Cypress Landing
A small Dr. Phillips pocket of custom homes under mature cypress and oak canopy.
Live the MaxLife.
$1.1M
Median Price
$700K – $1.6M
85
Homes
$60–$120
Monthly HOA
1989
Established
Windy Ridge K-8 School
School Zone
Search Homes for Sale in Cypress Landing
Stellar MLS · 2026-04-26 · 2 closed sales
Recent market data
Median sold
$805,000
$725K – $885K
$/sqft
$261
Median DOM
61
days on market
First access
Get notified when a Cypress Landing home hits the market.
VIP members see new Cypress Landing inventory 48 hours before Zillow.
Background
A brief history
Cypress Landing was developed in the late 1980s on a heavily-wooded parcel near Wallace Road, with the original plat intentionally preserving the stand of mature bald cypress and live oaks the community is named for. About 85 custom lots were released and built out between 1989 and 1999, mostly as one-off customs rather than production homes. The community was designed as non-gated with a lightly-trafficked single entrance, and the original HOA covenants focused more on tree preservation than architectural uniformity. That's why the home stock reads as architecturally varied — everything from 1990 two-story Georgians to 2005 Mediterranean rebuilds sits on adjacent lots.
The feel
What it's like to live here
Cypress Landing has a hidden-pocket quality that distinguishes it from most Dr. Phillips communities. The tree canopy is the most defining feature — bald cypress (unusual for the area and a daily reminder the community abuts the wetland system on the west edge) combined with live oaks creates a shaded interior that feels closer to Winter Park than Dr. Phillips. Lots run 0.3 to 0.6 acre, mostly irregular due to the original tree-preservation layout. The community is non-gated but sees minimal through-traffic because the single entrance off Wallace connects to a dead-end interior loop. Architecturally varied; emotionally consistent — this is a community where residents value the trees more than the curb appeal.
The details
What to expect
Architecture & Lots
Architecturally mixed — late-1980s two-story traditionals, 1990s ranches and Mediterraneans, a handful of 2015+ custom rebuilds. Main homes 2,800–5,000 square feet. Lots 0.3 to 0.6 acre, irregular shapes due to tree-preservation plat. Heavy bald-cypress and live-oak canopy throughout.
Lifestyle & Amenities
Non-gated community with a lightly-trafficked single entrance off Wallace Road. No community pool or clubhouse — the trees and the quiet are the amenity. Residents value the tree canopy and HOA tree-preservation enforcement as much as the architectural variety.
HOA Rules & Fees
Annual HOA $700–$1,450 (roughly $60–$120/month). Tree removal requires HOA approval with a replacement-tree requirement in most cases. No active architectural review on home exteriors. Short-term rentals allowed but uncommon.
Schools
Zoned for Dr. Phillips Elementary, Southwest Middle, and Dr. Phillips High. The First Academy is 12 minutes.
Access & Commute
Five minutes to Restaurant Row via Wallace and Sand Lake, 10 minutes to I-4, 15 minutes to Disney, 25 minutes to MCO and downtown Orlando.
Community
Amenities
- Mature bald-cypress and live-oak canopy — unusual tree mix for Dr. Phillips
- Non-gated with single dead-end interior loop
- HOA tree-preservation covenants
- Irregular lots with natural privacy buffers
- Architecturally varied custom-build community
Know Before You Buy
HOA rules worth knowing
- Annual HOA $700–$1,450
- Tree removal requires HOA approval with replacement requirement
- No active architectural review on home exteriors
- Short-term rentals allowed but uncommon
Education
School assignments
- Windy Ridge K-8 School
- Chain of Lakes Middle School
- Olympia High School
- The First Academy (private)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Current median trades in the $950K–$1.15M band. Unrenovated 1990s originals move $700K–$900K. Well-renovated homes run $1M–$1.4M. The handful of recent custom rebuilds have closed $1.5M–$1.6M. Price-per-square-foot runs $260 for dated originals to $350 for renovated. The biggest value drivers are lot quality (tree cover, irregular shape giving extra privacy) and renovation status. Inventory is chronically thin — typically one to three sales per year.
Active MLS Inventory
Search homes in Cypress Landing
Live MLS search for Cypress Landing is coming online shortly.
In the meantime, get notified when a home in Cypress Landing hits the market — VIP list members see new Cypress Landing inventory 48 hours before it appears on Zillow.
Get Cypress Landing AlertsRecent Work
Recent sales in Dr. Phillips
Representative closings across Dr. Phillips. Our Cypress Landing off-market pipeline is larger than what's shown here.
No recent listings shown yet for Cypress Landing. Join the VIP list to see upcoming inventory first.
Also Worth Seeing
Related communities
Dr. Phillips
Torey Pines
A quiet Dr. Phillips pocket of custom homes under heavy oak canopy.
$600K – $1.8M · 180 homes
Explore Torey Pines →
Dr. Phillips
Orange Tree
Dr. Phillips' established family neighborhood with mature oak canopy.
$500K – $2.5M · 900 homes
Explore Orange Tree →
Dr. Phillips
Sand Lake Hills
The entry point to Dr. Phillips schools without the luxury premium.
$600K – $1.2M · 500 homes
Explore Sand Lake Hills →
Dr. Phillips
Phillips Cove
A mid-price Dr. Phillips gated community with shared amenities.
$650K – $1.3M · 210 homes
Explore Phillips Cove →
Want Cypress Landing homes first?
Hand-picked Cypress Landing matches — 48 hours before MLS. Two to three per month.
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.