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547 Shore Drive, Oakdale
$2,199,000
5 Beds ⋅ 4 Baths ⋅ 1050358 MLS
Welcome to Osprey Landing — Your Private Waterfront Retreat! Discover the rare opportunity to own 2.2 acres of private waterfront paradise in Oakdale, where expansive water views, exceptional privacy, and a true boater’s lifestyle comes together in one remarkable property. Set on a private peninsula, this 3,800-sq. ft. plus, 5-bedroom, 3.5 bath Colonial offers an ideal blend of space, comfort, and versatility. Open-concept layout creates an inviting flow for both everyday living and entertaining, complemented by an eat-in kitchen with top-of-the-line appliances, den with fireplace/wood burning soapstone stove, living room, and elegant formal dining room. The thoughtfully designed 1st floor also includes a bedroom with a full bath, providing an ideal private in-law, guest, or au-pair suite. Upstairs, the spacious primary suite offers a peaceful retreat with a private ensuite bath, walkout outdoor balcony, and multiple walk-in closets, while additional bedrooms provide flexibility for family, guests, or a home office. Large unfinished third-floor attic offers valuable expansion potential — an opportunity to create additional living space tailored to your vision. Step outside and experience what makes Osprey Landing truly special. The waterfront patio, complete with a built-in kitchen: mini-refrigerator, sink, cabinets, and a gas barbecue, is perfectly positioned to take in tranquil canal views and create unforgettable moments with family and friends seated along the bar or dining table near the hot tub. Follow the steps down to your private dock with water and electric, offering direct access to the protected waterfront. A 15,000lb boat lift and additional second dock is permitted, subject to required approvals. Additional features include 2 sheds and an attached two-car garage adding storage and convenience. Located within the Connetquot School District and just minutes from the Oakdale LIRR, Sunrise Highway, restaurants, and a South Shore marina, this property combines privacy and waterfront living with convenient access to everything you need. Osprey Landing is more than a home — it is a rare waterfront lifestyle. Private acreage, protected water, boating access, generous living space, and room to create something truly your own make this an opportunity that rarely comes to market. Buyer to independently verify dock permitting and boat-lift requirements with the Town of Islip. All dimensions, square footage, and other property information are approximate and should be independently verified by the buyer.

547 Shore Drive, Oakdale

16 Twin River Drive, Oakdale
$1,475,000
4 Beds ⋅ 3 Baths ⋅ 1039412 MLS
Tucked away on a private South of Montauk cul-de-sac in Oakdale’s coveted Idle Hour community, this exquisitely reimagined 3,700 sq. ft. coastal colonial rests on a beautifully landscaped 0.7-acre waterfront lot with direct water access—offering the rare ability to launch jet skis, kayaks, and paddleboards from your own backyard. Seamlessly blending timeless South Shore architecture with sophisticated modern smart-home features, the residence delivers an exceptional lifestyle in one of the area’s most desirable enclaves. The sun-filled main level showcases an open-concept design with refined custom millwork, an elegant living room with gas fireplace and a chef’s eat-in kitchen appointed with quartz countertops, premium stainless appliances, and a built-in beverage center. The main-level primary suite offers a serene retreat, complete with dual walk-in closets and a stunning bath with smart-controlled heated tile floors, making it ideal for luxurious everyday living or private guest accommodations. Upstairs, three generously scaled bedrooms feature custom shiplap detailing, expansive closet space, and a beautifully finished full bath. The exterior has been transformed with exceptional attention to detail, featuring a grand TimberTech front porch with sleek black aluminum metal roof, new planting beds, and mature American boxwoods. The resort-like backyard has been fully cleared, leveled, and hydroseeded with lush Kentucky bluegrass, then enclosed with black horizontal aluminum and estate fencing, framed by 60 Green Giant arborvitae for ultimate privacy. Additional highlights include a resurfaced patio and an 11-zone smart Hunter irrigation system. Perfectly positioned near the river, marinas, LIRR, and top-rated Connetquot schools, this remarkable home offers an unmatched blend of elegance, comfort, and coastal living south of Montauk Highway

