Step into a special piece of North Fork history. Originally the Main Bayview Schoolhouse, this distinctive, furnished, Southold property has been thoughtfully converted into a welcoming five-bedroom, two-bath country residence that retains the warmth, charm and character of its past.
Offering approximately 2,000 square feet of furnished living space, the home comfortably accommodates up to nine occupants. The inviting living room features a wood-burning stove, while the finished lower level provides flexible additional space for recreation, studying, creative pursuits or a home office. A private fenced yard offers a peaceful setting for enjoying the changing North Fork seasons. Pets are welcome, subject to lease terms.
Conveniently situated near Southold Village, Cedar Beach and Goose Creek Beach, the home is also close to North Fork wineries, farm stands, shops and acclaimed local restaurants.
Available as an academic-year rental from September 15, 2026 through June 2027 at $4,200 per month, plus utilities and other lease-related charges. An academic rental provides housing during the traditional school-year period without requiring a full 12-month lease—an appealing option for anyone seeking an extended seasonal residence in Southold.
Shorter monthly stays are also available during this period, subject to availability, with rates and terms based on the length and dates of occupancy.
The property is located within the Southold Union Free School District. Prospective tenants should independently confirm all school-registration and residency requirements directly with the district.
Maximum occupancy: nine. Rental Permit No. 0336.