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8 South Avenue, Smithtown
$499,999
1 Beds ⋅ 1 Baths ⋅ 1052134 MLS
Welcome to 8 South Avenue, a charming one-bedroom, one-bath cottage situated on approximately 0.38 acres in Smithtown. The home features an updated kitchen, hardwood and vinyl flooring, and a functional layout filled with natural light. Step outside to a spacious, fully fenced backyard complete with a 4-zone in-ground sprinkler system, large detached garage/shed, and plenty of room to enjoy the outdoors. Notable improvements include a roof replaced in 2019, updated living room windows, driveway, and gutters. Oil heat, a utility basement, and remarkably low taxes of approximately $4,393 add to the appeal. 8 South Avenue combines a sizable property, low taxes, and room to make it your own.

8 South Avenue, Smithtown
5 Monitor Road, Smithtown
$689,999
2 Beds ⋅ 3 Baths ⋅ 1058725 MLS
Welcome to Willow Wood at Smithtown, a remarkable townhouse development featuring the stunning Apple Wood model with 1,900 interior square feet. As you enter, you’re greeted by a spacious foyer bathed in natural light from a skylight, leading to an open staircase that ascends to the second floor. Upstairs, you’ll find a well-designed layout that includes a primary en suite with two walk-in closets and a double vanity featuring both a tub and shower, alongside a second bedroom, also with a walk-in closet. Conveniently located off the bedroom is a laundry room for easy access. Returning to the main level, the cozy living and dining room combination showcases engineered hardwood floors and a gas fireplace, with sliding doors that open to a private patio—ideal for outdoor relaxation. The spacious eat-in kitchen is perfect for gatherings, while a conveniently located powder room and ample closet space throughout ensure both comfort and functionality. The home also includes a one-car garage with an electric opener, offering additional parking and storage solutions. For added security, the property is fully alarmed with Ring cameras at the front door and garage door. Monthly common charges of $500.00 includes landscaping and maintenance, access to the inground saltwater pool, clubhouse, and fitness center, snow removal, and water, along with discounts on Optimum TV and Internet services. Community amenities further enhance the living experience with an inground pool, clubhouse, fitness center, and a relaxing gazebo, all in a pet-friendly environment. Don’t miss out on this exceptional chance to live in a vibrant community at Willow Wood in Smithtown!

5 Monitor Road, Smithtown
365 Rt 111 Unit #A16, Smithtown
$269,000
1 Beds ⋅ 1 Baths ⋅ 1058457 MLS
Welcome to this one-bedroom, one-bathroom upper-level co-op in Tanglewood Terrace in Smithtown, offering approximately 750 square feet of comfortable, well-planned living space. The inviting eat-in kitchen provides a pleasant setting for casual meals, while the oversized living room offers plenty of flexibility for entertaining guests, relaxing or creating a dedicated home office. The hallway and bedroom closets provide convenient storage. Step outside to the private balcony for morning coffee, fresh air or a quiet evening retreat. Additional features include a blend of hardwood and carpeted flooring, baseboard heating, a wall-mounted air-conditioning unit, dishwasher, oven, refrigerator and freezer. A conveniently located basement laundry center adds everyday ease. Monthly maintenance is $1,225 and includes taxes, gas, heat, gas cooking, water, sewer and all exterior maintenance. Ideally situated near the Smithtown LIRR station, restaurants, shopping and major highways, this home combines comfortable living with convenient access to the surrounding area.

365 Rt 111 Unit #A16, Smithtown
296 Moriches Road, Smithtown
$699,000
3 Beds ⋅ 3 Baths ⋅ 1058587 MLS
Discover the perfect blend of modern updates, timeless appeal, and comfortable living in this beautifully updated 3-bedroom, 3-bath ranch in St. James. The inviting interior showcases hardwood floors, a welcoming living room with fireplace, and an updated kitchen featuring elegant quartz countertops and a breakfast bar. The finished lower level with a separate outside entrance offers exceptional flexibility for recreation, a home office, guests, or additional living space. Outdoors, enjoy a fully fenced property complemented by a stone patio and storage shed, creating an inviting setting for relaxation and entertaining. Additional highlights include gas heat and cooking. Ideally located directly across from a park and playground, with convenient access to shopping, dining, schools, and transportation. Thoughtfully updated and move-in ready, this home offers the perfect balance of style, functionality, and location.