16 Twin River Drive, Oakdale

282 Belvedere Drive, Oakdale
$1,349,999
4 Beds ⋅ 4 Baths ⋅ 1030925 MLS
Welcome to 282 Belvedere Drive, an exceptional South Oakdale residence offering breathtaking, unobstructed views of the Great South Bay, Connetquot River, and protected wetlands. Thoughtfully designed to capture the beauty of its surroundings, this 4-bedroom, 3 full and 1 half-bath home combines spacious living, quality craftsmanship, and a truly one-of-a-kind setting. Hardwood floors flow throughout the home, while the open and inviting floor plan is ideal for both everyday living and entertaining. At the heart of the home is a chef's kitchen featuring granite countertops, abundant cabinetry, and generous workspace, seamlessly connecting to the main living areas anchored by a stunning double-sided fireplace that creates warmth and ambiance from multiple rooms. The versatile floor plan includes a spacious primary suite on the second floor, along with a junior primary suite on the main level complete with its own ensuite bath—perfect for guests, extended family, or multigenerational living. Designed to take full advantage of the spectacular scenery, the second floor features an inviting lounge and wet bar area with one of two staircases providing direct access, making it an ideal space for entertaining or relaxing while enjoying the ever-changing waterfront landscape. Two private balconies on the second floor and a full composite deck on the main level provide multiple outdoor living spaces to take in stunning sunrises, sunsets, and the peaceful natural surroundings. While not directly waterfront, this home includes the rare benefit of 100 feet of deeded bulkhead on a protected canal located just approximately 350 feet from the property, offering convenient dockage for up to 3+ boats and easy access to the Great South Bay for boating enthusiasts. Additional highlights include an oversized two-car garage with additional attic storage, central air conditioning, propane heating, owned solar panels, two staircases, and a walk-in attic providing exceptional storage space. Perfectly situated in the highly desirable South Oakdale community with Idle Hour Elementary School, this home offers the best of coastal living with panoramic water views, protected natural surroundings, and outstanding boating access. A rare opportunity to own a truly distinctive property where every day begins and ends with some of the South Shore's most spectacular scenery.

282 Belvedere Drive, Oakdale

282 Vanderbilt Boulevard, Oakdale
$925,000
4 Beds ⋅ 3 Baths ⋅ 947947 MLS
Introducing 282 Vanderbilt Blvd, Oakdale — a rare pre-sale renovation opportunity in the highly sought-after Idle Hour neighborhood. Set on just under half an acre, this thoughtfully reimagined Colonial-style home is currently under renovation and will feature 4 bedrooms, 3 full bathrooms, and a dedicated home office, blending timeless architecture with modern luxury. Designed for today’s lifestyle, the home offers an open-concept kitchen and dining area, ideal for entertaining, along with a spacious living room with fireplace, a separate den, and a bright Florida room that extends the living space year-round. The primary bedroom suite serves as a private retreat, complete with a large closet and a luxurious en-suite bathroom. This comprehensive renovation includes all new utilities and a brand-new roof, providing peace of mind and long-term value for the next owner. Offered pre-sale, the property allows for the opportunity to select custom finishes prior to completion. Please note: photos of finished kitchens and bathrooms are from our builder’s previous projects and are included to showcase the exceptional quality, craftsmanship, and attention to detail that will be delivered upon completion, not the home’s current condition. Located in one of Oakdale’s most prestigious communities and surrounded by beautiful homes, this is a rare chance to secure a fully renovated Colonial in Idle Hour — opportunities like this are limited and will not last.

282 Vanderbilt Boulevard, Oakdale

136 Vanderbilt Boulevard, Oakdale
$899,999
5 Beds ⋅ 3 Baths ⋅ 1044108 MLS
Welcome to 136 Vanderbilt Boulevard, a beautifully updated 3,130 sq. ft. home ideally located in Oakdale’s highly desirable Idle Hour community. Offering five spacious bedrooms and three full baths, this home features an open-concept layout with an easy flow between the living room, dining room, kitchen and family room—perfect for everyday living and entertaining. The family room features a fireplace, while the primary bedroom offers a private en-suite bath. Wood flooring, fresh paint throughout and newly replaced light fixtures create a bright, refreshed feel. The kitchen includes a brand-new Café oven and dishwasher, while additional features include central air, three heating zones, a recent natural gas conversion and a basement with laundry and ample storage. Outside, the backyard has been completely transformed within the past year into a private resort-style retreat with a heated saltwater in-ground pool, extensive pavers and wrought iron fencing. All permits and Certificates of Occupancy are current and up to date. Located in historic Idle Hour, this home is close to Vanderbilt Wharf Marina, nearby waterfront destinations and offers the opportunity for membership at the Idle Hour Beach Club. With over 3,100 sq. ft. of living space, extensive recent updates and an exceptional outdoor setting, 136 Vanderbilt Boulevard offers space, comfort and the best of South Shore living.

