Windermere
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Local Area Guide

Windermere

Seller's Market
Avg. List Price
$1,850,000
Days on Market
28 days
Price / Sq Ft
$430
YoY Price Change
+6.1%

Data reflects recent MLS activity · Updated regularly · Consult Jorge for current figures

About this Area

Luxury lakefront living on the Butler Chain — Windermere is where privacy, prestige, and natural beauty come together in one extraordinary address.

The Lifestyle

Windermere is defined by water. The Butler Chain of Lakes — 13 connected lakes — runs right through the community, and boating, paddleboarding, and waterfront sunset dinners are weekend staples. Gated estates, golf courses, and proximity to Disney make this one of Central Florida's most sought-after zip codes. Quiet streets and excellent schools seal the deal for families.

Life Here

A glimpse of the lifestyle

Central Florida Living

Why people love living here

🏊
Butler Chain

13-lake chain perfect for boating, wakeboarding, and sunsets.

🎢
Theme Parks

Disney World is literally next door — under 10 minutes away.

⛳
Golf

Isleworth Golf & Country Club — a PGA Tour favorite.

🌿
Nature Trails

Winding nature paths along the lakeshores and preserve areas.

Market Snapshot

Current real estate trends

Data reflects recent MLS activity · Updated regularly

Seller's Market+6.1% YoY
Avg. List Price
$1,850,000
Median Sold
$1,420,000
Avg. Days on Market
28 days
Price / Sq Ft
$430
32 homes sold in the last 90 days
Jorge's Take

"Windermere's lakefront estates and proximity to Disney make it one of Central Florida's most sought-after luxury submarkets with consistent appreciation."

Price Trends

Home values over the last 12 months

Median sold price · Based on recent MLS activity

Current Median$1.42M
▲ 6.8% vs. 12 mo. ago
Jul '25Oct '25Jan '26Apr '26$1.32M$1.35M$1.38M$1.43M

Estimates based on recent sales activity. Contact Jorge for a precise market analysis.

Education

Schools & education

Orange County Public Schools
District Rating 9/10
Windermere High SchoolHigh SchoolGrades 9–12
9/10

STEM Academy, competitive athletics

Bridgewater Middle SchoolMiddle SchoolGrades 6–8
8/10

AVID program

Windermere ElementaryElementaryGrades K–5
9/10

Consistently top-rated, strong parent involvement

Keene's Crossing ElementaryElementaryGrades K–5
9/10

Science & technology focus

Ratings sourced from GreatSchools.org · Verify current boundaries with the school district

Jorge's Local Picks

Places worth exploring

My personal recommendations — the spots that make this neighborhood feel like home.

🍻
Windermere Brewing Company Restaurant
Craft brewery & kitchen

A community hub with rotating taps and a rotating food truck lineup. The patio on a Friday evening is a scene.

🌅
Staybridge Grille Restaurant
Lakeside dining

Waterfront dining with a relaxed Florida energy. Fresh seafood and good sunsets from the patio.

🌸
The Market at Windermere Shopping
Local grocers

A charming village market with specialty foods, fresh-cut flowers, and the feel of old Florida.

⛳
Caddyshack Bar & Grill Restaurant
Golf-casual

The post-round spot for Windermere's golf community. Good wings, cold beer, and golf on every screen.

🥐
Croissant Gourmet Coffee
French bakery cafe

Fresh-baked croissants, strong espresso, and a quiet corner to read the paper. A proper morning ritual.

🚣
Lakeside Trail (Lake Down) Outdoors
Morning walks & kayaking

The trail circling Lake Down is a community meeting ground — dog walkers, joggers, and families every morning.

Jorge's personal favorites — not sponsored, just genuinely good.

Neighborhood Favorites

Top cafes & parks locals love

Top Cafes
1
The Windermere Café
A charming local spot for espresso drinks, fresh pastries, and a relaxed small-town feel.
2
Foxtail Coffee (Dr. Phillips)
A short drive away, this outpost offers top-tier specialty coffee for Windermere residents.
3
East End Market Coffee Bar
A curated market café with rotating local roasters and artisan food stalls.
Top Parks & Outdoors
1
Windermere Town Dock
A beloved community gathering spot on the Butler Chain of Lakes — kayak launches and sunset views.
2
Summerport Dog Park
Well-maintained off-leash park with shaded areas and a strong community feel.
3
Tibet-Butler Preserve
743 acres of unspoiled wetlands and nature trails right in the heart of Windermere.
Community Guide

What makes this area special

Outdoors
Butler Chain of Lakes

13 connected lakes perfect for boating, wakeboarding, fishing, and sunset cruises.

Golf
Isleworth Golf & Country Club

An elite private club favored by PGA Tour professionals — world-class golf and amenities.

Restaurant
The Rusty Spoon (nearby)

Farm-to-table dining that draws residents in from across the metro.

Nature
Tibet-Butler Preserve

Pristine Florida wilderness with hiking trails right at the edge of the community.

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