Smithtown NY Real Estate, Homes, Condos for Sale

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

4 Smithtown Crescent, Smithtown

$775,000

3 Beds ⋅ 2 Baths ⋅ 1031716 MLS

WHERE TIMELESS CHARM MEETS EXCEPTIONAL OPPORTUNITY. Discover the warmth, character, and enduring appeal of this beautifully maintained Colonial, ideally situated in one of Smithtown’s most desirable neighborhoods. Rich hardwood floors, an inviting fireplace, and flowing floor plan create an atmosphere that feels instantly like home. Offering three spacious bedrooms and one-and-a-half baths, this residence features a gracious living room with fireplace, Dining room, and eat-in Kitchen. The partially finished basement provides abundant storage while offering potential for additional living space. Step outside and experience a setting that feels straight from the pages of a storybook. Meandering stone pathways weave through mature landscaped gardens, leading to an expansive fenced backyard that invites summer gatherings, outdoor celebrations, or simply peaceful evenings surrounded by nature. Perfectly positioned on a quiet residential street, this exceptional home offers the tranquility buyers seek while remaining just minutes from the Long Island Expressway, Northern State Parkway, shopping, dining, and all that the Town of Smithtown has to offer—including its renowned parks, beaches, and recreational amenities. Whether you’re searching for your forever home or a rare opportunity in one of Long Island’s most sought-after communities, this residence offers the perfect blend of charm, comfort, location, and future potential.

20 Brook Lane, Smithtown

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1030904 MLS

This Pristine Dream Home, Nestled on a Meandering Wooded Street in the Pines, is Ensconced in a Peaceful, Perennial Paradise! The Lushly Landscaped & Lovingly Tended Property, as Meticulous Outside as the Home is Inside, Compels you to Linger on the Covered Porch or Back Patios, just to drink in the View! Inside, a Grand Foyer Shines with its Soaring Ceiling, Stunning Imported Crystal Chandelier & Exquisite Custom Millwork, here & throughout the Home. Attention to Fine Detail is Evident in each room, from the Elegant Formal Dining Room with Custom Window Seat to the Chef's Kitchen with new Stainless Appliances and Family Room w/ Garden Views for Summer & Fireplace for cozy Winters. The Radiant Heated Floors on this Floor Welcome the Colder Seasons! Ascend the Open Staircase to the Bedroom floor with it's Generous Landing & Lovely, Spacious Rooms. Look forward to beginning & ending each day, when your Primary Bedroom is your personal Suite Escape. The New Custom Designed EnSuite is Resplendent in Marble with Tasteful Accents that Highlight the Soaking Tub & Glass Enclosed Shower in the Most Beautiful Way! This Home's Beauty is not only Seen, it's Felt...from the minute it beckons you in, you know you'll want to stay. If you need more reasons to stay, here they are: The "Forever Slate" Metal Roof w/ Transferable Lifetime Warranty (home & shed), All New Andersen Windows (20 Yr Transferable Warranty), Whole House Generator, Whole House Water Filter System, 2 Zone Lennox Elite Central Air, Bosch High Efficiency Boiler & Tankless Water Heater, Electric Car Charger, Owned Solar Panels, Central Vacuum. Move-In Ready! The Season is Ideal to Enjoy All this Home has to Offer, Indoors & Out. Relax in the Garden & Entertain on the Patios, before the Autumn Colors & Snowfall Holidays begin. Isn't it Time to Stop Dreaming and Start Living the Dream? Your Best Long Island Life Awaits!

35 Pine Ridge Drive, Smithtown

$699,999

3 Beds ⋅ 1 Baths ⋅ 1030650 MLS

Well maintained cozy ranch on tree lined street in Smithtown on .63 property with a detached garage. This home offers a formal living room, dining room, den, eat in kitchen, w/propane cooking as well as 3 bedrooms and 1 full bathroom. There are Anderson windows, hardwood floors in Living room.

42 Pineacre Drive, Smithtown

$800,000

4 Beds ⋅ 3 Baths ⋅ 1030391 MLS

Sprawling Smithtown Ranch on .52 Acre with Gunite Pool & 3-Car Garage! Space, flexibility and a backyard built for summer living come together in this distinctive 4-bedroom, 2.5-bath home set on a beautiful .52-acre property in the desirable Smithtown School District. Offering the ease and open feel of ranch-style living with a thoughtfully designed split-level bedroom wing, this home provides an exceptional layout for both everyday living and entertaining. A welcoming foyer opens to generously sized living spaces, including a formal living room, formal dining room, expansive den and a separate home office—ideal for working from home or creating a quiet flex space. The eat-in kitchen features granite countertops, stainless steel appliances and direct access to the deck, backyard and pool, making indoor-outdoor entertaining easy. Just a few steps above the main living area are four bedrooms and two full baths, creating separation and privacy without sacrificing the convenience of a ranch-style layout. The spacious primary suite features walk-in closets and a private bath with a sunken tub. The partially finished basement provides additional flexible space along with plenty of storage. Outside is where this property truly shines. Enjoy more than half an acre with a gunite inground pool and waterfall feature, a spacious deck for outdoor dining and entertaining, and an inground sprinkler system. A circular driveway and rare 3-car attached garage provide abundant parking and storage. Gas heat, central air conditioning and public sewer add to the home's everyday comfort and convenience. If you've been searching for generous living space, a private backyard retreat and an exceptionally versatile layout in the Smithtown School District, 29 Ivy Hill Drive deserves a closer look.

29 Ivy Hill Drive, Smithtown

$825,000

4 Beds ⋅ 2 Baths ⋅ 1030021 MLS

Welcome Home to Unmatched Space & Craftsmanship in Smithtown! Nestled in the top-rated Commack School District, this meticulously maintained Hi-Ranch has been dramatically transformed by a huge 2-story extension, offering incredible size, flow, and modern luxury. Step inside to find rich hardwood floors and an open, light-filled layout. The expansive upper level culminates in a jaw-dropping Great Room designed for effortless entertaining, leading seamlessly out through double doors to a grand covered deck. Modern essential utilities include Central Air Conditioning and Natural Gas heating and cooking. Lower level offers immense flex space with bedroom, full bath, and family room. Step into a backyard paradise featuring a custom paver patio and built-in fire pit—ideal for cool nights under the stars. Conveniently located near top schools, parks, and major parkways. Turnkey living at its absolute finest!"

