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66 Canterbury Drive, Wading River
$1,249,000
5 Beds ⋅ 7 Baths ⋅ 1010804 MLS
Welcome to 66 Canterbury Drive, a magnificent custom residence that perfectly blends elegance, comfort, and exceptional living space. A welcoming front porch sets the tone, offering the perfect place to relax and enjoy peaceful surroundings. Designed for both everyday living and grand-scale entertaining, this impressive home features an oversized gourmet kitchen, a spacious formal living room, elegant dining room, cozy den with a fireplace, bright sunroom, and a convenient powder room on the main level. A beautiful double staircase adds both style and functionality within the home. The luxurious second-floor primary suite is a private retreat, complete with a sitting area and fireplace, en-suite bathroom, and two generous walk-in closets. This level also features two additional en-suite bedrooms, a fourth bedroom, and a fourth full bath. The additional upper level offers a private fifth bedroom with a full bath, ideal for guests, extended family, or an au pair suite. The expansive finished walkout basement provides an abundance of additional living space, featuring a full bath and multiple bonus rooms perfect for a recreation area, home theater, fitness room, office, or playroom. Situated on a sprawling property, the fully enclosed backyard offers endless possibilities to create your own outdoor oasis, perfect for entertaining, relaxing, and enjoying the outdoors. This extraordinary home showcases timeless design, impressive proportions, and unmatched versatility, making it a rare opportunity not to be missed.

66 Canterbury Drive, Wading River

1799 Wading River Manor Road, Wading River
$980,000
4 Beds ⋅ 3 Baths ⋅ 1001830 MLS
Endless Possibilities & Opportunities for Buyers Looking for an Updated Home with a Separate Guest Cottage for the Extended Family. There is also a Barn that could possibly be used for Horses and 1 1/2 Acres of Property that could be used as a Gentleman's Farm. The Barn can also be a Delight for Car Enthusiasts as it has a Working Car Lift and 2 Garage Doors, one is 12' high. The Main House has a Wide Covered Wrap Porch + 4 Bedrooms and 3 Full Baths. The Foyer has 2 pocket doors, one leading to a First Floor Small Bedroom or Office and the Other Door Invites You to a very Open, Spacious Living Room and Dining Room. The Other Bedrooms are all Upstairs. The Primary Bedroom (20' x 30') has an attached area (12 x 22) that can be used as a Walk In Closet, an Office, Nursery or Sitting Room. The Kitchen has Updated Cabinets, a Double Oven, Gas Cooktop & an Island that's Great for Snacks or Meal Prep. There are Crown & Base Moldings, Andersen Windows with Natural Trim and 2 Bay Windows Allowing for More Natural Light. The House has a Full Basement as well as a rear Deck and Brick Patio. The Updated Buderus Furnace Heats the Home with Natural Gas. There is Central Air and Ducts for Central Vac. There is also an over sized 2 Car Attached Garage (528 sq. ft.) The Private Guest Cottage (approx 780 Sq. Ft) has a Floor to Ceiling Window for a view of the patio & yard. It is set up as a Studio with High Ceilings that have Exposed Natural Pine Beams and a Ductless Heat & A/C Split System. The Spacious yard is Surrounded by Trees and Fencing so it has a private setting. This May Be Just What You Are Looking For in a Home and Property!

1799 Wading River Manor Road, Wading River

36 Leonard Street, Wading River
$949,000
4 Beds ⋅ 3 Baths ⋅ 1036765 MLS
Located in the Quail Hollow section of Wading River is this beautifully updated 4-bedroom, 2.5-bathroom home in the desirable Shoreham-Wading River School District! From the moment you arrive, you’ll appreciate the thoughtful updates, bright interiors, and exceptional outdoor living this home has to offer. The heart of the home is a beautifully bright kitchen filled with lots of windows and natural light, creating a warm and inviting space for everyday living and entertaining. Hardwood floors add timeless appeal to the den, while the basement provides valuable additional space for future plans. Step outside and discover your own private backyard retreat featuring bluestone pavers and a new 18' x 38' saltwater pool with a deep-end bench built in 2024. The pool also comes equipped with an electric heat pump and automatic safety cover. New backyard in-ground sprinklers, professional landscaping, and a newly paved driveway complete the exterior. The property also features a 2 car detached garage in the backyard by the pool with interior amenities and stairs leading to a 600sf loft for additional storage. Both the attached 1 car garage and the detached garage feature durable epoxy floors, providing a clean and polished finish. Additional updates include central air conditioning (2022), new front and rear Therma-Tru doors, new screens, and extensive landscaping improvements. Located near town beaches, shopping, dining, vineyards, farm stands, and all that the North Fork has to offer. This home combines comfort, convenience, and resort-style outdoor living in a wonderful Shoreham-Wading River setting. Move right in and enjoy everything this exceptional property has to offer!

