5 Virginia Waterfront Estates, Vineyards, and Country Luxury Retreats

Along the water’s edge in prestigious Alanton, this custom residence unfolds across a 1.2-acre waterfront sanctuary with deep-water living at its center. An open floor plan connects a chef’s kitchen finished with quartz surfaces to a breakfast nook wrapped in shimmering water views. For evenings in, a sunken living room pairs a gas fireplace with a relaxed sense of retreat, while a refined dining room offers a more formal rhythm. Entertaining continues in an impressive media room and bar designed for easy gathering. The primary suite reads like a private resort, complete with a sitting area, spa-inspired bath, and a generous walk-in closet, complemented by two additional en-suites. Outside, a breathtaking pool with cascading waterfalls and covered porches frames the setting, with a dock and lift extending life onto the deep water. A detached three-car garage includes a full apartment above.

Along the York River in Williamsburg, this Tudor-inspired estate unfolds across 11.87 private acres with over 600 feet of waterfront frontage and panoramic river views. The setting feels quietly removed, yet the composition is decidedly refined—an approach that carries through to the home’s elegant living spaces, designed to keep the landscape in constant view. A luxurious primary suite adds a sense of retreat, while English gardens bring structure and softness to the grounds, inviting slow mornings and unhurried evenings outdoors. With its remarkable privacy and long ribbon of shoreline, the property offers a rare daily rhythm shaped by water, gardens, and open sky.

Set amid the pastoral beauty of Virginia’s Northern Neck, Good Luck Cellars unfolds as an award-winning winery and event destination spanning 136 acres. The offering encompasses 25 acres of cultivated vines alongside a tasting room, production facilities, and a thoughtful mix of event and residential spaces, complemented by farm buildings and included equipment for a truly turn-key transition. Known as much for its role as a wedding venue and gathering place as for its wines, Good Luck has earned numerous gold, silver, and bronze medals in Virginia and beyond, including the Virginia Governor’s Cup Gold. A private landing strip for small aircraft adds a rare layer of access and intrigue. Thirteen winery dogs patrol the grounds year-round—local celebrities featured in magazine articles and regional network news. Close to The Tides Inn and the town of Kilmarnock, it’s poised for the next chapter in agri-tourism and wine experiences.

From its private cul-de-sac setting in Banbury Cross Reserve, this all-brick French transitional residence offers a quietly refined approach to Middleburg living, framed by protected field and woodland views. Inside, wide-plank white oak floors run beneath soaring 10-foot ceilings, creating a sense of volume that still feels warm and grounded. The chef’s kitchen is designed for everyday ease and polished entertaining alike, centered around a quartz island and outfitted with Sub-Zero, Wolf, and Cove appliances. Mahogany doors add a tailored, material-rich note throughout. For unwinding, the primary suite is arranged as a true retreat, complete with a sitting room and spa bath. Move-in ready with no wait for new construction, the experience here is equal parts privacy, craftsmanship, and calm.

Size: 3.00 acres

Along the water’s edge on the York River, Carmines Island is a rare private island estate spanning 4+ acres, where panoramic water views shape the rhythm of daily life. The home balances gathering and retreat, anchored by a chef’s kitchen and a grand hearth that lends warmth and presence to the main living spaces. A primary suite balcony extends the experience outdoors, offering a quiet vantage point over the river. For afternoons that drift into evening, a private pier invites easy time on the water—fishing, boating, or simply watching the light change across the horizon. Set in Hayes and just minutes from Gloucester, the setting feels both connected and distinctly removed, designed for privacy without losing a sense of place.