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How to Buy a Second Home in Windermere

Toni Marie Cafferty  |  October 7, 2026

How to Buy a Second Home in Windermere

By Toni Marie Cafferty

Buying a second home in Windermere is a dream for many, and it is easy to see why. With its beautiful lakefront estates, exclusive communities, and enviable proximity to Orlando, this is one of Central Florida's most desirable places to own a getaway. That said, purchasing a second home involves some different considerations than buying a primary residence. Knowing what to expect helps you move forward with confidence. Here is my guide to how to buy a second home in Windermere.

Key Takeaways

  • Defining your goals shapes the entire buying process.
  • Financing a second home differs from a primary residence.
  • Choosing the right community is essential to your enjoyment.
  • Understanding the full costs protects your investment.

Define Your Goals for the Home

Before you begin your search, it is important to be clear about what you want from a second home. Your goals will guide everything from the location to the type of property. I always start here with my clients to ensure we find the perfect fit.

Questions I Ask First

When I help buyers define their vision, I work through questions like these:

  • Will this be a vacation retreat, an investment, or a future residence
  • How often do you plan to use the home
  • Are you interested in renting it out when you are away
  • What lifestyle and amenities matter most to you

Understand Financing a Second Home

Financing a second home is a bit different from financing a primary residence, and it is important to understand those differences early. Lenders often have distinct requirements for second homes, so preparation is key. I help my buyers approach this step with clarity.

What to Know About Financing

When I guide buyers through financing, I point to these considerations:

  • Second homes often require a larger down payment
  • Lender requirements can differ from a primary residence
  • Getting pre-approved clarifies your true budget
  • Working with a lender experienced in second homes is valuable

Choose the Right Community

Windermere offers a range of beautiful communities, each with its own character and appeal. Selecting the right one is essential to enjoying your second home to the fullest. I help my clients find the setting that fits their vision.

Communities Worth Exploring

When I introduce buyers to Windermere, I highlight what the area offers:

  • Stunning lakefront homes along the Butler Chain of Lakes
  • Exclusive gated communities like Isleworth and Keene's Pointe
  • Beautiful settings close to Orlando and its attractions
  • A range of luxurious options to suit different lifestyles

Factor in the Full Costs

A second home comes with ongoing costs beyond the purchase price, and understanding them is essential. From taxes to insurance to community fees, a complete picture helps you budget wisely. I make sure my buyers know exactly what to expect.

Costs to Anticipate

Before buying, I help clients account for the full range of expenses:

  • Property taxes on the second home
  • Homeowners insurance, which can be significant in Florida
  • Community association fees where applicable
  • Ongoing maintenance and upkeep, especially when away

Frequently Asked Questions

Is it harder to finance a second home than a primary residence?

Financing a second home often involves different requirements, such as a larger down payment. It is very manageable with the right preparation, and I help my buyers connect with lenders experienced in second-home purchases to make the process smooth.

Can we rent out our second home in Windermere when we are not using it?

Many owners do, though it depends on the community and its rules. I help buyers understand any restrictions and consider whether renting fits their goals, so they can make an informed decision before purchasing.

What makes Windermere a good place for a second home?

Windermere offers beautiful lakefront living, exclusive communities, and easy access to Orlando and its attractions. It is a wonderful blend of tranquility and convenience, which makes it a favorite for those seeking a Central Florida getaway.

Reach Out to Toni Marie Cafferty Today

Buying a second home is an exciting step, and having a knowledgeable local guide makes all the difference. Helping clients navigate the process and find a getaway that fits their vision is one of the most rewarding parts of my work, and I know Windermere intimately.

Please keep in mind that I am a real estate professional rather than a lender or financial advisor, so I always encourage buyers to seek qualified guidance on financing specifics. When you are ready to explore a second home in Windermere, reach out to me at Toni Marie Cafferty. I would be glad to walk you through every step and help you find the perfect place to call your own.


Toni Marie Cafferty

Toni Marie Cafferty

About the Author

A true native, Toni Marie Cafferty calls Florida home. Originally from Jacksonville, she moved to Central Florida while attending the private university of Stetson where she graduated with a degree in Marketing and International Business. With time spent in Austria, Germany, Italy, Switzerland, and the Netherlands, she loves to explore other cultures. In her real estate career, she’s had the pleasure to work with buyers from around the world.

As a Realtors® daughter, Toni Marie was raised in the real estate industry and contributes her high level of client care to that of her mother. Toni Marie caters to the luxury market with a white glove-style all her own. Just as the Golden Rule states, “Do unto others as you would have them do unto you,” Toni Marie takes this to the next level offering superb client care. When asked, she says “it’s all about the details and being present with those you are working with whether it be in-person or over the phone. Be ahead of your client’s questions and help provide clarity and honest feedback.”

Toni Marie Cafferty’s Gold Standard (#tmcgoldstandard) has garnered respect from her colleagues and clients alike as she grows her real estate profession. In the past 9 years, she has managed over $106 million in sales and she’s not slowing down; rather she is expanding her reach with Compass to help more buyers find their place and continue to shatter records for her sellers. Most recently, Toni Marie has been the highest priced estate under contract in Windermere, Florida since 2019 and set a new price per square foot high in the exclusive community of Isleworth Golf & Country Club.

Toni Marie rounds out her career with a balance of time spent with her friends and family. Her husband, Brett, and their two dogs are looking forward to growing their family over the next few years as they continue to call Central Florida their home.

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