Split photo: whimsical treehouse + hobbit door in hillside.

Living in a Treehouse or Hobbit Hole: What Quirky Homes Teach About Real Estate

October 02, 20251 min read

Earth-sheltered hobbit-style house with stone walls, grassy roof, and garden surrounded by trees in a lush green landscape.

Every so often, a real estate story pops up that reminds us: homes aren’t just about square footage or granite counters—they’re about imagination. This fall, quirky “fairy-tale” listings have been making headlines, from treehouses built high in the Carolina pines to hobbit-style homes in Oregon that look like they rolled straight out of Tolkien.

Honestly, checking out these homes is fascinating as most are a labor of love.

Closer to home, New England has its share of whimsical getaways. In New Hampshire’s White Mountains, you can book a night in an actual treehouse with spiral staircases and rope bridges. Over in Vermont, a hobbit-inspired rental carved into a hillside lets visitors “live like Frodo” (without the orcs). Even in Rhode Island, a few Airbnb hosts have gotten creative with yurts and cabins styled after fantasy escapes.

Why do these oddball homes matter? Because they showcase the emotional side of real estate. People don’t remember square footage; they remember stories. A family getaway in a treehouse, a honeymoon in a hobbit hole—these experiences stick. And that’s a lesson for sellers, too: if you can make your home feel unique and memorable, it will stand out in buyers’ minds long after they’ve scrolled past dozens of cookie-cutter listings.

So while you may not be installing a round hobbit door on your colonial, you can take a page from these fantasy homes. Highlight the quirks. Stage around the story your house tells. Because in a crowded market, being memorable is often more powerful than being perfect.

References

Ryan Cook, CRS • CRB • CPS • C2EX • CLHMS • SRS • RENE, is the Broker/Owner of HomeSmart First Class Realty, leading a growing team serving Greater Boston and Providence. Licensed in MA & RI—a former engineer, Ryan is also a licensed contractor and insurance agent. He has sold full-time since 2009. He blends boots-on-the-ground construction experience with data-driven negotiation to help clients buy, sell, invest, and navigate complex deals (including an expertise in probate real estate). A U.S. Coast Guard veteran and ZBA chair, he calls Easton, MA home.

Ryan Cook

Ryan Cook, CRS • CRB • CPS • C2EX • CLHMS • SRS • RENE, is the Broker/Owner of HomeSmart First Class Realty, leading a growing team serving Greater Boston and Providence. Licensed in MA & RI—a former engineer, Ryan is also a licensed contractor and insurance agent. He has sold full-time since 2009. He blends boots-on-the-ground construction experience with data-driven negotiation to help clients buy, sell, invest, and navigate complex deals (including an expertise in probate real estate). A U.S. Coast Guard veteran and ZBA chair, he calls Easton, MA home.

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