20 Hunter Place, Smithtown

$990,000

4 Beds ⋅ 3 Baths ⋅ 1029417 MLS

Set on a beautifully landscaped 0.80-acre corner property, this custom Farm Ranch offers space, comfort, and exceptional versatility. A welcoming entry foyer opens to a recently renovated eat-in kitchen featuring a striking double-sided fireplace. The bright and airy den is surrounded by walls of windows, while the formal dining room provides easy access to the deck through sliding glass doors. The main level also includes a spacious living room with a custom window seat and a convenient powder room. The first-floor primary suite is designed as a private retreat, complete with a sitting area or home office, a walk-in closet, and an oversized bath featuring a soaking tub and separate walk-in shower. Three additional bedrooms and a full hall bath provide plenty of room for family or guests. The full, partially finished basement offers an outside entrance, laundry area, utilities, and abundant storage or expansion potential. Additional highlights include radiant heat, hardwood flooring, central air conditioning, in-ground sprinklers, Andersen windows, a 150-amp electrical service, generator hookup, updated paver walkways, a roof replaced in 2021, burner installed in 2020, and a hot water heater replaced in 2021. Ideally located near town beaches, Landing Avenue Golf Course, the LIRR, shopping, and dining. This spacious home offers endless possibilities and is much larger than it appears.

19 Eckernkamp Drive, Smithtown

$799,900

4 Beds ⋅ 2 Baths ⋅ 1028706 MLS

Welcome to 41 Oak Street. This inviting High Ranch offers exceptional curb appeal with stately pillars, shingle style vinyl siding, Fieldstone accents, paver walkways, a charming Arbor enhancing the entrance to the backyard and an oversized Belgian Block lined driveway. The home is surrounded by mature landscaping offering natural privacy and a serene setting. Step inside to discover gleaming hardwood floors, sunlit living spaces enhanced by bay and bow windows, custom hand carved wood detailing and stain glass accents that create a warm inviting ambiance. The beautifully appointed kitchen, expansive den with a large skylight and a tastefully renovated full bathroom further enhance the home’s appeal. The versatile lower level offers excellent potential for extended living with proper permits. The sliding glass doors leads to your own private retreat. Multi-level Trex and wood decking with handcrafted built in benches, tiered wood walkways, a custom awning, tranquil fish pond, and a sparkling 20x40 in ground pool surrounded by stone pavers featuring a new liner complete this thoughtfully designed outdoor space. Additional highlights include a new 275 gallon Roth Oil tank, 200-Amp electrical service, a new first floor central air conditioning system, and a roof and siding that are approximately 20 yrs. old. Conveniently located near Smithtown Beaches, Smithtown Landing Golf and Country Club. All of-this is set on .50 acres in a truly desirable location. Don’t miss this wonderful opportunity to make this home your own and create lasting memories for years to come.

41 Oak Street, Smithtown

$979,000

4 Beds ⋅ 3 Baths ⋅ 1029017 MLS

Under Construction – Your Opportunity to Own a Beautifully Renovated Home in Smithtown! Welcome to this stunning 4-bedroom, 2.5-bath splanch, currently under a full renovation with today's modern buyer in mind. Upon completion, this home will feature a spacious and modern layout with high-quality finishes throughout. With the main floor having a Beautiful modern kitchen and a formal dining room. Also a comfy den and half bath, The Second floor will have a very large living room/family room. Beautifully finished wood floors throughout with all new lighting and central air. New windows and crown moldings throughout. * Cover photo is an AI rendering of finalized renovation* On the 3rd floor The primary suite will include a full bath and walk in closet. The 3rd floor will also have a full bath plus 3 very large bedrooms The house also has a large fenced in yard perfect for entertaining! Finally beautiful landscaping finishes throughout will provide privacy and great curb appeal

30 Glacier Drive, Smithtown

$775,000

3 Beds ⋅ 2 Baths ⋅ 1027993 MLS

Welcome home! This pristine 3-bedroom, 2-bathroom Splanch sits perfectly on a flat, fenced .25-acre lot in a sought-after, sidewalk-lined neighborhood. Beautifully merging modern updates with exceptional energy efficiency, this residence is entirely turn-key. From the moment you arrive, the new double-wide paver driveway provides the convenience for parking multiple cars without the chaos. Enjoy the newer kitchen and updated bathrooms. Bright sliders lead directly from the home to a brand-new deck, perfect for summer barbecues and outdoor dining or relax by the warm gas fireplace in your inviting main living space. Stay comfortable year-round with efficient gas heating and central air conditioning in a home that is fully equipped with solar panels to drastically lower your monthly electric bills. This property is situated in the Smithtown School District. It offers easy access to the town's Main Street, dining, and shopping, as well as gorgeous state and county parks. Commuting is effortless and convenient to major highways and the Long Island Rail Road (LIRR). Everything you could want is waiting for you right here.

11 Sandalwood Drive, Smithtown

$725,000

3 Beds ⋅ 3 Baths ⋅ 1028158 MLS

Welcome to Hidden Ponds, a beautiful gated community in the heart of Smithtown. This end-unit townhouse offers the perfect combination of comfort, style, and convenience with 3 spacious bedrooms, 2.5 bathrooms, and natural gas heating and cooking. The welcoming open-concept main level features a beautifully renovated eat-in kitchen with stainless steel appliances, a massive center island, abundant pantry storage, and seamless flow into the living and dining areas. Hardwood flooring extends throughout the first floor, which also includes a laundry room, powder room, and attached garage. Sliding glass doors lead to a private composite deck overlooking the peaceful greenbelt path, while established flower gardens add charm and privacy. The Upstairs, the expansive primary suite offers a private ensuite bathroom, two walk-in closets, and a versatile office or flex space. Two additional generously sized bedrooms, a full bathroom, and soaring vaulted ceilings complete the second level. Residents of Hidden Ponds enjoy exceptional amenities, including a clubhouse with a kitchen, movie/card room, fitness center, outdoor pool, tennis and pickleball courts, basketball court, bocce ball, playground, mailroom, extended driveway, and ample guest parking. Experience the perfect blend of comfort, convenience, and resort-style living in one of Smithtown’s most desirable gated communities.

