Welcome to 556 N Windsor Avenue, a gracious 1902 Colonial offering exceptional space, character and versatility in the heart of Brightwaters Village. From the moment you enter the charming entry parlor and continue into the welcoming foyer with its grand staircase, the home immediately draws you in with its warmth, character and inviting sense of space. Designed with entertaining and everyday living in mind, the main level offers beautifully proportioned spaces throughout. The oversized living room provides plenty of room for multiple seating areas and is anchored by a wood-burning fireplace with a beautiful mantel and custom built-ins. Crown and base molding, recessed lighting and architectural details add to the room's character, while multiple openings create an easy connection to the adjoining wraparound den. Filled with windows and natural light, the enclosed wraparound den offers an inviting space to relax and entertain and features built-ins, a bar area with wine refrigerator, an integrated sound system and direct access to the backyard. At the heart of the home is the spacious chef's kitchen with radiant heated floors, rich cherry cabinetry, quartz countertops, stainless steel appliances, a breakfast bar with pendant lighting and a six-burner Viking range with center grill and oversized hood vented to the exterior. The kitchen opens to the large dining room with hardwood floors, a bay window, tray ceiling and sliding glass doors to the deck and yard. Just off the kitchen, a convenient mudroom with radiant-heated tile flooring provides direct backyard access and incorporates a perfectly placed laundry nook with additional storage. Completing the main level is a beautifully updated full bath with a classic clawfoot tub, pedestal sink and timeless tilework, along with a generously sized office with extensive closet storage. Currently used as a home office, this versatile room also offers the flexibility of a possible fifth-bedroom or comfortable guest space. Upstairs are four bedrooms, including a spacious primary bedroom with separate sleeping and sitting areas, generous closet space and a decorative fireplace mantel. An oversized updated full bath with tiled shower completes the second level and pull-down stairs from the hallway provide convenient access to the attic for additional storage. The partial basement provides even more storage and includes a cedar closet and workshop area. Outdoors, the home's inviting living spaces continue with a wood deck, paver patio, large fenced yard and established organic vegetable and flower gardens, creating a wonderful setting for outdoor dining, entertaining, gardening or simply relaxing. A newly repaved Belgian block-lined driveway provides abundant parking and leads to the detached two-car garage. Additional features include central air conditioning, two-zone natural gas heat, public sewers and a multi-room sound system with indoor and outdoor speakers. Offering four bedrooms plus a flexible first-floor office/possible fifth bedroom and two full baths, this move-in-ready home brings together exceptional space, character and the sought-after Brightwaters Village lifestyle. Enjoy close proximity to Wohseepee Park, Village shopping and dining, schools and major roadways, along with resident amenities including the Village beach, canal docking, Brightwaters lakes, tennis, dog park, private garbage collection and snow removal. Just minutes from Downtown Bay Shore, the Fire Island Ferries and Robert Moses State Park, 556 N Windsor Avenue offers the opportunity to enjoy all that Brightwaters and the Great South Bay lifestyle have to offer.