Listed by Compass New England, LLC · Margot Skelley · 603-319-4660
Single Family Residence · Wolfeboro, NH
14 & 20 Gateway Road, Wolfeboro, NH
$13,900,000
Est. $70,286/mo · 20% down, 30-yr, 6.5% (Owl’s Nest Real Estate estimate, not MLS data)
- Beds
- 9
- Baths
- 11
- Sq Ft
- 6,366
- Built
- 2022
- MLS®
- #5108354
Property Description
14 & 20 Gateway Road sits in Wolfeboro, New Hampshire — a single-family home offering 9 bedrooms, 11 bathrooms and 6,366 square feet of living space. The asking price is $13,900,000. The format is the classic one — a standalone home with no association between you and your plans for it. Beyond the basics, the listing carries a 3.2-acre lot, garage parking for 3 and 2022 construction. See the listing's full details below, and reach out for a private showing of 14 & 20 Gateway Road. Browse more homes for sale in Wolfeboro.
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 Highlights
14 & 20 Gateway Road is a single family residence in Wolfeboro, New Hampshire, listed at $13,900,000. That works out to about $2,183 per square foot, for a home built in 2022. It has been on the market for 8 weeks.
From here it is 24.7 miles to Downtown Plymouth / Main Street and 28 miles to Owl's Nest Resort. At this latitude, Wolfeboro averages roughly 8.4 hours of sun a day in June and 3.6 in December.
Zoned schools in the Governor Wentworth Regional: Carpenter Elementary (Elementary), Kingswood Regional Middle (Middle), KingswoodR (High). Always confirm zoning with the district office.
Source: zoned school names are PrimeMLS listing data; distances, sun exposure and school facts are Owl’s Nest Real Estate additions (school facts from the NCES, U.S. Department of Education) — not PrimeMLS data.
Property Details
Essentials & finishes
- Bedrooms
- 9
- Total Baths
- 11
- Full Baths
- 8
- SqFt
- 6,366
- Price / SqFt
- $2183.47
- Property Type
- Single Family Residence
- Year Built
- 2022
- County
- NH-Carroll
- Town
- Wolfeboro, NH
- Status
- Active
- Days on Market
- 41
Primary Features
- County
- NH-Carroll
- Property Type
- Residential
- Year Built
- 2022
- Zoning
- WINNIP
Interior Features
- Appliances
- Dishwasher, Dryer, Range Hood, Freezer, Electric Range, Gas Range, Refrigerator, Washer
- Basement
- Yes
- Basement Access Type
- Interior
- Basement Description
- Finished, Full, Insulated, Slab, Interior Entry, Interior Stairs, Walk-Out Access
- 1/4 Baths
- 0
- 3/4 Baths
- 0
- Cooling
- Central Air, Zoned
- Electric
- 200+ Amp Service, Generator
- Flooring
- Hardwood, Slate/Stone, Tile, Wood
- Heating
- Electric, Zoned, Radiant Floor
- Interior Features
- 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
- Rooms - Total
- 16
- SqFt-Approximate Finished Above Grade
- 6,366
- SqFt-Approximate Finished Below Grade
- 2,929
- SqFt Approximate Total Finished
- 9,295
- SqFt Approximate Total
- 10,689
Location Information
- School - District
- Governor Wentworth Regional
- School - Elementary
- Carpenter Elementary
- School - High
- KingswoodR
- School - Middle/Jr
- Kingswood Regional Middle
Financial Details
- Association Fee
- $600
- Fee Frequency
- Yearly
- Fee Includes
- Plowing
- Tax - Gross Amount
- $74,382
- Tax Year
- 2025
- Taxes TBD
- No
Additional
- Construction Status
- Existing
- Construction
- Cedar
- Covenants
- Unknown
- Flood Zone
- No
- Pre-Construction
- No
- Property Sub Type
- Single Family Residence
- Seasonal
- No
- Total Stories
- Two
- Surveyed
- Yes
- Timeshare/Fractional Ownership
- No
- Water Access Details
- Directly Adjoining
External Features
- Color
- Brown
- Driveway
- Paved
- Exterior Features
- Covered Slip, Deck, Dock, Guest House, Covered Porch
- Foundation
- Slab w/ Frost Wall
- Garage
- Yes
- Garage Capacity
- 3
- Lot Features
- Landscaped
- Lot - Acres
- 3.2
- Lot - SqFt
- 139,392
- Parking
- Attached, Auto Open, Direct Access, Heated Garage, Paved
- Road Frontage Type
- Association, Paved
- Road Frontage
- No
- Roof
- Metal, Architectural Shingle
- Sewer
- Leach Field, Private, Septic Tank
- Utilities
- Cable
- Water Source
- Drilled Well
- Water Body Type
- Lake
MLS®: PrimeMLS #5108354; Listed by Compass New England, LLC · Margot Skelley · 603-319-4660
Property History
Estimated annual taxes for this property
- 2024
- $236,300
- 2023
- $230,393
- 2022
- $224,485
Source: Owl’s Nest Real Estate estimate from the list price at New Hampshire’s average effective tax rate — not PrimeMLS or town assessor data. Verify with the town assessor.
