Smithtown Homes for Sale

Welcome to Smithtown, a picturesque gem nestled in the heart of Suffolk County, New York. This charming town offers a perfect blend of suburban tranquility and vibrant community life, making it an ideal place to call home. With its rich history dating back to the 17th century, Smithtown boasts a unique character that’s reflected in its quaint downtown area, lush parks, and scenic waterfront along the Nissequogue River.

Smithtown is renowned for its top-rated schools, making it a family-friendly destination. Residents enjoy a variety of recreational activities, from hiking and biking along the numerous trails to exploring the local shops and eateries that give this town its warm, welcoming vibe. The annual events, including fairs and farmers' markets, foster a strong sense of community that residents cherish.

For those seeking to plant roots in this lovely town, Smithtown offers an enticing array of homes for sale. From charming single-family residences with spacious yards to modern townhouses and cozy condos, there’s something to suit every lifestyle and budget. Many homes feature beautiful architectural details, updated amenities, and proximity to local parks and schools, ensuring that you can find your perfect sanctuary.

With its idyllic setting, strong community spirit, and diverse housing options, Smithtown is more than just a place to live; it’s a place to thrive. Explore the homes for sale today and discover the vibrant lifestyle that awaits you in this enchanting New York town!

Newest Smithtown Homes for Sale

$759,999

4 Beds ⋅ 2 Baths ⋅ 1060645 MLS

Welcome to 23 Hillcrest Drive, Smithtown! — where modern elegance, timeless charm, and the beauty of North Shore living come together! Situated on an expansive half-acre-plus property, this beautifully reimagined residence offers the perfect combination of sophisticated finishes, versatile living spaces, and an exceptional location. LOW TAXES OF ONLY $8650! From the moment you arrive, the home's impressive curb appeal sets the tone, featuring new siding, Brand 30 year architectural roof, elegant stone front steps and walkways, refreshed front and rear entryways, a newly paved blacktop driveway, and a detached garage offering additional parking and storage. Step inside to discover beautifully refinished hardwood floors, recessed lighting throughout, and a bright, inviting atmosphere. The stunning renovated kitchen features calacatta countertops, brand-new cabinetry, stainless steel appliances, and modern porcelain tile flooring. Beautifully updated bathrooms, including a spacious double vanity on the main level, bring modern comfort and sophistication to everyday living. The fully finished basement, complete with laminate flooring and a full bathroom, provides exceptional flexibility for extended family, guests, entertaining, or a potential mother-daughter arrangement or accessory dwelling unit (ADU), subject to proper permits and municipal approvals. Additional improvements, including upgraded 200-amp electrical service, further enhance the home's appeal. Beyond the property, enjoy the quintessential North Shore lifestyle, with its charming surroundings, nearby parks, recreational destinations, and vibrant local amenities. Conveniently situated near the Long Island Rail Road, major shopping centers, restaurants, and essential commuter routes, this location offers the perfect balance of suburban tranquility and everyday accessibility. With over half an acre of property, a detached garage, extensive modern upgrades, and the versatility to accommodate a variety of lifestyles, 23 Hillcrest Drive presents an exceptional opportunity to enjoy the very best of Smithtown living. Move right in, spread out, and make this beautifully transformed residence your next place to call home!

