Oakdale Real Estate Search

Oakdale 5 Bedroom Properties for Sale

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Newest Oakdale 5 Bedroom Homes and Condos for Sale

$1,199,990
5 Beds ⋅ 4 Baths ⋅ 1048277 MLS
Welcome to 124 Bayview Drive, a spacious and versatile Colonial nestled in desirable south Oakdale within highly regarded Connetquot School District. Set on over half an acre, street-to-street property, this 5-bedroom, 3.5-bath home offers approximately 3,000 square feet of living space, exceptional amenities, and room for extended family or separate office space. The home features a thoughtfully designed extension with an additional bedroom, full bathroom, living space, additional room, and separate exterior entrance—ideal for guests, extended family, a home office or more. Throughout the home, you'll find beautiful 3/4" oak flooring, stainless steel appliances, Andersen windows, vinyl siding, upgraded 200-amp electric, oil heat, wood burning fireplace, jetted tub in the upstairs bathroom and central air conditioning. The spacious primary suite includes an en-suite bathroom. Car enthusiasts and hobbyists will appreciate the incredible garage space, including a 16' x 20' attached two-car garage and an impressive 20' x 23' detached two-car garage. The detached garage offers endless possibilities for a workshop, studio or recreation space, with abundant storage above both garages. Step outside and discover your own private retreat. The rear of the home features a screened porch and deck overlooking the 16' x 32' inground pool surrounded by a spacious paver patio. Mature landscaping and inground sprinklers create a lush, private setting perfect for entertaining, relaxing, and enjoying summer days at home. This street-to-street lot also provides access to a dead-end block behind the property, adding privacy and versatility. Partial waterviews can be enjoyed during the winter months. Located in Flood Zone X, this property does not require flood insurance. Just steps from Byron Lake and minutes from Oakdale's renowned marinas and waterfront restaurants, the Oakdale LIRR station, and the shopping and dining of nearby Sayville, this home combines space, flexibility, and an enviable South Shore lifestyle. With its generous living space, unique extension, resort-style backyard, four-car garage capacity, and prime location, 124 Bayview Drive is a rare opportunity to create the home you've been looking for!

124 Bayview 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
$3,999,900
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
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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.