Oakdale Homes for Sale

Welcome to Oakdale, New York – a hidden gem nestled in the heart of Suffolk County! This charming waterfront community, situated along the picturesque banks of the Great South Bay, offers a perfect blend of suburban tranquility and vibrant coastal living. Known for its rich history and stunning natural beauty, Oakdale is a haven for families, retirees, and anyone seeking a serene lifestyle just a stone's throw from the hustle and bustle of New York City.

As you explore the enchanting streets of Oakdale, you’ll be captivated by its beautiful tree-lined neighborhoods, friendly atmosphere, and a strong sense of community. The area boasts an array of recreational opportunities, from boating and fishing to hiking and biking along scenic trails. With its close proximity to the Long Island Rail Road, commuting to Manhattan for work or leisure is a breeze.

For those considering making Oakdale their home, the real estate market is thriving with a diverse selection of homes for sale. Whether you’re in search of a cozy bungalow, a spacious family residence, or a luxurious waterfront property, Oakdale has something to suit every taste and budget. Many homes feature stunning views, modern amenities, and easy access to local parks, schools, and shopping centers.

Don’t miss the opportunity to discover your dream home in this idyllic community. With its charming character and welcoming spirit, Oakdale is not just a place to live – it’s a place to thrive. Explore our listings today and take the first step toward your new life in Oakdale!

Newest Oakdale Homes for Sale

$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

$1,595,000

3 Beds ⋅ 3 Baths ⋅ 1024343 MLS

One-of-a-Kind Ranch Home with 2,692/3,200 Square Feet Located in the Historic Idle Hour Artist Colony Subdivision of Oakdale South of Montauk Highway. Situated on a Private .67 Acre Landscaped Parcel with a Heated Gunite Inground Pool, Surrounding Tiled Patio, and Custom Sauna. Enter onto the Covered Front Porch into a Hallway with Cathedral Ceiling into the Living Room with Front and Rear Double Sliding Doors, 24 Skylights and Tiled Floor. Den/Dining Room/4th Bedroom with Stained Glass Windows, Full Bath with Shower with Radiant Heated Floor and Laundry Area, into the Custom Kitchen with 18 Foot Ceiling, 2 Sinks, Refrigerator and Freezer, 2 Dishwashers, Island to Seat 6 and Sliding Doors to Backyard. Hallway Full Bath with Tub and Radiant Heated Floor, 2 Bedrooms with Double Closets, and Sitting Room with 2 Sets of Double Closets for Office or Gym into the Primary Bedroom with Sliding Doors Out to a 2nd Front Porch, Walk-In Closet and Full Bath with Radiant Heated Floor, Skylight and Shower. 2-Car Attached Garage with Interior Access. Navian Gas Hot Air Heating System, 200 Amp Electric, Generator, 2 Sheds and Inground Sprinklers. Too Much to List!

21 Princess, 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

$1,299,990

4 Beds ⋅ 3 Baths ⋅ 1025608 MLS

Welcome home to your private retreat on this quiet cul-de-sac in Oakdale, NY! This recently renovated 20 year young colonial is set on an expansive 1.3 acre lot and is located in desirable Connetquot School District. This home features 4 bedroom, 2.5-bathrooms and over 3,000 sq ft of living space including a partially finished basement and 2 car garage. The eat-in kitchen has been updated with modern finishes including white cabinets, stainless steel appliances, gas range, quartz countertops and an attached laundry room for convenience. This home has 3/4 inch hardwood oak floors and recessing lighting throughout and is freshly painted. Andersen windows are accented by custom plantation shutters in every room. The first floor is completed by a dining room with chair rail molding, den with gas fireplace, a formal living room and half bathroom. Moving upstairs, the primary en-suite has cathedral ceilings, generous walk-in closets and an oversized private bathroom with jetted tub. Three additional bedrooms and a shared hallway bathroom round out the upstairs. There is also a partially finished basement with unlimited possibilities. The backyard is what really separates this home with a custom shaped heated saltwater pool with attached spillover spa surrounded by well maintained pavers. The gazebo and pool house with bonus features make this the perfect space for entertaining! There is also a large deck with awning overlooking the perfectly manicured lawn that has inground sprinklers in both the front and back yards. Additional features include natural gas heat, fully owned solar panels, central air conditioning, and 200 amp electric. Located a short distance to Connetquot State Park, Sunrise Hwy and Oakdale train station for commuting, as well as the restaurants and marinas along the Connetquot River, this home is perfectly positioned to turn your dream home into a reality!

15 Victoria Court, Oakdale

$749,000

3 Beds ⋅ 2 Baths ⋅ 1021139 MLS

Welcome to this beautifully renovated split-level home nestled on an oversized 0.47-acre property in the heart of Oakdale. Completely updated from top to bottom, this move-in ready residence offers 3 spacious bedrooms, 2 full bathrooms, and approximately 1,850 square feet of thoughtfully designed living space. The open-concept layout features a bright living area, an updated kitchen, and modern finishes throughout, creating the perfect setting for both everyday living and entertaining. The flexible split-level design provides additional living space ideal for a family room, home office, or recreation area. Enjoy central air conditioning, natural gas heating, and the convenience of a full finished basement offering even more usable space. Outside, the expansive backyard provides endless possibilities for outdoor entertaining, recreation, or future enhancements. Conveniently located near parks, shopping, dining, major roadways, and all that Oakdale has to offer. A rare opportunity to own a turnkey home on an oversized lot—don't miss it!

566 Locust Avenue, 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

$1,464,999

4 Beds ⋅ 3 Baths ⋅ 1013434 MLS

COMING SOON! Located in one of Oakdale's most desirable neighborhoods, this stunning NEW CONSTRUCTION offers 3,400 sq. ft. of thoughtfully designed living space just minutes from the Connetquot River, local marinas, and many of the top waterfront restaurants on the South Shore! Featuring 4 bedrooms, 2.5 baths, this TURNKEY home will showcase quality craftsmanship, high-end finishes, and an OPEN-CONCEPT layout designed. The FULLY LANDSCAPED property will include a fenced in, private outdoor space, an IN-GROUND POOL and custom paver patios/walkways, perfect for entertaining and relaxation. A rare opportunity to own a BRAND NEW, MOVE-IN READY home in a prime South Shore location. EXPECTED COMPLETION, 8/1/2026. More details coming soon!

Bellevue Road, 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

$779,000

2 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 2-bedroom, 1.5-bath Colonial offers a rare blend of bohemian history and modern tranquility. The second bedroom is currently the living room, but will be converted back at the seller's expense. 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

$475,000

4 Beds ⋅ 3 Baths ⋅ 980770 MLS

Rare opportunity to own a piece of history in the historic district of Oakdale. This single family home was once part of the former Vanderbilt Grounds, known as the Artist Colony. With original timbers and finishes, as well as modern conveniences, this home offers the best of both worlds. Features include wide planked hardwood floors, built-in cabinetry, original door and window hardware, and an updated kitchen with stainless appliances. With plenty of space for a home office and more, this home is perfect for those looking for room to spread out. Enjoy the convenience of being near shopping, restaurants, parks, the river, marinas

17 Jade Street, Oakdale

Start Your Search

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.