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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80 Parker Island, Wolfeboro, NH 03894
MLS #5089994
City:Wolfeboro, State:NH
Price: $9500000
Lake Winnipesaukee waterfront living at its finest. "Woodland Cove" is set on three private acres with 310 feet of pristine sandy shoreline and coveted southern exposure, this extraordinary custom estate captures sweeping views of the lake and the Belknap Mountain range while offering rare protection from prevailing winds. The sugar sand beach allows you to wade in slowly with a sandy bottom extending well off shore. The park-like grounds are a masterpiece of natural beauty, featuring mature gardens, handcrafted stonework, and multiple outdoor living spaces designed to embrace the waterfront setting. A stunning mahogany-and-fieldstone boathouse which is architecturally exceptionalâstands as a true centerpiece of the property. The boathouse features a large lift to keep your boat pristine as well. Spanning more than 8, 000 square feet, the 13-room residence combines timeless craftsmanship with luxurious comfort. The home features six spacious bedrooms and seven baths, with every bedroom offering its own en-suite bath for ultimate privacy and convenience. Soaring ceilings, elegant crown molding, and walls of glass create an atmosphere of light, space, and sophistication throughout. The decorator furnishings have been curated specifically for this home and are included. Designed for both relaxed lake living and entertaining, the home offers expansive decks, patios, and a beautiful screened porch that seamlessly blends indoor and outdoor living. The first-floor primary suite is a private retreat with breathtaking lake and mountain views, a generous walk-in closet, and a spa-inspired bath. Located just 10 minutes from downtown Wolfeboro, this remarkable property delivers the perfect balance of convenience, exclusivity, and complete privacy on New Hampshireâs most sought-after lake. This is truly a special property in the nations "Oldest Summer Resort." 6a0e0c7634e2b5884c68a725 3.03 8479 Near Golf Course Near Skiing Walkout Finished 1 0 3 3 7 6 8144 Wolfeboro RE_1 NH-Carroll Follow Forest Road to a left on Parker Island Road. Take right to follow even numbered homes. Follow to #80 on right. 80 Parker Island Road neren3 3 1 6a0e0bec34e2b58837673c93 1 1 1779305324 43.5794199 1779305323 9500000 Brian Neidhardt 5089994 Active -71.2632126 Lake View Mountain View Secluded View Water View 131987 5089994 1309 80 Parker Island, Wolfeboro, NH 03894 1779483312 Four Seasons Sotheby's Int'l Realty 46 3135313 1166 Single Family Homes Residential Lake Winnipesaukee waterfront living at its finest. "Woodland Cove" is set on three private acres with 310 feet of pristine sandy shoreline and coveted southern exposure, this extraordinary custom estate captures sweeping views of the lake and the Belknap Mountain range while offering rare protection from prevailing winds. The sugar sand beach allows you to wade in slowly with a sandy bottom extending well off shore. The park-like grounds are a masterpiece of natural beauty, featuring mature gardens, handcrafted stonework, and multiple outdoor living spaces designed to embrace the waterfront setting. A stunning mahogany-and-fieldstone boathouse which is architecturally exceptionalâstands as a true centerpiece of the property. The boathouse features a large lift to keep your boat pristine as well. Spanning more than 8, 000 square feet, the 13-room residence combines timeless craftsmanship with luxurious comfort. The home features six spacious bedrooms and seven baths, with every bedroom offering its own en-suite bath for ultimate privacy and convenience. Soaring ceilings, elegant crown molding, and walls of glass create an atmosphere of light, space, and sophistication throughout. The decorator furnishings have been curated specifically for this home and are included. Designed for both relaxed lake living and entertaining, the home offers expansive decks, patios, and a beautiful screened porch that seamlessly blends indoor and outdoor living. The first-floor primary suite is a private retreat with breathtaking lake and mountain views, a generous walk-in closet, and a spa-inspired bath. Located just 10 minutes from downtown Wolfeboro, this remarkable property delivers the perfect balance of convenience, exclusivity, and complete privacy on New Hampshireâs most sought-after lake. This is truly a special property in the nations "Oldest Summer Resort." Governor Wentworth Regional Carpenter Elementary Kingswood