Smithtown NY Real Estate, Homes, Condos for Sale

Welcome to 40 Friendly Rd. A home that redefines style, comfort, and convenience. This turn-key, fully renovated property combined luxury and functionality flawlessly. The exterior showcases a perfect blend of brick, Azek facade and oversized Andersen windows exuding a modern yet timeless appeal. As you step inside, you are greeted by a two-story entry foyer with a grand chandelier and monorail/glass floating staircase. The open floor layouts on both floors provide a seamless flow from room to room, making it perfect for both entertaining and everyday living. The kitchen is a chef's dream, featuring custom 3/4" solid white oak and black glass cabinets, custom quartz hood, Viking appliances with a 6-burner stove, and a double island set up. The hidden walk-in butler's pantry offers plenty of storage and adds a touch of luxury. Kitchen flows into a vaulted ceiling family room with a large concrete fireplace which leads to an oversized Trex deck perfect for outdoor entertaining. The property boasts five bedrooms and three and a half well-appointed bathrooms. Custom millwork throughout with 9" wide plank wood flooring, 6" base moldings and a large wet bar on the first level. The home is equipped with a tankless Navien system and a York HVAC system, ensuring optimal comfort all year round. The meticulously landscaped outdoor area with 9 sprinkler zones and new sod provides a tranquil retreat, perfect for enjoying the outdoors. This home is located close to 347 allowing easy access to all local amenities. Whether you are looking for recreation, shopping centers or dining options, you'll find it all within easy reach.

40 Friendly Road, Smithtown

$855,000

4 Beds ⋅ 3 Baths ⋅ 1047477 MLS

Welcome to this beautifully appointed 4-bedroom, 2.5-bath Colonial, ideally situated in the highly desirable Royal Woods/Hillside neighborhood and within the acclaimed Smithtown School District. Freshly painted throughout, this inviting home offers a bright, move-in-ready feel from the moment you arrive. Sun-filled interiors showcase beautiful hardwood floors, cathedral ceiling, a charming bay window, and skylights that create an airy and welcoming atmosphere throughout the home. The spacious living area is anchored by a stunning floor-to-ceiling, full-wall granite wood-burning fireplace, creating an impressive focal point that brings warmth, character, and timeless elegance to the space. The well-appointed kitchen features stainless steel appliances just three years old, combining modern convenience with functionality. The spacious primary suite offers a private retreat, complete with a walk-in cedar closet and a full bath. Enjoy year-round comfort with a high-efficiency heat pump installed just one year ago, providing reliable heating and cooling. An oil-fired hot water heating system remains available as an additional heating option. Step outside and discover your own backyard sanctuary. The inviting inground pool features a one-year-old liner, steps, and pump, while the expansive stone-paver patio provides the perfect backdrop for outdoor entertainment, summer gatherings, or simply relaxing in your own peaceful outdoor escape. Ideally located near Smithtown beaches and Smithtown Landing Golf & Country Club, this exceptional home offers a wonderful combination of comfort, style, convenience, and lifestyle. With its spacious interiors, beautiful outdoor setting, and prime location, this is an opportunity not to be missed. Come make this special home your own!

22 Sheryl Crescent Crescent, Smithtown

$599,000

3 Beds ⋅ 3 Baths ⋅ 1048419 MLS

Welcome to 6 Valleywood Road in Smithtown. This 3-bedroom, 3-bath ranch offers the convenience of one-level living with nicely sized bedrooms and a functional layout. The basement provides additional space and flexibility, while the outdoor area offers plenty of opportunity to create a space that fits your needs. Located in a great Smithtown location, this home has lots of potential and is ready for you to make it your own.

