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.
Wolfeboro, NH — The Oldest Summer Resort Town In America - Page2
Wolfeboro, NH — The Oldest Summer Resort Town In America - Page3
222 N. Main, Wolfeboro, NH 03894
MLS #5068852
City:Wolfeboro, State:NH
Price: $2995000
Built in 1895, this magnificent Victorian residence stands as one of Wolfeboroâs finest off-lake estatesâwhere historic craftsmanship meets contemporary luxury living. Set on 2.7 acres along the townâs idyllic North Main Street, the home offers rare privacy within walking distance to the village and Lake Winnipesaukee. Inside, original woodwork, oversized windows and five fireplaces evoke a grander era, while thoughtful renovations introduce contemporary comfort. The designer kitchen features Miele, Bosch and Wolf appliances along with custom cabinetry and a butlerâs pantry with a copper sink. 7 bedrooms and 5 baths provide ample space for family and guests. Gathering rooms, a movie room and a workshop add versatility, while a ground-level studio opens to a 35Ã25 patio â perfect for a painter, potter, or summer entertainer. The original 2, 500 sq. ft. carriage house includes a four-car garage ideal for collectors. Outdoors, an 18Ã40 heated pool with swim jet and pergola anchors lush, landscaped grounds. With town approval, the property would also be suitable for a luxury inn, wedding venue or condominiums. Property is on public water and sewer. Meticulously maintained and lovingly restored, this home represents Wolfeboroâs architectural heritage at its most graceful â a timeless in-town estate that balances history, artistry, and modern ease. 690debb834e2b5f8216b64e3 2.70 282190 In Town Near Golf Course Near Snowmobile Trails Near Shopping Near Skiing Walkout DayLight 2 0 1 2 5 7 7138 Wolfeboro RE_1 NH-Carroll 1/2 mile on the left heading north from downtown Wolfeboro 222 N. Main Street neren3 6 1 690deb4334e2b5f80e169d32 1 1 1762519792 1762519789 2995000 Sara Reineman 5068852 Active Trail/Near Trail Walking Trails 117612 5068852 5534 222 N. Main, Wolfeboro, NH 03894 1767382813 Cell: 781-708-5825 BHHS Verani Wolfeboro 60 1109259 419 Single Family Homes Residential Built in 1895, this magnificent Victorian residence stands as one of Wolfeboroâs finest off-lake estatesâwhere historic craftsmanship meets contemporary luxury living. Set on 2.7 acres along the townâs idyllic North Main Street, the home offers rare privacy within walking distance to the village and Lake Winnipesaukee. Inside, original woodwork, oversized windows and five fireplaces evoke a grander era, while thoughtful renovations introduce contemporary comfort. The designer kitchen features Miele, Bosch and Wolf appliances along with custom cabinetry and a butlerâs pantry with a copper sink. 7 bedrooms and 5 baths provide ample space for family and guests. Gathering rooms, a movie room and a workshop add versatility, while a ground-level studio opens to a 35Ã25 patio â perfect for a painter, potter, or summer entertainer. The original 2, 500 sq. ft. carriage house includes a four-car garage ideal for collectors. Outdoors, an 18Ã40 heated pool with swim jet and pergola anchors lush, landscaped grounds. With town approval, the property would also be suitable for a luxury inn, wedding venue or condominiums. Property is on public water and sewer. Meticulously maintained and lovingly restored, this home represents Wolfeboroâs architectural heritage at its most graceful â a timeless in-town estate that balances history, artistry, and modern ease. Public Governor Wentworth Regional Carpenter Elementary Kingswood Regional High School Kingswood Regional Middle NH 1762473600 3 N. Main 222 Victorian 1768540944 https://drive.google.com/file/d/1fW3QJU9pQALSevKZLpXpCyGPHRrjat7J/view?usp=sharing 1890 03894 ListPrice 2995000 1762519992 2995000 ListingStatus Active 1762519992 Active https://s3.us-central-1.wasabisys.com/apiv1.photos.master/8d71-5068852-1-neren3.jpg 1 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/c0b1-5068852-2-neren3.jpg 2 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/b96e-5068852-3-neren3.jpg 3 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/c6bf-5068852-4-neren3.jpg 4 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/5a23-5068852-5-neren3.jpg 5 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/5444-5068852-6-neren3.jpg 6 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/74cb-5068852-7-neren3.jpg 7 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/ef9d-5068852-8-neren3.jpg 8 1762527299 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https://s3.us-central-1.wasabisys.com/apiv1.photos.master/a6a9-5068852-59-neren3.jpg 59 1762527299 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/1f1b-5068852-60-neren3.jpg 60 1762527299 1762527299 1762527361 43.5901880 -71.2269442 Point -71.2269442 43.590188 RETS https://tour.neren.com/222-N-Main-Street-Wolfeboro-NH-03894/unbranded5A Delings Cove, Wolfeboro, NH 03894
MLS #5045764
City:Wolfeboro, State:NH
Price: $6305000
