Oakdale Real Estate

Welcome to Oakdale, New York – a hidden gem nestled in the heart of Suffolk County. This charming hamlet, situated along the picturesque shores of the Great South Bay, offers a unique blend of suburban tranquility and vibrant community life. With its rich history dating back to the 19th century, Oakdale is not only known for its scenic beauty but also for its warm, welcoming atmosphere that makes it a perfect place to call home.

As you stroll through Oakdale, you'll discover a delightful mix of historic architecture and modern conveniences. The hamlet boasts an array of local shops, cozy cafes, and restaurants that cater to every palate. Enjoy a leisurely afternoon at the nearby Connetquot River State Park Preserve, where nature enthusiasts can explore miles of hiking trails, fish in pristine waters, or simply relax amidst the serene surroundings.

Families will appreciate Oakdale's excellent school system, which is part of the Islip School District, ensuring that children receive a quality education in a nurturing environment. The community is also known for its strong sense of camaraderie, with numerous events and activities that foster connections among residents.

For those who commute, Oakdale offers convenient access to the Long Island Rail Road, making it easy to reach New York City while returning home to the peaceful charm of this idyllic hamlet. Whether you're drawn by the natural beauty, the rich history, or the warm community spirit, Oakdale is a wonderful place to explore and discover your next home. Come and experience the magic of Oakdale, where every day feels like a retreat!

Newest Listings in 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

$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

$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

$429,000

2 Beds ⋅ 1 Baths ⋅ 1028527 MLS

Beautiful 2nd floor coop in the Desirable Birchwood on the Green. Move right in to this beautifully updated 2-bedroom 2nd floor coop. The updated kitchen features a pass-thru to the dining room/living room creating an open and inviting feel. The tastefully renovated bathroom, fresh paint, and new Hunter Douglas blinds/shades adds modern feel throughout. Gleaming natural hardwood floors, large closets and outdoor balcony. This is a Must See..

4425 Wilshire Unit #4425, 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

$333,000

1 Beds ⋅ 1 Baths ⋅ 1024057 MLS

O!K! Here's your chance to grab a Super Affordable Co Op Corner Space! ~ in the Classic Birchwood on the Green Enclave of Oakdale! Easy Living close to the LIRR, Banks. Deli's, Restaurants and More ! This Bright Corner Unit is Ready for Your Own Personal Touch. One Large Bedroom with windows on two sides. Two Large Closets in the Bedroom and Two Large Closets in the Livingroom. One is able to be used as a washer/dryer closet! Living room is also Large with Sliding Doors leading to the Private Patio area. Hang out and Enjoy the Birds! Additional Storage Available

3922 Wilshire Lane Unit #H, 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

$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

$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

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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.