HIGHEST AND BEST DEADLINE: 8pm on 7/21/2026. Welcome to 255 Tanglewood Circle, a beautifully maintained residence tucked away on a quiet cul-de-sac offering a private setting in North Milford. Professional landscaping and a circular driveway creates timeless curb appeal. Step inside the welcoming foyer to discover a thoughtfully designed main level. The spacious living room features a fireplace and bay window, flowing seamlessly into the formal dining room. The home's kitchen is updated with granite countertops, stainless steel appliances, center island w/seating and built-in desk. Sliders lead to a private deck overlooking the yard. The laundry area is located off the kitchen. The floor plan offers a primary suite with updated en suite bath, an additional two bedrooms outfitted with California Closets, and beautifully updated full bathroom. A generous family room with cathedral ceiling, full bath and walk-in closet provides the option for an additional primary suite, guest room, or multi-generational living. A cozy den adds even more versatility. The lower level offers a private two-bedroom in-law apartment. An unfinished basement area provides additional storage. A second driveway leads to the attached two-car garage. The fully fenced backyard offers room to enjoy the outdoors with privacy between neighboring homes. This home offers the perfect blend of comfort and thoughtful design to evolve with your lifestyle