Welcome to 149 Old Farm Road in Madison, Mississippi—an extraordinary gated estate featuring three residences and resort-level amenities throughout. The main home spans approximately 14,142± square feet and is truly a work of art, extensively renovated by the current owners with major upgrades including expansive new front-elevation windows, a rear putting and chipping green, refinished and replaced hardwood flooring throughout, and all new roofs, among many other improvements. Outdoor living rivals a private retreat, complete with a spa-style pool with sunbathing ledge, a regulation tennis court with basketball goal, and a whole-house generator for peace of mind. Inside, the main level offers a chef's kitchen with fireplace and abundant workspace, a keeping room, great room, recreation room, formal dining room, and wet bar—ideal for entertaining. The luxurious primary suite includes a private sitting area, a safe room that doubles as a walk-in closet, two additional large walk-in closets, and a spa-inspired bath with soaking tub, oversized shower, and private access to an outdoor shower and pool deck. Adjacent is a dedicated wellness and recreation wing featuring a golf simulator, sauna, steam room, gym, utility room, and bath. Upstairs you'll find four spacious bedrooms, four and a half baths, a kitchenette, utility room, media room, and an executive office with built-ins and balcony views overlooking one of the estate's ponds. The 1530+/- square foot guest house offers two bedrooms, two baths, a living room, kitchen, and half bath, ideally positioned beside the tennis court with views of the two ponds. The carriage house includes a four-car garage below, approximately 1287+/- square feet and a fully appointed residence above with two bedrooms, two baths, full kitchen, dining room, living room, laundry, and a balcony overlooking the tennis court and beautifully manicured grounds totaling 1450+/- square feet. For buyers seeking a one-of-a-kind property with virtually every amenity imaginable, this remarkable estate is a must-see. Proof of funds and or pre qualification documentation required prior to viewing. Seller may require listing agent to accompany showings.