296 Moriches Road, Smithtown
36 Mayflower Avenue, Smithtown
$629,900
3 Beds ⋅ 1 Baths ⋅ 1036399 MLS
Welcome home to 36 Mayflower Avenue, a beautifully renovated ranch where no detail has been overlooked and every update was made with care and intention. From the moment you arrive, the new front pavers, fresh siding, and a new stoop sets the tone for what's inside. Major mechanicals have all been taken care of such as a new water main, 200 amp electrical upgrade, new plumbing, and central air conditioning. You can move in with complete peace of mind. Inside, you'll fall in love with the renovated kitchen and bathroom. The living room is an absolute showstopper, featuring in-ceiling speakers with motion-detected digital surround sound, perfect for cozy nights in or entertaining guests. Anderson, Pella, and Velux windows flood every room with natural light, and the skylights with motorized blinds add a touch of luxury you didn't know you needed. Outside you're welcomed with a fully fenced backyard complete with beautiful pavers and a retaining wall, your own private retreat, ready for summer gatherings and quiet evenings alike.

36 Mayflower Avenue, Smithtown
45 Summit Drive, Smithtown
$399,000
4 Beds ⋅ 2 Baths ⋅ 1053453 MLS
NO INTERIOR ACCESS OR SHOWINGS. OCCUPIED PROPERTY. PLEASE DO NOT DISTURB OCCUPANTS. Property is being sold strictly as is. CASH OFFERS ONLY. Because interior access is unavailable, information regarding the property’s condition, layout, room count, features, and other characteristics has been obtained from public/tax records and/or estimated where necessary. All information should be independently verified by the buyer and accuracy is not guaranteed.

45 Summit Drive, Smithtown
143 Paddington Circle, Smithtown
$719,000
3 Beds ⋅ 3 Baths ⋅ 1051895 MLS
Enjoy country-club living in this fabulous three-bedroom, 2.5-bath townhouse in the sought-after gated community of Windcrest in Smithtown. The Dover model is the largest townhouse offered in this desirable community of 187 residences. The main level features an inviting living room with a gas fireplace, crown molding, and prefinished hardwood floors, seamlessly opening to the formal dining room. The bright kitchen offers white cabinetry, granite countertops, stainless steel appliances, and a comfortable eating area overlooking the rear paver patio.A cozy den provides the perfect space to relax after a long day. The spacious primary suite features double-door entry, two walk-in closets, and an en-suite bath with a double-sink vanity and soaking tub. Two additional bedrooms provide ample space for family or guests, along with a full hall bath featuring a bathtub with shower, The lower level offers a partial finished basement with laminate flooring and direct access to the two-car garage. Residents of Windcrest enjoy an exceptional array of amenities, including a beautiful remodeled clubhouse with fitness center, saltwater pool, pickleball courts, and tennis court.. This is a wonderful opportunity to enjoy luxury, convenience, and resort-style living in the heart of Smithtown, close to local shopping, fine dining, area beaches, and Stony Brook University and Medical Center. Smithtown Schools

143 Paddington Circle, Smithtown
47 Route 25A, Smithtown
$485,000
3 Beds ⋅ 1050824 MLS
18th Century Home in disrepair being sold AS-IS with great potential. Some previous upgrades to foundation and structure. Interesting property with double sided center fireplace and original beams and architectural features. Detached 2 car garage AS-IS with newer concrete flooring. Low taxes ...own a piece of history. No functional bathrooms, kitchen or heating.

47 Route 25A, Smithtown
10 Smithtown Boulevard Unit #6A, Smithtown
$349,999
1 Beds ⋅ 1 Baths ⋅ 1050327 MLS
Welcome to 10 Smithtown Boulevard, Unit 6A, a beautifully redesigned main-level residence offering elevated co-op living in the highly sought-after Smithtown School District. Completely transformed with modern finishes and thoughtful design, this home combines the comfort of a high-end residence with the value of co-op ownership. Sunlit interiors, seamless flow, and quality craftsmanship create a space that feels both sophisticated and inviting. A Rare and Highly Valuable Feature of this home is the fully enclosed and secure 300-square-foot private storage space located directly beneath the unit, offering exceptional convenience and flexibility rarely found in co-op living. The designer kitchen features custom cabinetry, sleek finishes, generous storage, and a spacious dining area perfect for everyday living or entertaining. The spa-inspired bathroom showcases clean lines and elegant modern details. The king-sized primary suite is exceptionally spacious for a one-bedroom and offers abundant closet space. A versatile flex area provides the ideal setting for a home office or quiet retreat. Light oak hardwood floors run throughout the home, complemented by crown molding, modern lighting, and a soft neutral palette that enhances the bright, airy feel. Additional features include: • Assigned parking for two vehicles Immaculate and move-in ready, this home presents a rare opportunity in one of Smithtown’s most desirable communities. One of a kind. A true step above.

