The formal dining room is ideal for entertaining, while the eat-in kitchen offers granite countertops, a bay window, and a convenient outside entrance. A first-floor mudroom/laundry room provides added everyday convenience, along with a powder room. The comfortable den features a wood-burning fireplace and sliders leading to the peaceful, fully fenced backyard with patio—perfect for relaxing, dining, or entertaining. The finished basement provides an impressive amount of entertaining space, including a bar area, recreation room, counter set up with refrigerator, full bathroom, workshop, storage area, and outside entrance. The layout offers possible mother-daughter potential with proper permits. Additional features include 200-amp electric, six-panel solid interior doors, an above-ground galvanized oil tank, water filtration system in the kitchen, and a cesspool located in the front yard with drywell. The second-floor full bathroom features marble tile, radiant heat, a heat lamp, and vaulted ceiling with sunburst window (radiant heat not making representation and needs battery) jacuzzi tub w/colorful lighting. The home also offers a full attic with flooring, pull-down stairs, and electric, a Pearson heating system installed in 2018, and 6-zone in-ground sprinklers. Smoke detectors installed with Lithium Batteries. House is wired with Fiber Optics. A wonderful opportunity to enjoy spacious living, versatile finished space, and a desirable location in Smithtown.

26 Sheryl Crescent, Smithtown
$719,990
4 Beds ⋅ 3 Baths ⋅ 1036165 MLS
Expanded ranch featuring 4 bedrooms, 3 full baths, and a finished basement. Open floor plan with hardwood floors and central air. Den with sliding doors opens to an oversized yard with a private patio and in-ground pool, perfect for entertaining. Tucked away on a private cul-de-sac.

58 Crescent Place, Smithtown
$999,000
4 Beds ⋅ 4 Baths ⋅ 1036045 MLS
Welcome to this beautifully renovated 4-bedroom, 4-bathroom home in the heart of Smithtown! This move-in-ready property features a thoughtfully designed open floor plan, a stunning modern kitchen, spacious living areas, and fully updated bathrooms throughout. Guest Suite with private bathroom allows for flexible living options. The finished basement offers exceptional additional living space, perfect for a kid's recreation room or a home office. Situated in a desirable neighborhood close to parks, shopping, dining, and top-rated Smithtown schools, this home combines quality craftsmanship, modern finishes, and everyday comfort. A rare opportunity you won't want to miss!

30 New Mill Road, Smithtown
$599,999
3 Beds ⋅ 1 Baths ⋅ 1035638 MLS
Incredible opportunity to make this ranch in Smithtown SD your own! Eat in kitchen with entrance to back patio. Hardwod floors under carpets confirmed by seller. Garage converted into Den. Living room or dining room . 3 spacious sunlit bedrooms and a full bath with window. Light and bright. Great location! Full Unfinished basement with laundry. Wonderful flat property. Fenced in yard. Oil Heat. Quiet tree lined street. Close to all!

1 Dale Lane, Smithtown
$689,888
3 Beds ⋅ 2 Baths ⋅ 1022617 MLS
Nestled in the heart of Smithtown on a spacious .38 acre lot (two .19 acre lots) this charming Cape Cod offers a perfect blend of classic appeal and modern convenience. Inside, you’ll find beautiful hardwood and vinyl flooring throughout, a cozy wood burning fireplace and a welcoming Dutch door entry that opens into a functional mudroom. The kitchen is designed for both style and efficiency, boasting elegant cabinetry with pull out drawers and a hidden snack drawer. The flexible floor plan includes three bedrooms, including a primary suite with dual closets and a versatile bonus room, making the home ideal for those seeking a private guest suite or in law plan. Practicality is a priority here, with a 2025 roof, 200 amp electrical service, a hardwired generator, a whole house water filtration system and split unit cooling. The property also includes an OVERSIZED one car garage with ample storage space and a full basement that features a convenient outside entrance located at the top of the stairs. The exterior serves as your own private oasis. Head through the new sliders with built in blinds onto an awning covered Trex deck, where you can enjoy serene views of two ponds and stunning landscaping. The backyard is highlighted by an in ground gunite pool recently resurfaced, surrounded by a cool deck, perfect for summer entertaining. With an unbeatable location that allows for a car free lifestyle, just a short distance from local theaters, shopping, nightlife, parks, Whole Foods, Trader Joe’s and the Smithhaven Mall. This home is a rare find that truly has it all!

