Smithtown NY 5 Bedroom Real Estate, Homes, Condos for Sale

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

$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

$799,999

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.

39 Sheryl Crescent, Smithtown

$900,000

5 Beds ⋅ 3 Baths ⋅ 1016495 MLS

Tucked away on a quiet dead-end street just moments from the heart of Smithtown, this expanded Hi Ranch offers the space, flexibility, and location today’s buyers are searching for. With a thoughtfully designed den-side extension featuring vaulted ceilings (added in 1999), the home opens up beautifully to create a bright, airy living space that stands apart from typical layouts. With 5 bedrooms and 3 full baths, the home is ideally suited for mother/daughter living or extended family. The layout provides natural separation while still feeling cohesive—perfect for multi-generational households or anyone looking for versatile living options without compromise. Major updates bring true peace of mind, including a young roof (2016) and boiler (2021) and Andersen windows throughout, offering energy efficiency and long-term value. Outside, enjoy a fully fenced yard with ornamental aluminum fencing and manicured, low-maintenance landscaping—ideal for relaxing or entertaining without the upkeep. Located just a half mile from Smithtown’s vibrant Main Street and only one mile to the LIRR, this home combines suburban privacy with everyday convenience, making commuting, dining, and shopping effortless. A rare opportunity to own a spacious, adaptable home in a prime Smithtown location—designed to grow with your lifestyle. Smithtown Schools. True Taxes 15,851 before exemptions.

4 Long Hill Road, Smithtown

$1,099,999

5 Beds ⋅ 4 Baths ⋅ 1005651 MLS

Welcome to 54 Sandy Hollow, a beautifully maintained Brookfield Colonial located within the highly regarded Commack School District. This spacious home offers 5 bedrooms and 3.5 baths, featuring an open and versatile floor plan designed for both everyday living and entertaining. The heart of the home is the impressive kitchen, complete with a large eat-in area, expansive granite island, abundant cabinetry, and soaring ceilings that create a bright and inviting atmosphere. The flexible layout includes two primary suites—one conveniently located on the main level and another on the second floor—providing excellent options for extended living arrangements or guest accommodations. A partially finished basement offers additional living space, storage, and endless possibilities to suit your needs. The attached two-car garage adds convenience and functionality. Step outside to your own private backyard retreat, featuring a heated gunite in-ground swimming pool, generous outdoor living space, and mature landscaping that provides exceptional privacy. Perfect for relaxation or entertaining, this backyard oasis offers the comfort and tranquility you have been searching for. Conveniently located near shopping, dining, parks, and major transportation routes, this is a wonderful opportunity to enjoy all that Commack has to offer. Natural gas service and a whole-house generator provide efficiency, reliability, and peace of mind

54 Sandy Hollow Drive, Smithtown

$799,000

5 Beds ⋅ 2 Baths ⋅ 1002706 MLS

Welcome to this beautifully maintained move in ready Hi-ranch, nestled in the desirable Sherbrooke Drive section of Smithtown. This home offers 2800 sq. ft. of living space with 11 rooms and exceptional versatility. RARE BONUS: Legal Garage Conversion to a gorgeous suite that includes a bedroom, living room, walk in closet, bathroom, summer kitchen & two separate entrances! In addition, new separate ductless AC/heating unit for the suite. Just think of the possibilities you can utilize this addition for. The main level of this home offers huge kitchen with chef's Garland oven, full dining room, sun drenched living room, 3 bedrooms and bathroom, with hard wood oak under all carpeting. The lower level boasts a massive den with a working, wood burning, brick fireplace & additional room with a large closet (office/bedroom) Backyard has an exceptionally expansive deck with details such as built in benches and more. Large attic with easy access provides additional storage space. Must see this exceptional home to truly appreciate.

