Holly Springs · Southwest Wake County, NC

Windward Pointe homes for sale & neighborhood guide

For buyers who want a 1990s home on a quarter-acre lot with two Town parks within half a mile.

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Written by Leonna Weiss, REALTOR®
Last reviewed:

  • 157HomesWake County1, 11
  • 1993–98BuiltWake County1, 11
  • 0.27 acMedian lotWake County1, 11
  • 0.2 miTo Jones ParkTown GIS7

The neighborhood

Cayman Ave and the island courts

Windward Pointe is an established Holly Springs neighborhood of 157 single-family homes built from 1993 to 1998, inside town limits. The streets carry island names, from Cayman Ave to St Kitts Ct, and Jones Park is about 0.2 miles away in a straight line.1, 7, 11

Windward Pointe was platted in five phases from 1993 to 1996, and 139 of its 157 homes were finished in 1994, 1995 or 1996. Wake County lists 160 lots with access from Cayman Ave; the Town maps about 57 acres.1, 2, 7, 11

Cayman Ave is the spine, with 50 homes. Off it, short courts named Bahama, Barbados, Guadeloupe, Trinidad, St Lucia and St John hold 5 to 18 homes each. The median plan is near 1,930 square feet, on lots of about a quarter acre.1, 11

The association’s footprint is small: two parcels, about half an acre, on Cayman Ave. One more parcel, at 201 Holly Springs Rd, belongs to the Town.4, 1, 11

Homes & sections

Same era, similar plans

Nearly every home dates from 1994 to 1996, so expect similar ages and systems.1, 11

Phase 4–5 courts

Bahama Ct, Guadeloupe Ct, Sandy Point Way and Nevis Dr, built 1995–1998.1, 11

See Windward Pointe homes

Original systems

Homes are near 30 years old. Ask about the roof, windows, HVAC and water heater.1, 11

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The money

Costs to plan for

CostAmountWhere to confirm
HOA duesWindward Pointe Homeowners AssociationAsk whether dues apply and what they cover
Property taxWake County plus Holly Springs ratesParcel tax record
 Amounts appear only when confirmed.

Town and county taxes

Inside town limits, the bill adds the Holly Springs rate to Wake County’s.6

Life beyond the house

Two parks within half a mile

No pool or clubhouse parcel is on record; the association owns about half an acre.4, 1, 11

Town park

Jones Park

Playgrounds, a fishing pond, a ball field and disc golf, about 0.2 miles away (straight-line).8, 7

Town park

Veterans Park

A fishing pier and a half-mile greenway, about 0.3 miles away (straight-line).10, 7

HOA land

About 0.5 acres

Two association parcels on Cayman Ave.4

Schools

Schools for a Windward Pointe address

WCPSS assigns by address.9

Check the exact address for your move year.

Check assignments

Location & daily life

Getting around

Getting your bearings

Where Windward Pointe sits

Jurisdiction
Holly Springs town limits1, 3
Mail
Holly Springs, NC 275401
Example parcel
609 Cayman Ave (PIN 0649952280)5
Open in Google Maps ↗

Key roads

Streets in Windward Pointe

From Wake County records1, 11

  • Cayman Ave50 homes
  • St Vincent Dr20 homes
  • Bahama Ct18 homes
  • Guadeloupe Ct16 homes
  • Sandy Point Way9 homes
  • Nevis Dr8 homes

Your home search

Windward Pointe homes for sale

Listings update from the MLS See all Windward Pointe homes ↗

Open the full Windward Pointe search on its own page, or ask Leonna about upcoming and off-market Windward Pointe homes. Listing data courtesy of Doorify MLS; the IDX disclaimer appears with the results above.

Direct answers

Questions about Windward Pointe

Checked Oct 2026. Ask Leonna.

What is Windward Pointe in Holly Springs, NC like?

Windward Pointe is an established Holly Springs neighborhood of 157 single-family homes built from 1993 to 1998, inside town limits. The streets carry island names, from Cayman Ave to St Kitts Ct, and Jones Park is about 0.2 miles away in a straight line.1, 7, 11

Is Windward Pointe inside Holly Springs town limits?

Yes. Wake County lists Holly Springs as the city and planning jurisdiction.1, 3

Does Windward Pointe have an HOA?

Wake County lists Windward Pointe Homeowners Association as owner of two small parcels, about half an acre. No pool or clubhouse is on record. Confirm dues and covenants with the HOA.4

What parks are near Windward Pointe?

Jones Park is about 0.2 miles away and Veterans Park about 0.3, measured straight-line on Town GIS.7, 8, 10

What schools serve Windward Pointe?

WCPSS assigns by address and can change it yearly. Use its lookup for your move year.9

Build your shortlist

More neighborhoods to compare

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197 homes built 1995–2005, with a 4.62-acre HOA clubhouse parcel.

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Valleyfield

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Leonna Weiss · Weiss Choice Realty

Find your place in Windward Pointe

Like a Windward Pointe home? Send it to me and I’ll check its age, the HOA papers and what’s been updated.