136 Vanderbilt Boulevard, Oakdale

162 Stuyvesant Road, Oakdale
$889,000
4 Beds ⋅ 3 Baths ⋅ 1040672 MLS
Welcome to this meticulously renovated home, FEATURING A 1 BEDROOM LEGAL ACCESSORY APT, perfect for RENTAL INCOME or family needs. Also offering the perfect blend of modern, move-in finishes and exceptional indoor-outdoor living. Nestled on a tree lined dead end street in the highly sought-after South Oakdale. Enter inside to discover a bright open floor plan designed for everyday comfort and entertaining. Just off the kitchen is your sprawling deck and lower-level patio pavers overlooking your beautiful fenced backyard. Great for recreation, dining, and entertaining. Byron Lake Park is just down the street. Easy access to restaurants, shopping, beaches, and everything the South Shore has to offer. NY State Star Rebate for taxes is $840.00

162 Stuyvesant Road, Oakdale

517 Ocean Avenue, Oakdale
$849,000
4 Beds ⋅ 2 Baths ⋅ 1025588 MLS
Beautiful 4 Bedroom 2 Full Bath Ranch offering an open and inviting floor plan perfect for entertaining. The custom Kitchen features vaulted ceilings, cherry wood cabinetry, granite countertop, tiled backsplash, stainless Steel Appliances and a wood burning stove that opens up to a spectacular Great Room with soaring vaulted been ceiling, a stunning stone accent wall, abundant natural light, a gas fireplace, and a wet bar. The Formal Dining room is enhanced with crown molding. Convenient mudroom off the attached 2 car garage. The full bright basement is partially finished and offers a living room/playroom, full bathroom, laundry room, utility/storage area, and an outside entrance. Enjoy the beautiful professionally landscaped front and backyard featuring a paver front stoop and walkway. rear paver patio, and private deck off primary bedroom, Flower perennial garden, Gazebo and a storage Shed. Wood flooring and luxury laminate throughout main level. Anderson windows throughout (except two Pella windows). Additional features include gas heat/cooking, 200-amp electric service and precast cesspools. A truly exceptional home offering comfort, quality craftmanship, and outstanding indoor and outdoor living.

517 Ocean Avenue, Oakdale

103 Bonnie Road, Oakdale
$774,999
4 Beds ⋅ 2 Baths ⋅ 1028002 MLS
Welcome to 103 Bonnie Road in Oakdale! This beautifully renovated split-level home offers the perfect blend of modern, move-in-ready finishes and exceptional indoor-outdoor living. Featuring four thoughtfully designed levels, the home includes three spacious bedrooms and a full bathroom on the upper level. The main living level boasts an open-concept layout with vaulted ceilings, a bright and inviting living/dining room, and a spacious kitchen ideal for everyday living and entertaining. Sliding glass doors lead to a large rear deck overlooking the expansive backyard. The lower level offers outstanding flexibility with a converted bedroom, additional living area, kitchenette, full bathroom, and a separate outside entrance—ideal for extended family, guests, a home office, or potential accessory living space (subject to local regulations). The unfinished basement provides abundant storage and houses the home's utilities. Additional highlights include 150-amp electric service, brand-new central air conditioning, LED high-hat lighting throughout the bedrooms and living areas, and a newly paved double-wide driveway. Situated on a generous quarter-acre lot, the property offers plenty of room for entertaining, recreation, or future outdoor enhancements. Conveniently located just minutes from the waterfront and vibrant downtown Sayville, you'll enjoy easy access to restaurants, bars, cafe's, shopping, parks, and everything the South Shore lifestyle has to offer.