10 Smithtown Boulevard Unit #6A, Smithtown
14 Morewood Drive, Smithtown
$749,000
4 Beds ⋅ 3 Baths ⋅ 1050209 MLS
Builder’s Model Colonial located in the desirable Morewood Estates of Smithtown, featuring 4 bedrooms with 2.5 baths. The main level offers a entry foyer, formal living room and formal dining room with beautiful hardwood floors, an eat-in kitchen with access to an oversized deck overlooking .44 acres of a beautiful natural backyard setting, and a cozy den with fireplace. Upstairs features all beautiful hardwood flooring throughout the 3 bedrooms. You have the primary bedroom, three additional bedrooms, and two full baths. A bonus area provides additional flexible space to suit your needs. Brand New Hot water heater just installed, newer roof 3 yrs old. Basement NOT finished inside entrance only. Conveniently located just minutes from shopping, dining, transportation, and more. This is a must see!

14 Morewood Drive, Smithtown
355 Route 111 Unit #30 Route 111 Unit #30, Smithtown
$280,000
1 Beds ⋅ 1 Baths ⋅ 1049471 MLS
Fantastic Opportunity to Own! Why rent when you can buy in Smithtown's Award winning School District. This Updated Corner Unit Has Hard Oak Flooring, Granite Countertops, Stainless Appliances, New Wall AC units, Laundry on site and Large Rooms with Plenty of Closet Space ..

355 Route 111 Unit #30 Route 111 Unit #30, Smithtown
5 Kenny Street, Smithtown
$749,990
3 Beds ⋅ 2 Baths ⋅ 1047017 MLS
Welcome to 5 Kenny Street, a charming ranch-style home nestled in the heart of Smithtown. This delightful residence boasts three comfortable bedrooms and two full bathrooms, ensuring ample space for all. Upon arrival, you are greeted by the home's impressive curb appeal, set on a generous .34-acre flat parcel. Inside, discover the hidden treasure of hardwood floors beneath the carpeting, preserved for years and ready to shine. The home is equipped with central air conditioning, an updated heating system, and a modern hot water heater for your comfort. Recessed lighting is throughout the house. The spacious living room invites relaxation, while the separate den, enhanced with a cozy gas fireplace, provides an intimate retreat. The kitchen shines with updated stainless steel appliances, a vaulted ceiling with a skylight, and a convenient formal dining room stands ready for your meals and gatherings. The primary bedroom offers the luxury of an ensuite bathroom. The second full bathroom has a skylit vaulted ceiling. This beautiful home has a two-car garage with electric openers, a partially finished large basement with ample storage, and a laundry area adds to the home's practical appeal. Outside, a low-maintenance Trex deck overlooks the picturesque backyard, an ideal spot for outdoor enjoyment. There is an in ground sprinkler system in the front and back yard. The backyard is very private. This home's location is a gem, with easy access to major highways, public transportation, and shopping venues. Welcome to your future home, where convenience meets charm in Smithtown and within the Smithtown School District.

5 Kenny Street, Smithtown
6 North Avenue, Smithtown
$725,000
4 Beds ⋅ 2 Baths ⋅ 1044596 MLS
Super Clean Home that Features 4 Bedrooms, 1.5 Baths, Hardwood Floors, Anderson Windows thru-out, 2025 New Burner, Whole House water filtration system, Roof 2011, Granite EIK around 2018, Fireplace in Family Room, Pull Down-stairs for attic storage, 200 AMPS Electric, Expanded Driveway plus 2-Car Garage, Natural Gas in street already if you want to convert, Fenced Yard with Deck, Patio, Gardens, Shed for storage, and Low Maintenance yard to maintain. Taxes $12k per year, Need Smithtown Schools, then view this home located close to town.