112 Lawrence Avenue, Smithtown
$635,000
4 Beds ⋅ 2 Baths ⋅ 1034371 MLS
Welcome to this well-maintained 4 bedroom, 1-1/2 bath brick ranch in East Hills Estate offering approximately 1600 square feet of comfortable single-level living space. Features include central air conditioning, basement which can provide additional living and/or recreational space. Hot water heater is one year young with central air conditioning under 8 years. Ideally located in the Smithtown area. Enjoy the benefits of close proximity to shopping, restaurants, and parks. A wonderful opportunity to make this home your own!

29 Penn Drive, Smithtown
$679,000
3 Beds ⋅ 2 Baths ⋅ 1034437 MLS
Absolutley beautiful three-bedroom, two full bath cape situated on a generous lot in the heart of Smithtown. This move-in-ready home showcases a newer roof, stylish luxury vinyl plank flooring, a beautifully updated bathroom (2026), and a bright eat-in kitchen designed for both everyday living and entertaining. The flexible floor plan offers three spacious bedrooms and two full baths and a versatile loft space, providing plenty of room for family, guests, or a home office. The attractive board-and-batten vinyl siding adds timeless curb appeal and enhances the home's modern farmhouse charm. The oversized property offers endless possibilities for outdoor entertaining, gardening, recreation, or future expansion. Conveniently located near parks, shopping, restaurants, schools, and transportation, this beautifully updated home combines comfort, style, and convenience and is just waiting for its next owner.

22 South Avenue, Smithtown
$1,199,999
4 Beds ⋅ 3 Baths ⋅ 1031008 MLS
Once-in-a-lifetime opportunity to own this spectacular custom-built Colonial, completed in 2022 and perfectly positioned on an incredibly private three-quarter-acre property within the highly desirable Smithtown School District. Tucked away at the end of a long private driveway, this exceptional estate offers the perfect combination of luxury, privacy, and resort-style living. A sprawling blacktop driveway with elegant Belgian block edging provides parking for multiple vehicles, boats, RVs, and recreational toys, while custom stone retaining walls, professionally manicured landscaping, a one-car detached garage with electric, cedar impression siding, and a cultured stone facade create breathtaking curb appeal. The backyard is truly a private resort, featuring a stunning custom in-ground swimming pool with a dramatic waterfall, natural stone diving rock, expansive Cambridge-style paver patios, multiple entertaining areas, and beautifully landscaped grounds designed for unforgettable gatherings. A welcoming covered front porch leads to a grand entry highlighted by gleaming hardwood floors, custom crown molding, decorative wall moldings, modern lighting, solid one-piece interior doors, and exceptional craftsmanship throughout. The elegant formal living room is flooded with natural light and showcases a spectacular cultured stone gas fireplace accented by custom sconces and recessed lighting. The heart of the home is the magnificent eat-in chef’s kitchen, thoughtfully designed for both everyday living and entertaining guests, featuring quartz countertops, an oversized breakfast bar illuminated by designer globe pendant lighting, custom cabinetry with under-cabinet lighting, a decorative tile backsplash, premium stainless steel Bertazzoni refrigerator, Bertazzoni gas range, built-in microwave, dishwasher, recessed lighting, surround sound, and sliding glass doors leading directly to the backyard oasis. Whether preparing a quiet dinner or hosting large gatherings, this kitchen is sure to impress. Custom blinds throughout the home add style and privacy. The flexible first-floor layout includes a spacious fourth bedroom or home office with direct access to a beautifully appointed Jack-and-Jill full bathroom featuring a white vanity and glass-enclosed shower, making it ideal for guests or remote work.. Soaring 9-foot ceilings throughout the first and second floors create an open, airy feel. Upstairs, the luxurious primary suite serves as a true retreat with recessed lighting, ceiling fan, custom crown molding, abundant natural light, a spa-inspired bathroom featuring a double vanity, oversized glass-enclosed shower with designer tile, recessed lighting, and an incredible custom walk-in closet complete with built-in cabinetry, drawers, shelving, bench seating, and abundant hanging space. Two additional generously sized bedrooms offer spacious closets and share a beautifully finished hallway bathroom with a glass tub and shower enclosure. A convenient second-floor laundry room includes front-loading Electrolux washer and dryer. The impressive wood staircase with custom metal balusters adds another level of sophistication. The ground-level bonus space offers endless possibilities with high ceilings, a private entrance, abundant natural light, and flexible living space ideal for a den, media room, home gym, office, guest quarters, or extended family. Additional amenities include a walk-up attic for storage, in-ground sprinklers, an alarm system, exterior security cameras, two-zone central air conditioning, surround sound, and countless custom upgrades throughout. Every inch of this extraordinary home has been thoughtfully designed with quality finishes, timeless style, and exceptional attention to detail, creating a rare opportunity to own one of the finest newer construction homes in the highly sought-after Smithtown School District.

