Wolfeboro NH Historical Real Estate, Homes for Sale

Just ten minutes from Lake Winnipesaukee and the vibrant lakeside village of Wolfeboro, lies a remarkable property where over two centuries of New England history has been thoughtfully preserved. This 1812 three bedroom (plus bonus room) and 3.5 bathroom residence offers a rare opportunity to own one of Wolfeboro's defining country properties. Surrounded by 8.47 private acres, the home gracefully blends authentic period craftsmanship with thoughtful modern updates. Wide pine floors, hand hewn beams, 5 original fireplaces, and centuries old architectural details reflect its heritage, while a substantial addition introduces soaring ceilings, sun filled gathering spaces, and a beautifully appointed Chef’s kitchen featuring Wolf appliances and Bosch refrigeration and dishwasher. Recent improvements, including: Andersen replacement windows, updated electrical, plumbing, insulation, generator and water filtration, provide modern reliability while respecting the home's historic character. The home features a spacious primary suite with a fireplace and flexible bonus space. A second suite with a deck overlooking the pool provides guests with comfort and privacy. Outside, mature gardens, newly planted peach trees, expansive lawns, an in ground heated pool, hot tub, 2 screened porches, and exceptional privacy create a setting that feels worlds away from everyday life. The Cotton Valley Rail Trail borders the property, offering 12 miles of year-round recreation for walking, cycling, horseback riding, cross-country skiing, and snowmobiling. The crystal clear waters of Lake Winnipesaukee, golf courses, hiking trails, ski mountains, and the charm of downtown Wolfeboro remain only minutes away. Rich in history, beautifully maintained, and thoughtfully enhanced for modern living, 324 Cotton Valley Road offers a rare opportunity to own one of New Hampshire's most memorable country estates. Open House Saturday, Aug. 1 from 11-1:00.

324 Cotton Valley Rd, Wolfeboro

$850,000

3 Beds ⋅ 3 Baths ⋅ 5101491 MLS

Welcome to this beautifully reimagined home in the heart of Wolfeboro, proudly known as America's oldest summer resort. Ideally located within walking distance of historic downtown, you'll enjoy easy access to charming boutiques, local restaurants, parks, and the public docks along the shores of beautiful Lake Winnipesaukee. Completely rebuilt in 2022, this exceptional home offers the peace of mind that comes with extensive updates, including new electrical, plumbing, insulation, siding, roof, kitchen, bathrooms and a spacious 24' x 24' garage. Thoughtfully designed with quality craftmanship throughout, the home features abundant natural light, custom cabinetry, a cozy window seat, and a beautiful bay window that creates a warm and inviting atmosphere. First floor primary bedroom with ensuite bath, powder room with laundry for convenience. The second floor offers two comfortable bedrooms and a full bathroom, while the newly finished lower level (completed in 2026) significantly expands the living space. Designed for both comfort and funtionality, the lower level includes custom cabinetry, luxury vinyl plank flooring, a new HVAC system with integrated dehumidifier, and a new egress doghouse with exterior stairs, providing flexibility for guests, a home office, recreation space, or additional living quarters. Additional improvements include Drylok waterproofing, foam insulation, a perimeter drain system, and a monitored sump pump for added confidence and year round comfort. Whether you're searching for a full-time residence, a weekend getaway, or an investment opportunity in one of New Hampshire's most sought-after lake communities, this turnkey property is ready to enjoy from day one.

25 Old Lakeview Ter, Wolfeboro

$695,000

3 Beds ⋅ 2 Baths ⋅ 5101120 MLS

Nestled on a quiet side street in the heart of downtown Wolfeboro, 5 Brummitt Court, a beautifully renovated 2,316 square foot home offers the rare combination of Main Street convenience and exceptional privacy. Just moments from Brewster Academy, Lake Winnipesaukee, shops, restaurants, and the town docks, this property places you in the center of everything while providing a peaceful retreat to come home to. Set on a 0.22-acre lot, the home features three bedrooms and a bonus space on the second floor, one and a half bathrooms, a two-car garage, and a private garden and patio space, creating the perfect canvas for outdoor dining, gardening, or simply enjoying a quiet afternoon. Inside, thoughtful updates blend seamlessly with timeless character. The beautifully renovated kitchen, equipped with brand new plumbing and appliances, is complemented by completely redone bathrooms. There is hardwood and slate flooring throughout, and a spacious sunroom that opens into the home's inviting entertaining space. The sunny dining room, complete with built-in shelving, is ideal for hosting family and friends, while the bright living room and classic foyer create a warm and welcoming first impression. Extensive recent improvements provide peace of mind for years to come, including a new boiler with central air conditioning, water heater, oil tank, and a sewer line. 5 Brummitt Court also enjoys deed vehicular access from Main Street through the Pickering House security gate. Whether you're looking for a primary home in the heart of the Oldest Summer Resort in America, a vacation home, or an investment property, this classic hidden gem is not to be missed! Open House Saturday, July 25, from 10-1.

