Maitland holiday home buying

Holiday Gatherings in Maitland: The 3 Questions Everyone Asks About Real Estate

December 20, 20252 min read

Every holiday season, whether I’m at a neighborhood gathering in Maitland, a family dinner in Winter Springs, or sipping hot cocoa at Lake Lily Park, I hear the same real estate questions. And honestly — they’re great questions. If you’ve been thinking about buying or moving in 2025, especially here in Maitland, you’re not alone.

Let’s dig into the three I hear the most… and what they mean for you.


1. “Will I be able to find a home if I want to move?”

Short answer: YES — and inventory in Maitland is finally growing.

For the last couple of years, buyers felt like homes were disappearing faster than holiday desserts. But in 2025, we’re seeing:

  • More new listings

  • Longer days on market

  • Sellers becoming more flexible

  • More “move-up” sellers entering the market

In Maitland, the sweet spot is move-in-ready homes under $700K, and those are returning. If you’re open to nearby communities like Winter Springs, Oviedo, or Winter Park, your options instantly double.

2. “Should I wait for prices to come down?”

This is the most common question — and also the trickiest.

Here’s the truth:
Maitland is one of the most stable, high-demand pockets in Central Florida. Prices rarely “drop,” they simply level off.

Buyers who waited in 2021 regretted it.
Buyers who waited in 2023 regretted it.
Buyers who waited in 2024 watched prices rise again.

If you’re waiting for a “crash,” Maitland likely won’t be the place where it happens.

Instead, think about this:
✔ Is the home right for you?
✔ Can it support your lifestyle for the next 5–7 years?
✔ Does it keep you close to the people + places you love?

If those answers are yes, the best time to buy is when the right home becomes available — not when the “perfect” market shows up.


3. “Will I ever be able to afford a house?”

YES — but affordability looks different for every person.

Today’s Maitland buyers are getting creative and strategic:

  • Expanding search radius to Oviedo, Casselberry, Winter Springs

  • Using down-payment programs

  • Choosing homes that need light cosmetic updates

  • Planning 2026 purchases now

  • Taking advantage of more negotiation power

The biggest difference? You don’t need to guess anymore.
I can help you run a simple, personalized affordability plan, no pressure, no mortgage talk required — so you confidently know your path.


✨ Ready to Explore Maitland Homes? Start Here.

Before homes pick up in January, get ahead of the competition.
👉 Visit my landing page: : https://allisondayhomes.com/neighborhoods/maitland


Allison Day

Local Real Estate expert serving the Greater Orlando area since 2005!

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