Market Data
Live snapshot computed by Owl’s Nest Real Estate from PrimeMLS IDX active listings in this town
- Active listings in Wolfeboro
- 76
- Average list price
- $592,158
- Price range
- $170,000 – $1,685,000
Mortgage Calculator
Estimate your monthly payment for this home
Estimated Monthly Payment
$92,873/ mo
- Principal & Interest
- $70,286
- Property Tax
- $19,692
- Home Insurance
- $2,896
Source: Owl’s Nest Real Estate estimate, not PrimeMLS data. Estimates use typical New Hampshire costs — a 1.7% effective property-tax rate, insurance at 0.25% of home value/yr, and PMI below 20% down. Actual town tax rates vary; verify with your lender and the town assessor.
Around This Property
Schools, everyday places and nearby destinations near 14 & 20 Gateway Road, Wolfeboro, NH
Assigned Schools
- Elementary
- Carpenter Elementary
- Middle
- Kingswood Regional Middle
- High School
- KingswoodR
- District
- Governor Wentworth Regional
Source: Google Maps Platform (Places) and Owl’s Nest Real Estate — not PrimeMLS data.
Questions About This Listing
How big is 14 & 20 Gateway Road?
14 & 20 Gateway Road in Wolfeboro, NH has 9 bedrooms and 11 bathrooms (8 full and 3 half) in 6,366 square feet of finished living space.
Counting 2,929 finished square feet below grade, the MLS lists 9,295 finished square feet in total.
What is the asking price of 14 & 20 Gateway Road?
14 & 20 Gateway Road in Wolfeboro, NH is listed for $13,900,000 on PrimeMLS.
That is about $2,183 per square foot of finished living space.
It came on the market on September 4, 2026.
Where is 14 & 20 Gateway Road located?
14 & 20 Gateway Road is in Wolfeboro, New Hampshire 03894, in Carroll County.
Our Lakes Region guide covers Wolfeboro and the surrounding towns.
How much land comes with 14 & 20 Gateway Road?
14 & 20 Gateway Road in Wolfeboro, NH sits on 3.2 acres, per the MLS.
The lot is described as landscaped.
Zoning: WINNIP.
The MLS says the lot has been surveyed.
The MLS lists it as outside a flood zone.
How much are the property taxes on 14 & 20 Gateway Road?
Annual property taxes on 14 & 20 Gateway Road in Wolfeboro, NH are $74,382 for the 2025 tax year, per the MLS.
New Hampshire towns set their own tax rates and revalue periodically, so confirm the current bill with the Wolfeboro assessing office.
Is there an HOA fee at 14 & 20 Gateway Road?
The association fee for 14 & 20 Gateway Road in Wolfeboro, NH is $600 (yearly), per the MLS.
The MLS lists the fee as covering plowing.
Ask for the association documents and budget to see exactly what the fee covers.