5 Brummitt Ct, Wolfeboro

$548,000

3 Beds ⋅ 2 Baths ⋅ 5101092 MLS

Welcome to 506 N Main Street, Wolfeboro, NH, where the ease of single-level living meets modern comfort and timeless New England charm. This thoughtfully designed home features an open floor plan with vaulted ceilings, beautiful wood floors, a spacious kitchen, and an inviting living room centered around a wood-burning fireplace with a classic brick hearth. The bright, year-round sunporch creates the perfect space to relax in every season and opens to a private back deck, ideal for enjoying the sunshine and surrounding gardens. The attached two-car garage offers direct entry into the home, while the full basement provides abundant storage and workspace. Newer windows and a newer roof add peace of mind. There are two contiguous parcels provide additional space and privacy. Established perennial gardens offer a succession of blooms throughout the growing season. Located less than five minutes from downtown Wolfeboro and Carry Beach on Lake Winnipesaukee you'll enjoy convenient access to the public beach, boating, shopping, dining, hiking, skiing, and the many recreational opportunities the Lakes Region is known for. Whether you're looking for a primary residence or a four-season getaway, this home offers the perfect combination of comfort, convenience, and classic Wolfeboro living.

506 N Main St, Wolfeboro

$7,395,000

4 Beds ⋅ 4 Baths ⋅ 5101021 MLS

Rare Sewall Road Offering... One of the largest waterfront lots on Sewall Road 1.57 acres in one of the most coveted addresses on Lake Winnipesaukee. This prime parcel enjoys a sunny eastern exposure, town water and sewer, and 188 feet of pristine shoreline overlooking downtown Wolfeboro, the Brewster Academy campus, and the mountains beyond. Wolfeboro has earned its title as the "Oldest Summer Resort in America" a legacy dating to 1771, when Colonial Governor John Wentworth built his summer estate on the shores of nearby Lake Wentworth. That tradition of lakeside retreat took root and flourished over the following century and a half, drawing prominent Boston and NY area families who built the shingle-style "camps" and grand cottages that still line the water today. Many of the area's most storied waterfront estates began exactly this way. Modest family camps, over generations, gave way to the refined lakefront residences the region is now known for. Your legacy begins here at 180 Sewall, on one of the area's most sought-after shorelines on the lake, within walking distance of downtown and the Sewall Woods Conservation area. This property is historically known as "Wiscasset" and was owned by the late Rev. A Edwin Keigwin who held Sunday Vespar services on the shoreline in the early 1900's. The same sheltered waterfront, deep water docking and sweeping views that have welcomed generations continue to set the stage for Lake Winnipesaukee memories. This offering includes the existing land and buildings "as is", plus newly completed and NH-approved plans and permits for a stately 9,000-square-foot Lake Compound, featuring a main house, guest house, deep-water boathouse, barn, garage, warming pool, elegant patios and hardscape. All recently approved by the State of New Hampshire. Build your dream home in one of Wolfeboro's most iconic and historic settings. This will be one of the nicest homes on the lake in one of the most desirable areas on Lake Winnipesaukee.

180 Sewall Rd, Wolfeboro

$519,000

2 Beds ⋅ 3 Baths ⋅ 5100784 MLS

End-Unit Condo Offering Privacy & Modern Luxury Near Downtown! Discover the perfect blend of comfort, style, and convenience in this meticulously maintained end-unit condo. Nestled in a prime location, this residence offers an exceptional level of privacy while remaining just moments from downtown Wolfeboro and 1 mile to the town beach. Step inside to experience an open-concept living space highlighted by stunning cathedral ceilings and warm, gleaming hardwood floors. The heart of the home features a beautiful stone fireplace, serving as the perfect focal point for cozy evenings. The primary suite has been thoughtfully renovated to include a beautiful, updated bathroom, providing a true sanctuary to unwind. Additional amenities include the convenience of a dedicated 1-car garage and access to a sparkling in-ground pool. With its seamless mix of modern updates and desirable layout, this property is ready for you to move in and enjoy a lifestyle of ease and sophistication.

4 Farmhouse Ln, Wolfeboro

$589,000

3 Beds ⋅ 2 Baths ⋅ 5100780 MLS

Your peaceful getaway awaits! This beautiful quiet and serene renovated historical home is located in the Kehonka Hill Development. Located on the south side of town just 5 minutes from downtown Wolfeboro, this peaceful spot enjoys 24 shared and landscaped acres with just 8 other houses. Enjoy the outdoors on the covered wrap around porch overlooking the backyard and campfires! Inside we have a light and bright kitchen that leads into the dining room. A wood stove gives comfort and warmth to the living room and main downstairs areas. There is a flex space just off the living room, currently used as an overflow room, but is perfect for a home office. Upstairs there are 3 bedrooms and a full bathroom with a clawfoot shower tub. The newly renovated finished basement could be used for all sorts of purposes, either a family room, a work out space, a playroom or additional weather tight storage. The backyard is perfect for entertainment and gatherings! Outside you will also find an oversized one car garage with pull down stairs to storage above. Kehonka Hill is also located in close walking distance proximity to Knights Pond with miles of walking trails to enjoy. Come see this special property today! Open House is Saturday, July 18th from 12pm-2pm!