Talk with Leonna Call (919) 648-0458

Sources and further reading

  1. Wake County GIS: Parcels layer (WINDWARD POINTE (PROPDESC match): 161 parcels; 157 single-family homes built 1993–1998 (1994: 48, 1995: 46, 1996: 45); heated area 1,328–3,358 sq ft, median 1,934; median lot 0.27 ac; plats PH1–PH5 recorded 1993–1996; streets: Cayman Ave 50, St Vincent Dr 20, Bahama Ct 18, Guadeloupe Ct 16, Sandy Point Way 9, Nevis Dr 8, Barbados Ct 7, St Croix Dr 7, Trinidad Ct 6, St Kitts Ct 6, St Lucia Ct 5, St John Ct 5; one Town-owned parcel at 201 Holly Springs Rd)
  2. Wake County GIS: Subdivisions layer query, lots, acres and approval dates (Query: UPPER(NAME) LIKE '%WINDWARD%'; re-run Oct 25, 2026. Records: WINDWARD POINTE: 160 lots, 57.7 ac, access CAYMAN AVE, approved 1995-01-01, status EXISTING, jurisdiction HOLLY SPRINGS; WINDWARD DOWNS: 126 lots, 15.5 ac, access WINDSTORM WAY, approved 1998-07-31, status EXISTING, jurisdiction RALEIGH)
  3. Town of Holly Springs: Extraterritorial Jurisdiction Information
  4. Wake County iMAPS: Windward Pointe Homeowners Association Inc parcel at Cayman Ave (2 association parcels total 0.5 ac)
  5. Wake County iMAPS: 609 Cayman Ave, PIN 0649952280 (sample parcel; 0.37 ac; built 1996; geo)
  6. Wake County: Tax Rates & Fees
  7. Town of Holly Springs GIS: Subdivisions layer (Windward Pointe: mapped 57.1 acres; straight-line distances: Jones Park about 0.2 mi, Veterans Park about 0.3 mi)
  8. Town of Holly Springs: Jones Park (405 School Days Ln; 24 acres; playgrounds, fishing pond, ball field, disc golf, greenway access)
  9. WCPSS school assignment lookup
  10. Town of Holly Springs: Veterans Park (600 Bikram Dr; half-mile greenway to Sunset Lake Rd and Jones Park; accessible fishing pier)
  11. Wake County GIS: Parcels layer query, per-street and per-section detail (Query UPPER(PROPDESC) LIKE '%WINDWARD POINTE%' OR '%WINDWARD PT%', Holly Springs/Fuquay ZIP parcels, re-run Oct 25, 2026 (matches page figures). 157 homes by year built: 1993: 6, 1994: 48, 1995: 46, 1996: 45, 1997: 10, 1998: 2; home lots 0.23–0.56 ac, median 0.27; heated area 1,328–3,358 sq ft, median 1,934. Homes by street (count; years built; median heated area; deed acres): Cayman Ave 50 (1993–1997, by year 1993: 1, 1994: 24, 1995: 18, 1996: 6, 1997: 1; median 1,914 sq ft; lots 0.23–0.56 ac, median 0.26); St Vincent Dr 20 (1994–1997, by year 1994: 1, 1995: 3, 1996: 13, 1997: 3; median 1,976 sq ft; lots 0.23–0.34 ac, median 0.28); Bahama Ct 18 (1995–1996, by year 1995: 17, 1996: 1; median 1,912 sq ft; lots 0.23–0.42 ac, median 0.25); Guadeloupe Ct 16 (1995–1998, by year 1995: 1, 1996: 13, 1998: 2; median 1,860 sq ft; lots 0.23–0.41 ac, median 0.32); Sandy Point Way 9 (1996–1997, by year 1996: 6, 1997: 3; median 2,138 sq ft; lots 0.26–0.55 ac, median 0.33); Nevis Dr 8 (1996–1997, by year 1996: 5, 1997: 3; median 1,984 sq ft; lots 0.23–0.35 ac, median 0.26); Barbados Ct 7 (1994; median 2,072 sq ft; lots 0.23–0.46 ac, median 0.29); St Croix Dr 7 (1994–1996, by year 1994: 1, 1995: 5, 1996: 1; median 2,014 sq ft; lots 0.24–0.28 ac, median 0.26); St Kitts Ct 6 (1994; median 1,816 sq ft; lots 0.25–0.31 ac, median 0.28); Trinidad Ct 6 (1994; median 1,918 sq ft; lots 0.29–0.39 ac, median 0.3); St John Ct 5 (1993; median 1,616 sq ft; lots 0.25–0.35 ac, median 0.26); St Lucia Ct 5 (1994–1995, by year 1994: 3, 1995: 2; median 1,874 sq ft; lots 0.25–0.38 ac, median 0.28). Homes by plat section: Windward Pointe (plat 1993): 1 homes, built 1994 (Cayman Ave 1); Windward Pointe Sub (plat 1993–1994): 52 homes, built 1993–1995, median 1,895 sq ft, median lot 0.26 ac (Cayman Ave 33, Barbados Ct 7, St Lucia Ct 5, St John Ct 5, St Vincent Dr 2); Windward Pointe Sub Ph2 (plat 1994): 12 homes, built 1994, median 1,842 sq ft, median lot 0.3 ac (Trinidad Ct 6, St Kitts Ct 6); Windward Pointe Sub Ph3 (plat 1994): 16 homes, built 1994–1996, median 2,018 sq ft, median lot 0.26 ac (Cayman Ave 7, St Croix Dr 7, St Vincent Dr 2); Windward Pointe Ph5 (plat 1995): 33 homes, built 1996–1997, median 2,001 sq ft, median lot 0.28 ac (St Vincent Dr 16, Sandy Point Way 9, Nevis Dr 8); Windward Pointe Sub Ph4 (plat 1995): 42 homes, built 1995–1998, median 1,860 sq ft, median lot 0.27 ac (Bahama Ct 18, Guadeloupe Ct 15, Cayman Ave 9); Rev Lt160 Windward Pointe Sub P4 (plat 1996): 1 homes, built 1998 (Guadeloupe Ct 1). Derived: built 1994–1996: 48 + 46 + 45 = 139 of 157 homes.)

Rules and fees can change; confirm with the HOA. Holly Springs guide.

Written by Leonna Weiss, REALTOR®. Weiss Choice Realty, brokered by Keller Williams Legacy.