Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
2002 to 2005Years built
1,750 to 3,000 sq ftHome size
GatedEntry
Greater HomesBuilder
Why people move here

A gated neighborhood under a mile from the Disney entrance.

Cypress Chase is about 134 homes built from 2002 to 2005, behind a card-access gate off Winter Garden-Vineland Road. About 51 homes back to a pond, and a park with a pavilion and playground anchors the neighborhood.
The Walt Disney World entrance is less than a mile away, which makes this one of the shortest commutes to the parks in the 32836 zip.
Cast members and Disney-loving relocators who want a gate and the parks next door.

Cypress Chase at a glance

Location: Monterey Cypress Road off Winter Garden-Vineland Road (CR 535)

Builder: Greater Homes

Built: 2002 to 2005

Homes: About 134 homes

Home types: Single-family homes, one and two story

Size: About 1,750 to 3,000 sq ft

Bedrooms: 3 to 5 bedrooms

Entry: Gated

Area: CR 535 & Horizon West Side

Life here

What Cypress Chase has

🛡Gated entry (card access, no guard)
🛠Park with playground
⛺Covered picnic pavilion
🏀Half basketball court
⚽Open field
🌊Pond views from about 51 homes
Proximity

What is close to Cypress Chase

  • Walt Disney World entrance under 1 mi
  • Disney Springs ~3 mi
  • SeaWorld ~8 mi
  • Universal Orlando ~10 mi

Approximate distances from the community entrance. Walt Disney World is roughly 5 to 10 minutes away off-peak. Sand Lake Road, Apopka-Vineland Road and I-4 back up at rush hour and around the theme parks, so send me your work address and I will map your real commute.

Schools

🏫 Castleview Elementary

🏫 Horizon West Middle

🏫 Windermere High

Orange County Public Schools. Zoning changes, so verify every address.

OCPS school locator
The numbers

Cypress Chase market snapshot

$598,700Median sale priceLast 12 months.
38 daysDays on marketMedian cumulative days on market.
8Closed sales4 the year before.
98%Sale-to-list price ratioMedian for the last 12 months.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 15, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Cypress Chase homes for sale right now

Straight from Stellar MLS. Save the search and get new Cypress Chase listings the day they hit.

Start of list of properties

See all Cypress Chase homes for sale
Free guides

Buying or selling in Cypress Chase?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Cypress Chase works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Cypress Chase FAQ

Where is Cypress Chase in Dr. Phillips?

Cypress Chase is in the Winter Garden-Vineland Road side of 32836, toward Horizon West, at Monterey Cypress Road off Winter Garden-Vineland Road (CR 535).

How far is Cypress Chase from Walt Disney World?

Roughly 5 to 10 minutes off-peak from this part of Dr. Phillips. I will map the exact drive from the entrance before you choose.

When were homes in Cypress Chase built?

2002 to 2005, by Greater Homes.

What amenities does Cypress Chase have?

Gated entry (card access, no guard), Park with playground, Covered picnic pavilion, Half basketball court, Open field, Pond views from about 51 homes.

Is Cypress Chase a gated community?

Yes. Cypress Chase has a gated entry. I confirm gate type and access rules for any home before you write an offer.

What schools serve Cypress Chase?

Schools commonly listed for this community: Castleview Elementary, Horizon West Middle, Windermere High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Cypress Chase in the City of Orlando?

Cypress Chase has an Orlando mailing address, but the Orange County Property Appraiser record I checked places it in unincorporated Orange County, so county services and county tax rates apply. A few Dr. Phillips neighborhoods are inside city limits, so I confirm the jurisdiction for every address.

Is Cypress Chase zoned for Dr. Phillips High?

Not usually. Windermere High is the high school most often listed for Cypress Chase. Dr. Phillips addresses are split among Dr. Phillips High, Lake Buena Vista High, Olympia High and, on the CR 535 side, Windermere High, so I check the OCPS School Locator for every address.

What do homes in Cypress Chase sell for?

Per Stellar MLS, the median sale price in Cypress Chase was $598,700 across 8 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.

Your next step

Thinking about Cypress Chase?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Cypress Chase, straight from Stellar MLS
  • City or county, HOA and lake access for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719
More in CR 535 & Horizon West SideArlington BayLake Sheen ReserveRoyal Cypress PreserveAll Dr. Phillips communities
Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify jurisdiction (unincorporated Orange County or City of Orlando), school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.