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21 Princess, Oakdale
$1,560,000
3 Beds ⋅ 3 Baths ⋅ 1024343 MLS
One-of-a-Kind Ranch Home with 2,692/3,200 Square Feet Located in the Historic Idle Hour Artist Colony Subdivision of Oakdale South of Montauk Highway. Situated on a Private .67 Acre Landscaped Parcel with a Heated Gunite Inground Pool, Surrounding Tiled Patio, and Custom Sauna. Enter onto the Covered Front Porch into a Hallway with Cathedral Ceiling into the Living Room with Front and Rear Double Sliding Doors, 24 Skylights and Tiled Floor. Den/Dining Room/4th Bedroom with Stained Glass Windows, Full Bath with Shower with Radiant Heated Floor and Laundry Area, into the Custom Kitchen with 18 Foot Ceiling, 2 Sinks, Refrigerator and Freezer, 2 Dishwashers, Island to Seat 6 and Sliding Doors to Backyard. Hallway Full Bath with Tub and Radiant Heated Floor, 2 Bedrooms with Double Closets, and Sitting Room with 2 Sets of Double Closets for Office or Gym into the Primary Bedroom with Sliding Doors Out to a 2nd Front Porch, Walk-In Closet and Full Bath with Radiant Heated Floor, Skylight and Shower. 2-Car Attached Garage with Interior Access. Navian Gas Hot Air Heating System, 200 Amp Electric, Generator, 2 Sheds and Inground Sprinklers. Too Much to List!

21 Princess, Oakdale

1 Fairwind Court, Oakdale
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 999539 MLS
Welcome to 1 Fairwind Court, an exceptional waterfront residence located in the highly sought-after Water Pointe community of Oakdale. Perfectly positioned on scenic Water Pointe Pond, this elegant and spacious Colonial offers over 3,000 square feet of luxury living with 5 bedrooms, 3.5 baths, and a lifestyle designed for both relaxation and entertaining. Combining refined interiors, resort-style amenities, and direct boating access to the Great South Bay, this is South Shore living at its finest. The home is a beautifully updated throughout. Featuring an eat-in kitchen featuring premium Wolf appliances, including a Wolf oven, along with Sub-Zero refrigerator and freezer systems that blend sophistication with top-tier performance. Granite counter tops in the kitchen area carries into the powder room, wet bar and fireplace surround. Designed with both functionality and style in mind, the kitchen opens seamlessly into expansive living and dining spaces filled with natural light, hardwood flooring, elegant crown molding, wainscoting, and custom mill work throughout. The luxurious primary suite serves as a private retreat with two walk-in closets, a spa-inspired bath, and a private balcony overlooking the tranquil pond. Additional highlights include spacious guest accommodations, a main-floor office, central air conditioning, natural gas heating, high ceilings, and a fully finished basement offering a lounge area and work out room. Outdoor living is equally impressive. Residents enjoy a deeded boat slip with direct canal access to the Connetquot River and Great South Bay, making this home ideal for boating enthusiasts and waterfront lovers alike. The beautifully maintained Water Pointe community offers resort-style amenities including an in-ground pool, tennis courts, professionally landscaped grounds, snow removal, lawn maintenance, and trash removal for truly carefree living year-round. Situated on a quiet cul-de-sac in one of Oakdale’s most desirable waterfront communities, 1 Fairwind Court delivers the perfect blend of luxury, convenience, and coastal charm — all with low-maintenance living and no flood insurance currently required. This is a rare opportunity to experience the very best of waterfront living on Long Island’s South Shore.

