This wonderfully maintained home on a cul-de-sac just over the Trumbull line in the beautiful town of Monroe offers the perfect blend of privacy and convenience-close to restaurants, shopping, highways, and just 20 minutes to CT's shoreline and train stations. Thoughtfully designed for both everyday living and entertaining, the home features 2 fireplaces, a sunroom, wine room, expansive finished lower level PLUS a backup generator, underground sprinklers and more! A gracious entry welcomes you with two spacious sitting rooms with fireplaces on either side and a grand staircase. The updated kitchen features solid wood cabinetry, granite countertops, updated appliances, and an island with seating plus room for a dining table, all flowing seamlessly into the sunroom with radiant heated floors and access to the rear deck. The large dining room also offers sliders to the deck. The main level is complete with a private office, powder room, and a spacious mudroom with built-ins, laundry, and an additional powder room off the garage. Upstairs offers 4 generously sized bedrooms, a newly renovated hall bath with double vanity, and a spacious primary suite with a beautifully updated bath featuring dual sinks, built-in storage, and a large walk-in shower. The flat 1-acre property includes a shed, gazebo, new Trex deck, fire pit area, and a potential pool site-creating a true backyard retreat.