Regional High School Kingswood Regional Middle NH 1779408000 2 Parker Island 80 Contemporary 1779483790 Deep Water Access Yes Lake Winnipesaukee No Lake 310 Yes 1 Exclusively Owned 2007 03894 ListPrice 9500000 1779305590 9500000 ListingStatus Active 1779433991 Active 1779305590 Coming Soon Point -71.2632126 43.5794199 RETS https://s3.us-central-1.wasabisys.com/apiv1.photos.master/d1dd-5089994-1-neren3.jpg 1 1779306886 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/12ad-5089994-2-neren3.jpg 2 1779306886 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/9ccc-5089994-3-neren3.jpg 3 1779306886 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/e598-5089994-4-neren3.jpg 4 1779306886 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/5821-5089994-5-neren3.jpg 5 1779306886 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/3a8d-5089994-6-neren3.jpg 6 1779306886 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1779306946 https://listings.flylisted.com/video/qVXgHliuwNiOnFweal3VfyEp1nPiNTqgmSVsxMNbVDU https://my.matterport.com/show/?m=R9mXRdCc9QS606 and 607 N. Main, Wolfeboro, NH 03894
MLS #5095854
City:Wolfeboro, State:NH
Price: $9800000
A truly rare offering on the shores of Winter Harbor, this remarkable 40± acre property presents a once-in-a-generation opportunity to own one of the most extraordinary waterfront estates in Wolfeboro. Comprised of two distinct 20-acre parcels, the property captures the very essence of lakeside New England living. On the lake side of North Main Street, an antique seasonal cottage overlooks the sparkling waters of Lake Winnipesaukee, where breathtaking sunsets paint the sky above Winter Harbor each evening. Sandy waterfront, sweeping views, and the tranquil setting create an idyllic retreat to enjoy today while envisioning what tomorrow may bring. Across the road, rolling fields and open meadows surround an antique Cape, forming a timeless pastoral landscape rich with character and possibility. The existing home offers an opportunity for restoration or redevelopment, while the gently sloping terrain provides exceptional flexibility for future plans, including the potential for walkout lower levels designed to maximize both views and indoor-outdoor living. Whether your vision is a private family compound, an equestrian estate, a multigenerational retreat, or a thoughtfully designed development opportunity, the rare combination of substantial acreage, waterfront, open fields, and lake views offers possibilities that are nearly impossible to replicate in today's market. This is a property meant to be cherished, shaped by its next steward, and enjoyed for generations to come. Adding to its appeal is the location itself. Welcome to Wolfeboro, often regarded as one of New England's most charming villages. Here, you'll find the perfect balance of peace and privacy while remaining just minutes from the vibrant downtown, with its boutique shops, restaurants, marinas, and year-round community events. 6a36b05e34e2b5d664641dd2 40.83 17158 Near Golf Course 0 0 1 0 1 3 1400 Wolfeboro RE_1 NH-Carroll 606 and 607 N. Main Street neren3 6a36aefd34e2b5d6270fdff2 1 1 1 1781968365 43.6080062 1781968364 9800000 Lobin Frizzell 5095854 Active -71.2547535 Agricultural Country Setting Lake View Level Mountain View View Water View Wooded Field/Pasture 1778555 5095854 2418 606 and 607 N. Main, Wolfeboro, NH 03894 1781977876 KW Coastal and Lakes & Mountains Realty/Meredith 58 240019 7000 Single Family Homes Residential A truly rare offering on the shores of Winter Harbor, this remarkable 40± acre property presents a once-in-a-generation opportunity to own one of the most extraordinary waterfront estates in Wolfeboro. Comprised of two distinct 20-acre parcels, the property captures the very essence of lakeside New England living. On the lake side of North Main Street, an antique seasonal cottage overlooks the sparkling waters of Lake Winnipesaukee, where breathtaking sunsets paint the sky above Winter Harbor each evening. Sandy waterfront, sweeping views, and the tranquil setting create an idyllic retreat to enjoy today while envisioning what tomorrow may bring. Across the road, rolling fields and open meadows surround an antique Cape, forming a timeless pastoral landscape rich with character and possibility. The existing home offers an opportunity for restoration or redevelopment, while the gently sloping terrain provides exceptional flexibility for future plans, including the potential for walkout lower levels designed to maximize both views and indoor-outdoor living. Whether your vision is a