2 Kehonka Hill Rd, Wolfeboro

$549,900

3 Beds ⋅ 2 Baths ⋅ 5099872 MLS

Charming 2BR and finished living area below with just 1 mile from downtown Wolfeboro and Lake Winnipesaukee. Updated kitchen with butcher block counters, modern cabinets, all new appliances, new lighting fixtures, new tiled bath, living room with hardwood and wood fireplace with hearth. Two bedrooms up with attached garage. Downstairs in expansive walkout basement is separate living space with wood stove, summer kitchen, work area and still rooms expand. Home offers town water, private septic and low cost Wolfeboro electric. Easy-care private backyard perfect for gardening or relaxing. Situated in desirable Wolfeboro with rights to public docks, boat launch and close to Lake Wentworth, Carry Beach and Lake Winnipesaukee for year round enjoyment.

519 N Main St, Wolfeboro

$589,000

3 Beds ⋅ 2 Baths ⋅ 5099863 MLS

Your peaceful getaway awaits! This beautiful quiet and serene renovated historical home is located in the Kehonka Hill Development. Located on the south side of town just 5 minutes from downtown Wolfeboro, this peaceful spot enjoys 24 shared and landscaped acres with just 8 other houses. Enjoy the outdoors on the covered wrap around porch overlooking the backyard and campfires! Inside we have a light and bright kitchen that leads into the dining room. A wood stove gives comfort and warmth to the living room and main downstairs areas. There is a flex space just off the living room, currently used as an overflow room, but is perfect for a home office. Upstairs there are 3 bedrooms and a full bathroom with a clawfoot shower tub. The newly renovated finished basement could be used for all sorts of purposes, either a family room, a work out space, a playroom or additional weather tight storage. The backyard is perfect for entertainment and gatherings! Outside you will also find an oversized one car garage with pull down stairs to storage above. Kehonka Hill is also located in close walking distance proximity to Knights Pond with miles of walking trails to enjoy. Come see this special property today! Open House is Saturday, July 18th from 12pm-2pm!

2 Kehonka Hill Rd, Wolfeboro

$875,000

4 Beds ⋅ 2 Baths ⋅ 5099338 MLS

This c1820 4Bdrm/2Bath Ctr Chimney Federal on 14 Acres (half Pasture & half Woodlot) abuts an 87-Acre Conservation lot in an area of other late 18th and early-to-mid 19th century homes. Built for Dr. Thomas J. Tebbetts (N Wolfeboro's earliest physician) this home was possibly started a few years earlier, as his grandfather Jonathan (who fought FOR the British in the "French & Indian" wars and AGAINST the Brits in the Revolution!) owned the land from 1807 (& their descendents stayed until 1914) The current owners' Grandparents purchased this home in 1928, with its attached 50x20 Woodshed. The c1985 rebuilt Ctr Chimney makes the 5 original fireplaces safer while the 24x30 2 story Barn & 24x30 2-car Garage provide multiple work & storage spaces. Hannafords, Walgreens, Tractor Supply, Dunkin, etc. at the intersection of Rtes 28 & 16, and an easy 1-hour commute N to the WHITE MOUNTAINS or S to the SEACOAST, are only 10 minutes away. Meanwhile it's <15 minutes to Wolfeboro's Historic Lakeside Downtown w/Town Beaches on Lakes Wentworth & Winnipesaukee, Shopping, Restaurants, updated Library & Public Safety complex, as well as our upgraded (& award-winning) Huggins Hospital. Families will also enjoy "The Nick" Recreation Park, the multi-use 12-mile (downtown to Wakefield) Cotton Valley Rail Trail and the 5 well-regarded K-12 Governor Wentworth/Kingswood Schools, (including the Lakes Region Tech Center). While ready for immediate occupancy, most folks will probably want to upgrade the Kitchen sooner rather than later. However both bathrooms, the 2 new rooms on the 3rd floor & the 4-Bedroom Septic System were all completed in last couple of decades. If you are looking for a quality Wolfeboro home with attached out-buildings, a large yard (including a 14x10 Sap House & a 20x12 "3-sided run-in" for the horse/s) and space for Gardening and/or family Farming with an attached Woodlot, this stonewall-bounded property may be for you. (See the 3 Floor PLANS in Documents.)

21 Trask Mountain Rd, Wolfeboro

$575,000

3 Beds ⋅ 2 Baths ⋅ 5099090 MLS

This home features a to-the-studs renovation transforming a dated property into a brand-new home. This extensive process stripped the structure to its skeleton, allowing for modern infrastructure, enhanced energy efficiency, and completely customized contemporary floor plan. New electrical, plumbing, insulation, roofing, siding, wallboard, Kitchen, baths, decking, entry doors and new kitchen appliances! Walk to the Wolfeboro Boat Launch, a short drive to the Wolfeboro Beaches. Visit the many fine restaurants and shops in town! Available to show Immediately and ready for Immediate Oc

