Luxury home with pool in Windermere Florida

Luxury Homes with Pool in Windermere

Resort-style pools, screened lanais, and outdoor living at its finest — browse Windermere luxury pool homes.

$1.2M
Median w/ Pool
3
Top Communities
30+
Years Local
Year-Round
Pool Season

Searching for a luxury pool home in Windermere?

Micaela knows every community and can find the perfect pool home for your lifestyle.

Free consultation. No obligation. Local expert.

As a local Orlando realtor with over 34 years in Central Florida, if you're looking for a luxury pool home in Central Florida, Windermere is where it's at. The larger lots, mature tree canopy, gated communities, and year-round warm weather create the perfect setting for that resort-style backyard experience. I've shown pool homes across this area for years, and the outdoor living here is genuinely impressive.

Top Communities for Luxury Pool Homes

Isleworth is Windermere's premier ultra-luxury enclave. This guard-gated community on the Butler Chain of Lakes features custom estates with infinity pools, outdoor kitchens, spa systems, and private lake access. Homes in Isleworth routinely exceed $2 million and offer some of the most impressive outdoor living spaces in Central Florida.

Keene's Pointe is a guard-gated community on Lake Tibet Butler where most homes include custom pools with views of the lake, conservation, or golf course. Pool homes here typically range from the $800,000s to over $2 million, with newer builds featuring modern vanishing-edge designs and summer kitchens.

Lake Butler Sound and the broader Lake Butler area offer a quieter alternative with lakefront properties that blend old Florida charm with luxury outdoor living. Many homes feature heated pools, screened enclosures, and direct lake access for boating and fishing.

What Buyers Can Expect

Luxury pool homes in Windermere typically start in the high $600,000s for newer communities and can exceed $5 million for lakefront estates in Isleworth. Most homes in this category include screened pool enclosures (standard in Florida for bug protection), summer kitchens, covered lanais, and in many cases, spa or hot tub features.

Lot sizes in Windermere are generally larger than the Orlando metro average, which gives builders more room for elaborate pool designs including freeform pools, lap pools, water features, and resort-style landscaping. HOA rules vary by community. some allow custom pool designs while others have architectural guidelines.

Why Windermere for Pool Living

Florida's climate makes pool ownership a true year-round lifestyle, and Windermere's generous lots attract buyers who want more than a basic rectangle. You're close to Disney, Dr. Phillips dining, and top-rated schools while enjoying the privacy and space that serious outdoor living demands.

Luxury pool home backyard in Windermere

Pool homes in Windermere take outdoor living to another level. Resort style pools, summer kitchens, covered pavilions, and lush landscaping create backyard environments that feel like private retreats in one of Orlando's most desirable communities.

Windermere lakefront home with pool

Many Windermere luxury homes combine lakefront living with private pool amenities. The result is an outdoor experience that blends natural waterfront beauty with the comfort and convenience of a resort style backyard.

Luxury pool home listed by M2M Realty

M2M Realty represents some of the finest pool homes in Windermere and across Central Florida. From custom builds with infinity pools to established estates with resort style outdoor spaces, we help buyers find properties that match their vision.

Work With Micaela Navarra

Micaela Navarra — Orlando Realtor, M2M Realty

Outdoor living is a huge part of the Windermere lifestyle. I help buyers find homes with the right pool setup — resort-style, lap pools, infinity edges, screened lanais, summer kitchens — matched to their lifestyle and budget.

Languages: English, Italian, Spanish, and Portuguese

Call or text: 407.761.5501  |  Email: Mnavarrarealty@gmail.com

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Frequently Asked Questions

Do most Windermere luxury homes have pools? +

The majority of Windermere luxury homes have pools or room to add one. In gated communities like Isleworth, Keenes Pointe, and Lake Butler Sound, pools are standard on most premium properties. Many feature resort-style designs with spas, waterfalls, and summer kitchens.

What do Windermere pool homes cost? +

Windermere pool homes range from $500,000 for non-gated homes with pools to over $10 million for Isleworth lakefront estates with resort-style outdoor living. The pool itself adds $50,000 to $200,000 in value depending on design.

What should I look for in a Windermere pool home? +

Check the pool's age and condition, screen enclosure integrity, equipment age, heating system, decking material, and whether the lanai has a summer kitchen. Also consider lot orientation for sun exposure and privacy from neighbors.

Can I add a pool to a Windermere home? +

Yes, if the lot size allows and HOA permits it. Pool construction in Central Florida typically costs $50,000 to $150,000 depending on design. Check HOA rules for any restrictions on pool type, size, or screen enclosure requirements.

Do pools add value in Windermere? +

Yes. In the Windermere luxury market, a well-maintained pool with modern design adds significant value. Buyers expect outdoor living at this price point, so homes without pools can be harder to sell.

What is a screened lanai? +

A screened lanai is a covered outdoor living area enclosed by screen panels. It keeps out insects while allowing airflow and outdoor enjoyment. In Florida, screened pools and lanais are standard features that add significant livability and value.

What Clients Say
★★★★★

"Our pool in Windermere is where our family lives. Micaela found us a home with a resort-style pool and a preserve view that feels like a permanent vacation."

The Lawson Family
Bought Pool Home in Windermere

Ready to Find Your Pool Home?

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Published June 4, 2026 by Micaela Navarra, Orlando Realtor with M2M Realty, a boutique brokerage delivering personal attention across Central Florida. Speaks English, Spanish, Italian, and Portuguese. Call 407.761.5501.