4408 Old North Rd
Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!
Listing Information
Facts & Features
Location
Community Information
Architecture
Features & Amenities
Property Features
Square Footage
Tax & Financial Information
Schools
Southold Elementary School
Assigned school for this home
Southold Junior-Senior High School
Assigned school for this home
Greenport Elementary School
Mattituck-Cutchogue Elementary School
Shelter Island School
Greenport High 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 |
|---|---|---|
| 09/01/2026 | Price change | $1,299,000 |
| 07/13/2026 | Listed for sale | $1,385,000 |
Listed by Kristy B. Naddell · Douglas Elliman Real Estate · 6313548100
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 9, 2026 at 7:13 AM | Source: OneKey MLS | MLS#: 1023884

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