Welcome to Sleepy Hollow a charming Longwood community known for its tree lined streets and generous lot sizes. Introducing 102 Ichabod Trail, nestled on a little over a 1/2 of an acre of lush landscaped grounds, offering both privacy and the perfect canvas for gardening enthusiasts to show off their green thumb. This well built 4 bedroom, 2.5 bath block home boasts a spacious and versatile layout. The formal living and dining rooms feature warm wood flooring. The kitchen includes ample cabinet and counter space, stainless steel appliances including a Bosch dishwasher and LG refrigerator both replaced in 2024, and opens to an oversized family room. Enjoy the cozy brick fireplace, vaulted ceilings, and expansive picture windows overlooking the serene backyard and pool. The primary suite features updated French doors that lead directly to the screened in pool area, and the remodeled ensuite bathroom offers modern finishes, abundant storage, and a new walk in shower. Recent updates and features include: Roof (2022), Pool resurfaced with new tile & pool pump (2022), Whole house propane GENERAC generator (2024), Front door & exterior lights (2025), Two zone A/C system (bedroom's side unit replaced in 2019), Central vacuum system, Replumbed plumbing, Fully fenced yard with large side gate for easy access, Electric powered shed for extra storage. Community park incudes tennis, pickelball & playground. This home is situated in a top rated school district and provides easy access to I 4, the Altamonte Mall, shopping, and dining. While it may benefit from some imaginative cosmetic updates, the solid structure, spacious lot, and numerous improvements make it a fantastic opportunity for any family.