5 Robin Acres Dr, Wolfeboro

$820,000

5 Beds ⋅ 3 Baths ⋅ 5097338 MLS

Fantastic location within walking distance to downtown, docks, parks, restaurants and shopping. Short drive to many private town sandy beaches including Brewster Beach over seen by Wolfeboro Parks & Recreation. This tastefully updated home can easily be an investment property or family compound. 5+ bedrooms 2.5 baths, cozy sitting areas inside and outside. The cook of the family will love the well thought out kitchen, with 2 cookstoves, abundance of counter space, dovetail drawers and plenty of cabinet space. Room for a 1st floor bedroom if you choose, and still plenty of bedrooms upstairs, Buderus Boiler with 5 heat zones to keep everyone comfortable. Relax on the covered porch or covered patio with room to expand above if you find yourself in need of more space. Wolfeboro is one of New England's oldest resort community's. Abundance of recreation opportunities, Loon Mountain 1hr 20 mins., Gunstock Ski Area 40 mins, King Pine 40 mins, Albee Beach 10 mins, Brewster Beach 6 mins, Carry Beach 4 mins, plus the Cotton Valley Rail Trail downtown. Showings start at OPEN HOUSE JULY 5TH 12- 3PM

146 N Main St, Wolfeboro

$1,900,000

3 Beds ⋅ 1 Baths ⋅ 5095867 MLS

**606 North Main Street, Wolfeboro, NH** A rare opportunity to own one of Wolfeboro's historic treasures. This remarkable 20-acre parcel is believed to be one of the original homesteads of the seven founding settlers of Wolfeboro, offering a rich connection to the town's early heritage. The property features an antique farmhouse that is likely best suited for redevelopment, allowing the next owner to create a new vision while honoring the property's historic roots. The land itself is exceptional—comprised of open fields and gently rolling terrain that is ideal for agricultural use, equestrian pursuits, or a potential subdivision opportunity, subject to local approvals. Peaceful and private, yet just minutes from downtown Wolfeboro, Lake Winnipesaukee, shopping, dining, and all the amenities that make "America's Oldest Summer Resort" so desirable, this property presents a truly unique blend of history, natural beauty, and future potential. Whether you're seeking a legacy estate, a farm, or a development opportunity, 606 North Main Street offers endless possibilities in one of New Hampshire's most sought-after communities.

607 N Main St, Wolfeboro

$9,800,000

3 Beds ⋅ 1 Baths ⋅ 5095854 MLS

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.

606 And 607 N Main St, Wolfeboro

$7,900,000

5 Beds ⋅ 1 Baths ⋅ 5095851 MLS

A truly rare offering on the shores of Winter Harbor, this remarkable 20 acre property presents a once-in-a-generation opportunity to own one of the most extraordinary waterfront estates in Wolfeboro. Comprised of one 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. 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, or a multigenerational retreat, or a thoughtfully designed development opportunity, the rare combination of substantial acreage, waterfront, 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.

606 N Main St, Wolfeboro

$665,000

3 Beds ⋅ 2 Baths ⋅ 5095502 MLS

Opportunity knocks! Located at 16 Depot St in downtown Wolfeboro, this property is ready for your residential downtown living dreams! While this has most recently been used for offices, single family uses are a permissible use in the C1 zoning district, and residential conversion of this property for residential use is subject to applicable Town of Wolfeboro regulations and inspections. The seller has obtained licensed architectural renderings showing the existing conditions as well as two proposed floor plan designs. One of the options even includes a roof top viewing deck that would overlook downtown Wolfeboro. The property has 4 deeded parking spaces on the property, with potentially room for 5 vehicles. Make an appointment to view this opportunity today! Buyer and Buyer agent are encouraged to verify residential conversion of this property with the town.

16 Depot St, Wolfeboro

$699,000

3 Beds ⋅ 3 Baths ⋅ 5095217 MLS

Imagine living within walking distance of the charming downtown Wolfeboro, in a beautifully restored historic home featuring 3 BRs, 3 BAs, attached barn/garage with views of Back Bay from the inviting sunroom. Wonderfully updated kitchen (w/ granite counters) leads into a spacious DR, with alcove perfectly suited to a home office. Front-to-back living room offers built-in shelving for your books and collections, a bath and a flexible den/optional 3rd BR rounds out the first floor. Upstairs are two generously sized bedrooms each with it's own en-suite bath. This classic Cape set on a beautiful sloping 3/4 acre lot, with frontage on both Rtes. 109 and 109A and has a fenced yard for your little ones or pets. Established trees and flowering bushes offer a sense of privacy and the Bridge Falls Rail Trail is just steps away for easy access to town, Foss Field tennis/pickleball courts/playground and even Albee Beach. Come explore this in-town gem today!

108 Center St, Wolfeboro

$519,000

2 Beds ⋅ 3 Baths ⋅ 5095131 MLS

End-Unit Condo Offering Privacy & Modern Luxury Near Downtown! Discover the perfect blend of comfort, style, and convenience in this meticulously maintained end-unit condo. Nestled in a prime location, this residence offers an exceptional level of privacy while remaining just moments from downtown Wolfeboro and 1 mile to the town beach. Step inside to experience an open-concept living space highlighted by stunning cathedral ceilings and warm, gleaming hardwood floors. The heart of the home features a beautiful stone fireplace, serving as the perfect focal point for cozy evenings. The primary suite has been thoughtfully renovated to include a beautiful, updated bathroom, providing a true sanctuary to unwind. Additional amenities include the convenience of a dedicated 1-car garage and access to a sparkling in-ground pool. With its seamless mix of modern updates and desirable layout, this property is ready for you to move in and enjoy a lifestyle of ease and sophistication.