4 Sherbrooke Drive, Smithtown

$1,185,000

5 Beds ⋅ 3 Baths ⋅ 1010498 MLS

Welcome to your private retreat, where comfort, space, and timeless charm come together! Set on a beautifully landscaped .71 acre property, this spacious 5 bedroom, 2.5 bath home in the heart of Smithtown, nestled in the beautiful Forestwood section, offers the perfect blend of elegance, functionality, and outdoor living. Featuring gleaming hardwood floors throughout and a thoughtfully designed layout ideal for both everyday living and entertaining. The heart of the home is the beautiful eat-in-kitchen, featuring granite countertops, tons of cabinetry, and plenty of room for casual meals and conversation. For larger gatherings, the formal dining room provides a warm and inviting setting for holidays and special occasions. Relax in the spacious living room, unwind by the wood-burning fireplace in the cozy den, or enjoy movie nights and game days in the separate oversized family room. With five generously sized bedrooms, there’s plenty of space for family, guests, or a home office. Step outside and discover your own backyard oasis. Multiple decks extend the living space outdoors, creating the perfect setting for barbecues, celebrations, or quiet evenings under the stars. The inground freshwater pool invites you to enjoy summer days in style, while the lush gardens, colorful flowers, and mature plantings add beauty and tranquility year round. An amazing standout feature is the large 2 car barn in the backyard, ideal for hobbyists, gardeners, workshop space, extra storage, or parking additional vehicles. This incredible property offers the rare combination of indoor comfort, outdoor enjoyment, and versatile space, all in a setting that feels both welcoming and private. IGS, CAC, 150 Amps

28 Cygnet Drive, Smithtown

$1,600,000

5 Beds ⋅ 3 Baths ⋅ 1010315 MLS

If you appreciate the privacy and security of a gated community, this exceptional home is not to be missed. Built in 2006 and extensively upgraded over the past 13 years, this stunning residence offers approximately 3,600 square feet of beautifully designed living space with 5 bedrooms and 3 full baths. A grand two-story entry foyer welcomes you into a home filled with architectural elegance, including cathedral-vaulted ceilings, tray ceilings, custom moldings, and gleaming hardwood floors throughout. The spacious formal living and dining rooms are ideal for entertaining, while the spectacular chef’s kitchen features a large center island, granite countertops, stainless steel appliances, and a premium Wolf range. The main level includes a versatile guest bedroom or home office, while the expansive lower level provides additional living space with direct access to the backyard. Head upstairs to the luxurious primary suite, featuring two spacious closets and a beautifully appointed primary bath designed for comfort and relaxation. Down the hall, you'll find three additional generously sized bedrooms and a full hall bath, providing ample space for family and guests. Step outside to your own private resort-style retreat. Mature landscaping enhanced with professional lighting surrounds an 18' x 36' heated saltwater freeform pool. Cambridge patios and walkways, an outdoor kitchen, and thoughtfully designed outdoor living spaces create the perfect setting for relaxation and entertaining. Community amenities include pickleball, tennis, basketball courts, and a sport court. The HOA fee is $175 per month, paid quarterly, and covers maintenance of the gated entrance, street lighting, and community recreational facilities. This is a rare opportunity to own a dream home in one of Smithtown’s most desirable gated communities. Luxury, privacy and resort style living await you at 25 YellowTop Lane. Outside kitchen as-is.

25 Yellow Top Lane, Smithtown

$1,656,000

5 Beds ⋅ 3 Baths ⋅ 1010107 MLS

Nestled at the end of a private long drive shared with only 2 other homes and Not directly on Landing, this magnificent custom brick home offering Luxurious living space on a private 1.2 acre setting. features include a dramatic two-story grand entry foyer with two staircases, soaring vaulted ceilings, gourmet chef's kitchen with cherry cabinetry, granite countertops and Viking appliances, especially including Sub-Zero refrigerator, hardwood floors throughout entire house. Master suite with radiant heated floors, spa-inspired primary suite, and beautiful views of preserved land, Designed for elegant entertaining and comfortable living with vaulted veiling and extra-large windows. Three high ceiling attached car garage with potential for double car lift storage. The full basement features high ceilings and a separate outside entrance, offering excellent potential for recreation, home office, gym, workshop or future finished living space. This exceptional residence combines timeless architecture, privacy. quite and premium craftsmanship.

