Lake Winnipesaukee Homes with Guest Quarters Exterior Features

Welcome to the picturesque shores of Lake Winnipesaukee, nestled in the heart of New Hampshire! Known for its breathtaking views and crystal-clear waters, Lake Winnipesaukee is a true gem of the Granite State. Spanning over 72 square miles, this stunning lake is surrounded by charming towns, lush forests, and the majestic peaks of the White Mountains, making it an ideal destination for both relaxation and adventure.

Imagine waking up to the serene sounds of nature and the gentle lapping of waves right outside your door. Homes in this enchanting area often come with incredible guest quarters, perfect for hosting family and friends. These thoughtfully designed spaces provide a comfortable retreat and ensure that your guests feel right at home while enjoying all that Lake Winnipesaukee has to offer.

With exterior features that blend seamlessly with the natural beauty of the surroundings, many properties boast expansive decks, inviting patios, and private docks, allowing you to fully embrace the lakeside lifestyle. Picture yourself sipping morning coffee while basking in the sun, or hosting lively summer barbecues as the sun sets over the water.

Whether you’re an outdoor enthusiast eager to explore hiking trails, a boating aficionado ready to navigate the lake's many islands, or simply someone looking to unwind in a tranquil setting, Lake Winnipesaukee offers it all. Discover the perfect home with guest quarters that not only provides comfort but also an opportunity to create unforgettable memories in this stunning New Hampshire paradise. Come and experience the magic of Lake Winnipesaukee for yourself!

Newest Lake Winnipesaukee Homes with Guest Quarters Exterior Features

$13,900,000

9 Beds ⋅ 11 Baths ⋅ 5108354 MLS

There is nothing like this on Lake Winnipesaukee. Offered together as a private Winter Harbor compound, 14 & 20 Gateway Road encompass approximately 3 acres +/- with approximately 370' +/- of combined waterfront, two residences, extensive docking, and a sandy walk-in beach. The centerpiece, completed in 2023, is an approximately 8,600-square-foot contemporary residence was engineered by Thornton Tomasetti. Brazilian black slate and engineered rift oak floors, solid rift oak interior doors, hand-selected natural quartzite, custom millwork, stained red cedar siding, Douglas fir porch ceilings, and IPE decking define the build. A fully integrated Control4 system governs lighting, climate, Lutron power shades, and distributed audio. An 800-amp electrical service is supported by 45 kW generator backup. Six bedrooms, six full baths, three half baths, generous gathering spaces, and multiple professional-grade kitchen and prep stations support serious entertaining. At 20 Gateway, a cantilevered steel boathouse with rooftop entertaining deck is paired with a no-profile boat lift, 50-foot aluminum Lift-A-Dock, and sandy walk-in beach. At 14 Gateway, 195 feet of Winter Harbor frontage includes expansive U-shaped covered docking with room for multiple boats and watercraft. The classic 1958 Winnipesaukee cabin at 14 Gateway sits on approximately two additional acres and offers three bedrooms, one full bath, warm wood interiors, and a broad lakeside deck. More time capsule than guest house, it provides a distinct counterpoint to the contemporary residence. This is a finished, move-in-ready Winter Harbor compound that brings together contemporary architecture, a preserved vintage lake cabin, approximately 370' +/- of waterfront, extensive boating infrastructure, and approximately 3 acres +/- in one exceptional offering. Please note all acreage, waterfrontage, sq footage, bedrooms and baths have been combined to reflect the whole compound.

