Courtesy Of Margot Skelley Of Compass New England, Llc
14 & 20 Gateway Rd Wolfeboro, NH 03894
14 & 20 Gateway Rd Wolfeboro, NH 03894 | MLS 5108354 Photo 1
14 & 20 Gateway Rd Wolfeboro, NH 03894 | MLS 5108354 Photo 2
14 & 20 Gateway Rd Wolfeboro, NH 03894 | MLS 5108354 Photo 3
14 & 20 Gateway Rd Wolfeboro, NH 03894 | MLS 5108354 Photo 4
14 & 20 Gateway Rd Wolfeboro, NH 03894 | MLS 5108354 Photo 5
For more information on this listing, contact us at: (603) 293-7227
Active
$13,900,000

14 & 20 Gateway Rd Wolfeboro, NH 03894

Single Family Property Type
9 Beds
8 Full 3 Half Baths
9,295 Sq. Ft.
2022 Year Built
Carroll County
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There is nothing like this on Lake Winnipesaukee. Offered together as a private Winter Harbor compound, 14 & 20 Gateway Road encompass approximately 3 acres +/- with approximately 370' +/- of combined waterfront, two residences, extensive docking, and a sandy walk-in beach. The centerpiece, completed in 2023, is an approximately 8,600-square-foot contemporary residence was engineered by Thornton Tomasetti. Brazilian black slate and engineered rift oak floors, solid rift oak interior doors, hand-selected natural quartzite, custom millwork, stained red cedar siding, Douglas fir porch ceilings, and IPE decking define the build. A fully integrated Control4 system governs lighting, climate, Lutron power shades, and distributed audio. An 800-amp electrical service is supported by 45 kW generator backup. Six bedrooms, six full baths, three half baths, generous gathering spaces, and multiple professional-grade kitchen and prep stations support serious entertaining. At 20 Gateway, a cantilevered steel boathouse with rooftop entertaining deck is paired with a no-profile boat lift, 50-foot aluminum Lift-A-Dock, and sandy walk-in beach. At 14 Gateway, 195 feet of Winter Harbor frontage includes expansive U-shaped covered docking with room for multiple boats and watercraft. The classic 1958 Winnipesaukee cabin at 14 Gateway sits on approximately two additional acres and offers three bedrooms, one full bath, warm wood interiors, and a broad lakeside deck. More time capsule than guest house, it provides a distinct counterpoint to the contemporary residence. This is a finished, move-in-ready Winter Harbor compound that brings together contemporary architecture, a preserved vintage lake cabin, approximately 370' +/- of waterfront, extensive boating infrastructure, and approximately 3 acres +/- in one exceptional offering. Please note all acreage, waterfrontage, sq footage, bedrooms and baths have been combined to reflect the whole compound.
MLS # 5108354
Monthly HOA $50
On Site 44 Days
Last Updated 9/9/2026

Listing Agent/Office

Agent Margot Skelley
Office Compass New England, LLC
Office Phone 603-319-4660

Contact Agent

Jason E. Starr

Jason E. Starr

(603) 293-7227

Property Details

Community Information

Address 14 & 20 Gateway Rd, Wolfeboro, NH 03894
County Carroll
City Wolfeboro
Zip Code 03894
Water Body Name Lake Winnipesaukee

School Information

Architecture

Bedrooms 9
Bathrooms 8 Full / 3 Half
Year Built 2022
Stories 2
Style Contemporary, Cottage/Camp
Construction Cedar Exterior
Roof Metal, Architectural Shingle
Foundation Slab w/ Frost Wall
Basement Finished, Full, Insulated, Slab, Interior Stairs, Walkout, Interior Access
Garage Capacity 3

Features / Amenities

Interior Features Blinds, Cathedral Ceiling, Ceiling Fan, Elevator, Passenger Elevator, 1 Fireplace, Kitchen Island, Kitchen/Dining, Kitchen/Family, LED Lighting, Primary BR w/ BA, Natural Light, Security, Walk-in Closet, Walk-in Pantry, Smart Thermostat
Appliances Dishwasher, Dryer, Range Hood, Freezer, Electric Range, Gas Range, Refrigerator, Washer
Equipment Irrigation System, Standby Generator
Flooring Hardwood, Slate/Stone, Tile, Wood
Exterior Features Docks, Covered Slip, Deck, Guest House, Covered Porch
Accessibility Features Paved Parking
Parking Auto Open, Direct Entry, Heated Garage, Paved, Attached
Cooling Central AC, Multi Zone
Heating Electric, Multi Zone, Radiant Floor
Total Rooms 16

Square Footage Finished Sq. Ft.

Above Grade 6366
Below Grade 2929
Total 9295

Square Footage Unfinished Sq. Ft.

Above Grade 1148
Below Grade 246
Total 1394

Property Features

Lot Size 3.2 Acres
Lot Description Landscaped
Lot 36, 37, 39
Water Body Lake
Water Body Name Lake Winnipesaukee
Water Body Access Yes
Water Access Details Directly Adjoining
Waterfront Rights Exclusively Owned
Utilities Cable
Water Drilled Well
Sewer Leach Field, Private, Septic
Electric 200+ Amp Service, Generator
Driveway Paved
Road Frontage Type Association, Paved
Zoning WINNIP
Directions From NH Route 109/Main Street follow to Nary Shore Road. Follow Nary Shores Road to the end where road forks. Bear right. Follow to the end at 14 & 20 Gateway Road.

Tax and Financial Info

Tax Annual Amount $74,382
Tax Year 2025
Association Fee $600 (paid Yearly)
Fee Includes Plowing

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Data last updated October 17, 2026.