Date
Details
Price
Change
Source
9/04/2026
Listed
$13,900,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$13,900,000 Coming Soon
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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.
Full Property Details
Full Property Details for 14 & 20 Gateway Rd
General
- Price: $13,900,000
- Taxes: $74,382 (2025)
- Status: Coming Soon
- Type: Single Family
- Source: PrimeMLS
- MLS ID: 5108354
- Updated: 9/5/2026
- Added to Site: Today
Interior
- Number of Rooms: 16
- 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
- Fireplace: Yes
- Appliances: Dishwasher, Dryer, Range Hood, Freezer, Electric Range, Gas Range, Refrigerator, Washer
- Flooring: Hardwood, Slate/Stone, Tile, Wood
Rooms
Bathrooms
- Total Bathrooms: 11
- Full Bathrooms: 8
- Half Bathrooms: 3
Bedrooms
- Total Bedrooms: 9
Additional Information
- Equipment: Irrigation System, Standby Generator
Exterior
- Exterior Features: Docks, Covered Slip, Deck, Guesthouse, Covered Porch
- Color: Brown
Parking
- Garage: Yes
- Garage Spaces: 3
- Parking: Auto Open, Direct Entry, Heated Garage, Paved, Attached
Location
- County: Carroll
- Driving 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.
School Information
- School District: Governor Wentworth Regional
- Elementary School: Carpenter Elementary
- Middle School: Kingswood Regional Middle
- High School: Kingswood Regional High School
Heating & Cooling
- Cooling Type: Central AC, Multi Zone
- Heating Type: Electric, Multi Zone, Radiant Floor
Utilities
- Sewer: Leach Field, Private, Septic
Structural Information
- Construction Status: Existing
- Basement Entrance: Interior
- Basement Desc.: Finished, Full, Insulated, Interior Access, Interior Stairs, Slab, Walkout
- Roof: Architectural Shingle, Metal
- Stories/Levels: 2
- Square Feet: 9,295
- Finished Total: 9,295 Sq. Ft.
- Finished Above Grnd: 6,366 Sq. Ft.
- Finished Below Grnd: 2,929 Sq. Ft.
- Year Built: 2022
Lot Features
- Lot Size (Acres): 3.2
- Lot Size (Sq. Ft.): 139,392
- Frontage: No Road Frontage
- Driveway/Sidewalk: Paved
- Zoning: WINNIP
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Front Type: Lake
- Water Front Name: Lake Winnipesaukee
- Water Front Owned: 1
Financial Considerations
- Price Per Sq. Ft.: $2,183.47
- Other Fee: Fee 1: $600
- Other Fee Type: Fee 1 Includes: Plowing
- Other Fee Freq.: Fee 1 Frequency: Yearly
- Tax Amount: $74,382
- Tax Year: 2025
Disclosures and Reports
- Surveyed: Yes
- Lot Number: 363739
Listed by Compass New England, LLC, Margot Skelley
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We Value Your Privacy
We Value Your Privacy
Listed by Compass New England, LLC, Margot Skelley
Listing agent
— 14 & 20 Gateway Rd —
Margot Skelley
Compass New England, LLC
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 14 & 20 Gateway Rd
School District:Governor Wentworth Regional School District
| Name | Grades | Distance |
|---|---|---|
Carpenter Elementary School 102 South Main Street, Wolfeboro, NH 03894 | K-3 | 1.9 mi |
Crescent Lake School 75 McManus Road, Wolfeboro, NH 03894 | 4-6 | 3.2 mi |
Kingswood Regional Middle School 404 South Main Street, Wolfeboro, NH 03894 | 7-8 | 3.1 mi |
Kingswood Regional High School 396 South Main Street, Wolfeboro, NH 03894 | 9-12 | 3.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 14 & 20 Gateway Rd
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14 & 20 Gateway Road, Wolfeboro, NH 03894 (MLS# 5108354) is a Single Family property with 9 bedrooms, 8 full bathrooms and 3 partial bathrooms. 14 & 20 Gateway Road is currently listed for $13,900,000 and was received on September 04, 2026. Want to learn more about 14 & 20 Gateway Road? Do you have questions about finding other Single Family real estate for sale in Wolfeboro? You can browse all Wolfeboro real estate or contact a Coldwell Banker agent to request more information.