Listed by Duston Leddy Real Estate · Jamieson Duston · Cell: 603-365-5848
Single Family Residence · Wolfeboro, NH
20 WYMAN Drive, Wolfeboro, NH
$10,950,000
Est. $55,369/mo · 20% down, 30-yr, 6.5% (Owl’s Nest Real Estate estimate, not MLS data)
- Beds
- 7
- Baths
- 8
- Sq Ft
- 14,778
- Built
- 2005
- MLS®
- #5086004
Property Description
A single-family home with New Hampshire roots, 20 WYMAN Drive in Wolfeboro dates to 2005 and lists at $10,950,000. The home provides 7 bedrooms, 8 bathrooms and 14,778 square feet of living space. Single-family ownership here means your own land, your own walls and room to make the property yours. The numbers worth knowing: a 6.2-acre lot, garage parking for 2 and roughly $741 per square foot. The full photo gallery, live pricing and every MLS detail for 20 WYMAN Drive follow below. Browse more homes for sale in Wolfeboro.
Commanding a rare and remarkably private 6.2-acre site along the sun-drenched edge of Lake Winnipesaukee, this Wolfeboro Neck estate occupies one of the most coveted stretches in all of New Hampshire's lakes region. With an extraordinary 430 feet of frontage and uninterrupted south-to-southwest exposure, the property captures sweeping, cinematic views across the Broads, without a neighboring home in sight. It is a setting of uncommon seclusion within one of the region’s most prestigious enclaves. The residence itself, spanning nearly 15,000 square feet, was conceived on a grand architectural scale, offering 7 bedrooms and 8 baths across a layout designed for both entertaining and retreat. The home presents a compelling opportunity for a discerning owner to curate and elevate the interiors to their own high standards, transforming it into a truly bespoke lakeside compound. Outdoor living is equally ambitious, with more than 5,000 square feet of terraces, decks, and balconies that unfold toward the water, creating an effortless flow between interior and exterior spaces. A two-slip boathouse with protective breakwater anchors the waterfront experience, while the acreage affords exceptional flexibility for the addition of a guest residence, caretaker’s cottage, or recreational barn. Inside, a soaring great room wrapped in glass frames the lake as living art, flooding the home with natural light. The layout balances grand entertaining spaces with intimate retreats, including a private media room and a chef’s kitchen. Wellness amenities include a fully equipped gym, spa, and sauna, all oriented toward the tranquil lakefront. Defined by its irreplaceable combination of scale, privacy, and premier Wolfeboro Neck location, this offering represents a singular opportunity to craft a generational estate on one of New Hampshire’s most storied lakes. By appointment.
Location Highlights
20 WYMAN Drive is a single family residence in Wolfeboro, New Hampshire, listed at $10,950,000. That works out to about $741 per square foot, for a home built in 2005. It has been on the market for 6 months.
From here it is 25 miles to Downtown Plymouth / Main Street and 28.6 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
- 7
- Total Baths
- 8
- Full Baths
- 1
- SqFt
- 14,778
- Price / SqFt
- $740.97
- Property Type
- Single Family Residence
- Year Built
- 2005
- County
- NH-Carroll
- Town
- Wolfeboro, NH
- Status
- Active
- Days on Market
- 174
Primary Features
- County
- NH-Carroll
- Property Type
- Residential
- Year Built
- 2005
- Zoning
- WINNIPESAUKEE
Interior Features
- Appliances
- Water Heater off Boiler
- Basement
- Yes
- Basement Access Type
- Interior
- Basement Description
- Climate Controlled, Concrete, Concrete Floor, Full, Interior Stairs, Unfinished
- 1/4 Baths
- 0
- 3/4 Baths
- 6
- Cooling
- Central Air
- Electric
