Perched above Lake Winnipesaukee with sweeping lake & mountain views, 290 Trask Side Road presents a compelling opportunity to own a turnkey four-season retreat in NH's Lakes Region — blending lifestyle, long-term value & strong luxury rental appeal. Ideally positioned near Wolfeboro — widely regarded as America's oldest summer resort town — this modern farmhouse offers the rare ability to enjoy the best of NH in every season, from boating & lakeside dining in summer to skiing, snowmobiling & mountain escapes in winter. Located in low-tax Alton Bay, the property appeals to buyers seeking a second-home investment, 1031 exchange, or flexible ownership asset with luxury rental potential. Its proximity to Lake Winnipesaukee, Gunstock Mountain Resort, Wolfeboro & the White Mountains corridor positions it well for year-round demand among discerning renters seeking elevated accommodations with iconic NH character. Set on a private wooded lot with mature trees, stone outcroppings & terraced landscaping, this impeccably built farmhouse balances refined aesthetics with effortless livability. A covered composite porch with tongue-&-groove ceiling, ceiling fans & stone-faced gas fireplace serves as true four-season living — perfect for autumn evenings, summer entertaining, or winter weekends après-ski. Additional features include a hot-tub, fire pit, detached workshop/garage & standing-seam metal roof. Inside, the chef's kitchen anchors the open-concept main level with a large island, quartz countertops, custom shaker cabinetry & stainless appliances. Hardwood floors, crown molding & black-framed windows throughout. The primary suite, offers custom built-ins & a full wall of lake-facing windows. Above the detached barn, a finished rec & guest space with knotty-pine paneling, & gas fireplace adds flexibility for entertaining or added rental income. Whether a luxury rental, or legacy NH retreat — 290 Trask Side Road captures everything that draws generations to the Lakes Region.

Listing courtesy of Adam Dow of KW Coastal and Lakes & Mountains Realty/Wolfeboro Phone: 866-525-3946



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Last checked: 2026-05-16 05:16 PM UTC