Oakdale Homes with Pool

Welcome to Oakdale, New York, a hidden gem nestled in the heart of Suffolk County. This charming community, located along the picturesque banks of the Great South Bay, offers a unique blend of suburban tranquility and vibrant coastal living. With its lush landscapes, rich history, and friendly neighborhoods, Oakdale provides an ideal setting for families, retirees, and anyone seeking a peaceful retreat just a stone's throw from the bustling energy of Long Island.

One of the standout features of Oakdale is its stunning selection of homes, many of which boast luxurious pools, perfect for those warm summer days. Imagine lounging by your own private oasis, sipping a cool drink while soaking up the sun, or hosting memorable gatherings with family and friends around your sparkling pool. These homes are designed for both relaxation and entertainment, making them perfect for anyone looking to embrace the outdoor lifestyle.

In addition to the beautiful residences, Oakdale is conveniently located near a variety of recreational activities. Explore the nearby waterfront parks, enjoy a day of fishing, or take a scenic boat ride along the bay. The community also offers easy access to shopping, dining, and cultural attractions, ensuring that you have everything you need right at your fingertips.

Whether you’re searching for a cozy family home or a spacious retreat, Oakdale’s homes with pools provide the perfect blend of comfort and luxury. Discover the charm of this delightful town and find your dream home in Oakdale today!

Newest Oakdale Homes with Pool

$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

$1,595,000

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

$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

$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

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.