23 Hillcrest Drive, Smithtown

$1,149,999

4 Beds ⋅ 3 Baths ⋅ 1059779 MLS

Welcome to 2 Three Pond Road.... This Yablonski built Center Hall Colonial is set on 1 Acre of Beautiful Property, located in the "Prestigious Grange Estates" of North Smithtown! Step inside to your grand entry foyer, formal dining room, EIK w/ top-of-the-line Imported Brazilian Stone Granite counter tops, double oven and updated SS appliances, Formal Living room w/ dual sided wood burning fireplace flowing seamlessly into the expansive den, bath powder room, and custom-built sun room w/ exquisite stone walls and built-in hot tub for tranquil relaxation, along w/ easy interior access to your 2 car attached side entry garage... upstairs you have your primary bedroom w/ private bidet and toilet room with separate shower/spa jacuzzi room, 3 additional generously sized bedrooms, Office space and/or 5th bedroom (or WIC potential), and additional full hall bathroom. Step outside to your private resort like back yard w/ mature privacy trees and professionally designed landscaping surrounding, a resort style IG pool w/ a gradual sloped bottom, custom-built pavilion area, gazebo, oversized Trex deck and tranquil waterfall.... creating the perfect setting for peaceful evenings and ultimate relaxation. Additional features include the following…. In Ground 20x40 Pool (Liner 2025) w/ a solar assisted heating system, CAC (1 Zone – 2018), Oil Heat (1 zone), Single Layer 30-year architectural Roof (2018), Hardwood floors throughout, 200 AMP electric, expansive paver driveway beautifully appointed to the side entry 2-car garage… all this and so much more set on a picturesque acre private corner lot w/ exquisite bluestone walling surrounding, cascading Waterfalls and fountains, lush nature and tranquility, you do not want to miss this!

2 Three Pond Road, Smithtown

$499,999

1 Beds ⋅ 1 Baths ⋅ 1052134 MLS

Welcome to 8 South Avenue, a charming one-bedroom, one-bath cottage situated on approximately 0.38 acres in Smithtown. The home features an updated kitchen, hardwood and vinyl flooring, and a functional layout filled with natural light. Step outside to a spacious, fully fenced backyard complete with a 4-zone in-ground sprinkler system, large detached garage/shed, and plenty of room to enjoy the outdoors. Notable improvements include a roof replaced in 2019, updated living room windows, driveway, and gutters. Oil heat, a utility basement, and remarkably low taxes of approximately $4,393 add to the appeal. 8 South Avenue combines a sizable property, low taxes, and room to make it your own.

8 South Avenue, Smithtown

$899,999

4 Beds ⋅ 2 Baths ⋅ 1059410 MLS

Absolutely stunning, turnkey Hi-Ranch in the Smithtown School District, perfectly situated mid-block on a beautiful tree-lined street. Meticulously maintained and thoughtfully updated, this 4-bedroom, 2-full-bath home combines comfortable everyday living with exceptional spaces for entertaining. The heart of the home is the impressive custom kitchen featuring granite countertops, beautiful cabinetry, stainless steel appliances, radiant heated floors and a large center island ideal for entertaining or casual meals. The kitchen flows seamlessly into the dining and living areas, where abundant natural light, hardwood floors and a dramatic cultured-stone accent wall surrounding the wood-burning fireplace create a warm and inviting atmosphere. Downstairs, the spacious and versatile lower level offers tremendous flexibility for a den, family room, home office or guest space, with large sliding glass doors opening directly to a covered patio and your own resort-style backyard. Outside is where this home truly shines. A large second-story composite deck overlooks the heated in-ground pool with waterfall, professionally paved patio areas, pergola and fully fenced yard—creating an incredible setting for summer entertaining, relaxing by the pool or enjoying a quiet evening at home. Additional features include central air conditioning, radiant heated tile floors, a two-car attached garage, large driveway, private laundry area, full attic, storage shed, in-ground sprinkler system, vinyl fencing and more. Move-in ready inside and out, with an incredible backyard and a location that's hard to beat—this is the Smithtown home you've been waiting for.

