279 Middle Haddam Road Set in one of Portland's most picturesque locations with sweeping Connecticut River views, this beautiful expanded Cape Cod tells a story of timeless craftsmanship, thoughtful updates, and distinctive lifestyle amenities. The custom kitchen showcases custom cabinetry with bright quartz countertops and an expansive island designed for gathering and entertaining. Warmth and character carry throughout the home with two Natural stone fireplaces, wainscoting, crown molding, hardwood floors, and a cherry-paneled library or first-floor office. The remodeled primary suite offers a refined retreat. The walk-in attic provides valuable additional storage. A fully town-approved accessory apartment creates flexible space for extended living and guests, with a proven history of rental income. Outdoors, the property setting is its defining feature. Enjoy a heated inground gunite pool surrounded by a riverview setting made for relaxation. Car enthusiasts, collectors, and hobbyists will appreciate the attached two-car garage plus the post-and-beam barn offering storage for multiple cars, with four total garage bays or livestock options with direct access to the airline trail, making it limitless. This is an ideal spot. Solar panels add efficiency, coupled with a new furnace, air conditioning ductwork, and updated air conditioning. The new roof completes this rare Portland offering, where classic home charm meets modern comfort and standout utility.