Courtesy: Eric G Ramsay Jr Assoc LLC
631-665-1500
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.
Courtesy: Compass Greater NY LLC
631-491-2926
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.
Courtesy: Signature Premier Properties
631-567-0100
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.
Courtesy: Douglas Elliman Real Estate
631-589-8500
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..
Courtesy: Keller Williams Realty Elite
516-795-6900
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.
Courtesy: Compass Greater NY LLC
631-491-2926
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!
Courtesy: Power Team Realty Corp
631-231-8000
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!
Courtesy: Douglas Elliman Real Estate
631-589-8500
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.
Courtesy: Douglas Elliman Real Estate
631-589-8500
Welcome to effortless living in this beautifully maintained townhouse-style residence located within a desirable 55+ gated community in the heart of Oakdale. Offering a spacious layout, attached one-car garage, and thoughtful design throughout, this turnkey home perfectly blends comfort, convenience, and style. A dramatic two-story entry immediately welcomes you with soaring ceilings, hardwood floors, an elegant dining area with chandelier, and a beautiful view of the second-floor overlook above. The open-concept layout continues into a spacious living room featuring a gas fireplace and seamless flow into the kitchen. The well-appointed kitchen offers cherry cabinetry, granite countertops, stainless steel appliances, countertop seating, and an additional dining area overlooking the private patio and beautifully maintained grounds. A generously sized powder room completes the main level. Access the second floor by either the staircase or the custom raised wood-panel elevator, providing convenient access to all levels of the home, including the basement. Upstairs, a spacious landing overlooks the dining area below and leads to the primary suite featuring multiple closets, a built-in vanity area with mirror, and a private bathroom complete with dual sinks and a large walk-in shower with bench seating. An additional guest bedroom and full guest bathroom provide comfortable accommodations for family and visitors. The lower level offers additional finished living space with an electric fireplace and a flexible area currently used as a home gym. The unfinished portion provides an abundance of clean storage space, a laundry center, and an egress window, creating endless possibilities. Perfectly positioned within the community, residents enjoy a picturesque setting featuring a gated entrance, beautifully landscaped grounds, a tranquil pond with fountain, and a welcoming clubhouse with fireplace for events and gatherings. Conveniently located near Sunrise Highway, shopping, dining, and everyday amenities. Exceptionally maintained, thoughtfully designed, and truly move-in ready — this Oakdale residence offers the ease of 55+ community living in a warm and inviting setting.
Courtesy: Coldwell Banker American Homes
631-863-9800
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.
Courtesy: HomeCoin.com
888-400-2513
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 MOVE-IN-READY home will showcase quality craftsmanship, modern finishes, and an exceptional layout designed for today's lifestyle. The FULLY LANDSCAPED property will include a fenced in, private outdoors 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!
Courtesy: OverSouth LLC
631-770-0030
Spacious 4/5 bedroom home with additional living space. Discover this 3,830-square foot home offering the perfect blend of space, comfort, and versatility. Featuring 4/5 generously sized bedrooms, this property is designed to accommodate modern living with room for everyone. In addition to the main living areas, enjoy approximately 880 square feet of extra living space. Ideal for a family room, home office, recreational area, guest suite, or multi-generational living with all handicapped access. Also, all radiant heating and 3 heating zones. The home's expansive lay out provides ample room for entertaining, relaxing, and everyday living. Large living spaces, abundant of closets and storage, and flexible-use areas make this property a rare find. Whether you're looking for room to grow or space to customize to your lifestyle, this home offers endless possibilities. Welcome home!!
Courtesy: Compass Greater NY LLC
631-491-2926
Welcome to this stunning, meticulously maintained 2-bedroom, 2.5-bath colonial townhome nestled in the sought-after Willow Wood community of Oakdale. From the moment you step onto the charming covered front porch, you'll feel the warmth and character that sets this home apart. The main level impresses with gleaming hardwood floors throughout and an open, flowing layout perfect for everyday living and entertaining. The spacious living room features crown molding, recessed lighting, a gas fireplace, and elegant wainscoting — the perfect gathering space. The beautifully updated eat-in kitchen is a true showstopper, boasting custom gray-toned cabinetry with frosted glass accents, quartz countertops, a farmhouse sink, subway tile backsplash, and gas cooking. The adjoining dining area with bay windows and a chandelier is bathed in natural light, creating a cozy spot for every meal. A half bath and attached garage complete the first floor. Upstairs, the palatial primary suite — measuring an impressive 23'5" x 19'9" — is a true retreat, featuring vaulted ceilings, a ceiling fan, two generous walk-in closets, and a spa-inspired en-suite bath with dual vanities, a glass-enclosed shower, and a crystal chandelier. A bright second bedroom with its own walk-in closet, a full hall bath, and a convenient upstairs laundry room round out the second floor. The sun-drenched landing with skylight and open-to-below view adds an airy, grand feel. Step outside to a private composite deck with room for multiple seating areas, overlooking a lush, landscaped backyard — your own serene outdoor escape. Willow Wood is an all-ages community — open to buyers of any age — with access to a community pool, tennis courts, and clubhouse. All the ease of low-maintenance living without the age restrictions. Truly move-in ready — just bring your personal touch and settle right in!