6 Valleywood Road, Smithtown

$749,990

3 Beds ⋅ 2 Baths ⋅ 1047017 MLS

Welcome to 5 Kenny Street, a charming ranch-style home nestled in the heart of Smithtown. This delightful residence boasts three comfortable bedrooms and two full bathrooms, ensuring ample space for all. Upon arrival, you are greeted by the home's impressive curb appeal, set on a generous .34-acre flat parcel. Inside, discover the hidden treasure of hardwood floors beneath the carpeting, preserved for years and ready to shine. The home is equipped with central air conditioning, an updated heating system, and a modern hot water heater for your comfort. Recessed lighting is throughout the house. The spacious living room invites relaxation, while the separate den, enhanced with a cozy gas fireplace, provides an intimate retreat. The kitchen shines with updated stainless steel appliances, a vaulted ceiling with a skylight, and a convenient formal dining room stands ready for your meals and gatherings. The primary bedroom offers the luxury of an ensuite bathroom. The second full bathroom has a skylit vaulted ceiling. This beautiful home has a two-car garage with electric openers, a partially finished large basement with ample storage, and a laundry area adds to the home's practical appeal. Outside, a low-maintenance Trex deck overlooks the picturesque backyard, an ideal spot for outdoor enjoyment. There is an in ground sprinkler system in the front and back yard. The backyard is very private. This home's location is a gem, with easy access to major highways, public transportation, and shopping venues. Welcome to your future home, where convenience meets charm in Smithtown and within the Smithtown School District.

5 Kenny Street, Smithtown

$759,000

4 Beds ⋅ 2 Baths ⋅ 1046723 MLS

Welcome to this charming home located in Smithtown, within the award-winning Commack School District! This property offers a comfortable and functional layout featuring a formal living room with crown moldings and ceiling fan, formal dining room with built-in cabinetry and wine storage, perfect for entertaining and sliding glass door to exterior. The kitchen is equipped with stainless steel appliances, wood-finish cabinetry, tiled flooring and provides a great space for everyday living. The home offers 4 bedrooms and 2 full bathrooms, providing plenty of space for guests. A full basement, partially finished, adds valuable additional living and storage space and includes a washer and dryer. Additional features include oil heating, two thermostats for temperature control, a one-car garage, expansive rear Trex deck overlooking the backyard—ideal for outdoor relaxation and entertaining. Expansive back yard with mature trees providing natural privacy. The property is being sold AS IS. Don’t miss the opportunity to make this Smithtown home your own!

90 Cornell Drive, Smithtown

$699,999

3 Beds ⋅ 2 Baths ⋅ 1048457 MLS

Welcome to this beautifully maintained split-ranch home nestled in the highly sought-after East Hills Estates of Smithtown. This 3 bedroom, 2 bath, 1 car garage on 0.3 acres home (currently set up as two bedrooms, can be easily put back to three bedrooms) is filled with natural light and is move-in-ready! This residence offers the perfect blend of comfort, style, and functionality. The inviting main level features a bright and airy living room with soaring cathedral ceilings, a cozy gas fireplace, and an open flow into the eat-in kitchen featuring gas range, refrigerator, microwave, dishwasher (2023) and granite countertops, ideal for both everyday living and entertaining. Upstairs, you'll find a spacious primary bedroom with side-by-side double closets, a generously sized second bedroom, and full hall bath. The lower level offers a sun-filled den with abundant natural light, a full bathroom, laundry room and a convenient outside entrance, providing flexible living space perfect for guests, or a home office. 200-amp electric, Andersen windows, a cesspool with overflow (2021), vinyl fencing, separate hot water heater. and whole-house Generac generator. Situated on a tranquil .34-acre level lot, the private backyard is surrounded by mature specimen trees and lush landscaping and pond. With its mint condition, desirable location, and features, this exceptional home offers everything you are looking for.

1 Rutgers Street, 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 two custom walk-in closets and a private bath. Custom closet systems have also been added to the second bedroom, linen closet, and the finished basement for exceptional storage and organization. Additional upgrades include Andersen windows & glass door (approximately 4 years old), both furnaces 2024, hot water heater 2023 & Central Air Conditioning 2024 (both HVAC units), a natural gas fireplace with a marble surround, stylish designer light fixtures and a one-car garage with a 240-volt EV charging outlet. The finished basement provides additional living space with multiple custom closets, while the redesigned private patio creates the perfect outdoor retreat. A private driveway adds additional parking. 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