14 & 20 Gateway Rd, Wolfeboro

$2,295,000

4 Beds ⋅ 4 Baths ⋅ 5108216 MLS

Soon to be one of the most luxurious island homes on Lake Winnipesaukee, this stunning 4-bedroom, 4-bathroom residence has been fully renovated throughout, creating an exceptional lakefront retreat on sought-after Bear Island. With breathtaking views of Lake Winnipesaukee and Mt. Washington, an extraordinary waterfront, and updated throughout, this is a truly special property. The waterfront is nothing short of spectacular. A clear approach leads to a dedicated swimming area, complemented by an oversized U-shaped dock.The expansive dock offers abundant space for boats, swimming, entertaining, and even the potential to accommodate a seaplane. A new waterfront deck, glass railings, and landscape lighting further enhance this exceptional setting. Inside, the home has been completely transformed with high-end finishes and meticulous attention to detail. Floor-to-ceiling windows showcase the spectacular lake and mountain views, while white pine shiplap walls, porcelain tile, LED lighting, and beautifully appointed spaces create an inviting atmosphere. The kitchen features quartz countertops and a premium Thermador appliance package. The lower level offers a second kitchen, providing flexibility for entertaining and extended stays. The primary en-suite features stunning views and a luxurious bathroom featuring a custom oversized tile shower and double vanities. Adding to the appeal is a separate seasonal log cabin cottage with a kitchenette, bathroom, and lofted sleeping area, an ideal private retreat for guests. The extensive renovation also includes a new roof, spray foam insulation, AZEK mahogany decking, composite board-and-batten siding, new electrical and plumbing, Mitsubishi Hyper-Heat heating and air conditioning, whole-house dehumidification, upgraded water filtration and more. Surrounded by the natural beauty of Bear Island State Forest and its walking trails, this is a rare opportunity to own a truly distinctive Lake Winnipesaukee property. Completion date Oct.

155 Bear Is, Meredith

$3,999,000

3 Beds ⋅ 3 Baths ⋅ 5102855 MLS

Spanning the full width of Melody Island, 2 Melody Island is a truly remarkable and one-of-a-kind Lake Winnipesaukee retreat. With approximately 315 feet of waterfront on both sides of the island, the property offers the rare opportunity to enjoy beautiful sunrises from one shoreline and spectacular long-range sunset views from the other. The property’s diverse shoreline features multiple swimming areas, including sandy beaches and a naturally formed submerged stone terrace. This distinctive in-water gathering area provides a wonderful place for swimmers to stand, sit, and relax while surrounded by the lake (an especially memorable feature for family and friends of all ages). The main residence offers three bedrooms and a spacious, open-concept living area centered around a beautiful stone fireplace. Expansive lake views bring the beauty of Winnipesaukee indoors, while comfortable gathering spaces create an inviting setting for entertaining, relaxing, and making lasting memories. A separate bunkhouse provides additional privacy and flexibility for guests, complete with its own bathroom, laundry facilities, and generous sleeping accommodations. Together, the main house and bunkhouse offer ample space to welcome extended family and friends while allowing everyone to enjoy a sense of privacy. Conveniently located just a 5 minute boat ride from Wolfeboro, Melody Island offers close proximity to shopping, dining, coffee shops, and town docks adding to the ease and enjoyment of island living. With its extraordinary shoreline, sunrise-to-sunset views, 2 Melody Island is a rare and unforgettable retreat that captures the very best of Lake Winnipesaukee island living.

2 Melody Is, Wolfeboro

$11,750,000

6 Beds ⋅ 8 Baths ⋅ 5102364 MLS

Experience the pinnacle of Lake Winnipesaukee waterfront living from this extraordinary Governor's Island estate, offering 295 feet of pristine shoreline and a rare private sandy beach on one of the lake's most coveted waterfront settings. Perfectly positioned to capture panoramic lake and mountain views, this exceptional residence features 6 bedrooms, 8 bathrooms, and timeless craftsmanship throughout. Designed for both grand entertaining and everyday living, the home showcases custom millwork, stone and iron accents, soaring ceilings, and expansive gathering spaces. Walls of glass frame breathtaking waterfront views while filling the home with natural light. A private elevator provides convenient access to every level. The gourmet chef's kitchen anchors the home and flows seamlessly into elegant living and dining areas, a private library, executive office, and thoughtfully designed guest accommodations. The luxurious primary suite offers spectacular lake views, a spa-inspired bath, and refined custom finishes. Multiple fireplaces, recreation spaces, and generous garage capacity complete the interior. Outside, enjoy expansive docking, beautifully landscaped grounds, sweeping lawns, stone patios, and exceptional outdoor living spaces designed for entertaining or quiet relaxation. The private sandy beach provides the perfect setting for swimming, launching kayaks or paddleboards, or simply enjoying the crystal-clear waters of Lake Winnipesaukee. A rare opportunity to own one of Governor's Island's premier waterfront estates, offering unmatched privacy, year-round luxury, and the very best of New Hampshire's Lakes Region lifestyle.

