4006 Stewart Rd Stevenson, MD 21153

Woodwynd – a timeless estate in the Greenspring Valley, available for the first time since 1969. Nestled on 10 bucolic acres on sought-after Stewart Road, Woodwynd offers unparalleled serenity, history, and elegance in the picturesque Greenspring Valley. Built circa 1890, this remarkable property seamlessly blends old-world charm with modern-day comforts.

Graced by mature specimen trees, apple orchards, and sweeping pastoral views, the main residence has recently been refreshed and features gleaming original hardwood floors throughout. Inside, the first floor features a large welcoming foyer, a private office, cozy den, formal dining room, and a spacious living room that opens to a sun-drenched stone porch and inviting sunroom. The heart of the home is a dramatic two-story great room off of the kitchen. It boasts a soaring 28-foot vaulted ceiling and a striking stone fireplace—perfect for gatherings year-round. The large kitchen with breakfast area, plus a mudroom, powder room, and full bath, complete the main level.

Upstairs, the second and third floors offer six well-appointed bedrooms, four full baths, a laundry room, and a flexible bonus space. The serene primary suite includes access to a charming sitting area or sleeping porch, ideal for a home office or possible expanded walk-in closet.

Outside enjoy resort-style living with two koi ponds, a 40-foot pool, hot tub, and a stone patio with pergola—perfect for entertaining under the stars or eating al fresco.

A separate guest house features two bedrooms, a full bath, living room, kitchen, and sunroom leading to a wood deck, ideal for visitors. A large barn and carriage house adds further charm and utility to the property.

Woodwynd is more than a home—it’s a rare opportunity to own a legacy property in one of Maryland’s most coveted and convenient settings. Bring your vision and create your dream estate in Greenspring Valley.