Windermere · Southwest Orange County · 34786

Casabella Homes for Sale in Windermere, FL

A high end single family neighborhood in Windermere with large homes built 2015 to 2020, set mostly along Isabella Circle. Here is what 12 Stellar MLS closings over the last 36 months say about price, pace and home size, plus where to search what is listed today.

Written by Jared Jones Updated October 2026 Jared Jones Team, Brokered by eXp Realty

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Current Casabella homes on the market.

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$3,097,500Median sold price (12 closed sales, last 36 months)
118.5 daysMedian days on market (CDOM, last 36 months)
2016 to 2018Typical year built (middle 50% of homes sold)

Data: Stellar MLS closed sales over the last 36 months, export pulled Oct 14, 2026. This page uses a 3 year window because Casabella has few closings in any single year.

At a glance (as of October 2026)
FactFigure
Closed sales (last 36 months)12
Median sold price (36 months)$3,097,500
Median sold price per sq ft$444
Median days on market (CDOM)118.5
Typical year built (middle 50%)2016 to 2018
Single family sales12 (median $3,097,500)
Active listings on Oct 14, 20265
ZIP code34786

Sources: Stellar MLS (sold closings last 36 months (Stellar MLS export pulled Oct 14, 2026; closings in file run Aug 2, 2024 to Jul 24, 2026)); Stellar MLS active listings export, Oct 14, 2026. Includes the legal subdivision names CASABELLA and CASABELLA PH 2, which are phase variants of the same community.

Where is Casabella in Windermere?

Casabella is a single family neighborhood in Windermere, inside the 34786 ZIP code in southwest Orange County. Nearly every home in the sold sample sits on Isabella Circle, with one on Casabella Drive. For the wider picture, start with the Windermere Real Estate guide.

Location snapshot

  • City: Windermere, FL
  • ZIP: 34786
  • Streets: Isabella Circle, Casabella Drive
  • County: Orange

What this data covers

  • Window: Aug 2, 2024 to Jul 24, 2026 closings (36 months)
  • Source: Stellar MLS
  • Plats: Original plat and Phase 2
  • Homes: Single family, fee simple

What amenities does Casabella include?

The Stellar MLS pool field shows a private pool for 11 of the 12 homes that sold in the last 36 months. The export does not list community amenities. HOA and CDD amounts are not in the MLS export, so none are listed on this page. Confirm current dues, what they cover and the association rules in writing before you write an offer.

Private poolsRecorded for 11 of the 12 homes sold
Large floor plans4,339 to 8,372 heated square feet in the sold sample
Confirm in writingCurrent amenity list, HOA dues and association rules

Buyers shopping this price range often compare Windermere with nearby markets. The Dr. Phillips Real Estate guide and Best Private Clubs in Orlando (2026) cover the options.

What do Casabella homes typically look like?

Every closing in the last 36 months was a single family home held fee simple, with 5 to 7 bedrooms and between 4,339 and 8,372 heated square feet. Sold prices ran from $2,100,000 to $3,600,000, with a median of $3,097,500 and a median of $444 per square foot.

The homes date from 2015 to 2020, so they are newer than most Windermere resale at this price, but lot, floor plan size and finish level still move one sale away from the next.

The median CDOM is 118.5, and several homes took more than 6 months to sell. At this price, buyers take their time, so pricing against the closest comparable sales matters from day one. The 5 active listings on Oct 14, 2026 were all on Isabella Circle.

How does Casabella compare to nearby Windermere options?

Casabella competes with the top tier of Windermere neighborhoods for the same buyer. Compare it with Keene’s Pointe, and read Orlando Gated Communities: Worth It? (2026) if a gate is on your list.

Winter Garden & Horizon West area overview. Area context, not specific to Casabella. Watch when you want the bigger picture, and prefer the sold stats table on this page for prices.

Video: Jared Jones Team / YouTube

Frequently asked questions

What is the median sold price in Casabella?

The median sold price is $3,097,500 across 12 Stellar MLS closings in the last 36 months. All 12 were single family homes, and the median price per square foot was $444.

How long do homes take to sell in Casabella?

The median days on market (CDOM) is 118.5 across the 12 closings in the last 36 months. CDOM counts cumulative days, including time before a relisting.

How large are the homes in Casabella?

Homes that sold in the last 36 months had 5 to 7 bedrooms and between 4,339 and 8,372 square feet, and 11 of the 12 recorded a private pool. The middle 50% were built between 2016 and 2018.

Where is Casabella located?

Casabella is in Windermere, Florida, ZIP 34786, in southwest Orange County. Its streets include Isabella Circle and Casabella Drive.

Are there homes for sale in Casabella right now?

Stellar MLS showed 5 active listings in Casabella on Oct 14, 2026. The live listings feed on this page updates automatically, or call or text the Jared Jones Team at 407-706-5000 to set an alert for new Casabella listings.

Browse nearby

Thinking about a home in Casabella?

Get the closest comparable sales on a specific home, a read on how it stacks up against recent Casabella sales, or a pricing plan for your sale. Call or text the Jared Jones Team at 407-706-5000.

About the author

Jared Jones

Jared has 24 years in real estate, the last 11 in Central Florida, with nearly 4,000 homes sold and a top 10 eXp team in Florida. The Jared Jones Team, Brokered by eXp Realty, works Ocoee, Winter Garden, Horizon West and the greater Orlando metro. Office: 504 W Plant Street, 1st and 2nd Floors, Winter Garden, FL 34787. Phone: 407-706-5000. Email: info@jaredjones.com.

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