Wolfeboro: a Brief History
Nestled in the foothills of the White Mountains and on the shores of Lake Winnipesaukee, Wolfeboro, New Hampshire traces its history back to 1759 and is “the oldest summer resort town in America.” The town’s name was in honor of General John Wolfe. In 1763 Governor John Wentworth established an estate on the site known as “Kingswood.” This was the first summer country estate in Northern New England. The town was eventually incorporated in 1770.
Wolfeboro, Today:
If the town fathers could see Wolfeboro today, they would be very proud. South and North Main Streets display shuttered white colonial homes and picket fences with a vibrant New England shopping district along Wolfeboro Bay’s water’s edge. Quaint shops like Black’s Paper Store + Gift Shop dating back to 1867 line the scenic roadway with fine dining establishments, pubs, and café’s overlooking blazing sunsets along the shoreline. The town is renowned for its beautiful estate homes that dot its majestic shoreline with dramatic westerly lake and mountain views. Many cultural events are enjoyed year-round in this thriving small resort town with its gazebo bandstand in Cate Park overlooking the town docks and boat ramp. I was in Wolfeboro yesterday and was impressed that all of the town docks were in the final stages of rebuilding…they looked fantastic; what quality construction!
The 18 hole Kingswood Golf Club is right up the road from the shopping district, and the 18 hole Lake Winnipesaukee Golf Club is only 5 miles from the center of Wolfeboro.
Brewster Academy, established in 1820, is a sprawling 80-acre campus with classic New England facilities, including a half-mile of shoreline in the town along Lake Winnipesaukee.
In addition to Lake Winnipesaukee, the town is blessed with Lake Wentworth, Crescent Lake, Rust Pond, and the Smith River. Wolfeboro has a population of about 6,416 (54th in New Hampshire) that swells to approximately 25,000 during the summer tourist season. The town consists of the main village of Wolfeboro as well as the smaller village of Wolfeboro Falls. The “Back Bay Area” is a scenic waterway that flows under the Back Bay Bridge to restaurants, the Sawmill Marina, and Water Ski Events near the former Wolfeboro Train Station is the Bucolic 11 mile Cotton Valley Raid Trail, Home to joggers and bicyclists.
Wolfeboro contains 48.3 square miles of land area and 10.1 square miles of inland water area. There are approximately 4,846 total housing units in town. Grades k-12 are part of the Governor Wentworth Regional School District. There are 2 elementary schools with approximately 455 students, a middle school with approximately 371, and Kingswood Regional High School with close to 900 students. The Lakes Region Technology Center is another excellent facility in town.
Huggins Hospital on the main street is a 25-bed critical access hospital affiliated with Catholic Medical Center in Manchester. There are several town beaches and parks, the Libby and Wright Museums, 3 marinas (Goodhue Boat Company, Wolfeboro Corinthian Yacht Club, and Sawmill Marina), the Nick Recreational Complex, The Wolfeboro Trolly Co., The Abenaki Ski Area, one of the country’s oldest small ski area’s, Kingswood Arts Center, Village Players Theatre on the Green, Arts & Crafts Festival, The NH Boat Museum, and so much more. The historic Wolfeboro Inn, Lake Wentworth Inn, 123 N Main B&B, Windrifter Resort, Lakeview Inn, the new luxury Pickering House Inn, and many more hospitality offerings are located in town.
Many famous and influential people have spent time and have been drawn to live in Wolfeboro over the years. In Wolfeboro, you feel like you’ve stepped back in time to a simpler place where nothing has changed. Yes, the town has retained its authenticity and Norman Rockwell appeal.
Real Estate Trends in Wolfeboro, NH
So how is the real estate market in Wolfeboro performing over the past 3 years:
- In 2021 there were 122 single-family home sales. The median sales price was $422,000. The average sales price was $560,710. The highest sales price was $4,997,100. Median days on the market was 10. Total sales volume was $68,406,739.
- In 2021 there were 14 condominium sales. The median sales price was $457,500. The average sales price was $477,849. The highest sales price was $699,999. Median days on the market was 8. Total sales volume was $6,889,893.
- In 2020 there were 138 single-family home sales. The median sales price was $377,500. The average sales price was $635,576. The highest sales price was $3,990,000. Median days on the market was 27. Total sales volume was $87,709,598.
- In 2020 there were 12 condominium sales. The median sales price was $425,987. The average sales price was $437,973. The highest sales price was $725,000. Median days on the market was 4. Total sales volume was $5,255,680.
- In 2019 there were 138 single-family home sales. The median sales price was $332,500. The average sales price was $616,612. The highest sales price was $7,750,000. Median days on the market was 33. Total sales volume was $85,009,759.
- In 2019 there were 25 condominium sales. The median sales price was $375,000. The average sales price was $410,356. The highest sales price was $625,000. Median days on the market was 28. Total sales volume was $10,258,900.