1 Fairwind Court, Oakdale

270 Edgewood Avenue, Oakdale
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 979848 MLS
True new construction in Oakdale on a rare half-acre backing protected land—professionally elevated with engineered grading for long-term drainage and peace of mind—offering privacy, space, and proximity to the Great South Bay. Built from the ground up in 2023 with a new foundation, roof, and all mechanical systems, this 3,200+ sq ft residence delivers modern living in an area where most homes require significant updating—offering long-term value and low-maintenance ownership. Located just minutes from the Great South Bay and the optional beach club, residents enjoy access to a marina, pool, private beach, boat slips, and waterfront dining. Convenient to the Oakdale LIRR station for easy access to New York City. Inside, the open-concept layout is designed for both everyday living and entertaining, featuring a grand two-story foyer, 9-foot ceilings, wide-plank flooring, crown moldings, recessed lighting, and built-in speakers throughout. The gourmet kitchen is outfitted with custom shaker cabinetry, quartz countertops, GE stainless steel appliances, and flows seamlessly into the oversized family room—creating a central gathering space filled with natural light. A flexible floor plan includes a first-floor office or optional bedroom, ideal for guests, remote work, or multigenerational living. With 4 bedrooms and 3 full baths, the home offers both space and versatility. The primary suite features a private bath, while the second floor includes additional bedrooms, a dedicated laundry area, and generous attic storage. The property has been professionally elevated and engineered with custom grading and a drywell drainage system, designed to enhance usability and help keep the property dry and protected year-round. The fully fenced backyard opens to preserved land, offering a rare level of privacy with no rear neighbors. Outdoor features include Trex decking, a screened-in porch, in-ground sprinklers, and a spacious yard ideal for entertaining or future customization. Additional highlights include a 2-car garage, two-zone heating and central air, and premium Azek exterior trim. A rare opportunity to own true new construction on a private half-acre in one of Oakdale’s most desirable locations.

270 Edgewood Avenue, Oakdale

24 Twin River Drive, Oakdale
$1,225,000
5 Beds ⋅ 3 Baths ⋅ 949230 MLS
Located in Desirable Idle Hour Section of Oakdale , This Sunning 3700 sq ft Open Concept Waterfront Colonial Blends Elegant Design w/ Resort -Style Living. The First Level Is Designed For Both Everyday Living and Entertaining, Showcasing a Chefs Kitchen w/ Miele & Wolf Appliances, Granite Countertops & Stainless Finishes. Additional Highlights Include a Formal Dining Room, an Expansive Living Room w/ Soaring Ceilings, and a Stylish Bar Area w/ Miele Wine Refrigerator, Additional Miele fridge & Ice Maker. The Second Level Features Two Primary Bedrooms and a Versatile Loft, Ideal for a Home Office or Den. Enjoy Peace of Mind w/ New Central Air & Heating. Step Outside To Your Private Waterfront Oasis Featuring an In -Ground Pool, Cambridge Pave Patio , Two Jet Ski Lifts, and 140' Ft of Navy Bulkheading w/ Water & Electric. Shed is a gift, Solar Panels Are Owned.This Home Is Perfect For Embracing The Ultimate South Shore Lifestyle.

24 Twin River Drive, Oakdale

251 Oakwood Road, Oakdale
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 992313 MLS
Welcome to 251 Oakwood Road, Oakdale – a stunning custom-built home, constructed in 2002, offering exceptional space, quality, and luxury throughout. This beautiful 5-bedroom, 2.5-bath residence features a striking stone and vinyl exterior, covered front porch with TimberTech decking, and impressive two-story formal entry. Inside, you’ll find a gorgeous custom kitchen renovated in 2021, formal living room, formal dining room, spacious den with wood-burning fireplace, pantry, mudroom with laundry, and a private office or 5th bedroom. The luxurious primary suite offers two walk-in closets and a spa-like full bath with soaking tub and walk-in shower. Additional highlights include a full basement with 8-foot ceilings, outside entry, 200-amp electric, whole-house natural gas generator with automatic transfer switch, and a two-car garage with electric door openers. Enjoy year-round comfort with new two-zone central air and Buderus two-zone hydronic air heat fueled by oil with two 330-gallon tanks. Outdoor living is extraordinary with a heated 32x16 in-ground pool featuring a custom waterfall, 9-zone in-ground sprinklers, and beautifully maintained grounds. Located in the Connetquot School District, this extraordinary home combines elegance, functionality, and resort-style living!

