About Casabella at Windermere
I've shown homes in Casabella and this community is truly one of Windermere's hidden gems. If you're looking at Casabella homes for sale, you're considering one of the most exclusive gated communities in Windermere, FL. It's a boutique neighborhood of just 79 Mediterranean style estate homes, all built exclusively by Toll Brothers between 2013 and 2019.
Every home in Casabella sits on a half-acre or larger homesite, giving residents the kind of space and privacy that's increasingly difficult to find in Central Florida. The community features barrel tile roofs, brick paver driveways, mature Mediterranean landscaping, and a cohesive architectural identity that sets it apart from newer production-style developments.
Casabella is fully gated with controlled access, and with only 79 homes total, the community maintains a quiet, private feel that larger subdivisions simply can't replicate. There are no CDD fees, which is a meaningful cost advantage over many surrounding communities in the Windermere and Horizon West corridor.
Casabella Pricing and Market Data
Casabella Market Snapshot
Casabella homes range from approximately $2.85 million to $5 million depending on square footage, lot position, and interior upgrades. Recent closed sales have ranged from $2.1M to $3.3M. Homes in premium positions or with extensive upgrades command higher prices. Data as of June 2026. Contact me for current availability.
Casabella isn't a high-turnover neighborhood. With only 79 total homes, listings are infrequent, and desirable lots with upgraded interiors tend to sell quickly. If you're considering a purchase in Casabella, working with a Realtor who monitors this community closely is essential.
Home Sizes and Floor Plans
Casabella homes range from approximately 3,100 square feet to over 6,900 square feet, with the largest estates reaching up to 8,372 square feet under air. Most homes feature 5 to 6 bedrooms and 6 to 9 bathrooms, reflecting the Toll Brothers commitment to spacious, well-appointed living.
- Smallest homes: approximately 3,100 sqft with 4-5 bedrooms
- Mid-range homes: approximately 5,000-5,500 sqft with 5-6 bedrooms
- Largest estates: 6,900-8,372 sqft with 6+ bedrooms, media rooms, offices, and bonus spaces
- All homes sit on half-acre or larger lots with generous setbacks
- Most homes include 3-car garages, outdoor summer kitchens, and screened-in pool areas
Architecture and Design
Casabella's architectural identity is distinctly Mediterranean, with design elements that create a cohesive and upscale streetscape throughout the community.
Barrel tile roofs in earth-toned colors. Brick paver driveways and walkways. Stucco exteriors with stone and architectural detailing. Arched entryways and covered loggias. Mature landscaping with tropical and Mediterranean plantings. Toll Brothers premium standard features including granite, hardwood, and designer fixtures.
Because all 79 homes were built by Toll Brothers, the construction quality is consistent throughout the community. Toll Brothers is recognized as one of the nation's leading luxury homebuilders, and their Casabella homes reflect that standard with premium materials, energy-efficient systems, and thoughtful floor plan designs.
Community Amenities
Casabella offers a curated set of amenities that serve the community's 79 families without the overcrowding that can affect larger developments.
Heated community swimming pool. Community park with open green space. Two decorative ponds with fountains. Brick paver streetscapes throughout the community. Mature Mediterranean landscaping and manicured common areas. Gated entry with controlled access for privacy and security.
Casabella's small footprint is a feature, not a limitation. With only 79 homes sharing these amenities, the pool area stays uncrowded, the park feels private, and the overall atmosphere is quiet and residential rather than resort-style.
HOA Fees and Costs
- HOA: approximately $480 per month, or $1,322-$1,441 per quarter depending on the lot
- CDD fees: NONE. Casabella has no Community Development District fees
- HOA covers gated entry maintenance, common area landscaping, pool maintenance, pond and fountain upkeep, and community insurance
- Homeowners are responsible for their own lawn maintenance, exterior upkeep, and pool care on their individual lots
The absence of CDD fees is a significant advantage. Many newer luxury communities in Horizon West, Water Windermere, and surrounding areas carry CDD assessments of $2,000 to $6,000+ per year on top of HOA dues. Casabella buyers avoid that additional annual cost entirely.
