About Cypress Chase Neighborhood
Cypress Chase sits inside a single gated entrance off Winter Garden Vineland Road, tucked between Walt Disney World property to the south and the southern edge of Windermere to the north. The mailing address reads Orlando because the neighborhood falls in the 32836 ZIP code rather than the Town of Windermere proper, but the community is consistently marketed as part of the broader Windermere area and shares its school zones, shopping centers, and Butler Chain corridor lifestyle.
The 134 homes were built by Greater Homes between 2002 and 2005 in a mix of traditional, contemporary, and Florida architectural styles. Floor plans range from roughly 1,700 to over 3,000 square feet, typically with 3 to 5 bedrooms and 2 to 3 bathrooms. All homes feature shingle roofs, cement driveways, and tropical landscaping; about half include private screened pools — a higher pool ratio than is typical for production builds of this vintage. Roughly 51 of the homes back to one of the interior ponds, with the remainder backing to conservation buffers or interior streets.
The community's signature feature is its interior park, which residents access without leaving the gate. The park includes a playground, a picnic shelter, a half basketball court, and an open field — modest amenities by master-planned standards, but unusually self-contained for a 134-home enclave. Combined with the gated entry and the absence of a CDD assessment, the package gives Cypress Chase a value profile that's hard to replicate this close to Disney.
📊 Quick Facts
🏡 Home Features
Common construction features across the community:
- Shingle roofs (typical of early-2000s Greater Homes builds — material to verify on resale)
- Cement driveways and standard concrete-block construction
- Tropical landscaping packages with palms and flowering shrubs
- Two-car garages standard; three-car configurations on larger floor plans
- Open kitchen-to-family-room layouts typical of early 2000s production homes
- Screened lanais on most homes; pool cages on the roughly half with private pools
Publisher note: Specific roof age, pool equipment age, and any post-2005 renovations vary by individual home and should be verified per listing.
🌳 Interior Park & Pond Network
The interior park is one of Cypress Chase's defining features — most gated communities of this size simply don't include a built-in amenity package. The park sits centrally within the community and includes:
- A playground sized for elementary-age and younger children
- A covered picnic shelter for HOA events and family gatherings
- A half basketball court
- An open field for casual play
The community is also organized around an interior pond network. About 51 homes — roughly 38% of the community — back directly to one of the ponds, providing water views and a buffer from neighboring rear lots. The ponds are not connected to the Butler Chain and are not navigable, but they offer the visual benefit of waterfront living without the pricing or maintenance profile of true lakefront homes.
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Cypress Chase Location & Connections
Cypress Chase occupies a single-entry pocket on the west side of Winter Garden Vineland Road (CR 535), in the wedge of unincorporated Orange County between the southern edge of Windermere and Walt Disney World property to the south. From the gate, residents reach Winter Garden Village and the SR 429 Expressway by heading north on CR 535, and reach Lake Buena Vista, Disney Springs, and I-4 by heading south. Downtown Windermere's Town Square sits about 7 miles north of the gate.
