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$13,900,000
2 Days On Site

14 & 20 Gateway Road
Wolfeboro, NH 03894

Single Family Residence|Coming Soon
9
Beds
11
Total Baths
8
Full Baths
3
Partial Baths
9,295
SqFt
$1,495
/SqFt
2022
Built
County:
Carroll
Listing courtesy of Margot Skelley of Compass New England, LLC
Call Now: (978) 710-9388
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(978) 710-9388
14 & 20 Gateway Road14 & 20 Gateway Road14 & 20 Gateway Road14 & 20 Gateway Road
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Mortgage Calculator

Monthly Payment (Est.)

$63,417
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$13,900,000
Days On Site 
2 Days
Bedrooms 
9
Inside Area (SqFt) 
9,295 sqft
Total Baths 
11
Full Baths 
8
Partial Baths 
3
Lot Size 
3.2 Acres
Year Built 
2022
MLS® Number 
5108354
Status 
Coming Soon
Property Tax 
$74,382
HOA/Condo/Coop Fees 
$50 monthly
Sq Ft Source 
N/A
Friends & Family
Recent Activity
yesterdayListing updated with changes from the MLS®
3 days agoListing first seen on site
General Features
Acres 
3.2
Garage 
Yes
Garage Spaces 
3
Number Of Stories 
2
Parking 
PavedHeated GarageAttached
Parking Spaces 
3
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Above 
6366
SqFt Below 
2929
SqFt Total 
10689
Style 
ContemporaryCottage/Camp
Utilities 
Cable Available
Water Source 
Well
Zoning 
WINNIP
Interior Features
Appliances 
DishwasherDryerFreezerRefrigeratorWasherRange HoodElectric RangeGas Range
Basement 
FinishedFull
Cooling 
Central Air
Electric 
200+ Amp ServiceGenerator
Flooring 
HardwoodTileWood
Heating 
RadiantElectricRadiant Floor
Interior 
ElevatorKitchen IslandSmart Thermostat
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Exterior Features
Construction Details 
Cedar
Exterior 
Dock
Lot Features 
LandscapedWaterfront
Patio And Porch 
DeckPorch
Roof 
MetalShingle
View 
Water
Waterfront 
Yes
Waterfront Features 
Lake
Waterview 
Water
Community Features
Association Dues 
600
HOA Fee Frequency 
Annually
School District 
Governor Wentworth Regional
Schools
School District
Governor Wentworth Regional
Elementary School
Carpenter Elementary
Middle School
Kingswood Regional Middle
High School
Kingswood Regional High School
Listing courtesy of Margot Skelley of Compass New England, LLC



Copyright 2026, PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Last checked: 2026-09-07 11:56 AM UTC
Neighborhood & Commute
Source: Walkscore
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