The Little Bear Island Retreat: Finding the Perfect Remote Executive Getaway on Lake Winnipesaukee

KEY TAKEAWAYS

- Island properties on Lake Winnipesaukee offer unmatched privacy for executive retreats and company gatherings, accessible only by boat

- A successful island property search requires understanding unique lifestyle considerations like docking capacity, seasonal access, and building configurations

- The right lakefront specialist can navigate the complexities of island living to match properties with buyers' specific business and lifestyle goals

WHEN A WATERFRONT HOME ISN'T REMOTE ENOUGH

Some buyers want lakefront. Others want something more. Brie Stephens recently worked with a coaching business owner who had already experienced traditional waterfront living but was searching for something that would truly separate his clients from the outside world. He envisioned a company retreat where his clientele could fully disconnect, and that meant one thing: an island.

"He had owned on the waterfront, but wanted to have more of a company retreat location," Brie explains. The search focused specifically on island properties that could deliver that completely remote experience, where the only way to arrive is by boat or a very long swim.

THE DISCOVERY OF LITTLE BEAR ISLAND

The search led to 36 Little Bear Island in Tuftonboro, a compound that checked every box for the executive retreat vision. Brie Stephens leads Lake Life Realty at Compass, the top-performing lakefront real estate team in New Hampshire's Lakes Region, and she immediately recognized how this property's configuration would serve the buyer's business model.

The main residence was a dormer cape with three bedrooms, multiple baths, kitchen and living room with rustic interior finishes that captured authentic lake character. True to Lakes Region tradition, it featured a three-season screened porch. "You have to have a screen porch at least up here," Brie notes. The front porch and private deck overlooked the water, creating a Tiki hut style hangout space complete with a bar featuring carved timber bears.

DESIGNED FOR GROUP GATHERINGS

What made the property exceptional for retreat purposes was the thoughtful separation of spaces. Beyond the main residence, a dedicated game room building provided enough square footage for a pool table, ping pong table, foosball, and poker table. This rec hall featured vaulted ceilings with wood beams, wood floors, and its own front deck.

The outdoor amenities completed the retreat experience. A volleyball court offered group activities. A U-shaped permanent dock provided the docking capacity essential for bringing multiple clients to the island. Two swim rafts and a sandy perch beach gave guests water access options throughout the day.

Sleeping arrangements were equally well planned. While the main residence accommodated guests comfortably, an additional bunkhouse expanded capacity for larger groups. The property had been nicknamed Little Bear Retreat by previous owners who understood its potential for gatherings.

NAVIGATING ISLAND PROPERTY SPECIFICS

The property's location near the Hole In The Wall added geographic interest. This passage between Devon's Island and Little Bear Island creates a natural landmark that long-time lake users recognize. Lake Life Realty specializes in luxury waterfront properties on Lake Winnipesaukee and throughout the NH Lakes Region, which means understanding these geographic details and what they mean for access and usage patterns.

"There are nuances and specialties to Island Living," Brie explains. "But one and the same makes it very special and unique for certain buyers looking for that really remote lake escape where no one can get to you unless they have a boat."

Island properties require different considerations than mainland waterfront. Seasonal access changes with ice conditions. Supply transport requires planning. Maintenance coordination becomes more complex. Yet for buyers like this coaching business owner, those logistical details are precisely what create value. The barrier to access becomes the feature, not the bug.

WHY THE RIGHT MATCH MATTERS

Finding 36 Little Bear Island required understanding both the island property inventory and the specific business application the buyer had in mind. Brie Stephens was named to NAR's 30 Under 30 and has closed over $128 million in lakefront property sales, an experience that allows her to quickly assess whether a property's configuration will support a buyer's vision.

For this buyer, the compound layout meant he could host multi-day retreats where clients stayed on site, gathered in dedicated entertainment spaces, and experienced complete separation from their daily routines. The island setting wasn't just about views. It was about creating an environment where transformation could happen without distraction.

"It really was just this retreat that you could have," Brie says. Some properties sell themselves on square footage or finishes. Island properties sell themselves on what they make possible.

FREQUENTLY ASKED QUESTIONS

What are the main challenges of owning an island property on Lake Winnipesaukee?

Island ownership requires planning around boat access for all supplies, maintenance, and guests. Seasonal considerations include winter ice conditions that can limit access, coordinating contractors who must transport tools and materials by water, and managing utilities that may require different infrastructure than mainland properties. The reward is complete privacy and a truly unique lake experience.

How much docking capacity do you need for an executive retreat property?

For company retreat purposes, you want permanent docking that can accommodate multiple boats simultaneously so guests can arrive within the same time window. A U-shaped dock configuration works well because it provides protected sides and can handle various boat sizes. You also want to consider guest docking when clients arrive in their own watercraft, versus being transported by the owner.

Are island properties on Lake Winnipesaukee good investments for business use?

Island properties that function as executive retreats offer tax advantages when used for legitimate business purposes like client meetings and company gatherings. The unique setting often makes these retreats more memorable and effective than traditional conference settings. Resale value remains strong because the limited inventory of island properties means demand consistently exceeds supply in the Lakes Region market.