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Thu, December 25, 2025
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Christmas House-Sitting Romance in Greenfield
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Published in House and Home on Thursday, December 25th 2025 at 6:28 GMT by CNN- 🞛 This publication is a summary or evaluation of another publication
- 🞛 This publication contains editorial commentary or bias from the source
A Christmas House‑Sitting Romance: How a Chance Encounter Turns into Holiday Magic
When the holiday season is a time for family gatherings, holiday lights, and the scent of pine and cinnamon, the idea of being a house‑sitter seems like an unlikely setting for romance. Yet a heart‑warming story that first appeared on CNN’s “Travel” section in December shows how a fortuitous meeting in a snowy Midwestern town can transform a simple housesitting job into a budding love story that feels as cozy as a crackling fireplace.
The article, “Christmas housesitter romance: chance encounters,” follows 28‑year‑old freelance writer Maya Evans, who accepted a short‑term house‑sitting position with a couple living in a historic Victorian home in the small town of Greenfield, Wisconsin. The Evans house, a three‑story, clapboard‑covered cottage that appears straight out of a holiday postcard, was to be vacant for a month while the owners, retired schoolteacher Linda and former engineer Tom, traveled to visit family in Florida. They requested a trustworthy caretaker to tend to the dog, keep the house warm, and deliver mail.
Maya, who had recently finished a book deal, was looking for a quiet place to write. The opportunity was a perfect fit—especially since the house’s sprawling gardens and tasteful décor seemed like a “winter wonderland in the middle of the year.” She signed a lease‑back contract, paid a modest fee, and arrived on a chilly December morning, just as the first snow began to dust the town’s rooftops.
What started as a purely logistical arrangement quickly became an emotional journey. Linda and Tom, both in their early sixties, welcomed Maya with a pot of cocoa and homemade gingerbread cookies. Their home was a shrine to holiday traditions: a hand‑carved “Merry Christmas” sign hung above the fireplace, a string of twinkling lights curled around the banister, and a Christmas tree—bare, waiting for ornaments—stood proudly in the living room. Maya’s role expanded beyond house‑sitting; she soon found herself organizing the family’s holiday playlist, arranging the centerpiece of the Christmas Eve dinner, and even helping Tom, who had never been a “tinsel enthusiast,” to hang ornaments on the tree.
The article highlights a pivotal moment on the evening of Christmas Eve: a snowstorm rattles the windows, and Linda’s 10‑year‑old grandson, Milo, sits beside Maya, giggling as they practice the “Jingle Bells” dance routine they’d choreographed earlier that week. Maya is visibly touched by the familial warmth radiating from the home. She realizes that she has become more than a caretaker; she is part of a community that she will never forget.
A key element of the piece is its exploration of housesitting as a cultural practice. CNN readers are directed to a sidebar about “The Growing Trend of House‑Sitting,” which links to the HouseSitter.com website, detailing how people worldwide use the service to travel, write, or simply escape the monotony of their day jobs. It also includes a brief interview with a seasoned housesitter, who notes that “the joy of stepping into someone else’s space, respecting their boundaries, and creating memories—especially around the holidays—creates a unique bond that often feels like a second family.”
Another link in the article guides readers to the Greenfield Historical Society’s website, where the Victorian house is listed as a historic landmark. The society’s page provides background on the house’s original owner, a 19th‑century philanthropist, and explains the architectural details that have made it a favorite for holiday photography in the region. This additional context underscores why the house itself becomes almost a character in the story, framing the romance that blossoms around it.
As the month ends, Maya faces the decision of whether to return to her life in New York or stay in Greenfield. The article chronicles her thoughtful deliberation, citing a conversation with Linda: “Sometimes the best stories happen in the most unexpected places,” she says. Maya ultimately chooses to take a job as a copy editor in Greenfield, which, according to the article, is “the first time she’s let the house‑sitting romance become more than a winter interlude.”
The story concludes with a tender moment on a quiet morning in early January. Maya, still wearing the sweater Linda knitted for her, sits beside Tom and Milo by the fireplace, sipping hot chocolate as the crackling fire illuminates the room. She realizes that she has found a new home and a new family, one that will grow with each holiday season.
“Christmas housesitter romance: chance encounters” serves as both a celebration of holiday traditions and a reminder that love often finds us in the most unexpected places. By weaving together the charm of a historic home, the warmth of a small town, and the genuine connections formed during a brief stay, CNN turns a simple housesitting tale into a story that feels like a holiday movie—except this one is real, and it’s happening in a place where the snow is falling just in time for the next chapter.
Read the Full CNN Article at:
[ https://www.cnn.com/travel/christmas-housesitter-romance-chance-encounters ]
