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$1,975,000
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
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
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
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
$1,340,000
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
$960,000
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

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.