14 & 20 Gateway Road Wolfeboro, NH - Image 114 & 20 Gateway Road Wolfeboro, NH - Image 214 & 20 Gateway Road Wolfeboro, NH - Image 314 & 20 Gateway Road Wolfeboro, NH - Image 414 & 20 Gateway Road Wolfeboro, NH - Image 514 & 20 Gateway Road Wolfeboro, NH - Image 614 & 20 Gateway Road Wolfeboro, NH - Image 714 & 20 Gateway Road Wolfeboro, NH - Image 814 & 20 Gateway Road Wolfeboro, NH - Image 914 & 20 Gateway Road Wolfeboro, NH - Image 1014 & 20 Gateway Road Wolfeboro, NH - Image 1114 & 20 Gateway Road Wolfeboro, NH - Image 1214 & 20 Gateway Road Wolfeboro, NH - Image 1314 & 20 Gateway Road Wolfeboro, NH - Image 1414 & 20 Gateway Road Wolfeboro, NH - Image 1514 & 20 Gateway Road Wolfeboro, NH - Image 1614 & 20 Gateway Road Wolfeboro, NH - Image 1714 & 20 Gateway Road Wolfeboro, NH - Image 1814 & 20 Gateway Road Wolfeboro, NH - Image 1914 & 20 Gateway Road Wolfeboro, NH - Image 2014 & 20 Gateway Road Wolfeboro, NH - Image 2114 & 20 Gateway Road Wolfeboro, NH - Image 2214 & 20 Gateway Road Wolfeboro, NH - Image 2314 & 20 Gateway Road Wolfeboro, NH - Image 2414 & 20 Gateway Road Wolfeboro, NH - Image 2514 & 20 Gateway Road Wolfeboro, NH - Image 2614 & 20 Gateway Road Wolfeboro, NH - Image 2714 & 20 Gateway Road Wolfeboro, NH - Image 2814 & 20 Gateway Road Wolfeboro, NH - Image 2914 & 20 Gateway Road Wolfeboro, NH - Image 3014 & 20 Gateway Road Wolfeboro, NH - Image 3114 & 20 Gateway Road Wolfeboro, NH - Image 3214 & 20 Gateway Road Wolfeboro, NH - Image 3314 & 20 Gateway Road Wolfeboro, NH - Image 3414 & 20 Gateway Road Wolfeboro, NH - Image 3514 & 20 Gateway Road Wolfeboro, NH - Image 3614 & 20 Gateway Road Wolfeboro, NH - Image 3714 & 20 Gateway Road Wolfeboro, NH - Image 3814 & 20 Gateway Road Wolfeboro, NH - Image 3914 & 20 Gateway Road Wolfeboro, NH - Image 4014 & 20 Gateway Road Wolfeboro, NH - Image 4114 & 20 Gateway Road Wolfeboro, NH - Image 4214 & 20 Gateway Road Wolfeboro, NH - Image 4314 & 20 Gateway Road Wolfeboro, NH - Image 4414 & 20 Gateway Road Wolfeboro, NH - Image 4514 & 20 Gateway Road Wolfeboro, NH - Image 4614 & 20 Gateway Road Wolfeboro, NH - Image 4714 & 20 Gateway Road Wolfeboro, NH - Image 4814 & 20 Gateway Road Wolfeboro, NH - Image 4914 & 20 Gateway Road Wolfeboro, NH - Image 5014 & 20 Gateway Road Wolfeboro, NH - Image 5114 & 20 Gateway Road Wolfeboro, NH - Image 5214 & 20 Gateway Road Wolfeboro, NH - Image 5314 & 20 Gateway Road Wolfeboro, NH - Image 5414 & 20 Gateway Road Wolfeboro, NH - Image 5514 & 20 Gateway Road Wolfeboro, NH - Image 5614 & 20 Gateway Road Wolfeboro, NH - Image 5714 & 20 Gateway Road Wolfeboro, NH - Image 5814 & 20 Gateway Road Wolfeboro, NH - Image 59

$13,900,000

9 Beds 8 / 3 Full / Half Baths 9,295 SQFT 3.20 Acres
Type: Single Family

14 & 20 Gateway Road
Wolfeboro, NH 03894

MLS#: 5108354
Chris Bernier
Chris Bernier
Churchill Properties
Principal Broker/Owner
Phone: 978.578.5013
Office: 833.668.4649
Presented by: Margot Skelley with Compass New England, LLC;

Property 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.


 

Interior Features

Bedrooms

Beds9

Other Interior Features

InternetHigh Speed Intrnt at Site
Total Finished Area9,295 sqft
Basement Access TypeInterior
BasementYes
Basement DescriptionFinished, Full, Insulated, Slab, Interior Stairs, Walkout, Interior Access
FlooringHardwood, Slate/Stone, Tile, Wood
Interior AmenitiesBlinds, 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 P

Other Rooms

Total Rooms16

General

3/4 Baths0
Accessibility FeaturesPaved Parking
AppliancesDishwasher, Dryer, Range Hood, Freezer, Electric Range, Gas Range, Refrigerator, Washer
Assoc Fee Paid PerYearly
Bathrooms11
Block0
CityWolfeboro
Construction MaterialsCedar Exterior
CoolingCentral AC, Multi Zone
CovenantsUnknown
DOM52
DirectionsFrom 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.
Electric200+ Amp Service, Generator
Elementary SchoolCarpenter Elementary
Fee IncludesPlowing
Flood ZoneNo
Full Baths8
GarageYes
HOA Fee$600
Half Baths3
HeatingElectric, Multi Zone, Radiant Floor
High SchoolKingswood Regional High School
Last Updated09/09/2026 09:57:49
Middle SchoolKingswood Regional Middle
Other EquipmentIrrigation System, Standby Generator
Price Per Sq Ft Total AG$2,183
Property ClassResidential
Property ConditionExisting
Road FrontageNo
RoofMetal, Architectural Shingle
School DistrictGovernor Wentworth Regional
SeasonalNo
SewerLeach Field, Private, Septic
Status Detail0
Stories Count2
StyleContemporary, Cottage/Camp
Tax Annual Amount$74,382
Tax Year2025
TypeSingle Family
UtilitiesCable
Year Built2022
ZoningWINNIP

Exterior

ColorBrown
DrivewayPaved
Exterior AmenitiesDocks, Covered Slip, Deck, Guest House, Covered Porch
Foundation Slab w/ Frost Wall
Garage Capacity3
Lot36, 37, 39
Lot FeaturesLandscaped
Lot Size Area3 sqft
Lot Size Square Feet139,392 sqft
Parking FeaturesAuto Open, Direct Entry, Heated Garage, Paved, Attached
Road Frontage TypeAssociation, Paved
SurveyedYes
Water Access DetailsDirectly Adjoining
Water Body AccessYes
Water Body NameLake Winnipesaukee
Water Body TypeLake
Water Frontage Length370 sqft
Water SourceDrilled Well
Water ViewYes
Waterfront PropertyYes

Additional Details

Price History

Schools 

Middle School Kingswood Regional Middle
High School Kingswood Regional High School
Elementary School Carpenter Elementary

  

Similar Properties

$13,900,000

9 Beds 8 / 3 Full / Half Baths 9,295 SQFT 3.20 Acres
Type: Single Family

14 & 20 Gateway Road
Wolfeboro, NH 03894

MLS#: 5108354
Chris Bernier
Chris Bernier
Churchill Properties
Principal Broker/Owner
Phone: 978.578.5013
Office: 833.668.4649