14 & 20 Gateway Road, Wolfeboro, NH

$13,900,000

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9

Beds

11

Baths

9,295

Square feet

3.20

Acres

About 14 & 20 Gateway Road

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.

Features of 14 & 20 Gateway Road

MLS® # 5108354
Price $13,900,000
Bedrooms 9
Bathrooms 11.00
Full Baths 8
Half Baths 3
Square Footage 9,295
Acres 3.20
Year Built 2022
Type Residential
Sub-Type Residential
Status Active

Community Information

Address 14 & 20 Gateway Road
Area Wolfeboro
City Wolfeboro
County Carroll
State NH
Zip Code 03894

Amenities

Utilities Cable
Is Waterfront No
Waterfront Lake
Has Pool No

Interior

Interior Hardwood, Slate/Stone, Tile, Wood
Appliances Dishwasher, Dryer, Range Hood, Freezer, Electric Range, Gas Range, Refrigerator, Washer
Heating Electric, Multi Zone, Radiant Floor
Cooling Central AC, Multi Zone
Fireplace No
# of Stories 2

Exterior

Roof Metal, Architectural Shingle
Waterfront Name Lake Winnipesaukee

School Information

District Governor Wentworth Regional
Elementary Carpenter Elementary
Middle Kingswood Regional Middle
High Kingswood Regional High School

Additional Information

Date Listed September 4th, 2026
Zoning WINNIP

Listing Details

AgentMargot Skelley
OfficeCompass New England, LLC

Listing Map

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