Is Windermere, FL expensive?

The incorporated Town of Windermere is a high-value housing market, but that does not establish what an individual condo should cost. Town-wide housing values cover multiple property types and do not represent the wider postal area. Compare current condo listings alongside regular assessments, reserves and potential special assessments to judge whether a property fits your budget.

Where's the best place to buy a condo in Florida?

The best location depends on how you plan to use your condo and what you need nearby. Consider Windermere against your everyday destinations, preferred shared facilities and ownership budget rather than a statewide ranking. A community with amenities you will regularly use may suit you better than one with more facilities but a less convenient location.

Does this search include townhomes?

This search selects properties classified as Condominium, so it is not a comprehensive search for townhomes. If you are considering both condos and townhomes for sale in Windermere, tell us which layouts and ownership arrangements interest you. We can help you clarify the property type for individual listings before you compare them with other options.

How do I check a condo's assigned schools?

Use the Orange County Public Schools address-search tool with the condo's specific residential address and check the relevant school year. Do not rely on the community name or Windermere mailing address alone. Confirming the assignment for each property on your shortlist gives you a clearer basis for comparing locations if schools are part of your decision.

Windermere, Florida

Windermere Condos for Sale

Explore condos for everyday living or a second home. We'll help you compare locations, shared amenities and ownership costs so you can focus on properties that fit your plans.

Explore Windermere Condo Listings

9 listings

26 days on market
$290,000Price reduced by $5,000 on Oct 19, 2026
11446 Jasper Kay Terrace Unit 202Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
9 days on market
$324,900
8276 Maritime Flag St Unit 1204Windermere, FL, 34786
- 3 beds
- 2 baths
- 1,455 sqft
124 days on market
$397,500Price reduced by $2,499 on Oct 5, 2026
8218 Mystic View Way Unit 2801Windermere, FL, 34786
- 3 beds
- 3 baths
- 1,840 sqft
154 days on market
$299,500
8180 Boat Hook Loop Unit 109Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
152 days on market
$359,000Price reduced by $900 on Oct 14, 2026
14442 Desert Haven Street Unit 4305Windermere, FL, 34786
- 3 beds
- 3 baths
- 1,534 sqft
14 days on market
$350,000
8179 Maritime Flag Street Unit 206Windermere, FL, 34786
- 3 beds
- 2 baths
- 1,332 sqft
19 days on market
$299,997
8168 Boat Hook Loop Unit 302Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
116 days on market
$295,000
8180 Boat Hook Loop Unit 102Windermere, FL, 34786
- 2 beds
- 2 baths
- 1,161 sqft
55 days on market
$320,000
8168 Boat Hook Loop Unit 303Windermere, FL, 34786
- 3 beds
- 2 baths
- 1,442 sqft
Browse all listings9 listings

View all Windermere condos for sale

Understand Your Windermere Address

As you explore Windermere condos for sale, distinguish the incorporated Town of Windermere from surrounding Orange County communities that share its mailing address. A Windermere address does not automatically mean a property sits within town limits, receives town services or qualifies for resident-only recreation privileges. Check the municipality field in the property appraiser's record for each condo you are considering, then confirm the services and access relevant to that location. The listing search is a starting point for finding properties, not proof of municipal boundaries. Establishing the jurisdiction early helps you compare homes on the benefits they actually offer, rather than on a shared place name.

Shared Amenities at Lakeside at Lakes of Windermere

These amenities belong to Lakeside at Lakes of Windermere, distinct from Lakes of Windermere. They are a community example, not features of every listing.

Fitness Close to Home
A fitness center with a children's room puts exercise facilities within the community, useful when planning your everyday routine.
Swimming and Beach Volleyball
The pool has lap lanes for swimming, while beach volleyball adds another option for outdoor recreation without leaving the community.
Places to Gather
A clubhouse with billiards, an outdoor fireplace and barbecue areas provides shared spaces for relaxing and spending time with others.
Tennis, Play and Fishing
Access through the Lake Burden Master Association includes two tennis courts, a playground and a fishing dock for more ways to enjoy time outside.

Everyday Life Around Main Street

Main Street offers useful destinations to consider alongside a condo's shared amenities. The Windermere Branch library at 530 Main Street provides public computers, Wi-Fi, printing and children's learning equipment, making it a practical resource for everyday tasks and family activities. The Windermere Farmers Market takes place on Main Street in front of Town Hall, adding a local-shopping destination to your routine. When comparing properties, map these places from the actual condo address rather than assuming every Windermere community is equally close. Think about how often you would use them and how those trips would fit into a typical week.

Tree-shaded small-town Main Street scene in Windermere, Florida, with sidewalks and modest civic-scale buildings in late-morning light.

Browse Windermere Condos by Asking Price

Explore listings by asking price, then compare association costs and the facilities that matter to you.

Look Beyond the Condo's Asking Price

A useful comparison of condos for sale in Windermere, FL includes the association's finances as well as the purchase price. Request the budget, details of regular and special assessments, reserve information and applicable inspection reports. Reserve studies examine association-maintained building components, existing reserve funds and anticipated repair or replacement spending. Those funding needs can affect assessments, so consider what the documents show about both ongoing costs and future work. Ask which expenses the regular assessment covers and whether any special assessments apply to the property. We can help you frame property-specific questions so your shortlist reflects the ownership commitments as well as the spaces and amenities you like.

Questions About Buying a Windermere Condo

Gaby Sadler

Property Specialist, Serhant

Talk to Gaby before you buy

I can arrange viewings, answer your questions and prepare a personalized rental projection for any home you're considering.

+1 (407) 490-0475 [email protected]

Find a Windermere Condo That Fits Your Plans

Start with the listings, then narrow your choices around the location, facilities and ownership budget that work for you. Whether you want an everyday home or a second home, we can help you frame questions about individual condos and their associations. Share what matters most, from swimming facilities to Main Street destinations, and explore each property on its own merits rather than assuming every Windermere address offers the same benefits.

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