- 5 beds
- 5 baths
- 5,511 sqft

Windermere, Florida
2nd Avenue Windermere Homes for Sale
Compare East and West 2nd Avenue locations, access to town facilities and property-specific waterfront features. Review 2nd Avenue Windermere homes for sale with us.
Browse 2nd Avenue Windermere Homes for Sale
2 listingsBrowse 2nd Avenue properties by price
Search price ranges within this area while keeping the property criteria for this page.
Recent sales near 2nd Avenue
4 properties sold within half a mile in the last 12 months · median $1,812,500
106 Palm Street5 bed · 5 bath · 3,082 sqft
$1,375,000
Sold Jun 11, 2026
105 Pine Street5 bed · 6 bath · 5,696 sqft
$2,335,000
Sold Jun 10, 2026
409 W 2nd Avenue5 bed · 5 bath · 4,688 sqft
$2,250,000
Sold Mar 9, 2026
299 W 4th Avenue4 bed · 3 bath · 2,410 sqft
$862,000
Sold Jan 8, 2026
2nd Avenue Inventory at a Glance
A snapshot of properties for sale and median asking price in the 2nd Avenue search area.
- For sale now
- 2
- Median asking price
- $4,450,000
Explore the 2nd Avenue Windermere Search Area
Use the map to orient your home search, then compare each property's location with Main Street, local parks and the lakeside setting.
How we compare 2nd Avenue Windermere homes for sale
We compare 2nd Avenue Windermere homes for sale by location, homesite and the way you want to live. East and West 2nd Avenue offer different relationships to Main Street and the water, so we start with the individual address rather than treating the street as one subdivision. Park Among the Lakes, between East 2nd and 3rd Avenues on Main Street, and Palmer Park at 418 W 2nd Avenue are useful reference points when viewing homes. We help you weigh access to town recreation against the space, privacy and waterfront features of each property, then build a shortlist around the details that matter to you.
Recreation at Park Among the Lakes
These are town facilities, not private amenities attached to a home or a 2nd Avenue association. Court use is reserved for eligible residents.
Resident-Only Tennis Courts
Three secured, lighted tennis courts offer a local recreation option for eligible residents who want to make tennis part of their routine.
Resident-Only Pickleball Court
One secured, lighted pickleball court adds another option for eligible residents interested in active recreation close to Main Street.
Picnic Tables and Benches
Picnic tables and benches provide places to sit, share a picnic or take a break, giving the park a role beyond court sports.
Parking and a Bike Rack
Parking and a bike rack support visits by car or bicycle. Consider the route from each home when deciding how the park fits your routine.
Everyday Life Around Main Street
Main Street offers practical resources for both full-time living and time spent at a second home. The Windermere Branch library at 530 Main Street has public computers, Wi-Fi, printing and children's learning resources, alongside classes and events. It can be a useful stop for everyday tasks or an activity with the family. At Town Square Park, 520 Main Street, the farmers market runs along Main Street between 5th and 6th Avenues on Fridays from 9 a.m. to 1:30 p.m., weather permitting. Produce, bread, coffee and flowers are among the offerings. When comparing homes, consider how these destinations fit your weekly routine and check the route from the particular property you are considering.
A Lakeside Setting, With Property-Specific Details
For waterfront buyers, our first question is what you want to do on the water. West 2nd Avenue includes properties on Wauseon Bay beside Lake Butler, while the historic boathouses opposite Palmer Park give the street its lakeside character. We distinguish a water view from frontage, documented access and a usable dock. That makes it easier to compare a home for its setting with one that supports your boating plans. Before you commit, we help identify the frontage, dock rights and access documents to review for the specific property.
Compare gated and lake-oriented settings
For a comparison with gated communities in the wider Windermere area, explore Lake Butler Sound homes for sale and Isleworth homes for sale. A community’s lake setting does not establish frontage, boating rights or private dock access for every home.
2nd Avenue Windermere Homes for Sale: FAQs

Gaby Sadler
Property Specialist, Serhant
Explore 2nd Avenue Windermere homes for sale with Gaby
Tell me your budget and the features you want from a home around East or West 2nd Avenue. I'll help you compare 2nd Avenue Windermere homes for sale, assess each location and focus your shortlist on the waterfront features, town access and ownership details that matter to you.
Find Your Home in Windermere
Your choice near 2nd Avenue starts with how you want to live. You might prioritize town recreation, the library and farmers market on Main Street, or a property with its own connection to the water. We can help you explore homes for sale and discuss the details that matter to your everyday routine or second-home plans. Bring us your priorities so we can help you compare individual properties, keeping the home's features and location at the center of your search.
Explore more
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