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458 Route 111 (Hauppauge Road), Smithtown
$655,000
3 Beds ⋅ 2 Baths ⋅ 995008 MLS
This beautifully maintained expanded Cape offers 3 spacious bedrooms and 2 full baths, primary bedroom on the main floor for added convenience. The den/loft overlooking the living room is ideal for a home office, reading nook, or living space. The full, part finished basement provides plenty of room for recreation, storage, or future customization. A standout feature is the 2-car garage w/one bay heated, complete with washer, dryer, and a slop sink—perfect for year-round use. Recent updates include stainless steel appliances (with a refrigerator just 5 months old), updated windows and baths, and upgraded waste pump and piping. The home is equipped with efficient 2-zone gas heating (installed in 2012) and a brand-new hot water heater (April 2026). Step outside to enjoy a large deck with an electric awning, ideal for entertaining, along with a 6-zone sprinkler system and so much more. The fully fenced property also features an oversized 6-car driveway, offering ample parking for guests. Low taxes of just $8,451 annually—making this home an exceptional value.

458 Route 111 (Hauppauge Road), Smithtown

291 Terry Road, Smithtown
$655,000
3 Beds ⋅ 2 Baths ⋅ 934815 MLS
Welcome home to this beautiful 3 bed 1.5 bath expanded cape home. First floor has charming open floor plan featuring sunny kitchen with breakfast nook, dining area & living room. First floor bedroom can also be used as home office, playroom etc... First floor full bathroom has gorgeous spa like walk in shower. Second floor has generous size primary bedroom & additional bedroom. Second floor also has half bath that has plenty of room to convert to full bath. Home has plenty of storage options with unfinished basement where washer & dryer are located as well as very large 2 car garage & shed. Major updates completed in last 10 years are Navien gas heating/hot water system, roof, siding, kitchen, bathrooms, landscaping & cesspool. Hurry this fabulous home with LOW taxes in Smithtown schools will not last!

291 Terry Road, Smithtown

4 Landing Meadow Road, Smithtown
$650,000
3 Beds ⋅ 2 Baths ⋅ 1009540 MLS
Step into a piece of Smithtown history with this charming Colonial, where timeless character and thoughtful updates come together beautifully. Nestled on a picturesque half-acre property in North Smithtown, this 3-bedroom, 2-bath home offers warmth, personality, and the kind of craftsmanship that is hard to find. Inside, you’ll find an inviting foyer and living room highlighted by a cozy wood-burning fireplace and charming architectural details throughout. The formal dining room features beautiful built-in cabinetry and a bay window with stained glass accents. The country-style kitchen flows seamlessly into a comfortable den, creating the perfect gathering space for everyday living and entertaining. Stainless steel appliances and abundant natural light enhance the home’s welcoming feel. The main level also offers an additional room currently used as a home office, which could also serve as a laundry room, or flex room to suit a variety of needs. Three bedrooms are located on the second floor, and two full bathrooms provide convenience, with one located on each level. Recent updates and improvements include a gas conversion, newer burner, 200-amp electric service, and three split units that provide both heating and cooling. Outside, enjoy a private setting with mature landscaping, a fully fenced yard, a spacious driveway with brick accents, and curb appeal that perfectly complements the home’s historic character. A rare opportunity to own a home filled with charm, warmth, and modern conveniences. Conveniently located near Sweetbriar Nature Center, Landing Avenue Park, and the shops, restaurants, and amenities of Smithtown’s vibrant East Main Street. Taxes totaling $6,157.90 annually.

4 Landing Meadow Road, Smithtown

263 N Country Road, Smithtown
$650,000
3 Beds ⋅ 3 Baths ⋅ 973518 MLS
Welcome to this beautifully updated 3 bedroom & 3 full bathroom ranch-style home in the heart of Smithtown, offering the perfect balance of comfort, space, and convenience. Inside, you’ll find refinished wood floors and freshly painted interiors that create a warm, inviting feel throughout. The layout is both practical and flexible, featuring a bright eat-in kitchen ideal for everyday living, along with a formal dining room for gatherings. The main level includes a primary bedroom with its own ensuite bath, plus an additional bedroom and full bathroom. A separate entrance adds valuable versatility, leading to a spacious den with a fireplace, bedroom, and full bath—perfect for guests or a private home office setup. The den features a cozy fireplace that opens up to a spacious deck - ideal for summer barbecues. Finished full basement complete with egress window and many cedar closets providing plenty of storage. Set on a generous .63 acre corner lot and located just minutes from shopping, dining, top-rated Smithtown schools, and Stony Brook University, this home offers both convenience and lifestyle. Move-in ready with recent updates including a new cesspool (2025), hot water heater (2023), 200 Amp Electric (2023), and Anderson windows.