$875,000

3 Beds ⋅ 4 Baths ⋅ 1048487 MLS

Welcome to the Devonshire model at Willow Ridge, an impeccably maintained 3-bedroom, 3 and a half bath corner-unit condominium offering approximately 3,570 square feet of spacious living across three levels. Privately situated in one of the community’s most beautiful locations, this exceptional home overlooks a peaceful wooded area and offers a wonderful combination of privacy, comfort, and resort-style living. The main level features a spacious living room with soaring vaulted ceilings, creating an open and inviting atmosphere, along with a private primary ensuite complete with his-and-hers closets and a recently updated full bathroom. The main level also offers a convenient laundry room located directly off the garage. Step outside to the private balcony overlooking the wooded surroundings, complete with a retractable awning—an ideal spot for morning coffee, outdoor dining, or relaxing. The upper level features two additional generously sized bedrooms and a full bathroom, providing an ideal private space for family, guests, or a home office. The lower level offers additional flexible living space with two bonus rooms/bedrooms and a private patio, perfect for entertaining, recreation, or simply enjoying the tranquil setting. Additional features include gas heat, gas cooking, central air conditioning, and a home that has been lovingly cared for and meticulously maintained. Willow Ridge offers an array of amenities, including an in-ground pool, tennis courts, pickleball courts, and more. This beautifully situated Devonshire model offers generous living space, exceptional privacy, multiple outdoor areas, and the convenience of a premier community—all in desirable Smithtown on Long Island’s North Shore.

53 Willow Ridge Drive, Smithtown

$749,999

4 Beds ⋅ 2 Baths ⋅ 1044596 MLS

Super Clean Home that Features 4 Bedrooms, 1.5 Baths, Hardwood Floors, Anderson Windows thru-out, 2025 New Burner, Whole House water filtration system, Roof 2011, Granite EIK around 2018, Fireplace in Family Room, Pull Down-stairs for attic storage, 200 AMPS Electric, Expanded Driveway plus 2-Car Garage, Natural Gas in street already if you want to convert, Fenced Yard with Deck, Patio, Gardens, Shed for storage, and Low Maintenance yard to maintain. Taxes $12k per year, Need Smithtown Schools, then view this home located close to town.

6 North Avenue, Smithtown

$899,000

3 Beds ⋅ 2 Baths ⋅ 1047231 MLS

Welcome to 31 Dehan Street! A lovingly maintained three-bedroom, two-bathroom home with the flexibility for a fourth bedroom, inviting spaces designed for everyday comfort and located in one of the best school districts in town. Inside, hardwood floors flow through warm living areas featuring a wood-burning fireplace, formal dining room, granite countertops, Sub-Zero appliances, central air, and a partially finished basement. Step outside and discover the true showstopper: a beautifully level half-acre surrounded by mature, lush landscaping. Thoughtfully designed for relaxing and entertaining, the backyard offers generous lawn space, an awning, a wide sliding door, and utility connections for a motor home, hot tub, sauna, or Jacuzzi. A two-car attached garage and driveways from both Dehan and Leonard Streets provide exceptional convenience. With Andersen windows, updated mechanicals, and numerous thoughtful improvements, this is a home where comfort, beauty, and possibility come together.

31 Dehan Street, Smithtown

$799,000

4 Beds ⋅ 3 Baths ⋅ 1041929 MLS

Welcome to 16 Dogwood Drive, a spacious four-bedroom, 2.5-bath Colonial nestled in the incorporated Village of the Branch. Set on a beautiful .60-acre lot, this home offers a classic Colonial layout, generous living spaces, and wonderful potential to make it truly your own. The main level features a welcoming living room with a wood-burning fireplace, formal dining room, eat-in kitchen, den, and convenient half bath. The spacious layout provides comfortable areas for both everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms with ample closet space, including a primary bedroom with an en-suite full bath, along with an additional full hall bath. The primary bathroom has also been tastefully updated. Thoughtful improvements throughout the home include beautiful wood floors, vinyl siding, a newer cesspool, in-ground sprinkler system, and updated walls with new insulation in most living areas. The inner bedroom walls have also been soundproofed, providing added privacy and peace throughout the home. A full unfinished basement and one-car garage offer plenty of storage and the potential for future living or recreational space. Step outside to your own private backyard oasis, surrounded by mature Leyland cypress that create a peaceful and secluded setting. An in-ground pool and expansive paver-stone patio provide the perfect backdrop for summer relaxation, outdoor entertaining, and making lasting memories. Conveniently located between Smithtown and St. James, this home is close to shopping, restaurants, parks, recreation, and everyday amenities. With its classic Colonial charm, spacious rooms, established landscaping, and numerous updates, 16 Dogwood Drive is the perfect canvas to create the home you’ve always imagined personalized to reflect your own style, vision, and way of living!