36 Leonard Street, Wading River

169 Overhill Road, Wading River
$899,000
4 Beds ⋅ 3 Baths ⋅ 1038680 MLS
Welcome to the North Shores most desirable area of Wading River. Built in 2019 with exceptional quality and attention to detail. This stunning Colonial is nestled in the desirable community of Wading River. Offering 4 bedrooms and 2.5 baths, this inviting home combines timeless charm with modern comfort and effortless living. A welcoming covered front porch sets the tone as you enter a light-filled interior featuring rich red oak flooring, LED hi-hat lighting, and a thoughtfully designed floor plan. The spacious kitchen boasts granite countertops and stainless steel appliances, making it both stylish and functional for everyday living and entertaining. A convenient laundry/mud room provides excellent organization and easy access to the full basement, offering abundant storage or future living possibilities. The home is equipped with propane heating and central air for year-round comfort. Step outside to an expansive deck, perfect for summer entertaining, dining, or relaxing while overlooking the beautifully landscaped property. The fully fenced yard provides privacy and plenty of space to enjoy the outdoors. Completing the package is a 2-car garage with ample additional parking and storage. Beautifully landscaped and thoughtfully designed, this move-in-ready is a perfect place to call home and enjoy a relaxing lifestyle close proximity to beautiful beaches, fine Restaurants, Farm Stands, and top rated Wineries.

169 Overhill Road, Wading River

60 Randall Road, Wading River
$799,999
3 Beds ⋅ 3 Baths ⋅ 850645 MLS
Deal fell through. Seller Motivated!!!! Will hear all offers!!! Offers to be CASH or Committed Mortgage Letter. No expense was spared for this beauty which was custom built in 1996 by Lars Torkelsen Builders. 8" Centers on Beams makes for a solid structure. (Seller in possession of original approved blue print) The home features 3 bedrooms 2 1/2 baths with 2 bonus rooms one of the bonus rooms has three windows and is approximately 200 square feet. 200 amp electrical panel. Ground floor is 1,224 sq. ft. and 2nd Floor is 1,944 sq. ft. Attached 2 car high ceiling heated Garage features remote open/close, an exterior door leading to back yard and window. Central Vac, Steel beam over garage to support primary bedroom. Primary bedroom features 3 massive closets and an enormous private ensuite. High ceilings throughout including in Attic and Basement Gutter leaf-guards; no more climbing on a ladder to clean the gutters. Underground electrical pet fence, Standup full attic, as well as a full unfinished basement with outside entrance. Lots and lots of storage. Plenty of room for a growing family. Desirable Shoreham-Wading River School District. Come and give this gem in the rough some love and create your own oasis on the 1.83 lot with POSSIBLE sub-division. (Seller has survey showing possible sub-division)

60 Randall Road, Wading River

67 Randall Road, Wading River
$789,990
5 Beds ⋅ 4 Baths ⋅ 1022011 MLS
Ready for room to spread out? This generously proportioned five-bedroom, three-and-a-half-bath residence delivers 3,156 square feet of thoughtful living space, perfectly perched off a peaceful cul-de-sac block on a lush .70-acre parcel. A dramatic two-story entry foyer sets the stage, welcoming you into interiors freshly painted in soothing neutral tones. Warm wood floors extend throughout, while French doors connect the living room and great room, creating flexible for both quiet evenings and lively celebrations. A woodburning stone fireplace anchors the space, and the kitchen impresses with granite counters and a pantry Comfort comes standard, thanks to central air, First Floor laundry, Anderson windows, and an architectural roof. The Spacious primary bedroom comes equipped with a Ensuite Bathroom and Large Entry Closet. The Stylish, legal accessory apartment, offers great potential for guests or supplemental income. Just outside is your entertainer's deck, where summer barbecues and morning coffee feel equally at home. A charming front porch, shed, inground sprinklers, and an enormous driveway round out the exterior with practicality and curb appeal. Set within the highly regarded Shoreham-Wading River School District, this location keeps daily life delightfully convenient. Grab groceries at nearby King Kullen, unwind with friends at North Tavern, and enjoy easy access to beaches, wineries, and the natural beauty this coastal community is famous for. Homes this spacious and versatile rarely last long—come see everything this Wading River gem has to offer before someone else claims it.

