68 Chestnut St
Hillside Retreat on .82 Private Acres | New Roof, Boiler & Trex Deck Discover a distinctive 4-bedroom, 3-full-bath, approximately 3,000-square-foot hillside home set on .82 private acres at the end of a long, private driveway. Built in the 1990s and designed into the natural grade of the property, this unique multi-level residence offers architectural character, versatile living space, modern updates, and a peaceful, wooded setting. The main living level features an open-concept layout with soaring ceilings and abundant natural light. The kitchen with granite countertops flows into the dining area and living room, creating an inviting space for everyday living and entertaining. The primary bedroom features a full bath and ample closet space. An additional bedroom and full bath complete this level. The ground level offers two additional bedrooms, a den or living area, and a full bath. Thanks to the home's hillside design, this level functions as a true ground-level living space rather than a traditional basement. The flexible layout offers a variety of possibilities for a home office, guest accommodations, recreation room, gym, or media room. Notable updates include a roof approximately 4 years old, a boiler approximately 3 years old, and a new Trex deck. Additional features include granite countertops, an electric vehicle charger, a sprinkler system, a 1.5-car garage, and oversized parking. Enjoy the outdoors from the new Trex deck overlooking the wooded surroundings. The expansive backyard offers ample room to create an outdoor retreat, with possibilities for a pool, patio, gardens, play area, and outdoor entertaining space. An existing patio with a retaining wall adds to the property's outdoor potential. Conveniently located within the Mount Sinai School District and close to downtown Port Jefferson Village, with its shops, restaurants, and golf, this property combines a secluded setting with access to nearby amenities. Distinctive hillside architecture, approximately 3,000 square feet of versatile living space, significant updates, and .82 private acres make this a unique opportunity to enjoy space, privacy, and outdoor potential.
Listing Information
Facts & Features
Location
Community Information
Architecture
Features & Amenities
Property Features
Square Footage
Tax & Financial Information
Schools
Boyle Road Elementary School
Arrowhead Elementary School
Mount Sinai Elementary School
Earl L Vandermeulen High School
Comsewogue High School
Terryville Road School
John F Kennedy Middle School
Norwood Avenue School
School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.
Historical Data
Price History
| Date | Event | Price |
|---|---|---|
| 10/20/2026 | Price change | $899,000 |
| 09/25/2026 | Listed for sale | $969,000 |
Listed by Irina V. Renner · R & R Duo Realty Inc · 5164450675
Listing information provided exclusively 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 deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.
Last Updated: October 27, 2026 at 10:30 PM | Source: OneKey MLS | MLS#: 1053741

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