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Architectural illustration of a Florida luxury home's shaded lanai, pool and palm-lined landscaping.

Reunion Resort, Kissimmee

Bears Den homes for sale: 5-bedroom homes

Bears Den homes for sale, focused on exactly five-bedroom single-family homes. We'll help you weigh the layout, shared spaces and outdoor living that suit your everyday life or second-home plans.

5-bedroom homes for sale in Bears Den

1 listing

Browse Bears Den 5-bedroom homes by price

For 5-bedroom homes for sale in Bears Den, start with the asking-price range that fits your plans: 5-bedroom homes under $2M in Bears Den, 5-bedroom homes from $2M to under $2.5M in Bears Den, or 5-bedroom homes from $2.5M in Bears Den. Each search retains exactly five bedrooms, single-family residences and the same Bears Den boundary. Some ranges may have no matching properties; use the live results to see what is available rather than treating these bands as typical community prices.

Five bedrooms, with room to live well

Compare five-bedroom homes around the spaces you would use every day, as well as the number of sleeping rooms. Map bedrooms and bathrooms by floor, then consider how the arrangement would work for your household and visiting family. Check laundry placement, storage and the separation between quiet rooms and recreation areas. Where balconies, covered seating, pools or outdoor kitchens are present, assess how they connect with indoor living areas and what their upkeep involves. A viewing should help you answer practical questions about where you would sleep, gather and retreat, without assuming every five-bedroom home shares the same features.

What makes a five-bedroom plan work for you?

Judge each plan on usable space. Bedroom count alone does not establish footprint, efficiency or upkeep savings.

  • Sleeping arrangements that suit you

    Check bedroom separation and whether a main-level suite suits your routines. Consider privacy from gathering spaces, not just which floor a room occupies.

  • Practical circulation and storage

    Trace routes between bedrooms, laundry and living areas. Assess storage where you need it and how comfortably you can move through furnished rooms.

  • Shared space before extra bedrooms

    Compare lounges, dining areas and outdoor living with houses offering more bedrooms. Decide whether extra sleeping rooms would add value to your daily use.

The Bears Den setting, beyond your front door

Bears Den homes for sale place you within Reunion Resort in Kissimmee, with recreation to consider alongside the home itself. Golden Bear Park includes a dog park, shaded gazebos, a playground and a practice putting green, offering settings for time outdoors and informal gatherings. Reunion's wider facilities are distinct: three golf courses designed by Arnold Palmer, Tom Watson and Jack Nicklaus, a water park, tennis, pickleball and on-site dining. Traditions restaurant is at the Nicklaus Clubhouse. As you picture your routines, separate the amenities you would use regularly from occasional interests, then confirm the access attached to a purchase. Our Bears Den community overview puts the neighborhood in broader context.

Separate ownership costs from Club access

Association assessments, CDD assessments and Club charges are separate considerations when you compare ownership costs. Owning a property does not itself establish Club membership or your eligibility to join, so confirm the home's membership status and the requirements that would apply to your purchase. Our Reunion HOA and assessment information explains the cost categories, while our Reunion Club membership information addresses recreation access. We can help you identify the questions to raise about a particular home, keeping recurring ownership obligations separate from the facilities you hope to enjoy.

Bears Den-wide inventory and asking prices

These figures cover all bedroom counts within Bears Den, not just the five-bedroom homes featured above.

For sale now
7
Median asking price
$2,200,000

Nearby sales

48 properties sold within half a mile in the last 12 months · median $1,045,000

Questions about five-bedroom homes in Bears Den

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Talk to Gaby before you buy

I can arrange viewings, answer your questions and prepare a personalized rental projection for any home you're considering.

Find the five-bedroom home that fits your plans

Start with exactly five-bedroom homes in Bears Den, then look closely at the details that will shape your time there: bedroom placement, outdoor outlooks and the rooms you will use most. We can help you frame questions about individual layouts, ownership costs and Club access, keeping your personal priorities at the center of your search for an everyday residence or second home.

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