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For Sale

14 & 20 Gateway Road

Wolfeboro, NH 03894

$13,900,000

$1,495 per sq ft

Listed Sep 4 · 7 days on market

9

Beds

11

Baths

9,295

Sq ft

3.2

Acres

Listed by Margot Skelley, Compass New England, LLC · 603-319-4660

About this home

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.

Virtual tour

Schools

Carpenter ElementaryElementary
Kingswood Regional MiddleMiddle
KingswoodRHigh

Key features

  • Blinds
  • Cathedral Ceiling(s)
  • Ceiling Fan(s)
  • Elevator
  • Passenger Elevator
  • 1 Fireplace
  • Kitchen Island
  • Kitchen/Dining
  • Kitchen/Family
  • LED Lighting
  • Primary BR w/ BA
  • Natural Light
Kate FossJen Russell

See it with Kate and Jen.

We'll set up the showing, walk you through it, and tell you what we really think.

Details

TypeSingle family
StyleContemporary, Cottage/Camp
Year built2022
Finished sq ft9,295
Lot3.2 acres
Garage3 spaces
BasementFinished, Full, Insulated, Interior Entry, Slab, Interior Stairs, Walk-Out Access
HeatingElectric, Zoned, Radiant Floor
CoolingCentral Air, Zoned
WaterDrilled Well
SewerLeach Field, Private, Septic Tank
RoofMetal, Architectural Shingle
ConstructionCedar
FlooringHardwood, Slate/Stone, Tile, Wood
Taxes$74,382 (2025)
Association fee$600 yearly
ZoningWINNIP
WaterfrontLake Winnipesaukee
Days on market7
MLS #5108354
PrimeMLS

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 09/16/26.