31 Sterling Lane, Smithtown

$689,999

2 Beds ⋅ 3 Baths ⋅ 1058725 MLS

Welcome to Willow Wood at Smithtown, a remarkable townhouse development featuring the stunning Apple Wood model with 1,900 interior square feet. As you enter, you’re greeted by a spacious foyer bathed in natural light from a skylight, leading to an open staircase that ascends to the second floor. Upstairs, you’ll find a well-designed layout that includes a primary en suite with two walk-in closets and a double vanity featuring both a tub and shower, alongside a second bedroom, also with a walk-in closet. Conveniently located off the bedroom is a laundry room for easy access. Returning to the main level, the cozy living and dining room combination showcases engineered hardwood floors and a gas fireplace, with sliding doors that open to a private patio—ideal for outdoor relaxation. The spacious eat-in kitchen is perfect for gatherings, while a conveniently located powder room and ample closet space throughout ensure both comfort and functionality. The home also includes a one-car garage with an electric opener, offering additional parking and storage solutions. For added security, the property is fully alarmed with Ring cameras at the front door and garage door. Monthly common charges of $500.00 includes landscaping and maintenance, access to the inground saltwater pool, clubhouse, and fitness center, snow removal, and water, along with discounts on Optimum TV and Internet services. Community amenities further enhance the living experience with an inground pool, clubhouse, fitness center, and a relaxing gazebo, all in a pet-friendly environment. Don’t miss out on this exceptional chance to live in a vibrant community at Willow Wood in Smithtown!

5 Monitor Road, Smithtown

$899,999

4 Beds ⋅ 3 Baths ⋅ 1058590 MLS

Welcome to 24 Frank Street!! This Spacious center hall colonial features a beautiful open floor plan with a large entry foyer, formal living room (or formal dining area if preferred), Great room w/ wood burning FP, spacious dining area, EIK w/ SS Appliances and Granite Counter tops, 1/2 bath powder room, Laundry Area and access to your heated (+AC Wall unit) attached 2-car attached garage! Upstairs you have a spacious primary bedroom w/ WIC, sitting area and full bathroom, 3 additional spacious bedrooms and full hall bathroom. The partially finished basement features an oversized recreation area w/ brand new carpet and ample storage space! This home is Situated on a professionally landscaped 1/2 acre of flat property with an IG heated pool, oversized paver patio, and Trex deck area w/ Cabana. Additional features include the following… Natural Gas Heat (3 zones – Burner 2022), CAC (1 zone - 2017), 50 Gallon Gas Hot Water tank (2022), 200 AMP Electric, Roof 1 Layer 30 Year Architectural w/ 25-year warranty (2023) – skylights updated same time, Updated Anderson windows/slider doors, IG Sprinkler System (15 Zones), IG Heated Pool (Liner – 2016). All this and so much more on a private .50-acre lot, you do not want to miss this!!

24 Frank Street, Smithtown

$1,189,000

4 Beds ⋅ 4 Baths ⋅ 1053324 MLS

Welcome to this grand, stately Colonial, beautifully landscaped and set on a private, fenced-in 1/2-acre lot. The property offers an exceptional setting for entertaining and enjoying the outdoors, complete with a gunite pool, charming gazebo, house generator, and two-car garage for added convenience and peace of mind. Inside, the home offers four bedrooms, three full bathrooms, one-half bathroom, a versatile den that can also be used as a home office, and two fireplaces. Beautiful hardwood floors extend throughout the main level, adding warmth and timeless elegance. A spacious formal living room and dining room provide an ideal setting for both everyday living and entertaining. The formal living room features a wood-burning fireplace, creating a warm and inviting atmosphere. The thoughtfully expanded kitchen offers an open and welcoming space for cooking, gathering, and enjoying time with guests, complemented by a beautiful gas fireplace that adds warmth and ambiance. The finished basement provides additional versatile space, along with a private outside entrance and bathroom. Step outside to enjoy a beautifully landscaped retreat designed for relaxation and summer entertaining. The expansive fenced-in grounds provide plenty of space to unwind, gather with guests, and create lasting memories. With its generous floor plan, elegant details, versatile finished space, two-car garage, and exceptional setting, this remarkable Colonial offers comfort, character, and an ideal blend of indoor and outdoor living.

