Dana Robyn Chubb
Licensed Real Estate Salesperson, PSA
PSA, REALTOR®
Delhi, NY
Office: (607) 746-7400 (518) 522-6779
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89 Harbor Road, Head of the Harbor, NY 11780

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Property Description

A Rare Waterfront Sanctuary in the Village of Head of the Harbor. For the first time since it was built more than half a century ago, this remarkable waterfront property is being offered for sale. Privately set on 2.75 acres overlooking Stony Brook Harbor, 89 Harbor Road has remained under its original ownership since its creation and is defined by privacy, natural beauty and an extraordinary connection to the surrounding landscape. With 200 feet of waterfront, sweeping views extend across the pristine harbor toward Nissequogue, and Long Island Sound beyond, while private steps lead directly to the beach and water below, where a substantial stone riprap revetment protects the shoreline.A long and winding drive passes through a wooded landscape, leading to a broad opening with a light-filled residence framed by majestic oaks and a backdrop of water and sky. Upon arrival, there is an immediate sense of having left the hustle and bustle of the outside world behind-a peaceful sanctuary where the landscape, changing tides and natural beauty of the harbor become part of everyday life.Designed by architect Geysa Sarkany, the approximately 4,600-square-foot residence was conceived around its remarkable setting. The home was designed to look outward, with walls of glass creating a seamless connection between the interiors and the water and landscape beyond. Beneath this openness is a home of substantial construction, engineered and built with solidity and permanence. From the principal living spaces, kitchen and covered deck, the architecture continually draws the eye outward, framing individual views of the sky, shoreline and ever-changing harbor. Thoughtfully placed windows and glass, cypress siding and natural materials further connect the architecture to its surroundings, while 5 bedrooms and 3.5 baths across three levels provide substantial living space.Here, no two days on the harbor are quite the same. The tides rise and recede, revealing winding channels and broad tidal flats. Herons wander the shoreline while ospreys and eagles soar overhead, and sailboats, kayaks and paddleboarders quietly pass below. Summer brings long evenings on the covered deck and breathtaking sunsets over the water, as the sky and harbor take on an ever-changing palette of color and texture. In autumn, the marsh grasses turn from green to gold, while the shifting light and changing winds transform the landscape.The connection to the waterfront extends beyond the views, with direct beach and harbor access for kayaking, paddleboard

89 Harbor Road | MLS# 1054624

This single family home located at 89 Harbor Road, Head of the Harbor, NY 11780 is currently listed for sale with an asking price of $1,999,000. This property was built in 1974 and has 5 bedrooms and 3 full and 1 partial baths with 4600 sq. ft. Harbor Road is located within the Smithtown school district. Search Head Of The Harbor real estate on dana-chubb.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Partially Finished, Storage Space, Walk-Out Access
Cooling: Central Air
Fireplaces: 2
Heating: Baseboard, Forced Air, Oil
Home Style: Contemporary
Lot Size: 2.75 Acres
Taxes: $39,785
Year Built: 1974

Amenities

First Floor Full Bath
Beamed Ceilings
Breakfast Bar
Built-in Features
Cathedral Ceiling(s)
Central Vacuum
Eat-in Kitchen
Entrance Foyer
Formal Dining
High Ceilings
High Speed Internet
Kitchen Island
Natural Woodwork
Open Kitchen
Recessed Lighting
Tile Counters
Tray Ceiling(s)
Walk-In Closet(s)
Washer/Dryer Hookup

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Oven, Electric Range, Exhaust Fan, Microwave, Refrigerator, Washer, Tankless Water Heater
Attic: Partial
Beach Rights: Y
Days on Site: 7
Exclusions: See Listing Agent
Exterior: Batts Insulation, Brick, Cedar, Frame
Fireplace Features: Family Room, Living Room, Wood Burning
Fireplace Y/N: Yes
Flooring: Hardwood, Tile
Formal Dining: Yes
Frontage: 200
Heating Zones: 7
Included In Taxes: Trash
Laundry: Electric Dryer Hookup, In Hall, Washer Hookup
Lot Features: Back Yard, Front Yard, Part Wooded, Private, Secluded, Stone/Brick Wall, Views, Waterfront, Wooded
Number Of Kitchens: 1
On Market Date: 2026-10-03
Parcel Number: 0801-002-00-01-00-013-000
Parking Features: Driveway
Patio And Porch: Deck
Rental Term: Monthly
Rooms Total: 12
Sewer: Cesspool
Skylight: Y
Utilities: Cable Connected, Electricity Connected, Phone Connected, Propane, Trash Collection Public
Water: Well
Waterfront Features: Beach Access, Water Access, Waterfront
Window Features: Bay Window(s), Casement, Double Pane Windows, Floor to Ceiling Windows, Oversized Windows, Screens, Skylight(s), Wall of Windows, Wood Frames
Wooded: Yes

Local Schools

High School: Smithtown High School-East
Middle School: Nesaquake Middle School
Elementary School: St James Elementary School
School District: Smithtown

Estimate Your Payment

Estimated Payment

$ 8,347.37 per month $4,448.91 Principal & Interest $3,315.42 Property Tax $583.04 Homeowner's Insurance

Change Payment Information

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years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Daniel Gale Sothebys Intl Rlty
Agency Contact: 631-584-6600

Shown By

Agent Name: Dana Robyn Chubb
Agent Phone: (518) 522-6779
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/05/2026. The listing information on this page last changed on 10/05/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 10/05/2026 5:49:29 AM EST) or Global MLS (last updated Sun 10/04/2026 8:12:41 AM EST) or New York State Alliance MLS (last updated Mon 10/05/2026 2:34:53 AM EST) or Hudson Valley Catskill Region MLS (last updated Mon 10/05/2026 12:11:11 AM EST) or OneKey MLS (last updated Mon 10/05/2026 1:45:17 AM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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