300 Pond View Lane, Smithtown

$3,995,000

7 Beds ⋅ 6 Baths ⋅ 1022766 MLS

Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.

38 Landing Meadow Road, Smithtown

$949,999

4 Beds ⋅ 3 Baths ⋅ 1028029 MLS

Welcome home to this stunning, meticulously maintained Colonial in the renowned Commack school district. Thoughtfully expanded with additional living space, this home offers room to grow, entertain, and unwind in style. Step outside into your own entertainer's paradise — a country club-worthy backyard featuring a sparkling saltwater in-ground pool (complete with a brand-new pump). Inside, quality craftsmanship shines throughout: gleaming hardwood floors, a cozy fireplace, energy-efficient Andersen windows, recessed lighting, and a sun-drenched skylight create a warm, elevated living experience. The spacious basement offers even more flexible space for a home gym, media room, or playroom. Outside, practicality meets curb appeal with a double-wide driveway, electric garage door opener, and three sheds for all your storage needs.

29 Sandy Hollow Drive, Smithtown

$1,699,000

5 Beds ⋅ 6 Baths ⋅ 1027754 MLS

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

14 Loft Road, Smithtown

$575,000

3 Beds ⋅ 2 Baths ⋅ 1027092 MLS

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

39 William Street, Smithtown

$985,000

4 Beds ⋅ 3 Baths ⋅ 1026048 MLS

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

103 Redan Drive, Smithtown

$869,000

4 Beds ⋅ 3 Baths ⋅ 1026666 MLS

Welcome to this exceptional 4-bedroom, 2.5-bath Splanch located in the prestigious East Hill Estates section of Smithtown. Offering approximately 2,380 square feet of beautifully designed living space, this residence seamlessly blends timeless elegance with everyday comfort. A gracious floor plan features sun-filled living areas, a warm and inviting fireplace, spacious formal and casual gathering spaces, and a well-appointed kitchen designed for both entertaining and daily living. The generous primary suite provides a peaceful retreat, while three additional bedrooms offer flexibility for family, guests, or a home office. Enjoy year-round comfort with an updated HVAC system, providing efficient heating and cooling throughout the home. Step outside to your private backyard oasis featuring a heated in-ground salt water swimming pool, expansive patio with gas BBQ connection , and beautifully landscaped grounds—perfect for outdoor entertaining or relaxing all summer long. Additional highlights include an attached two-car garage, a full basement offering abundant storage and future finishing potential, and pride of ownership throughout. Ideally situated in the award-winning Smithtown Central School District, the home is conveniently located near parks, golf courses, shopping, dining, beaches, major parkways, and the Long Island Rail Road. This is a rare opportunity to own a beautifully maintained home in one of Smithtown’s most sought-after neighborhoods, where classic Colonial charm meets modern comfort.

6 Navy Drive, Smithtown

$825,000

4 Beds ⋅ 2 Baths ⋅ 1026298 MLS

Welcome to this meticulously maintained 4 bedroom, 2 full bath expanded Cape situated on a beautifully landscaped, flat half-acre property. This warm and inviting home features a spacious living room with a fireplace, formal dining room, and hardwood floors throughout. Pride of ownership is evident in the many updates, including a new roof, newly renovated bathrooms, new air conditioner, Andersen windows, and updated 200-amp electric service. Custom kitchen cabinets with Corian counter tops, and butcher block center island. The detached garage offers ample storage and workspace, while the expansive property provides plenty of room for outdoor enjoyment. Combining timeless charm with modern conveniences, this exceptional home is conveniently located near parks, shopping, restaurants, and major roadways. All information deemed accurate but should be independently verified.

119 Brook Lane, 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

$999,000

4 Beds ⋅ 3 Baths ⋅ 1020597 MLS

When opportunity knocks the door must be opened. Welcome to 57 Brooksite Drive. A stunning single unit home in the heart of Smithtown NY sitting on nearly a half an acre of property. Renovated just over 1 year ago this home is being offered to the market at an amazing opportunity to be purchased as turn key as they come. Enjoy the state of the art renovations throughout the property including a finished basement, a first floor master bedroom, and an open concept dining room & kitchen. Spark up the fire and sit with the entire group as you enjoy the fully functional living room fireplace. Walk out your sliding door and gaze at your massive nearly half acre of land where you can host and entertain your friends. Got a project? Your attached garage gives you plenty of space to park your car and sustain your handyman fix. This property needs absolutely nothing except your willingness to enjoy it's perfection. This is a truly ICONIC home!

57 Brooksite Drive, Smithtown

$799,999

4 Beds ⋅ 3 Baths ⋅ 1024943 MLS

Welcome to 44 Winslow Lane, Smithtown! Located in a highly desirable neighborhood within the Smithtown School District, this beautifully maintained 4/5 -bedroom,2.5 bath Ranch offers the perfect blend of comfort, style and functionality..Updated EIK w/Granite Countertops,stainless steel appliances,Formal Living Room,Dining Room,Family Room w/Wood burning Fireplace,hardwood floors,2 bedrooms w/ new carpet,200 amp electric,2024 gas burner, CAC,IGS,2 Car Garage, leaf guard gutters, freshly power washed and soft roof washed, Set on beautiful 0.35 acre lot Don't miss this exceptional opportunity to own this beautiful home