589 Landing Avenue, Smithtown

$1,499,999

5 Beds ⋅ 4 Baths ⋅ 1005485 MLS

Welcome to 48 River Heights Drive where a tree lined street meets a true custom masterpiece in beautiful North Smithtown. This luxurious 4,800 sq ft home offers 5 bedrooms, 4 baths, a private office, and an incredible blend of high-end design, comfort, and functionality. Custom built, expanded, and fully renovated by the current owner, this home features Brazilian cherry and hardwood oak floors, Pella windows and doors, crown molding, a 400 amp electric service, 4-zone HVAC, central vacuum, full security system, indoor/outdoor Sonos audio, and smart wiring throughout. The heart of the home is the impressive 27x27 chef’s eat-in kitchen with custom cherry cabinetry, granite countertops, natural stone backsplash, a massive 13x5 granite island, high-end appliances, 2 dishwashers, 2 sinks, double ovens, and a butler’s pantry with additional refrigerator/freezer, sink, storage, and heated floors. The kitchen flows into a palatial 40x20 great room with a natural gas fireplace, built-ins, oversized sliders, and beautiful views of the backyard oasis. The 900 sq ft primary suite is a true retreat with soaring 13 ft ceilings, a spa-like bath, oversized shower, jacuzzi tub, double granite vanities, and a custom walk-in closet. Additional highlights include a second-floor dream laundry room with 2 washers, 2 gas dryers, granite folding counters, a custom office, spacious bedrooms, custom baths, and a newly finished basement completed in 2025. Set on a flat and private .52-acre property, the backyard is an entertainer’s dream with an in-ground pool, brand-new liner, granite coping, Italian porcelain pavers, sitting wall, gas fire pit, architectural columns, lighting, and beautiful outdoor living space. Located in the Smithtown Central School District and close to beaches, parks, golf, marinas, restaurants, and shops, this turnkey home offers luxury living inside and out.

48 River Heights Drive, Smithtown

$849,999

5 Beds ⋅ 2 Baths ⋅ 1004941 MLS

Welcome to 74A Hilltop, a beautifully maintained home offering the perfect blend of space, flexibility, and outdoor living in the heart of Smithtown. Surrounded by mature landscaping and natural privacy, this property was designed for the way today’s buyers want to live. The spacious layout offers multiple living areas ideal for multi-generational living, extended family, guests, or remote work flexibility. The lower-level living space with a summer kitchen provides seamless access to the backyard, creating an effortless indoor-outdoor flow perfect for entertaining. Step outside to your own private backyard retreat featuring expansive decking, pool area, patio space, fire pit area, and sprawling fenced property perfect for summer gatherings, outdoor dining, and everyday relaxation. Inside, you’ll find sun-filled rooms, hardwood flooring, oversized windows, updated baths, spacious bedrooms, and a large eat-in kitchen with abundant cabinetry and workspace. Located within the highly regarded Smithtown School District and close to parks, shopping, restaurants, major roadways, and the LIRR, 74A Hilltop offers the privacy, functionality, and lifestyle buyers are actively searching for on Long Island.

74A Hilltop Drive Unit #A, Smithtown

$779,999

5 Beds ⋅ 3 Baths ⋅ 982923 MLS

Incredible opportunity to own a newer, oversized high ranch offering five bedrooms, three full bathrooms, and a flexible layout ideal for multigenerational living, or those who love to entertain, all set on a flat, oversized corner lot with outstanding curb appeal and modern functionality. The property features a blacktop driveway with a Belgium block border, a paver front entry, and a fully fenced yard with a spacious paving stone patio perfect for gatherings, along with vinyl siding and in-ground sprinklers for easy maintenance. Upstairs, a dramatic formal living room boasts soaring vaulted ceilings, oversized windows that flood the space with natural light, a ceiling fan, and a custom handcrafted built-in wall unit with bookshelves, cabinetry, and a television center, flowing seamlessly into a formal dining room with continued vaulted ceilings, crown molding, custom trim, decorative entry accents, and a sliding glass door leading to a private rear deck for effortless indoor-outdoor living. The chef’s kitchen offers white cabinetry, granite countertops, a tile backsplash, stainless steel appliances, abundant storage and workspace, and a large center island highlighted by a chandelier and detailed wainscoting. The upper level includes three spacious bedrooms, including a primary suite with its own full bathroom featuring a tub and glass-enclosed shower, while the additional bedrooms share a well-maintained hall bathroom. The first level provides exceptional versatility with high ceilings and a private entrance leading to a large den or family room, along with a spacious bedroom with its own entrance, an additional oversized bedroom, a bonus room ideal for a home office or recreation space, a full bathroom with a glass-enclosed shower, and a dedicated laundry/mudroom. Additional features include gas heat, a 200-amp electrical panel, and second-floor central air conditioning that is only three years young, making this exceptional home a perfect blend of space, comfort, and versatility.

