$2,100,000
Under contractAbout this home
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.
Property details
- MLS
- Prime MLS
- MLS #
- 5088851
- Property type
- Single Family Residence
- Subdivision
- N/A
- Status
- Under contract
- Days on market
- 42
- On market date
- N/A
- Stories
- N/A
- Total bathrooms
- 2
- Garage spaces
- 3
- Parking spaces
- N/A
- Lot size
- 0.92 acres
Location
Get directions →Nearby schools
Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.
- Enrollment
- 407
- Student:teacher ratio
- 9.5:1
- District
- Alton School District
- Enrollment
- 375
- Student:teacher ratio
- 10.4:1
- District
- Governor Wentworth Reg School District
- Enrollment
- 728
- Student:teacher ratio
- 11.6:1
- District
- Governor Wentworth Reg School District
Walkability
Blended score for Alton's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).
Market position
How this listing compares to current activity in Alton, from live MLS data.
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Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 06/26/26.