44 Winslow 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

$1,749,999

5 Beds ⋅ 4 Baths ⋅ 1023719 MLS

Welcome to Plymouth Estates, a 5 lot subdivision in the prestigious neighborhood of Smithtown, NY. This NEW CONSTRUCTION subdivision on a cul-de-sac offers 5 exceptional lots, with 5 bedrooms, 3 full bathrooms, 1 half bathroom, eat-in kitchen with a large center island, granite/quartz countertops, SS Appliances, double wall ovens, wine fridge, gas cooktop, mudroom with pantry, family room with gas fireplace, living room, dining room, office/study, hardwood floors, crown molding, raised panel molding, primary bedroom with en-suite bathroom, large soaking tub, walk-in closets, 4 additional large bedrooms, and laundry room. 2 car garage, full basement with 9ft. ceilings, egress window and 2 entrances. Taxes to be determined. Currently offering two models, The Villager and The Gazebo. Nestled in the heart of Smithtown, This stunning development promises luxurious living and convenient access to various amenities, including shopping, dining, schools, and recreational facilities. With easy access to major transportation routes, commuting and exploring the area is effortless. Enjoy privacy and tranquility in this exceptional newly built development. 200 amp service, 2 zone gas heat, central A/C, 75 gal. hot water heater, central vacuum, system. Don't miss the chance to establish roots in this remarkable neighborhood.

3 Greentree Court, Smithtown

$999,999

4 Beds ⋅ 3 Baths ⋅ 1023260 MLS

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

20 Oak Tree Drive, Smithtown

$899,000

3 Beds ⋅ 3 Baths ⋅ 1023162 MLS

Welcome to this beautifully updated home, originally built in 2004 and thoughtfully enhanced with quality improvements throughout just 6 months ago . Taxes currently being grieved. Hearing all offers. Offering the perfect blend of modern updates and timeless comfort, this move-in-ready residence has had virtually everything replaced. Step inside to discover beautifully refinished hardwood floors that add warmth and elegance throughout the home. Enjoy peace of mind with all-new plumbing throughout, a brand-new roof just five months old, and a full suite of appliances that are only three months old. Each of the home's three bathrooms has been exquisitely remodeled just 5 months ago, using premium, top-of-the-line materials, creating luxurious spaces designed for everyday comfort. Additional highlights include in ground sprinklers, 200 amp electric, new high-hat lighting, efficient natural gas heating and hot water, central a/c, new paint, crown molding, along with a spacious two-car detached garage offering exceptional storage, workspace, or room for your favorite hobbies. Nestled on a quiet dead-end street and fully fenced within a highly sought-after school district, this home provides the perfect setting for peaceful living while remaining centrally located to shopping, dining, and the Long Island Rail Road just 1.6 miles away, making daily commuting both easy and convenient. Outdoor enthusiasts will appreciate the abundance of nearby recreational opportunities. Spend weekends exploring the scenic trails, fishing, or cross-country skiing at Caleb Smith State Park Preserve. Enjoy kayaking, river access, and a playground at Landing Avenue Park, or take advantage of the outstanding athletic facilities at Robert A. Brady Park, featuring baseball and softball fields, tennis and basketball courts, volleyball, and a roller hockey rink. With exceptional updates, an unbeatable location, this remarkable home presents a wonderful opportunity to enjoy modern living in an established neighborhood. Simply unpack and start making memories!

38 Hallock Avenue, Smithtown

$875,000

4 Beds ⋅ 3 Baths ⋅ 1015239 MLS

Well maintained Dutch Colonial on a corner lot in the beautiful Oakwood Forest neighborhood. This home is made for entertaining. Many upgrades throughout on the main floor and an office/flex space in the primary suite. Great closets! Your backyard oasis is ideal for barbeques or quiet dinners under the pergola or in the screened in porch, sitting around the firepit or swimming in the inground saltwater pool. Added highlights include solar panels for energy savings, 5-zone heating, tankless on demand water heater, updated bathrooms and kitchen. This house truly is a home!

16 Brook Lane, Smithtown

$269,999

1 Beds ⋅ 1 Baths ⋅ 1021899 MLS

Bright and inviting, this 1-bedroom, 1-bath second-floor co-op offers a comfortable, low-maintenance lifestyle in the heart of Smithtown. High ceilings and generous natural light create an airy, open feel throughout, giving you a great canvas to add your own personal touch. Step out onto your private balcony for a tranquil spot to unwind, or take advantage of the basement storage and on-site laundry for added convenience. The unit also features a newly installed oven/stove, dishwasher, and new carpeting throughout. With a monthly maintenance fee of just $1,223.83 — which includes property taxes — you're covered for gas heat, gas cooking, water, sewer, and all exterior care, making this a truly worry-free way to own. Conveniently located near major highways, this Tanglewood unit offers easy access for commuters and an easy commute into the city via the LIRR. Whether you're a first-time buyer or looking to make it your own, this Tanglewood unit offers a well-appointed space full of potential.

365 Route 111 Unit #A12, Smithtown

$1,250,000

6 Beds ⋅ 4 Baths ⋅ 1021652 MLS

Located in the in a highly desirable area of Smithtown sits this well maintained colonial…. Over 4000 sq ft of living area containing 6 true bedrooms, 3.5 bathrooms, a home office, a formal dining room, guest quarters (bedroom, full bath, living room) with a separate entrance, A sizable sitting room ( 18x25) containing a wood burning fire place, a separate living room and a wonderful screened in patio that can be accessed through the kitchen and the sitting room…. The landscaping of the home is just perfect!! Multiple sitting areas make it easy and fun to enjoy and entertain. A two car garage with electric car charging station, large driveway, close proximity to Town, LI Railroad and major highways just adds more value to this home.