263 N Country Road, Smithtown

32 Scarborough Drive, Smithtown
$650,000
2 Beds ⋅ 3 Baths ⋅ 928242 MLS
Welcome to Windcrest at Smithtown, a desirable pet friendly gated community offering maintenance free resort-style living! This beautifully maintained Brittany model townhome features 2 spacious bedrooms and 2.5 baths. The extensive primary suite boasts two walk-in closets and a private bath. Additional highlights include a private outdoor patio, one-car garage with epoxy flooring, driveway parking and a full basement offering endless possibilities for storage or recreation. Enjoy resort-style amenities including a clubhouse with cardroom, TV and sitting room with fireplace, outdoor swimming pool, tennis courts, fitness center, gazebo overlooking pond with fountain--all in a convenient location close to shopping, dining, McArthur Airport and LIRR. Experience low maintenance living with all the comforts of home!

32 Scarborough Drive, Smithtown

239 Pond View Lane, Smithtown
$650,000
3 Beds ⋅ 3 Baths ⋅ 878384 MLS
Smithtown Townhome now showing! Spacious Dartmouth model in preferred Hidden Ponds Condominium Community. Updated granite EIK with island for entertaining guests, first floor laundry room, open floor plan, with sliders to back paver patio. Upstairs enjoy 3 spacious bedrooms with abundant storage. Primary bedroom with WIC, ensuite bath with soaking tub, shower and double vanity sink. One car attached garage with driveway and ample guest parking. 24/7 gated community with multiple amenities, including but not limited to : Community pool, tennis courts, pickleball courts, bocce ball, kiddie pool, fitness center, dog run, basketball, playground and clubhouse with kitchen and card/game room. Heating system less than 1 year old, CAC less than 1 year old with warranties.

239 Pond View Lane, Smithtown

214 Landing Avenue, Smithtown
$649,000
3 Beds ⋅ 3 Baths ⋅ 993736 MLS
**PRICE RESET AND TAX GRIEVANCE FILED(Letter in photos)** If you've been looking for a spacious home in Smithtown, with great bones and room to make it your own-without breaking the budget-THIS IS THE ONE! Lovingly maintained and full of RETRO CHARM -this 1972-built home is bursting with personality and untapped potential. From pink countertops and custom tile to lavender walls and carpeting, it’s like walking into a retro dream. With central air conditioning, electric heat, and central vac, this home offers a spacious center hall layout with a large living room, formal dining room with a sparkling Swarovski crystal chandelier and a spacious family room featuring slate accents and a wood-burning fireplace. A striking half bath with velvet wallpaper adds even more vintage charm. Upstairs, a winding staircase leads to three bedrooms and two full baths, including a primary bedroom with a walk in closet and bathroom with a dramatic oversized sunken tub. The home also features a full unfinished basement with outside access, a two-car garage with 1 garage door opener and with interior entry through the laundry room. This property sits on a private 2/3-acre flag lot with park-like grounds in a beautiful neighborhood off Milleridge Lane. Set back from Landing Avenue with a unique driveway beside 7 Milleridge Rd, this home offers privacy, space, and a rare opportunity. Located north of 25, this home is located near LIRR and near bustling main street, filled with restaurants and shops galore. For nature enthusiasts, parks and the Nisseqougue River are nearby. Restore or reimagine it entirely—either way, this is a one-of-a-kind property you truly have to COME SEE to believe. ***TAXES ARE OFFICIALLY BEING GRIEVED BY SELLER - LETTER IN PHOTOS- POTENTIAL TAX SAVINGS OF $2,700 IN ADDITION TO SMITHTOWN STAR BASIC*** **DIRECTIONS- ACCESS TO PROPERTY IS PRIVATE DRIVEWAY NEXT TO 7 MILLERIDGE LANE, OFF EDGEWOOD