🏘️ Adjacent Neighborhoods & Areas
- Arlington Bay — directly north along Cinchwood Lane / CR 535, a 93-home Morrison Homes community sharing the 32836 corridor
- Lake Sheen Reserve — east of CR 535, a guard-gated luxury community with Lake Sheen access on the Butler Chain
- Royal Cypress Preserve — to the southeast, a 24-hour guard-gated Toll Brothers community built 2015–2021
- Lake Sheen Sound — newer custom-build enclave by Element Home Builders nearby (no dedicated FNR page; not yet documented in the Windermere hub)
- Walt Disney World property — directly south, with an entry corridor less than a mile from the Cypress Chase gate
🚗 Detailed Commute Times
- Walt Disney World: 5–8 minutes (less than 1 mile to entry corridor)
- Disney Springs: 8–12 minutes (~3 miles)
- Universal Orlando: 18–22 minutes (~10 miles)
- SeaWorld Orlando: 15–18 minutes (~8 miles)
- Downtown Orlando: 22–28 minutes (~14 miles)
- UCF Campus: 35–40 minutes (~22 miles)
- Lake Nona Medical City: 28–32 minutes (~18 miles)
- Cocoa Beach: 60–70 minutes (~55 miles via SR 528)
- Downtown Windermere (Town Square): 12–15 minutes (~7 miles)
✈️ Airport Access
- Orlando International Airport (MCO): 22–28 minutes (~16 miles)
- Orlando Sanford International Airport (SFB): 45–55 minutes (~35 miles)
- Orlando Executive Airport (ORL): 25–30 minutes (~17 miles, general aviation)
- Kissimmee Gateway Airport (ISM): 22–28 minutes (~17 miles, general aviation)
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Cypress Chase Amenities & Lifestyle
Day-to-day life at Cypress Chase blends the convenience of a gated community with the proximity advantages of the 32836 corridor. The interior park and ponds give families a self-contained outdoor space; the location on CR 535 puts Winter Garden Village, Cornerstone at Summerport, and the broader Windermere shopping and dining ecosystem within a short drive. Most residents are commuter households drawn by the combination of Disney proximity, low-fee structure, and access to OCPS schools serving the Windermere High School zone.
For a deeper inventory of what's available across the area, the category guides linked below cover shopping, dining, parks, schools, and entertainment in detail.
🏊 Neighborhood Amenities
Amenities found inside the Cypress Chase gate:
- Gated entry with electronic card access
- Interior community park with playground
- Covered picnic shelter
- Half basketball court
- Open field for informal play and gatherings
- Interior pond network (~51 homes back to water)
- Sidewalks throughout
- HOA-maintained common areas and entrance landscaping
🛍️ Shopping & Services
The closest shopping pulls are Winter Garden Village to the north (an 80-store outdoor center anchored by Whole Foods, Target, and Best Buy) and Cornerstone at Summerport on CR 535 for grocery and everyday services. Disney Springs is roughly 10 minutes south for entertainment-anchored shopping, and The Mall at Millenia is about 15–20 minutes east for luxury and department-store shopping.
For comprehensive shopping information: View our Windermere Shopping Guide →
🍽️ Restaurants
Day-to-day dining is concentrated at Cornerstone at Summerport and along CR 535 for casual options, with the broader Sand Lake Road / Restaurant Row corridor (about 12–15 minutes east) providing the closest fine-dining cluster. Disney Springs adds a deep bench of mid-tier and upscale options within roughly 10 minutes of the gate.
For comprehensive restaurant information: View our Windermere Restaurants Guide →
🎭 Arts & Culture
The closest major arts venue is the Dr. Phillips Center for the Performing Arts in downtown Orlando, roughly 22–28 minutes east. Within Windermere itself, the Town Square hosts the annual Fine Art Show and Light Up Windermere, and the 1890 Schoolhouse offers a small but well-preserved local-history experience.
For comprehensive arts & culture information: View our Windermere Arts & Culture Guide →
🏃 Health & Wellness
The closest multispecialty hub is Orlando Health Medical Pavilion Summerport on CR 535, roughly 8–10 minutes north. Dr. P. Phillips Hospital — the closest full-service hospital — is about 15 minutes east via Apopka-Vineland Road. Urgent care options include MD Now and AdventHealth Centra Care along the CR 535 and Apopka-Vineland corridors.
For comprehensive health & wellness information: View our Windermere Health & Wellness Guide →
🌳 Parks & Recreation
Beyond the interior community park, residents have access to R.D. Keene Park (Windermere's flagship 52-acre park with a Butler Chain boat ramp), Tibet-Butler Preserve (3.6 miles of nature trails on CR 535), and Fernwood Park on Lake Butler. The Butler Chain of Lakes itself offers boating, skiing, and bass fishing for residents who keep boats at one of the public ramps.
