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$3,600,000

Commanding an incomparable position on Stony Brook Harbor, The Mallows stands as one of the most extraordinary and architecturally significant waterfront estates on Long Island’s North Shore. With over 300 feet of private shoreline and unobstructed panoramic west-facing views, this historic masterpiece captures awe-inspiring sunsets that stretch across the Long Island Sound to the Connecticut horizon. The setting is one of pure serenity and prestige—where every room frames the water and every evening ends in color. Originally commissioned by the Astor family and designed by renowned architect Charles Platt, the estate spans over four acres of manicured grounds blending Gilded Age grandeur with refined modern luxury. Outdoor living is elevated with a heated saltwater pool, spa, private tennis court, waterfront gazebo, vegetable gardens, and a charming chicken coop. Inside, 11 bedrooms, 5.5 baths, and 14 fireplaces showcase timeless craftsmanship and architectural excellence, highlighted by a glass conservatory off the primary suite and a four-season sunroom offering sweeping harbor vistas. The chef’s kitchen features Viking and Sub-Zero appliances and opens seamlessly to an elegant formal dining room ideal for entertaining. Additional luxuries include a three-bedroom guest cottage, three-level elevator, and wine cellar. This offering represents a rare and timely opportunity to own one of the North Shore’s most coveted legacy estates—a property of unmatched beauty, provenance, and waterfront presence. Perfectly located near Stony Brook Yacht Club, Avalon Nature Preserve, and Stony Brook Village, The Mallows is not just a home—it is an enduring statement of elegance, privacy, and coastal grandeur.

11 Beds ⋅ 7 Baths ⋅ 835698 MLS

Commanding an incomparable position on Stony Brook Harbor, The Mallows stands as one of the most extraordinary and architecturally significant waterfront estates on Long Island’s North Shore. With over 300 feet of private shoreline and unobstructed panoramic west-facing views, this historic masterpiece captures awe-inspiring sunsets that stretch across the Long Island Sound to the Connecticut horizon. The setting is one of pure serenity and prestige—where every room frames the water and every evening ends in color. Originally commissioned by the Astor family and designed by renowned architect Charles Platt, the estate spans over four acres of manicured grounds blending Gilded Age grandeur with refined modern luxury. Outdoor living is elevated with a heated saltwater pool, spa, private tennis court, waterfront gazebo, vegetable gardens, and a charming chicken coop. Inside, 11 bedrooms, 5.5 baths, and 14 fireplaces showcase timeless craftsmanship and architectural excellence, highlighted by a glass conservatory off the primary suite and a four-season sunroom offering sweeping harbor vistas. The chef’s kitchen features Viking and Sub-Zero appliances and opens seamlessly to an elegant formal dining room ideal for entertaining. Additional luxuries include a three-bedroom guest cottage, three-level elevator, and wine cellar. This offering represents a rare and timely opportunity to own one of the North Shore’s most coveted legacy estates—a property of unmatched beauty, provenance, and waterfront presence. Perfectly located near Stony Brook Yacht Club, Avalon Nature Preserve, and Stony Brook Village, The Mallows is not just a home—it is an enduring statement of elegance, privacy, and coastal grandeur.

15 Emmet Drive, Head Of Harbor

$2,800,000

A Stunning home, nestled on 2 acres, offering incredible attention to detail. The open floor plan offers in excess of 5000 ft. with five bedrooms and 4 1/2 baths. Upon arrival, you are greeted by a gracious two-story entryway leading to a dramatic great room with gas fireplace and double-height coffered ceiling. The formal living room and dining room have 9 foot ceilings and an abundance of natural light. Oversized chef's kitchen provides a breakfast nook, serving area, coffee bar, and pantry. A guest suite, office and laundry round out the main level. Both staircase lead to the second level where you will find a well appointed primary suite. The space includes fireplace, walk-in closets and luxurious bath with radiant floors and steam shower. Enjoy an additional three bedrooms, two en-suite, plus an additional bath. Extra space includes full basement with 9 foot ceilings and walkout entrance, oversize three car garage, 300 amp service. The home is generator ready. Convenient proximity to New York City. This home provides stunning finishes, mill work and quality construction with access to the North Shore's finest dining, shopping and recreational activities.

5 Beds ⋅ 5 Baths ⋅ 818587 MLS

A Stunning home, nestled on 2 acres, offering incredible attention to detail. The open floor plan offers in excess of 5000 ft. with five bedrooms and 4 1/2 baths. Upon arrival, you are greeted by a gracious two-story entryway leading to a dramatic great room with gas fireplace and double-height coffered ceiling. The formal living room and dining room have 9 foot ceilings and an abundance of natural light. Oversized chef's kitchen provides a breakfast nook, serving area, coffee bar, and pantry. A guest suite, office and laundry round out the main level. Both staircase lead to the second level where you will find a well appointed primary suite. The space includes fireplace, walk-in closets and luxurious bath with radiant floors and steam shower. Enjoy an additional three bedrooms, two en-suite, plus an additional bath. Extra space includes full basement with 9 foot ceilings and walkout entrance, oversize three car garage, 300 amp service. The home is generator ready. Convenient proximity to New York City. This home provides stunning finishes, mill work and quality construction with access to the North Shore's finest dining, shopping and recreational activities.