4 Farmhouse Ln, Wolfeboro

$549,000

3 Beds ⋅ 2 Baths ⋅ 5094570 MLS

Charming 3-bedroom, 2-bath ranch set on a spacious, level lot in a convenient neighborhood within walking distance to town. Enjoy the ease of one-floor living with a bright, functional layout and a welcoming kitchen featuring granite countertops and stainless steel appliances. The relaxing sunroom overlooks the generous, fully fenced backyard, while the deck offers a natural extension for outdoor dining, relaxing, or entertaining. A large finished basement provides excellent additional living space, perfect for a family room, home office, guest overflow, or recreation area. The oversized one-car garage offers plenty of storage, and the location is hard to beat, with schools, golf, downtown shops, restaurants, and local amenities all nearby.

4 Anagance Ln, Wolfeboro

$1,825,000

5 Beds ⋅ 4 Baths ⋅ 5092835 MLS

Built in 1853 and known to generations of Wolfeboro residents as "The Varney House," this iconic Greek Revival stands as one of downtown's most recognized landmarks. The Fourth of July parade passes right by your front door, and steps from the property are charming boutiques, local restaurants, waterfront parks, and year-round community events. With easy access to scenic biking/walking trails and Lake Winnipesaukee, this exceptional property offers a lifestyle that is as active as it is relaxed. Rich with original character, wide-plank floors, natural woodwork, and 170 years of New England craftsmanship, this spacious home features 5 bedrooms and 4 bathrooms on 2 acres. The finished barn is the showpiece: soaring exposed beams, a magnificent custom stone fireplace, and a balcony overlooking the backyard. The home's energy systems are a standout: radiant floor heating, whole-home mini-splits, owned solar panels, and EV chargers in both the garage and barn modern efficiency in a historic shell. Recent upgrades including a new roof (2024), updated electrical, vinyl siding, and added insulation mean the character comes without the upkeep and a dry, insulated full basement means no surprises below grade either. Outside, an expansive composite deck with screened gazebo overlooks a beautifully maintained yard with mature fruit trees and a fenced area perfect for pets. A two-car garage, two lower barn levels, and an attached shed provide exceptional space for vehicles, tools, and toys. A landmark address in America's oldest summer resort town, this is Wolfeboro living at its finest. OPEN HOUSE SATURDAY 7/18/2026 from 10-12

153 N Main St, Wolfeboro

$2,899,900

3 Beds ⋅ 3 Baths ⋅ 5092536 MLS

A rare legacy offering on the shores of Lake Winnipesaukee. This private waterfront retreat has been cherished by the same family for over sixty-five years & represents the first lot developed on Broadside Road—one of Wolfeboro’s most exclusive lakeside enclaves. Owning 100 feet of pristine frontage, the property offers an unparalleled 180-degree panorama from Wolfeboro Bay to the east & Meredith to the west, with the Belknap Mountains rising to the south & Gunstock’s ski trails visible in the distance. The home enjoys exceptional privacy & natural protection. A paved circular driveway winds through moss-covered woodlands, encircling a wooded center island & providing ample guest parking. The centerpiece is an authentic Ward Log Cabin featuring rough-hewn logs, rich cedar interiors with polyurethane finish, a grand fieldstone fireplace, & modern upgrades including a new kitchen & bath, & updated plumbing & electrical. Highlights include a front room with an expansive picture window framing sweeping lake, island, & mountain views—ideal for watching snow-making at Gunstock. A bright three-season porch with skylights provides excellent entertaining space next to the kitchen. Additional living areas feature a second-story office with breathtaking lake views (easily convertible to a suite with wet bar), an accessible attic loft for guests, & abundant storage. Outdoor amenities shine with a King Stoneworks stone patio (perfect for a firepit), a double-railing staircase leading to a shaded lakeside platform, & a professionally built breakwater dock system complete with canopy, lighting, power, & potential jet ski lift. Meticulously landscaped grounds include stone retaining walls from Maine, perennial gardens, a Blue Spruce, window boxes, & a potting shed. Privacy is enhanced by cedar fencing & natural shrubbery, while the expansive backyard offers complete seclusion. The property is ready for immediate enjoyment.

