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5 Judges Lane, Smithtown
$780,000
3 Beds ⋅ 2 Baths ⋅ 996702 MLS
Don't miss out on this unique, fully updated 3-bedroom 2-full bath ranch property in the heart of Smithtown! Located on a private country lane, the landscaping and overall curb appeal of this property makes heads turn! Positioned only a few hundred yards from Main Street, you'll enjoy accessability to shops, eateries, the library, and Smithtown Historical Society grounds without even starting your car. Whether you are enjoying morning coffee made at your custom coffee station, or entertaining friends while preparing a meal in your outdoor kitchen, this home is made for relaxing and sharing good times with the people most important to you. For added convenience, you'll find the Smithtown train station to NYC only 1 mile away, Stony Brook University 5 miles, and pristine beaches only a 10 minute drive.

5 Judges Lane, Smithtown

61 Ledgewood 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

9 Dillmont Drive, 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

49 Sandy Hollow Drive, Smithtown
$749,999
3 Beds ⋅ 2 Baths ⋅ 992899 MLS
Welcome to this fully renovated raised ranch located in the highly desirable Commack School District, offering the perfect combination of modern design and everyday functionality. This 3 bedroom, 2 full bathroom home features a bright open concept layout with hardwood floors throughout and a stunning kitchen complete with quartz countertops, stainless steel appliance, a center island, gas cooking, and sliding glass doors leading to a deck overlooking the backyard, creating an ideal setup for both daily living and entertaining. The upper level features all three bedrooms including a spacious primary along with a full bathroom, while the lower level offers a versatile living den, a second full bathroom, and direct access to the attached 1 car garage, providing the flexibility today’s buyers are looking for whether for extended living space, guests, or a home office. Additional highlights include central air conditioning with forced hot air and gas heating. Conveniently located near shopping, parks, and major roadways, this is a true move-in ready opportunity in a prime location.

49 Sandy Hollow Drive, Smithtown

271 Terry Road, 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

28 Dartmouth Drive, Smithtown
$749,990
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

22 Sheppard Lane Unit #B, Smithtown
$749,900
4 Beds ⋅ 3 Baths ⋅ 1042067 MLS
Located in the sought-after area of Smithtown with only one prior owner- this spacious 4-bedroom, 2.5-bath Colonial offers plenty of room to live, work, and entertain. Featuring beautiful hardwood flooring throughout, this home boasts a 2-car attached garage with two new electric doors. En-suite master offers a walk-in closet and tremendous space. The den is warm and inviting with a wood-burning fireplace, while newer windows throughout provide added comfort and efficiency. The first-floor laundry room includes a new washer and dryer for added convenience. Two high-efficiency ductless AC systems on the first floor provide cooling in the warmer months and supplemental heat when needed. The basement offers a large, versatile space with excellent storage potential. Near all shops and mins away from the LIRR-A wonderful opportunity to make this spacious Smithtown Colonial your next home! Taxes do not reflect Basic Star Discount of $877.00

22 Sheppard Lane Unit #B, Smithtown

2 Erita Lane, Smithtown
$749,000
3 Beds ⋅ 3 Baths ⋅ 1037385 MLS
Welcome to this spacious ranch-style home in the heart of Smithtown, set on a beautiful .36-acre property. This inviting home offers 3 generously sized bedrooms and 3 full bathrooms, providing plenty of space and comfort for everyday living and entertaining. The main living areas include a welcoming living room, formal dining room, and comfortable den, offering versatile spaces for nearly every need. Step outside from the home and enjoy the deck overlooking the property, perfect for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The large basement provides exceptional additional space, featuring three-car parking, a full bathroom, laundry, and tons of storage, making it ideal for vehicles, equipment, hobbies, and all your storage needs. This Smithtown home offers wonderful potential for comfortable living in a convenient Long Island location.