79 Oakside Road, Smithtown
$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
$699,990
4 Beds ⋅ 2 Baths ⋅ 1031895 MLS
Prime Location with Limitless Potential! ?Welcome to this spacious 4-bedroom home situated in a highly desirable neighborhood within the Smithtown Central School District. Offering a perfect canvas for your vision, this property boasts incredible potential for updates and customization. ?Key Highlights: ?Spacious Layout: 4 generously sized bedrooms ready for your personal touch. ?Prime Location: Minutes from local shopping, dining, parks, and schools. ?Outdoor Space: An expansive, completely flat backyard—ideal for entertaining, play, or adding a pool. ?Bring your vision and make this home your own!

4 Smithtown Crescent, 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 or Back Patios, 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 Fine 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 with it's Generous Landing & Lovely, Spacious Rooms. Look forward to beginning & ending each day, 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 reasons to stay, here they are: The "Forever Slate" Metal Roof w/ Transferable Lifetime Warranty (home & shed), All New Andersen Windows (20 Yr Transferable Warranty), 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, Indoors & Out. Relax in the Garden & Entertain on the Patios, before the Autumn Colors & Snowfall Holidays begin. Isn't it 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
$800,000
4 Beds ⋅ 3 Baths ⋅ 1030391 MLS
Sprawling Smithtown Ranch on .52 Acre with Gunite Pool & 3-Car Garage! Space, flexibility and a backyard built for summer living come together in this distinctive 4-bedroom, 2.5-bath home set on a beautiful .52-acre property in the desirable Smithtown School District. Offering the ease and open feel of ranch-style living with a thoughtfully designed split-level bedroom wing, this home provides an exceptional layout for both everyday living and entertaining. A welcoming foyer opens to generously sized living spaces, including a formal living room, formal dining room, expansive den and a separate home office—ideal for working from home or creating a quiet flex space. The eat-in kitchen features granite countertops, stainless steel appliances and direct access to the deck, backyard and pool, making indoor-outdoor entertaining easy. Just a few steps above the main living area are four bedrooms and two full baths, creating separation and privacy without sacrificing the convenience of a ranch-style layout. The spacious primary suite features walk-in closets and a private bath with a sunken tub. The partially finished basement provides additional flexible space along with plenty of storage. Outside is where this property truly shines. Enjoy more than half an acre with a gunite inground pool and waterfall feature, a spacious deck for outdoor dining and entertaining, and an inground sprinkler system. A circular driveway and rare 3-car attached garage provide abundant parking and storage. Gas heat, central air conditioning and public sewer add to the home's everyday comfort and convenience. If you've been searching for generous living space, a private backyard retreat and an exceptionally versatile layout in the Smithtown School District, 29 Ivy Hill Drive deserves a closer look.

