Cypress Landing
Cypress Landing: Local Questions Answered
Where is Cypress Landing located?
Cypress Landing is off Conroy Windermere Road near Dr. Phillips Boulevard, on Winding Lake Circle, Bellington Drive, Belshire Drive, Beech Tree Drive and nearby streets. Homes have Orlando 32835 mailing addresses and are in unincorporated Orange County. It is outside the Census Bureau's Doctor Phillips census-designated place, but realtor community guides and MLS listings market it as part of the Dr. Phillips area.
What types of homes are in Cypress Landing?
Cypress Landing has 218 single-family homes built from 1994 to 2000, according to Orange County Property Appraiser records. Homes range from about 2,190 to 4,290 square feet on lots of about a third of an acre, most are two-story, and nearly all have a pool. MLS listings show 4 to 6 bedrooms. There are no townhomes or condos.
How much do homes cost in Cypress Landing?
Over the past two years (MLS data, October 2026), homes in Cypress Landing sold 15 times for a median of about $855,000, ranging from about $650,000 to $1 million. For today's listings, see the top of this page.
What are the HOA fees in Cypress Landing?
Recent MLS listings show HOA dues of about $54 to $60 per month as of October 2026. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Cypress Landing, but check the property tax bill for any special assessments. The association is Cypress Landing of Orange County Homeowners' Association, Inc.
What schools serve Cypress Landing?
Orange County Public Schools' 2026-27 school zones place Cypress Landing in Windy Ridge School (K-8), Chain of Lakes Middle and Olympia High School. Windy Ridge serves as the elementary school and sits at the community's north end.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
Is Cypress Landing the same as Cypress Point?
No. Cypress Point is a separate guard-gated community. Cypress Landing is also unrelated to Cypress Landing in Clermont and other developments with the same name. Its six lakefront homes are on Lake Floyd, not Lake Floy in Lake Marsha.
Can you rent homes in Cypress Landing short term?
No Cypress Landing-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
