Located in the heart of Kingston's historic Stockade District, this beautifully restored Greek Revival brick home with Italianate details, blends timeless character with thoughtful modern updates. Originally built in 1885 for Joseph C. Wyckoff, who at the time was the principal of Kingston Academy, located on Academy Green. The home offers 4,200 square feet across four finished levels; 5-bedroom, 3 Full/3 Half Bathrooms providing generous living spaces that are equally suited for entertaining and everyday life—all just a short stroll from Uptown Kingston's vibrant restaurants, shops, galleries, and cafes. Step inside to discover soaring ceilings, elegant crown moldings, hardwood floors, and a stunning marble fireplace mantel that reflect the home's rich history. The current owners have thoughtfully updated the interiors with carefully selected designer finishes, including Papier wallpaper and custom Soho Home lighting that add warmth and sophistication throughout. The main level features a generous living room, a sunroom with three exposures of windows that fill the space with natural light, a formal dining room, and a custom chef's kitchen appointed with a Wolf range, Sub-Zero refrigerator, custom cabinetry, and a spacious pantry with a wine cooler. A powder room and office with ensuite half bath complete this level. Upstairs, the second floor offers four spacious bedrooms - including the primary suite - which includes an ensuite bath and walk-in closet. Two bedrooms are currently used as a home office and music room. A separate bedroom wing, complete with its own full bath and a California Closets-designed dressing room (formerly bedroom), offers an ideal second primary suite or private guest space. On the third floor, a charming two-room studio with a half bath and custom cedar storage closet provides endless possibilities. The walk-out lower level adds even more versatility - featuring abundant storage, a private home gym, a three-person infrared sauna, a full bathroom, and an additional pantry. An adjacent three-season room offers a wonderful space for indoor-outdoor dining. The exceptional outdoor living space sits on a spacious double lot and has been transformed into a private backyard oasis. Mature landscaping and new custom plantings grace both the front and back yards. A stately arborvitae border in the front lends beautiful curb appeal and year-round privacy. French doors from the dining room open to a cozy deck that's perfect for morning coffee with stairs that lead to a stone patio below - a generous space for lounging and dining, complete with brick wood-burning grill. The expansive backyard, fully enclosed with cedar fencing, provides plenty of room to relax, entertain, or create your retreat with the addition of a pool or outbuilding. Behind its historic exterior, the home has been extensively updated for modern comfort and efficiency. Improvements include a 7-zone Mitsubishi mini-split system, high-efficiency oil heat, updated plumbing, new 200+ amp electrical service, an electric vehicle charger, and a newly paved asphalt driveway that offers convenient off-street parking. Just two blocks from Uptown Kingston's restaurants, boutiques, farmers market, and cultural attractions, this is a rare opportunity to own a truly move-in-ready historic home with exceptional privacy, modern amenities, and one of the neighborhood's most desirable locations.