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2 Three Pond Road, Smithtown
$1,149,999
4 Beds ⋅ 3 Baths ⋅ 1059779 MLS
Welcome to 2 Three Pond Road.... This Yablonski built Center Hall Colonial is set on 1 Acre of Beautiful Property, located in the "Prestigious Grange Estates" of North Smithtown! Step inside to your grand entry foyer, formal dining room, EIK w/ top-of-the-line Imported Brazilian Stone Granite counter tops, double oven and updated SS appliances, Formal Living room w/ dual sided wood burning fireplace flowing seamlessly into the expansive den, bath powder room, and custom-built sun room w/ exquisite stone walls and built-in hot tub for tranquil relaxation, along w/ easy interior access to your 2 car attached side entry garage... upstairs you have your primary bedroom w/ private bidet and toilet room with separate shower/spa jacuzzi room, 3 additional generously sized bedrooms, Office space and/or 5th bedroom (or WIC potential), and additional full hall bathroom. Step outside to your private resort like back yard w/ mature privacy trees and professionally designed landscaping surrounding, a resort style IG pool w/ a gradual sloped bottom, custom-built pavilion area, gazebo, oversized Trex deck and tranquil waterfall.... creating the perfect setting for peaceful evenings and ultimate relaxation. Additional features include the following…. In Ground 20x40 Pool (Liner 2025) w/ a solar assisted heating system, CAC (1 Zone – 2018), Oil Heat (1 zone), Single Layer 30-year architectural Roof (2018), Hardwood floors throughout, 200 AMP electric, expansive paver driveway beautifully appointed to the side entry 2-car garage… all this and so much more set on a picturesque acre private corner lot w/ exquisite bluestone walling surrounding, cascading Waterfalls and fountains, lush nature and tranquility, you do not want to miss this!

2 Three Pond Road, Smithtown
28 S Lot Road, Smithtown
$1,189,000
4 Beds ⋅ 4 Baths ⋅ 1053324 MLS
Welcome to this grand, stately Colonial, beautifully landscaped and set on a private, fenced-in 1/2-acre lot. The property offers an exceptional setting for entertaining and enjoying the outdoors, complete with a gunite pool, charming gazebo, house generator, and two-car garage for added convenience and peace of mind. Inside, the home offers four bedrooms, three full bathrooms, one-half bathroom, a versatile den that can also be used as a home office, and two fireplaces. Beautiful hardwood floors extend throughout the main level, adding warmth and timeless elegance. A spacious formal living room and dining room provide an ideal setting for both everyday living and entertaining. The formal living room features a wood-burning fireplace, creating a warm and inviting atmosphere. The thoughtfully expanded kitchen offers an open and welcoming space for cooking, gathering, and enjoying time with guests, complemented by a beautiful gas fireplace that adds warmth and ambiance. The finished basement provides additional versatile space, along with a private outside entrance and bathroom. Step outside to enjoy a beautifully landscaped retreat designed for relaxation and summer entertaining. The expansive fenced-in grounds provide plenty of space to unwind, gather with guests, and create lasting memories. With its generous floor plan, elegant details, versatile finished space, two-car garage, and exceptional setting, this remarkable Colonial offers comfort, character, and an ideal blend of indoor and outdoor living.

28 S Lot Road, Smithtown
100 Edgewood Avenue, Smithtown
$1,199,999
5 Beds ⋅ 5 Baths ⋅ 1044455 MLS
Two distinct living spaces, one extraordinary property! Tucked down a long, private driveway off of Carrie Court, this home offers 4,198 square feet of living space in the Smithtown School District. The spacious main home and attached second living area each have a separate entrance and driveway, providing generous parking and a flexible layout. Real wood cedar siding, mature landscaping, raised stone flower beds, and custom wood entry details make a memorable first impression. Inside the main home, hardwood floors, crown and door molding, recessed lighting, and skylights set the tone. The formal living room features soaring vaulted ceilings and a dramatic three-sided stone wood-burning fireplace. The chef’s kitchen pairs deep espresso-toned Shaker cabinetry with white upper cabinets, glass-front accents, granite countertops, under-cabinet lighting, stainless steel appliances, a Viking gas cooktop, double ovens, dishwasher, built-in microwave, oversized stainless steel double sink, separate vegetable sink, garbage disposal, breakfast bar, and tile backsplash. It opens to an expansive dining room with vaulted ceilings, upper windows, a wall of windows overlooking the backyard, and French doors leading outside. Plantation shutters grace many of the first-floor windows. First floor also features a spacious den/great room, featuring recessed lighting, beautiful wood floors and custom molding. Upstairs, the primary suite occupies its own level, with bamboo flooring, custom shoji-style closets, a translucent screen wall, and a spa-inspired bath featuring radiant-heated floors, a Jacuzzi soaking tub, and an oversized glass-enclosed shower. A loft with vintage oak flooring, vaulted ceilings, and recessed lighting offers flexible space that could serve as an additional bedroom or home office. Two more bedrooms and a full bath with dual glass vessel sinks complete the upper level. The main home’s at-grade lower level has its own entrance, full bath with a glass-enclosed shower, recessed lighting, and box molding. The attached second living area has a separate entrance, oak flooring, crown molding, recessed lighting, a powder room, and a stunning kitchen with double-height ceilings and clerestory windows. Antique-glazed cream custom cabinetry, Viking gas cooktop, double ovens, farmhouse sink, granite countertops, floor-to-ceiling pantry storage, and a sage-green island with carved corbels make this space exceptional. Its primary suite features vaulted ceilings and a beautifully finished bath with Carrara-style marble, a walk-in shower, built-in seat, and custom vanity. Outside, discover a resort-style backyard with a freeform in-ground pool, Trex decking, estate fencing, outdoor shower, slate and paver patios, and multiple spaces to gather or unwind. Additional features include three-zone heating and air conditioning, a gas-powered Generac whole-house generator, a 300-amp electrical panel, and 13-zone in-ground sprinklers. Town of Smithtown records identify the property as a one-family dwelling with a special exception for separate living quarters. The exception does not transfer to a new owner; a buyer would need to reapply with the Town.

