Wolfeboro, NH

21 Trask Mountain Road

$875,000

MLS# 5099338 · Single Family Residence

1 day on market
The Listing

A 4-bedroom 1820s home in Wolfeboro on 14 acres.

4
Bedrooms
2
Baths
2,634
Sq Ft
14
Acres

Description

This c1820 4Bdrm/2Bath Ctr Chimney Federal on 14 Acres (half each: Pasture & Woodlot) abuts an 87-Acre Conservation lot in an area of other late 18th and early-to-mid 19th century homes. Built for Dr. Thomas J. Tebbetts (N Wolfeboro's earliest physician) this home was possibly started a few years earlier as his grandfather Jonathan (who fought FOR the British in the "French & Indian" wars and AGAINST the Brits in the Revolution!) owned the land from 1807 (& their descendents stayed until 1914!) The current owners' Grandparents purchased this home in 1928, with its attached 50x20 Woodshed (w/the original "bathroom"). Now with the c1985 24x30 2 story Barn & 24x30 2-car Garage, there are multiple work & storage spaces. This convenient location is minutes from Hannafords, Walgreens, Tractor Supply, Dunkin, etc. at the intersection of Rtes 28 & 16 and an easy 1-hour commute N to the WHITE MOUNTAINS or S to the SEACOAST. Meanwhile it's <15 minutes to Wolfeboro's Historic Lakeside Downtown w/Town Beaches on Lakes Wentworth & Winnipesaukee, Shopping, Restaurants, updated Public Library & Public Safety complex, as well as our upgraded (& award-winning) Huggins Hospital. Families will also enjoy "The Nick" Recreation Park, the multi-use Cotton Valley Rail Trail (that runs from the Big Lake 12 miles East to Wakefield) and the 5 well-regarded K-12 Governor Wentworth/Kingswood Schools, (including the Lakes Region Tech Center). While ready for immediate occupancy, most folks will probably want to upgrade the Kitchen sooner rather than later. However both bathrooms, new rooms on the 3rd floor & the 4-Bedroom Septic System were all completed in last couple of decades. If you are looking for a quality Wolfeboro home with attached out-buildings, a large yard (including a 14x10 Sap House & a 20x12 "3-sided run-in" for the horse/s) and space for Gardening and/or family Farming with an attached Woodlot, this stonewall-bounded property may be for you. See Floor PLANS in Documents.

Features

Interior

Fireplace Screens/Equip
3+ Fireplaces
Hearth
Skylight
Walkup Attic

Exterior

Barn
Garden
Outbuilding
Enclosed Porch
Screened Porch
Shed
Window Screens
Storm Window(s)

Heating

Multi Fuel
Oil
Baseboard
Hot Water
Zoned
Wood/Oil Combo Furnace

Cooling

None

Parking

Storage Above
Garage
Parking Spaces 6+
Unpaved
Barn
Attached

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Financial

Annual Taxes
$5,948

Location

Residential · NH-Carroll County · Listed Jul 10, 2026

About Wolfeboro, NH

Known as "The Oldest Summer Resort in America," Wolfeboro sits at the eastern shore of Lake Winnipesaukee. Its walkable downtown features independent shops, restaurants, and the New Hampshire Boat Museum. Year-round residents enjoy excellent schools, a vibrant arts scene, and easy access to multiple lakes.

Walkable downtown with shops & dining
New Hampshire Boat Museum
Cotton Valley Trail (12-mile rail trail)
Brewster Academy (private school)
Access to Winnipesaukee, Wentworth & Crescent lakes
Wright Museum of WWII
County: Carroll
Population: ~6,300
Schools: Governor Wentworth Regional (SAU 49)

Distances are approximate. Click any destination for driving directions. NH has no state income tax or sales tax.

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Closed sales in the past 12 months. Data from PrimeMLS.

$875,000

Active Listing

Bedrooms4
Bathrooms2
Sq Ft2,634
$/Sq Ft$332
Vacation Rentals

Experience the Area First

Rent a lakefront property nearby for a week or more

Listing courtesy of K A Perry Real Estate, LLC · Ken Perry · 603-569-1563
PrimeMLS

IDX display courtesy of Yankee Pedlar Realtors, Wolfeboro NH.

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