Welcome to Chiswell

Greenwood, VA

A historic Jeffersonian estate nestled in the Virginia countryside, Chiswell Farm & Winery invites guests to delight in locally-crafted vintages, panoramic views, and warm hospitality.

Chiswell welcomes guests ages 21+

Aerial view of Chiswell Farm & Winery

Enjoy Chiswell Wine

Chiswell spring/summer specialty drink: strawberry citrus sangria with mint

Strawberry Citrus Spritzer

Made with rosé, fresh strawberries, lemon-lime seltzer, and mint. Try our refreshing seasonal sip this spring!

Wine tasting flight - 4 wines placed on an ash oak platter

Tasting Flights

Build your own wine flight or choose from one of our recommendations.

Crown Club

Crown Club

Our Chiles Family Orchards wine and celebration membership is about sharing the fruits of Virginia Wine Country with a tight-knit community.

A group of six wines outdoors with award medals

Award-winning Wines

We are proud to announce that six of our wines were recognized in the 2026 Virginia Governor’s Cup, including two gold medals!

Our 2023 Meritage and 2023 Merlot both took home gold medals, with silver medals being awarded to our 2021 Meritage, 2022 Petit Verdot, 2023 Petit Manseng, and 2024 Sauvignon Blanc.

It’s a privilege to be recognized again after our gold medals in 2025’s Governor’s Cup and Monticello Cup. Order a Governor’s Flight to sample our most recent award winners!

Wine Guides

We look forward to your visit!