103 Bonnie Road, Oakdale

19 Meadow Court, Oakdale
$760,000
2 Beds ⋅ 3 Baths ⋅ 1018249 MLS
Welcome to effortless living in this beautifully maintained townhouse-style residence located within a desirable 55+ gated community in the heart of Oakdale. Offering a spacious layout, attached one-car garage, and thoughtful design throughout, this turnkey home perfectly blends comfort, convenience, and style. A dramatic two-story entry immediately welcomes you with soaring ceilings, hardwood floors, an elegant dining area with chandelier, and a beautiful view of the second-floor overlook above. The open-concept layout continues into a spacious living room featuring a gas fireplace and seamless flow into the kitchen. The well-appointed kitchen offers cherry cabinetry, granite countertops, stainless steel appliances, countertop seating, and an additional dining area overlooking the private patio and beautifully maintained grounds. A generously sized powder room completes the main level. Access the second floor by either the staircase or the custom raised wood-panel elevator, providing convenient access to all levels of the home, including the basement. Upstairs, a spacious landing overlooks the dining area below and leads to the primary suite featuring multiple closets, a built-in vanity area with mirror, and a private bathroom complete with dual sinks and a large walk-in shower with bench seating. An additional guest bedroom and full guest bathroom provide comfortable accommodations for family and visitors. The lower level offers additional finished living space with an electric fireplace and a flexible area currently used as a home gym. The unfinished portion provides an abundance of clean storage space, a laundry center, and an egress window, creating endless possibilities. Perfectly positioned within the community, residents enjoy a picturesque setting featuring a gated entrance, beautifully landscaped grounds, a tranquil pond with fountain, and a welcoming clubhouse with fireplace for events and gatherings. Conveniently located near Sunrise Highway, shopping, dining, and everyday amenities. Exceptionally maintained, thoughtfully designed, and truly move-in ready — this Oakdale residence offers the ease of 55+ community living in a warm and inviting setting.

19 Meadow Court, Oakdale

87 Wexford Drive, Oakdale
$750,000
4 Beds ⋅ 2 Baths ⋅ 1046548 MLS
Set midblock on a third of an acre, this open-concept Colonial spreads 1,909 square feet across seven rooms. The eat-in kitchen stretches to island seating, with granite counters, stainless appliances and pantry storage. A wood burning stove anchors the living room, and the family room opens through patio doors to a fenced backyard. Four bedrooms include a primary with double closets and its own bathroom entry, and oak floors carry through the home. Behind the finishes: 200-amp generator-ready service, smart thermostats, ENERGY STAR appliances, double-pane windows, an entrance foyer, attached garage, private driveway, and sprinklers front and rear. Two state parks, the Bayard Cutting Arboretum, the train station, shops, and downtown and waterfront dining are all close by.

87 Wexford Drive, Oakdale

22 Meadow Court, Oakdale
$729,000
2 Beds ⋅ 3 Baths ⋅ 1029383 MLS
Desirable END UNIT beautifully maintained ,located in a desirable 55+ gated community in Locust Cove. Enjoy the convenience of an elevator with access from the basement to the second floor. This spacious home features a formal dining room, a warm and inviting family room with a gas fireplace, and eat-in kitchen with granite countertops and sliding doors leading to a private patio with awning -perfect for relaxing and entertaining. The primary bedroom offers a comfortable retreat with an en-suite bath, vanity, double sink, shower with built in seat closets with organizers Additional highlights include wood floors, central air, attic stairs, laundry on the second floor, alarm, lots of basement storage and built ins, garage with entry to home and epoxy flooring, soft garage door. and abundant community amenities that enhance an easy, low maintenance lifestyle.

22 Meadow Court, Oakdale

100 Middlesex Avenue, Oakdale
$699,999
4 Beds ⋅ 2 Baths ⋅ 1030335 MLS
Welcome To This Well Cared For Idle Hour Colonial Situated On A Large Corner Property! Greeted By A Gorgeous Foyer Leading To A Formal Living Room & Formal Dining Room w/Hardwood Floors Throughout. The Eat-In Kitchen Features Wide Plank Tile Flooring, Light Maple Cabinetry, Granite Countertops, Recessed Lighting, Stainless Steel Refrigerator & Microwave, Electric Cooking, Dishwasher & Center Island w/Granite Top. The Main Level Also Features A Stone Faced Fireplace w/Granite Mantle, 4 Year Young Laundry/Mudroom, Half Bath & Andersen Sliders Leading To The Deck w/Beautiful Views Of The Wetlands. Upstairs You'll Find 4 Bedrooms & A Full Bath w/Jacuzzi Tub. Additional Features Include Oil Heat, Gas Is In The Street, CAC, 200-Amp Electrical Service w/Transfer Switch for Generator, Immaculate Attached 2-Car Garage w/Attic Storage, Deck w/Gazebo, 8-Zone IG Sprinklers, Mature Landscaping, 3 Year Young Self Contained Septic System, Water Main Replaced & Expansion Tank Installed In 2026. This Home Has Been So Loved & Is Ready For It's Next Owner!

