Cypress Landing Homes for Sale

About Cypress Landing Neighborhood

Cypress Landing stands out in the north Dr. Phillips market as one of the area's most sought-after non-gated communities, developed across multiple phases between 1994 and 2000 by Reiche Silliman — a respected Central Florida builder known for quality construction and thoughtful community design. The neighborhood's name reflects its wooded, nature-inspired character: mature cypress and oak trees line the interior streets, and Lake Floyd and several ponds provide scenic backdrops that set the community apart from more densely developed alternatives in the zip code.

Homes in Cypress Landing reflect the architectural diversity of its development era, spanning Spanish/Mediterranean, Traditional, Contemporary, and Florida-style designs. Home sizes range from approximately 2,187 to 4,284 square feet, with the community featuring multiple sub-phases including Cypress Landing Phase 1, Phase 2, Phase 3, and the more upscale Estates of Cypress Landing — which includes some of the largest and most refined homes in the neighborhood. All homes in the community exceed 2,000 square feet, positioning Cypress Landing firmly in the move-up market.

The community's Grand Oaks Shopping Plaza — directly across Conroy Windermere Road — provides immediate access to grocery stores, restaurants, and daily services without ever needing to venture onto major arterial roads. Combined with South Kirkman Road to the east and South Apopka Vineland Road to the west, Cypress Landing residents enjoy exceptional connectivity to both the University area corridor and the Dr. Phillips / Sand Lake Road dining district just minutes to the south.

Cypress Landing's HOA maintains the community's on-site amenities — tennis courts, basketball courts, and a playground — and has historically operated with dues in the range of $500–$600 annually, one of the more affordable HOA structures in the Dr. Phillips area. There are no CDD fees, making total annual carrying costs highly competitive for the quality and location of homes provided.

Cypress Landing Location & Connections

Cypress Landing occupies a strategically positioned stretch of north Dr. Phillips, entered off Conroy Windermere Road between South Apopka Vineland Road to the west and South Kirkman Road to the east. The community sits in the 32835 zip code, placing it firmly within the Dr. Phillips school district and amenity zone while benefiting from a slightly more affordable price tier than the southern portions of the community closer to Restaurant Row and the Butler Chain of Lakes.

Lake Floyd borders the western edge of the community, contributing to the neighborhood's green, nature-rich character and providing scenic views from select home sites. Shadow Bay Park — a full Orange County municipal park with trails, courts, and sports fields — lies nearby to the north along Conroy Road. I-4 is accessible via the Conroy Road interchange approximately one mile northeast, and the Florida Turnpike is accessible via Turkey Lake Road, placing virtually all of Central Florida's major destinations within a short drive.

Cypress Landing Amenities & Lifestyle

Cypress Landing delivers the lifestyle hallmarks that have made Dr. Phillips one of Orlando's most sought-after communities — proximity to the theme park corridor, outstanding public schools, Restaurant Row dining — while offering spacious, well-built single-family homes in a natural, tree-canopied setting that feels removed from the bustle of the tourism zone even while being just minutes from it.

The neighborhood's non-gated layout encourages a friendly, open community dynamic. Streets feel safe and walkable, neighbors know each other, and the HOA maintains shared amenities without creating the overhead of a resort-style development. For families seeking quality schools, manageable HOA costs, and room to grow without sacrificing location, Cypress Landing consistently ranks among the top choices in the 32835 zip code.

How Cypress Landing Compares

Cypress Landing occupies a distinctive position in the Dr. Phillips market — it's one of the few communities in the zip code that offers homes consistently over 2,000 square feet, built by a reputable production builder, with mature landscaping and no CDD fees, in a school zone served by one of Florida's top-ranked K-8 schools. For buyers comparing non-gated communities in north Dr. Phillips, Cypress Landing consistently comes out as the leader on home size, school quality, and community character.

Compared to newer communities in the broader Orlando metro, Cypress Landing's 1994–2000 construction era means buyers get established trees and landscaping, infrastructure with a proven track record, and room to add value through targeted renovations — a strategy that has worked well for many homeowners in the community given the strong underlying demand in this zip code.

Cypress Landing HOA & CDD Information

Cypress Landing is governed by a mandatory Homeowners Association that maintains the community's shared amenities — tennis courts, basketball courts, and playground — and ensures community standards are upheld across the multiple phases of the development. Historically, Cypress Landing's HOA dues have been among the more affordable in the Dr. Phillips area, reflecting a focused scope of services rather than resort-style overhead.

Cypress Landing does not have a Community Development District (CDD) fee, which is a significant long-term financial advantage. In communities with CDDs, homeowners often pay $1,500–$4,000+ per year in addition to regular HOA dues. Cypress Landing buyers benefit from no such assessment, keeping annual housing costs competitive relative to the quality and location the community offers. For more about how CDDs work, see What's a CDD?

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