2 Erita Lane, Smithtown

191 Old Willets Path, Smithtown
$749,000
4 Beds ⋅ 2 Baths ⋅ 998336 MLS
Smithtown opportunity awaits! This Hi-Ranch horse property home is situated on a beautiful 1-acre lot, set back off the road for added privacy and a peaceful setting. This versatile property features a possible mother/daughter setup with proper permits, providing flexibility for a variety of living arrangements. Additional features include central air conditioning, a wood-burning stove, full attic storage, 200-amp electric service, generator hookup with sub-panel, and an oil burner that has been routinely maintained. Enjoy outdoor living on the Trex deck with awning overlooking the expansive property, complete with a 4-zone in-ground sprinkler system. A spacious two-car garage provides ample room for vehicles, storage, or hobby space, this home presents and excellent opportunity for buyers looking to add their own personal touches and create their dream home in a private , desirable setting . Offering generous living space, a functional layout, and solid bones, this home presents an excellent opportunity for buyers looking to add their own personal touches and create their dream home in a private, desirable setting.

191 Old Willets Path, Smithtown

19 Ridgeley Road, Smithtown
$738,000
3 Beds ⋅ 2 Baths ⋅ 1043090 MLS
WARMTH, COMFORT AND CHARM ON .56 ACRE OF MAGNIFICENT PROPERTY WITH LOW LOW TAXES Welcome to this expanded ranch in the sought after Smithtown School District. This home boasts a large, sunlit family room, hardwood floors, 3/4 bedrooms, a separate office/library room, newly renovated kitchen and baths and a large full finish basement with den, nanny's room, full bath, and storage galore, 2yr Burner Washer and Dryer. The oversized shy 2/3 acre property is a true backyard oasis with 1,000 sq ft of paver patios, a fire-pit, gazebo, pool, shed and PVC fencing. There’s also a separate area with outside entrance, perfect for extended family that come to visit. Taxes with Basic Star $10,515 Gas right on corner on Gilbert. Pool as gift

19 Ridgeley Road, Smithtown

653 Meadow Road, Smithtown
$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

20 Brook Lane, Smithtown
$719,000
3 Beds ⋅ 2 Baths ⋅ 1050347 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

48 Oak Avenue, Smithtown
$700,000
3 Beds ⋅ 3 Baths ⋅ 1042150 MLS
This 3 Bedroom, 3 Full Bathroom, Open Floor Plan, Raised Ranch is awash in natural light. With gas heat and central air-conditioning (new unit, 3 months old), this home delivers year-round comfort. The main level showcases an Eat-in-Kitchen, Dining Room and Living Room with sliding-door exit to the bi- level backyard deck, as well as a Master Bedroom with Full Bath, two additional bedrooms and a second full bath. The lower level hosts a sizable family room, fireplace and bar, including a third full bathroom – perfectly suited for entertaining family & friends, relaxing with a movie or a good book, containing ample space for a home office or study. A straight walk out to the two-car garage passes the separate laundry room. The paver driveway leads to the backyard. An underground sprinkler system feeds the grass and shrubs. Located on a tranquil street, just two blocks from Smithtown Elementary School, it’s a short distance to Main Street, boasting easy access to the LIRR, shopping, restaurants, the Smithtown Library. Or to Brady Park, offering a playground, baseball fields, basketball courts, tennis courts and much more. Beloved by the seller for nearly three decades, the next chapter can be yours.

48 Oak Avenue, Smithtown

26 Scarborough Drive, Smithtown
$690,000
2 Beds ⋅ 3 Baths ⋅ 1035010 MLS
Welcome to Windcrest at Smithtown, a desirable pet-friendly, gated community offering maintenance-free, resort-style living! This beautifully renovated Brittany model townhome features 2 spacious bedrooms, 2.5 baths, and has been thoughtfully updated throughout. Freshly painted and move-in ready, the home showcases a renovated kitchen with white cabinetry, quartz countertops, and stainless-steel appliances. The renovated bathrooms offer a fresh, modern design, while the expansive primary suite features custom walk-in closet and a private bath. Custom closet systems have also been added to the second bedroom & linen closet for exceptional storage and organization. Enjoy resort-style amenities including a clubhouse with a card room, TV and sitting room with fireplace, outdoor swimming pool, tennis courts, pickleball, fitness center, and a gazebo overlooking a picturesque pond with a fountain. Conveniently located near shopping, dining, MacArthur Airport, and the LIRR, this exceptional home offers low-maintenance living with all the comforts of home.