10 Burham Drive, Smithtown

$1,374,000

4 Beds ⋅ 3 Baths ⋅ 1014247 MLS

Welcome to one of the most impressive properties to hit the market in The Pines. Set on a private half-acre of beautifully manicured grounds, this extraordinary contemporary ranch offers a perfect blend of luxury, comfort, and resort-style living—all in a beautifully landscaped, private setting. A long paved driveway leads to a spacious two-car garage and a grand entry foyer with soaring vaulted ceilings that create an unforgettable first impression. Inside, rich hardwood floors, custom moldings, skylights, and high-hat lighting create a warm, elegant ambiance, while central air conditioning throughout ensures year-round comfort. The sun-filled living room, highlighted by a stunning stone fireplace and skylights, features vaulted ceilings that enhance the open, airy feel. The formal dining room sets the stage for unforgettable gatherings. At the heart of the home is a breathtaking chef’s kitchen—boasting a massive granite island, farmhouse sink, custom cabinetry, premium Thermador appliances, and a bright dining area with a tray ceiling and a bow window overlooking the backyard oasis. Sliding glass doors open to a covered Trex porch, a patio, and a pool area—perfect for entertaining or unwinding. The luxurious primary suite is a true retreat—featuring a spa-inspired bath with vaulted ceilings, a jetted shower, and a spacious walk-in closet. The home also includes 2.5 baths, a wet bar with a wine cooler, a mudroom with abundant storage, California closets, and a finished lower level with heating, air conditioning, egress windows, and a large walk-in closet. And then, there’s the backyard. This is your private resort—complete with a spectacular 40-by-20 heated pool, rock waterfall, integrated spa, and complete privacy thanks to specimen plantings, landscape lighting, and PVC fencing. With a covered Trex porch, oversized storage shed, and a commercial-grade Generac whole-house generator, this home is a haven of comfort and convenience. Move-in ready and impeccably maintained—this is a rare opportunity to own a slice of paradise. Don’t miss out—this dream home won’t last long! Note 1 Bedroom Converted to a TV Room

6 Averly Place, Smithtown

$849,000

3 Beds ⋅ 2 Baths ⋅ 1019610 MLS

Nestled on a quarter acre of beautifully maintained property in the sought-after Morewood Estates section of North Smithtown, this immaculate ranch offers the perfect blend of comfort, updates, and flow. Walk the paver path from the oversized driveway into this updated home with gleaming hardwood floors, crown molding throughout, updated light fixtures and so much more! Updated bathrooms, 200-amp electric, and updated siding with a cultured stone facade. The fully finished walk-out basement provides an abundance of additional living and storage space, featuring a dedicated laundry room, multiple storage closets, and a second refrigerator; perfect for entertaining, holiday storage, or everyday convenience. Enjoy your own private backyard oasis. Beautifully landscaped and designed for entertaining. This home offers exceptional peace of mind with updates like a water purification system, Rheem gas furnace, 200 amp service and more. Meticulously maintained, this move-in-ready home is a rare opportunity you won’t want to miss!

7 Talbot Lane, Smithtown

$775,000

5 Beds ⋅ 3 Baths ⋅ 1021153 MLS

Beautiful well maintained five bedroom colonial. Tree lined street in Smithtown School District. Plenty of privacy in the backyard. Hardwood floors throughout, unfinished basement with cedar closet. Roof is eight years young, brand new boiler. Brand new 200 amp service.

39 Sheryl Crescent, Smithtown

$599,000

2 Beds ⋅ 2 Baths ⋅ 1020096 MLS

Welcome to the sought-after Emory Ranch in the gated Hidden Ponds community. This one story condo offers a spacious and inviting floor plan with 2 bedrooms, 2 full bathrooms, an attached garage, and an overized driveway for guest parking. The sun-filled eat-in kitchen features a charming breakfast nook and flows into the open-concept living and dining areas highlighted by soaring vaulted ceilings that create an airy, spacious feel. The generous primary suite offers a walk-in closet, an en-suite bathroom, and the most beautiful peaceful pond views. The second bedroom provides flexiblity to serve as a guest room, home office or den. Upgrades include cac, water heater, garage door. Additional conveniences include a hall laundry closet, washer/dryer and attic storage. Relax and enjoy the serene setting from your private outdoor patio space . Hidden Ponds offers resort-style living with a fully renovated clubhouse, kitchen, movie/card room, mail room, fitness center, ping-pong, bocce, heated saltwater pool, tennis/pickleball courts, playground , and dog park in this pet-friendly community. Located off 347 for easy access to major roadways, Smith Haven Mall, and Main Street Smithtown. With its desirable single-level layout, attached garage, and easy accessible location within the development, this home offers comfort, convenience and easy living in one of Smithtowns most desirable communities. This community has it all!

91 Hidden Ponds, Smithtown

$969,000

4 Beds ⋅ 3 Baths ⋅ 1018979 MLS

Welcome to 39 Merrivale Drive, a beautifully updated 4-bedroom, 2.5-bath expanded ranch located in one of Smithtown's most desirable neighborhoods. From the moment you step through the inviting entrance foyer, sunlight pours in through the skylight and soaring picture windows. This home blends comfort and style at every turn. The Eat in kitchen shines with granite countertops, updated appliances and a skylight. The formal living room dazzles with two floor-to-ceiling picture windows that frame the professionally landscaped grounds. A sunken den invites cozy evenings beside the wood-burning fireplace. Spacious primary suite, with brand-new full bath. Three additional bedrooms and 1.5 freshly updated bathrooms offer room for everyone. Stunning sun-soaked three-season room lends to more entertaining space. Step outside to your private resort-style yard where a saltwater in-ground pool with a new liner awaits. Perfect for summer days and unforgettable gatherings. Full finished basement offers endless possibilities—media room, game space, or extra entertaining area. The possibilities are endless. The full attic and 2-car garage provide ample storage. Multi car driveway. Updated high-efficiency Navien heating system ensures year-round peace of mind. New CAC System, 11 Zone IGS Genrator 200 Amp Elec. Ideally located near Blydenburgh County Park, Stonebridge Golf Course, shopping, and major highways, this exceptional home delivers the perfect balance of tranquility and convenience. Don't miss your chance to make it yours! Taxes w/o star exemption