251 Oakwood Road, Oakdale

168 Bayview Drive, Oakdale
$1,040,000
5 Beds ⋅ 3 Baths ⋅ 974578 MLS
Discover Your Dream Lifestyle in South Oakdale: A Stunning Home Awaits! Nestled in the highly coveted Oakdale, this beautifully remodeled farm ranch epitomizes modern living while offering the charm of a timeless home, making it a perfect generational residence. Just seconds away from marinas, gourmet restaurants, town parks, and vibrant shopping, this property is an entertainer's dream. As you step through the inviting brick-floored foyer, you are welcomed by expansive formal living and dining areas that set the perfect stage for gatherings. The brand-new kitchen dazzles with a central island, quality cabinetry, and stunning quartz countertops, seamlessly designed for culinary enthusiasts. A hidden pantry adds an element of surprise, while stainless steel appliances ensure functionality. The adjoining oversized den, complete with a cozy wood-burning fireplace, flows into a sun-drenched sunroom featuring exposed beams and a cathedral ceiling, creating an idyllic space for relaxation.This thoughtfully designed home boasts a primary ensuite and an additional guest bedroom or home office on the first floor, making it ideal for multi-generational living. A second primary suite and two generous guest bedrooms are located on the upper level, providing ample space for family and guests. Impeccably designed and future-proof, with a two-car garage and mere minutes from train access, major highways, and the local airport, this residence is truly a rare gem, ready to welcome you into a lifestyle of comfort and elegance.

168 Bayview Drive, Oakdale

18 Ludlow Way, Oakdale
$955,000
5 Beds ⋅ 2 Baths ⋅ 1014765 MLS
Welcome to 18 Ludlow Way in Oakdale! This turn-key 5 bedroom 2 bathroom Colonial is located in desirable South Oakdale, just minutes from the marinas, waterfront restaurants, and everything the Connetquot River lifestyle has to offer. The first floor has been tastefully updated with fresh paint, wainscoting throughout, and a renovated bathroom. Major improvements include conversion to natural gas, brand-new central air conditioning, upgraded electrical service, and a dry basement with French drains and a new sump pump. Outside, the backyard has been completely transformed and is perfect for entertaining. Enjoy a large paver patio with built-in lighting, new sod, WiFi-controlled in-ground sprinklers, a gazebo with electric, custom outdoor bar with electric, turf play area, pet run, storage shed, and beautiful Belgium block landscaping and garden beds. The newly expanded driveway and two-car garage provide plenty of room for cars and even your boat. Where else can you find a beautiful listing like this with LOW taxes with Basic STAR that is NOT in a flood zone?! If you're looking for a move-in-ready home with space, updates, and an amazing location with attention to detail, 18 Ludlow Way is one you won't want to miss!

18 Ludlow Way, Oakdale

25 Middlesex Avenue, Oakdale
$951,000
4 Beds ⋅ 3 Baths ⋅ 1000719 MLS
Welcome To This Spacious & Well-Maintained Idle Hour Colonial Offering A Thoughtful Layout And Exceptional Features Throughout! Welcomed By A Foyer With Double Closets Leading To A Formal Living Room w/Gas Fireplace & Formal Dining Room w/Wood Floors Throughout. The Eat-In Kitchen w/Tile Flooring, Granite Countertops, Recessed Lighting, Gas Cooking, Pantry Closet w/Access To The Crawlspace, Updated Appliances Including A Maytag Refrigerator & GE Microwave (2022), And Andersen Sliders Leading To A Large 14x36 Paver Patio. A Large Half Bath On The Main Level w/Whirlpool Washer/Dryer, A Stunning Den w/Vaulted Ceilings. Upstairs You’ll Find Generously Sized Bedrooms w/Large Closets, Including An Oversized Closet Off One Bedroom. The Spacious Primary Suite Features Vaulted Ceilings And A Private En-Suite Bath w/Tub, Shower And Skylight. Additional Features Include Andersen Windows, Pull-Down Attic Access, 2-Car Garage, Alarm System, 200 Amp Electric, Tempstar Heating System & Air Handler (2012), Rheem Water Heater Approximately 5 Years Young, And Garage Door Electronics Replaced In 2012, One Cesspool w/7 Leach Fields. This Home Has Truly Been Cared For Since It Was Built In 2004 & Is Ready For It’s Next Owner!