16 Dogwood Drive, Smithtown

$799,000

4 Beds ⋅ 3 Baths ⋅ 1047638 MLS

Meticulously maintained 4 bedroom/3 bath expanded ranch (2300 square feet living space) in the heart of Smithtown. Same loving owner for the last 40 years. Large living room, formal dining room and eat-in kitchen with Andersen sliders to backyard. Primary suite extension with high ceilings, full bath and massive walk-in closet. Junior suite with full bath and walk-in closet. Long list of renovations and recent upgrades including 2025 new roof with 50 year warranty, 2025 gutters, upgraded 150 amp electric with generator plug-in, 2015 Peerless Cast-iron boiler with storage tank maintained regularly. Pella windows throughout. 2026 pumped and serviced both cesspools. Recently replaced oil tank with properly filed abandonment. Central air conditioning. Huge professionally landscaped property with in-ground sprinklers, outdoor lighting/speakers, TREX composite deck, patio and fire pit. Attached garage with additional attic storage. Truly turn key spotless move in condition home. TAXES HAVE BEEN GRIEVED FOR THE UPCOMING YEAR.

67 Broadway, 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

$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

$779,000

2 Beds ⋅ 3 Baths ⋅ 1044752 MLS

Recently renovated from bottom to top, this beautiful townhouse offers a prime location overlooking the pond in the desirable gated Hidden Ponds community of Smithtown. The bright and inviting open floor plan features high ceilings, plenty of natural light, a fireplace, formal dining room, and sliding doors opening to a private patio with peaceful pond views. Thoughtfully updated throughout with a brand-new kitchen and appliances, three beautifully renovated bathrooms, all-new windows and doors, new flooring and stairs, a new patio door, fresh paint, elegant crown molding, and new bedroom closets. The spacious primary suite offers large windows and a walk-in closet. A private laundry room and attached garage add everyday convenience. Enjoy resort-style amenities including a heated saltwater pool, fitness center, tennis, pickleball, basketball, bocce, shuffleboard, dog run, ping pong, and a renovated clubhouse with a fireplace and kitchen, also available for private gatherings. HOA $391/month. Beautifully updated, move-in ready, and a wonderful opportunity to enjoy the Hidden Ponds lifestyle.

230 Pond View Lane, Smithtown

$850,000

4 Beds ⋅ 3 Baths ⋅ 1044068 MLS

Beautiful Updated Colonial in a Quiet, Friendly Neighborhood This spacious Colonial home features a fully updated kitchen with a center island, seamlessly opening into a generous formal dining room and an airy living room. A warm and inviting family room with a brick fireplace adds charm and comfort, along with a convenient half bath on the main level. A slider door leads out to a large deck overlooking a fully fenced backyard, complete with an inground pool and slide — perfect for summer fun and entertaining. Upstairs, you’ll find the home’s private living spaces, while the property sits on a quiet, friendly, and picturesque street, close to all shopping, major highways, and transit options for easy commuting.

14 Format Lane, Smithtown

$799,999

3 Beds ⋅ 3 Baths ⋅ 1042682 MLS

Welcome to this updated ranch in the heart of Smithtown, offering a wonderful blend of comfort, versatility, and indoor-outdoor living. Upon entry, you’ll immediately notice the abundance of natural light streaming through a wall of windows overlooking the private backyard. The outdoor space is designed for relaxation and entertaining, featuring a saltwater in-ground pool with diving rock, water sprays, and a waterfall, a paver patio, Trex deck, and awning for additional shade and covered enjoyment. Inside, the living room flows into an L-shaped dining room, while the kitchen features warm dark maple cabinetry, granite countertops, and stainless steel appliances. A conveniently located laundry room off the kitchen provides direct access to the two-car garage. The primary en-suite offers a walk-in closet, additional closet, and private full bath with shower stall. Two additional bedrooms share a spa-inspired hall bathroom featuring a vaulted ceiling, whirlpool tub, separate shower stall, and oversized vanity. The finished lower level provides additional living space with a recreation room featuring a wood-burning fireplace, office/possible 4th bedroom, and half bath. The unfinished portion offers utilities and ample storage. Additional features include hardwood and Laminate flooring, central air conditioning, in-ground sprinklers, 200-amp electric, and a two-car garage. Conveniently located just minutes from the train station, St. Catherine of Siena Hospital, shopping, dining, and all that Smithtown has to offer.