- As of this writing, there are only 5 “active” single-family homes available for sale in Wolfeboro. The median listing price is $2,950,000. The average listing price is $6,885,800. The highest listing price is $19,500,000. Median days on the market is 135
- There are no condominiums currently for sale.
Based on the above, there is one certainty out there… the oldest summer resort in America is still one of its best! However, Wolfeboro needs to replenish its available inventory soon.

This article was written by Frank Roche. Frank is president of Roche Realty Group with offices in Meredith and Laconia, NH, and can be reached at (603) 279-7046. Town data was compiled by a NEREN search on 12/08/2021 at 11:00 am EST and is subject to change. Please feel free to visit www.rocherealty.com to learn more about the Lakes Region and its real estate market.
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20 WYMAN, Wolfeboro, NH 03894
MLS #4958433
City:Wolfeboro, State:NH
Price: $10950000
Extraordinarily private 6.2 acre site featuring 430' of prime frontage along the highly coveted southern shores of Lake Winnipesaukee's Wolfeboro Neck. Architecturally designed, and expertly crafted for a family unrestrained by budget. The result is a near 15, 000 square foot, 7Bed/8Bath masterpiece unlike anything else in the Northeast. The home enjoys S/SW exposure and exceptional, long-range views. There are no neighbors in view and you'll enjoy more than 5, 000SF of patio, deck and balconies, along with a remarkable, 2-slip boathouse and breakwater. The property will allow for additional structures to include a guest house or caretaker's cottage, a hobby barn, greenhouse or any number of recreational options. Inside, the home features soaring ceilings above intimate living spaces. A wall of windows pours natural light into the Great Room, where the owners have enjoyed hosting not only friends and family, but private events and concerts. An adjacent media room provides privacy without sacrificing views of the lake, which is less than 30' away! The kitchen was designed for the homeowner (a classically trained chef) and features both butler's and dry good pantries, professional appliances, stone counters and easy access to the rear deck for grilling. The home offers a professional waterside gym, spa and sauna, an elevator for ease of access and much more. Homes of this caliber rarely become available and they are virtually impossible to recreate. By appointment only. 6494ab5834e2b567f74950b4 6.20 15810 Interior 1 0 6 1 8 7 14778 Wolfeboro RE_1 NH-Carroll From downtown Wolfeboro drive North on Main Street take left onto Forest Road. Take a left onto Spruce Road and then right onto Wyman Drive. No drive-by's please. 20 WYMAN Drive neren3 2 1 6494a92234e2b5678b0d8bf4 1 1 1 1 1756437847 1687464143 10950000 Jamieson Duston 4958433 Active Lake View View Walking Trails Water View Wooded 270072 4958433 6096 20 WYMAN, Wolfeboro, NH 03894 1757550748 Cell: 603-365-5848 Duston Leddy Real Estate 49 740 Single Family Homes Residential Extraordinarily private 6.2 acre site featuring 430' of prime frontage along the highly coveted southern shores of Lake Winnipesaukee's Wolfeboro Neck. Architecturally designed, and expertly crafted for a family unrestrained by budget. The result is a near 15, 000 square foot, 7Bed/8Bath masterpiece unlike anything else in the Northeast. The home enjoys S/SW exposure and exceptional, long-range views. There are no neighbors in view and you'll enjoy more than 5, 000SF of patio, deck and balconies, along with a remarkable, 2-slip boathouse and breakwater. The property will allow for additional structures to include a guest house or caretaker's cottage, a hobby barn, greenhouse or any number of recreational options. Inside, the home features soaring ceilings above intimate living spaces. A wall of windows pours natural light into the Great Room, where the owners have enjoyed hosting not only friends and family, but private events and concerts. An adjacent media room provides privacy without sacrificing views of the lake, which is less than 30' away! The kitchen was designed for the homeowner (a classically trained chef) and features both butler's and dry good pantries, professional appliances, stone counters and easy access to the rear deck for grilling. The home offers a professional waterside gym, spa and sauna, an elevator for ease of access and much more. Homes of this caliber rarely become available and they are virtually impossible to recreate. By appointment only. Dead End Private Governor Wentworth Regional Carpenter Elementary Kingswood Regional High School Kingswood Regional Middle NH 2 WYMAN 20 Modern Architecture 1758583722 https://vimeo.com/seacoastrevideo/review/793411517/6dabfb7d6b Deep Water Access Yes Lake Winnipesaukee No Lake 430 Yes 1 Exclusively Owned 2005 03894 ListPrice 10950000 1710943991 10950000 1687464792 12500000 ListingStatus Active 1687464792 Active https://s3.us-central-1.wasabisys.com/apiv1.photos.master/c810-4958433-1-neren3.jpg 1 1756438618 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/0c3f-4958433-2-neren3.jpg 2 1756438618 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/5f4f-4958433-3-neren3.jpg 3 1756438618 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/24b5-4958433-4-neren3.jpg 4 1756438618 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/b3c8-4958433-5-neren3.jpg 5 1756438618 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/f3f9-4958433-6-neren3.jpg 6 1756438618 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