Offered for the first time in four decades, 33 Club Circle presents a rare opportunity in one of Stamford's most sought-after neighborhoods, nestled at the end of a cul-de-sac within the desirable Club Road community. Lovingly maintained and thoughtfully expanded over 40 years, this distinguished 5-bedroom, 3.5-bath Colonial showcases timeless craftsmanship, classic charm, and enduring quality. Inside, pristine hardwood floors flow through the living and dining rooms, while a stunning fieldstone fireplace anchors the spacious family room, creating a warm and inviting atmosphere. The flexible floor plan offers exceptional versatility, ideal for multigenerational living or hosting guests with ease. The expansive primary suite features a gas fireplace, oversized walk-in closet, and a beautifully appointed bath - double vanity and tiled shower. The eat-in kitchen opens to a deck overlooking a heated in-ground gunite pool with a pool house complete with kitchenette and half bath, all set within a professionally landscaped, private backyard retreat. A patio provides the perfect setting for outdoor dining, entertaining or quiet relaxation. Partially finished lower level provides versatile bonus space perfect for a playroom, home gym, or media lounge. Ideally located just minutes from downtown Stamford, Metro-North, parks, Sterling Farms Golf, shopping, beaches, this home offers the perfect blend of convenience and tranquility. A truly rare offering ready to welcome its next chapter!