26 Scarborough Drive, Smithtown

8 Gedney Avenue, Smithtown
$689,000
3 Beds ⋅ 1 Baths ⋅ 1046648 MLS
Move right into this beautifully updated Ranch where pride of ownership is evident throughout! Extensively renovated with comfort, efficiency and low-maintenance living in mind, this home features a beautifully updated kitchen with quartz countertops, gas cooking and modern appliances, along with updated electrical, plumbing and heating systems. Central air, motorized blinds and a reverse-osmosis drinking water system add to the home's comfort and convenience. Major exterior improvements include newer roof, siding and gutters, bluestone front steps and walkway, PVC fencing, inground sprinklers and an updated driveway. The insulated and finished garage offers additional versatility and is equipped with a subpanel suitable for electric vehicle charging. Additional electric service extends to the shed, while natural gas is also available for the dryer and outdoor BBQ. Thoughtful improvements inside and out make this a truly turn-key home—just unpack and enjoy all this house has to offer!

8 Gedney Avenue, Smithtown

22 Lindron Avenue, Smithtown
$669,000
4 Beds ⋅ 2 Baths ⋅ 1039961 MLS
Welcome to 22 Lindron Avenue, a versatile Wide-Line High-Ranch home nestled on a peaceful, tree-lined street in the heart of Smithtown. This property offers exceptional living space and multi-generational flexibility, featuring a sunlit main living area with a wood-burning fireplace, elegant crown molding, and neutral finishes. The main kitchen comes equipped with warm oak cabinetry, granite countertops, tile backsplash, and stainless steel appliances, seamlessly connecting to a dedicated dining room highlighted by detailed wainscoting. The floor plan includes a full bath on both levels, as well as a functional lower-level kitchenette setup and flexible office nook ideal for extended guest quarters. Outside, enjoy an oversized back-yard, an attached two-car garage, and a multi-level rear wooden deck overlooking the private yard. Complete with updated electrical service panel and dedicated gas utilities, this home offers outstanding potential just minutes from Smithtown schools, local shopping, dining, parks, and LIRR commuter access.

22 Lindron Avenue, Smithtown

59 S Pond Lane, Smithtown
$650,000
2 Beds ⋅ 2 Baths ⋅ 1042904 MLS
Welcome to Hidden Ponds, a beautiful gated community in the heart of Smithtown. This spacious end-unit ranch townhouse offers the perfect combination of comfort, convenience, and easy one-level living. A welcoming foyer leads into the eat-in kitchen with an electric cooktop and the convenience of an in-unit washer and dryer. The open-concept living and dining area showcases a cozy fireplace, soaring ceilings, and sliding glass doors that open to a private oversized patio overlooking tranquil pond views. Tile and carpeting flow throughout the living spaces and bedrooms.The home offers two generously sized bedrooms and two full bathrooms. The primary bedroom features a walk-in closet and private en-suite bathroom, creating a comfortable and functional retreat.

59 S Pond Lane, Smithtown

31 Ridge Road, Smithtown
$649,000
4 Beds ⋅ 3 Baths ⋅ 1047272 MLS
Opportunity Awaits in Smithtown! Situated on an expansive 0.75-acre property, this 4-bedroom, 3-bathroom home offers approximately 2,632 square feet of living space, generous room sizes, and a fireplace. The property requires extensive renovation and clean-out, presenting an ideal opportunity for an investor, contractor, or buyer ready to restore and transform the home. With its substantial footprint, impressive lot size, and desirable Smithtown location, this property offers tremendous potential for the right buyer. Bring your contractor and your vision! Property is being sold strictly AS-IS and will not be delivered broom-clean. The buyer will be responsible for removing all personal property, contents, and debris remaining at the property after closing. Buyers should perform their own due diligence regarding the property’s condition, permitted uses, and financing eligibility.