17 Barn Lane, Head Of Harbor

$2,700,000

Set On 3.5 Private Acres In The Prestigious Village Of Head Of The Harbor, 33 Bacon Road Is A Masterpiece Of Design, Craftmanship And Luxury. Built In 2012, This 4900 Square Foot Georgian Colonial Combines Timeless Architectural Elegance With Modern Conveniences, Offering An Unmatched Lifestyle In One Of Long Island's Most Sought-After Enclaves. The Approach To The Property Is Framed By Lush, Manicured Landscaping, A Stately Stone Facade, And Paver Walkways That Set The Tone For The Refinement Inside. Stepping Through The Grand Front Door, You Are Greeted By A Two-Story Marble-Floored Foyer Crowned With A Sweeping Staircase, A Dramatic And Elegant Introduction To The Home. The Main Level Is Designed For Both Lavish Entertaining And Intimate Gatherings. The Formal Living And Dining Rooms Are Enhanced With Custom Moldings, Coffered Ceilings, And Rich Hardwood Floors. The Gourmet Chef's Kitchen Is The Heart Of The Home, Featuring Granite Countertops, Bespoke Cabinetry, Stainless Steel Appliances, A Spacious Center Island, And An Adjoining Breakfast Area. This Open Space Flows Seamlessly Into The Family Room, Where Soaring Ceilings, A Wall Of Windows, And A Gas Fireplace Create A Warm Yet Impressive Gathering Space. A Luxurious First Floor Primary Suite Offers The Ultimate Retreat With A Spa-Like Bathroom With Jacuzzi Tub, Oversized Glass Shower, Dual Vanities, Granite Counters, A Large Walk-In Closet And Direct Access To The Backyard Via French Doors - Perfect For Morning Coffee Or An Evening Swim. There Are Four Additional Bedrooms In The Home, As Well As A Spacious Bonus Room Upstairs. This Residence Is As Functional As It Is Beautiful Boasting Additional Amenities Including Central Air, Central Vacuum, Full House Generator, As Well As An Unfinished Basement With Exterior Access - Ready For Customization. A Three-Car Garage Offers Ample Space For Vehicles And Storage. A Separate Carriage House Expands The Property's Versatility, Serving As A Fully Equipped Guest Residence Or Entertainment Retreat. Complete With Its Own Kitchen, Bar, Living Area, Bedroom, And Full Bathroom, It Offers A Private Haven For Visitors Or Extended Family. Outdoors, The Property Transforms Into A Private Resort With An Expansive Paver Patio Surrounding The Sparkling Salt-Water And Heated Pool, While The Mature Trees And Plantings Provide Beauty And Privacy Year-Round. The Setting Offers The Tranquility Of A Country Estate, Yet Is Only Minutes From Long Island Sound Beaches, Avalon Nature Preserve, Quaint Stony Brook Village, Local Vineyards, And Is Just 60 Miles From Manhattan! 33 Bacon Road Is More Than A Home, It's A Lifestyle! With Its Blend Of Stately Architecture, Modern Amenities, And An Unbeatable Location, It Represents One Of Head Of The Harbor's Finest Offerings.