How is 14 & 20 Gateway Road heated?
14 & 20 Gateway Road in Wolfeboro, NH is heated by electric, zoned and radiant floor, per the MLS.
Cooling: central air and zoned.
Does 14 & 20 Gateway Road have town water and sewer?
14 & 20 Gateway Road in Wolfeboro, NH has a private drilled well and a private septic system, per the MLS.
MLS details — water: drilled well; sewer: leach field, private and septic tank.
Electric: 200+ amp service and generator.
Other utilities: cable.
Plan a water test and septic inspection during your inspection period.
Is there a basement at 14 & 20 Gateway Road?
Yes. 14 & 20 Gateway Road in Wolfeboro, NH has a basement with interior access, including 2,929 finished square feet.
The MLS describes it as finished, full, insulated, slab, interior entry, interior stairs and walk-out access.
What features does 14 & 20 Gateway Road have?
Inside, the MLS lists these features at 14 & 20 Gateway Road in Wolfeboro, NH: blinds, cathedral ceiling(s), ceiling fan(s), elevator, passenger elevator, 1 fireplace, kitchen island and kitchen/dining.
Outside: covered slip, deck, dock, guest house and covered porch.
Flooring: hardwood, slate/stone, tile and wood.
Listed appliances: dishwasher, dryer, range hood, freezer, electric range, gas range, refrigerator and washer; confirm which ones convey in the purchase agreement.
Does 14 & 20 Gateway Road have a garage?
14 & 20 Gateway Road in Wolfeboro, NH has a 3-car garage and a paved driveway.
Parking details: attached, auto open, direct access, heated garage and paved.
Is 14 & 20 Gateway Road on the water?
Yes. The MLS lists 14 & 20 Gateway Road in Wolfeboro, NH as a waterfront property on a lake.
Water access: directly adjoining.
The MLS lists a dock.
Confirm frontage, shoreland rules and any dock or beach rights during due diligence.
What schools serve 14 & 20 Gateway Road?
The MLS places 14 & 20 Gateway Road in Wolfeboro, NH in the Governor Wentworth Regional school district.
Listed schools: Carpenter Elementary (elementary), Kingswood Regional Middle (middle) and KingswoodR (high).
School assignments can change; confirm with the district.
Is 14 & 20 Gateway Road still available?
Yes. 14 & 20 Gateway Road in Wolfeboro, NH is listed as Active on PrimeMLS (MLS #5108354).
Status can change quickly; contact us to confirm availability before you visit.
Who is the listing agent for 14 & 20 Gateway Road?
14 & 20 Gateway Road in Wolfeboro, NH is listed by Margot Skelley of Compass New England, LLC (603-319-4660).
Owl's Nest Real Estate shows it through the PrimeMLS IDX feed; we are not the listing brokerage.
What kind of property is 14 & 20 Gateway Road?
14 & 20 Gateway Road in Wolfeboro, NH is a single-family home built in 2022.
The MLS lists its style as Contemporary, Cottage/Camp, with two stories.
How does the price of 14 & 20 Gateway Road compare with other Wolfeboro listings?
At $13,900,000, 14 & 20 Gateway Road in Wolfeboro, NH is priced above the $877,000 median asking price of the 46 single-family homes for sale in Wolfeboro on PrimeMLS as of November 3, 2026 (this listing included).
That figure is Owl's Nest Real Estate's analysis of active listings, and asking prices are not sale prices — ask us for recent comparable sales before you make an offer.
How do I schedule a showing of 14 & 20 Gateway Road?
To see 14 & 20 Gateway Road in Wolfeboro, NH, use Request a Showing on this page or call Owl's Nest Real Estate at 401-648-5308.
We can show any MLS-listed home and represent you as your buyer's agent; the listing brokerage represents the seller.
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NOTE: This representation is based in whole or in part on data generated by PrimeMLS, Inc., which assumes no responsibility for its accuracy. The data relating to real estate displayed on this site comes in part from the IDX Program of PrimeMLS.
This listing data is intended for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 11/03/26.