Oakdale Homes for Sale

Welcome to Oakdale, a charming hamlet nestled in the heart of Suffolk County, New York. This picturesque community, located along the scenic banks of the Great South Bay, offers a serene escape from the hustle and bustle of city life while still providing easy access to the vibrant attractions of Long Island. With its rich history, friendly atmosphere, and stunning natural landscapes, Oakdale is an ideal place to call home.

One of the most appealing aspects of Oakdale is its diverse selection of homes for sale. Whether you're seeking a cozy cottage, a spacious family residence, or a luxurious waterfront property, Oakdale has something to suit every taste and budget. Many homes boast beautiful architectural details, lush gardens, and modern amenities, all while maintaining the quaint charm that defines this lovely community.

Living in Oakdale means enjoying a plethora of outdoor activities, from boating and fishing on the bay to hiking and biking along the picturesque trails nearby. With its close-knit community feel, residents often gather for local events and festivals, fostering a sense of belonging and camaraderie. Plus, with top-rated schools and convenient access to shopping, dining, and entertainment, Oakdale is a perfect choice for families and professionals alike.

If you're ready to explore the captivating homes for sale in Oakdale, let us help you find your dream property in this delightful hamlet. Experience the warmth of Oakdale living, where every day feels like a vacation. Your new home awaits!

Newest Oakdale Homes for Sale

$699,900

2 Beds ⋅ 2 Baths ⋅ 1054955 MLS

Welcome home to Windmill Gate! This ranch-style condo is located in a desirable 55+ community of just 110 private, detached homes. Featuring A New Eat In Kitchen, Formal Dining Room, Living Room With Cathedral Ceiling, Skylights, And French Doors Leading To Your Private Patio. You Will Love Your Primary Bedroom With Your Very Own Full Bathroom . Also Included Is A Second Bedroom & Additional Full Bath. Washer/Dryer In Unit. Central Air Conditioning/Heat And One Car Attached Garage With Interior Access. Both bathrooms fully renovated as well as new vinyl flooring installed throughout. New Stainless Steel Appliances. Windmill Gate offers an exceptional lifestyle with an outdoor pool, patio and gazebo, clubhouse, and amenity center featuring billiards, multipurpose rooms for cards and games, sauna, and steam rooms. Stay active and social with neighborhood activities including cards, bocce, bingo, Mahjong, and happy hours.

Oakdale

$899,000

5 Beds ⋅ 3 Baths ⋅ 1054172 MLS

This will not last- Agents bring all of your qualified buyers- minutes to marina and bay, this home has a spacious interior floor plan that is different than all homes located in its development. Beautiful all wood walls and ceiling with sky lights master bedroom with private full bath. One of a kind custom built bar in spacious family room with brick fireplace. All stainless appliance spacious kitchen overlooking large newly stained multi-level deck with outdoor fireplace- perfect for entertaining. Beautiful hardwood floors throughout. Elegant Living room and Dining room. Professionally landscaped. Must see to fully appreciate.

42 Ludlow Way, Oakdale

$825,000

6 Beds ⋅ 3 Baths ⋅ 1053595 MLS

Rare over sized Hi Ranch! Six bedrooms and three full baths spread across 2,741 square feet of living space, 175 Stuyvesant Road has been expanded to accommodate even the largest households. Two full kitchens and a private outside entrance addition make this one especially well suited to multi-generational living, an in-law setup, or added income potential with proper permits. Inside you will find recent updates in every room of the home from hardwood floors, vaulted ceilings, fresh paint, and updated kitchens and bathrooms. The main level has two full baths, one of them being inside a main level primary suite. Outside, a flat fenced yard and Trex-railed deck are ready for entertaining, and the attached two-car garage adds everyday convenience. The roof, electrical, mechanical systems/central air, and cosmetics have all been updated within recent years, so the big-ticket items are already handled. Set in Oakdale with easy access to Montauk Highway's restaurants and shops, a quick connection to Sunrise Highway, and a short drive to Heckscher State Park and South Shore beaches like Robert Moses. All this on a quiet dead end street! True taxes before exemptions 15917.45. Connetquot school district.

175 Stuyvesant Road

$949,999

4 Beds ⋅ 3 Baths ⋅ 1052985 MLS

Golden Opportunity Located South of Montauk on the Water!! This Super Spacious Home has an Eat-In Kitchen w/ Custom Cabinetry & Granite Countertops, Den w/ Gas Fireplace, Primary Bedroom w/ Full Bath, Wood Floors, Natural Gas Heating System, and Also Enjoy a Beautiful, Bright & Airy Sunroom Year Round! New Roof Three Years Young, Whole House Generator, In-Ground Sprinklers and Spectacular, Stone Driveway and So Much More! Don't Miss!!

75 Bayview Drive, Oakdale

$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 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

$1,095,000

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 beautiful 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

$699,000

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

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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.