28 S Lot Road, Smithtown

$699,000

3 Beds ⋅ 3 Baths ⋅ 1058587 MLS

Discover the perfect blend of modern updates, timeless appeal, and comfortable living in this beautifully updated 3-bedroom, 3-bath ranch in St. James. The inviting interior showcases hardwood floors, a welcoming living room with fireplace, and an updated kitchen featuring elegant quartz countertops and a breakfast bar. The finished lower level with a separate outside entrance offers exceptional flexibility for recreation, a home office, guests, or additional living space. Outdoors, enjoy a fully fenced property complemented by a stone patio and storage shed, creating an inviting setting for relaxation and entertaining. Additional highlights include gas heat and cooking. Ideally located directly across from a park and playground, with convenient access to shopping, dining, schools, and transportation. Thoughtfully updated and move-in ready, this home offers the perfect balance of style, functionality, and location.

296 Moriches Road, Smithtown

$1,199,999

5 Beds ⋅ 5 Baths ⋅ 1044455 MLS

Two distinct living spaces, one extraordinary property! Tucked down a long, private driveway off of Carrie Court, this home offers 4,198 square feet of living space in the Smithtown School District. The spacious main home and attached second living area each have a separate entrance and driveway, providing generous parking and a flexible layout. Real wood cedar siding, mature landscaping, raised stone flower beds, and custom wood entry details make a memorable first impression. Inside the main home, hardwood floors, crown and door molding, recessed lighting, and skylights set the tone. The formal living room features soaring vaulted ceilings and a dramatic three-sided stone wood-burning fireplace. The chef’s kitchen pairs deep espresso-toned Shaker cabinetry with white upper cabinets, glass-front accents, granite countertops, under-cabinet lighting, stainless steel appliances, a Viking gas cooktop, double ovens, dishwasher, built-in microwave, oversized stainless steel double sink, separate vegetable sink, garbage disposal, breakfast bar, and tile backsplash. It opens to an expansive dining room with vaulted ceilings, upper windows, a wall of windows overlooking the backyard, and French doors leading outside. Plantation shutters grace many of the first-floor windows. First floor also features a spacious den/great room, featuring recessed lighting, beautiful wood floors and custom molding. Upstairs, the primary suite occupies its own level, with bamboo flooring, custom shoji-style closets, a translucent screen wall, and a spa-inspired bath featuring radiant-heated floors, a Jacuzzi soaking tub, and an oversized glass-enclosed shower. A loft with vintage oak flooring, vaulted ceilings, and recessed lighting offers flexible space that could serve as an additional bedroom or home office. Two more bedrooms and a full bath with dual glass vessel sinks complete the upper level. The main home’s at-grade lower level has its own entrance, full bath with a glass-enclosed shower, recessed lighting, and box molding. The attached second living area has a separate entrance, oak flooring, crown molding, recessed lighting, a powder room, and a stunning kitchen with double-height ceilings and clerestory windows. Antique-glazed cream custom cabinetry, Viking gas cooktop, double ovens, farmhouse sink, granite countertops, floor-to-ceiling pantry storage, and a sage-green island with carved corbels make this space exceptional. Its primary suite features vaulted ceilings and a beautifully finished bath with Carrara-style marble, a walk-in shower, built-in seat, and custom vanity. Outside, discover a resort-style backyard with a freeform in-ground pool, Trex decking, estate fencing, outdoor shower, slate and paver patios, and multiple spaces to gather or unwind. Additional features include three-zone heating and air conditioning, a gas-powered Generac whole-house generator, a 300-amp electrical panel, and 13-zone in-ground sprinklers. Town of Smithtown records identify the property as a one-family dwelling with a special exception for separate living quarters. The exception does not transfer to a new owner; a buyer would need to reapply with the Town.

