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$1,500,000
4 Beds 5 Baths 5088361 MLS
Experience the Wolfeboro lifestyle with the space, privacy, and flexibility that are increasingly difficult to find. Set on 2.81 private acres just minutes from downtown, 151 Ambrose Way offers nearly 5,000 square feet of thoughtfully designed living space with an adaptable layout ideal for year-round living, extended guests, multigenerational needs, work-from-home space, and recreation. The backyard is a true retreat, featuring a heated pool, patio, and private sand area that creates a beach-like setting at home. The property also offers access to adjoining town-owned land connecting to scenic walking, biking, and cross-country ski trails, including a wooded path leading toward downtown Wolfeboro. Seasonal lake and mountain views add to the setting. Inside are four bedrooms, four and a half baths, expansive gathering spaces, and multiple areas that can evolve with a buyer’s lifestyle. The great room features a striking stone gas fireplace, while the chef’s kitchen offers maple cabinetry, high-end appliances, two ovens, and generous entertaining space. Additional living and recreation areas provide flexibility for guests, fitness, media, hobbies, or extended stays. A three-car attached garage includes an oversized bay ideal for boat or RV storage. Additional comforts include central air, Mitsubishi heat pumps, and a whole-house generator. Just minutes from Wolfeboro’s restaurants, galleries, boutiques, town docks, and waterfront activity, this property offers a compelling alternative for buyers seeking the Lakes Region lifestyle with more space, privacy, and amenities than direct waterfront often provides. Virtually staged/AI-modified images illustrate the potential of several spaces; original photos are included for comparison. Showings by confirmed appointment only.

151 Ambrose Way, 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

$10,950,000
7 Beds 8 Baths 5086004 MLS
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 region’s 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. 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, caretaker’s 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 chef’s 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 Hampshire’s most storied lakes. By appointment.

20 Wyman Dr, Wolfeboro

$665,000
3 Beds 3 Baths 5085895 MLS
Now offered at a reduced price, giving buyers added flexibility to make their own cosmetic updates! Tucked into Robin Acres, an established neighborhood off North Main Street, this gambrel offers something genuinely hard to find: a true first floor primary suite with a double vanity bath and ample closet space, making one level living a real option rather than an afterthought. The main level centers around a spacious 17 by 27 living room, along with a separate family room, formal dining room with a bay window, and a kitchen that opens directly to the attached garage. First floor laundry and a full guest bath round out the main level. The living room also features a convenient built in mini bar, positioned just steps from the 33 foot screened porch overlooking the backyard. The porch connects through to the family room, which flows into the kitchen, creating a natural loop for entertaining. It is an ideal setting for three season gatherings, lazy summer mornings, and quiet evenings with the windows open. Hardwood floors extend throughout the main living areas. Upstairs, two oversized bedrooms stretch close to 18 feet long and offer generous closet space. A full bath, central hall, and flexible bonus room provide additional options for a home office, guest space, nursery, or hobby room. The full basement adds workshop space, storage, and future finishing potential. Located just five minutes from downtown Wolfeboro, where dining and shopping surround Wolfeboro Bay, including Bailey's Bubble, Garwoods, Downtown Grill, Wolfe's Tavern at the Wolfeboro Inn, and free summer concerts at Cate Park. The Cotton Valley Rail Trail runs from downtown toward Wakefield, while Lake Winnipesaukee public access is right down the road. Lake Wentworth and Crescent Lake are also both within town limits. Enjoy easy access to downtown, three lakes, four season recreation, and everything that makes Wolfeboro a true year round Lakes Region community.

11 Robin Acres Dr, 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

$3,795,000
3 Beds 3 Baths 5083555 MLS
Set along the shores of Lake Winnipesaukee in desirable Wolfeboro, 9 Umbrella Point offers 250 feet of exceptional waterfront and sweeping sunset views across the lake toward Gunstock Mountain and Rattlesnake Island. This well-maintained home is designed for true single-level living, featuring a wide-open floor plan and large windows that bring in natural light and showcase the water from nearly every room. A fantastic study upstairs offers a peaceful retreat with stunning lake views—ideal for working from home or unwinding with a good book. The seamless flow between living spaces makes the home feel both comfortable and ideal for entertaining. Outside, the yard is level and inviting, with stairs leading down to the water’s edge. A brand-new dock accommodates two boats with ease, making it simple to enjoy everything lake life has to offer. Whether you’re relaxing on the deck, gathering by the shoreline, or heading out on the water, the setting is both functional and picturesque. Additional features include a two-car attached garage and a separate three-car garage, perfect for storing boats, watercraft, and recreational gear. Located in a quiet, private association just off Forest Road, this property offers a sense of seclusion while remaining just minutes from downtown Wolfeboro’s shops, dining, and amenities. An outstanding opportunity to enjoy turnkey waterfront living in the heart of the Lakes Region.

9 Umbrella Pt, 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

$385,000
3 Beds 2 Baths 5082831 MLS
Welcome to 9 Hemlock Drive in Wolfeboro, NH...an inviting opportunity to own a spacious home in one of the Lakes Region’s most desirable towns. Offering over 2,700 square feet of living space, this 3-bedroom, 2-bathroom property is set on a generous 1.93 lot, providing both privacy and room to enjoy the outdoors. The property also offers a 2 year old roof and generator hook up for peace of mind. Designed for convenient one-level living, the home features a functional layout ideal for a variety of lifestyles. The bright and airy sunroom is a standout space, perfect for relaxing with a morning coffee or enjoying the natural surroundings year-round. The living room has been updated with brand new carpeting, adding comfort and a fresh touch. This home also presents a great opportunity for a new owner to add new updates over time and truly make it their own. A large basement offers excellent storage or the potential to be finished for additional living space, home office, or recreation area. Whether you’re looking to expand or simply need extra room, the possibilities are there. Located less than 2 miles from historic downtown Wolfeboro, you’ll have easy access to charming shops, local restaurants, grocery stores, and the beautiful shores of Lake Winnipesaukee. Affordably priced for Wolfeboro, this property presents a fantastic opportunity for first-time homebuyers, those seeking to downsize with the ease of one-level living, or investors looking for value in a prime location. Don’t miss your chance to make this versatile home your own!

9 Hemlock Dr, 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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