39 Merrivale Drive, Smithtown

$1,675,000

4 Beds ⋅ 6 Baths ⋅ 1017188 MLS

Welcome to 3 Salt Hay Way, an exceptional custom-built residence where timeless architecture, refined craftsmanship, and resort-inspired living come together in one of Smithtown's most picturesque settings. This extraordinary estate offers a rare blend of privacy, elegance, and everyday luxury. Designed for both grand entertaining and comfortable living, this magnificent residence showcases elegant formal and informal dining areas, a welcoming sitting room, a den anchored by a wood-burning fireplace and custom bar, a private home office, and two beautifully finished lower levels featuring a custom home theater and expansive recreation space. At the heart of the home is a stunning chef's kitchen complemented by a separate prep kitchen, creating the perfect setting for effortless entertaining while keeping the main living spaces pristine. Completing the home are four spacious bedrooms, four full bathrooms, and two half bathrooms, anchored by a luxurious primary suite featuring a spa-inspired bath with a soaking tub, separate water closet, makeup vanity, and an impressive custom walk-in closet. Additional features include exquisite architectural millwork, high-end custom finishes, select smart home technology, a central vacuum system, custom closet systems throughout, a whole-house generator, abundant storage, and an attached two-car garage. The resort-style backyard is equally impressive. Professionally landscaped grounds showcase dramatic landscape lighting, a tranquil Zen garden, an outdoor fireplace, a fully equipped outdoor kitchen with a built-in grill, elegant water features, and a spectacular heated in-ground pool while creating an exceptional setting for entertaining or quiet relaxation. Offering an exceptional combination of luxury, craftsmanship, and thoughtful design, 3 Salt Hay Way is a residence that must be experienced to be fully appreciated.

3 Salt Hay Way, Smithtown

$739,000

3 Beds ⋅ 2 Baths ⋅ 1010094 MLS

Welcome home to this beautifully maintained ranch nestled on picturesque, park-like grounds in the highly sought-after Smithtown School District! Offering 3 bedrooms and 2 full baths, this home is currently configured as a spacious 2-bedroom, with the third bedroom being used as a dining room. It can easily be converted back to a third bedroom to suit your needs. The inviting living room features a warm wood burning fireplace, creating the perfect gathering space, while hardwood floors are tucked beneath the carpeting, ready to be revealed. Enjoy year-round comfort with central air conditioning. Updated windows and roof. The full finished basement offers an abundance of additional living space, ideal for a family room, home office, gym, recreation room, or guest area. A one-car garage w/ OSE provides added convenience and storage. Step outside to your own private oasis featuring beautifully landscaped, park-like grounds with IGS and a spacious deck overlooking the serene backyard perfect for entertaining, relaxing, or enjoying your morning coffee in a peaceful setting. Conveniently located near shopping, restaurants, parks, and major roadways, this home offers comfort, flexibility, and an exceptional lifestyle in the desirable Smithtown School District. Don’t miss this wonderful opportunity!

42 Summit Drive, Smithtown

$1,299,000

3 Beds ⋅ 4 Baths ⋅ 1010163 MLS

A rare opportunity to own this exceptional 3 bedroom, 4 bath Ranch situated on a beautifully landscaped property in the coveted Smithtown Pines neighborhood. Meticulously renovated throughout, this turnkey home showcases refined craftsmanship, spacious sun filled interiors, and an effortless flow designed for everyday living and elegant entertaining. The kitchen serves as the heart of the home and features quartz countertops, a center island, stainless steel appliances, and ample cabinetry, providing both style and functionality. Updated bathrooms throughout the home offer modern finishes and a clean, refreshed feel. The fully finished basement provides a versatile living space, ideal for recreation, media, home office, additional bedrooms, or extended guest accommodations. The spectacular outdoor setting is truly a standout feature. A heated free form in ground pool with a cascading waterfall is surrounded by lush landscaping, extensive landscape lighting, and multiple areas for relaxation and gathering. The impressive gazebo is equipped with a built in kitchen, TV and cozy fireplace, creating the perfect setting for entertaining guests or enjoying quiet evenings at home. Every detail has been thoughtfully designed to provide a private vacation like retreat right in your own backyard. Meticulously maintained and move-in ready, this exceptional property offers the perfect combination of sophisticated indoor living and unparalleled outdoor amenities in one of Smithtown's most desirable neighborhoods. Just unpack and start enjoying the lifestyle you deserve.

109 Shirley Court, Smithtown

$999,999

4 Beds ⋅ 3 Baths ⋅ 1017743 MLS

Nestled on a quiet cul-de-sac, this timeless Colonial offers the perfect blend of comfort, elegance, and privacy. Featuring 4 bedrooms and 2.5 baths, the home showcases warm wood flooring, abundant natural light, and a neutral palette throughout. he spacious kitchen is designed for both everyday living and entertaining, offering granite countertops, stainless steel appliances, ample prep space, and a tiered breakfast bar that keeps family and guests connected. Formal dining and living rooms each feature their own fireplace, creating inviting spaces for gatherings and quiet evenings alike. Outside, the private backyard is a true retreat. Backing directly onto parkland, the property enjoys exceptional privacy and features an inground pool surrounded by wrought iron fencing, beautiful paver patios, and multiple seating areas for relaxing or entertaining. Completing the package are a large garage, generous driveway parking, and storybook style curb appeal that makes a wonderful, lasting first impression.

14 Sandpiper Court, Smithtown

$800,000

3 Beds ⋅ 3 Baths ⋅ 1018369 MLS

Thoughtfully expanded in 2007, this beautifully maintained 3/4-bedroom, 2.5-bath home offers a spacious and versatile floor plan filled with abundant natural light and rich hardwood floors. Recent improvements include a brand-new roof, enhancing both value and peace of mind. The inviting kitchen features granite countertops, custom oak cabinetry with pull-out shelving, stainless steel appliances, a wall oven, cooktop, microwave, dishwasher, and a sun-filled bay window. The second level includes a spacious primary suite with a walk-in closet and private bath, two additional bedrooms, a full bath with a cast-iron tub, and a loft area that provides flexibility for a home office, sitting area, or potential fourth bedroom. The lower level features a comfortable den, half bath, utility area, and additional storage/workroom space. Outside, enjoy the fenced backyard with an impressive 18’ x 36’ in-ground pool and brick paver patios in both the front and back, creating an ideal setting for outdoor entertaining and everyday enjoyment. An oversized two-car garage provides ample room for vehicles, storage, hobbies, or workshop space. The property is located approximately .8 miles from St. Catherine of Siena Hospital. Combining generous living spaces, thoughtful updates, and exceptional indoor and outdoor amenities, this home offers a layout designed to accommodate a variety of lifestyles.

