# 14 & 20 Gateway Road, Wolfeboro, NH 03894 > **TL;DR:** 9bd/11ba single family, $13,900,000 ($1495/sqft), built 2022, 9,295 sqft. > Fireplace, Waterfront, Hardwood, A/C. Est. $74,940/mo. Listed 17 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $13,900,000 | | Price/sqft | $1495 | | Bedrooms | 9 | | Bathrooms | 8 full, 3 half | | Square Feet | 9,295 | | Year Built | 2022 | | Lot Size | 139,392 sqft (3.20 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 17 | ## Why This Home Stands Out - **Waterfront** - Waterfront location listed - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $70,286 | | Estimated Insurance | $4,054 | | HOA | $600 | | **Total** | **$74,940** | ## Nearby Schools - **Elementary:** Carpenter Elementary - **Middle:** Kingswood Regional Middle - **High:** Kingswood Regional High School ## Key Amenities - Fireplace - Waterfront - Hardwood - A/C ## Property Highlights - Built in 2022 - 3.20 acre lot - 2 stories - Fireplace - Waterfront ## Description ### Agent 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. ## Location - **Address:** 14 & 20 Gateway Road, Wolfeboro, NH 03894 - **County:** NH-Carroll - **Coordinates:** 43.58944431, -71.24737089 - **Google Maps:** https://www.google.com/maps?q=43.58944431,-71.24737089 ## Virtual Tour & Media - **Video Tour:** https://listings.wolfreel.media/video/zj7EJ00L6hoaheclGV2QnSgB02WBxUtYFSDYDpCR02Wvm00 ## Listing Agent - **Name:** Margot Skelley - **Brokerage:** Compass New England, LLC - **Phone:** (603) 540-5661 - **Broker Phone:** (603) 540-5661 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/14-and-20-Gateway-Rd_Wolfeboro_NH_03894_M93624-27986?f=listhub&s=NNERENNH&m=5108354&c=propsimple) ## Photos ![14 & 20 Gateway Road - Photo 1](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1422574652r.jpg) ![14 & 20 Gateway Road - Photo 2](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3608142888r.jpg) ![14 & 20 Gateway Road - Photo 3](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f78885864r.jpg) ![14 & 20 Gateway Road - Photo 4](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f291016315r.jpg) ![14 & 20 Gateway Road - Photo 5](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3117367129r.jpg) ![14 & 20 Gateway Road - Photo 6](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3343049019r.jpg) ![14 & 20 Gateway Road - Photo 7](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3902113265r.jpg) ![14 & 20 Gateway Road - Photo 8](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f559512248r.jpg) ![14 & 20 Gateway Road - Photo 9](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2036004157r.jpg) ![14 & 20 Gateway Road - Photo 10](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f23839451r.jpg) ![14 & 20 Gateway Road - Photo 11](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2580096468r.jpg) ![14 & 20 Gateway Road - Photo 12](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2239652844r.jpg) ![14 & 20 Gateway Road - Photo 13](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3935980532r.jpg) ![14 & 20 Gateway Road - Photo 14](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3861403492r.jpg) ![14 & 20 Gateway Road - Photo 15](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f32398157r.jpg) ![14 & 20 Gateway Road - Photo 16](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1700844898r.jpg) ![14 & 20 Gateway Road - Photo 17](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f557997230r.jpg) ![14 & 20 Gateway Road - Photo 18](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f4269957899r.jpg) ![14 & 20 Gateway Road - Photo 19](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1380353542r.jpg) ![14 & 20 Gateway Road - Photo 20](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f214499825r.jpg) ![14 & 20 Gateway Road - Photo 21](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f734824802r.jpg) ![14 & 20 Gateway Road - Photo 22](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2063072579r.jpg) ![14 & 20 Gateway Road - 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Photo 33](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f4175685868r.jpg) ![14 & 20 Gateway Road - Photo 34](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1407479312r.jpg) ![14 & 20 Gateway Road - Photo 35](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2976213319r.jpg) ![14 & 20 Gateway Road - Photo 36](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3072874016r.jpg) ![14 & 20 Gateway Road - Photo 37](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3243400004r.jpg) ![14 & 20 Gateway Road - Photo 38](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1091903181r.jpg) ![14 & 20 Gateway Road - Photo 39](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1156717478r.jpg) ![14 & 20 Gateway Road - Photo 40](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3542851411r.jpg) ![14 & 20 Gateway Road - Photo 41](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f437056493r.jpg) ![14 & 20 Gateway Road - Photo 42](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3539265302r.jpg) ![14 & 20 Gateway Road - Photo 43](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3501947779r.jpg) ![14 & 20 Gateway Road - Photo 44](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1189298725r.jpg) ![14 & 20 Gateway Road - Photo 45](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3151803554r.jpg) ![14 & 20 Gateway Road - Photo 46](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f4026055127r.jpg) ![14 & 20 Gateway Road - Photo 47](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2742705807r.jpg) ![14 & 20 Gateway Road - Photo 48](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2252862187r.jpg) ![14 & 20 Gateway Road - Photo 49](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1622420901r.jpg) ![14 & 20 Gateway Road - Photo 50](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f981696073r.jpg) ![14 & 20 Gateway Road - Photo 51](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2708993335r.jpg) ![14 & 20 Gateway Road - Photo 52](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f681898052r.jpg) ![14 & 20 Gateway Road - Photo 53](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f959364628r.jpg) ![14 & 20 Gateway Road - Photo 54](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1765689353r.jpg) ![14 & 20 Gateway Road - Photo 55](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2924882567r.jpg) ![14 & 20 Gateway Road - Photo 56](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3317591076r.jpg) ![14 & 20 Gateway Road - Photo 57](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f1561911718r.jpg) ![14 & 20 Gateway Road - Photo 58](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f2593850634r.jpg) ![14 & 20 Gateway Road - Photo 59](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3120851018r.jpg) ![14 & 20 Gateway Road - Photo 60](http://lh.rdcpix.com/74dffe800f3e7336eca77eb4ec8e71e1l-f3876338213r.jpg) --- **MLS#:** 5108354 | **Updated:** 2026-09-20 **Source:** listhub *Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/14-20-gateway-road-wolfeboro-nh-03894-5108354) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/14-20-gateway-road-wolfeboro-nh-03894-5108354#listing", "url": "https://www.propertysimple.ai/listing/14-20-gateway-road-wolfeboro-nh-03894-5108354", "name": "14 & 20 Gateway Road, Wolfeboro, NH 03894", "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. 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