214 Landing Avenue, Smithtown

34 Rose Court, Smithtown
$625,000
4 Beds ⋅ 2 Baths ⋅ 924399 MLS
PRICE JUST REDUCED BY $65,000!!! If you’ve been waiting for the right moment, this might be it. 34 Rose Court in the Pines section of Smithtown now offers even more value! This 4-bedroom, 2-bath Expanded Cape sits on a spacious corner lot of nearly half an acre. Step inside to find a bright living room, formal dining room, and an eat-in kitchen ready for your personal touch. The first floor features the primary bedroom with its own private bath, an additional full bathroom, and flexible bedrooms that can serve as guest rooms or a home office. The home also includes a full basement, one-car detached garage, and plenty of storage space throughout. Enjoy outdoor living in the expansive, level backyard—perfect for entertaining, play, or relaxation. Additional highlights include owned solar panels, super low taxes, and convenient proximity to shops, restaurants, parks, and major roadways. Located in the highly regarded Hauppauge School District, this home combines comfort, space, and potential in one of Smithtown’s most sought-after neighborhoods.Welcome to 34 Rose Court in the desirable “Pines” section of Smithtown! This 4-bedroom, 2-bath Expanded Cape sits on a spacious corner lot of nearly half an acre. Step inside to find a bright living room, formal dining room, and an eat-in kitchen ready for your personal touch. The first floor features the primary bedroom with its own private bath, an additional full bathroom, and flexible bedrooms that can serve as guest rooms or a home office. The home also includes a full basement, one-car detached garage, and plenty of storage space throughout. Enjoy outdoor living in the expansive, level backyard—perfect for entertaining, play, or relaxation. Additional highlights include owned solar panels, super low taxes, and convenient proximity to shops, restaurants, parks, and major roadways. Located in the highly regarded Hauppauge School District, this home combines comfort, space, and potential in one of Smithtown’s most sought-after neighborhoods.

34 Rose Court, Smithtown

4 Chelsea Drive, Smithtown
$618,000
2 Beds ⋅ 3 Baths ⋅ 944448 MLS
Welcome to 4 Chelsea Drive, Smithtown! Set within the desirable Windcrest Community sits this beautifully maintained 2 bedroom, 2.5 bath Townhouse that offers an open concept living room with fireplace, an updated kitchen with stainless steel appliances. Hardwood floors throughout the first floor, Upstairs, Primary en-suite with Updated Bathroom, 2 WIC's. Generous size 2nd Bedroom and 2nd Full Updated Bathroom. Carpeting upstairs. Additional updates include Tristate windows installed in (2014), Sliding glass door (2019), Heating (2022), Water heater (2023), CAC units, upstairs unit (3 years) and downstairs unit (10 years) Carpeting Upstairs. One car attached garage and a full basement with plenty of storage!! Enjoy the great Community amenities that Windcrest has to offer including an in-ground salt water pool, tennis courts, pickle ball, clubhouse and gym.

4 Chelsea Drive, Smithtown

39 William Street, Smithtown
$610,000
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

73 S Pond Lane, Smithtown
$610,000
2 Beds ⋅ 2 Baths ⋅ 1008290 MLS
Welcome to 73 South Pond Lane, a beautifully maintained townhouse nestled within the highly desirable Hidden Ponds community in Smithtown. This spacious residence offers an ideal blend of comfort, convenience, and low-maintenance living. Step inside to find a bright and inviting layout featuring generous living space, and oversized windows that fill the home with natural light. The primary suite offers ample closet space and an en-suite bath, while a spacious second bedroom and separate full bath provide comfort and flexibility for guests, a home office, or everyday living. Enjoy outdoor relaxation on your private patio. Hidden Ponds is a gated community known for its beautifully landscaped setting, ponds, walking paths, clubhouse, pool, tennis courts, and carefree lifestyle. Conveniently located near shopping, dining, parks, major roadways, and all that Smithtown has to offer. Don't miss this opportunity to own in one of Smithtown's most sought-after communities. Move right in and enjoy resort-style living every day.

73 S Pond Lane, Smithtown

27 Lindner Place, Smithtown
$600,000
3 Beds ⋅ 1 Baths ⋅ 1004798 MLS
Welcome to 27 Lindner Place, Smithtown! This completely move-in ready and fully updated 3-bedroom, 1-bath home offers the perfect blend of modern updates, comfort, and property space. Featuring a brand new kitchen with stylish finishes, updated interior throughout, and a spacious layout, this home is ready for its next owner to move right in and enjoy. Situated on a rare half-acre property, the oversized lot provides endless possibilities for entertaining, expansion, outdoor living, or simply enjoying your own private space. Even better, this home offers incredibly low taxes for the area, adding exceptional value and affordability. Conveniently located near shopping, parks, restaurants, and major roadways while still offering the charm and privacy of Smithtown living. Do not miss this opportunity to own your piece of Smithtown!