31 Ridge Road, Smithtown

22 South Avenue, Smithtown
$649,000
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

33 Laurel Drive, Smithtown
$599,999
4 Beds ⋅ 1 Baths ⋅ 1024885 MLS
Welcome to 33 Laurel Drive, a charming cape nestled in the quiet, tree-lined neighborhood of Smithtown Pines. This home presents an exceptional opportunity for those seeking to make their mark on a timeless property with endless potential. Before stepping through the front door, you'll be greeted by a spacious 1/2 acre level lot that offers a peaceful retreat from the hustle and bustle. The expansive driveway can accommodate 8 or more cars, providing ample space for gatherings or simply for those who need the extra parking. Inside, the home offers four bedrooms, one bathroom and an office. The original hardwood flooring adds a touch of elegance and warmth, while the wood-burning fireplace creates a cozy atmosphere for those cooler nights. The property also includes two detached garages, perfect for storage or for those with a passion for projects. The full, unfinished basement features an outside entrance, offering potential for additional space or storage. The highly desirable Pines Section is a sought after gem in Smithtown, a vibrant community that boasts a variety of restaurants, shops, parks, and beaches. Outdoor enthusiasts will appreciate the proximity to golf courses, beaches, and hiking trails. Nearby Laurel Park, a local favorite boasts recently updated recreational activities including; playground, tennis, basketball, handball courts and benches to sit and relax. Major Parkways are easily accessible, making commutes a breeze. Now, imagine the possibilities. This home provides an incredible opportunity for first-time buyers or those looking to expand and customize their dream home. With low taxes and natural gas available in the street, the practicalities of this home are as appealing as its charm. Within this community, you're not just buying a home, but a lifestyle. Enjoy the tranquility of your quiet block, the convenience of nearby amenities, and the potential to create a home that truly reflects your vision. Welcome to 33 Laurel Drive, where charm, opportunity, and community come together.

33 Laurel Drive, Smithtown

42 Meadowbrook Lane, Smithtown
$457,310
2 Beds ⋅ 1 Baths ⋅ 1024377 MLS
Affordable Homeownership Opportunity in Desirable Country Pointe Woods! Beautiful 2-bedroom condo with a versatile office/flex room, dedicated laundry room, abundant closet space, one-car garage, and private driveway. Located in a gated, resort-style community featuring a clubhouse, fitness center, heated pool, bocce court, card room, and lounge. Conveniently located near shopping, restaurants, parks, the LIE, Northern State Parkway, and the LIRR. This home is being sold through the Long Island Housing Partnership (LIHP) Affordable Housing Program. Purchasers must qualify as first-time homebuyers and meet LIHP income, asset, mortgage, and owner-occupancy requirements. Maximum annual household income limits are: 1 person - $149,500; 2 people - $170,850; 3 people - $192,250; 4 people - $213,600 LIHP approval is required prior to closing, and future resale restrictions apply.

42 Meadowbrook Lane, Smithtown

10 Smithtown Boulevard Unit #3B, Smithtown
$239,999
1 Beds ⋅ 1 Baths ⋅ 1053623 MLS
Welcome to 10 Smithtown Blvd Unit 3B, offering top-floor privacy in a highly desirable Smithtown location. Stop paying rent and invest in a spacious 1 bedroom, 1 bathroom co-op. Offering generous room dimensions and fantastic natural light, this home gives buyers the change to personalize finishes, paint, and style to match their individual taste. Highlights include an oversized living room, an eat in kitchen, and rare storage options - featuring a hallway walk in closet, double bedroom closets and pull down attic access. Enjoy low maintenance living with taxes, heat, water, snow removal and grounds care included in the maintenance fee. Located within the Smithtown School District close to all. Bring your personal style and create a home you'll love!

10 Smithtown Boulevard Unit #3B, 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.