122 Broadside Rd, Wolfeboro

$2,195,000

4 Beds ⋅ 3 Baths ⋅ 5090749 MLS

Come experience the remarkable 4,400 square foot historic Hersey Homestead! Circa 1810, with charming period features complemented by quality, modern improvements and sensitive restoration. Upgrades to the property were begun in 2025/26 and are on-going, adding to the additions made in the 1990's. Stunning, expansive luxury kitchen offers all new "chef-grade" appliances, granite counters, spacious custom island and endless cabinetry. Walk out to the masonry patio or enjoy the sunny LR with built-in entertainment shelving. In the original LR you will be welcomed by a Rumford FP with convenient gas insert, vintage beams and access to the patio. A music room and a South facing den/BR round out the first level. Upstairs are 3 additional BRs with thoughtfully re-designed baths. Warm wood flooring, crown moldings and colonial trim may be found throughout this 4 BR/3 BA stately home, with new Anderson windows, recent roof, modern septic and fresh interior/exterior paint and att. over-sized 2 car garage. Bonus space includes a large in-law/ADU with kitchenette, sep. entrance and huge storage space. Set on 10+ acres (pending sub-division) of rare open meadows with western sunset exposure, picturesque stonewalls overlooking mountain views and peek-a-boo glimpses of distant Lake Winnipesaukee. New Amish storage shed, a garden shed and original hand-hewn barn add to the opportunities of this remarkable, one-of-a-kind property. This is your chance to own a special piece of NH history! (Property is offered on 12+/- acres, subject to subdivision. Additional land available for purchase from 3 to 35 acres. Septic and new oil tank passed inspections in 2025. Seller is offering a credit of $100,000 at closing for updating the older (functional) HVAC as Buyer desires.)

580 Pine Hill Rd, Wolfeboro

$399,000

3 Beds ⋅ 1 Baths ⋅ 5088559 MLS

Welcome to this inviting three-bedroom, one-bath home ideally located just minutes from downtown Wolfeboro. Combining small-town charm with everyday convenience, this property offers easy access to local shops, restaurants, beaches, and all the attractions of the Lakes Region. Abutting the scenic Bridge Falls walking path, you can step outside and enjoy peaceful strolls, biking, and outdoor recreation right from your backyard. Whether you're searching for a year-round residence, vacation retreat, or investment opportunity, this home is the perfect place to experience the beauty, charm, and lifestyle that make Wolfeboro “The Oldest Summer Resort in America.”

133 Center St, Wolfeboro

$1,700,000

4 Beds ⋅ 5 Baths ⋅ 5086791 MLS

In the heart of Wolfeboro, 108 Whitten Neck Road is a stunning pastoral retreat that reflects the timeless character of a classic country home. Nestled right between Lake Wentworth and Crescent Lake and just moments from Wolfeboro's center where New England charm meets lake town leisure with boutique shops, restaurants, town docks, and a vibrant year-round community. This c.1788 farmhouse offers four bedrooms (plus bonus room), four and a half baths, and a striking 1810 post-and-beam barn, all set on nearly six acres of meadows and gardens. Inside, the home unfolds with the grace of another century: wide pine floors worn smooth with age, exposed beams, hand-planed paneling, and a living room where the fireplace anchors the home. The kitchen is bright with contemporary Viking appliances, the transitions are seamless, and every space feels light-filled, natural, and serene. The primary bedroom and laundry are on the main floor, offering easy living. Outside, the gardens brim with hydrangeas, clipped hedges, and fieldstone paths. Horse and walking trails lead directly from the home to nearby conservation land. The barn, with its soaring ceilings and heirloom framing, offers endless possibilities—a sculptor’s studio, a summer gathering space, or simply a vessel for decades of stories. This historic haven is a sanctuary and an invitation to live with beauty, purpose, and place in the heart of the Lakes Region.

108 Whitten Neck Rd, Wolfeboro

$668,000

4 Beds ⋅ 3 Baths ⋅ 5086059 MLS

Spacious Lakes Region Living – 4BR/3BA Condo Near Downtown Wolfeboro Welcome to your ideal New Hampshire getaway or year-round residence! This tastefully transformed 4-bedroom, 3-bath condo is perfectly situated just 1 mile from historic downtown Wolfeboro, offering the perfect blend of convenience, comfort, and charm. Step inside to find a bright and open floor plan designed for both relaxation and entertaining. The main living area features abundant natural light, a cozy fireplace, and seamless flow into the dining space and kitchen. The kitchen is well appointed with new appliances, ample cabinetry with a cozy area for casual dining, plus a bonus media room with built-ins. With four generously sized bedrooms, including a primary suite with a private bath, there’s plenty of room for family and guests. Three fully renovated bathrooms ensure comfort and privacy for everyone. Enjoy the community amenities, including a sparkling in-ground pool—perfect for summer days. Located just minutes from Wolfeboro’s charming shops, restaurants, marinas, and Lake Winnipesaukee access, this home offers the lifestyle you’ve been looking for—whether it’s boating, hiking, or simply enjoying small-town charm. Highlights: 4 Bedrooms | 3 Bathrooms Open-concept Living and Dining Area Fireplace in Living Room Charming Gas Stove Insert in Second Fireplace Community Pool 1 mile to Downtown Wolfeboro Close to Lake Winnipesaukee and Local Attractions Don’t miss this opportunity to own a piece of the Lakes Region—schedule your showing today!

