Windward Pointe, Holly Springs NC: Neighborhood Guide and Homes for Sale

Caul Group Residential, brokered by eXp Realty

Windward Pointe is a Holly Springs neighborhood about a mile by road from Town Hall, in ZIP 27540. Wake County records show about 157 detached homes built from 1993 to 1998, with a median of about 1,934 heated square feet. The 5 recorded sales from October 2025 through September 2026 had a median of $500,000.

Here is where Windward Pointe is, what the homes are like, recent sale prices, the HOA and the assigned schools. This guide covers the neighborhood as a whole.

Where Windward Pointe is

All 157 homes are inside the Town of Holly Springs in the 27540 ZIP code. Streets include Cayman Avenue, St. Vincent Drive, Bahama Court, Guadeloupe Court, Sandy Point Way and Nevis Drive (Wake County property records).

Road distances from the center of the neighborhood (OpenStreetMap routing, November 2026):

  • Holly Springs Town Hall: 1.0 mile
  • WakeMed Cary Hospital: 8.1 miles
  • Cary Town Hall: 11.5 miles
  • NC State Capitol, downtown Raleigh: 17.0 miles
  • Research Triangle Park: 20.2 miles
  • RDU Airport: 22.9 miles

Homes in Windward Pointe

Across the 157 homes (Wake County property records, November 2026):

  • Built 1994 at the 10th percentile, 1995 median, 1996 at the 90th percentile, all from 1993 to 1998
  • 1,594 to 2,328 square feet at the 10th and 90th percentiles, 1,934 median
  • Lots of 0.23 to 0.35 acres at the 10th and 90th percentiles, 0.27 median

Recent sale prices

Wake County records show 5 recorded sales from October 2025 through September 2026, with a median of $500,000, ranging from $493,000 to $528,000 (Wake County property records).

HOA

County records show common areas owned by the Windward Pointe Homeowners Association (Wake County property records). Ask for the dues, any special assessments and the resale fees for a specific home on the NC Residential Property and Owners' Association Disclosure Statement.

The Windward Pointe market right now

For the 27540 ZIP code, Redfin reports for the three months ending September 2026:

  • Median sale price: $589,827, down 1.7% year over year
  • Median days on market: 24, compared with 23 a year earlier
  • Homes sold in September: 206, compared with 202 a year earlier
  • Sale-to-list price: 99.0%
  • Homes sold above list price: 19.8%
  • Homes with a price drop: 39.4%

What it means: the 27540 median was about flat from a year ago, and homes sold in a median of 24 days. Windward Pointe homes are smaller and older than many in the ZIP, so recent sales in the neighborhood are the better guide.

Assigned schools

The Wake County Public School System assigns by address. For 2026-27, all 50 sampled Windward Pointe addresses were zoned for Holly Springs Elementary, on a year-round calendar, Holly Ridge Middle and Felton Grove High (WCPSS). None was listed as capped; see what a capped school means. Check a specific address with the WCPSS address lookup tool.

Things to do nearby

  • Downtown Holly Springs, about a mile away.
  • WakeMed Cary Hospital, about 8.1 miles away.
  • Cary, about 11.5 miles to Town Hall.
  • Research Triangle Park, about 20 miles away.

Buying in Windward Pointe: what to check

  • Roof, HVAC, windows and water heater age on a 1990s home.
  • HOA dues and rules.
  • Lot size and backyard space.
  • The year-round elementary calendar.
  • School assignment by exact address.

See our buyer services page for how we help buyers.

Selling in Windward Pointe: what buyers ask about

  • Recent comparable sales in the neighborhood.
  • Updates to the kitchen, baths and major systems.
  • Roof and HVAC age.
  • HOA dues.
  • Drive times to downtown Holly Springs, Cary and RTP.

See how we sell homes, or start with a home value estimate.

Windward Pointe FAQs

Where is Windward Pointe in Holly Springs?

Windward Pointe is in the Town of Holly Springs, in ZIP 27540, about 1.0 mile by road from Holly Springs Town Hall.

How many homes are in Windward Pointe?

Wake County records show about 157 detached homes.

What do homes in Windward Pointe cost?

From October 2025 through September 2026, the 5 recorded sales had a median of $500,000, ranging from $493,000 to $528,000, per Wake County records.

When were Windward Pointe homes built?

All were built from 1993 to 1998, with a median build year of 1995.

How big are Windward Pointe homes?

The median is about 1,934 heated square feet, with most from 1,594 to 2,328 square feet, per Wake County records.

Is there an HOA in Windward Pointe?

Yes. County records show common areas owned by the Windward Pointe Homeowners Association. Ask for dues on the disclosure statement.

Which schools serve Windward Pointe?

For 2026-27, all sampled addresses were zoned for Holly Springs Elementary, Holly Ridge Middle and Felton Grove High. Confirm any address with the WCPSS address lookup.

Thinking of selling in Windward Pointe?

Windward Pointe homes were built in the 1990s, and condition and updates drive price more than age. We price from recent Windward Pointe and nearby sales of similar homes.

Caul Group Residential is the #1 Resale Team in the Triangle. Our office is at 201 Shannon Oaks Circle, Suite 200, Cary, NC 27511. RealTrends Verified 2026 (based on 2025 sales) ranks our team, "Caul Team," #1 in Raleigh by sides and by volume. See the RealTrends profile. We have 5.0 stars on Zillow from 1,200+ reviews (Oct 2026). Read the reviews.

More on the area: Holly Springs, Sunset Ridge, 12 Oaks, Holly Glen, Cary and our Cary agents.