59 Broadview Ter, Gilford

$499,000

3 Beds ⋅ 2 Baths ⋅ 5101137 MLS

Rare opportunity to own two seasonal cottages on a private one-acre lot, just 1 minute from Moultonborough Town Beach and public boat launch. Ideal for hosting family and friends or creating your own Lakes Region retreat, this unique property offers exceptional flexibility and charm. The main cottage features two bedrooms, a three-quarter bath, an updated kitchen with an island, a comfortable living area, and a spacious deck perfect for relaxing or entertaining. The second cottage includes one bedroom, a three-quarter bath, a cozy living area, and a kitchenette, providing ideal accommodations for guests. The property also includes a garage, two storage sheds, and a covered patio with electricity, creating the perfect space for outdoor dining, grilling, and enjoying warm summer evenings. Both cottages are being conveyed partially furnished, allowing you to move in and begin enjoying the Lakes Region lifestyle immediately. Whether you're looking for a family summer compound, a weekend getaway, or a property with space for guests and convenient boating access, this one-of-a-kind offering is ready to be enjoyed.

53 Deer Run Ln, Moultonborough

$7,395,000

4 Beds ⋅ 4 Baths ⋅ 5101021 MLS

Rare Sewall Road Offering... Including 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. 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. 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

$1,995,000

2 Beds ⋅ 2 Baths ⋅ 5093923 MLS

Expansive views across Lake Winnipesaukee, islands, Ossipee & Sandwich Mountains, to include views out to Mount Washington, approximately 69 miles away. Beautiful waterfront, sandy beach with a clear sandy bottom, dockage, and Seller has approved mooring. 2 buildings of record, large enough to house the entire family or scale back to just owner's quarter; the entire property has been upgraded, remodeled inside, and out. Views from just about every room in both buildings, stainless steel appliances, and many extras throughout this property. Between the two buildings: 11 rooms, 3 baths, 2+ bedrooms, level lot easy access, septic system, drilled artesian well, northern exposure. Located in the heart of the Lakes Region, only minutes to Gunstock Ski Resort, Bank of New Hampshire Meadowbrook Concert Pavilion, shopping malls, and so much more.

36 Elm St, Alton

$5,200,000

5 Beds ⋅ 4 Baths ⋅ 5093615 MLS

A rare Lake Winnipesaukee offering, this legacy property features 300 feet of pristine waterfront and over 2.7 private acres and spectacular views, ideally situated between Meredith and Center Harbor, providing convenient access to shopping, dining, marinas, and all the attractions of the Lakes Region. Turn into the beautiful winding driveway and shortly you will be at home. Blending classic lakehouse charm with modern amenities, this inviting waterfront retreat is designed for gathering and making memories. The spacious kitchen is a chef's dream, featuring an 8-burner Viking range, walk-in pantry, wet bar, and ample space for entertaining. Multiple living areas, highlighted by two fireplaces, offer comfortable places to relax in every season, while the screened porch provides the perfect setting for morning coffee or evening dinners overlooking the lake. The main level includes a bedroom and ¾ bath, offering flexibility for guests and convenient first-floor living. Upstairs, the primary suite enjoys its own large private deck with sweeping water views, accompanied by two additional bedrooms and a full bath. Beautifully landscaped grounds lead to the waterfront, where two private docks, walk-in lake access, with sandy bottom and 300 feet of shoreline create an exceptional setting for boating, swimming, and enjoying life on the lake. An adorable bunkhouse with its own screened porch and ¾ bath provides a charming guest retreat just steps from the water. Additional features include a detached two-car garage with a screened porch and finished space above, as well as a detached barn offering abundant storage for boats, water toys, and recreational equipment. Combining exceptional privacy, extensive waterfrontage, and close proximity to everything by car or by boat, this is a unique opportunity to own a classic Lake Winnipesaukee property ready to be enjoyed for generations to come. 6 BR State approved septic.