25 Middlesex Avenue, Oakdale

20 Canterbury Court, Oakdale
$930,000
4 Beds ⋅ 3 Baths ⋅ 1003700 MLS
Welcome to this beautifully updated 4-bedroom, 2.5-bath Colonial nestled in the highly sought-after South Oakdale location. Completely renovated from top to bottom between 2018 and today, this move-in-ready home offers the perfect combination of modern luxury, thoughtful upgrades, and effortless living. Step inside to discover a bright open floor plan designed for both everyday comfort and entertaining. The stunning kitchen serves as the heart of the home, featuring quartz countertops, stainless steel appliances, and seamless flow into the surrounding living spaces. Upstairs, retreat to the newly completed primary suite featuring a spa-inspired bathroom with an oversized walk-in shower, radiant heated floors, double vanity, and a spacious walk-in closet designed with both style and function in mind. The updates continue throughout the home and exterior with a newer roof complete with owned solar panels, new vinyl siding, windows, overhead LED lighting throughout, doors, base & crown moulding and a full-house renovation in 2018/19 that leaves nothing left to do except unpack. Additional upgrades include newly installed ductless split units (2023) providing efficient whole-house air conditioning and comfort year-round. Enjoy outdoor living on the front paver patio or in the fully fenced backyard featuring a composite deck overlooking the property—ideal for summer entertaining, relaxing evenings, and gatherings with family and friends. A full PVC fence surrounds the property for added privacy, while the attached two-car garage provides convenience and additional storage. A rare opportunity to own a completely updated home in one of Oakdale’s most desirable locations—close to parks, marinas, beaches, and all that the South Shore lifestyle has to offer. Every detail has already been done. Simply move in and enjoy.

20 Canterbury Court, Oakdale

517 Ocean Avenue, Oakdale
$915,000
4 Beds ⋅ 2 Baths ⋅ 1025588 MLS
Beautiful 4 Bedroom 2 Full Bath Ranch offering an open and inviting floor plan perfect for entertaining. The custom Kitchen features vaulted ceilings, cherry wood cabinetry, granite countertop, tiled backsplash, stainless Steel Appliances and a wood burning stove that opens up to a spectacular Great Room with soaring vaulted been ceiling, a stunning stone accent wall, abundant natural light, a gas fireplace, and a wet bar. The Formal Dining room is enhanced with crown molding. Convenient mudroom off the attached 2 car garage. The full bright basement is partially finished and offers a living room/playroom, full bathroom, laundry room, utility/storage area, and an outside entrance. Enjoy the beautiful professionally landscaped front and backyard featuring a paver front stoop and walkway. rear paver patio, and private deck off primary bedroom, Flower perennial garden, Gazebo and a storage Shed. Wood flooring and luxury laminate throughout main level. Anderson windows throughout (except two Pella windows). Additional features include gas heat/cooking, 200-amp electric service and precast cesspools. A truly exceptional home offering comfort, quality craftmanship, and outstanding indoor and outdoor living.

517 Ocean Avenue, Oakdale

6 Connetquot Drive, Oakdale
$910,000
5 Beds ⋅ 4 Baths ⋅ 954449 MLS
Not all renovations are created equal and this one proves it. Set in Oakdale’s sought-after Idle Hour community and the Connetquot School District, this fully reimagined 5-bedroom, 3.5-bath residence delivers space, style, and substance in one seamless package. From the moment you step into the dramatic cathedral entry, the home opens up with soaring ceilings, sun-filled living spaces, and rich hardwood floors designed for real life and real entertaining. The kitchen is a true centerpiece, featuring stainless steel appliances, extensive cabinetry, and a hidden walk-in pantry that elevates both form and function. A warm, inviting den with fireplace anchors the main level, while the primary suite offers a quiet retreat complete with double closets and a spa-inspired bath. Behind the scenes, every major system has been thoughtfully updated including heat, central air, plumbing, 200-amp electric, roof, siding, and windows so you can focus on living, not projects. Moments from beaches, major roadways, and the LIRR, this home checks the boxes buyers are actually looking for today: turnkey condition, smart upgrades, and an unbeatable Oakdale lifestyle.

