Introducing Deep Hole Hideaway, a versatile and fully turnkey multi-property listing offering exceptional rental potential and room for expansion. This unique property features a beautifully renovated duplex and a new construction home, set on a spacious lot with ample capacity for additional development. The duplex has been completely renovated within the last 5 years, with one unit offering two bedrooms and one bathroom, and the other featuring one bedroom, a bonus room, and one bathroom—perfect for accommodating guests or tenants. The property is designed to comfortably host up to 23 guests, making it an ideal rental opportunity. Adjacent to the duplex is a new construction home boasting two bedrooms, two bonus rooms, and 2.5 bathrooms, providing modern comforts and flexible space for family, guests, or additional rental income. The property’s generous lot includes enough room and septic capacity to build an extra 2-bedroom dwelling, offering future expansion potential. Enjoy peek-a-boo views of the marshes and Oyster Bay, adding scenic serenity to this charming retreat. Sold fully furnished and equipped, Deep Hole Hideaway provides a ready-to-go investment or primary residence in a desirable location. Don’t miss the opportunity to own this exceptional property with endless possibilities.
For sale
$1,200,000
5421 & 5423 Deep Hole Rd, Chincoteague Island, VA 23336
5beds
5baths
3,450sqft
Est.:
Multi Family
Built in 1988
-- sqft lot
$-- Zestimate®
$348/sqft
$-- HOA
What's special
- 1 day
- on Zillow |
- 26 |
- 1 |
Zillow last checked: 7 hours ago
Listing updated: August 01, 2025 at 02:10pm
Listed by:
Meghan Clarkson 757-894-0798,
Long & Foster Real Estate, Inc.
Source: Bright MLS,MLS#: VAAC2002116

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
Basement
- Area: 0
Heating
- Heat Pump, Electric
Cooling
- Heat Pump, Electric
Appliances
- Included: Dishwasher, Washer, Dryer, Refrigerator, Stainless Steel Appliance(s), Electric Water Heater
Features
- Ceiling Fan(s), Dining Area, Entry Level Bedroom, Open Floorplan, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-In Closet(s), Bathroom - Tub Shower, Dry Wall
- Flooring: Luxury Vinyl
- Windows: Skylight(s), Window Treatments
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 3,450
- Total interior livable area: 3,450 sqft
Property
Parking
- Parking features: Gravel, Driveway
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Patio & porch: Deck
- Pool features: None
- Waterfront features: Pond
Lot
- Size: 0.5 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 031B2A000003700
- Zoning: RESIDENTIAL
- Special conditions: Standard
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Coastal
- Property subtype: Multi Family
Materials
- Vinyl Siding
- Foundation: Crawl Space
- Roof: Metal,Composition
Condition
- New construction: No
- Year built: 1988
Utilities & green energy
- Sewer: Private Septic Tank
- Water: Public
Community & HOA
Community
- Subdivision: Chincoteague
Location
- Region: Chincoteague Island
Financial & listing details
- Price per square foot: $348/sqft
- Tax assessed value: $305,200
- Annual tax amount: $1,419
- Date on market: 8/1/2025
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
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