This is a rare opportunity to build your dream waterfront home on Springfield Point. This 6, 565 sq. ft. custom-built estate is crafted for those who cherish luxury in an unparalleled location. Situated on a .86-acre level lot in one of the lake's most exclusive areas, you have 150 feet of pristine water frontage and a gradual sandy beach. A cobblestone path leads through beautifully landscaped grounds to the grand entrance, setting the stage for elegance within. The outdoor spaces are spectacular, featuring a bluestone patio with a firepit for entertaining or relaxing with breathtaking lake views. A Sonos sound system enhances the ambiance, merging aesthetics with functionality. The home's exterior exudes timeless sophistication with pre-primed LP Smart siding and Beach House Vinyl Shakes. Inside, discover 9-foot ceilings, engineered hardwood floors, and heated bathroom floors. Enjoy real stone veneer fireplaces, reclaimed barn wood mantels, and a gourmet kitchen equipped with Wolf and Sub-Zero appliances and a Miele coffee machine. In addition to the first-floor primary suite, and heated porch. Additional highlights include a heated 3-car garage, standby generator, and a full DVR camera system. Don't miss the opportunity to own this lakeside masterpiece. Schedule a private tour meeting today with a top builder in the lakes region and step into the luxurious lifestyle that awaits you on Lake Winnipesaukee. Subject to lot survey- 68496e2634e2b5e40822e9d3 0.86 17079 Interior 1 0 0 4 5 4 6565 Wolfeboro RE_1 NH-Carroll 5A Delings Cove Road neren3 3 1 68496daf34e2b5e3f62f3332 1 1 1 1 1752594485 1749642424 6305000 Adam Dow 5045764 Active Lake View Level View Water View 37462 5045764 2416 5A Delings Cove, Wolfeboro, NH 03894 1763061184 Phone: 866-525-3946 KW Coastal and Lakes & Mountains Realty/Wolfeboro 20 7331395 960 Single Family Homes Residential This is a rare opportunity to build your dream waterfront home on Springfield Point. This 6, 565 sq. ft. custom-built estate is crafted for those who cherish luxury in an unparalleled location. Situated on a .86-acre level lot in one of the lake's most exclusive areas, you have 150 feet of pristine water frontage and a gradual sandy beach. A cobblestone path leads through beautifully landscaped grounds to the grand entrance, setting the stage for elegance within. The outdoor spaces are spectacular, featuring a bluestone patio with a firepit for entertaining or relaxing with breathtaking lake views. A Sonos sound system enhances the ambiance, merging aesthetics with functionality. The home's exterior exudes timeless sophistication with pre-primed LP Smart siding and Beach House Vinyl Shakes. Inside, discover 9-foot ceilings, engineered hardwood floors, and heated bathroom floors. Enjoy real stone veneer fireplaces, reclaimed barn wood mantels, and a gourmet kitchen equipped with Wolf and Sub-Zero appliances and a Miele coffee machine. In addition to the first-floor primary suite, and heated porch. Additional highlights include a heated 3-car garage, standby generator, and a full DVR camera system. Don't miss the opportunity to own this lakeside masterpiece. Schedule a private tour meeting today with a top builder in the lakes region and step into the luxurious lifestyle that awaits you on Lake Winnipesaukee. Subject to lot survey- Private Public Governor Wentworth Regional Kingswood Regional High School NH 1749600000 2 Delings Cove 5A Contemporary 1768540737 Beach Access Directly Adjoining Dock Access Yes Lake Winnipesaukee Lake 150 Yes 1 Exclusively Owned 03894 ListPrice 6305000 1763061790 6305000 1756395190 6405000 1749642790 6600000 ListingStatus Active 1749642790 Active https://s3.us-central-1.wasabisys.com/apiv1.photos.master/adf9-5045764-1-neren3.jpg 1 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/15e0-5045764-2-neren3.jpg 2 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/c58c-5045764-3-neren3.jpg 3 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/8ddd-5045764-4-neren3.jpg 4 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/b49d-5045764-5-neren3.jpg 5 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/5256-5045764-6-neren3.jpg 6 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/1fcb-5045764-7-neren3.jpg 7 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/e8c3-5045764-8-neren3.jpg 8 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/512e-5045764-9-neren3.jpg 9 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/0b7a-5045764-10-neren3.jpg 10 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/6e09-5045764-11-neren3.jpg 11 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/c71c-5045764-12-neren3.jpg 12 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/5a7f-5045764-13-neren3.jpg 13 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/4399-5045764-14-neren3.jpg 14 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/3ebb-5045764-15-neren3.jpg 15 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/beab-5045764-16-neren3.jpg 16 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/e340-5045764-17-neren3.jpg 17 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/4829-5045764-18-neren3.jpg 18 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/640b-5045764-19-neren3.jpg 19 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/7630-5045764-20-neren3.jpg 20 1752594857 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/ad13-5045764-21-neren3.jpg 21 1752259925 1752594857 1752594924 43.5612560 -71.1928240 Point -71.192824 43.561256 RETS https://tour.neren.com/5A-Delings-Cove-Road-Wolfeboro-NH-03894/unbranded Near Golf Course Near Shopping Near Skiing -1.59 1763061790















































