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5 Virginia Waterfront Estates and Landmark Event Properties

By Awais Manzoor

1 min read

privacy, acreage, and settings that feel difficult to replicate. From Virginia Beach waterfront sanctuaries with sweeping views and deep-water living to a classic 1959 brick-and-slate James River estate, each residence is shaped for gathering as much as retreat. The collection then widens into experience-driven ownership, including a 135.89-acre Northern Neck winery and event venue and a refined Western-style luxury event estate in Franklin County.

Private Waterfront | $5,800,000

1242 N Inlynnview Rd Virginia Beach VA 23454
1242 N Inlynnview Rd, Virginia Beach, VA 23454
Heather Sterling
LISTING AGENT:
Heather Sterling

Along the water’s edge in Virginia Beach, this redesigned estate unfolds across 3+ private, meticulously maintained acres with breathtaking, unobstructed views to the Lesner Bridge. Positioned well behind neighboring homes, it offers a rare sense of privacy and open space seldom found on the waterfront. Inside, soaring ceilings and vast water views set the tone, while a chef’s kitchen with Thermador appliances is supported by a butler’s pantry with sink and commercial refrigerator. A spectacular great room anchors daily life and entertaining with an 85-inch retractable TV and surround sound. The primary suite is described as a spa-inspired retreat. Outdoors, expansive patios and a sprawling lawn run to the water’s edge, complemented by the longest dock on the point, deep-water access at low tide, a 10,000-lb boat lift, dual jet ski lifts, and 240V dock power—finishing with a certified, fortified roof overhead.

Price:
$5,800,000
Size:
6,300 sq ft
Contact:
Heather Sterling, Howard Hanna Real Estate Svcs., 757.724.1733
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Deep-water Coastal Estate In Prestigious Alanton | $3,995,000

1644 Duke Of Windsor Rd, Virginia Beach, VA 23454
1644 Duke Of Windsor Road, Virginia Beach, VA 23454
Tim Cochran
LISTING AGENT:
Tim Cochran

Along the water’s edge in Virginia Beach’s prestigious Alanton, this custom residence unfolds across a 1.2-acre waterfront sanctuary designed for deep-water living. An open floor plan centers on a chef’s kitchen with quartz surfaces, while a breakfast nook sits wrapped in shimmering water views. For evenings in, a sunken living room with a gas fireplace sets a relaxed tone, complemented by a refined dining room and an impressive media room with bar for effortless entertaining. The primary suite reads like a private resort, complete with a sitting area, spa-inspired bath, and a generous walk-in closet, joined by two additional en-suites. Outside, a breathtaking pool with cascading waterfalls and covered porches extend daily life into the landscape. A detached three-car garage includes a full apartment above, while a dock and lift complete the deep-water setting.

Price:
$3,995,000
Size:
6,828 sq ft
Contact:
Tim Cochran, BHHS RW Towne Realty, 757.286.6600
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2515 Fleets Bay Rd | $3,800,000

2515 Fleets Bay Rd Whitestone VA 22578
2515 Fleets Bay Rd, Whitestone, VA 22578
johnmartin
LISTING AGENT:
John Martin

Along the James River, this rare estate unfolds across 3+ private acres in the heart of Richmond. The classic 1959 brick and slate residence spans 5,349 square feet and includes a walk-out basement, offering a layout that flexes easily with everyday life. Recent updates bring a fresh feel to the interiors, with a new kitchen, refinished hardwood floors, and an updated half bath. Two bedrooms on the main level create a comfortable option for main-floor living, while four additional bedrooms are set upstairs. A sunroom frames sweeping river views, drawing the landscape into the daily rhythm of the house. Outside, true river access and a circle drive underscore the home’s irreplaceable setting and easy sense of arrival, where the water is always part of the view.

Size: 3.00 acres

Price:
$3,800,000
Contact:
John Martin, Shaheen Ruth Martin & Fonville, 757.870.2893
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Good Luck Cellars | $2,978,000

1025 Goodluck Rd Kilmarnock VA 22482
1025 Goodluck Rd, Kilmarnock, VA 22482
karinandrews
LISTING AGENT:
Karin Andrews

Surrounded by 135.89 scenic acres in the heart of Virginia’s Northern Neck, Good Luck Cellars is presented as one of the Commonwealth’s premier wineries and event venues. Twenty-five acres of producing vineyards set the tone for daily life here, where the rhythms of a working vineyard meet the ease of a proven, award-winning destination. Offered as a turn-key property, the estate includes the winery itself along with a dedicated tasting room, production facilities, and a collection of event spaces supported by essential outbuildings. Set within the Chesapeake Bay Wine Region, it’s a place designed for both craft and gathering—welcoming guests while keeping operations purposeful and efficient. From the first pour to the final toast, the setting invites a future built around wine, land, and memorable occasions.

Price:
$2,978,000
Size:
11,800 sq ft
Contact:
Karin Andrews, Shaheen, Ruth, Martin & Fonville Real Estate, 804.445.5500
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Where Elegance Meets Premier Event Living | $2,950,000

9945 Brooks Mill Road Wirtz VA 24184
9945 Brooks Mill Road, Wirtz, VA 24184
Angie Mcghee
LISTING AGENT:
Angie Mcghee

Set on 11.22 breathtaking acres in the heart of Franklin County, The Virginian—“The Stables at Westlake”—is a rare, refined luxury event estate designed as a premier Western-style venue. Rolling countryside and manicured grounds frame expansive open spaces and high-end finishes, creating an atmosphere that feels both grand and inviting. Purposefully planned for modern event functionality, the property offers multiple ceremony and reception settings with seamless indoor-outdoor flow, suited to weddings, upscale gatherings, private events, or even a destination restaurant concept. From golden-hour backdrops to starlit celebrations, every element is meant to impress and perform while maintaining a sense of privacy. With easy accessibility to Smith Mountain Lake and surrounding amenities, it reads less like a single venue and more like a true destination in Southwest Virginia’s luxury event market.

Price:
$2,950,000
Size:
8,384 sq ft
Contact:
Angie Mcghee, MKB Realtors, 540.537.5918