100 Edgewood Avenue, Smithtown
9 Mulberry Drive, Smithtown
$849,000
4 Beds ⋅ 2 Baths ⋅ 1051155 MLS
Welcome to this beautifully maintained 4-bedroom, 2-bath hi-ranch in Royal Oaks, Smithtown, offering comfortable living, flexible space, and an impressive backyard retreat. A charming front sunroom welcomes you inside, while the second sunroom features a natural gas fireplace and French doors leading to the upper deck overlooking the backyard. The home offers two full kitchens with appliances included, along with a lower level featuring a one-bedroom apartment. The home is a legal mother-daughter, with the required permits included with the property, offering added flexibility for its next owner. The recently renovated upstairs bathroom features ambient flooring, a heated towel rack, and a jacuzzi bathtub, adding comfort and convenience to the space. Step outside to enjoy a heated, gas-heated saltwater in-ground pool, hot tub, cedar sauna, gazebo, mature landscaping, and in-ground sprinklers. The property also features a full surveillance system for added peace of mind. Additional updates include newly insulated exterior walls and attic, a whole-house water filtration system, and a brand-new cesspool. Thoughtfully maintained and offering a versatile layout with extensive indoor and outdoor amenities, this Smithtown home is ready for its next owner. Come see everything it has to offer and schedule your private tour today!

9 Mulberry Drive, Smithtown
546 Long Beach Road, Nissequogue
$12,000,000
1034543 MLS
Rare and unparalleled opportunity to build your ultimate compound. Boasting 16.8 acres with 2000 feet of direct waterfront along the Long Island Sound in the exclusive, incorporated Village of Nissequogue. This sprawling legacy estate offers a rare combination of absolute privacy and endless coastal possibilities. Enjoy unparalleled, direct beach access via a staircase, allowing you to step off your estate and directly onto the sand to launch a kayak, paddleboard, or stroll the shoreline at sunset. Meandering trails, mature specimen trees, and stone paths complete this magnificent blank canvas. The expansive 11,000+ sq. ft. foundational footprint provides the perfect bones to recreate a world-class, 6-bedroom, 7-bathroom modern masterpiece, complete with structural footprints for both an all-season indoor pool and a sweeping outdoor pool oasis. A stone pathway leads you to the tennis court that is ready to be restored. Located in The Village of Nissequogue, Long Island’s best-kept luxury secret where unparalleled privacy meets pristine coastal living. This incorporated sanctuary offers a tranquil, estate-driven refuge just 50 miles outside Manhattan. Surrounded by StonyBrook Harbor, and the Long Island Sound. Residents also enjoy exclusive access to restricted shorelines like Short Beach and Long Beach, as well as the protected trails of the 150-acre David Weld Sanctuary.

546 Long Beach Road, Nissequogue
708 W Cabot Court Unit #708, Saint James
$499,998
1 Beds ⋅ 1 Baths ⋅ 1034423 MLS
55+gated community of Fairfield at Saint James. The brand new update ranch home offers one car garage, a special primary bedroom with walk in closet and eat in updated kitchen with large window. New appliances only one year new. The club house offers two outdoor pools, a fitness center, an indoor pool, library and much more....

708 W Cabot Court Unit #708, Saint James
57 Brooksite Drive, Smithtown
$959,000
4 Beds ⋅ 3 Baths ⋅ 1020597 MLS
LISTENING TO OFFERS! 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
10 Burham Drive, 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, a large guest suite (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
14 Sandpiper Court, Smithtown
$989,999
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
45 Croft Lane, 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
589 Landing Avenue, Smithtown
$1,626,000
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
2 Vistas Circle, Smithtown
$1,499,000
4 Beds ⋅ 4 Baths ⋅ LP1439480 MLS
Serene Location! To Be Built. Please Note That Rendering/Photo Shown Conveys Craftsmanship of Homes Previously Built. Taxes Are Not Known At This Time. Features Include Hardwood Floors, Granite Kitchen Countertops, Choice Of Cabinets With Dove-Tail Draws & Soft Touch Close, 2 Zone Central Air Conditioning, Colonial Base Moldings & So Much More. Some Optional Features Include Venting Out For Stove, A Fireplace, Tray Ceiling Primary Suite, Shadow-box Molding-- Builder Will Build To Suit- Close Distance To Long Island Railroad, Highways, Shopping And More. No Models Available To View~ Purchaser To Pay Customary Builders Fees. Prices Are Subject To Change-, Additional information: Appearance:Tbb,Separate Hotwater Heater:Y

2 Vistas Circle, Smithtown

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

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