Wolfeboro Homes with Separate Dining Room Interior Features

Welcome to Wolfeboro, New Hampshire – the charming "Oldest Summer Resort in America." Nestled in the heart of Carroll County, this picturesque town is situated along the shores of Lake Winnipesaukee, offering breathtaking views and a serene atmosphere that attracts both residents and visitors alike. Known for its vibrant community, rich history, and stunning natural beauty, Wolfeboro is the perfect blend of small-town charm and outdoor adventure.

As you explore the real estate options in Wolfeboro, you'll discover a variety of homes that cater to diverse lifestyles. One standout feature many of these properties boast is a separate dining room, perfect for hosting family gatherings or entertaining friends. Imagine enjoying a delicious meal in an elegant space designed for comfort and connection, where laughter and conversation flow as freely as the wine.

These homes often feature spacious layouts, allowing for seamless transitions between the living areas and the dining room, making every meal an occasion to remember. Whether you prefer a cozy nook for intimate dinners or a grand dining area for holiday celebrations, Wolfeboro's real estate market offers something for everyone.

Beyond the walls of your potential new home, the town is alive with recreational opportunities, including hiking, boating, and exploring the local shops and restaurants. With a rich blend of history, community spirit, and stunning landscapes, Wolfeboro is not just a place to live – it’s a lifestyle waiting to be embraced. Come discover your dream home in this enchanting lakeside town, where every meal can be a celebration in your separate dining room.

Newest Wolfeboro Homes with Separate Dining Room Interior Features

$3,495,000

4 Beds ⋅ 4 Baths ⋅ 5105279 MLS

Discover a waterfront opportunity on Crescent Lake, tucked into a quiet cove with direct navigable access to Lake Wentworth. With more than 5,000 square feet of finished living space across three levels, this expansive home offers exceptional flexibility for year-round living, a vacation getaway, or investment use in Wolfeboro’s Lakes Region. The main level features an open, light-filled layout with a spacious living area, gas fireplace, built-ins, and direct water views. The kitchen area includes a large separate pantry/coffee bar and an extended dining area that flows naturally together. A primary suite and additional flex rooms which currently used as sleeping spaces which offer options for a home office, hobbies, or other uses. A waterside deck and patio expands the living space, creating an inviting setting for dining, entertaining, or relaxing along the cove. The finished walkout lower level offers a large family room with oak bar and kitchenette, a game room, three additional flex rooms currently used as sleeping spaces, and easy walkout access to the lake. Above the attached garage, a spacious bunk-style sleeping area with individual cubbies provides a separate space. Outside, go and enjoy walk-in water access for swimming, kayaking, paddleboarding, and boating. The quiet cove provides a peaceful setting with navigable access between Crescent Lake and Lake Wentworth. Just minutes from downtown Wolfeboro’s shops, restaurants, and year-round activities, this property combines waterfront recreation, generous living space, and convenient access to the amenities of the Lakes Region.

6 Millwood Rd, Wolfeboro

$9,100,000

5 Beds ⋅ 3 Baths ⋅ 5104599 MLS

Commanding 485' of Lake Winnipesaukee shoreline at the end of its own peninsula, 65 Tips Cove is a generational offering of rare provenance in America's oldest summer resort. Frontage of this scale on a point lot cannot be replicated. Set on 2.75± level, landscaped acres between Tips Cove and Jockey Cove - with a separate .51± acre garden lot available — the property is enveloped by water on nearly every side. Mature white pine buffers behind; ahead, lawn falls to a granite shoreline where the water runs clear. Privacy here is measured not in hedgerows but in open water and quiet. Multiple docking options serve the property: a granite breakwater dock, a U-shaped covered slip, and open-water docking off the deck. Capacity at this scale is difficult to permit anew, and places the Broads, Winter Harbor, and downtown Wolfeboro moments away by boat. The southwesterly exposure is the signature. From a lakeside deck cantilevered above the rocks, summer sunsets fall down the open lake, swinging through autumn to settle behind the Belknap Range, with Rattlesnake Island anchoring the view to the northwest. It is the orientation this lake pays a premium for. The residence is itself a landmark, its red roof recognizable from the summit of Mount Major. Gracious single-level living unfolds beneath soaring ceilings, where grand hallways lead to four private sleeping quarters set apart from a primary suite with en-suite bath. Stone fireplaces anchor the principal rooms, beadboard and natural woodwork frame the ever-present water views, and a formal dining room stands ready for the gatherings to come — an enduring plan, built for multigenerational use and for owners measuring the next thirty years, not the next three. Days begin at the shoreline; nights belong to loon calls and unlit skies. A singular opportunity to acquire one of Winnipesaukee's defining shorefront estates.

65 Tips Cove Rd, Wolfeboro

$995,900

3 Beds ⋅ 3 Baths ⋅ 5103732 MLS

Exceptional Country Ranch set on 8 acres, open concept, kitchen, dining and fireplaced living room First floor laundry. First floor primary suite with 2 additional bedrooms with 3/4 bath. Enclosed porch with views of the Ossipee Mountains and seasonal views of Ossipee Lake. Finished basement with wood stove and walkout onto patio, and additional 3/4 bath and separate work shop. 2 car detached garage with storage above. There will be a cost to take property out of current use.

25 Upper Trask Mountain, Wolfeboro

$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

$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

$1,499,000

3 Beds ⋅ 3 Baths ⋅ 5101400 MLS

Make this immaculate, luxury condo in the heart of desirable Wolfeboro your new home! Elegance and quality are evident from the secure lobby and welcoming common areas, elevator and the rare amenities offered just steps from Lake Winnipesaukee, public docks, fine dining, unique shopping, local museums, theater and music venues. Watch the fireworks from the spacious private balcony, stroll the waterside walking path, enjoy tennis or pickleball at the nearby park. Truly a gracious home for all seasons, you will be welcomed by a large foyer, 2 commodious bedrooms, 2 full baths, open concept living and dining area perfect for cozy evenings and comfortable entertaining. The beautifully appointed kitchen offers extensive custom cabinetry, stainless appliances, and space for all of your culinary adventures. There is a well-designed in-unit laundry room and the option for a gas fireplace. A one-of-a-kind feature is the additional private in-law/guest suite on the lower level with studio living area, private bath and direct entry. An over-sized 2 car garage with work-shop space, deeded storage room and additional exterior parking space round out the many attractions that grace this wonderful opportunity.

61-2 Central Ave Unit 2, Wolfeboro

$540,000

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... 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

$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

$589,900

4 Beds ⋅ 3 Baths ⋅ 5100400 MLS

Charming 4-bedroom, 2.5-bath Cape-style home set on 3.44 private acres in desirable Wolfeboro, NH. This well-maintained property offers a flexible floor plan with comfortable living spaces and plenty of room to spread out. The main level features a welcoming living area and easy flow between rooms, ideal for everyday living and entertaining. The finished basement adds valuable extra space and includes a woodstove for cozy supplemental heat, perfect for a family room, playroom, home gym, or office. Outside, the 3.44-acre lot offers a peaceful setting with room for gardens, outdoor activities, or simply enjoying the natural surroundings. Located just a short drive to downtown Wolfeboro, schools, shops, and Lake Winnipesaukee, this property combines privacy with easy access to all the area has to offer.

1341 Center St, 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

2 Kehonka Hill Rd, Wolfeboro

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