Cypress Woods
A Windermere gated community under mature cypress canopy off Chase Road.
Live the MaxLife.
$1.5M
Median Price
$1M – $2.5M
110
Homes
$250–$400
Monthly HOA
1996
Established
Windermere Elementary
School Zone
Cypress Woods — Market Pulse
Active listings + recent-sold aggregates from the Stellar MLS, 34786 area · about $281/sq ft · aggregate statistics only, no addresses or individual listings published.
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Background
A brief history
Cypress Woods was developed in the mid-1990s on a Chase Road parcel that retained a significant stand of bald cypress and mature live oaks — trees that the original plat deliberately preserved by routing streets and lots around them. Roughly 110 custom lots were released and built out between 1996 and 2006, mostly as one-off customs in Mediterranean and traditional styles. The tree-preservation emphasis and the community's relatively small scale have kept it quiet and stable; turnover is modest (three to six sales a year) and many original owners remain in place.
The feel
What it's like to live here
Cypress Woods feels like one of the more naturalistic Windermere gated communities — less manicured than Tildens Grove, less resort-scale than Keene's Pointe. The tree canopy is the defining visual feature. Streets are narrow two-lanes routed through preserved stands of cypress and oak; interior homes sit back from the road on deep front lawns shaded by decades-old trees. Lots run 0.4 to 0.8 acre, generous for the price band. Architecture is predominantly late-1990s Mediterranean with tile roofs and stucco, with a minority of traditional and transitional customs.
The details
What to expect
Architecture & Lots
Predominantly 1996–2006 Mediterranean and traditional custom homes. A minority of 2018+ transitional rebuilds. Main homes 3,500–5,800 square feet. Lots 0.4 to 0.8 acre with preserved cypress and live-oak canopy.
Lifestyle & Amenities
Keypad gated entrance, small neighborhood park, walking paths through preserved tree stands. No community pool or clubhouse — the trade is lower dues and a quieter community. Residents often carry memberships at Keene's Pointe's Golden Bear Club or Isleworth.
HOA Rules & Fees
Monthly dues $250–$400. Active architectural review — exterior changes require pre-approval. Tree removal requires HOA approval plus replacement-tree planting in most cases. Short-term rentals prohibited; 6-month minimum lease.
Schools
Zoned for Windermere Elementary, Bridgewater Middle, and Olympia High. Windermere Prep (private) is 6 minutes.
Access & Commute
Five minutes to Windermere downtown, 8 minutes to the 429, 15 minutes to Disney, 20 minutes to Restaurant Row, 30 minutes to MCO. Chase Road gate is among the quieter Windermere entrances at peak times.
Community
Amenities
- Keypad gated entrance off Chase Road
- Preserved bald-cypress and live-oak canopy
- Walking paths through preserved tree stands
- Neighborhood park
- 0.4 to 0.8 acre lots
Know Before You Buy
HOA rules worth knowing
- Monthly HOA $250–$400
- Tree removal requires HOA approval plus replacement planting
- All exterior changes require architectural review
- Short-term rentals prohibited; 6-month minimum lease
Education
School assignments
- Windermere Elementary
- Bridgewater Middle School
- Olympia High School
- Windermere Prep (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 $1.4M–$1.65M band. Smaller interior homes move $1M–$1.35M. Well-renovated larger homes run $1.55M–$2M. Recent custom rebuilds on best-in-community lots have closed $2.2M–$2.5M. Price-per-square-foot runs $305 for dated originals to $400 for renovated. Days-on-market has averaged 30–55 days.
Active MLS Inventory
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Homes available in Cypress Woods
12 homes currently listed in Cypress Woods.
$724,900
6363 Sedona Leaf Ct
Windermere, FL 34786
4 bd · 3 ba · 2,665 sqft
Eden Isle Boat Ramp
MLS ID #O6416993, RE/MAX 200 REALTY.
Listing provided by Stellar MLS
$2,225,000
1136 Lake Whitney Dr
Windermere, FL 34786
4 bd · 6 ba · 5,722 sqft
Reserve At Belmere Ph 02 48 144
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6405536, VISTA CAY REALTY COMPANY.
Listing provided by Stellar MLS
$1,439,000
12411 Montalcino Cir
Windermere, FL 34786
4 bd · 5 ba · 3,399 sqft
Casa Del Lago
MLS ID #O6400067, VISTA CAY REALTY COMPANY.
Listing provided by Stellar MLS
$2,200 /mo
8256 Maritime Flag St #1706
Windermere, FL 34786
3 bd · 2 ba · 1,455 sqft
Lakeside/Lks/Windermere
MLS ID #S5155002, MAGNUS REALTY GROUP LLC.
Listing provided by Stellar MLS
$1,572,000
33 Main St
Windermere, FL 34786
4 bd · 2 ba · 2,130 sqft
Davis Shores
MLS ID #O6406887, SAND DOLLAR REALTY GROUP INC.
Listing provided by Stellar MLS
$624,900
6601 Duncaster St
Windermere, FL 34786
4 bd · 3 ba · 3,001 sqft
Lakes/Windermere Ph 02a
MLS ID #O6416272, ANTS REALTY LLC.
Listing provided by Stellar MLS
Also Worth Seeing
Related communities
Windermere
Keene's Pointe
Windermere's guard-gated Jack Nicklaus community on the Butler Chain.
$900K – $5M · 1,100 homes
Explore Keene's Pointe →
Windermere
Tildens Grove
A guard-gated Windermere custom-estate community with resort amenities.
$1.4M – $4M · 175 homes
Explore Tildens Grove →
Windermere
Casabella
A small Tuscan-inspired enclave behind Windermere's quieter gate.
$2M – $4.5M · 50 homes
Explore Casabella →
Windermere
Ridgewater
A mid-size gated Windermere community with resort amenities.
$750K – $1.6M · 260 homes
Explore Ridgewater →
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of August 4, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA