Wolfeboro, NH — The Oldest Summer Resort Town In America

Wolfeboro, NH — The Oldest Summer Resort Town In America

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.

Frank Roche, President of Roche Realty Group, Inc. with offices in Meredith and Laconia, NH

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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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 Wolfeboro’s finest off-lake estates—where historic craftsmanship meets contemporary luxury living. Set on 2.7 acres along the town’s 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 butler’s 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 35×25 patio — 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 18×40 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 Wolfeboro’s architectural heritage at its most graceful — 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 Wolfeboro’s finest off-lake estates—where historic craftsmanship meets contemporary luxury living. Set on 2.7 acres along the town’s 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 butler’s 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 35×25 patio — 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 18×40 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 Wolfeboro’s architectural heritage at its most graceful — 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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5A 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
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Center Harbor, New Hampshire

Center Harbor, NH: A Peaceful Getaway

I’ve always had a special fondness for Center Harbor, New Hampshire. It brings back happy ...
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Homes along Lake Winnipesaukee, a top destination for Baby Boomers in the Lakes Region.

How Boomers Are Shaping the Lakes Region Real Estate Market

Over the years, I’ve had an interest in following the Baby Boomer generation because they ...
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The Albany Covered Bridge along the Kancamagus Highway in New Hampshire’s White Mountains is surrounded by brilliant autumn foliage.

Fall Foliage Guide: New Hampshire

It’s that time of year—crisp, sunny days followed by cool nights—creating long-lasting fall colors across ...
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Lakes Region Real Estate – Fall Market Trends and Homes for Sale

Lakes Region Real Estate – Fall Market Trends

We’re almost halfway through September, and a friend of mine indicated the leaves are starting ...
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AI's Impact on the future of real estate

AI in Real Estate: What Buyers and Sellers Need to Know

How AI is Changing the Real Estate Market: A Look Back and Ahead A Personal ...
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Lake Winnipesaukee in New Hampshire's Lakes Region

Labor Day Market Update: Real Estate Trends in New Hampshire’s Lakes Region & Beyond

It’s been a great summer, and the days have flown by. Can you believe it’s ...
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Merrymeeting Lake in the Lakes Region

Protecting New Hampshire’s Lakes

We’ve had an interesting late spring and summer season this year with lots of weekend ...
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Buy Versus Rent in the Lakes Region

Buy Versus Rent in the Lakes Region

In the Lakes Region, and I’m sure everywhere in New Hampshire, the big question of ...
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Windward Harbor on Lake Winnipesaukee in Moultonborough, NH

Lakes Region Communities Developed in the 1980s

When you drive around the Lake Region this summer, you will notice a considerable number ...
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Bear Island is the 2nd largest island with 780 acres on Lake Winnipesaukee

Lake Winnipesaukee Island Living

This past week and a half delivered nice, hot, humid weather to the Lakes Region. ...
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Merrymeeting Lake in New Durham, New Hampshire

New Hampshire Ranked #1 Best State to Retire in 2025 — Here’s Why

Some really interesting news just hit the airwaves regarding New Hampshire. A report just published ...
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Real Estate Scams

Property Owners Beware of Real Estate Scams

I was listening to the radio recently, where it reported the FBI in Boston noted ...
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New Hampshire Housing Market Sees 65 Straight Months of Growth

New Hampshire Housing Market Sees 65 Straight Months of Growth

New Hampshire’s Median Home Sales Price Hits New Record It was announced this week by ...
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Peaks of New England

Exploring the Peaks of New Hampshire, Maine & Vermont

In my younger years in school, I always loved geography. Living in New Hampshire, there ...
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Mount Washington, New Hampshire

30 Reasons Why New Hampshire Stands Out!

With lakes, beaches, mountains, forests, rivers, and the ocean for people who enjoy the outdoors, ...
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Lakes Region Real Estate Comparisons Year-to-Date

Lakes Region Real Estate Market Snapshot

We’re entering the peak of the selling season here in New Hampshire’s beautiful Lakes Region. ...
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Home improvements

2025 Home Improvements That Pay Off in the Lakes Region Real Estate Market

Over the past year, I’ve had many conversations with clients, friends, and neighbors throughout the ...
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at Suissevale, there are approximately 426 year-round homes spread out on over 600 acres with 2,500’ of shorefront on Winnipesaukee with sandy beaches, a marina, clubhouse, and other amenities.

