Dr. Phillips · 32835 · Conroy Road Corridor

Cypress Landing

A well-established Dr. Phillips neighborhood of executive-style homes — spacious floor plans, mature landscaping, community amenities, and quick access to Restaurant Row and the theme park corridor.

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Live the MaxLife.

$500K – $800K

Price Range

2,300 – 3,900 sq ft

Home Sizes

~$600/year

HOA

Dr. Phillips High (A)

Top School

Overview

Cypress Landing is a single-family home community in the Dr. Phillips area of Orlando, located off Conroy Road in the 32835 zip code. The neighborhood was developed between 1994 and 1998 by Reiche Silliman, with homes featuring Spanish/Mediterranean, Traditional, Contemporary, and Florida architectural styles. Floor plans run from approximately 2,300 to 3,900 square feet with 2 to 3 bedrooms and two- to three-car garages. The community is non-gated and open to through-traffic but maintains strong curb appeal through its active HOA. Cypress Landing sits roughly 11 miles from Downtown Orlando and approximately 5 miles from Walt Disney World, placing it at the heart of the Dr. Phillips lifestyle corridor.

Community Amenities

Cypress Landing's HOA — approximately $600 per year — funds a community park, playground, basketball half-court, and tennis court. The amenities are modest compared to guard-gated neighbors but serve the neighborhood well for casual recreation. The tree-lined streets and well-maintained common areas reflect active HOA oversight. The neighborhood's location along the Conroy Road corridor puts Grand Oaks Village shopping plaza, multiple Publix and Whole Foods locations, and Restaurant Row within a short drive.

Schools

Cypress Landing falls within Orange County Public Schools. The typical feeder pattern routes students from Palm Lake Elementary to Chain of Lakes Middle to Dr. Phillips High School, which has consistently earned an A rating from the Florida Department of Education. Dr. Phillips High is one of Orange County's strongest comprehensive high schools, with strong performing arts, athletics, and college placement programs. Buyers should confirm exact school zoning at ocps.net, as address-level assignments can vary along the 32835 boundary.

Location & Daily Life

The Conroy Road address puts Cypress Landing in ideal position for the Dr. Phillips lifestyle. Restaurant Row (Sand Lake Road's dining district with 50+ restaurants) is 5–8 minutes away. The Mall at Millenia is 10 minutes northeast on I-4. Universal Orlando is approximately 10–15 minutes. Walt Disney World is about 15–20 minutes via Conroy Road to I-4 or the Florida Turnpike. Orlando International Airport is approximately 25–30 minutes southeast. I-4, SR-408, and the Florida Turnpike are all accessible within a few minutes, giving the neighborhood excellent regional connectivity.

Real Estate Market

Cypress Landing homes have appreciated steadily alongside the broader Dr. Phillips market. The 2,300–3,900 sq ft executive floor plans attract move-up buyers, professionals working in the theme park and hospitality corridor, and families prioritizing Dr. Phillips High School's A rating. Homes in good condition with updated kitchens and screened pools command the strongest prices. The community's non-gated status and modest HOA fees translate to lower carrying costs than adjacent gated neighborhoods, which appeals to buyers who value the Dr. Phillips address without premium HOA overhead.

What Makes Cypress Landing Special

Executive-style homes 2,300–3,900 sq ft built by Reiche Silliman (1994–1998)
Community tennis court, basketball half-court, park, and playground
HOA ~$600/year — no CDD fees, no guard-gate premium
Dr. Phillips High School (OCPS A-rated) feeder
5 miles to Disney · 10 min to Universal · 10 min to Restaurant Row
Mature landscaping and Spanish/Mediterranean architectural variety
Quick access to I-4, SR-408, and the Florida Turnpike

Around Cypress Landing

Cypress Landing community entrance, Dr. Phillips, Orlando, FL

Cypress Landing entrance corridor, Dr. Phillips, Orlando, FL

Cypress Landing FAQ

Is Cypress Landing gated?

No — Cypress Landing is a non-gated neighborhood. The community is open to through-traffic but is maintained to a high standard through an active HOA. Buyers who want a gated Dr. Phillips address may also consider neighboring communities, though Cypress Landing's lower HOA and carrying costs are a meaningful trade-off.

What are the HOA fees in Cypress Landing?

The HOA runs approximately $600 per year (roughly $150/quarter), which covers the park, playground, tennis and basketball court maintenance, and common area upkeep. There are no CDD fees in Cypress Landing, making total carrying costs competitive relative to newer communities.

What schools serve Cypress Landing?

The standard OCPS feeder is Palm Lake Elementary → Chain of Lakes Middle → Dr. Phillips High School. Dr. Phillips High is one of Orange County's consistently A-rated comprehensive high schools. Always confirm the exact school assignment for your specific address at ocps.net before purchase.

How does Cypress Landing compare to gated Dr. Phillips communities?

Cypress Landing offers the same Dr. Phillips school zone and location advantages as gated neighbors at a lower HOA cost and without gate-access constraints. The homes are similarly sized executive floor plans from the mid-1990s. Trade-offs are the absence of a guardhouse and the lower land values relative to fully gated or lakefront communities.

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Nearby Neighborhoods

Neighborhood

Dr. Phillips

Luxury estates, OCPS schools, and Sand Lake Chain waterfront living — minutes from Restaurant Row, Bay Hill, and Central Florida's finest attractions.

Explore Dr. Phillips→

Neighborhood

Windermere

Picturesque lakefront estates, tree-lined streets, and the true small-town feel of Central Florida's most coveted address on the Butler Chain of Lakes.

Explore Windermere→

Neighborhood

Isleworth

An exclusive golf and waterfront community offering world-class amenities, architectural excellence, and unrivaled prestige — one of Florida's most coveted addresses.

Explore Isleworth→

Neighborhood

Willow Wood

A well-established Dr. Phillips community with 130 homes on half- to full-acre lots — mature oak canopy, community tennis, a nature trail, and a quiet residential character between Restaurant Row and Windermere.

Explore Willow Wood→

Neighborhood

Wingrove Estates

An established Dr. Phillips neighborhood of 79 homes on the Conroy Windermere Road corridor — Florida and Contemporary architecture, mandatory HOA, and the Grand Oaks Village plaza immediately to the east.

Explore Wingrove Estates→

Before making an offer

Verify key facts with official sources

All information on this page reflects market data and research as of April 2026. Markets change, HOA bylaws are updated, school assignments shift, and flood maps are revised. Before making an offer or relying on any of the following for a purchase decision, confirm directly with official sources:

•School zones & ratings: Verify current assignment at OCPS.net (Orange County) or your local district
•HOA fees & rules: Request current documentation from the HOA or property manager; fee schedules can change annually
•Flood zones & elevation: Check FEMA's Flood Map Service Center for current designations
•Market statistics: These reflect recent closed sales; verify with current MLS data before negotiating
•Zoning & restrictions: Confirm with Orange County Property Appraiser and county zoning records

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