TL;DR: Is Windward Oaks a good neighborhood in Wilmington, NC?

  • Where: Windward Oaks is an established neighborhood of about 150 homes in south Wilmington (28409), between Masonboro Loop Road and Masonboro Sound Road.
  • Price range: Four homes sold in Windward Oaks in 2026, from about $800,000 to $1.3 million.
  • Lots: Roughly half an acre, larger than most Wilmington neighborhoods, with mature trees and landscaping.
  • Schools: Masonboro Elementary is directly across the street.
  • Water access: About 2 miles to Masonboro Yacht Club, plus a public boat ramp off Trails End Road.
  • Who knows it best: Jennifer Bullock of the Jennifer Bullock Team at RE/MAX Executive lived in Windward Oaks for 7 years and has sold 12 homes there, more than any other Realtor in the past 15 years.
  • Homes for sale: See current Windward Oaks homes for sale.

Windward Oaks is one of my top 10 favorite neighborhoods in Wilmington, North Carolina — and I don't say that lightly. I lived here for seven years, and I've sold more homes in Windward Oaks than any other Realtor over the past 15 years. If Windward Oaks had a mayor, it would be me.

My 12th Windward Oaks closing: 6927 Finian Drive

I just closed my 12th home in this neighborhood: 6927 Finian Drive. We had it under contract in only 7 days with an almost full-price offer. Even better, the sellers had zero seller concessions and zero repairs.

That made it a smooth, easy sale for them. They listed, went under contract and moved on to the next chapter — exactly how selling a home should feel.

A little Windward Oaks history

Windward Oaks was developed in the mid-1990s. It's an established community of about 150 homes, tucked between Masonboro Loop Road and Masonboro Sound Road.

This year, four homes have sold in Windward Oaks, ranging from about $800,000 to $1.3 million. To me, it's the heart of Wilmington. You can browse current Windward Oaks homes for sale on my website.

Why people love living in Windward Oaks

It always comes back to location, location, location.

  • Top-rated school across the street. Masonboro Elementary is right across the road. Both of my children went there.
  • Close to the water. You're about 2 miles from Masonboro Yacht Club, and there's a public boat ramp right off Trails End Road.
  • Bigger lots. Most lots are roughly half an acre — larger than many Wilmington neighborhoods — with gorgeous, mature landscaping.
  • Privacy and serenity. Those mature trees and generous lots give the neighborhood a quiet, tucked-away feel while keeping you close to everything.

People don't leave Windward Oaks

In 20 years in real estate, I've watched this neighborhood change over time. One thing has stayed the same: once people buy here, they stay for years and years. The sellers of the home I just closed had lived there 32 years.

That's why homes here are special — and why buyers need someone who knows the neighborhood when one comes up.

Thinking about buying or selling in Windward Oaks?

I've lived here, I've sold here, and I know exactly what buyers are looking for in this part of Wilmington. Whether you're thinking about selling, getting your home ready for market, or just curious what your Windward Oaks home is worth, give your neighborhood "mayor" a call.

I'm born and raised in Wilmington and have been in real estate for 20 years. I'd love to help you.

Want more on Wilmington — the best neighborhoods, the good, the bad and the ugly? Subscribe to my YouTube channel for updates.