Courtesy Of Margot Skelley Of Compass New England, Llc
14 & 20 Gateway Rd
Wolfeboro, NH 03894
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
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
Compass New England, LLC Office Phone 603-319-4660
Contact Agent
Jason E. Starr
(603) 293-7227Property 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
School System
Governor Wentworth Regional
High School
Kingswood Regional High School
Middle School
Kingswood Regional Middle
Elementary School
Carpenter Elementary
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
Mortgage Calculator
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Purchase price
Down payment
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Data last updated October 17, 2026.
