Windermere

Butler Chain estate living and Disney area premium inventory

Orange County, Florida

Renting in Windermere

Here is the picture for renting in Windermere today: 58 active rentals, ranging from $1,550 to $15,000 per month, in an Orange County market. Named places such as Butler Chain of Lakes, Isleworth Golf and Country Club, and Keenes Pointe shape where renters want to be. Waterfront and lake-view rentals are in demand here, so lakefront homes tend to lease quickly. Golf-community addresses such as Isleworth Golf and Country Club draw their own steady demand.

Three-bedroom and four-bedroom homes make up most of the current availability, and what is listed runs mostly to single-family homes and townhomes. Listings currently active here have spent an average of 45 days on the market.

Every matching Windermere rental is in reach, whichever brokerage lists it, because NAH Rental Homes represents renters across the full Stellar MLS. Describe the home you want at TenantMatch and it builds the search for you.

Windermere Market Snapshot

$2,988/mo
Median Rent
45 days
Avg Days on Market
58
Active Listings
2026-07-30
Last Updated

Live count from the current MLS rental feed; figures update as inventory changes.

About Windermere

Windermere sits in western Orange County along the Butler Chain of Lakes and contains some of Central Florida's most exclusive lakefront and estate inventory. The town of Windermere itself is a small incorporated municipality of roughly 4,000 residents organized around a network of historic lake roads, but the broader Windermere ZIP code 34786 covers a much larger residential footprint that includes the Isleworth, Keenes Pointe, Lake Burden, and Reserve at Belmere gated communities, as well as a substantial inventory of unincorporated estate properties along the Butler Chain. Isleworth sits at the eastern edge of the ZIP code and remains one of the metro's most identified high end golf and lakefront communities, with custom estate construction on lots typically ranging from half an acre to over five acres and several parcels with deeded Butler Chain frontage. Keenes Pointe features over 1,100 homes on quarter acre to one acre lots organized around a Jack Nicklaus designed golf course and a private community lakefront facility on Lake Tibet Butler. The Reserve at Belmere and the surrounding Lake Burden corridor feature 2000s and 2010s Mediterranean Revival construction on quarter acre to half acre lots. The historic Windermere downtown area along Main Street features early 20th century cottages on tree shaded lots, with strict architectural review for any new construction or significant remodel work. The architectural inventory across the broader Windermere area leans heavily on custom Mediterranean Revival, Florida traditional, and contemporary construction from the 1990s through the 2020s. Lakefront parcels along the Butler Chain command the area's strongest pricing per square foot and remain the most liquid segment of the local market regardless of cycle. Lot sizes range from quarter acre interior parcels in master planned sub communities to over ten acre estate parcels on the Butler Chain. Commute access is strong: State Road 535 and Apopka Vineland Road run north south through the corridor and connect directly to the 408 East West Expressway and the 429 Western Beltway, the 429 itself runs along the western edge of the ZIP code with interchanges at Stoneybrook West Parkway and Western Way, and the 408 runs east through the corridor to downtown Orlando. Walt Disney World sits immediately south of Windermere, and the Disney area commercial inventory along Vineland Road and the I-4 corridor provides extensive retail, dining, and entertainment access. Orlando International Airport is reachable within thirty five minutes via the 417 toll road. Sellers preparing properties in Windermere typically benefit from emphasizing Butler Chain access where applicable, gated community amenities, golf course frontage, and lot size in marketing materials.

Notable Points of Interest

Housing Stock and Lot Pattern

Windermere's housing stock skews toward custom estate construction from the 1990s through 2020s inside gated golf and lakefront communities such as Isleworth and Keenes Pointe, with a smaller share of historic early 20th century cottages in the town center and a substantial inventory of unincorporated estate parcels along the Butler Chain. Lot sizes range from quarter acre interior parcels to over ten acres on the Butler Chain.

Available Rentals in Windermere

Showing 24 of 58 active rentals in Windermere.

View all 58 rentals in Windermere

Windermere Map

Windermere Rental Questions

What is it like to rent in Windermere?
Renting in Windermere means searching a Orange County market anchored by Butler Chain of Lakes, Isleworth Golf and Country Club, and Keenes Pointe. You work through a structured search, tour the rentals that fit your criteria, and have NAH Rental Homes represent you from application to move-in.
How much is rent in Windermere?
Right now there are 58 active Windermere rentals, ranging from $1,550 to $15,000 per month, spanning single-family homes and townhomes. Rents move with the property type, size, and location, so the live count is the most reliable guide.
What does working with NAH Rental Homes cost a renter in Windermere?
NAH Rental Homes represents renters across the full Stellar MLS in Windermere, and any renter-side terms are set out in writing in your tenant representation agreement before you tour. You see every matching rental, NAH-managed or not, with no ranking tricks and no surprise charges.
What is the fastest way to find a rental in Windermere?
Start with TenantMatch, our intelligent intake at /tenantmatch. You describe the home you want in your own words, and it builds a precise Windermere rental search, ranks the closest matches, and flags new listings as they appear.
What landmarks and amenities define Windermere?
Windermere is anchored by Butler Chain of Lakes, Isleworth Golf and Country Club, and Keenes Pointe, along with Windermere Historic Downtown and Walt Disney World Resort. These named places shape day-to-day life and rental demand.

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