Schools Serving Casabella
Elementary: Windermere Elementary School. Middle: Bridgewater Middle School. High: Windermere High School. Private nearby: Windermere Preparatory School (PK-12 college prep).
All three public schools are part of Orange County Public Schools and are well-regarded in the Windermere area. Always verify current school zoning directly through OCPS Find My School using the exact property address, as school assignments can change.
Location and What Is Nearby
Casabella is located in the heart of Windermere, FL, one of Central Florida's most desirable towns. The community enjoys convenient access to major attractions, dining, and employment centers.
Butler Chain of Lakes. minutes away, one of Central Florida's premier lake systems for boating, fishing, and waterfront living. Downtown Windermere. local shops, dining, and the Windermere Farmer's Market. Restaurant Row (Sand Lake Road). dozens of upscale dining options within 10-15 minutes. Mall at Millenia. luxury shopping with Gucci, Louis Vuitton, Neiman Marcus, and more, approximately 15 minutes east. Walt Disney World. approximately 15-20 minutes south. Universal Orlando and Epic Universe. approximately 20 minutes east. Orlando International Airport (MCO). approximately 30 minutes via FL-528. Florida's Turnpike and 429. easy access to regional highways.
Who Is Casabella Best For?
Casabella Is Best For
May Not Be Ideal For
Casabella vs. Other Windermere Communities
Windermere is home to several prestigious communities. Here is how Casabella compares.
Casabella vs. Isleworth: Isleworth is larger with a championship golf course and higher price points ($3M-$20M+). Casabella offers a more intimate setting without mandatory club dues. Casabella vs. Keene's Pointe: Keene's Pointe is a larger community with a Jack Nicklaus golf course and Lake Tibet access. Casabella is smaller and more private with no golf course commitment. Casabella vs. Lake Butler Sound: Lake Butler Sound offers lakefront living on the Butler Chain. Casabella offers larger lots and newer Toll Brothers construction. Casabella vs. Bridgewater: Bridgewater is a newer community with a broader price range. Casabella is exclusively Toll Brothers with a more cohesive Mediterranean design.
Nearby Communities to Compare
Windermere Homes for Sale, Isleworth Homes for Sale, Keene's Pointe Homes for Sale, Bridgewater Homes for Sale. Lake Butler Homes for Sale, Best Gated Communities in Orlando, Luxury Homes in Windermere, Golden Oak Homes for Sale.
Casabella at Windermere is a gated community that offers a blend of privacy and convenience in the Windermere corridor. The neighborhood features well maintained homes with community amenities, mature landscaping, and a location that keeps you close to Dr. Phillips dining, theme parks, and top rated schools.
Homes in Casabella range from three bedroom townhomes to larger single family residences, giving buyers options at different price points within a gated setting. The community's Windermere address carries weight for school zoning and resale value, making it a strong choice for families and long term homeowners.
Micaela provides detailed insights on Casabella, including current inventory, pricing trends, HOA details, and how the community compares with other gated Windermere neighborhoods. She helps you make a smart buying decision. Call 407.761.5501 to tour Casabella at Windermere.
Work With Micaela Navarra
Micaela Navarra is a licensed Orlando Realtor with M2M Realty, a boutique brokerage that goes the extra mile for every client. As a smaller, more concentrated firm, M2M Realty delivers the kind of personal attention and dedication that larger brokerages simply can't match.
With over 30 years of calling Orlando home, Micaela knows every neighborhood, every school district, and every hidden gem across Central Florida. Whether you're buying your first home, selling a luxury estate, relocating from out of state, or investing in rental property, Micaela provides hands-on guidance from the first conversation through closing day and beyond.
Languages: English, Spanish, Italian, and Portuguese
Call or text Micaela directly: 407.761.5501