6 Beds ⋅ 6 Baths ⋅ 901458 MLS

Set On 3.5 Private Acres In The Prestigious Village Of Head Of The Harbor, 33 Bacon Road Is A Masterpiece Of Design, Craftmanship And Luxury. Built In 2012, This 4900 Square Foot Georgian Colonial Combines Timeless Architectural Elegance With Modern Conveniences, Offering An Unmatched Lifestyle In One Of Long Island's Most Sought-After Enclaves. The Approach To The Property Is Framed By Lush, Manicured Landscaping, A Stately Stone Facade, And Paver Walkways That Set The Tone For The Refinement Inside. Stepping Through The Grand Front Door, You Are Greeted By A Two-Story Marble-Floored Foyer Crowned With A Sweeping Staircase, A Dramatic And Elegant Introduction To The Home. The Main Level Is Designed For Both Lavish Entertaining And Intimate Gatherings. The Formal Living And Dining Rooms Are Enhanced With Custom Moldings, Coffered Ceilings, And Rich Hardwood Floors. The Gourmet Chef's Kitchen Is The Heart Of The Home, Featuring Granite Countertops, Bespoke Cabinetry, Stainless Steel Appliances, A Spacious Center Island, And An Adjoining Breakfast Area. This Open Space Flows Seamlessly Into The Family Room, Where Soaring Ceilings, A Wall Of Windows, And A Gas Fireplace Create A Warm Yet Impressive Gathering Space. A Luxurious First Floor Primary Suite Offers The Ultimate Retreat With A Spa-Like Bathroom With Jacuzzi Tub, Oversized Glass Shower, Dual Vanities, Granite Counters, A Large Walk-In Closet And Direct Access To The Backyard Via French Doors - Perfect For Morning Coffee Or An Evening Swim. There Are Four Additional Bedrooms In The Home, As Well As A Spacious Bonus Room Upstairs. This Residence Is As Functional As It Is Beautiful Boasting Additional Amenities Including Central Air, Central Vacuum, Full House Generator, As Well As An Unfinished Basement With Exterior Access - Ready For Customization. A Three-Car Garage Offers Ample Space For Vehicles And Storage. A Separate Carriage House Expands The Property's Versatility, Serving As A Fully Equipped Guest Residence Or Entertainment Retreat. Complete With Its Own Kitchen, Bar, Living Area, Bedroom, And Full Bathroom, It Offers A Private Haven For Visitors Or Extended Family. Outdoors, The Property Transforms Into A Private Resort With An Expansive Paver Patio Surrounding The Sparkling Salt-Water And Heated Pool, While The Mature Trees And Plantings Provide Beauty And Privacy Year-Round. The Setting Offers The Tranquility Of A Country Estate, Yet Is Only Minutes From Long Island Sound Beaches, Avalon Nature Preserve, Quaint Stony Brook Village, Local Vineyards, And Is Just 60 Miles From Manhattan! 33 Bacon Road Is More Than A Home, It's A Lifestyle! With Its Blend Of Stately Architecture, Modern Amenities, And An Unbeatable Location, It Represents One Of Head Of The Harbor's Finest Offerings.

33 Bacon Road, Head Of Harbor

$1,975,000

Perfectly Positioned In The Prestigious Village Of Head Of The Harbor, This Exceptional All-Brick Estate Offers Timeless Sophistication And Refined Luxury On 2 Private Acres Directly Across From The Serene Beauty Of Stony Brook Harbor. Spanning Nearly 5800 SF, This Custom-Designed Residence Showcases Impeccable Craftmanship And Architectural Detail Throughout, Including 10 Ft Ceilings, Rich Mahogany Floors, And Elegant Arched Entryways. A Grand Yet Inviting Layout Unfolds With Large Principal Rooms, Ideal For Both Intimate Living And Large-Scale Entertaining. The Heart Of The Home Is A Gourmet Chef's Kitchen With Granite Counters, Wolf Appliances And Premium Finishes, Seamlessly Flowing Into Gracious Living And Dining Spaces Anchored By A Fireplace. A Desirable First Floor Primary Suite Offers A Private Retreat With Tranquil Views Of The Grounds And Pool. Outdoors The Property Transforms Into A Resort Setting With An InGround Gunite Pool, Landscaping, And Multiple Areas For Relaxing And Entertaining. Seasonal Water Views Of Stony Brook Harbor Enhance The Home's Natural Beauty And Setting. With 6 Bedrooms And 7.5 Bathrooms, This Residence Offers Exceptional Space, While Its Location, Within One Of The North Shore's Most Coveted Communities, Provides Both Privacy And Proximity To Beaches, Yacht Clubs, Vineyards, And The Charm Of Nearby Villages.

6 Beds ⋅ 8 Baths ⋅ 985682 MLS

Perfectly Positioned In The Prestigious Village Of Head Of The Harbor, This Exceptional All-Brick Estate Offers Timeless Sophistication And Refined Luxury On 2 Private Acres Directly Across From The Serene Beauty Of Stony Brook Harbor. Spanning Nearly 5800 SF, This Custom-Designed Residence Showcases Impeccable Craftmanship And Architectural Detail Throughout, Including 10 Ft Ceilings, Rich Mahogany Floors, And Elegant Arched Entryways. A Grand Yet Inviting Layout Unfolds With Large Principal Rooms, Ideal For Both Intimate Living And Large-Scale Entertaining. The Heart Of The Home Is A Gourmet Chef's Kitchen With Granite Counters, Wolf Appliances And Premium Finishes, Seamlessly Flowing Into Gracious Living And Dining Spaces Anchored By A Fireplace. A Desirable First Floor Primary Suite Offers A Private Retreat With Tranquil Views Of The Grounds And Pool. Outdoors The Property Transforms Into A Resort Setting With An InGround Gunite Pool, Landscaping, And Multiple Areas For Relaxing And Entertaining. Seasonal Water Views Of Stony Brook Harbor Enhance The Home's Natural Beauty And Setting. With 6 Bedrooms And 7.5 Bathrooms, This Residence Offers Exceptional Space, While Its Location, Within One Of The North Shore's Most Coveted Communities, Provides Both Privacy And Proximity To Beaches, Yacht Clubs, Vineyards, And The Charm Of Nearby Villages.

