101 Henderson Street

A 5-bedroom, 5.5-bath single family residence in Woodstock.

Just steps from the vibrant heart of Downtown Woodstock, this fully custom-built home offers a rare blend of luxury, privacy, and true walkability in one of the area’s most energetic and beloved communities. Set on more than half an acre, the property delivers the space and comfort of a private estate while placing you just moments from Woodstock’s acclaimed restaurants, boutique shops, local parks, live music, and year-round festivals.

Inside, the home reflects thoughtful design and craftsmanship throughout, with open living spaces. The chef’s kitchen serves as the heart of the home, featuring an oversized island, premium appliances, and seamless flow into the main gathering spaces. Natural light fills the interiors, highlighting custom details and beautifully designed living areas that connect effortlessly to the outdoor spaces.

The home offers five spacious bedrooms and four full bathrooms, along with flexible spaces designed for modern living — including a dedicated office for working from home and a private home gym. Tucked above it all, a rooftop deck provides an elevated retreat and a unique vantage point to enjoy sunset views, morning coffee, or evening gatherings under the stars.

Step outside and the lifestyle truly comes to life. The courtyard-style backyard feels like your own private resort, anchored by a saltwater pool and hot tub that create the perfect setting for warm summer afternoons and relaxed evenings. Just beyond, a fully appointed pool house adds incredible flexibility to the property, complete with an additional bedroom, one and a half bathrooms, and a game room — ideal for hosting guests, extended stays, or creating a separate space for entertaining.

Homes offering this level of custom craftsmanship, outdoor living, and walkability to Downtown Woodstock are incredibly rare. Here, you’ll experience the best of both worlds — a one-of-a-kind custom residence with room to spread out, paired with the dynamic, walkable lifestyle that makes Downtown Woodstock one of the most exciting places to live in Cherokee County.

Property details

Where it sits

Mortgage estimate

An estimate of your monthly payment, including principal, interest, taxes, and insurance. Property taxes for this listing are $8,914 annually.

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