1 Farm House Ln Unit 2, Wolfeboro

$725,000

3 Beds ⋅ 2 Baths ⋅ 5086026 MLS

Enjoy easy lakeside living in this renovated, stand-alone condo in Winter Harbor on Lake Winnipesaukee. This home offers the privacy of a single-family setting with the ease of shared care. The association includes a large sandy beach and southwest exposure and dock slip with this cottage. Take in sunset views from the living room or the screened porch. Inside, the home has 3 bedrooms and 2 baths. Features include a fireplace, central air, and a finished lower level with a rec room. Both the indoor and outdoor kitchens offer lake views. Located a short drive from Wolfeboro, known for its shops, dining, and small town charm. Enjoy boating, swimming, fishing, and exploring the lake this summer!

680 N Main St Unit 13, Wolfeboro

$325,000

3 Beds ⋅ 1 Baths ⋅ 5085530 MLS

Beautifully renovated and full of character, this 3-bedroom, 1 bath home has been thoughtfully updated in recent years with charming modern touches throughout. Highlights include cathedral ceilings, exposed beams, custom barn doors, gleaming wood floors, and a full daylight basement offering excellent additional potential. Set back from the road for added privacy, the property features a lovely fenced-in backyard complete with an outdoor shower, firepit, and storage shed, perfect for relaxing or entertaining. Ideally located just over a mile from Lake Wentworth’s beach and close to Nick Recreation Park, Abenaki Ski Area, Pop Whalen Ice Arena, and all the shops and dining downtown has to offer.

78 Beach Pond Rd, Wolfeboro

$695,000

3 Beds ⋅ 3 Baths ⋅ 5085498 MLS

Have you ever dreamed of living in a historic home? Take a step back in time in this thoughtfully restored 1795 Antique Center Chimney Cape in North Wolfeboro's historic “Dimon Corner.” Filled with character & steeped in history, this lovingly cared for 3 bedroom/3 bath home is absolutely stunning. A farmer’s porch greets you before you enter a large cathedral kitchen with large bespoke windows. The open kitchen has a Dacor double oven range, custom hand-built kitchen cabinets with newly painted Farrow & Ball paint, a Bosch commercial grade dishwasher, lovely exposed beams, wide plank floors & a pellet stove. Off the kitchen area is a screened-in porch for enjoying warmer days. Also on the first floor is the primary bedroom with lots of sunlight, a walk-in closet and primary bath. There is a gorgeous home office with a fireplace & a wall of built-ins. Rounding out the first floor is a very inviting den with a working fireplace and beehive oven, as well as a remodeled mudroom complete with a LG washer and dryer. The mudroom leads to a two-car garage with space above for a home gym, storage or a bonus room. The upstairs has a sunny bathroom & two charming guest bedrooms. The well landscaped property is ensconced by rock walls & has a magnificent blue stone terrace in the backyard sitting among some of Wolfeboro oldest maples trees. This tranquil sanctuary is not far from downtown Wolfeboro’s restaurants, shopping & Lake Winnipesaukee. Being sold furnished with some exceptions.

5 Trask Mountain Rd, Wolfeboro

$2,295,000

8 Beds ⋅ 7 Baths ⋅ 5084817 MLS

Historically significant 1768 Colonial with a huge 4 story Post & Beam Barn set on 4.1 +/- pastoral acres just minutes from Downtown Wolfeboro. THIS IS THE FIRST TIME OFFERED FOR SALE SINCE THE KINGS GRANT OF THE PROPERTY TO THIS FAMILY. The flexible layout of the home offers excellent opportunities for multiple uses - single family home, family compound, multi-generation living, car collector or the equestrian. The 4 story post and beam barn is an architectural site to behold with parking for up to 16 cars , the original cow stanchions are still here and even has a 2 story silo totally contained within the structure - could this be made into a climbing wall feature?? The Main portion of the home on the 1st level contains 2 Parlors with a fireplace, large Diningroom with fireplace and beehive oven, 2 Borning rooms, large fully equipped Kitchen, Familyroom with fireplace and a 1/2 bath. The second level of the main home contains 6 bedrooms and 3 bathrooms. The 3rd floor of the main home contains a bedroom, half bathroom and one of 3 attic storage areas. The 1st floor ell of the home - perfect for an in-law situation - contains a huge Livingroom with fireplace, 2 bedrooms and 2 bathrooms , one with the laundry area and 2 more attic storage areas. The grounds, with Southern exposure and distant views to the Belknap Mountains, contain a large lawn area around the home with ample area for a pool, circular driveway with a parking area for another 10 cars and approximately 3 acres of field should you desire to keep horses. Create your own utopia just minutes up the hill from Downtown Wolfeboro's restaurants, shops, marinas and Huggins Hospital. In the other direction a stroll to Carry Beach on Lake Winnipesaukee.

