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The highest-performing listings in Greenwood.
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Very Investor friendly
Short-term rentals appear permitted citywide without a dedicated STR permit, relying on standard zoning and building compliance; the town’s tone is supportive and compliance is a known, manageable process with no caps or heavy restrictions.
Local STR Agent
STR specialist · Greenwood, ME
Greenwood is a small rural town in Oxford County in western Maine, with a population of approximately 800 residents. Tucked into the foothills on the eastern slopes of the White Mountains, it has the quiet, traditional character of a New England mountain town, surrounded by forests, ponds, and ridgelines. The community is best known as a gateway to some of western Maine's most popular outdoor destinations, particularly the Sunday River ski resort area, and it sits roughly 80 miles northwest of Portland, the nearest major city.
Mount Abram is a small, family-friendly ski area located within the town of Greenwood itself, just minutes from most points in town. With a relaxed atmosphere, affordable lift tickets, and a community-oriented feel, it appeals to skiers and snowboarders who prefer a less crowded alternative to Maine's larger resorts. During the warmer months, the mountain operates as a mountain biking and outdoor recreation destination.
Sunday River in neighboring Newry is one of the largest ski resorts in New England, with eight interconnected peaks, extensive terrain for all skill levels, and a long winter season. About a 15- to 20-minute drive from Greenwood, the resort offers lodging, dining, and a full calendar of events, and in summer it hosts weddings, mountain biking, and zipline tours. The resort's scale and reputation make it the primary draw for visitors staying throughout the region.
The nearby town of Bethel, roughly 15 minutes from Greenwood, is a classic New England village with a walkable downtown of shops, restaurants, and historic inns. It serves as a hub for visitors exploring western Maine and is home to the Maine Mineral & Gem Museum, which features one of the largest collections of meteorites in the world. From Bethel, travelers can also access Grafton Notch State Park, known for dramatic waterfalls including Screw Auger Falls and remote stretches of the Appalachian Trail.
Greenwood is a compelling base for short-term rentals because it offers a quieter, more affordable alternative to staying directly at the major ski resorts, while remaining within easy reach of Sunday River, Bethel, and the surrounding mountain landscape. The combination of small-town charm, year-round outdoor recreation, and proximity to established visitor draws makes it well suited for owners looking to serve skiers in winter, leaf-peepers in autumn, and hikers, bikers, and paddlers throughout the warmer months.