27 Lindner Place, Smithtown

4 Washington Avenue, Smithtown
$600,000
3 Beds ⋅ 1 Baths ⋅ 937210 MLS
Discover the ease of one-level living in this charming 3-bedroom, 1-bath ranch nestled in the heart of Smithtown! Step inside to refinished hardwood floors, fresh paint, new vinyl flooring, and updated lighting that offer a welcoming, move-in-ready atmosphere. The spacious one-car garage and an expansive open unfinished basement—featuring large windows—provide endless possibilities for storage, recreation, or future finishing. A standout feature is the legal 14'8" x 9' extension, a versatile space perfect as a second living area, formal dining room, home office, or future 2nd bath/laundry/mudroom—tailor to suit your needs. Conveniently situated near Smithtown Main Street, with quick access to the LIE and train station—commuting is a breeze. Take advantage of nearby parks and beautiful Long Island beaches for outdoor enjoyment. With its solid updates providing a fresh baseline, this home is ready for your personal finishing touches. Don’t miss the opportunity to unlock the potential of this classic ranch in a prime Smithtown location! Public gas available on the street. Central air conditioning. Taxes only 10301.70.

4 Washington Avenue, Smithtown

248 Pond View Lane, Smithtown
$595,000
2 Beds ⋅ 2 Baths ⋅ 940653 MLS
Rare Opportunity In Hidden Ponds! Don't miss this beautifully updated end-unit Emory Ranch. A meticulously maintained, one-story 2 bedroom, 2 bath home in the desirable gated community of Hidden Ponds. Enjoy exceptional privacy with a park-like backyard and the convenience of an attached garage with an oversized driveway. Inside, an eat-in-kitchen with breakfast area is flooded with light from 3 walls of windows, a spacious living room and formal dining room feature an open floor plan with vaulted ceilings, new luxury vinyl plank flooring & new LED recessed lighting throughout, with sliders leading to your outdoor living space. A generous primary suite includes a walk-in closet, en-suite bath, and serene views of the rolling lawn. The second bedroom doubles perfectly as a den or home office, offering flexibility to meet your personal needs. Additional conveniences include a hall laundry closet and attic storage. Hidden ponds offers resort-style living with a clubhouse With a shared 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. Ideally located off 347 for easy access to major roadways, Smith Haven Mall, Main Street Smithtown, and more... Welcome to a community that truly has it all!

248 Pond View Lane, Smithtown

91 Hidden Ponds, Smithtown
$575,000
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

79 S Pond Lane, Smithtown
$575,000
2 Beds ⋅ 2 Baths ⋅ 1005438 MLS
Don’t miss this beautifully maintained end-unit Emory Ranch, a meticulous one-story home offering 2 bedrooms and 1.5 baths in the highly desirable gated community of Hidden Ponds. Enjoy exceptional privacy with a park-like backyard, plus the convenience of an attached garage and oversized driveway. Inside, the sun-filled eat-in kitchen features a charming breakfast area surrounded by windows on three sides. The spacious living room and formal dining room showcase an open-concept layout with vaulted ceilings and sliding glass doors leading to your private outdoor living space. The generous primary suite offers a walk-in closet, en-suite bath, and peaceful views of the rolling lawn. The second bedroom provides excellent flexibility and can easily serve as a den or home office to suit your needs. Additional conveniences include a hall laundry closet and attic storage. Additional updates include newer appliances, vinyl flooring, updated electric and updated shower in primary. Hidden Ponds delivers resort-style living with outstanding amenities, including a clubhouse, movie/card room, mail room, fitness center, ping-pong, bocce, heated saltwater pool, tennis and pickleball courts, playground, and dog park — all within a pet-friendly community. Ideally located just off Route 347 with easy access to major roadways, Smith Haven Mall, Main Street Smithtown, dining, shopping, and more. Welcome to a community that truly has it all!

79 S Pond Lane, Smithtown

11 Rhoda Avenue, Smithtown
$530,000
3 Beds ⋅ 2 Baths ⋅ 890310 MLS
This charming ranch-style home, located at the end of the street in the highly sought-after Smithtown School District, offers inviting curb appeal and comfortable living. Step inside to a spacious living room, perfect for relaxing or entertaining guests. The eat-in kitchen provides ample space for meal prep and casual dining, with direct access to the yard for seamless indoor-outdoor living. Enjoy the bonus den, featuring sliders that lead to the backyard—ideal for summer barbecues and outdoor fun, with a large grassy area perfect for games and gatherings. The generously sized bedrooms offer a peaceful retreat after a long day. Additional highlights include updated bathrooms, central air for year-round comfort, and a convenient door from the kitchen to the yard. A PVC front fence adds privacy and style to the home’s exterior. Don’t miss this opportunity to own a home with both charm and function in a desirable location.

11 Rhoda Avenue, 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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