60 Harbor Road, Head Of Harbor

$1,630,000

This distinguished custom Neo-Dutch Colonial is a masterclass in timeless architecture, exceptional craftsmanship, and exquisite detailing throughout. Gracefully set on 2.82 acres of exquisitely landscaped grounds in Head of the Harbor, the residence is designed with both elegance and comfort in mind, offering a seamless blend of expansive entertaining spaces and intimate everyday living—creating a truly refined North Shore retreat. A dramatic two-story entry sets the tone, welcoming you with a custom wood staircase and an immediate sense of scale and sophistication. The home’s gracious layout unfolds into an elegant formal living room featuring 9-foot ceilings and expansive picture windows that bathe the space in natural light while showcasing the surrounding grounds—creating a striking yet inviting setting for both formal gatherings and quiet moments. The formal dining room offers a seamless extension for entertaining, while the stunning family room is equally impressive with 9-foot ceilings, transom-accented walls of windows, and a wood-burning fireplace, delivering a bright, airy ambiance. At the heart of the home, the custom kitchen is both beautiful and functional, featuring stainless steel appliances, double ovens, and a spacious dinette framed by a wall of glass sliders. This space opens effortlessly to expansive patios and a breathtaking backyard, ideal for entertaining on any scale. Upstairs, the primary suite offers a private retreat with vaulted ceilings, a walk-in closet, dedicated office area, and French doors leading to a charming "Juliet" balcony. The spa-inspired bath is appointed with radiant heated floors, a Jacuzzi tub, and a separate shower. Three additional generously sized bedrooms complete the second level. The lower level is designed for leisure and entertainment, highlighted by a fully equipped home theater featuring a 105” projection screen, surround sound, and premium audio-visual components—bringing a cinematic experience into your home. The grounds transform into a true private oasis. Professionally designed with elegant Danish brick pavers, fieldstone retaining walls, and a heated saltwater in-ground pool, the outdoor setting is as impressive as the interior. A fully outfitted outdoor kitchen with built-in grill and refrigerator, along with separate garden and play areas, enhances the home’s versatility and appeal. Expansive patio areas are further elevated by an electric awning, integrated indoor and outdoor speakers, and LED landscape lighting—creating a seamless and inviting atmosphere for outdoor living and entertaining from day into evening. Additional features include Andersen windows throughout, central air, central vacuum, a full-house Generac generator, and a two-car garage. This exceptional offering presents a rare opportunity to enjoy luxury living in a tranquil, estate-like setting—just moments from beaches, vineyards, Stony Brook Village, and the region’s finest amenities.

4 Beds ⋅ 3 Baths ⋅ 988568 MLS

This distinguished custom Neo-Dutch Colonial is a masterclass in timeless architecture, exceptional craftsmanship, and exquisite detailing throughout. Gracefully set on 2.82 acres of exquisitely landscaped grounds in Head of the Harbor, the residence is designed with both elegance and comfort in mind, offering a seamless blend of expansive entertaining spaces and intimate everyday living—creating a truly refined North Shore retreat. A dramatic two-story entry sets the tone, welcoming you with a custom wood staircase and an immediate sense of scale and sophistication. The home’s gracious layout unfolds into an elegant formal living room featuring 9-foot ceilings and expansive picture windows that bathe the space in natural light while showcasing the surrounding grounds—creating a striking yet inviting setting for both formal gatherings and quiet moments. The formal dining room offers a seamless extension for entertaining, while the stunning family room is equally impressive with 9-foot ceilings, transom-accented walls of windows, and a wood-burning fireplace, delivering a bright, airy ambiance. At the heart of the home, the custom kitchen is both beautiful and functional, featuring stainless steel appliances, double ovens, and a spacious dinette framed by a wall of glass sliders. This space opens effortlessly to expansive patios and a breathtaking backyard, ideal for entertaining on any scale. Upstairs, the primary suite offers a private retreat with vaulted ceilings, a walk-in closet, dedicated office area, and French doors leading to a charming "Juliet" balcony. The spa-inspired bath is appointed with radiant heated floors, a Jacuzzi tub, and a separate shower. Three additional generously sized bedrooms complete the second level. The lower level is designed for leisure and entertainment, highlighted by a fully equipped home theater featuring a 105” projection screen, surround sound, and premium audio-visual components—bringing a cinematic experience into your home. The grounds transform into a true private oasis. Professionally designed with elegant Danish brick pavers, fieldstone retaining walls, and a heated saltwater in-ground pool, the outdoor setting is as impressive as the interior. A fully outfitted outdoor kitchen with built-in grill and refrigerator, along with separate garden and play areas, enhances the home’s versatility and appeal. Expansive patio areas are further elevated by an electric awning, integrated indoor and outdoor speakers, and LED landscape lighting—creating a seamless and inviting atmosphere for outdoor living and entertaining from day into evening. Additional features include Andersen windows throughout, central air, central vacuum, a full-house Generac generator, and a two-car garage. This exceptional offering presents a rare opportunity to enjoy luxury living in a tranquil, estate-like setting—just moments from beaches, vineyards, Stony Brook Village, and the region’s finest amenities.