100 Middlesex Avenue, Oakdale

7 Daria Drive, Oakdale
$599,000
2 Beds ⋅ 2 Baths ⋅ 1021064 MLS
Welcome to 7 Daria Dr. Oakdale, NY — Windmill Gate 55+ Community, low-maintenance 55+ community of just 110 homes, built between 1989 and 1991. This Ashley Model has a Full Basement (only 11 homes built with a basement) Here you’ll find a wonderful blend of privacy, amenities, and community spirit in East Long Island. This inviting 2-bedroom, 2-bath ranch includes the signature features you’d expect in Windmill Gate — vaulted ceilings, bright spaces, and a 1-car attached garage. The home’s living room is illuminated by a beautiful skylight, enhancing the open, airy feeling. The layout flows into a formal dining area and a well-equipped kitchen with abundant cabinetry. The primary suite boasts an en-suite bath and generous closet space, while the second bedroom is ideal for guests or a cozy home office. Additional comforts include central air, in-home laundry, and a private patio for relaxing or entertaining outdoors without maintenance worries. As a resident of Windmill Gate, you have access to a clubhouse / amenity center that features a fitness room, billiards, multipurpose and meeting rooms, sauna / steam rooms, and outdoor pool, patio, and gazebo. This is a community built for connection — neighbors gather regularly for social events, clubs, and casual afternoons by the pool. Located just moments from Nicoll Bay and Heckscher State Park, and minutes from local dining, shopping on Sunrise Highway, and Long Island MacArthur Airport (˜12 minutes), Windmill Gate also offers good access to NYC for day trips or commuting. Don’t miss the chance to live in this rare gem — schedule your private tour today and experience the charm and lifestyle of Windmill Gate.

7 Daria Drive, Oakdale

28 Academy Lane, Oakdale
$579,000
2 Beds ⋅ 2 Baths ⋅ 1047899 MLS
Beautifully updated 2 bedroom ranch with the potential for a 3rd bedroom, offering 2 full baths and a bright, inviting interior. Hardwood floors, custom moldings, recessed lighting, and two skylights add warmth and character throughout. The updated kitchen features granite countertops, stainless-steel appliances, and a glass tile backsplash, while the living room and dining room provide comfortable spaces for everyday living. A huge walk-in closet with a custom organizing system offers exceptional storage. Additional features include central air conditioning, gas hot-air heat, updated windows, and vinyl siding. Outside, enjoy professional landscaping, a private backyard with vinyl fencing, and a paver patio perfect for relaxing or entertaining, and a detached garage offering additional parking and storage. All this, plus taxes of only $9,644.14 after the Basic Star rebate. Low maintenance, low taxes, low utilities…low bills! A true must see.

28 Academy Lane, Oakdale

2310 Wilshire Lane Unit #2310, Oakdale
$349,000
1 Beds ⋅ 1 Baths ⋅ 1047664 MLS
Beautifully updated and truly move-in ready, this spacious one-bedroom, one-bath ground-floor co-op in Birchwood on the Green offers comfortable, easy living in a desirable location within the community. The bright and inviting interior features gleaming hardwood floors, a generous open living and dining area, an updated kitchen with stainless steel appliances, and a beautifully renovated bath. The oversized bedroom offers plenty of space, while the private covered patio provides a lovely spot to relax outdoors. Conveniently located within the community with easy access to parking and surrounding amenities. Monthly maintenance includes heat, water, landscaping, exterior maintenance and snow removal. A meticulously maintained home with thoughtful updates throughout—just unpack and enjoy.

2310 Wilshire Lane Unit #2310, Oakdale

4715 Wilshire Lane Unit #K15, Oakdale
$219,998
1 Beds ⋅ 1 Baths ⋅ 1043826 MLS
Charming One-Bedroom Co-op in Birchwood on the Green Welcome to this beautifully updated one-bedroom, one-bathroom co-op nestled within the desirable courtyard setting of Birchwood on the Green. This spacious home offers a comfortable, flexible layout with an open-concept living and dining area, oversized windows, and an abundance of natural light. The efficient kitchen features a convenient pass-through that could also serve as a cozy breakfast nook, along with newly installed stainless-steel appliances. Beautiful oak hardwood floors, completed within the past year, complement the recessed lighting and create a sleek, modern feel throughout the living space. The inviting bedroom comfortably accommodates two and offers two generously sized closets for excellent storage. A newly installed smart Wi-Fi-enabled wall AC unit adds year-round convenience and comfort. Residents also enjoy the convenience of a laundry room located just below the unit, as well as ample basement storage shared among the owners in the building. This move-in-ready home is an excellent opportunity for those looking to own or invest in Birchwood on the Green. Simply unpack, settle in, and start enjoying all this welcoming co-op has to offer. Pets are welcome with board approval.

4715 Wilshire Lane Unit #K15, Oakdale

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