Situated in the premier waterfront neighborhood of Painter Pointe, this stunning property offers an unparalleled lifestyle on the Chesapeake Bay. Breathtaking views of Fleets Bay from nearly every room, this home is a serene retreat designed for both relaxation and entertaining. Private, sandy beach just steps from the expansive waterside deck. The grounds create a sense of privacy and tranquility, w/ ample room for additional features such as a pool, thanks to the remote septic drainfield. Step inside to discover a light-filled great room with soaring vaulted ceilings, dining area, and a cozy gas fireplace. The adjoining dining area makes this space perfect for hosting family and friends. The well-equipped kitchen features an island, providing extra counter space for cooking or casual dining. The first-floor primary suite offers luxury and convenience, complete with two spacious walk-in closets and a private ensuite bath. This level also includes a dedicated office, a den, and a charming screened porch that opens to the wraparound deck—ideal for soaking in panoramic waterfront views. Upstairs, two generously sized bedrooms share a full bath, providing comfort and privacy for guests. Above the two-bay side-load garage, you'll find a bedroom w/ ensuite bath. A separate workshop off the garage adds to the functionality of this remarkable home. Just minutes from fine dining, boutique shopping, and Indian Creek Yacht and Country Club, 286 Waterbury Road is a rare opportunity to own a private oasis in one of the Chesapeake Bay's most desirable neighborhoods.
For sale
Price cut: $320K (6/17)
$1,950,000
286 Waterbury Rd, Kilmarnock, VA 22482
4beds
5,108sqft
Est.:
Single Family Residence
Built in 1998
2.06 Acres Lot
$-- Zestimate®
$382/sqft
$208/mo HOA
What's special
Waterfront neighborhoodFirst-floor primary suiteCozy gas fireplaceTwo spacious walk-in closetsLight-filled great roomPanoramic waterfront viewsGenerously sized bedrooms
- 118 days
- on Zillow |
- 1,081 |
- 35 |
Zillow last checked: 7 hours ago
Listing updated: August 11, 2025 at 06:49am
Listed by:
Robert B. Bragg IV 804-436-7337,
Bragg & Company
Source: CVRMLS,MLS#: 2512086
Originating MLS: Chesapeake Bay Area MLS

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Level: First
- Dimensions: 24.10 x 19.5
Bedroom 2
- Level: Second
- Dimensions: 14.1 x 18.4
Bedroom 3
- Level: Second
- Dimensions: 20.2 x 20.6
Bedroom 4
- Description: Bonus Room
- Level: Second
- Dimensions: 19.4 x 26.1
Foyer
- Level: First
- Dimensions: 7.3 x 2.9
Other
- Description: Tub & Shower
- Level: First
Other
- Description: Tub & Shower
- Level: Second
Great room
- Description: Living Room + Dining Room
- Level: First
- Dimensions: 23.0 x 35.0
Half bath
- Level: First
Kitchen
- Level: First
- Dimensions: 17.0 x 18.0
Laundry
- Level: First
- Dimensions: 11.8 x 11.5
Office
- Level: First
- Dimensions: 13.7 x 14.10
Heating
- Electric, Heat Pump
Cooling
- Heat Pump
Appliances
- Included: Dryer, Dishwasher, Electric Water Heater, Gas Cooking, Disposal, Microwave, Oven, Refrigerator, Washer
Features
- Wet Bar, Bookcases, Built-in Features, Balcony, Bedroom on Main Level, Ceiling Fan(s), Dining Area, Fireplace, High Ceilings, Kitchen Island, Bath in Primary Bedroom, Main Level Primary, Pantry, Walk-In Closet(s)
- Flooring: Carpet, Tile, Wood
- Doors: Sliding Doors
- Basement: Crawl Space
- Attic: Pull Down Stairs,Walk-In
- Number of fireplaces: 1
- Fireplace features: Electric
Interior area
- Total interior livable area: 5,108 sqft
- Finished area above ground: 5,108
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Attached, Circular Driveway, Driveway, Garage, Oversized, Unpaved, Workshop in Garage
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Screened, Wrap Around, Deck, Porch
- Exterior features: Deck, Porch, Unpaved Driveway
- Pool features: None
- Fencing: None
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Beach Access, Bayfront, Water Access, Walk to Water, Waterfront
- Body of water: Fleets Bay
- Frontage length: 340.0000,340.0000
Lot
- Size: 2.06 Acres
- Features: Beach Front, Buildable, Waterfront
Details
- Parcel number: 54A10100
- Zoning description: R1
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Drywall, Frame, Vinyl Siding
- Roof: Composition
Condition
- Resale
- New construction: No
- Year built: 1998
Utilities & green energy
- Sewer: Septic Tank
- Water: Community/Coop, Shared Well
Community & HOA
Community
- Features: Bulkhead
- Subdivision: Painter Pointe
HOA
- Has HOA: Yes
- Services included: Road Maintenance, Water
- HOA fee: $2,500 annually
Location
- Region: Kilmarnock
Financial & listing details
- Price per square foot: $382/sqft
- Tax assessed value: $1,216,500
- Annual tax amount: $8,028
- Date on market: 4/30/2025
- Ownership: Individuals
- Ownership type: Sole Proprietor
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