76 Harbor Road, Head Of Harbor

$1,500,000

Classic charm meets modern living! Set high on a beautiful two-acre property, this timeless cedar Colonial sits proudly on a cul-de-sac in the village of Head of Harbor. The grand two-story foyer leads to spacious living and dining rooms, a chef’s kitchen with Viking gas range and granite countertops, and a cozy family room with fireplace. A sunroom provides year-round views of the sparkling in-ground pool, while covered front and rear porches invite outdoor living. The main level also includes a versatile bedroom/office with full bath and a mudroom. Upstairs are five additional bedrooms, including the expansive primary suite with walk-in closet and spa-like marble bath. With an attached two-car garage, full basement, central air, and separate hot water heater, this home offers comfort, convenience, and space in a prime setting.

6 Beds ⋅ 3 Baths ⋅ 907563 MLS

Classic charm meets modern living! Set high on a beautiful two-acre property, this timeless cedar Colonial sits proudly on a cul-de-sac in the village of Head of Harbor. The grand two-story foyer leads to spacious living and dining rooms, a chef’s kitchen with Viking gas range and granite countertops, and a cozy family room with fireplace. A sunroom provides year-round views of the sparkling in-ground pool, while covered front and rear porches invite outdoor living. The main level also includes a versatile bedroom/office with full bath and a mudroom. Upstairs are five additional bedrooms, including the expansive primary suite with walk-in closet and spa-like marble bath. With an attached two-car garage, full basement, central air, and separate hot water heater, this home offers comfort, convenience, and space in a prime setting.

18 Watercrest Court, Head Of Harbor

$1,400,000

Stunning 5BR/3BA Luxury Colonial on 2 Sprawling Acres Welcome to this exceptional home set on two beautifully landscaped acres located at the end of a cul-de-sac in the coveted Head of the Harbor neighborhood. Offering breathtaking views and unmatched privacy, this classic colonial seamlessly blends old-world charm with modern amenities. Inside, you’ll find an updated gourmet kitchen featuring granite countertops and premium hardwood floors that flow throughout the home. The spacious layout includes five bedrooms and three full bathrooms, perfect for both everyday living and entertaining. Step outside to your own private oasis, complete with an inground pool ideal for summer relaxation. Major updates include a newer roof and boiler, providing peace of mind for years to come. Additional highlights include a large private circular driveway and expansive property ideal for privacy lovers, outdoor enthusiasts, and those seeking a serene retreat just minutes from local conveniences. ALL THIS & PLENTY OF ROOM FOR MOM !!!!

5 Beds ⋅ 3 Baths ⋅ 936861 MLS

Stunning 5BR/3BA Luxury Colonial on 2 Sprawling Acres Welcome to this exceptional home set on two beautifully landscaped acres located at the end of a cul-de-sac in the coveted Head of the Harbor neighborhood. Offering breathtaking views and unmatched privacy, this classic colonial seamlessly blends old-world charm with modern amenities. Inside, you’ll find an updated gourmet kitchen featuring granite countertops and premium hardwood floors that flow throughout the home. The spacious layout includes five bedrooms and three full bathrooms, perfect for both everyday living and entertaining. Step outside to your own private oasis, complete with an inground pool ideal for summer relaxation. Major updates include a newer roof and boiler, providing peace of mind for years to come. Additional highlights include a large private circular driveway and expansive property ideal for privacy lovers, outdoor enthusiasts, and those seeking a serene retreat just minutes from local conveniences. ALL THIS & PLENTY OF ROOM FOR MOM !!!!

12 Briarwood Court, Head Of Harbor

$1,400,000

A rare opportunity in Head of the Harbor — over 4 acres of subdivided land offering unmatched potential and panoramic water views. This property includes multiple parcels: the main residence situated on one 2-acre lot, plus two additional parcels (Tax ID: 0801-006-00-01-00-001-002 and 0801-006-00-01-00-001-003), including a 2-acre buildable lot and a 0.3-acre private access road. The existing mid-century home is positioned to capture some of the best water views in the neighborhood and is being sold with full construction drawings and renovation plans already in place.

4 Beds ⋅ 4 Baths ⋅ 926537 MLS

A rare opportunity in Head of the Harbor — over 4 acres of subdivided land offering unmatched potential and panoramic water views. This property includes multiple parcels: the main residence situated on one 2-acre lot, plus two additional parcels (Tax ID: 0801-006-00-01-00-001-002 and 0801-006-00-01-00-001-003), including a 2-acre buildable lot and a 0.3-acre private access road. The existing mid-century home is positioned to capture some of the best water views in the neighborhood and is being sold with full construction drawings and renovation plans already in place.

