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Welcome to 70 Featherbed Lane, a truly special waterfront retreat nestled in the enchanting Idle Hour Artist Colony of Oakdale! Built in 1948 and brimming with timeless charm and character, this unique home is situated within a protected historic district and offers an extraordinary lifestyle surrounded by beauty and history. Featuring one bedroom and one and a half baths, the home also boasts a formal living room that was originally a second bedroom and can easily be converted back to suit your needs. With an impressive 150 feet of bulkhead and gorgeous water views, this property offers a rare opportunity to embrace the tranquility and beauty of waterfront living. Additional features include natural gas hot water heating and a wonderful location just minutes from some of the area’s finest restaurants and the Long Island Rail Road. Rich in history, charm, and endless possibilities, this is more than just a home, it’s a lifestyle! A truly special property in one of Oakdale’s most treasured communities! True Taxes $13,312.43 before basic star rebate.

1 Beds ⋅ 2 Baths ⋅ 1062127 MLS

Welcome to 70 Featherbed Lane, a truly special waterfront retreat nestled in the enchanting Idle Hour Artist Colony of Oakdale! Built in 1948 and brimming with timeless charm and character, this unique home is situated within a protected historic district and offers an extraordinary lifestyle surrounded by beauty and history. Featuring one bedroom and one and a half baths, the home also boasts a formal living room that was originally a second bedroom and can easily be converted back to suit your needs. With an impressive 150 feet of bulkhead and gorgeous water views, this property offers a rare opportunity to embrace the tranquility and beauty of waterfront living. Additional features include natural gas hot water heating and a wonderful location just minutes from some of the area’s finest restaurants and the Long Island Rail Road. Rich in history, charm, and endless possibilities, this is more than just a home, it’s a lifestyle! A truly special property in one of Oakdale’s most treasured communities! True Taxes $13,312.43 before basic star rebate.

70 Featherbed Lane, Oakdale

$875,000

MOTIVATED SELLER- 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.

5 Beds ⋅ 3 Baths ⋅ 1054172 MLS

MOTIVATED SELLER- 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

$949,999

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!!

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

$1,199,990

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!

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

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!

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

$749,000

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.

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

$3,650,000

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.

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

$869,990

OPEN HOUSE FOR 10/10 CANCELLED. 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.

4 Beds ⋅ 5 Baths ⋅ 1018752 MLS

OPEN HOUSE FOR 10/10 CANCELLED. 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

$1,494,999

GROUND-UP, NEW CONSTRUCTION in desirable Oakdale community! This modern luxury, open-concept design offers 3,400 sqft. of livable space, 4-bedrooms, 2.5-baths with 9-ft. ceilings throughout. MAIN LEVEL: Open kitchen/living room, wood burning fireplace, 10-ft. waterfall kitchen island, butler's bar, and top of the line appliances. SECOND LEVEL: 4 bedrooms, 2 full baths, walk-in laundry room equipped with washer/dryer, primary wing with expansive on-suite WIC and spa bathroom. FEATURES: FULLY LANDSCAPED/fenced-in exterior, IN-GROUND POOL, in-ground sprinklers, custom pavers, CUSTOM-BUILT CLOSETS throughout, WHITE OAK hardwood flooring, two-zone BOSCH central heat/air, and oversized, 13-ft. ceiling one-car garage. 150 Bellevue, Oakdale is the perfect blend of a personal oasis and the ultimate hotspot for gathering and entertaining. A rare opportunity to own a BRAND NEW, MOVE-IN READY home in a prime South Shore location.

4 Beds ⋅ 3 Baths ⋅ 1013434 MLS

GROUND-UP, NEW CONSTRUCTION in desirable Oakdale community! This modern luxury, open-concept design offers 3,400 sqft. of livable space, 4-bedrooms, 2.5-baths with 9-ft. ceilings throughout. MAIN LEVEL: Open kitchen/living room, wood burning fireplace, 10-ft. waterfall kitchen island, butler's bar, and top of the line appliances. SECOND LEVEL: 4 bedrooms, 2 full baths, walk-in laundry room equipped with washer/dryer, primary wing with expansive on-suite WIC and spa bathroom. FEATURES: FULLY LANDSCAPED/fenced-in exterior, IN-GROUND POOL, in-ground sprinklers, custom pavers, CUSTOM-BUILT CLOSETS throughout, WHITE OAK hardwood flooring, two-zone BOSCH central heat/air, and oversized, 13-ft. ceiling one-car garage. 150 Bellevue, Oakdale is the perfect blend of a personal oasis and the ultimate hotspot for gathering and entertaining. A rare opportunity to own a BRAND NEW, MOVE-IN READY home in a prime South Shore location.

Bellevue Road, Oakdale

$749,999

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!

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

landlocked pcl, Oakdale

$824,990

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...

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

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