Why this home stands out
What sets 5429 Club Head Road apart is the combination of generous square footage for a late-1980s build and an almost unbeatable position relative to JEB Little Creek-Fort Story — five minutes door to gate. At 2,411 square feet across four bedrooms and two and a half baths, there's real room to spread out, and the surrounding streets have a settled, established feel that newer subdivisions simply haven't had time to develop.
CYPRESS POINT and the Virginia Beach real estate market
Club Head Road sits in a well-established residential pocket of Virginia Beach, the kind of neighborhood where mature trees line the streets and neighbors tend to stick around. The area developed primarily in the 1980s, so the homes here have character and lot sizes that reflect an era when builders weren't squeezing every square foot out of the land. Virginia Beach is one of the largest cities by land area in the country, and this corner of it — north of the Oceanfront, east of Norfolk — strikes a balance between suburban calm and genuine urban convenience. You're close to the Chesapeake Bay shoreline without paying waterfront premiums, and the broader Virginia Beach street grid puts you within a short drive of everything from big-box retail to independent restaurants. The city's military presence means the community has a transient-yet-tight-knit quality: people come from everywhere, settle in quickly, and form real connections. This part of Virginia Beach consistently draws buyers who want space, accessibility, and a neighborhood that already feels complete.
What's nearby
Day-to-day errands are easy from Club Head Road. Food Lion is 0.7 miles away for full grocery runs, and a Dollar General is just under a mile for quick pick-ups. When you want to eat out, Cypress Point Country Club is only 0.4 miles away, and both Happy Cafe and Susan's Kitchenette Filipino are a half-mile down the road. Coffee is covered by Happy Cafe and It Can Be Coffee Co, both within 0.6 miles. For fitness, Torch Yoga and Treviox Yoga Blocks are 0.6 miles out, with FitnessVibes757 not far behind. Lawson Hall Park is a three-minute walk at 0.3 miles, and Raleigh Square Park and Cypress Point North Park round out the green space options nearby.
For different buyers
For military families relocating
JEB Little Creek-Fort Story is approximately five minutes from 5429 Club Head Road — one of the shortest commutes you'll find in Virginia Beach without living on base. That proximity matters for early formations, duty-day flexibility, and keeping family life manageable during deployments. A VA loan can make this four-bedroom home even more accessible, and the established neighborhood means you're moving into a community, not just a house.
For families upgrading
Four bedrooms and 2,411 square feet give a growing family genuine breathing room — dedicated spaces for work-from-home, a guest room, or a kids' playroom without anyone feeling crowded. Three parks are within half a mile, including Lawson Hall Park just a short walk away. The lot sizes in this neighborhood are generous by Virginia Beach standards, and the home's 1988 construction means the bones are solid and the layout is practical rather than trendy.
More buyer questions
How far is 5429 Club Head Road from JEB Little Creek-Fort Story?
The drive is approximately five minutes under normal traffic conditions, making this one of the closest off-base residential streets to the main gate. That short commute is a meaningful quality-of-life factor for active-duty personnel.
What is the square footage and layout of 5429 Club Head Road?
The home offers 2,411 square feet of living space across four bedrooms and two and a half bathrooms, built in 1988 as a single-family residential property.
Where are the nearest grocery stores to 5429 Club Head Road?
Food Lion is 0.7 miles away and is the closest full-service grocery option; a Dollar General is 0.9 miles out for convenience items.
Is 5429 Club Head Road in a flood zone?
Flood zone information for this address is displayed in the dedicated FloodRisk tile on this page, which pulls current FEMA map data for the most accurate and up-to-date designation.
Are there parks within walking distance of 5429 Club Head Road?
Yes — Lawson Hall Park is just 0.3 miles away, Raleigh Square Park is 0.4 miles, and Cypress Point North Park is 0.5 miles, giving you three green-space options all within a comfortable walk.
Want to see 5429 Club Head Road in person or get answers about the neighborhood? Tom and Dariya Milan at LPT Realty are ready to help — reach out today.
