Wolfeboro Homes with Outbuildings Exterior Features

Welcome to Wolfeboro, New Hampshire, a charming lakeside town nestled in the heart of Carroll County. Known as the "Oldest Summer Resort in America," Wolfeboro boasts a rich history and an enchanting atmosphere that draws visitors and residents alike. With its stunning views of Lake Winnipesaukee, picturesque downtown, and vibrant community, it’s no wonder that Wolfeboro is considered a hidden gem in the Granite State.

For those seeking a home that offers both charm and functionality, Wolfeboro features a variety of properties with outbuildings. These exterior features provide endless possibilities, whether you envision a cozy workshop, a spacious garage for your recreational vehicles, or even a serene space for hobbies and crafts. Imagine sipping your morning coffee on the porch of your lakeside retreat, with your outbuilding serving as the perfect complement to your lifestyle.

The homes in Wolfeboro often reflect the town's character, with many properties showcasing beautiful architectural details and lush landscaping. Picture yourself in a quaint New England-style home, surrounded by nature's beauty and equipped with the additional space you need for your projects or storage.

With its welcoming community, excellent schools, and an array of recreational activities, including boating, hiking, and fishing, Wolfeboro is not just a place to live; it’s a lifestyle. Discover the perfect blend of tranquility and adventure in this remarkable town, where your dream home with outbuildings awaits. Come and experience the magic of Wolfeboro—your new home is just around the corner!

Newest Wolfeboro Homes with Outbuildings Exterior Features

$675,000

3 Beds ⋅ 2 Baths ⋅ 5116657 MLS

Welcome to 85 York Road, where you'll find 42 acres of privacy, wooded trails, and endless possibilities. Tucked away in a peaceful, wooded setting, this inviting 3-bedroom, 2-bathroom home offers a rare opportunity to enjoy the tranquility of expansive acreage while remaining just minutes from the shops, restaurants, and waterfront of downtown Wolfeboro. Built in 1991, this home features thoughtful updates such as a new roof, new carpeting, minisplits for additional heating and cooling, and a beautifully updated first floor bathroom. Step inside and find an inviting open concept layout, where dining and living spaces flow together beside the kitchen, complete with updated quality appliances. The first floor includes a sizeable primary bedroom, and upstairs are two large bedrooms with an adjoining bathroom, new carpets and plenty of storage. The home includes garage space for two cars and further basement space for storage. A brand-new, generously sized deck provides the perfect setting to relax, entertain, or simply take in the surrounding natural beauty. Overlooking the property's picturesque woodlands and pond, it's an ideal vantage point to appreciate the serenity and privacy that make this property so special. The true standout is the land itself. 42 acres of wooded landscape, extensive trails, and peaceful natural surroundings create an exceptional setting for hiking, exploring, outdoor recreation, or simply enjoying the beauty of New Hampshire's changing seasons. A large outbuilding offers substantial storage space for equipment, recreational gear, and more. Just an hour north of Portsmouth, 45 minutes south of Conway, and 35 minutes from Maine, this property provides an exceptional offering in the heart of New Hampshire. With remarkable acreage, exceptional privacy, and convenient access to all that Wolfeboro and the Lakes Region have to offer, this property delivers a unique combination of seclusion, comfort, and convenience.

85 York Rd, Wolfeboro

$305,000

2 Beds ⋅ 2 Baths ⋅ 5110804 MLS

Here's a great chance to own a 2 bedroom 2 bath home in the quiet neighborhood of The Birches of Wolfeboro, a 55+ community. This home comes with a dedicated 1+ car garage with enough space for your vehicle and storage or a work shop. Step inside and you will see an open floor plan, large living room that flows to a dining room and the big U-shaped kitchen with plenty of storage. Down the hall, you will find the primary bedroom suite, and a secondary bedroom and hall bathroom. This home has been lovingly cared for and landscaped. Here's a great opportunity to call Wolfeboro home and enjoy all that the lakes region has to offer at an approachable price point. Open House Saturday Oct 17th from 9am-11am.

1 Harvey Brook Rd, Wolfeboro

$305,000

2 Beds ⋅ 2 Baths ⋅ 5110795 MLS

1 Harvey Brook Rd, Wolfeboro

$378,500

3 Beds ⋅ 2 Baths ⋅ 5102271 MLS

Located in a quiet 55+ community, this beautifully renovated home is close to a variety of fun and leisurely activities. Enjoy peace of mind knowing the home has undergone a complete renovation over the past three years. Updates include new flooring, fresh paint throughout, remodeled bathrooms, a modern kitchen, updated appliances, a standby generator, new skirting, and a newly landscaped lawn, just to name a few. No expense was spared in creating this move-in-ready home. Now is your opportunity to relax and enjoy life in America's oldest summer resort, where comfort, convenience, and recreation come together.

10 Harvey Brook Rd, Wolfeboro

$378,500

3 Beds ⋅ 2 Baths ⋅ 5102181 MLS

10 Harvey Brook Rd, Wolfeboro

$875,000

4 Beds ⋅ 2 Baths ⋅ 5099338 MLS

This c1820 4Bdrm/2Bath Ctr Chimney Federal on 14 Acres (1/3 Pasture & 2/3 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

$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

$1,550,000

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

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Wolfeboro Homes with Outbuildings Exterior Features

Newest Wolfeboro Homes with Outbuildings Exterior Features

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