67 Randall Road, Wading River

59 Hidden Pheasant Path, Wading River
$649,999
4 Beds ⋅ 4 Baths ⋅ 1042943 MLS
Victorian Charm with Endless Potential in Wading River! Welcome to 59 Hidden Pheasant Path, a stunning Victorian-style home offering space, character, and incredible potential. Featuring 4 bedrooms and 3.5 bathrooms, this spacious property has a versatile layout designed for comfortable living and entertaining. The home boasts a welcoming front porch, a large finished basement with multiple rooms providing tremendous flexibility for a recreation room, home office, gym, guest space, or additional living areas, and a beautiful in-ground pool perfect for enjoying summer days. An oil BBQ adds another great feature for outdoor entertaining. The property retains the charm and character of a classic Victorian while offering the opportunity for the next owner to bring their own vision and modern updates. With some renovation and updating, this home has the potential to become an exceptional residence in a desirable Wading River setting. If you're looking for a home with character, space, and the opportunity to create something truly special, 59 Hidden Pheasant Path is one you won't want to miss.

59 Hidden Pheasant Path, Wading River

25 Cherry Lane, Wading River
$619,996
3 Beds ⋅ 2 Baths ⋅ 1015466 MLS
Location, location! Nestled in a highly desirable beachside community, this sun-drenched and fully updated 3-bedroom, 2-bath split ranch offers the perfect blend of coastal charm and modern luxury—with private access to the water just a stones throw away. Make this your year round or weekend getaway. Step inside to an open-concept main level featuring soaring ceilings, gleaming hardwood floors, and a spacious living and dining area. The beautifully renovated eat-in kitchen is a showstopper, with crisp white cabinetry, quartz countertops, a glass tile backsplash, stainless steel appliances, and a stunning center island with seating—ideal for entertaining. Custom blinds and recessed lighting add a refined touch throughout. Both bathrooms have been thoughtfully updated with modern ceramic tile and high-end finishes. The lower level offers a den with sliding doors to the outside and a full bath—perfect for guests, a home office, or extended living space. An additional third bedroom or entertainment area awaits on the lowest level, providing flexible space for gatherings, game nights. All of this, located just minutes from award-winning wineries, top-rated restaurants, and outlet shopping. This beachside beauty won’t last—don’t miss your chance to own a piece of paradise on Long Island’s North Shore!

25 Cherry Lane, Wading River

14 Sylvester Road, Wading River
$619,990
3 Beds ⋅ 3 Baths ⋅ 1004968 MLS
Unique Contemporary Home situated on a Private .69 acres in a Wonderful Neighborhood in "The Hills of Wading River" The Home Boasts: an Open Floor Plan with 2,373 sq ft of living space. Large Living Room with Cathedral Ceilings. Large Dining room for Family gatherings with French Doors leading out to Trex Deck. Hardwood Flooring Throughout. Kitchen with 3 Ovens, Terra Cotta Flooring and a Pantry. Huge Open Master Bedroom with Cathedral Ceilings, 2 Skylights, 3 Closets and a Loft. Master Bath with Tub and Stand up Shower and Skylight. The Bottom Floor has 2 Bedrooms and a Jack and Jill Bathroom with Updated Tile Flooring. Walk out Attic over Car Port. Mostly Andersen Windows throughout. Oil Burner (2 Years old). Roof, Windows and Siding (Updated 14 Years). Must See!

14 Sylvester Road, Wading River

8 Hill Street E, Wading River
$579,000
3 Beds ⋅ 1 Baths ⋅ 1005714 MLS
Welcome to this well-maintained 3-bedroom, 1-bathroom home located just a half mile from the beach. Enjoy a sunny, fenced backyard featuring a beautiful bluestone patio—perfect for relaxing, entertaining, or summer barbecues. This inviting residence has been a cherished family home for years. Additional highlights include a spacious attached two-car garage, single-level living, and low-maintenance ownership with economical operating costs. Whether you’re looking for a year-round residence, a downsizing opportunity, or a beach-area retreat, this practical and comfortable home offers a relaxed lifestyle in a desirable Wading River location. Just minutes from beaches, parks, wineries, and all the North Fork and Wading River area have to offer.

8 Hill Street E, Wading River

104 21st Street, Wading River
$429,000
2 Beds ⋅ 2 Baths ⋅ 1026277 MLS
Welcome to 104 21st Street in Wading River, where thoughtful updates, a rare double lot, and an unbeatable location come together. Situated on .29 acres with room for future expansion, this move-in ready home features hardwood floors throughout, a bright living room and dining room combination, and a beautifully updated interior. The walk-out lower level offers excellent flexibility with the potential for an accessory apartment with the proper permits, making it ideal for extended living arrangements, guests, or additional living space. Major improvements include a newer electrical service, newer heating system, newer windows, and a roof approximately 10 years young, providing peace of mind for years to come. Outside, enjoy a fully fenced backyard, a paver driveway and patio, and an oversized one-car garage with plenty of storage. Just a short walk to the private beach and scenic nature trails, this exceptional property offers the perfect balance of comfort, outdoor space, and coastal living. With two included lots totaling .29 acres and endless potential, this is a unique opportunity you won't want to miss.

104 21st Street, Wading River

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.