For comprehensive parks & recreation information: View our Windermere Parks & Recreation Guide →
⚽ Sports & Athletics
The southern Windermere area is well-served for athletics. Public golf is available at Orange County National Golf Center, and private clubs include Isleworth Golf & Country Club, The Golden Bear Club at Keene's Pointe, and Bay Hill Club & Lodge. Watersports on the Butler Chain — wakeboarding, water skiing, tubing, and bass fishing — anchor the on-water sports scene. Tennis and pickleball options are available through Town of Windermere courts and private clubs.
For comprehensive sports & athletics information: View our Windermere Sports & Athletics Guide →
🎉 Fun Things to Do
Theme park access is the obvious headline — Walt Disney World is less than a mile away, with Universal Orlando and SeaWorld Orlando both under 20 minutes. Town Square in downtown Windermere hosts the Friday Farmers Market, monthly Food Truck Night, the Halloween Costume Parade, PetFest, and Light Up Windermere across the calendar year.
For comprehensive events & activities information: View our Windermere Events & Things To Do Guide →
🎓 Schools
Cypress Chase is currently zoned to (Orange County Public Schools):
- Elementary: Sunset Park Elementary
- Middle: Bridgewater Middle School
- High: Windermere High School
Publisher action item: School zone assignments are subject to change with each OCPS rezoning cycle. Verify current zoning with the Orange County Public Schools attendance-zone lookup before publishing or relying on this information for a specific listing.
For comprehensive school information: View our Windermere Schools Guide →
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How Cypress Chase Compares
Cypress Chase's pitch sharpens when you look at it next to its two closest functional comparables. Royal Cypress Preserve sits on the same side of CR 535 with newer, larger Toll Brothers homes and a more elaborate amenity package — but at a meaningfully higher price point and with newer-construction HOA structures. Arlington Bay is the closest peer in age and size profile but is not gated and offers no internal park.
| Feature | Cypress Chase | Royal Cypress Preserve | Arlington Bay |
|---|---|---|---|
| Year Built | 2002–2005 | 2015–2021 | 2005–2006 |
| Builder | Greater Homes | Toll Brothers | Morrison Homes |
| Total Homes | 134 | ~440 | 93 |
| Home Sizes | 1,700–3,000+ sq ft | 2,700–4,700+ sq ft | ~1,560–2,820 sq ft |
| Gated | Yes (electronic card) | Yes (24-hour guard) | No |
| Internal Park | Yes (playground, court, shelter) | Yes (full amenity center) | No |
| CDD Fee | No | No | No |
| Distance to Disney Entry | <1 mile | <1 mile | ~3 miles |
💡 Value Proposition: Cypress Chase's structural advantage is being the smallest of the three communities while still offering both gated entry and an internal park, at an early-2000s price profile. Buyers who want newer construction or guard-gated security will find that in Royal Cypress Preserve at a different price point; buyers willing to skip the gate for a slightly newer build will find that in Arlington Bay. Cypress Chase fills the middle.
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Cypress Chase HOA & CDD Information
Cypress Chase is governed by the Cypress Chase Homeowners Association, which manages the gate, the interior park, common-area landscaping, and architectural review. The community has an active Architectural Review Board (ARB) that requires submissions for any exterior modification — a standard reserve-and-standards setup typical of Greater Homes communities of this era.
Cypress Chase does not have a Community Development District (CDD) assessment. This is a meaningful financial difference compared to many newer Windermere-area communities (particularly in Horizon West) where annual CDD assessments commonly run $1,500–$5,000+ on top of HOA dues.
💰 HOA Fees & Management Contact
HOA fees and management company information often change. Please contact us and we will be happy to provide you with the current HOA fee, payment schedule, and direct contact information for the HOA management company. We can also check for you to see if there are any current or upcoming special assessments.
📋 What HOA Fees Typically Cover
- Gate and electronic card access maintenance
- Interior community park upkeep (playground, picnic shelter, basketball court, open field)
- Pond maintenance (water quality, fountain operation where applicable)
- Common-area landscaping and entrance signage
- Street lighting on private interior roads
- HOA management and administrative services
- Architectural Review Board operations
- Reserve fund contributions
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David Myers