29 Ivy Hill 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
$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
$799,900
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 20 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
$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
$949,999
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
$1,699,000
5 Beds ⋅ 6 Baths ⋅ 1027754 MLS
Experience the pinnacle of luxury living on this sprawling 1.25+ acre equestrian-ready estate. Recently renovated to perfection, this five-bedroom, five-bathroom residence seamlessly blends sophisticated design with modern efficiency, featuring brand-new utilities and owned solar panels. The heart of the home is a dream kitchen, boasting radiant heated floors, a high-end Subzero panel refrigerator, custom cabinetry with integrated inserts, and a spacious walk-in pantry. Entertain with ease in the formal dining room or retreat to the quiet study, complete with floor-to-ceiling custom built-in bookshelves. The primary suite serves as a private sanctuary, featuring an ensuite, with a cozy fireplace, a custom vanity, a bidet, a standalone shower, and a deep soaker tub. Step onto heated floors in both the primary bath and kitchen for year-round comfort. Practicality meets convenience throughout the home, which includes three separate laundry rooms, a fully finished basement, and an oversized three-car garage. Step outside to your own private oasis, where the expansive grounds offer ample space for equestrian pursuits, complemented by a pristine inground pool perfect for summer relaxation. This property offers an unparalleled combination of style, comfort, and sustainable living. Schedule your private tour today.

14 Loft Road, Smithtown
$575,000
3 Beds ⋅ 2 Baths ⋅ 1027092 MLS
Investor & Handyman Special! Property being sold AS-IS. Opportunity awaits at 39 William Street, Smithtown. This 3-bedroom, 1.5-bath Colonial offers 1,726 square feet of living space on a flat, level property and is ready for its next chapter. Featuring a well-designed layout, this home offers endless potential for renovation and customization. The walk-out basement provides the possibility for a mother-daughter setup with the proper permits, adding flexibility for future use. Outside, enjoy an in-ground pool with a 2-year-old liner, creating the perfect foundation for your own backyard retreat. Whether you’re an investor, contractor, or buyer looking to build sweat equity, this is a fantastic opportunity to create value in a desirable Smithtown location. Bring your vision and make this home your own!

39 William Street, Smithtown
$985,000
4 Beds ⋅ 3 Baths ⋅ 1026048 MLS
Come Live A Lifestyle in this very Desirable 24/7 Gated Golf Community with Amenities. This 4 Bdrm, 3 Bth Colonial style Home offers endless possibilities to make this the home of your Dreams! The Grand entrance foyer boasts a soaring 20 ft Ceiling/ chandelier on a power switch, as well as beautiful architectural moldings. The main level includes a Formal Living Room, Formal Dining Rm, Great Rm/Wood Burning Fplc, EIK/Beautiful Wood Cabinets, Full Bthrm, Office or 4th Bdrm & Mud Room. Double Sliding Doors from the Kitchen & Great Rm lead out to a pavered patio which overlooks tranquil views of the 2nd Fairway. The 2nd level features a Primary Bdrm /3 large Closets & Master Bthrm/Jacuzzi Tub, Double Sinks, Toilet & Linen Closet. There are 2 additional Over Sized Bdrms/ a Full Bathroom. The Laundry Rm is conveniently located on the 2nd Floor/Washer, Dryer & Slop Sink. This Beautiful Home Offers CAC, CVAC, Alarm System, Gas Heat & Gas Cooking, & Sprinkler system. The Lower Level offers a Full Unfinished Bsmt/9'Ceilings for Extensive Storage or to finish to your own Specifications. Residence of Stonebridge can enjoy a Heated Salt Water Pool, Tennis & Pickleball, Card & Exercise Room. HOA dues of $565.00 include Landscape maintenance, Snow Removal, Trash pickup & Water. Conveniently located next to Blydenburg Park/easy access to No.State Pkwy & LIE, McArthur Airport, Great Restaurants & Town Beaches.

103 Redan Drive, Smithtown

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