6 North Avenue, Smithtown
23 Riviera Drive, Smithtown
$674,999
3 Beds ⋅ 2 Baths ⋅ 1040470 MLS
Location! Location! Location! Welcome to this beautifully refreshed split-level home, where style, comfort, and versatility comes together in one Smithtown offering. From the moment you arrive, the new driveway, 3 year old hot water heater and freshly painted interiors with the cathedral ceiling sets the tone for a home that feels polished, inviting, and ready to enjoy. The home opens to a bright and thoughtfully designed layout offering 3 bedrooms and 2 full baths, with comfortable living spaces that transition effortlessly from everyday moments to entertaining family and friends. What truly sets this home apart is its versatile lower level with a separate entrance, creating exciting possibilities for extended living, a private home office, guest space, recreation area, or whatever best complements your lifestyle. Recent improvements add even more value and peace of mind, including a new gas burner and hot water heater, new dishwasher, and new washing machine. Go outside and enter the generous corner plot that provides the perfect backdrop for alfresco dining, summer gatherings, gardening, or simply unwinding at the end of the day. Thoughtfully updated, and filled with possibilities, this home delivers the space and flexibility today’s buyers are looking for, wrapped in a warm and beautifully presented home. With the top-rated Smithtown schools, and a neighborhood close to shopping, dining, highways and close to the train station, this is a special opportunity in Smithtown that deserves to be experienced in person.

23 Riviera Drive, Smithtown
36 Fifty Acre Road S, Smithtown
$699,999
4 Beds ⋅ 2 Baths ⋅ 1036685 MLS
Welcome to this newly renovated 4 bedroom, 2 bathroom Expanded Cape home, located on a 0.38 Acre lot, in a desirable area of Smithtown, NY. The main level boasts a beautiful inviting living room with a bay window, designer molding, recessed lighting, new flooring, and sliders to backyard, an open concept kitchen with stainless steel appliances, dining area with sliders for quick access to backyard, 2 first floor bedrooms, a brand new full bathroom and a laundry area. The upper level offers a very spacious, sun drenched primary bedroom with ensuite bathroom, high ceilings with skylights, plenty of closets, and a forth bedroom. The HUGE backyard has transformed into an entertainer’s paradise, featuring an in-ground pool with waterfall, new pool filtration system, in-ground sprinkles, two charming wooden decks, a large two car garage for storage, two sheds and a spacious workshop space in the back that creates a stunning outdoor space perfect for enjoying the warm summer days. Additional improvements include, new appliances, new bathroom, new flooring, recessed lighting, new doors, updated stone out siding, freshly painted interior walls, tree removals, yard leveling, new landscaping, and new pool filtration system. This property is in a PRIME location of Smithtown. Close to Smithtown LIRR train station, Main Street dining & shopping, Smithtown schools, Blydenburge County park, Caleb Smith State Park, Smithtown library, and many other amenities.

36 Fifty Acre Road S, Smithtown
42 Pineacre Drive, Smithtown
$699,999
3 Beds ⋅ 1 Baths ⋅ 1030650 MLS
Well-Maintained Cozy Ranch on a Beautiful Tree-Lined Street in Smithtown Welcome to this charming and well-maintained ranch nestled on a picturesque, tree-lined street in Smithtown, set on a generous .63-acre property with a detached garage. This inviting home offers a comfortable and functional layout featuring a formal living room, formal dining room, cozy den, and an eat-in kitchen with propane cooking. The home offers three bedrooms and one full bathroom, providing plenty of space for comfortable living. Anderson windows and beautiful hardwood floors in the living room add warmth and character to the home. Outside, enjoy the expansive property with plenty of room for outdoor activities, entertaining, gardening, or simply relaxing in your own private setting. The detached garage provides additional storage and convenience. A wonderful opportunity to own a lovingly maintained ranch in a desirable Smithtown location.

42 Pineacre Drive, Smithtown
74 Cornell Drive, Smithtown
$739,000
3 Beds ⋅ 2 Baths ⋅ 1001880 MLS
Welcome to 74 Cornell Drive a beautifully maintained 3-bedroom split-level brick and vinyl home tucked on a quiet, established Smithtown block where pride of ownership shows in every direction. From the moment you arrive, you’re greeted by a wide, spacious driveway and a meticulously kept lawn that sets the tone before you even step inside. This is a home that feels cared for inside and out. Step through the door and you’re met with natural light pouring through large windows, enhanced by recessed lighting that creates a warm, modern glow throughout the living spaces. The kitchen is outfitted with stainless steel appliances, designed for both everyday living and effortless entertaining. Upstairs offers three well-proportioned bedrooms, providing comfort, flexibility, and space for everyone. Two full bathrooms deliver convenience and functionality for modern living. Out back is where this home truly comes alive a beautifully kept backyard with a patio made for gathering. It’s the kind of space that naturally pulls people together, whether it’s quiet mornings or summer evenings with friends. Schedule a tour today

74 Cornell Drive, Smithtown
106 Summit Drive, 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
20 Veronica Court, Smithtown
$699,000
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

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