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5 Luxe Virginia Estates from Historic Charm to Waterfront Penthouses

By Awais Manzoor

1 min read

luxury that feels like escape without sacrificing ease. From 20.3 secluded acres in Chester to a circa-1817 fieldstone home at the edge of Middleburg, privacy comes with thoughtful updates and flexible spaces. On the Chesapeake Bay, two penthouse retreats quintet sweeping water views with the confidence of gated living. At Smith Mountain Lake, a private point lot with 505 feet of shoreline and a covered 3-slip dock underscores a lifestyle shaped by the water.

13446 Bradley Bridge Road | $1,950,000

13446 Bradley Bridge Road Chester VA 23831
13446 Bradley Bridge Road, Chester, VA 23831
Tina Mccabe
LISTING AGENT:
Tina Mccabe

Set on 20.3 secluded acres and set back from the road, 13446 Bradley Bridge Road balances true privacy with everyday access—approximately 10 minutes from Route 288, I-95, and Chippenham Parkway. Inside, the layout is thoughtfully flexible, offering 5 bedrooms and 4.5 bathrooms, including a first-floor primary suite and a first-floor in-law suite, plus a flex space suited to an office, gym, or activity room. Recent improvements span the property, with new roofing on all three structures, new HVAC systems serving the main home, attached garage, and detached garage, and a new vapor barrier. Modern living is supported by solar panels, an EV charging plug, irrigation around the entire main house, exterior lighting, and security 4K cameras with networking. Indoors, refreshed paint, trim, carpet, upgraded hardware, and smart switches complement a remodeled family room and an updated primary suite with a renovated bath featuring heated floors, heated towel racks, and a digital shower.

Price:
$1,950,000
Size:
4,444 sq ft
Contact:
Tina Mccabe, eXp Realty, 804.536.6800
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Village Gem With Modern Luxuries | $1,950,000

406 E Washington St Middleburg VA 20117
406 E Washington St, Middleburg, VA 20117
cricketbedford
LISTING AGENT:
Cricket Bedford

Originally built circa 1817, this fieldstone residence at the eastern edge of Middleburg’s village pairs early-American character with thoughtful modern updates. Inside, original hardwood floors, stone fireplaces, and built-ins set a warm, tactile tone, complemented by distinctive lighting, updated paint colors, and custom cabinetry crafted by a local artisan. The kitchen is outfitted with high-end appliances, while a light-filled enclosed rear porch adds everyday flexibility and looks out to the gardens. Just steps from the main house, the original Smokehouse has been reimagined as a bonus space that can serve as a cozy 1-bedroom, 1-bath guest retreat, artist studio, home office, fitness space, or pool house. Outdoors, fully fenced, professionally landscaped grounds create a private oasis with a pool—an uncommon find within town limits—and a dividable parcel with entrances from two streets.

Size: 0

Price:
$1,950,000
Contact:
Cricket Bedford, Thomas & Talbot Estate Properties, 540.229.3201
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Waterfront Luxury Without Compromise | $1,849,000

2333 Point Chesapeake Quay 5024 Virginia Beach VA 23451
2333 Point Chesapeake Quay #5024, Virginia Beach, VA 23451
Tim Cochran
LISTING AGENT:
Tim Cochran

Along the water’s edge in Virginia Beach, this beautifully appointed beachfront penthouse pairs relaxed luxury with sweeping Chesapeake Bay views. Set within a premiere gated community, it’s offered turnkey furnished as an option and is truly move-in ready. Inside, soaring 12-foot vaulted ceilings, expansive windows, and high-end finishes bring an easy brightness to the spacious, open layout—equally suited to quiet mornings and evenings with friends. A private balcony extends the living space outdoors, complete with a retractable awning, while a cozy fireplace anchors the room. The gourmet kitchen is outfitted with state-of-the-art appliances, quartz countertops, a large island with bar sink, and a wine cooler. In the owner’s suite, water views frame a custom walk-in closet and a spa-inspired bath with jetted tub and heated floors. Amenities include an elevator, clubhouse, fitness center, beach gazebo, pool, 2-car garage, and storage room.

Price:
$1,849,000
Size:
2,340 sq ft
Contact:
Tim Cochran, BHHS RW Towne Realty, 757.286.6600
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Exclusive Bayfront Penthouse Retreat | $1,749,000

2309 Point Chesapeake Quay 5021 Virginia Beach VA 23451
2309 Point Chesapeake Quay #5021, Virginia Beach, VA 23451
Tim Cochran
LISTING AGENT:
Tim Cochran

Along the water’s edge on the Chesapeake Bay, this penthouse retreat pairs sweeping views with an elevated coastal rhythm inside a beautiful gated community. Natural light pours in from the moment you enter, turning the ever-changing bayfront into the home’s daily backdrop. Step out to the balcony for open-air evenings, unwind by the fireplace, or settle into the gourmet kitchen—each space finished with a consistent sense of premium detail throughout. The expansive owners’ suite is designed as a true sanctuary, featuring a custom walk-in closet and a spa-inspired bath made for slow, restorative mornings. Practical comforts are equally considered, with an oversized 2-car garage, key fob entry, and additional storage. A thoughtfully designed clubhouse, pool, and gazebo on the Bay extend the lifestyle beyond your front door, all within Virginia Beach.

Price:
$1,749,000
Size:
2,340 sq ft
Contact:
Tim Cochran, BHHS RW Towne Realty, 757.286.6600
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Smith Mountain Lake, VA | $1,749,000

2245 Thomason Ln, Goodview, VA 24095
2245 Thomason Ln, Goodview, VA 24095
ednawood
LISTING AGENT:
Edna Jamieson Wood

Along the water’s edge at Smith Mountain Lake, this private point lot delivers 505 feet of shoreline and sweeping, panoramic views that define daily life here. The setting feels intentionally set apart, with a rare sense of privacy that comes from being surrounded by water on multiple sides. At the covered 3-slip dock, 30-foot deep water makes time on the lake effortless, whether you’re setting out early or returning as the light changes across the surface. Inside, an extensive 2022 remodel—backed by approximately $500,000 in luxury improvements—brings a refined, updated finish to the estate while preserving its focus on the outdoors. The result is a waterfront retreat designed for quiet mornings, unhurried afternoons on the dock, and long evenings framed by the lake’s wide horizon.

Price:
$1,749,000
Size:
4,000 sq ft
Contact:
Edna Jamieson Wood, Wainwright & Co., Realtors, 540.520.0168