Oakwood Estate: A Historic Masterpiece Reimagined

Welcome to 1221 Oakwood Street, a true Bedford showpiece where historic architecture meets modern luxury living. Originally built in 1860, this remarkable estate has been completely renovated by Custom Structures with today’s lifestyle and entertaining in mind, offering an impressive 5,670 square feet of thoughtfully designed living space. From the moment you arrive, the home’s presence and craftsmanship make a lasting impression. Inside, grand living spaces blend historic charm with modern comfort. The home features two stunning primary suites, each designed as a private retreat with luxurious wet rooms with spa-inspired finishes and large walk-in closets. Three additional bedrooms share a spacious bath with triple sinks, while a convenient half bath on the main level serves guests. Two laundry rooms on each level offer convenience. The gourmet kitchen is truly a chef’s dream, highlighted by a striking 48-inch Italian range, generous prep space, and an oversized dining area large enough to host two full-size dining tables—perfect for holiday gatherings or memorable dinner parties. The great room offers the perfect place to relax, featuring cathedral ceilings and gas log fireplace. A cozy bonus space with gas fireplace, impressive stone wall and a spanish tile floor can be a game/play room, home office, hobby room or a swanky bar. Downstairs, the expansive basement sets the stage for an unforgettable gentleman’s den, anchored by a historic brick fireplace and access outside to the pool area. An adjacent storage room offers incredible flexibility for a private library, wine cellar, or humidor room. Step outside and discover your own private resort. An 8-foot-deep saltwater pool surrounded by hand-laid flagstone patios creates the ultimate outdoor retreat. The backyard also features an outdoor firepit and a plumbed outdoor kitchen ready for installation, making the space ideal for entertaining under the stars. Additional highlights include two paved driveways, a 3-car garage, beautifully landscaped grounds, large raised garden beds, and a fenced park-like backyard backing to a serene wooded area that provides both privacy and room to enjoy the outdoors. Homes of this scale, character, and modern renovation rarely come available in Bedford. 1221 Oakwood Street is more than a home—it’s a lifestyle.