- Circuit Breakers, Generator
- Heating
- Forced Air, Oil, Radiator
- Interior Features
- Blinds, Cathedral Ceiling(s), Dining Area, Passenger Elevator, Wood Fireplace, 2 Fireplaces, Kitchen Island, Responsive Lite Contrl(s), Sauna, Soaking Tub, Vaulted Ceiling(s), Walk-In Closet(s), Walk-in Pantry, 1st Floor Laundry
- Rooms - Total
- 14
- SqFt-Approximate Finished Above Grade
- 14,778
- SqFt-Approximate Finished Below Grade
- 0
- SqFt Approximate Total Finished
- 14,778
- SqFt Approximate Total
- 16,778
Location Information
- School - District
- Governor Wentworth Regional
- School - Elementary
- Carpenter Elementary
- School - High
- KingswoodR
- School - Middle/Jr
- Kingswood Regional Middle
Financial Details
- Tax - Gross Amount
- $84,308
- Tax Year
- 2025
- Taxes TBD
- No
Additional
- Construction Status
- Existing
- Construction
- Steel Frame, Wood Frame
- Covenants
- No
- 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
- Deep Water Access, Directly Adjoining
External Features
- Color
- BARK
- Driveway
- Gravel
- Exterior Features
- Balcony, Boat House, Boat Mooring, Boat Slip, Covered Slip, Deck, Garden, Hot Tub, Natural Shade, Patio, Private Dock, Handicap Modified
- Foundation
- Poured Concrete
- Garage
- Yes
- Garage Capacity
- 2
- Lot Features
- Walking Trails, Wooded
- Lot - Acres
- 6.2
- Lot - SqFt
- 270,072
- Parking
- Attached
- Road Frontage Type
- Dead End, Private Road
- Road Frontage
- Yes
- Road Frontage Length
- 86
- Roof
- Wood Shingle
- Sewer
- Private, Septic Tank
- Utilities
- Underground Utilities
- Water Source
- Drilled Well, Private
- Water Body Type
- Lake
MLS®: PrimeMLS #5086004; Listed by Duston Leddy Real Estate · Jamieson Duston · Cell: 603-365-5848
Market Data
Live snapshot computed by Owl’s Nest Real Estate from PrimeMLS IDX active listings in this town
- Active listings in Wolfeboro
- 79
- Average list price
- $659,658
- Price range
- $299,000 – $1,995,000
Mortgage Calculator
Estimate your monthly payment for this home
Estimated Monthly Payment
$64,676/ mo
- Principal & Interest
- $55,369
- Property Tax
- $7,026
- Home Insurance
- $2,281
Property tax: this home’s 2025 annual tax bill of $84,308, per PrimeMLS. The rest is an Owl’s Nest Real Estate estimate: insurance at 0.25% of home value/yr and PMI below 20% down. A sale can trigger a reassessment; confirm with the town assessor and your lender.
Around This Property
Schools, everyday places and nearby destinations near 20 WYMAN Drive, 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 much does 20 WYMAN Drive cost?
20 WYMAN Drive in Wolfeboro, NH is listed for $10,950,000 on PrimeMLS.
That is about $741 per square foot of finished living space.
It came on the market on April 29, 2026.
How many bedrooms and bathrooms does 20 WYMAN Drive have?
20 WYMAN Drive in Wolfeboro, NH has 7 bedrooms and 8 bathrooms (1 full, 6 three-quarter and 1 half) in 14,778 square feet of finished living space.
What parking does 20 WYMAN Drive have?
20 WYMAN Drive in Wolfeboro, NH has a 2-car garage and a gravel driveway.
Parking details: attached.
Is 20 WYMAN Drive a waterfront property?
Yes. The MLS lists 20 WYMAN Drive in Wolfeboro, NH as a waterfront property on a lake.
Water access: deep water access and directly adjoining.
The MLS lists a private dock.
Confirm frontage, shoreland rules and any dock or beach rights during due diligence.
What school district is 20 WYMAN Drive in?
The MLS places 20 WYMAN Drive 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 20 WYMAN Drive still for sale?
Yes. 20 WYMAN Drive in Wolfeboro, NH is listed as Active on PrimeMLS (MLS #5086004).
Status can change quickly; contact us to confirm availability before you visit.
Which brokerage has 20 WYMAN Drive listed?