6 Connetquot Drive, Oakdale

8 Wichard Drive, Oakdale
$821,000
3 Beds ⋅ 2 Baths ⋅ 981915 MLS
Welcome to this beautifully updated and thoughtfully designed ranch, set in the historically rich South Shore town of Oakdale. From the moment you make your way into the entry, you’re welcomed into a bright and expansive living room, with gleaming hardwood floors and oversized windows that bathe the space in natural light. At the heart of the home, a meticulously and tastefully designed chef’s kitchen showcases timeless cabinetry, a classic tile backsplash, stainless steel appliances, Quartz countertops and a striking five-burner range, complemented by a charming dining area that's perfect for everyday living. Just beyond, the formal dining room impresses with soaring vaulted ceilings and French doors that open seamlessly to the backyard, creating an effortless indoor-outdoor flow. The home continues with a generously sized primary bedroom to fall in love with, along with two spacious secondary bedrooms, and two beautifully appointed bathrooms, one featuring a classic claw-foot tub and convenient laundry area. The fully finished lower level offers an abundance of additional living space, complete with a separate outside entrance, ideal for entertaining, hosting, or extended use. Outside, you'll discover a true backyard Oasis - a breathtaking heated saltwater pool is framed by manicured gardens, while a covered pergola and expansive patio set the tone for relaxed, elevated outdoor living. An oversized, detached and heated garage completes the home, all set on a generous 0.55 acre lot within the Connetquot School District. With countless carefully curated updates throughout, as well as natural gas and central air conditioning, this exceptional home is a rare opportunity - a stunning retreat that's intentionally designed to offer a special lifestyle.

8 Wichard Drive, Oakdale

7 Katherine Place, Oakdale
$800,000
4 Beds ⋅ 2 Baths ⋅ 981259 MLS
The one you have been waiting for! Stunning Cape Cod style home offering 4 bedrooms and 2 full baths, thoughtfully designed to combine timeless charm with modern comfort. The finished basement with exterior entrance creates versatile living space, ideal for extended living, guests, a private office, or recreation. Escape to your own private backyard oasis featuring a pool, lush landscaping, and a fully fenced setting designed for both relaxation and entertaining. Plenty of room to park your boat, making this property a rare find for those who appreciate the convenience of coastal living and outdoor enjoyment. Warm, inviting, and beautifully maintained, this move in ready home offers the perfect lifestyle, just in time for summer!

7 Katherine Place, Oakdale

182 Connetquot Drive, Oakdale
$797,000
3 Beds ⋅ 2 Baths ⋅ 942044 MLS
Welcome to this exceptional waterfront ranch in the desirable Idle Hour community of Oakdale. Offering 1,600 sq. ft. of thoughtfully designed living space, this home provides an ideal opportunity to enjoy true Long Island waterfront living with direct canal access just moments from the Connetquot River and the Great South Bay—no bridges to navigate. Step inside to a spacious layout featuring wood flooring, an open living room with a bay-window bump-out and an adjacent dining room perfect for gatherings. The kitchen offers a breakfast bar, wall oven, and abundant natural light from another bay-window bump-out. The cozy family room, complete with a classic brick wood-burning fireplace offers warm canal views and a perfect place to unwind. The owner’s suite includes a walk-in closet and private bathroom with a walk-in shower. Two additional bedrooms, a full guest bathroom completes the sleeping wing. A dedicated laundry room provides everyday convenience. Step outside to your own waterfront oasis with desirable southern exposure, a deck, dog run, over 90 feet of bulkhead, and two finger docks suitable for vessels of various sizes. The property also features a natural boat ramp, offering convenient on-site launching and retrieval for smaller boats, kayaks, or personal watercraft. Boaters will appreciate direct, effortless access to open water, making this an ideal home for those who truly love life on the water. A 1-car garage offers added storage with utilities conveniently positioned at the rear. Set within the scenic Idle Hour community along the Connetquot River, this home offers a rare chance to live in one of Oakdale’s most historic and picturesque neighborhoods. Once part of the famed Vanderbilt estate, Idle Hour is celebrated for its natural beauty, waterfront setting, and close proximity to marinas, parks, dining, entertainment, shopping, and the Oakdale LIRR station—ideal for commuters and weekend explorers. Optional amenities include membership at the private Idle Hour Beach Club - offering pools, a clubhouse, beach access, and marina or Byron Lake Park with its modern pool complex and recreational facilities. Experience the perfect blend of lifestyle, location, and Long Island charm. Don't miss this rare opportunity—Call today for a showing!

