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$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
$1,195,000
4 Beds ⋅ 4 Baths ⋅ 1044054 MLS
Stunning Idle Hour Colonial with breathtaking views of Connetquot River! Updated 3 story colonial with hardwood floors, quartz countertops, 4 bedrooms, includes full house alarm system, built in stereo system and on a huge property fully fenced backyard which provides endless possibilities for outdoor enjoyment!

406 Vanderbilt Boulevard, 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
$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
$768,000
3 Beds ⋅ 3 Baths ⋅ 1037713 MLS
Presenting a Rare Opportunity to own a Fully Renovated 2,705sqft Colonial with a Detached One-Bedroom Cottage and Additional Bonus Structure, situated on a 16,117sqft lot in Highly Desirable Oakdale. This property is Move-In Ready with Extensive Interior and Exterior Renovations Completed between 2023 and 2026. The Main Residence Features 3 bedrooms, 2.5 bathrooms, and a Spacious Layout. The First Floor Primary Bedroom offers a Private En-Suite Bathroom, Generous Closet Space, and Access to a Versatile Attic that can be Converted Back into a Loft. Additional Highlights include a 6 Car Driveway and an Unfinished Basement for Storage and Utility Access. The Detached Cottage consists of 1 Bedroom, 1 Full Bathroom, Kitchen, Living Room, and its own Separate Utilities. The Cottage Offers potential for Extended Family, Guests, or Rental Income (subject to proper permits). A Separate Bonus Structure adds even more flexibility, Complete with Connected Electricity and its own Patio Area. Both the Front and Backyard have been Completely Transformed with Landscaped Lawns, New Rock Pathways, Thoughtfully Designed Garden Areas, and New Plantings. Conveniently Located near Schools, Shopping, Dining, Parks, Transportation, and Major Roadways. Whether you're seeking a Flexible Primary Residence, Multigenerational Living Arrangement, or Rental Income Potential, this property is an Exceptional Opportunity.

1116 Montauk Highway, 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
$899,000
5 Beds ⋅ 3 Baths ⋅ 1039743 MLS
New Listing in South Oakdale’s Vanderbilt Section! Welcome to this beautifully updated and upgraded Colonial, perfectly situated in one of South Oakdale’s most desirable neighborhoods. Thoughtfully improved and meticulously maintained, this home is truly ready for its new owners to move right in and start enjoying everything it has to offer. From the moment you step inside, gorgeous hardwood floors and elegant crown molding set the tone throughout the home. The spacious chef’s eat-in kitchen offers plenty of room for cooking, gathering, and entertaining and flows beautifully into the inviting den with a fireplace. A formal living room with soaring ceilings adds another impressive space for entertaining. Upstairs, the primary bedroom ensuite is your own private retreat, featuring a full bath and walk-in closet. Four additional generously sized guest bedrooms and a second full bath provide plenty of space for guests or a home office. The home also features a partial basement and two-car garage, offering additional storage and convenience. But wait until you step outside! This backyard was made for the staycation lifestyle. Fully fenced with PVC fencing, the property features a beautiful inground pool surrounded by a patio and deck, creating the perfect setting for summer entertaining, weekend barbecues, or simply relaxing poolside without ever leaving home. Updated, spacious, and designed for both indoor and outdoor living, this South Oakdale Colonial has everything you’ve been waiting for. Your next chapter starts here. Welcome home!

165 Pepperidge Road, Oakdale
$4,499,900
5 Beds ⋅ 5 Baths ⋅ 1029824 MLS
SUMMERWIND – An Extraordinary Waterfront Estate on the Connetquot River. Welcome to Summerwind, one of Oakdale’s most distinguished waterfront estates. Privately set behind stone gates on 1.09 beautifully landscaped acres, this custom-built residence offers approximately 6,286 square feet of luxurious living space, 200 feet of Connetquot River frontage, and a 150-foot private deep-water dock with float and direct access to the Great South Bay, Fire Island, and the Atlantic Ocean. Built in 2004 with exceptional craftsmanship, this three-story brick Colonial showcases Brazilian cherry hardwood floors, handcrafted custom millwork including archways & crown moldings, soaring ceilings, crystal chandeliers, wall sconces and timeless architectural details throughout. The gourmet chef’s kitchen features custom cabinetry, expansive granite countertops, premium appliances, pantry with additional refrigerator, and an oversized center island that opens seamlessly to the spectacular Great Room with a coffered ceiling and fireplace. The luxurious primary suite offers a private sitting area with fireplace, spa-inspired bath, his/hers walk-in closet suite has custom dressing room and built-ins with inlaid custom doors and island with marble tops and lighting, laundry shoot from primary bedroom to laundry room and a private balcony overlooking the resort-style backyard and waterfront. Additional guest suites, a formal dining room, music room, executive office, billiards room, home theater, recreation rooms, tremendous amount of closets for storage, a finished 2000 square foot third floor, and a full finished basement with outside entrance provide exceptional space and flexibility, and the outdoor living rivals a private resort with a 48’x 28’ freeform Gunite pool featuring a natural rock waterfall and waterslide, a 10’x14’ pool cabana, expansive covered terraces, natural stone patios, fire pit, professionally landscaped gardens, and a private sports court. Western exposure provides breathtaking sunsets over the Connetquot River. Built to an exceptional standard, the home features 2x6 construction, 600-amp electrical service, 45kw whole-house diesel backup generator, security cameras and alarm, dual-fuel heating (natural gas and oil), six-zone high-efficiency air conditioning, radiant-heated bathroom floors, separate electrical subpanels throughout the home, garage, and cabana, and a 4-inch water service. Situated at an approximate elevation of 11.5 feet in an X Flood Zone, no FEMA flood insurance is currently required. Summerwind is a rare opportunity to own one of Long Island’s premier waterfront estates—where timeless architecture, exceptional engineering, world-class boating, and resort-style living come together in one extraordinary property. A legacy estate unlike any other.

