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$997,999
5 Beds 4 Baths 1045526 MLS
Exceptional Extra-Large, Charming Home with Resort-Style Backyard & Incredible Flexible Living Space...This is a WOW House with lots of character!!! Welcome to this truly special DIAMOND Cape-style, well maintained home, set on beautiful half-acre grounds and offering an impressive blend of quality craftsmanship, modern updates, and exceptional versatility; Quality details continue throughout this home with solid interior doors, hardwood floors in most of home, recessed lighting, and Sonos speakers on the first floor, custom blinds, "50 year roof", clapboard siding with maintenance free shingles, updated electric. This home offers much more than meets the eye, it offers multiple stunning living spaces with an oversized two-car garage, and an incredible backyard retreat ! The MAIN section of this large home features four bedrooms, 2 1/2 baths, and a finished basement with adorable summer kitchen, outside entrance and egress window creating wonderful flexibility for guests, recreation, hobbies, or extended living needs! Adding even more versatility is an ADDITIONAL living area on the main floor featuring another large eat-in kitchen, living room, full bathroom, office, and additional bedroom. Whether used for extended family, guests, a private workspace, or simply additional everyday living space, the possibilities here are endless. The beautifully updated main kitchen is a true highlight, featuring luxurious quartzite countertops, Thermador double ovens, and Bosch appliances overlooking a family room/den with built in shelving and hardwood floors. On the 2nd floor, the primary suite is complemented by a custom-designed closet offering exceptional organization and storage. There are 3 additional bedrooms with skylights and gorgeous full bathroom with mosaic tiles, built-in area in shower and multiple shower heads. Step outside and discover your own private backyard oasis. The custom built salt water, heated in-ground pool features a concrete wall, sun deck, built-in bench seating, and deck jets, creating a resort-like setting for summer entertaining and relaxation. Another feature here is the beautifully built deck providing additional outdoor living space, while the custom outdoor shower is perfect after a swim or simply enjoying the outdoors. The expansive half-acre property also features in-ground sprinklers and a custom shed with chicken run, adding charm and function to the beautifully maintained grounds.

351 Forest Lane, Smithtown

$905,000
4 Beds 3 Baths 1032833 MLS
Pristine and sophisticated, this beautifully customized 4-bedroom, 2.5-bath ranch offers a spectacular open-concept design perfect for today's lifestyle. Originally built in the 1960s, the home has been thoughtfully updated over the years to reflect timeless elegance and exceptional craftsmanship. The stunning center island kitchen features a dramatic 7-foot black granite island, Sub-Zero refrigerator, Bosch dishwasher, GE appliances, under-counter microwave, and cooktop. Hardwood floors and custom built-ins enhance the home's warmth and character, while the spacious living and entertaining areas flow seamlessly to the rear deck for effortless indoor-outdoor living. A truly special home that is impeccably maintained and a must see.

22 S Lot Road, Smithtown

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$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

$989,000
3 Beds 3 Baths 1003638 MLS
Welcome to this beautifully maintained, sprawling ranch nestled on a spectacular country club property at the end of a cul-de-sac. Designed for seamless modern living, this sun-drenched home features 3 spacious bedrooms, 3 full baths, and an effortless, flowing layout. The main level boasts a bright, inviting living room, a formal dining room, and a classic tile kitchen. Unwind in the cozy den, anchored by a charming wood-burning fireplace equipped with a brand-new chimney insert (2025). The Ultimate Primary Retreat, this luxurious primary suite serves as your own private sanctuary, highlighted by a dramatic atrium addition. Featuring floor-to-ceiling windows, this breathtaking space offers panoramic views of the magnificent backyard. Step outside into a vacation-at-home paradise, complete with meticulously landscaped grounds, a sparkling in-ground pool, a serene koi pond, and a tranquil, cascading waterfall. Roof & Structure (2025): Brand-new roof, upgraded insulation, floorboards, and 4 stunning, light-flooding skylights. Finished Basement (2024–2025): Fully finished lower level maximizing your entertaining and living space, complete with a commercial-grade industrial dehumidifier. Drainage & Landscaping (2022–2023): New driveway, robust retaining walls, property drains along the tree line, a French drain system, and a new sump pump. Power & Utilities: New backup generator (2023), underground propane tank, and a certified cesspool with overflow system. Premium Extras: High-end Anderson windows throughout and an updated front door. With its pristine infrastructure and resort-style backyard, this turnkey property perfectly blends premium suburban comfort with your own private vacation destination.