Strong Demand for Water Access Communities in the Lakes Region

One of our Realtors at Roche Realty Group received a call the other day from ...
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Sleeper Island on Lake Winnipesaukee currently has one island waterfront property for sale

5-Month Lakes Region Waterfront Sales Comparison

We are five months into our Lakes Region Real Estate Market for 2025. I thought ...
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Views along The Marginal Way in Ogunquit, Maine.

NH Lakes Region vs. Coast of Maine

Over the years, I’ve met many families thinking of purchasing a second home, and they ...
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Yacht Club Vista on Lake Winnipesaukee, Gilford, NH

Yacht Club Vista on Lake Winnipesaukee: A Boater’s Paradise

When you are navigating the shores of Lake Winnipesaukee, there are many water-access communities to ...
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Best State To Live In — New Hampshire at #3

New Hampshire Ranked #2 Best State for 2025

When you live in a state like New Hampshire, it’s always a good feeling to ...
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Jonathan's Landing

5-Year Sales Activity at Jonathan’s Landing on Lake Winnipesaukee

When you navigate the shores of Lake Winnipesaukee, there are 71 square miles of water ...
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The Grouse Point Club, Lake Winnipesaukee, NH

The Grouse Point Club on Lake Winnipesaukee: What’s Trending?

With 71 square miles of sparkling water and 274 islands to meander through, Lake Winnipesaukee ...
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Land's End on Lake Winnipesaukee in Moultonborough, NH

5-Year Sales Activity at Lands End on Lake Winnipesaukee

As you explore the shores of Lake Winnipesaukee, there are 72 square miles of water ...
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Northfield, New Hampshire

Investing in Northfield, NH: Real Estate Market and Trends

Northfield is a charming small town nestled along the Winnipesaukee River. Originally part of Canterbury, ...
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Aerial view of Lake Winnisquam and Sanbornton, New Hampshire

Lake Winnisquam Popularity is Always Increasing

There are literally 273 lakes, ponds, and rivers to enjoy in New Hampshire’s Lakes Region. ...
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Gilford, New Hampshire on Lake Winnipesaukee

Gilford vs. Meredith: Which Lakeside Gem Fits Your Lifestyle?

There are 25 towns and cities comprising the Lakes Region. This week, I thought I ...
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Lakes Region Real Estate Comparisons Year-to-Date

Lakes Region Real Estate Comparisons Year-to-Date

I thought I would take a look at our local real estate market and see ...
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Merrymeeting Lake New Durham

Four Years of Sales Activity at Merrymeeting Lake

Merrymeeting Lake is one of the most desirable lakes in New Hampshire, known for its ...
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Moultonborough’s Attraction and Waterfront Sales Activity

Moultonborough’s Attraction and Waterfront Sales Activity

There’s a wide selection of communities to consider when purchasing in New Hampshire’s Lakes Region. ...
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13 Spring Home Maintenance Tips for Homeowners

13 Spring Home Maintenance Tips for Homeowners

I’ve never seen the snow melt so fast in the Lakes Region. As warmer weather ...
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Five Years of Sales Activity at Samoset Condominiums

Samoset Condominium: A Five-Year Sales Market Overview

For individuals looking for an attractive water access community on the “Big Lake,” Samoset Condominiums ...
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Robust Commercial Sales Activity Over the Past Four Years

Robust Commercial Sales Activity Over Four Years

In the Lakes Region, we have seen an uptick in commercial sales activity over the ...
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