Margot Skelley | Compass Real Estate
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Winter Harbor · Wolfeboro, New Hampshire

Intelligent DesignRising Above Winter Harbor

14 & 20 Gateway Road · MLS #5108354$13,900,000
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The Winter Harbor compound

There is nothing like this on Lake Winnipesaukee.

Suspended among the trees above Winter Harbor, one of Lake Winnipesaukee's most distinguished shorelines, 14 & 20 Gateway Road bring together intelligent contemporary design, exceptional waterfront infrastructure, privacy, and a remarkable sense of place.

The centerpiece is an approximately 8,600-square-foot contemporary residence that was engineered by Thornton Tomasetti. Floor-to-ceiling Marvin window walls draw the lake into the interior and frame expansive views across Winter Harbor, including the nightly choreography of New Hampshire sunsets.

Aerial view of the intelligently designed main residence rising above Winter Harbor
Intelligent Design Rising Above Winter Harbor
019,295

approx. +/- combined sq ft

023.20

combined acres

03~370'

combined waterfront

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9

Bedrooms

11

Bathrooms

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14 Gateway · The cabin

14 Gateway Road

The Cabin: A Different Kind of Luxury.

The classic 1958 Winnipesaukee cabin at 14 Gateway offers three bedrooms, one full bath, and approximately two acres with 195 feet of Winter Harbor frontage. Warm wood interiors and a broad lakeside deck preserve its vintage character, while expansive U-shaped covered docking provides substantial room for multiple boats and watercraft. Additional rear acreage offers potential for a barn, garage, workshop, or boat storage, subject to approvals.

1958Classic cabin3Bedrooms195'Water frontage~2Acres
Two waterfront residencesMultiple covered docking optionsApproximately 370' combined frontage
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20 Gateway · Full engineering spectrum

Intelligent Design Rising Above Winter Harbor

Modern Living ~
Timeless Design

Technical specifications and dimensions are provided in the floor plans below.

Level 1 3D floor plan for 20 Gateway Road
06 / Material study

Engineered for Legacy

Brazilian black slate, engineered rift oak flooring, solid rift oak interior doors, custom millwork, stained red cedar siding, Douglas fir porch ceilings, and IPE decking create a consistent, refined material palette throughout the home. Natural quartzite in the living areas and quartz in the baths were hand-selected at Stone Gallery in Massachusetts. Radiant and hydronic heat, open-cell spray foam insulation, and a Viessmann boiler system with an 80-gallon Rinnai hot water reserve provide year-round comfort and efficiency.

Brazilian black slateEngineered rift oakNatural quartziteIPE decking

Entertaining infrastructure

Culinary Infrastructure for the Discerning

The main chef's kitchen anchors the entertaining level with professional-grade appliances and an adjoining walk-in pantry. What sets this home apart is a thoughtfully designed network of secondary kitchenettes and beverage stations distributed throughout the residence, each with its own sink, refrigeration, and counter space. This layered culinary infrastructure accommodates sophisticated entertaining and extended stays without compromising the primary living spaces. Natural quartzite surfaces throughout the public areas ensure both beauty and performance.

The main chef's kitchen with natural quartzite surfaces
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20 Gateway · Spatial journey

Built to Gather

The main residence is designed for both everyday living and larger gatherings. Expansive living rooms, multiple outdoor areas, a media room, guest quarters, and flexible gathering spaces create room to spread out without losing connection to the lake. As a counterpoint, the separate three bedroom, one bath vintage cottage offers its own quieter sense of place along 195 feet of Winter Harbor frontage.

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Level 03

Main living

The social center, shaped for gathering without compromise.
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20 Gateway · Built intelligence

The technology
matches the build.

A carefully integrated systems package supports the scale of the residence while keeping everyday operation quiet, intuitive, and dependable.

01 · Integrated controlControl4

A fully integrated Control4 system governs lighting, climate, Lutron power shades, and distributed audio.

02 · Light managementLutron

Power shades support privacy and solar control across the home's expansive areas of glazing.

03 · Whole-home soundDistributed audio

Built-in distributed audio carries sound through the primary living and entertaining spaces.

04 · Electrical backbone800 amps

Substantial electrical service supports the home's residential, mechanical, and waterfront infrastructure.

05 · Standby power45kW

A whole-house generator maintains essential systems and day-to-day continuity during an outage.

06 · Vertical connection3 stops

A three-stop residential elevator simplifies movement through the vertically organized residence.

07 · Year-round comfortRadiant + hydronic

A Viessmann boiler and an 80-gallon Rinnai hot-water reserve support even, dependable comfort.

08 · Building envelopeMarvin + spray foam

Floor-to-ceiling Marvin window walls pair expansive lake views with open-cell spray-foam insulation.

09 / Waterfront

The compound · Winter Harbor

Waterfront Presence

At 20 Gateway, the rare grandfathered cantilevered steel boathouse, complete with rooftop entertaining deck, is a statement piece. A no-profile boat lift with a solid floor transforms the space when the boat is raised, while a 50-foot aluminum Lift-A-Dock provides additional flexibility. A sandy walk-in beach offers direct, easy access to the lake. At 14 Gateway, 195 feet of Winter Harbor frontage is complemented by expansive U-shaped covered docking already in place, providing substantial capacity for multiple boats and watercraft. Across the compound, approximately 370'+/- of combined frontage brings together a sandy walk-in beach, extensive covered docking, and substantial existing boating infrastructure.

Approximately 370' combined frontageSandy beach · Multiple covered docks
20 Gateway Road illuminated at twilight
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Private view

Presented by Margot Skelley

Experience Winter Harbor with Margot.

For a private showing, full property materials, or a personal introduction to 14 & 20 Gateway Road, contact Margot Skelley directly. She will personally coordinate your visit to this exceptional waterfront compound.