28 Veasey Shore Rd, Meredith

$4,195,000

6 Beds ⋅ 6 Baths ⋅ 5090218 MLS

This is a rare once-in-a-generation opportunity to own an iconic waterfront compound in coveted Melvin Village on Lake Winnipesaukee. Set on 6.5 private, level acres with over 300 feet of pristine lake frontage, this extraordinary property offers a combination of scale, privacy, grandfathered waterfront structures, and future potential that is seldom available on the Lake. Sweeping southern exposure and panoramic views across Melvin Bay to the Belknap Mountains & Gunstock Mountain Resort, the setting is nothing short of spectacular. The property includes a walk-in sandy beach, permanent docks with four boat slips, all-day sun, and breathtaking sunsets throughout the year. The compound features three distinct residential structures thoughtfully designed for entertaining, hosting guests, and multi-generational living. The main residence offers 3bd and 2.5 baths, highlighted by a spacious chef’s kitchen, generous dining and gathering spaces, office, screened porch, and a first-floor primary suite. A heated 4 car garage includes a beautifully updated one-bedroom apartment above, while the grandfathered residential boathouse sits directly at the water’s edge with 2 bd, 2 baths, and nearly 180-degree water views from its unparalleled lakeside setting. Add'l amenities include a detached three-car garage, substantial boat barn storage, beautifully landscaped grounds, patio spaces, gazebo with hot tub, & exceptional room for boats, vehicles, recreational equipment, & lake-life entertaining. Equally compelling is the property’s long-term versatility. Whether enjoyed as a private family retreat, legacy estate, vacation compound, or investment opportunity, the double-lot configuration and favorable zoning may allow for future expansion or additional residential structures, creating a truly unique opportunity on one of New Hampshire’s most sought-after lakes. Seeing this property in person is the only way to fully appreciate the scale, privacy, views and lifestyle it offers.

456 Governor Wentworth Hwy, Tuftonboro

$2,399,999

2 Beds ⋅ 2 Baths ⋅ 5086131 MLS

Experience the best of Lake Winnipesaukee living in this beautifully remodeled waterfront retreat in desirable low tax Moultonborough. Perfectly positioned just 10 feet from the water, grandfathered in for a truly rare setting, this home offers an unmatched, immersive connection to the lake where it feels as though you are sitting right on top of the water. The home captures sweeping lake views from every room. Expansive windows and sliding glass doors flood the open concept living space with natural light, seamlessly bringing the beauty of the lake indoors. The spacious living area flows effortlessly to a lakeside deck, creating the perfect setting for entertaining or relaxing just steps from the shoreline. The newly added primary suite offers panoramic water views, allowing you to wake up and fall asleep to the peaceful sound of loons. The suite emcompasses the entire 2nd floor with a primary bedroom, office, walk in closet, extra sized master bathroom as well as the laundry room. The first floor consists of another 2 rooms currently used as bedrooms (2 bedroom septic). The bunkhouse offers additional sleeping quarters for extra guests. Outside, enjoy your private stretch of pristine Lake Winnipesaukee shoreline, complete with a large dock and crystal clear water with a sandy bottom and beach area. Whether boating, swimming, or simply unwinding, this property offers an incredible setting for making lasting summer memories. Extensive recent upgrades include a new mini split system, new whole house generator, new water heater, new furnace, new drilled well, all new electrical and plumbing, a new sump pump, new doors and windows, new roof, new exterior, Trex deck, updated bunkhouse exterior, and a 3 bedroom septic design plan for future expansion.

5 Fir Tree Ln, Moultonborough

$3,650,000

5082106 MLS

An iconic presence in the heart of the Lakes Region, Grand View Resort operates at full strength with consistent maximum occupancy—a testament to its reputation, premier location, and loyal guest following. This is more than a property purchase; it’s the acquisition of a thriving, turnkey hospitality business with proven performance, positioned along a high-visibility corridor with strong traffic counts between Laconia and Weirs Beach. Set on approximately 3± level acres, the immaculately maintained compound has undergone substantial renovations in recent years. The 12-unit hotel was taken down to the studs and thoughtfully rebuilt, offering the feel and efficiency of new construction while preserving classic Lakes Region charm. Two end suites feature full kitchens and private decks—perfect for sunrise coffee or golden hour lake views. The motel also includes a 2-car under garage for added convenience and operations. The 10-bedroom main house, complete with an office, offers exceptional flexibility—ideal as an owner’s suite, additional rental income, or a boutique hospitality experience with a historic bed-and-breakfast feel. The main living area showcases multi-million-dollar views of Lake Winnipesaukee, creating an unforgettable setting. Eight charming cottages and two beautifully renovated cabins blend character with modern comforts, offering a diverse mix of accommodations that keep guests returning year after year. The setting is nothing short of spectacular, with sweeping views from the Broads to Mount Chocorua and front-row seats to watch the MS Mount Washington pass by. Guests enjoy an Olympic-sized heated saltwater pool and patio overlooking lake and mountain vistas that define the New Hampshire experience. With extensive updates complete and a strong operational foundation, this is a rare opportunity to step into a flourishing business in one of the region’s most recognizable destinations—reimagined, revitalized, and ready for its next chapter.

291 N Endicott St, Laconia

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