30 Cordwood Path, Head Of Harbor

$1,340,000

BACK ON MARKET !! - ALL BINDERS ARE OFF, DEAL FELL THROUGH - HOME IS 100% AVAILABLE ! Welcome to 23 Bacon Road - The Best Value in the coveted Head of the Harbor ! This Elegant & Expansive Ranch-Style home is nestled on 2.38 beautifully landscaped acres in the heart of Head of the Harbor. Built in 1960 & designed by renowned builder Yablonski - This home offers over 5,300 square feet of exquisite living space, This one-of-a-kind gem features a first floor master bedroom, generous room sizes, a sun-drenched sun room and fully finished basement, perfect for entertaining or extended family. Each of the five oversized bedrooms offers comfort and privacy, with ample closet space throughout. The home seamlessly blends classic charm with with modern flavor and is surrounded by mature trees and rolling lawns in a tranquil setting. It's where luxury meets tranquility and every day feels like a vacation. Take advantage of this rare opportunity to own a distinguished property in an exceptional North Shore location.

5 Beds ⋅ 5 Baths ⋅ 881144 MLS

BACK ON MARKET !! - ALL BINDERS ARE OFF, DEAL FELL THROUGH - HOME IS 100% AVAILABLE ! Welcome to 23 Bacon Road - The Best Value in the coveted Head of the Harbor ! This Elegant & Expansive Ranch-Style home is nestled on 2.38 beautifully landscaped acres in the heart of Head of the Harbor. Built in 1960 & designed by renowned builder Yablonski - This home offers over 5,300 square feet of exquisite living space, This one-of-a-kind gem features a first floor master bedroom, generous room sizes, a sun-drenched sun room and fully finished basement, perfect for entertaining or extended family. Each of the five oversized bedrooms offers comfort and privacy, with ample closet space throughout. The home seamlessly blends classic charm with with modern flavor and is surrounded by mature trees and rolling lawns in a tranquil setting. It's where luxury meets tranquility and every day feels like a vacation. Take advantage of this rare opportunity to own a distinguished property in an exceptional North Shore location.

23 Bacon Road, Head Of Harbor

$1,300,000

Must see to appreciate! This Diamond Pristine home is tucked away in a charming and highly desirable country setting. There are many updates throughout this sprawling ranch-style residence - including an abundance of New Hi Hat Lighting in every room, Gleaming hardwood floors, and Fully finished basement level, with a bedroom and customized closets, and a huge storage area. The home offers a rare opportunity to enjoy refined living on 2.6 quiet, park-like acres—just moments from the charm and convenience of Stony Brook Village. It is Perfectly positioned near the tranquil waters of Stony Brook Harbor, Avalon Nature Preserve, local vineyards, and only a short drive to Stony Brook University and Hospital, this exceptional property blends a peaceful lifestyle with accessibility to key amenities. Travel in the opposite direction, and you are conveniently located in the heart of St. James, near the well-known St. James General Store (a thrill for all to visit and view the oldest and most historic and longest operating general store and post office in the nation). Smithtown Town beaches, Short Beach and Long Beach are well known for their peacefulness, and charming appeal of the Long Island Sound, with fishing, or just enjoying the calm waters and swimming, and forever all seasonal & perpetual scenic beauty. Here, There is a dog-walking park on the Stony Brook Harbor which is a peninsula and quiet, yet abounded by many grand estates. Designed with comfort and thoughtful craftsmanship, the home showcases an open and airy floor plan, enhanced by soaring vaulted ceilings, gleaming wood floors, and an abundance of natural light that fills the living spaces through oversized windows and sliding glass doors. At the heart of the home is a beautifully updated granite kitchen, featuring stainless steel appliances, a center island with seating, and a spacious dinette surrounded by windows—ideal for enjoying tranquil views and nature. A sliding door leads to a custom paver patio, providing seamless indoor-outdoor flow for everyday living and entertaining. The adjoining great room is both welcoming and spacious, complete with vaulted ceilings, a wood-burning fireplace, and custom built-in shelving—creating the perfect environment for gatherings or quiet evenings at home. The primary suite serves as a peaceful retreat, offering brand-new carpeting, elegant French doors that open to the outdoor entertainment area, a newly designed California Closet, and a spacious ensuite bath with a granite vanity, a jacuzzi tub, and walk-in shower. Two additional well-appointed bedrooms offer comfort and versatility, ideal for visitors, work-from-home space, or personalized use, while the full basement expands the home’s functionality with additional living space ideal for recreation, guest accommodations, or a home office. Ample storage is available throughout. A generously sized 2-car garage adds everyday convenience, and the property is equipped with an inground sprinkler system to keep the beautifully grounds maintained. Set amidst 2.6 acres of scenic, lush grounds in a highly desirable and professionally landscaped location, this home offers a timeless setting with a charming country ambiance. Whether enjoying the nearby harbor, strolling through nature preserves, or simply relaxing in your own backyard, this home presents a rare and wonderful lifestyle opportunity on Long Island’s North Shore.

