Oakdale Homes for Sale

Welcome to Oakdale, a hidden gem nestled in the heart of Suffolk County, New York. This charming hamlet, located along the picturesque banks of the Great South Bay, offers a perfect blend of suburban tranquility and vibrant community life. With its rich history dating back to the 19th century, Oakdale boasts a unique character that captivates residents and visitors alike. The area is known for its lush green spaces, scenic waterfront views, and friendly neighborhoods, making it an ideal place for families and individuals seeking a peaceful retreat from the hustle and bustle of city life.

Oakdale is not just about its serene landscapes; it also offers a plethora of recreational opportunities. Enjoy leisurely walks along the picturesque waterfront, indulge in water sports, or explore the nearby parks that provide ample space for outdoor activities. The community is well-connected, with easy access to major highways and the Long Island Rail Road, making it a convenient location for commuters heading to New York City.

For those looking to make Oakdale their home, the real estate market is thriving with a diverse array of homes for sale. From charming single-family residences to modern townhouses, there’s something to suit every taste and budget. Many properties feature spacious yards, updated interiors, and proximity to local amenities, including shops, restaurants, and schools. Whether you're a first-time homebuyer or looking to upgrade, Oakdale offers an inviting community and a wealth of options to find your perfect home. Embrace the Oakdale lifestyle and discover the enchanting charm of this beautiful hamlet in Suffolk County!

Newest Oakdale Homes for Sale

$2,199,000

5 Beds ⋅ 4 Baths ⋅ 1050358 MLS

Welcome to Osprey Landing — Your Private Waterfront Retreat! Discover the rare opportunity to own 2.2 acres of private waterfront paradise in Oakdale, where expansive water views, exceptional privacy, and a true boater’s lifestyle comes together in one remarkable property. Set on a private peninsula, this 3,800-sq. ft. plus, 5-bedroom, 3.5 bath Colonial offers an ideal blend of space, comfort, and versatility. Open-concept layout creates an inviting flow for both everyday living and entertaining, complemented by an eat-in kitchen with top-of-the-line appliances, den with fireplace/wood burning soapstone stove, living room, and elegant formal dining room. The thoughtfully designed 1st floor also includes a bedroom with a full bath, providing an ideal private in-law, guest, or au-pair suite. Upstairs, the spacious primary suite offers a peaceful retreat with a private ensuite bath, walkout outdoor balcony, and multiple walk-in closets, while additional bedrooms provide flexibility for family, guests, or a home office. Large unfinished third-floor attic offers valuable expansion potential — an opportunity to create additional living space tailored to your vision. Step outside and experience what makes Osprey Landing truly special. The waterfront patio, complete with a built-in kitchen: mini-refrigerator, sink, cabinets, and a gas barbecue, is perfectly positioned to take in tranquil canal views and create unforgettable moments with family and friends seated along the bar or dining table near the hot tub. Follow the steps down to your private dock with water and electric, offering direct access to the protected waterfront. A 15,000lb boat lift and additional second dock is permitted, subject to required approvals. Additional features include 2 sheds and an attached two-car garage with a newly epoxied floor adding storage and convenience. Located within the Connetquot School District and just minutes from the Oakdale LIRR, Sunrise Highway, restaurants, and a South Shore marina, this property combines privacy and waterfront living with convenient access to everything you need. Osprey Landing is more than a home — it is a rare waterfront lifestyle. Private acreage, protected water, boating access, generous living space, and room to create something truly your own make this an opportunity that rarely comes to market. Buyer to independently verify dock permitting and boat-lift requirements with the Town of Islip. All dimensions, square footage, and other property information are approximate and should be independently verified by the buyer.

547 Shore Drive, Oakdale

$1,125,000

8 Beds ⋅ 6 Baths ⋅ 1048517 MLS

Welcome to 82 Yale Avenue, Oakdale. A Rare Multigenerational Opportunity. This expansive 7-bedroom, 5-bath Oakdale residence sits on approximately 0.70 acres. Designed for flexibility and extended-family living, the home features three separate entrances, three kitchens, and multiple living spaces—offering excellent potential for a mother-daughter setup or a large multigenerational household. A finished lower level, 2-car attached garage, spacious private driveway, and generous backyard provide the space, privacy, and versatility today's buyers are looking for. A truly unique opportunity in a desirable Oakdale location.

82 Yale Avenue, Oakdale

$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

$579,000

2 Beds ⋅ 2 Baths ⋅ 1047899 MLS

Beautifully updated 2 bedroom ranch with the potential for a 3rd bedroom, offering 2 full baths and a bright, inviting interior. Hardwood floors, custom moldings, recessed lighting, and two skylights add warmth and character throughout. The updated kitchen features granite countertops, stainless-steel appliances, and a glass tile backsplash, while the living room and dining room provide comfortable spaces for everyday living. A huge walk-in closet with a custom organizing system offers exceptional storage. Additional features include central air conditioning, gas hot-air heat, updated windows, and vinyl siding. Outside, enjoy professional landscaping, a private backyard with vinyl fencing, and a paver patio perfect for relaxing or entertaining, and a detached garage offering additional parking and storage. All this, plus taxes of only $9,644.14 after the Basic Star rebate. Low maintenance, low taxes, low utilities…low bills! A true must see.

28 Academy Lane, Oakdale

$750,000

4 Beds ⋅ 2 Baths ⋅ 1046548 MLS

Set midblock on a third of an acre, this open-concept Colonial spreads 1,909 square feet across seven rooms. The eat-in kitchen stretches to island seating, with granite counters, stainless appliances and pantry storage. A wood burning stove anchors the living room, and the family room opens through patio doors to a fenced backyard. Four bedrooms include a primary with double closets and its own bathroom entry, and oak floors carry through the home. Behind the finishes: 200-amp generator-ready service, smart thermostats, ENERGY STAR appliances, double-pane windows, an entrance foyer, attached garage, private driveway, and sprinklers front and rear. Two state parks, the Bayard Cutting Arboretum, the train station, shops, and downtown and waterfront dining are all close by.

87 Wexford Drive, 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

$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

$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

$775,000

3 Beds ⋅ 2 Baths ⋅ 1038275 MLS

Beautiful well kept Ranch on a STAGGERING 1.55 Acres in the heart of Oakdale in the desirable Connetquot Schools. Make this your new private compound with plenty of property to add a pool, giant garage and still have wide open grass fields. This home is set back approximately 300' from Locust avenue at the end of a long driveway with the feel of your very own private road. Young home built 1991 and very well maintained featuring 3 Beds and 2 Full Baths with a large open layout Living/Dining and Kitchen space. Central Air, 200 Amp Service, Inground Sprinklers front + back. Very rare to see this size property for a single home in Oakdale.

72 Locust Avenue, 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

$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

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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.