59 Derby Place, 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

$759,000

4 Beds ⋅ 4 Baths ⋅ 1042725 MLS

Welcome to 23 Dale Lane! This well-maintained 4BR, 3.5BA multi-level home on .25 acre offers exceptional versatility for comfortable single-family or multigenerational living. The inviting entrance foyer leads upstairs to the living room, dining room and eat-in kitchen overlooking the lower-level den, featuring a wood-burning fireplace and sliding glass doors to a Trex deck and inviting in-ground pool. A powder room, laundry and utility rooms complete this level. Upstairs features a spacious primary ensuite with walk-in closet, two additional bedrooms and full bath. An open staircase off the entrance foyer leads to the lower level that offers a fourth ensuite bedroom, providing privacy and flexibility for guests or multigenerational living a versatile office, storage and recreation area with cabinetry, sink and private outside entrance. PVC fencing adds privacy. First and Second Level 1957 Sq. Feet and Lower Level with outside entrance 774 Sq. Feet Come see for yourself and fall in love!

23 Dale Lane, Smithtown

$799,000

4 Beds ⋅ 3 Baths ⋅ 1036711 MLS

Welcome to 10 Foothill Lane in Smithtown, located in the desirable Crown Estates community and served by the highly regarded Commack School District. This popular-style Colonial sits on a beautiful .33-acre corner lot. An inviting foyer opens to a spacious living room with a front bay window that fills the space with natural light. The formal dining room flows into the well-appointed wood kitchen, featuring quartz countertops, stainless steel appliances and a breakfast island—an ideal setting for entertaining year-round. The main level also offers beautiful oak hardwood floors, an updated half bath, a spacious laundry room and a mudroom with convenient access to the two-car garage. Upstairs, the primary en suite includes a walk-in closet and private full bath. Three additional generously sized bedrooms and a second full bath complete the level. Hardwood floors run throughout, including beneath carpeting in several rooms. A full attic with pull-down stairs provides abundant additional storage. The partial basement offers even more storage, along with closets, a utility room and wood-look tile flooring, providing endless possibilities. Sliding doors lead to a beautiful park-like backyard with ample space for entertaining gatherings of any size and room to add an in-ground pool. Other highlights include a young roof (2022), 4-zone inground sprinklers and conversion to gas heat and cooking (1999).Discover all that 10 Foothill Lane has to offer and imagine the personal touches that will make this wonderful home your own!

10 Foothill Lane, 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

$629,999

3 Beds ⋅ 2 Baths ⋅ 1043462 MLS

Welcome to this well-maintained 3-bedroom, 1.5-bathroom split ranch in Smithtown. The home features hardwood floors throughout and offers a comfortable and versatile layout. The kitchen was updated approximately 15 years ago, and the full bathroom was renovated within the past year. Additional features include a den, garage, fenced-in yard, 200-amp electric service, approximately 15-year-old roof, and an in-ground 5-zone sprinkler system. The fenced yard provides private outdoor space for a variety of uses. Conveniently located in Smithtown, this well-maintained home offers an opportunity to add your own personal touches and make it your own.

6 Sybil Place, 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!

22 Sheppard Lane Unit #B, Smithtown

$1,399,000

4 Beds ⋅ 4 Baths ⋅ 1041795 MLS

Architecturally distinctive private equestrian estate featuring handcrafted vaulted wood ceilings throughout and refined natural stone detailing. Guest suite with private bath, Situated within an idyllic, private wooded landscape, surrounded by timeless natural beauty. Beautifully positioned windows frame breathtaking scenic views, with a private barn enjoying panoramic views. Three generous driveways and an impressive circular driveway enhance the estate-like setting. A truly exceptional property offering privacy, natural beauty, and timeless architectural character.

Smithtown

$749,000

4 Beds ⋅ 2 Baths ⋅ 1041363 MLS

Set on a quiet Smithtown street with a generous half-acre of property, this spacious 4 bedroom, 2-full bath High Ranch offers plenty of room inside and out, along with low taxes and Smithtown schools. The home features an updated kitchen and bathrooms, hardwood floors throughout the second floor, central air conditioning, and stainless steel appliances, including a Fisher & Paykel refrigerator. All appliances are less than three years old. The home has also been converted to natural gas and features a tankless on demand hot water heater/boiler also 3 years old. The flexible lower level offers additional living space, including a den with its own entrance to the backyard ideal for additional living space or a home office providing plenty of options to suit your needs. Outside, the fully fenced, expansive backyard offers tremendous potential, with plenty of room for a pool, patio, outdoor kitchen and entertaining area while mature plantings include a peach tree, fig tree and grapevines adding to the charm of this property. Garage with abundant storage and ample driveway parking add even more convenience. With its half-acre property, flexible living space, important updates, low taxes and desirable Smithtown location, this home offers a fantastic opportunity!