158 Saint Nicholas Avenue, Smithtown

$950,000

4 Beds ⋅ 3 Baths ⋅ 1017293 MLS

Welcome to this stunning high-end Splanch, where timeless elegance meets modern comfort. This beautifully appointed 4-bedroom, 2.5-bath residence showcases exceptional craftsmanship and designer finishes throughout. The spacious primary suite serves as a private retreat, featuring a luxurious en-suite bath with heated floor and walk in closet. Thoughtfully updated, the home offers a 5-year-old roof and a brand-new gas heating system, providing both peace of mind and energy efficiency. Every room reflects sophisticated style, with designer touches and attention to detail creating a warm yet refined atmosphere. The home's flowing layout is perfect for both everyday living and entertaining. Step outside to your own private country club oasis. The spectacular backyard features a sparkling saltwater pool surrounded by elegant travertine pavers, a safety fence, and lush professional landscaping that creates a serene, resort-like setting. Enjoy outdoor dining and relaxation on the spacious patio complete with a retractable awning, offering the perfect blend of sun and shade. This exceptional property combines luxury, comfort, and resort-style living in one remarkable package—a true must-see for the most discerning buyer.

22 Villa Lane, Smithtown

$825,000

4 Beds ⋅ 3 Baths ⋅ 1013533 MLS

Nestled on a quiet cul-de-sac, this beautifully constructed ranch welcomes you with a circular driveway, charming front porch, and inviting entrance foyer. Recently refreshed, the home features newly refinished hardwood floors throughout and fresh interior paint, creating a bright, airy atmosphere with exceptional functionality. The main level offers three spacious bedrooms, two full bathrooms, and abundant storage. The updated maple kitchen is designed for both everyday living and entertaining, featuring granite countertops, a center island, Wolf cooktop, double ovens, and a walk-in pantry. A convenient laundry room and direct access to the three-car garage add to the home's practicality. The open-concept layout seamlessly connects the kitchen to the living and dining areas, all overlooking the picturesque backyard. An open staircase leads to the lower ground level, where you'll find a comfortable den with a wood-burning fireplace, a private home office, bedroom, bathroom and extensive additional storage space. Step outside to your own private backyard oasis. Designed for entertaining, the property boasts an inground gunite pool with spa and Loop-Loc safety cover, a pergola set on low-maintenance Trex decking, and a gazebo providing covered outdoor living and gathering space. This exceptional Smithtown home combines quality construction, thoughtful updates, and mature landscaping that offers exceptional privacy in a highly desirable cul-de-sac location. Come see for yourself and fall in love!

15 Veronica Court, Smithtown

$950,000

4 Beds ⋅ 3 Baths ⋅ 1017406 MLS

Nestled on a sprawling and picturesque property in the heart of Smithtown, this whole house renovated in year 2022, 4-bedroom, 3-bathroom residence offers the perfect blend of privacy, space, and country-style living and very close the horse trails at Blydenburgh Park and minutes to Routes 347 & 454. Set on beautifully maintained grounds, the property features its own horse stable and equestrian facilities, making it an exceptional opportunity for horse enthusiasts, hobby farmers, or those seeking a peaceful retreat with endless possibilities. The charming home offers spacious living areas filled with natural light, generously sized bedrooms, and a flexible layout designed for comfortable everyday living. Outside, enjoy expansive open spaces, mature trees, and a tranquil setting rarely found on Long Island. A long private driveway provides ample parking and enhances the estate-like feel of the property. Whether you’re looking to enjoy horseback riding on your own property, simply embrace a lifestyle surrounded by nature, this one-of-a-kind Smithtown offering is not to be missed. Property Highlights: * 4 Bedrooms | 3 Full Bathrooms (2 bedroom 1 full bath on the first floor and 2 bedroom with 1 full bath located on the 2nd floor) * Recent updates: Oil Tank Replacement (2025) , Copper Pipes Installed (2026) * Private Horse Stable & Equestrian Facilities * Expansive Grounds with Open Space * Long Private Driveway with Ample Parking * High-end appliances (Wolf 36” six-burner range with pot filler, 42” paneled Sub-Zero refrigerator/freezer, Bosch ultra-quiet dishwasher, Sharp microwave drawer) * Conveniently Located Near the horse trails at Blydenburgh Park and minutes to Routes 347 & 454, easy access to Major Roadways.

45 Croft Lane, Smithtown

$789,000

4 Beds ⋅ 2 Baths ⋅ 1016434 MLS

Welcome to 50 Amsterdam Road, an inviting 4-bedroom home ideally situated in one of Smithtown's most desirable neighborhoods. Set on a generous lot, this residence offers comfortable living spaces, room to grow, and endless potential to make it your own. The private backyard provides a peaceful setting for relaxing, entertaining, and enjoying the outdoors, enhanced by architectural landscape lighting that creates a warm and inviting ambiance after sunset. A spacious finished lower level expands the home's versatility, offering multiple finished rooms that can easily adapt to your needs—whether you're seeking additional living space, room for extended family, guest space, a home office, or a recreation area. Located within the highly regarded Smithtown Central School District, homeowners benefit from access to a community known for its strong educational programs, beautiful parks, and exceptional quality of life. Beyond the property, enjoy all that Smithtown has to offer—from its charming downtown filled with local shops and restaurants to nearby recreational amenities, beaches, and convenient transportation options. Combining suburban tranquility with everyday convenience, 50 Amsterdam Road presents a wonderful opportunity to enjoy the warmth, character, and community spirit that make Smithtown one of Long Island's most sought-after places to call home.