182 Connetquot Drive, Oakdale

427 Vanderbilt Boulevard, Oakdale
$785,000
3 Beds ⋅ 3 Baths ⋅ 1004669 MLS
Welcome to this beautifully updated expanded Cape nestled in the prestigious Idlehour section of Oakdale, where timeless charm and modern sophistication come together effortlessly. Perfectly positioned near the waterfront, this exceptional home offers an abundance of natural light, thoughtful design, and inviting spaces both inside and out. The home features 3 spacious bedrooms and 2.5 beautifully updated bathrooms, including a stunning ground floor primary suite with vaulted ceilings that create a bright and airy retreat. The dynamic floor plan is ideal for entertaining while still offering the warmth and functionality needed for everyday living and home-cooked meals with family and friends. Upstairs, you’ll find two generously sized bedrooms along with an additional full bathroom, providing comfortable accommodations for family or guests. Hardwood floors run throughout the home, complemented by central air conditioning, gas heating and cooking, a fireplace, and a smart home system integrated with Alexa for seamless modern living. Step outside into your own private entertainer’s paradise featuring an outdoor kitchen, gazebo, fire pit lounge area, patio pavers, and a spiral staircase leading to a rooftop deck with beautiful views overlooking the Great South Bay. Upgraded include: a 2 year old roof, 2 year old HVAC system, 1 year old water heater, expanded septic system (2 new rings). A rare opportunity to own a move-in-ready home in one of Oakdale’s most sought-after waterfront communities.

427 Vanderbilt Boulevard, Oakdale

25 Greentree Drive, Oakdale
$780,000
3 Beds ⋅ 2 Baths ⋅ 1016458 MLS
Welcome to 25 Greentree Drive, a beautifully renovated split-level home offering 3 bedrooms, 1.5 bathrooms, and a partially finished basement. This move-in ready home features an open-concept layout with abundant natural light, skylights, hardwood and vinyl flooring, and a fully renovated kitchen with a center island, stainless steel appliances, and modern finishes. Recent improvements include new siding, new windows, and a newly installed driveway, providing excellent curb appeal. Additional features include natural gas heating, central air conditioning, a one-car garage, and a fully fenced backyard with a paver patio, perfect for outdoor enjoyment. Conveniently located near shopping, restaurants, parks, schools, and major roadways, this home offers a combination of updated living spaces and everyday convenience. Don't miss the opportunity to make this beautifully updated property your next home.

25 Greentree Drive, Oakdale

61 Yale Avenue, Oakdale
$775,000
3 Beds ⋅ 2 Baths ⋅ 1017429 MLS
SpectacularBeautiful & Bright 3 Bedroom. 2 Full Bath Hi Ranch mid-block location Set on a beautifully fenced 1/2-acre property, this home offers a stunning Open kitchen with Custom Cream Cabinetry, Granite countertops, tile backsplash & SS Appliances. Tray Ceiling, Enjoy Natural light wood floors throughout, beautifully tiled Bathrooms, and a primary walk-in closet. The home features include a rear Trex deck with vinyl railing off the dining room, crab orchard stone front steps with vinyl railings. 16-zone Sprinklers front & back, Professional landscaping, updated 200 Amp Electric, and a newer 4yr old 30 yr architectural roof with new gutters and gutter guards. Front 6' vinyl fencing with a large 10' drive-through gate. Possible M/D with proper permits.

61 Yale Avenue, Oakdale

100 Middlesex Avenue, Oakdale
$765,000
4 Beds ⋅ 2 Baths ⋅ 1030335 MLS
Welcome To This Well Cared For Idle Hour Colonial Situated On A Large Corner Property! Greeted By A Gorgeous Foyer Leading To A Formal Living Room & Formal Dining Room w/Hardwood Floors Throughout. The Eat-In Kitchen Features Wide Plank Tile Flooring, Light Maple Cabinetry, Granite Countertops, Recessed Lighting, Stainless Steel Refrigerator & Microwave, Electric Cooking, Dishwasher & Center Island w/Granite Top. The Main Level Also Features A Stone Faced Fireplace w/Granite Mantle, 4 Year Young Laundry/Mudroom, Half Bath & Andersen Sliders Leading To The Deck w/Beautiful Views Of The Wetlands. Upstairs You'll Find 4 Bedrooms & A Full Bath w/Jacuzzi Tub. Additional Features Include Oil Heat, Gas Is In The Street, CAC, 200-Amp Electrical Service w/Transfer Switch for Generator, Immaculate Attached 2-Car Garage w/Attic Storage, Deck w/Gazebo, 8-Zone IG Sprinklers, Mature Landscaping, 3 Year Young Self Contained Septic System, Water Main Replaced & Expansion Tank Installed In 2026. This Home Has Been So Loved & Is Ready For It's Next Owner!