16 Edgar Drive, Smithtown

$829,000

3 Beds ⋅ 4 Baths ⋅ 1041063 MLS

Welcome to 23 Willow Ridge Drive, A RARE CORNER, END UNIT in the desirable Willow Ridge community! Beautifully maintained and thoughtfully appointed, this exceptional home offers 3 bedrooms and 3.5 baths with an impressive blend of style, comfort, and convenience. The beautiful white kitchen features Thermador appliances, granite countertops, and heated floors, creating an inviting space for both everyday living and entertaining. Two gas fireplaces add warmth and character throughout the home. Upstairs, the newly updated primary bathroom offers a luxurious retreat with a free-standing Jacuzzi tub and heated floors. A conveniently located second-floor washer and dryer makes laundry a breeze, while two cedar closets provide thoughtful storage and a central vacuum system adds ease to everyday home maintenance. Enjoy seamless indoor-outdoor living from the first-floor balcony overlooking the spacious backyard—an ideal setting for relaxing or entertaining. A natural gas barbecue connection and convenient walk-out access make outdoor gatherings effortless. Exquisite custom blinds and beautiful lighting fixtures, including a stunning chandelier, add an elegant finishing touch throughout the home. The freshly painted interior create a clean, move in ready feel. Residents of Willow Ridge enjoy exceptional community amenities, including a heated pool, recreation room, and tennis and pickleball courts. With its desirable corner end-unit location, beautiful updates, luxurious details, and outstanding amenities, 23 Willow Ridge Drive is truly a special place to call home. Don’t miss the opportunity to make this exceptional property yours!

23 Willow Ridge Drive, Smithtown

$1,099,988

5 Beds ⋅ 4 Baths ⋅ 1039816 MLS

Welcome to this spacious 3,800-square-foot Colonial home, featuring a versatile split-level layout with 5–6 bedrooms and 4 full bathrooms, offering plenty of room for an extended or growing family. The home features a possible mother-daughter setup with proper permits, providing flexibility for multigenerational living. Step through the large walk-in entry into a bright and welcoming interior filled with an abundance of natural light and impressive high ceilings. The first floor features 2 generous bedrooms, 2 large living rooms, 2 full bathrooms, a kitchenette, and a laundry room, along with an attached 3-car garage. The second floor offers a formal living room with a wood-burning fireplace and a possible private office, providing an elegant and flexible space for entertaining or working from home. The third floor showcases an additional dining room, a large eat-in kitchen, and 4 bedrooms, including a primary bedroom with a private full bathroom and its own deck. The home's flexible layout provides plenty of space to accommodate a variety of living arrangements. Additional highlights include hardwood floors, high ceilings, central air, an attic for extra storage, a covered porch, a back deck with a Jacuzzi, and a private driveway. Situated on a generous 19,602-square-foot lot, the property also features an updated roof (2019) and low taxes. This unique home offers exceptional space, versatility, and comfort, with plenty of room to make it your own.

23 Colonial Drive, 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

$699,999

3 Beds ⋅ 2 Baths ⋅ 1040470 MLS

Location! Location! Location! Welcome to this beautifully refreshed split-level home, where style, comfort, and versatility comes together in one exceptional Smithtown offering. From the moment you arrive, the new driveway and freshly painted interiors with the cathedral ceiling sets the tone for a home that feels polished, inviting, and ready to enjoy. The home opens to a bright and thoughtfully designed layout offering 3 bedrooms and 2 full baths, with comfortable living spaces that transition effortlessly from everyday moments to entertaining family and friends. What truly sets this home apart is its versatile lower level with a separate entrance, creating exciting possibilities for extended living, a private home office, guest space, recreation area, or whatever best complements your lifestyle. Recent improvements add even more value and peace of mind, including a new gas burner and hot water heater, new dishwasher, and new washing machine. Go outside and enter the generous corner plot that provides the perfect backdrop for alfresco dining, summer gatherings, gardening, or simply unwinding at the end of the day. Thoughtfully updated, and filled with possibilities, this home delivers the space and flexibility today’s buyers are looking for, wrapped in a warm and beautifully presented home. With the top-rated Smithtown schools, and a neighborhood close to shopping, dining, highways and close to the train station, this is a special opportunity in Smithtown that deserves to be experienced in person.