private family compound, an equestrian estate, a multigenerational retreat, or a thoughtfully designed development opportunity, the rare combination of substantial acreage, waterfront, open fields, and lake views offers possibilities that are nearly impossible to replicate in today's market. This is a property meant to be cherished, shaped by its next steward, and enjoyed for generations to come. Adding to its appeal is the location itself. Welcome to Wolfeboro, often regarded as one of New England's most charming villages. Here, you'll find the perfect balance of peace and privacy while remaining just minutes from the vibrant downtown, with its boutique shops, restaurants, marinas, and year-round community events. Governor Wentworth Regional Carpenter Elementary Kingswood Regional High School Kingswood Regional Middle 1 NH 1781913600 1 N. Main 606 and 607 Cabin Cape Log 1781977990 https://drive.google.com/file/d/1dZYQSlCv76L2jrsryFRPjDNsOU3osMOw/view?usp=sharing Beach Access Deep Water Access Directly Adjoining Dock Access Yes Lake Winnipesaukee No Lake Yes 1 Exclusively Owned 1812 03894 ListPrice 9800000 1781968990 9800000 ListingStatus Active 1781968990 Active https://s3.us-central-1.wasabisys.com/apiv1.photos.master/3ea7-5095854-1-neren3.jpg 1 1781978038 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/7659-5095854-2-neren3.jpg 2 1781978038 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/9339-5095854-3-neren3.jpg 3 1781978038 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/7618-5095854-4-neren3.jpg 4 1781978038 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/0451-5095854-5-neren3.jpg 5 1781978038 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/e784-5095854-6-neren3.jpg 6 1781978038 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/0ba2-5095854-7-neren3.jpg 7 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https://s3.us-central-1.wasabisys.com/apiv1.photos.master/8bc2-5095854-58-neren3.jpg 58 1781978038 1781978038 1781978086 Point -71.2547535 43.6080062 RETS https://tour.primemls.com/606-and-607-N-Main-Street-Wolfeboro-NH-03894/unbranded20 WYMAN, Wolfeboro, NH 03894
MLS #5086004
City:Wolfeboro, State:NH
Price: $10950000
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 regionâs 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. Select imagery has been thoughtfully enhanced to illustrate the homeâs potential with refined updates. 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, caretakerâs 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 chefâs 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 Hampshireâs most storied lakes. By appointment. 69f2458634e2b5bcd51fd6a3 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 69f2450f34e2b5bcc13078b2 1 1 1 1 1779459077 1777484904 10950000 Jamieson Duston 5086004 Active Lake View Walking Trails Water View Wooded 270072 5086004 6096 20 WYMAN, Wolfeboro, NH 03894 1779459080 Cell: 603-365-5848 Duston Leddy Real Estate 45 1766129 740 Single Family Homes Residential 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 regionâs 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. Select imagery has been thoughtfully enhanced to illustrate the homeâs potential with refined updates. 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, caretakerâs 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 chefâs 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 Hampshireâs most storied lakes. By appointment. Dead End Private Governor Wentworth Regional Carpenter Elementary Kingswood Regional High School Kingswood Regional Middle NH 1777420800 2 WYMAN 20 Modern Architecture Bed and Breakfast Residential 1779459790 https://vimeo.com/reviews/6facb1ce-c731-415c-b0a4-9cbc92e7c237/videos/838055833 Deep Water Access Directly Adjoining Yes Lake Winnipesaukee No Lake 430 Yes 1 Exclusively Owned 2005 03894 ListPrice 10950000 1777485190 10950000 ListingStatus Active 1777485190 Active https://s3.us-central-1.wasabisys.com/apiv1.photos.master/8f95-5086004-1-neren3.jpg 1 1779459858 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/6cbd-5086004-2-neren3.jpg 2 1779459858 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/ead0-5086004-3-neren3.jpg 3 1779459858 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/20ce-5086004-4-neren3.jpg 4 1779459858 https://s3.us-central-1.wasabisys.com/apiv1.photos.master/ecb2-5086004-5-neren3.jpg 5 1779459858 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1779459926 43.5758619 -71.2518205 Point -71.2518205 43.5758619 RETS https://tour.primemls.com/20-WYMAN-Drive-Wolfeboro-NH-03894/unbranded
