Waterstone
Tuscan and Mediterranean luxury with 24-hour security and Windermere Prep access.
Live the MaxLife.
$2.5M
Median Price
$1.5M – $4.6M
120
Homes
$350–$600
Monthly HOA
2010
Established
Windermere Elementary or Sunset Park Elementary (zoning dependent)
School Zone
Background
A brief history
Waterstone was developed starting in 2010 as an upscale gated community in Windermere's southwest area, just off Winter Garden Vineland Road. Approximately 120 Mediterranean and Tuscan-style homes were planned across multiple sections. Construction progressed from 2010 to 2020, with builders including Brerhill Homes, David Weekley Homes, Sillman Homes, and Toll Brothers. The architectural vocabulary is consistent — barrel tile roofs, Mediterranean elevations, courtyard entries — and the security infrastructure is robust: 24-hour guard gate with brick paver accents, cobblestone bridge entry, and landscape-heavy perimeter. A distinctive amenity is the private walking gate directly into Windermere Preparatory School.
The feel
What it's like to live here
Waterstone is positioned as a luxury gated community where security and architectural consistency are paramount. The brick paver-lined bridge entry and 24-hour guard gate create a formal threshold into the community. Homes range 2,700–9,600 square feet, with 4–7 bedrooms and most featuring barrel tile roofs, brick paver driveways, and Mediterranean-inspired courtyards. Lots vary from 0.35–0.75+ acres. Landscaping is lush and professionally maintained — native plantings, natural wetland preserve, fragrant gardens, and mature oaks create a sophisticated environment. The private walking gate into Windermere Prep is a major amenity for families, and the community attracts professionals valuing security and architectural control.
The details
What to expect
Architecture & Lots
Mediterranean and Tuscan styles exclusively. Barrel tile roofs, stucco, stone and brick elevations, arched entries, courtyard designs. Homes 2,700–9,600 square feet, 4–7 bedrooms. Lots 0.35–0.75+ acres. Brick paver driveways standard. Architectural review enforces Mediterranean vocabulary; modern flat-roof designs not permitted.
Security & Gating
24-hour guard gate with brick paver accents and impressive landscape entry. Cobblestone bridge crossing into the community. Professional security patrols. Resident decals required for entry. Secure, controlled access throughout.
Amenities & Landscaping
Lush and fragrant gardens throughout the community. Natural wetland preserve with walking trails. Multiple lakes and ponds with landscape views. Private walking gate directly into Windermere Preparatory School (major amenity for families). Resident-maintained parks and gathering areas.
HOA Rules & Fees
Monthly HOA $350–$600 depending on section and amenity tier. Architectural review required for all exterior changes — Mediterranean palette strictly enforced. Short-term rentals prohibited; 30-day minimum lease. Landscape maintenance standards enforced. No commercial vehicles or RVs on driveways.
Schools & Access
Private walking gate into Windermere Preparatory School — major amenity for families. Gated entrance off Winter Garden Vineland Road. Eight minutes to Restaurant Row, 25–30 minutes to downtown Orlando, 15 minutes to Disney, 30–35 minutes to MCO. Good access to 429 and Conroy-Windermere Road.
Community
Amenities
- 24-hour guard gate with impressive landscape entry and cobblestone bridge
- Private walking gate to Windermere Preparatory School
- Lush fragrant gardens and landscape design
- Natural wetland preserve with walking trails
- Multiple lakes and ponds with scenic views
- Community parks and gathering spaces
- Professional security patrols
Know Before You Buy
HOA rules worth knowing
- Monthly HOA $350–$600 depending on section
- Mediterranean architectural palette strictly enforced
- All exterior changes require architectural review
- Short-term rentals prohibited; 30-day minimum lease
- Landscape maintenance standards enforced
- Commercial vehicles and RVs prohibited on driveways
- Barrel tile roofs required; flat modern roofs prohibited
Education
School assignments
- Windermere Elementary or Sunset Park Elementary (zoning dependent)
- Bridgewater Middle or Gotha Middle (zoning dependent)
- Windermere High or Olympia High (zoning dependent)
- Windermere Prep (private, direct walking access from community)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Market trades from $1.46M–$2M for entry-level smaller homes, $2M–$3.2M for mid-sized homes with good finishes, and $3.2M–$4.6M for the largest homes or those with premium lake views. Renovation-needed original construction homes enter at $1.46M; fully updated or newer builds command premiums. Days-on-market average 30–50 days for homes priced to comps. The Windermere Prep walking access is a significant value proposition for families; many buyers cite this as a key reason for choosing Waterstone over competing communities.
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Information on this page is compiled from public records, MLS data, community associations, and broker observation. Price ranges, HOA fees, school assignments, and community amenities change — verify all details with MaxLife Realty and the relevant community association before making a purchase decision. Ryan Solberg, Broker, License #BK3354351. MaxLife Realty, 321.373.3536.