You can admire colonial-style homes all over New England—but finding one that so convincingly recreates the era’s soul is something else entirely.
Tucked along the Massachusetts line in Stafford Springs, the 10-acre homestead at 49 Upper Road delivers a warming architectural elixir of cinematic charm and everyday livability that makes people stop and ask, “Where has this place been hiding?”
For realtor Wendy Anderson of William Pitt Sotheby’s International Realty, the answer begins with stewardship. “This property has been in the same family for about fifty years,” she says. “They’ve cared for it with so much pride and intention. It’s such a quaint corner of town, really special in its own right.”
From the road, the home immediately evokes a bygone era: a reproduction gambrel colonial built in 1974 by a skilled craftsman who also happened to be the homeowner. His attention to historical accuracy is everywhere—handmade millwork, custom cabinetry fitted with butterfly hinges, wide-plank flooring, and the kind of wood-beam ceilings you usually have to visit a museum to admire. “He built it in a way that honors the old-world charm of the 1600s and 1700s,” Anderson explains. “But he also added all the conveniences of a modern home. It looks like an antique inn. Someone should film a Hallmark movie here.”
The heart of the house is the kitchen, anchored by an enormous vintage hearth once used for both cooking and heating. While the great stove remains as a nod to simpler times, upgraded appliances, granite counters, and a moveable island make the space fully functional for contemporary cooks. Adjacent rooms continue the theme of past-meets-present: a custom-built tavern room that feels like stepping straight into a colonial gathering place, a formal dining room with rich trim details, and a cathedral-ceiling family room framed in post-and-beam construction.
“It has this warm feeling the second you walk in,” Anderson notes. “The woodwork is so beautifully crafted, but the house doesn’t feel old or creaky. You get the magic and character without any of the heaviness people sometimes worry about with antique homes.”
The layout unfolds across 3,400 square feet with five bedrooms and three full baths in the main house. One of the bedrooms is currently used as a sun-splashed office, though the property offers multiple options for anyone who splits time between home and a Boston or Hartford commute. Above the heated barn-garage—fired by a pellet stove and equipped with hot-and-cold running water—sits an expansive office suite with sweeping views of rolling fields, distant hills, and the brook. Alongside the office are two additional bedrooms and a full bath that could easily form an in-law suite, complete with its own entrance.
And that brook? It winds directly through the acreage, contributing to one of the home’s most enchanting sensory details: the sound of moving water everywhere you go. From the stone patio to the fire pit to the swimming pool and pool house, the property feels like an everyday vacation. “The pool overlooks the brook,” Anderson says. “It’s unbelievably peaceful—like being on permanent holiday.”
The heated stone-floor sunroom offers another vantage point, with a built-in hot tub and panoramic views of the land. Beyond the immediate yard lie ten acres of level, usable farmland: space for gardens, animals, or grander visions. “This is a dream property for someone who wants their own homestead,” Anderson says. “Sheep, horses, vegetable beds, it’s suited for so many purposes.”
Anderson hopes the next buyer embraces that spirit of caretaking. “We’d love to see another steward fall in love with the land the way this family did,” she says. “Someone who appreciates the privacy and the country feel, but also loves being so close to everything.”
Stafford Springs itself is a thriving destination, unexpectedly rich with activities and attractions. The town’s famed speedway draws visitors from across New England, while the historic village hosts seasonal festivals, local eateries, and independent coffee shops that give it a lively, close-knit atmosphere. From the property, it’s just minutes to the center of town, a quick drive to I-84, and roughly thirty minutes to Hartford or an hour and a half to Boston. Old Sturbridge Village—one of the region’s premier living-history museums—is also nearby, a fitting neighbor for a home that so lovingly channels early American design.
Yet unlike many historic properties, this home’s comfort level never lags behind its charm. Modern systems and the original builder’s meticulous craftsmanship create a seamless blend of past and present. Whether enjoyed as a gentleman’s or gentlewoman’s farm, a full-time residence, or the foundation for a future inn or hospitality venture, the possibilities feel as broad as the surrounding acres.
“It’s really about the way everything comes together,” Anderson says. “The land, the craftsmanship, the way it sits on the property. It just feels…special.”
And she’s right. Walk the grounds, listen to the brook, step inside the tavern room, or simply look out over the fields from the upstairs office, and the magic is unmistakable. This is a home that invites imagination. A place designed for gatherings, traditions, and the kind of slow-morning, star-filled-evening lifestyle that New England’s rural landscape is famous for.
As the next chapter awaits, Anderson sums up the hope shared by everyone who has loved the property: “We’re looking for someone who wants to be part of its story—someone who sees the beauty, the history, and the enormous potential. It’s not just a home. It’s a whole way of life.”
Info:
Built: 1975
Price: $729,900
Style: Gambrel Colonial
Rooms: 11
Bedrooms: 5
Baths: 3 full
Square footage: 3,400
Acreage: 10
Mill rate: For fiscal year 2024-2025 is 38.59 mills
Best Feature: The life-changing potential. “It’s not just a home. It’s a whole way of life,” Anderson said.
Contact: William Pitt Sotheby’s International Realty
Wendy Anderson: 860-888-0169, [email protected]
Jeff Anderson: 860-604-6226, [email protected]