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$729,000
3 Beds ⋅ 2 Baths ⋅ 1049112 MLS
Pristine 3 Bd, 2Bth Colonial located in the desirable Connetquot School District. This home showcases True Pride of Ownership inside and out and is perfectly designed for entertaining. Inside features an elegant dining room, updated kitchen with stainless appliances and island. Upstairs offers three spacious bedrooms, including a primary suite with a walk-in closet, plus a den that provides excellent space for children, toys, or a cozy lounge area. The second- floor features central air conditioning, while the first floor is equipped with an efficient ductless unit. The exterior features a beautifully manicured lawn, fenced yard, firepit, and a covered patio ideal for gatherings. Inside, the living spaces are thoughtfully updated and impeccably maintained. This is a home you'll be proud to call you own--warm, inviting and beautifully cared for.

234 Brook Street, 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. 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
$1,475,000
4 Beds ⋅ 3 Baths ⋅ 1039412 MLS
Tucked away on a private South of Montauk cul-de-sac in Oakdale’s coveted Idle Hour community, this exquisitely reimagined 3,700 sq. ft. coastal colonial rests on a beautifully landscaped 0.7-acre waterfront lot with direct water access—offering the rare ability to launch jet skis, kayaks, and paddleboards from your own backyard. Seamlessly blending timeless South Shore architecture with sophisticated modern smart-home features, the residence delivers an exceptional lifestyle in one of the area’s most desirable enclaves. The sun-filled main level showcases an open-concept design with refined custom millwork, an elegant living room with gas fireplace and a chef’s eat-in kitchen appointed with quartz countertops, premium stainless appliances, and a built-in beverage center. The main-level primary suite offers a serene retreat, complete with dual walk-in closets and a stunning bath with smart-controlled heated tile floors, making it ideal for luxurious everyday living or private guest accommodations. Upstairs, three generously scaled bedrooms feature custom shiplap detailing, expansive closet space, and a beautifully finished full bath. The exterior has been transformed with exceptional attention to detail, featuring a grand TimberTech front porch with sleek black aluminum metal roof, new planting beds, and mature American boxwoods. The resort-like backyard has been fully cleared, leveled, and hydroseeded with lush Kentucky bluegrass, then enclosed with black horizontal aluminum and estate fencing, framed by 60 Green Giant arborvitae for ultimate privacy. Additional highlights include a resurfaced patio and an 11-zone smart Hunter irrigation system. Perfectly positioned near the river, marinas, LIRR, and top-rated Connetquot schools, this remarkable home offers an unmatched blend of elegance, comfort, and coastal living south of Montauk Highway

16 Twin River 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
$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
$1,199,990
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
$740,000
3 Beds ⋅ 2 Baths ⋅ 1021139 MLS
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!

566 Locust Avenue, 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
$779,999
4 Beds ⋅ 2 Baths ⋅ 1004296 MLS
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!

661 Shore Drive, Oakdale
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 1000816 MLS
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.

24 Biltmore Avenue Extension, Oakdale
$465,000
4 Beds ⋅ 3 Baths ⋅ 980770 MLS
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

17 Jade Street, Oakdale
$824,990
3 Beds ⋅ 2 Baths ⋅ 924569 MLS
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...

59 Edgewood Avenue, Oakdale

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.