4 Jerome Street, Smithtown

$749,000

5 Beds ⋅ 2 Baths ⋅ 956909 MLS

Great Hi Ranch with 2 Sep Living Areas plus Garage, Fenced Yard, Oversize Driveway, Smithtown Schools, Central Air

106 Summit Drive, Smithtown

$1,099,988

5 Beds ⋅ 4 Baths ⋅ 991887 MLS

Welcome to this stunning custom residence in the highly sought-after Smithtown Pines community. Set on an expansive property, this one-of-a-kind colonial home showcases a distinctive interior design paired with high-end finishes, making it truly stand out from the rest. The main level features soaring 17-foot cathedral ceilings, oversized windows that flood the home with natural light, a grand entryway, and an open-concept living room centered around a striking stone fireplace. Beautiful parquet hardwood flooring flows throughout the home, complemented by updated porcelain tile bathrooms and numerous additional upgrades. Truly Exceptional is the outside entry to a very spacious living area, where you can provide a 1 or 2 bedroom living area that requires very little steps. In addition to that is the third car, extremely spacious garage, ideal for car enthusiast or create your own art, ceramic or whatever your heart desires studio. The upper level offers a well-appointed kitchen with custom cabinetry and granite countertops, a formal dining room overlooking the main living area, and an additional living space that provides flexibility for today's lifestyle with more versatility with Bedrooms, full bathrooms, and a third living area, making it ideal for extended family, guests, or recreation space. In total, the home features 5 spacious bedrooms and 4 full bathrooms. Step outside to a spacious wood deck, perfect for entertaining while enjoying the privacy of the backyard. Additional highlights include an approximately 1,400-square-foot 3-car attached garage, 2-zone central air conditioning, 200-amp electrical service, and a roof that is approximately 3 years old. this remarkable property presents a rare opportunity to own a truly unique home in Smithtown Pines.

23 Colonial Drive, Smithtown

$945,000

5 Beds ⋅ 3 Baths ⋅ 987129 MLS

Location, Location, Location!!! This classic, VERY spacious and well maintained farm ranch home has loads of character and charm with hardwood floors throughout. 5-bedrooms, 3 full -baths and 2 car garage set on a picturesque, quite, tree lined and manicured street. This lovely and traditional home blends timeless elegance with thoughtful updates and TONS of storage. Some recent improvements include a new roof and upgraded pool equipment (pump, heater, and filter) some Anderson windows, a fully fenced yard for added privacy, and a beautiful mahogany deck overlooking the in-ground heated pool—perfect for relaxing or entertaining. Located within the highly regarded Smithtown School District, this property offers both charm and modern convenience in a desirable setting and close to all that Smithtown has to offer ......nature and hiking trails galore, incredible restaurants, coffee shops, boutiques and close to LIRR.

45 Woodland Drive, Smithtown

$725,000

5 Beds ⋅ 3 Baths ⋅ 984398 MLS

Welcome to 20 Veronica Court, Smithtown — a spacious ranch-style home nestled on a quiet cul-de-sac in a desirable residential setting. This 5-bedroom, 3-bathroom ranch offers comfortable single-level living with additional space to grow. The primary bedroom features a private en-suite bathroom and direct access to its own secluded deck — the perfect spot to enjoy your morning coffee or unwind in the evening. The home also boasts a second deck off the kitchen, ideal for outdoor dining and entertaining in the backyard. A full basement expands the home’s versatility, complete with an additional bedroom and bathroom, providing excellent potential for extended living space, guests, or recreational use. The property offers solid bones and a functional layout, while presenting a great opportunity for buyers to add their personal touches and updates to make it truly their own. Located on a peaceful cul-de-sac, this home combines privacy, convenience, and potential — all within close proximity to shopping, dining, parks, and major roadways.