100 Edgewood Avenue, Smithtown

$1,195,000

5 Beds ⋅ 3 Baths ⋅ 1055906 MLS

Completely Renovated Historic 3 story Colonial on private 1.3 Acre parcel with circular driveway blends a bright modern feel with classic architectural elements to create a showcase for your style. Stately front to back entrance foyer sets the tone. Dual Staircase, High Ceilings, Substantial Moldings, Hardwood Floors and 5 Fireplaces all add to this unique and desirable property. Relax in the knowledge that heating and cooling systems, appliances, roof and windows have been replaced in the last 6 years. Outdoor Patio is perfect for private dining. Detached 2 Car Garage. Barn and Potting Shed (as-is) Direct access to the 93 Acre Arthur H Kunz County Park on the Nissequogue River and minutes from Smithtown Landing Country Club proves to be a rare location. Easy access to shopping, main roadways and beaches! Smithtown School District

592 Landing Avenue, Smithtown

$1,399,000

4 Beds ⋅ 3 Baths ⋅ 1055810 MLS

Located in the highly sought-after enclave of Smithtown Pines, this beautifully renovated home delivers the expansive feel of a private upstate retreat right on Long Island. Set within the Hauppauge School District, every detail of this exceptional property has been thoughtfully executed, from the professionally landscaped grounds and impressive masonry work to resort-style backyard. Rich, glowing hardwood floors flow throughout the main level, complemented by a light-filled living room centered around a fireplace with built-in shelving and a formal dining room featuring a statement chandelier and picture window. The custom chef's kitchen serves as the heart of the home, equipped with a waterfall Calcutta quartz center island, Monogram induction cooktop and double ovens, Futuro Italian range hood, Miele under-counter combi-steam oven, Monogram refrigerator and dishwasher, and a built-in Brio water dispenser. Sliding glass doors open to a 600-square-foot deck, structurally reinforce to accomodate a future enclosed room, overlooking the pool, stone gardens, and firepit. The primary suite features plantation shutters and a private ensuite bath with custom cabinetry and a walk-in shower. Primium Pella Series windows and high-end hardware are featured throughout. The finished lower level offers exceptional space for extended living or multi-generational flexibility, with a spacious family room featuring sliders directly to the pool, a generously sized fouth bedroom, a beautifully renovated full bath, and a laundry area concealed behind designer doors. A generous summer kitchen with ample dining space opens direclty to the patio and firepit area, with an adjoining pantry and additional exterior access-perfect for entertaining and effortless poolside living. Outdoors, the fully fenced and updated pool is framed by mature landscaping and dramatic Pennsylvania boulders, with a thoughtfully carved-out area ready for a future hot tub. Stone steps wind through the property, passing a peaceful gazebo before continuing to the upper grounds, where a sports court awaits your personal touch. Approximately half an acre of open lawn provides abundant room for recreation, entertaining, and outdoor activities. The oversized two-car garage includes a dog shower, EV charging, and generator hookup, with additional exterior EV charging capability. Notable updates include a 20-year roof, central air conditioning, a newly completed driveway, 200-amp electrical service, front and rear sprinkler systems, and a boiler and hot water heater approximately three years old. Gas is available at the street for a future conversion.

47 McArthur Lane, Smithtown

$629,900

3 Beds ⋅ 1 Baths ⋅ 1036399 MLS

Welcome home to 36 Mayflower Avenue, a beautifully renovated ranch where no detail has been overlooked and every update was made with care and intention. From the moment you arrive, the new front pavers, fresh siding, and a new stoop sets the tone for what's inside. Major mechanicals have all been taken care of such as a new water main, 200 amp electrical upgrade, new plumbing, and central air conditioning. You can move in with complete peace of mind. Inside, you'll fall in love with the renovated kitchen and bathroom. The living room is an absolute showstopper, featuring in-ceiling speakers with motion-detected digital surround sound, perfect for cozy nights in or entertaining guests. Anderson, Pella, and Velux windows flood every room with natural light, and the skylights with motorized blinds add a touch of luxury you didn't know you needed. Outside you're welcomed with a fully fenced backyard complete with beautiful pavers and a retaining wall, your own private retreat, ready for summer gatherings and quiet evenings alike.

36 Mayflower Avenue, Smithtown

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.