Selling a luxury vacation home in Bear’s Den isn’t just about listing a property—it’s about selling a lifestyle. Nestled within Reunion Resort, Bear’s Den is one of Central Florida’s most prestigious gated communities, offering a rare blend of privacy, vacation amenities, and high-end living.
Whether you're moving on from a second home or ready to sell an existing vacation home as an investment, you need a thoughtful strategy to attract serious buyers and close confidently.
I’m Mike Chen, a licensed Realtor® and short-term rental investor specializing in luxury properties across Reunion, Kissimmee, and Orlando.
I help sellers list, market, and sell their vacation homes for top dollar—including the elite estate homes in Bear’s Den. If you’re thinking of selling, here’s what you need to know.
Know What Makes Bear’s Den Buyers Unique
Buyers shopping for a luxury vacation home in Bear’s Den are often:
Affluent families seeking a second home just minutes from Disney World
Golfers drawn to the Jack Nicklaus-designed course that wraps around the community
Investors in the vacation home industry looking for STR-ready estates
Snowbirds or retirees chasing the year-round Florida lifestyle
These buyers are selective. They’re looking for homes that are beautifully designed, well-maintained, and offer top-tier vacation amenities like private pools, home theaters, outdoor kitchens, and access to Reunion’s water park and dining experiences.
Prep and Position Your Home to Shine
To attract the right buyer, you need to highlight the villa’s unique selling points—not just the square footage. Presentation matters, especially in high-end listings. I recently helped a client list a 7-bedroom STR estate in Bear’s Den. With minor touch-ups, professional photography, and smart staging, we sold it in 18 days—bookings included.
Here’s how I help you prepare:
Deep cleaning, touch-up paint, and light landscaping
Professional staging or enhancements to existing STR decor
Ensuring the home is guest-ready and photographically pristine
Capturing lifestyle shots: morning coffee on the balcony, sunset by the pool
Whether your home is owner-occupied or an active short-term rental, I’ll guide you through every prep step so we can list with confidence.
Understand Today’s Market in Bear’s Den
The Bear’s Den section of Reunion Resort is known for its exclusivity and high-end appeal. As of 2025, luxury estate homes for sale at Bear's Den have held strong value thanks to limited inventory, upscale features, and consistent buyer demand. However, with shifts in the broader Florida real estate market, pricing and marketing strategy matter more than ever.
We’ll start with a detailed comparative market analysis, factoring in:
Similar Bears Den homes for sale in recent months
Short-term rental performance data (if applicable)
Community amenities and location premiums
Price it right, and we set the tone for a faster, more profitable sale.
Market the Experience, Not Just the Property
Buyers aren’t just searching for vacation homes for sale in Florida—they’re buying into a dream. That’s why your listing needs to go beyond facts and figures. We focus on:
Luxury photography and drone footage
Video walkthroughs that showcase the flow and experience
3D Matterport tours for remote and international buyers
Emotional storytelling in the listing copy: "Wake up to golf course views, cool off in the private pool, then enjoy dinner steps from the clubhouse."
We also go beyond the MLS with paid social ads, email campaigns, and private outreach to investor networks. When you list with the top Realtor in Orlando, your home gets seen by the right people, in the right places.
Selling a Vacation Home While It’s Rented? No Problem.
Many Bear’s Den homeowners operate their properties as short-term rentals. If that’s you, good news: You can still sell without canceling future bookings or disrupting your guests.
I’ll help manage:
Showing schedules between check-outs and cleanings
Communication with your property manager or co-host
Guidance on how to transfer bookings to the new buyer
Optional inclusion of furnishings and rental assets in the sale
Buyers often prefer homes that come ready to generate income—especially in a top-performing vacation rental market like Reunion.
Negotiate With Strategy, Not Stress
Offers in the luxury market often come with more variables: cash vs. financed buyers, appraisal gaps, furnishings, or closing timelines that depend on bookings. I work with you to break down each offer and negotiate terms that protect your bottom line while keeping the deal moving forward.
Luxury buyers want a smooth process. With the right Realtor, you can sell your home quickly and confidently without sacrificing value.
Selling a Luxury Vacation Home in Bear’s Den
Your Bear’s Den property deserves more than a basic listing—it deserves a strategy built around its strengths, your goals, and the expectations of high-end buyers.
When you work with me, you get:
Local expertise backed by real STR investment experience
Proven systems for listing and selling luxury vacation homes in Bear’s Den
One-on-one support from pricing to prep to closing
Frequently Asked Questions (FAQs)
I’m not just a licensed Realtor—I’m also a short-term rental investor who understands the business side of luxury vacation homes. I know how to price, prep, and market Bear’s Den homes to attract serious buyers, not just tire-kickers. Every listing gets personal attention, professional marketing, and strategy—not just a sign in the yard.
Yes—there’s no pressure or obligation. We’ll start with a free strategy session where I walk you through current market conditions in Bear’s Den, run a home value estimate, and help you weigh the pros and cons of listing now versus waiting. You’ll walk away with clarity either way.
Not necessarily. I help homeowners sell their Bear’s Den vacation homes while they’re still being rented. I coordinate showings between bookings and work with your property manager to keep things seamless. Many buyers prefer homes that come with existing reservations in place.
Every listing gets high-end visuals (HD photos, drone shots, 3D tours), a custom MLS listing, targeted social media campaigns, and private outreach to investor and vacation home buyer networks. I make sure your home stands out and reaches buyers who are ready to act.
Absolutely. Many of my Bear’s Den clients are out-of-state or international homeowners. I handle everything from listing prep to contractor coordination, showings, and negotiations. You’ll stay in the loop without having to fly in or manage anything on-site.