100 Middlesex Avenue, Oakdale

190 Connetquot Drive, Oakdale
$765,000
4 Beds ⋅ 3 Baths ⋅ 917472 MLS
Welcome to your waterfront dream home! This expansive Cape Cod-style residence is perfectly situated on a private canal with 175 feet of bulkhead, just four homes from the open river — and with no bridges to navigate, you’ll enjoy direct access to the bay beyond. Offering over 3,000 sq ft of living space, this 4-bedroom, 3-bathroom home is designed for comfort, style, and incredible water views. Inside, you’ll find gorgeous hardwood floors throughout, a cherry and granite kitchen featuring stainless steel appliances, and abundant storage to meet all your needs. The home features both a primary and junior en suite, each with private balconies overlooking the serene canal and capturing breathtaking sunsets over the river. Additional highlights include a detached 2-car garage with a loft above — There is a Whole-house generator for that peace of mind, In-ground sprinkler system for easy maintenance, and of course waterfront living! Home needs some TLC, and the bulkhead needs repair. Don’t miss this rare opportunity to craft your own slice of paradise on the water.. They’re not making more waterfront — make this your coastal oasis today. Spacious Waterfront Cape Cod in Coveted Idle Hour Neighborhood.

190 Connetquot Drive, Oakdale

212 Matthews Road, Oakdale
$755,000
3 Beds ⋅ 3 Baths ⋅ 987653 MLS
Welcome home to this beautifully maintained 2,014 sq. ft. residence, perfectly situated on a low traffic street within the highly sought-after Sayville School District. Offering the perfect blend of comfort and recent updates, this 3-bedroom (en suite primary bedroom and secondary bedroom), 3-bathroom gem is ready for its next chapter. Fall in love with the open floor plan and warm ambiance of the kitchen/great room that overlooks the backyard oasis featuring an inviting gunite pool, mature landscaping and expansive decking, perfect for summer gatherings. For those winter evenings, enjoy the warmth of the woodburning stove in the kitchen and great room’s cozy fireplace. The well thought out floor plan provides the perfect flow and convenience for entertaining and everyday living. Peace of mind comes with recent professional updates including the roof (5 years), heating system (10-12 years), saltwater pool equipment (2 years) and updated bathrooms. Plenty of storage or room to expand in the large basement!

212 Matthews Road, Oakdale

360 Locust Avenue, Oakdale
$735,000
4 Beds ⋅ 2 Baths ⋅ 945916 MLS
Come home to space, comfort, and effortless entertaining in this bright and airy split-level home set on a shy half-acre lot. A welcoming foyer leads to an oversized formal dining room and recently remodeled eat-in kitchen, complimented by a convenient powder room, great for hosting loved ones and friends. The sun-filled living room features vaulted ceilings, hardwood floors, and a cozy wood-burning fireplace with brick hearth and chimney, blending classic charm with a contemporary edge. Offering four generously sized bedrooms with hardwood floors and plenty of storage, as well as a full bath with soaking tub and separate shower. Lower level completes the home with versatile family room and basement with laundry, utilities and storage. Outdoor living is equally impressive, with an expansive yard, side-yard patio, and a covered backyard paver patio overlooking mature landscaping and gardens. The property is fully fenced and equipped with front and rear in-ground sprinklers. Additional highlights include a six-plus car driveway, paver walkways, central air conditioning, natural gas heating and recent updates such as newer roof, windows and siding. With its thoughtful layout and modern updates, this home is ready to welcome its next owner.