Courtesy: Century 21 KR Realty
631-563-1616
Welcome to this spacious one-level condominium offering comfortable and convenient living. This well-maintained 2-bedroom, 1-bath home features a large, bright living and dining area with soaring vaulted ceilings, a cozy fireplace, and sliding glass doors leading to a private patio—perfect for relaxing or entertaining. The eat-in kitchen boasts high ceilings, granite counter tops and plenty of space for casual dining. Ceramic tile flooring extends throughout the entire home, providing both style and easy maintenance. Additional highlights include a one-car garage and an open, airy layout designed for everyday comfort. Residents enjoy access to exceptional community amenities, including a clubhouse, outdoor swimming pool, and tennis courts, creating a resort-like lifestyle right at home.
Courtesy: Douglas Elliman Real Estate
631-589-8500
Enjoy Beaches, Boating, Restaurants and Water then this is the House for you!! Located South of Montauk Hwy in the Sought-After Idle Hour Community! This Over-Sized High Ranch has a Super Spacious Eat-In Kitchen with Stainless Steel Appliances, Plenty of Cabinetry for Storage and Extra Seating Area, Living Room with Wood-Burning Fireplace and Doors going out to Front Deck, Primary Bedroom w/ Full Bath, Nice Big Den which also has a Wood-Burning Fireplace, Bright & Airy Florida Room with Windows Galore going out to Large Deck and Patio Area, Natural Gas Heat, Hardwood Floors Throughout, In-Ground Sprinklers and So Much More!! Don't Miss!
Courtesy: Douglas Elliman Real Estate
631-758-2552
Welcome to waterfront living at its finest. Situated in historical Idle Hour on a private road. No Flood Ins. required.!!No neighbors across the street because of the Arboretum. This home sits a beautiful canal-front, this spacious and meticulously maintained 5 bedroom home offers the perfect bled of comfort, boating lifestyle, and flexible living space for extended family. a 3 yr old dock this exceptional property is ideal for the boating enthusiasts with ample room for large vessels and convenient canal access. There are no bridges straight shot to the bay. The bulkhead dock is 90/100 ft. Sellers have had throughout the yrs. not all at the same time, 39 ft. Searay, a 27 Ft .activator, 37 Ft Silverton, 34 Ft. Silverton, 27 ft. Cigarette. There is also a boat ramp. The expansive backyard, paired with the two-level deck overlooking the water, creates the perfect setting for entertaining, outdoor dining or simply relaxing while enjoying serene views. Inside, you'll find versatile layout with generous living space, radiant heating kitchen/dining room floors, downstairs a large family room with a cozy fireplace perfect for gatherings yr. round. Laundry room. A second kitchen for convenience, designed with comfort and functionality in mind, the layout easily accommodates extended family. Spacious two-car garage, oversized driveway, beautifully manicured landscaping and exceptional curb appeal from front to back. A rare opportunity to own a turn-key waterfront retreat offering space, functionality and ultimate coastal lifestyle.
Courtesy: Herrick Real Estate LLC
631-968-5300
Step into a world of timeless charm and waterfront luxury. Located in the coveted Idle Hour Artist Colony of South Oakdale—originally part of William K. Vanderbilt’s 900-acre Gilded Age estate. This unique 2-bedroom, 1.5-bath Colonial offers a rare blend of bohemian history and modern tranquility. The second bedroom is currently the living room, but will be converted back at the seller's expense. This property is a boater dream, enjoy unparalleled canal access with an impressive 150-foot bulkhead, perfect for docking multiple vessels or simply taking in the serene water views. Nestled among the unique, storybook homes of the Artist Colony, this residence reflects the neighborhood's unique architectural heritage, once home to creative minds and historic stables. Situated on a quiet, narrow street in a protected historical district, you are just minutes from local favorites like the Snapper Inn, Mannino's Italian Restaurant and Bayard Cutting Arboretum, with easy access to the LIRR for a seamless commute. This property is a "must-see" gem in one of Long Island’s most enchanting hidden communities.
Courtesy: Exit Realty First Choice
718-380-2500
Rare opportunity to own a piece of history in the historic district of Oakdale. This single family home was once part of the former Vanderbilt Grounds, known as the Artist Colony. With original timbers and finishes, as well as modern conveniences, this home offers the best of both worlds. Features include wide planked hardwood floors, built-in cabinetry, original door and window hardware, and an updated kitchen with stainless appliances. With plenty of space for a home office and more, this home is perfect for those looking for room to spread out. Enjoy the convenience of being near shopping, restaurants, parks, the river, marinas
Courtesy: RE/MAX City Square
516-731-2700
Newly renovated two story expanded ranch in desirable Oakdale neighborhood. This home features four bedrooms, three full baths, open floor plan, family room with electric fireplace, kitchen with island and stainless steel appliances and bedrooms with custom closet organizers. Move-in ready home.
Courtesy: New Island Realty
631-957-0500
Oakdale's exclusive, private & beautiful Vanderbilt Estate Idle Hour historic community. This wideline Hi Ranch has hardwood flooring, large Formal dining, a rear deck & a remodeled 1st floor with a large rear extension. Very nice 100' by 197' landscaped property, inground sprinklers & a detached garage. All hookups for an accessory apartment are in place. A great home in a beautiful setting & highly desitrable area...
Oakdale is located in New York. Oakdale, New York 11769has a population of 7,276. Oakdale 11769 is less family-centric than the surrounding county with 31.58% of the households containing married families with children. The county average for households married with children is 32.94%.
The median household income in Oakdale, New York 11769 is $112,464. The median household income for the surrounding county is $111,660 compared to the national median of $69,021. The median age of people living in Oakdale 11769 is 46.9 years.
The average high temperature in July is 83.2 degrees, with an average low temperature in January of 23.4 degrees. The average rainfall is approximately 47.3 inches per year, with 27.6 inches of snow per year.