10 S Lot Road, Smithtown

$995,000
7 Beds 3 Baths 1001866 MLS
Calling all land lovers! Step into this beautiful Smithtown home exclusively located in the Village of the Branch! This move-in ready ranch carries 7 bedrooms & 3 full bathrooms with a brick walkway to the entrance, a wrap around driveway & a 2 car attached garage nestled on a whole 1 acre of beautiful land. Part the Smithtown School District, it is zoned for Mt. Pleasant Elementary School, Great Hollow Middle School & Smithtown High School West. With many newly renovated updates, this home is designed for both everyday living & entertaining. The remodeled kitchen is complete with 2 islands, stainless steel appliances, abundant cabinetry & an open flow ideal for gatherings. The high ceilings in the fireplace living room provide a spacious area to create memories in. Located next to the kitchen there is an additional fireplace in the bedroom that has an attached bathroom as well. A washer & dryer is installed into the laundry room, with a sink & exit to the 2 car garage. The home carries hardwood floors throughout. The remodeled bathrooms, new vinyl siding, new roof, & new gas burner throughout the home create a lovely cozy atmosphere. Step out on to the deck & enjoy the expansive backyard on flat land. A newly constructed spacious shed within a beautiful view supports endless possibilities for recreation or your own private retreat. With generous living space, thoughtful upgrades, & an amazing location, this exceptional ranch surely offers a place to call home. There are plenty of reasons to fall in love with this exceptional & rare opportunity right in the heart of Smithtown's Village of the Branch!

80 Mount Pleasant Road, Smithtown

$949,999
6 Beds 3 Baths 993943 MLS
Beautifully renovated and move-in ready, this spacious 6-bedroom, 3.5-bath home offers the perfect blend of modern updates and flexible living. The primary suite features a walk-in closet and private full bath, while the updated kitchen with high-end appliances opens to bright, inviting living spaces. New central A/C and a new sprinkler system add comfort and convenience. Designed with versatility in mind, the home includes a layout ideal for extended living, guests, or a home office, with the potential to be used as a mother-daughter home (with proper permits). Situated on a half-acre lot, the property features a large backyard, Multiple car garage, and two separate driveways. Low taxes, plus a convenient location close to parks, shopping, and major highways, make this home an exceptional value.

56 McArthur Lane, Smithtown

$999,000
4 Beds 3 Baths 991907 MLS
Prestine 4-Bedroom Colonial with FULL BASEMENT in the Smithtown School District! Welcome to this beautifully maintained Colonial offering the perfect blend of elegance, space, and comfort. A charming wraparound porch sets the tone as you enter into an impressive entry foyer with soaring ceilings and a bright, open feel. The home features high ceilings throughout, a spacious den with vaulted ceilings, a stunning stone fireplace with natural gas, recessed lighting, smart thermostat, central air conditioning, central vacuum, and detailed wainscoting and much more. The newer chef’s kitchen is designed for both everyday living and entertaining, complete with stainless steel appliances. A dedicated laundry room with custom built-in cabinetry adds convenience and functionality. The primary suite is a true retreat, featuring his-and-hers walk-in closets and a large private bathroom with double vanity. Additional highlights include a newer roof and a newly updated expanded driveway, providing ample parking and enhanced curb appeal. A huge unfinished full basement with high ceilings offers incredible potential for future living space, storage, gym, or recreation area.

185 Plymouth Boulevard, Smithtown

$999,999
4 Beds 4 Baths 988386 MLS
Welcome to 5 Supreme Court, Smithtown – Located in the Highly Sought-After Hauppauge School District with Low Taxes ($16,940). This spacious Post Modern home offers an exceptional layout with soaring ceilings and a dramatic 24-foot foyer entry, creating a grand first impression. The open floor plan features hardwood flooring, a bright and airy living and dining area, and a center island kitchen ideal for both everyday living and entertaining. Offering 4 bedrooms with an optional 5th bedroom or home office on the main level, this home provides flexibility to suit a variety of lifestyles. The primary suite features a double-door entry, and the home includes wood and ceramic flooring throughout. The full, finished basement with outside separate entrance (OSE) and full bath adds valuable additional living space. Additional highlights include natural gas, baseboard heating, central air conditioning and the property is set on a private cul-de-sac.

5 Supreme Court, 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.