20 WYMAN Drive in Wolfeboro, NH is listed by Jamieson Duston of Duston Leddy Real Estate (603-610-8285).
Owl's Nest Real Estate shows it through the PrimeMLS IDX feed; we are not the listing brokerage.
What type of home is 20 WYMAN Drive?
20 WYMAN Drive in Wolfeboro, NH is a single-family home built in 2005.
The MLS lists its style as Modern Architecture, with two stories.
What town is 20 WYMAN Drive in?
20 WYMAN Drive is in Wolfeboro, New Hampshire 03894, in Carroll County.
Location notes from the MLS: walking trails.
Our Lakes Region guide covers Wolfeboro and the surrounding towns.
What is the lot size of 20 WYMAN Drive?
20 WYMAN Drive in Wolfeboro, NH sits on 6.2 acres, per the MLS.
The lot is described as wooded.
It has 86 feet of road frontage (dead end and private road).
Zoning: WINNIPESAUKEE.
The MLS says the lot has been surveyed.
The MLS lists it as outside a flood zone.
What are the annual property taxes for 20 WYMAN Drive?
Annual property taxes on 20 WYMAN Drive in Wolfeboro, NH are $84,308 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.
What heating and cooling does 20 WYMAN Drive have?
20 WYMAN Drive in Wolfeboro, NH is heated by forced air, oil and radiator, per the MLS.
Cooling: central air.
What are the water and sewer systems at 20 WYMAN Drive?
20 WYMAN Drive in Wolfeboro, NH has a private drilled well and a private septic system, per the MLS.
MLS details — water: drilled well and private; sewer: private and septic tank.
Electric: circuit breakers and generator.
Other utilities: underground utilities.
Plan a water test and septic inspection during your inspection period.
Does 20 WYMAN Drive have a basement?
Yes. 20 WYMAN Drive in Wolfeboro, NH has a basement with interior access.
The MLS describes it as climate controlled, concrete, concrete floor, full, interior stairs and unfinished.
What are the key features of 20 WYMAN Drive?
Inside, the MLS lists these features at 20 WYMAN Drive in Wolfeboro, NH: blinds, cathedral ceiling(s), dining area, passenger elevator, wood fireplace, 2 fireplaces, kitchen island and responsive lite contrl(s).
Outside: balcony, boat house, boat mooring, boat slip, covered slip, deck, garden and hot tub.
Listed appliances: water heater off boiler; confirm which ones convey in the purchase agreement.
How does the price of 20 WYMAN Drive compare with other Wolfeboro listings?
At $10,950,000, 20 WYMAN Drive in Wolfeboro, NH is priced above the $875,000 median asking price of the 49 single-family homes for sale in Wolfeboro on PrimeMLS as of November 5, 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 can I see 20 WYMAN Drive in person?
To see 20 WYMAN Drive 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.
Similar Listings in Wolfeboro
$459,900
2 bd | 1 ba | 1,101 ft²
29 Pine Street, Wolfeboro, NH
Single Family Residence
MLS® #5116910 · Century 21 Lifestyles
$1,995,000
4 bd | 5 ba | 4,662 ft²
165 Ambrose Way, Wolfeboro, NH
Single Family Residence
MLS® #5116852 · KW Coastal and Lakes & Mountains Realty/Wolfeboro
$299,000
0 bd | 0 ba
16 Varney Road, Wolfeboro, NH
Single Family Residence
MLS® #5116840 · KW Coastal and Lakes & Mountains Realty/Wolfeboro
$915,000
3 bd | 2 ba | 2,117 ft²
4 Whispering Pines Way, Wolfeboro, NH
Single Family Residence
MLS® #5116649 · Maxfield Real Estate/Wolfeboro
$699,000
3 bd | 2 ba | 2,360 ft²
325 Middleton Road, Wolfeboro, NH
Single Family Residence
MLS® #5116805 · KW Coastal and Lakes & Mountains Realty/Wolfeboro
$875,000
4 bd | 2 ba | 2,429 ft²
15 Tibbetts Road, Wolfeboro, NH
Single Family Residence
MLS® #5116696 · Wild Tracks Realty
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 11/04/26.