244 N Main St, Wolfeboro

$1,645,000

6 Beds ⋅ 4 Baths ⋅ 5083547 MLS

Grand 1840 Historic Colonial, known as "Wellsweep" in days gone by. Beautifully appointed with all contemporary conveniences yet preserved antique charm. Step inside to enjoy vintage luxury, warmth, and elegance. Private 3.2-acre setting abutting the Kingswood Golf Course. The inground pool with large pergola and private back yard porch and patio superbly complements the inviting indoor amenities. A large stately wrap-around porch is waiting for your iced tea and lemonade, so relaxing, just as the one and only Grace Kelly enjoyed right on that very porch, with a view toward the lake, hills and gorgeous sunsets! Even though situated on South Main Street, the experience once you have arrived is very private and secluded. Many substantial upgrades are listed in the Disclosure attachment, including a new 6-bedroom septic system, roof, central air, appliances, etc. totaling over $200,000. Beautiful hardwood floors throughout the first floor, formal front staircase and back servant staircase to the second floor speaks of the elegant past. Primary bedroom and ensuite with double vanity on the second floor in the rear of the house affords peace and quiet also. Detached, oversized garage with heated workshop. Beautifully maintained grounds with stately, mature trees. Minutes to private town, resident only beaches on Lake Winnipesaukee, marinas, fine dining, skiing, and all that Wolfeboro and the Lakes Region has to offer. OPEN HOUSE SAT 5/23 11:00 am to 2:00 PM

375 S Main St, Wolfeboro

$1,349,000

3 Beds ⋅ 3 Baths ⋅ 5081887 MLS

Set on over three acres in the heart of Wolfeboro, this stately 1897 Queen Anne Victorian, attributed to renowned architect George Barber, is a rare offering where history, character, and opportunity come together. Inside, the main house welcomes you with a gracious formal entry, double parlors, a large kitchen with formal dining room, three bedrooms, and 2.5 baths, plus an unfinished attic with potential for additional living space. Original architectural details shine throughout, from three working fireplaces to the grand turret with curved glass windows and beautifully preserved period millwork. Recent upgrades, including the addition of a full bathroom, refinished floors on the second level and stairs, mini-split systems, a new boiler, updated electrical, and fresh exterior paint, add comfort and ease while honoring the home’s enduring charm. Outside, a detached carriage house currently used for retail, a separate office, dual street frontage on Center and Willow, and Limited Business District zoning open the door to a range of future possibilities. Just steps from the Cotton Valley Rail Trail, downtown Wolfeboro, and Winnipesaukee’s Back Bay, this is more than a historic property. It is a setting for the next chapter.

68 Center St, Wolfeboro

$499,000

3 Beds ⋅ 3 Baths ⋅ 5077690 MLS

For those who appreciate history, craftsmanship, and the satisfaction of bringing a special home back to life, this picturesque antique brick property offers an exciting opportunity in the heart of Wolfeboro. Set on three private acres, this three-bedroom home offers three baths, bonus spaces for an office, studio, or creative pursuits, and the kind of character that simply cannot be replicated. Original architectural details including barn-board ceilings, exposed beams, exposed brick, and fireplaces reflect the timeless craftsmanship of classic New England homes. Sun-filled living spaces, cozy gathering rooms, and an updated kitchen create a welcoming foundation for everyday living, while the home’s next owner has the opportunity to restore and enhance the property according to their own vision. Being sold as is and offered at new, reduced price, this is a chance to invest in a home with built-in potential—and ultimately reap the rewards of the work you put into it. Outside, the expansive grounds offer privacy, mature perennial gardens, and plenty of room to enjoy the outdoors. A tree house adds a touch of whimsy for the young at heart, while the outbuilding provides additional storage and the detached two-car garage adds convenience. Located near Routes 28 and 109 for easy travel north or south, the property is also close to Fernald Station, The Nick, Huggins Hospital, local beaches, and lake access. With its historic character, generous acreage, desirable Wolfeboro location, and opportunity to create something truly special, this is a rare chance to own a Lakes Region home where the right vision—and the work to bring it forward can pay off in a big way.

11 N Line Rd, Wolfeboro

$699,000

3 Beds ⋅ 4 Baths ⋅ 5034913 MLS

Welcome to Twin Eagle Farm: an exquisite NE Cape, originally built circa 1812, featuring the very best updates and amenities sought after in 2026. Highlights include 3 BRs, each with its' own custom tiled, spa bath. Primary suite on the first floor, for ease of living at any stage of life, and 2 gracious BRs on the upper level. You will also appreciate the versatile den/library/office, and the dedicated laundry room, along with a full bath on the first floor. The well-appointed kitchen is ready for all of your culinary adventures with high-end appliances, plenty of cabinet space, beautiful French flooring, spacious dining area and direct access to both the deck for grilling & relaxing as well as the pocket garden, perfect for growing your own herbs. The striking cabinet color and beautiful counters are complimented by warm wood details and original exposed beams blending the best of old and new. The large, wood-burning fireplace in the LR will the take chill off the cooler months. Throughout the home the thoughtful upgrades include high-efficiency ANDERSON WINDOWS, new central A/C and true attention to detail. The home is now offered on 4 acres, with potential for future subdivision of a 2 acre lot. Bonus features include a small, 3 level storage barn and a pad ready to build your future shed or garage. Convenient to downtown Wolfeboro, lake activities, beaches, schools and medical ctr. Truly a one-of-a-kind opportunity to live your dream life!

116 Middleton Rd, Wolfeboro

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