50 Amsterdam Road, Smithtown

$879,000

4 Beds ⋅ 3 Baths ⋅ 1015936 MLS

Four Bedroom Two and Half Bath Brookfield Colonial with Two Car Attached Garage, Covered Front Porch, 16x32' Inground Pool & Paver Patio, with Fenced Rear Yard. Natural Gas Heat, 150 Amp Electric, Hardwood Floors, Tile & Wall-to-Wall Carpet. Step Down Rear Den with Woodburning Fireplace W/ Stove Insert. Updated Eat-in-Kitchen with Granite Tops & Stainless-Steel Appliances, Gas Cooktop. Formal Dining Room with Two Built-Ins & Hardwood Floors. Large Formal Living Room, Second Floor has Primary Bedroom with Two Closets, Makeup Area & Attached Updated En-Suite Bath. Updated Full Hall Bath & Three Bedrooms with Hardwood Floors. Belgian Block Lined Blacktop Driveway & Paver Front Walkway. Thru Wall AC Units. Inground Sprinklers, Shed & Gazebo are a Gift.

23 Hurtin Boulevard, Smithtown

$1,099,999

4 Beds ⋅ 3 Baths ⋅ 1014077 MLS

Welcome to this beautifully updated 4 bedroom, 2.5 bath Colonial, nestled at the end of quiet dead-end street in the desirable Town of Smithtown. From the moment you arrive, the newly paved circular driveway, manicured grounds, and exceptional curb appeal set the stage for what awaits inside. Step through the front door into a stunning open foyer where natural light and elegant design create an immediate sense of warmth and sophistication. Rich hardwood floors flow throughout the home, leading you into a custom designed kitchen featuring quartz countertops, glass tile flooring, abundant cabinetry, and thoughtful finishes that make both everyday living and entertaining a pleasure. A newly renovated powder room off the kitchen has direct access to the yard, perfect for guests enjoying the outdoor amenities. Convenience meets luxury with a spacious mudroom, pantry, and laundry room off the two car garage. A living room, family room with wood burning fireplace and formal dining room complete the layout of the first floor. Upstairs, skylights bathe the landing in natural light, creating a bright and welcoming second floor space. . Four generously sized bedrooms offer comfort and privacy, including a serene primary suite complete with an updated en-suite bath with heated floors, skylight, electric fireplace and two spacious closets. The fully finished basement provides exceptional additional living space and includes a cedar closet for storage and wet bar. Recent updates include a brand new tankless hot water heater, offering efficiency and peace of mind. Outside, prepare to be captivated by an exquisitely landscaped backyard designed for both relaxation and entertaining. Multi level grounds with charming gazebos, a built in heated pool, pool house, two storage sheds and a nine zone sprinkler system combine to create a resort like setting you will never want to leave. Whether hosting summer gatherings or enjoying a quiet evening under the stars, this outdoor oasis is truly unforgettable. A rare opportunity to own a meticulously and thoughtfully updated home in Smithtown.

17 Lower Road, 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

$950,000

4 Beds ⋅ 3 Baths ⋅ 1009532 MLS

Welcome to 19 Knoll Lane, Smithtown — Where Comfort Meets Elegance Nestled in the heart of Smithtown, this stunning 4-bedroom, 2.5-bath colonial is the home you've been waiting for. From the moment you step inside, you'll be captivated by the thoughtfully designed layout that perfectly balances everyday living with sophisticated entertaining. The spacious formal living room and formal dining room set the stage for memorable gatherings, while the warm and inviting den offers the perfect retreat for quiet evenings at home. The eat-in kitchen is ideal for casual meals and morning coffee alike. Rest easy knowing you're covered year-round with natural gas heat, central air conditioning, and a security system, ensuring comfort and peace of mind in every season. Step outside and discover your own private paradise. Unwind beneath the charming gazebo, host unforgettable evenings around the built-in fire pit, or simply soak in the tranquility of your beautifully appointed backyard. 19 Knoll Lane isn't just a house — it's the lifestyle you deserve. Don't miss your chance to call this exceptional property home!

19 Knoll Lane, Smithtown

$679,000

3 Beds ⋅ 2 Baths ⋅ 1012925 MLS

Welcome to this beautifully renovated 3-bedroom, 1.5-bath ranch nestled in Smithtown and located within the Hauppauge School District. This move-in-ready home features an open-concept layout and was extensively updated in 2024. The stunning new kitchen is equipped with JennAir appliances and a Frigidaire Professional refrigerator, while Anderson windows provide abundant natural light throughout. A versatile bonus room offers endless possibilities. Additional updates include gas conversion, dual heating options, natural gas heat, and an energy-efficient heat pump system. A new roof with solar panels, and a partially finished basement that provides additional living, recreation, or storage space. The cesspool is approximately 5 years young. Conveniently located near shopping, restaurants, parks, transportation, and all that Smithtown has to offer, this home combines modern updates, energy efficiency, and everyday convenience in one exceptional package. Don’t miss the opportunity to make this turnkey home your own. Low Taxes!!! With star exemption: $10,567

39 Tanglewood 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

$899,000

3 Beds ⋅ 3 Baths ⋅ 1012301 MLS

Location, Location and Location ! One of the Most Wanted Addresses in Smithtown with Hauppauge Schools plus Forest Brook Elementary. Nice Center Hall Ranch with Wood Floors Everywhere, Granite Eat in Kitchen with SS Appliances, Lots of Natural Light from Skylights, Arch Roof, Cold Central Air, Hi-Hats, Family Room with Wood Burning Fireplace, Formal Dining Room with Picture Molding, Primary Bedroom w/ Bath plus 2 More Bedrooms All on 1 Floor, Laundry on 1st Floor, 2 Car Garage, In Ground Sprinklers for your Professional Landscaping, Fenced Yard Right on the Golf Course with In Ground Pool ( 16x32) Loop Loc Cover, Wood Decking, Composite Raised deck, Updated Force Oil Burner plus Oil Fired Hot Water, Full Basement with 2 Office(bedrooms)Spaces, Huge Playroom, Lots of Storage, These Opportunities Don't Come Up Often, make an Appointment Today !

34 Aberdeen Road, 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

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