3 Beds ⋅ 4 Baths ⋅ 874712 MLS

Must see to appreciate! This Diamond Pristine home is tucked away in a charming and highly desirable country setting. There are many updates throughout this sprawling ranch-style residence - including an abundance of New Hi Hat Lighting in every room, Gleaming hardwood floors, and Fully finished basement level, with a bedroom and customized closets, and a huge storage area. The home offers a rare opportunity to enjoy refined living on 2.6 quiet, park-like acres—just moments from the charm and convenience of Stony Brook Village. It is Perfectly positioned near the tranquil waters of Stony Brook Harbor, Avalon Nature Preserve, local vineyards, and only a short drive to Stony Brook University and Hospital, this exceptional property blends a peaceful lifestyle with accessibility to key amenities. Travel in the opposite direction, and you are conveniently located in the heart of St. James, near the well-known St. James General Store (a thrill for all to visit and view the oldest and most historic and longest operating general store and post office in the nation). Smithtown Town beaches, Short Beach and Long Beach are well known for their peacefulness, and charming appeal of the Long Island Sound, with fishing, or just enjoying the calm waters and swimming, and forever all seasonal & perpetual scenic beauty. Here, There is a dog-walking park on the Stony Brook Harbor which is a peninsula and quiet, yet abounded by many grand estates. Designed with comfort and thoughtful craftsmanship, the home showcases an open and airy floor plan, enhanced by soaring vaulted ceilings, gleaming wood floors, and an abundance of natural light that fills the living spaces through oversized windows and sliding glass doors. At the heart of the home is a beautifully updated granite kitchen, featuring stainless steel appliances, a center island with seating, and a spacious dinette surrounded by windows—ideal for enjoying tranquil views and nature. A sliding door leads to a custom paver patio, providing seamless indoor-outdoor flow for everyday living and entertaining. The adjoining great room is both welcoming and spacious, complete with vaulted ceilings, a wood-burning fireplace, and custom built-in shelving—creating the perfect environment for gatherings or quiet evenings at home. The primary suite serves as a peaceful retreat, offering brand-new carpeting, elegant French doors that open to the outdoor entertainment area, a newly designed California Closet, and a spacious ensuite bath with a granite vanity, a jacuzzi tub, and walk-in shower. Two additional well-appointed bedrooms offer comfort and versatility, ideal for visitors, work-from-home space, or personalized use, while the full basement expands the home’s functionality with additional living space ideal for recreation, guest accommodations, or a home office. Ample storage is available throughout. A generously sized 2-car garage adds everyday convenience, and the property is equipped with an inground sprinkler system to keep the beautifully grounds maintained. Set amidst 2.6 acres of scenic, lush grounds in a highly desirable and professionally landscaped location, this home offers a timeless setting with a charming country ambiance. Whether enjoying the nearby harbor, strolling through nature preserves, or simply relaxing in your own backyard, this home presents a rare and wonderful lifestyle opportunity on Long Island’s North Shore.

91 Harbor Road, Head Of Harbor

$1,150,000

A Rare Country Retreat on 3.5 Level Acres in Head of the Harbor Welcome to a truly special property that captures the charm and serenity of a classic country estate—gracious, private, and full of old-world appeal. Set on an incredibly rare and completely level 3.5-acre parcel, this beautiful setting offers a sense of space and tranquility that’s hard to find. Located just minutes from Long Island Sound beaches, local restaurants, charming village shops, and Stony Brook University, it’s a peaceful retreat that keeps you close to everything. This updated classic Colonial blends timeless style with modern comforts. Inside, you’ll find rich wood floors, custom millwork, and Andersen windows that fill the home with natural light. The inviting layout includes spacious formal rooms, a cozy wood-burning fireplace, and a lovely sunroom overlooking the grounds. The home has been thoughtfully upgraded with gas heating, central air, and updated baths—offering both charm and everyday convenience. The kitchen features white cabinetry, stainless steel appliances, gas cooking—perfect for everything from casual breakfasts to weekend entertaining. Upstairs, the large primary bedroom suite has been recently renovated and includes a stylish ensuite bath. Four additional bedrooms offer flexibility for guests or home office space. A full basement provides excellent storage, a laundry area, and the potential for even more finished living space. Outside, the property is a dream. The property offers a detached 1 car garage with additional potential room for guest quarters, a 2-stall stable, a sparkling inground pool with an updated liner and bluestone patios. The partially fenced yard, lush lawns, and mature trees complete the peaceful, estate-like setting. Whether you're seeking a year-round residence, a horse property, or a weekend escape, this special home offers space, character, and a truly unmatched location. The gracious home and its surrounding grounds evoke the peaceful charm of a timeless country estate.