360 Locust Avenue, Oakdale

21 Amboy Road, Oakdale
$725,000
4 Beds ⋅ 2 Baths ⋅ 951495 MLS
It's not just a House you are buying. You are buying a Lifestyle! Summer is just around the corner! Spend it in your beautiful yard, swimming in the pool, going to the best beaches around! And save on your electric bill with a "young" paid-for-in-full Solar System! An amazing Property in the heart of Oakdale! 4Br, 2 Full Baths bi-level home with a lot of updates on a half-acre fenced property. Roof, siding, and windows were replaced 6 years ago. Solar panels were installed at the same time. Gleaming Wood floors throughout the house. The heating/Cooling system was updated 7 years ago. Heated, saltwater in-ground pool. 8-zone sprinkler system. Easy access to the highways, train station, shopping, and Fire Island Ferries. Make it yours in time to enjoy the tranquility of the yard and pool.

21 Amboy Road, Oakdale

195 Brook Street, Oakdale
$690,000
3 Beds ⋅ 3 Baths ⋅ 964119 MLS
Welcome to 195 Brook Street, Oakdale! This recently renovated 3-bedroom, 2.5-bath Cape Cod sits on a spacious .33-acre corner lot in the desirable Connetquot School District. Nestled in a prime location just moments away from Main Street in Sayville, West Sayville, and Oakdale, this property offers convenient access to shopping, dining, recreation, schools, and transportation. The home has undergone a complete renovation, offering peace of mind with brand new plumbing, electrical, and HVAC systems. Features include natural gas heating, new central air conditioning, new hot water heater, and an upgraded 200-amp electric panel. The newly designed kitchen is equipped with quartz countertops, custom cabinetry, a center island with a farmhouse sink, a dedicated pantry, and brand new appliances. Designed with an open layout, the kitchen transitions smoothly into the main living areas, creating an ideal space for both everyday living and entertaining. New white oak hardwood flooring flows seamlessly throughout the home, while updated windows flood the living space with natural light. Recessed LED lighting further enhances the space, creating a bright and inviting atmosphere throughout the entire home. Enjoy mornings or evenings outside on the brand new wraparound porch — an outdoor retreat that perfectly mirrors the home's warmth and charm. Completely transformed throughout, this property showcases refined modern finishes alongside entirely updated systems for effortless turnkey living. Step inside and come see all that this home has to offer — schedule your showing today!

195 Brook Street, Oakdale

132 Willow Wood Drive, Oakdale
$675,000
2 Beds ⋅ 3 Baths ⋅ 1011977 MLS
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!

132 Willow Wood Drive, Oakdale

110 Willow Wood Drive, Oakdale
$675,000
2 Beds ⋅ 3 Baths ⋅ 975138 MLS
Welcome to this beautiful, mint-condition townhouse located in the quiet, Willow Wood community in Oakdale. This extremely well-maintained 2-bedroom, 2.5-bath home offers a bright and open floor plan, ideal for both everyday living and entertaining. The main level features spacious living and dining areas with great natural light, seamlessly flowing into the kitchen, perfect for hosting guests or relaxing at home. Upstairs, the expansive primary suite serves as a true retreat, complete with two walk-in closets and a private en-suite bath. Both upstairs bathrooms feature radiant heated floors, adding an extra touch of comfort and luxury. Enjoy outdoor living with your own private patio, perfect for entertaining or unwinding. Additional highlights include an enlarged driveway for ample parking and meticulous upkeep throughout the home. This is truly a move-in ready property.. just bring your personal belongings and settle right in! Residents of Willow Wood enjoy access to a community pool, clubhouse, and tennis courts, offering a low-maintenance lifestyle with fantastic amenities.

110 Willow Wood Drive, Oakdale

109 Matthews Road, Oakdale
$673,000
3 Beds ⋅ 2 Baths ⋅ 994047 MLS
Welcome home to 109 Matthews Road, a beautifully maintained three bedroom ranch, nestled in the heart of Oakdale. This residence boasts an ideal layout for both quiet relaxation and grand entertaining, highlighted by a formal dining room and a sun-drenched living area. This move-in-ready gem shines with a modern chef's kitchen featuring granite countertops and stainless appliances, leading into a spacious living room bathed in light from large bay windows. Recent upgrades include new flooring in the den, a renovated bathroom, and newer windows throughout. The basement is a great bonus which can offer additional storage or potential for extra living space. Outside, the park-like backyard is an entertainer's dream, gardens and elegant masonry. With natural gas, low taxes, top-rated schools, and easy access to transit, this home offers the perfect blend of comfort and convenience.

109 Matthews Road, Oakdale

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