23 Riviera Drive, 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

$1,950,000

4 Beds ⋅ 4 Baths ⋅ 1039294 MLS

Welcome to 38 Riverview Terrace, an exceptional custom-built Colonial offering five bedrooms, three full bathrooms and one half bath, with an extensive array of high end finishes, entertainment spaces and resort-style outdoor amenities. A grand foyer welcomes you with wainscoting, chandelier and stunning maple hardwood flooring that continues throughout the first floor. The main level features an elegant formal dining room and a spacious den anchored by a wood-burning fireplace. The expansive eat-in chef’s kitchen is designed for both cooking and entertaining, featuring a large 7'10" center island, quartz countertops throughout, skylights, a breakfast area and modern farmhouse sink. High-end Sub-Zero and Wolf appliances include an eight-burner Wolf range with double ovens, a massive custom hood with pot filler, an additional wall oven, warming drawer, built-in microwave, ice maker and wine cooler. Radiant heated flooring completes the kitchen. A powder room with radiant heated flooring is conveniently located on the main level for guests, along with a dedicated first-floor laundry room. Upstairs, the spacious primary suite features an impressive custom walk-in closet and spa-inspired bath with a soaking tub, radiant heated flooring and heated towel rack. Four additional bedrooms and beautifully appointed bathrooms provide plenty of space throughout the home. Skylights throughout bring an abundance of natural light into the residence. The finished lower level is designed for recreation and entertainment, offering an expansive recreation area with a wet bar and dedicated media room/home theater with its own home entertainment system. The home is wired for seven televisions, while a Sonos sound system with outdoor speakers extends the entertainment outdoors. The backyard offers private country club style amenities, beginning with a spectacular heated in-ground pool with cascading waterfall surrounded by expansive armortec paving stones. Professionally landscaped grounds and dramatic landscape lighting create a beautiful setting for outdoor entertaining. A fully equipped outdoor kitchen with built-in grill, pergola and pavilion provide additional gathering spaces, while a pickleball court and basketball court offer recreation right at home. An attached two car garage completes this extensively appointed Smithtown residence, offering exceptional indoor and outdoor living with amenities designed for entertaining, recreation and everyday enjoyment.

38 Riverview Terrace, Smithtown

$779,999

4 Beds ⋅ 2 Baths ⋅ 1036685 MLS

Welcome to this newly renovated 4 bedroom, 2 bathroom Expanded Cape home located in a desirable area of Smithtown, NY. The main level boasts a beautiful inviting living room with a bay window, designer molding, recessed lighting, new flooring, and sliders to backyard, an open concept kitchen with stainless steel appliances, dining area with sliders for quick access to backyard, 2 first floor bedrooms, an updated full bathroom and a laundry area. The second floor offers a very spacious, sun drenched primary bedroom with ensuite bathroom, high ceilings with skylights, plenty of closets, and an additional bedroom. The backyard has transformed into an entertainer’s paradise, featuring an in-ground pool with waterfall, an upgraded pool filtration system, in-ground sprinkles, a charming wooden deck, a large garage for storage, two sheds and a spacious workshop space in the back that creates a stunning outdoor space perfect for enjoying the warm summer days. Additional improvements include, a remodeled kitchen, two updated bathrooms, new flooring, recessed lighting and new doors, updated out siding, freshly painted interior walls, tree removals, yard leveling, new landscaping, and new pool filtration system. This property is in a PRIME location of Smithtown. Close to Smithtown LIRR train station, Main Street dining & shopping, Smithtown schools, Blydenburge County park, Caleb Smith State Park, Smithtown library, and many other amenities.

36 Fifty Acre Road S, 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

$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

$379,999

2 Beds ⋅ 1 Baths ⋅ 1033107 MLS

Absolutely immaculate; fully renovated, move in ready 1st floor 2 bedroom unit. Being on the first floor allows for a private entrance, located just feet away from assigned parking spot as well as the well maintained laundry room. This unit was just renovated earlier this year so everything is brand new! Windows and door have lifetime warranty. The ceiling was sound proofed so one can confidently say it is the quietest unit in the entire coop! Both bedrooms can accommodate queen sized beds and there is TONS of closet space!

355 Route 111 Unit #19, 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

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