Skip to main content
Wolfeboro, NH

14 & 20 Gateway Road

$13,900,0005 days on market

MLS# 5108354 · Single Family Residence

Back to results
The Listing

A 9-bedroom home in Wolfeboro on Lake Winnipesaukee.

9
Bedrooms
11
Baths
9,295
Sq Ft
3.2
Acres
Waterfront· Lake Winnipesaukee· Directly Adjoining

Description

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

Interior

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
Security
Walk-In Closet(s)
Walk-in Pantry
Smart Thermostat

Exterior

Dock
Covered Slip
Deck
Guest House
Covered Porch

Heating

Electric
Zoned
Radiant Floor

Cooling

Central Air
Zoned

Parking

Auto Open
Direct Access
Heated Garage
Paved
Attached

Request Information

Interested in this property? One of our agents will follow up with you directly.

Financial

Annual Taxes
$74,382
HOA Fee
$600/yr

Location

Sale History

DateSale Price
Apr 5, 2019$2,150,000
Residential · NH-Carroll County · Listed Sep 4, 2026

About Wolfeboro, NH

Known as "The Oldest Summer Resort in America," Wolfeboro sits at the eastern shore of Lake Winnipesaukee. Its walkable downtown features independent shops, restaurants, and the New Hampshire Boat Museum. Year-round residents enjoy excellent schools, a vibrant arts scene, and easy access to multiple lakes.

Walkable downtown with shops & dining
New Hampshire Boat Museum
Cotton Valley Trail (12-mile rail trail)
Brewster Academy (private school)
Access to Winnipesaukee, Wentworth & Crescent lakes
Wright Museum of WWII
County: Carroll
Population: ~6,300
Schools: Governor Wentworth Regional (SAU 49)

Distances are approximate. Click any destination for driving directions. NH has no state income tax or sales tax.

Other Waterfront Listings on Lake Winnipesaukee

AddressPrice
36 Tiger Trail$12,950,000
137 Brown Road$12,899,000
59 Broadview Terrace$11,750,000
20 WYMAN Drive$10,950,000

Active listings within 25% of this price. Browse all for-sale.

Recently Sold in Wolfeboro

AddressSold PriceSold
6 Bassett Road$599,000Aug 31, 2026
5 Trask Mountain Road$675,000Aug 28, 2026
78 Beach Pond Road$325,000Aug 24, 2026
108 Whitten Neck Road$1,535,000Aug 19, 2026
Map 25-6 Upper Trask Mountain Road$200,000Aug 18, 2026
61 Central Avenue$1,320,000Aug 17, 2026

Closed sales in the past 12 months. Data from PrimeMLS.

$13,900,000

Active Listing

Bedrooms9
Bathrooms11
Sq Ft9,295
$/Sq Ft$1495
Listing courtesy of Compass New England, LLC · Margot Skelley · 603-319-4660
PrimeMLS

IDX display courtesy of Yankee Pedlar Realtors, Wolfeboro NH.

PrimeMLS Listing Information displayed herein is deemed reliable but is not guaranteed accurate by PrimeMLS. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. © PrimeMLS, Inc.

Listing brokers may report inaccurate data to michelle@yankeepedlarrealtors.com or call (603) 569-1000.