20 Veronica Court, Smithtown

$1,200,000

5 Beds ⋅ 5 Baths ⋅ 977996 MLS

Nestled in the highly desirable Smithtown Pines, this one-of-a-kind home offers a unique layout that's perfect for multigenerational living or for those seeking a spacious, versatile design. With five bedrooms and 4.5 baths, including two primary ensuites, this home offers exceptional accommodations - it's like getting two houses in one! The main home features a large living room that leads to an open dining room and eat-in kitchen. The kitchen is equipped with a center island and Silestone countertops, offering both functionality and style. Just a few steps up, the oversized primary ensuite (15'1" x 30'11") awaits, complete with a full bathroom and the convenience of an in-suite washer and dryer. You will also find two additional bedrooms with a full hall bathroom. The secondary living space area boasts an open floor plan, which includes a cozy living room with a fireplace, dining room, summer kitchen, separate laundry area, and full bathroom. Upstairs, two bedrooms provide private retreats, one with its own ensuite bathroom and dual closets. Set on a private 0.53-acre lot, the backyard is perfect for entertaining. It features a paver patio, an expansive deck with a screened gazebo, and an inviting inground pool. Plus, the property backs the local Park, ensuring complete privacy in a serene setting. Enjoy proximity to Blydenburgh Park and the Town of Smithtown beaches, where outdoor recreation is just moments away. 99 Shirley Ct presents a rare opportunity in the Pines- a perfect blend of elegance, functionality, and tranquility. Whether you need two separate living areas or one large home, this house can accommodate. Don't miss this thoughtfully crafted, one-of-a-kind home!,

99 Shirley Court, Smithtown

$1,250,000

5 Beds ⋅ 4 Baths ⋅ 975603 MLS

Welcome to this stately and impressive Colonial, ideally situated in one of Smithtown's most sought after and picturesque neighborhoods. This exceptional property offers a rare opportunity to create a custom luxury home in a truly premier setting. Boasting generous living space the home features a traditional and functional layout with a spacious Living Room, Dining Room, and inviting Den-perfect for everyday living and entertaining. The Kitchen with its Brazilian granite countertops offers generous space and serves as the perfect canvas to design the heart of your dream home. A beautiful feature of the home is a 280 ft expansive SunRoom extension, complete with hot tub, providing a unique space to unwind and relax all year long while overlooking the yard. Upstairs are 5 well appointed bedrooms including the Primary Bedroom with a huge ensuite full bathroom as well as an additional 1/2 bath. The backyard features a newly renovated 20x40 inground pool with new liner and all new coping (1 year old), and approx 3 year old filter, trex decking for low maintenance outdoor living, a beautiful pavillion to entertain under, and a gazebo. A 2 car garage, a young roof, an above ground 550 gallon oil tank, a 4 zone in-ground sprinklers, a tranquil rock waterfall, lightning rods and an expansive stone wall all around the front of the property. With its grand scale, coveted Smithtown location and proximity to the water, this is a rare find for someone to create a truly exceptional home in a prestigious neighborhood.

2 Three Pond Road, Smithtown

$1,249,000

5 Beds ⋅ 5 Baths ⋅ 969109 MLS

Original owner, clean and well maintained 4000 square foot colonial on 1.2 acres in Point of Woods Section. Featuring 5 beds/4 baths including an ensuite bedroom with full bath on the first floor (see floor plan). Double height entry foyer with large open living spaces. Huge kitchen, dining and family room with wood burning fireplace. Full basement with outside entrance. Two car garage with long driveway for several cars. Move in as it is or renovate to your style and taste. Available for immediate occupancy.

144 Landing Meadow Road, Smithtown

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