608 Shore 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
$899,990
4 Beds ⋅ 5 Baths ⋅ 1018752 MLS
Large Colonial in South Oakdale. Amazing location. 4 Brs, 4.5 bths. Sparkling in ground pool, multiple decks on shy half acre property. Fenced yard with in ground sprinklers. Main part of house needs some updating. Amazing opportunity for multi generational living with proper permits. Total living area close to 4000 sq ft. Make this home your own oasis. Don't miss out.

55 Riverview Court, Oakdale
$779,999
4 Beds ⋅ 2 Baths ⋅ 1004296 MLS
Enjoy Beaches, Boating, Restaurants and Water then this is the House for you!! Located South of Montauk Hwy in the Sought-After Idle Hour Community! This Over-Sized High Ranch has a Super Spacious Eat-In Kitchen with Stainless Steel Appliances, Plenty of Cabinetry for Storage and Extra Seating Area, Living Room with Wood-Burning Fireplace and Doors going out to Front Deck, Primary Bedroom w/ Full Bath, Nice Big Den which also has a Wood-Burning Fireplace, Bright & Airy Florida Room with Windows Galore going out to Large Deck and Patio Area, Natural Gas Heat, Hardwood Floors Throughout, In-Ground Sprinklers and So Much More!! Don't Miss!

661 Shore Drive, Oakdale
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 1000816 MLS
Welcome to waterfront living at its finest. Situated in historical Idle Hour on a private road. No Flood Ins. required.!!No neighbors across the street because of the Arboretum. This home sits a beautiful canal-front, this spacious and meticulously maintained 5 bedroom home offers the perfect bled of comfort, boating lifestyle, and flexible living space for extended family. a 3 yr old dock this exceptional property is ideal for the boating enthusiasts with ample room for large vessels and convenient canal access. There are no bridges straight shot to the bay. The bulkhead dock is 90/100 ft. Sellers have had throughout the yrs. not all at the same time, 39 ft. Searay, a 27 Ft .activator, 37 Ft Silverton, 34 Ft. Silverton, 27 ft. Cigarette. There is also a boat ramp. The expansive backyard, paired with the two-level deck overlooking the water, creates the perfect setting for entertaining, outdoor dining or simply relaxing while enjoying serene views. Inside, you'll find versatile layout with generous living space, radiant heating kitchen/dining room floors, downstairs a large family room with a cozy fireplace perfect for gatherings yr. round. Laundry room. A second kitchen for convenience, designed with comfort and functionality in mind, the layout easily accommodates extended family. Spacious two-car garage, oversized driveway, beautifully manicured landscaping and exceptional curb appeal from front to back. A rare opportunity to own a turn-key waterfront retreat offering space, functionality and ultimate coastal lifestyle.

24 Biltmore Avenue Extension, Oakdale
$759,000
1 Beds ⋅ 2 Baths ⋅ 992058 MLS
Step into a world of timeless charm and waterfront luxury. Located in the coveted Idle Hour Artist Colony of South Oakdale—originally part of William K. Vanderbilt’s 900-acre Gilded Age estate. This unique 1-bedroom, 1.5-bath Colonial offers a rare blend of bohemian history and modern tranquility. There is potential for a second bedroom by converting the living room, AI generated picture show what it would potentially look like. Sellers are willing to add the wall if buyers would like to convert the living room into a bedroom. This property is a boater dream, enjoy unparalleled canal access with an impressive 150-foot bulkhead, perfect for docking multiple vessels or simply taking in the serene water views. Nestled among the unique, storybook homes of the Artist Colony, this residence reflects the neighborhood's unique architectural heritage, once home to creative minds and historic stables. Situated on a quiet, narrow street in a protected historical district, you are just minutes from local favorites like the Snapper Inn, Mannino's Italian Restaurant and Bayard Cutting Arboretum, with easy access to the LIRR for a seamless commute. This property is a "must-see" gem in one of Long Island’s most enchanting hidden communities.

70 Featherbed Lane, Oakdale
$225,000
973848 MLS
Virgin land

landlocked pcl, Oakdale
$824,990
3 Beds ⋅ 2 Baths ⋅ 924569 MLS
Oakdale's exclusive, private & beautiful Vanderbilt Estate Idle Hour historic community. This wideline Hi Ranch has hardwood flooring, large Formal dining, a rear deck & a remodeled 1st floor with a large rear extension. Very nice 100' by 197' landscaped property, inground sprinklers & a detached garage. All hookups for an accessory apartment are in place. A great home in a beautiful setting & highly desitrable area...

59 Edgewood Avenue, Oakdale

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.