5 Beds ⋅ 3 Baths ⋅ 884127 MLS

A Rare Country Retreat on 3.5 Level Acres in Head of the Harbor Welcome to a truly special property that captures the charm and serenity of a classic country estate—gracious, private, and full of old-world appeal. Set on an incredibly rare and completely level 3.5-acre parcel, this beautiful setting offers a sense of space and tranquility that’s hard to find. Located just minutes from Long Island Sound beaches, local restaurants, charming village shops, and Stony Brook University, it’s a peaceful retreat that keeps you close to everything. This updated classic Colonial blends timeless style with modern comforts. Inside, you’ll find rich wood floors, custom millwork, and Andersen windows that fill the home with natural light. The inviting layout includes spacious formal rooms, a cozy wood-burning fireplace, and a lovely sunroom overlooking the grounds. The home has been thoughtfully upgraded with gas heating, central air, and updated baths—offering both charm and everyday convenience. The kitchen features white cabinetry, stainless steel appliances, gas cooking—perfect for everything from casual breakfasts to weekend entertaining. Upstairs, the large primary bedroom suite has been recently renovated and includes a stylish ensuite bath. Four additional bedrooms offer flexibility for guests or home office space. A full basement provides excellent storage, a laundry area, and the potential for even more finished living space. Outside, the property is a dream. The property offers a detached 1 car garage with additional potential room for guest quarters, a 2-stall stable, a sparkling inground pool with an updated liner and bluestone patios. The partially fenced yard, lush lawns, and mature trees complete the peaceful, estate-like setting. Whether you're seeking a year-round residence, a horse property, or a weekend escape, this special home offers space, character, and a truly unmatched location. The gracious home and its surrounding grounds evoke the peaceful charm of a timeless country estate.

537 Moriches Road, Head Of Harbor

$960,000

Nestled in a serene, private setting, this spacious 4 bedroom, 3 full bath bilevel home combines a blend of comfort and nature while providing an opportunity to create your dream space. It offers a comfortable and functional 1st floor primary bedroom featuring an ensuite bath, two closets and sliding glass door that opens to views of the tranquil, wooded backyard. The main living area welcomes you with a cozy fireplace in the living room, a formal dining room and eat in kitchen. Downstairs, a generous family room with its own fireplace to relax and enjoy, a bedroom with a full bath and additional living space. This home provides a solid layout and great potential for customization. This home is in need of updating and is being sold as-is, making it a perfect opportunity for buyers looking to renovate and add their personal touch while taking advantage of a beautiful, serene 2 acre setting within the Smithtown School District.

4 Beds ⋅ 3 Baths ⋅ 975428 MLS

Nestled in a serene, private setting, this spacious 4 bedroom, 3 full bath bilevel home combines a blend of comfort and nature while providing an opportunity to create your dream space. It offers a comfortable and functional 1st floor primary bedroom featuring an ensuite bath, two closets and sliding glass door that opens to views of the tranquil, wooded backyard. The main living area welcomes you with a cozy fireplace in the living room, a formal dining room and eat in kitchen. Downstairs, a generous family room with its own fireplace to relax and enjoy, a bedroom with a full bath and additional living space. This home provides a solid layout and great potential for customization. This home is in need of updating and is being sold as-is, making it a perfect opportunity for buyers looking to renovate and add their personal touch while taking advantage of a beautiful, serene 2 acre setting within the Smithtown School District.

48 Farm Road, Head Of Harbor

$905,000

Welcome to 3 Nadia Court, a timeless New England-style Cape nestled on nearly 2.5 wooded acres in the exquisite village of Head of the Harbor. Tucked away on a quiet cul-de-sac, this 5-bedroom, 2-bathroom home offers the perfect blend of classic charm and serene privacy. Step through the front door into a large, welcoming foyer with original millwork that sets the tone for this warm and inviting home. Inside, you’ll find a spacious layout featuring a generous eat-in kitchen, formal living and dining rooms ideal for gatherings, and architectural details that speak to the home’s character and craftsmanship. With a one-car garage, expansive unfinished basement, and room to grow both indoors and out, this home offers endless possibilities. Whether you're looking to expand, entertain, or simply relax in nature, this private suburban retreat has it all.

5 Beds ⋅ 2 Baths ⋅ 896006 MLS

Welcome to 3 Nadia Court, a timeless New England-style Cape nestled on nearly 2.5 wooded acres in the exquisite village of Head of the Harbor. Tucked away on a quiet cul-de-sac, this 5-bedroom, 2-bathroom home offers the perfect blend of classic charm and serene privacy. Step through the front door into a large, welcoming foyer with original millwork that sets the tone for this warm and inviting home. Inside, you’ll find a spacious layout featuring a generous eat-in kitchen, formal living and dining rooms ideal for gatherings, and architectural details that speak to the home’s character and craftsmanship. With a one-car garage, expansive unfinished basement, and room to grow both indoors and out, this home offers endless possibilities. Whether you're looking to expand, entertain, or simply relax in nature, this private suburban retreat has it all.

3 Nadia Court, Head Of Harbor