$595,000 $420 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1416  |  Acres: 1.78
Monday Aug 17, 2026
Description: Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classic ski-country retreat. This furnished three bedroom, two bath home offers 1,416 sq ft of inviting living space, thoughtfully designed for both full-time living and memorable getaways. Inside, the vaulted Great Room immediately draws you in with soaring ceilings, warm wood floors, exposed beams, and a dramatic stone fireplace with hearth and wood-storage nook, the ideal gathering place after a day on the slopes or a summer hike. The open kitchen features a breakfast bar and custom stained-glass bar cabinet, creating an inviting space for entertaining. A slider opens to the expansive 400 sq ft deck, where tranquil pond views set the stage for morning coffee, summer dinners, or quiet evenings under the stars. The main level includes a screened porch, welcoming mudroom, bunk room, guest bedroom with deck access, full bath, and laundry closet. Upstairs, a windowed landing leads to a charming loft overlooking the Great Room, offering a cozy reading or relaxation area and generous storage. The vaulted primary suite is a private retreat with his-and-hers closets, sitting area, and en-suite with sauna. Custom wrought-iron fixtures and abundant woodwork enhance the home's warm, authentic character and complement the home's woodland setting. Offered furnished, this turnkey Vermont getaway is equally suited to full-time living, a second home, or a memorable vacation retreat. Enjoy breathtaking views of Stratton Mountain beyond nearby horse-farm paddocks, on your way to Stratton's four-season activities, Manchester's renowned shopping and dining, and Southern Vermont's many outdoor adventures and cultural offerings. Trails toward Gale Meadow Pond are just down Winhall Hollow Road. A unique Southern Vermont retreat ready to create memories for years to come. See MLS Property & Listing Details & 40 images.

$599,000 $317 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1890  |  Acres: 1.09
Sunday Aug 23, 2026
Description: Coming Soon....showings begin Saturday, August 29, 2026. Experience four season Vermont living at 33 Burnt Hill Road in Strattonwald, a recreational community in Winhall just minutes from Stratton Mountain. Set on 1.09 wooded acres, this three bedroom, two bath mountain home combines privacy and Vermont character with access to the Strattonwald swimming pond and beach, tennis courts and winter shuttle service to Stratton. Inside, natural wood, exposed beams and a brick fireplace create the warmth of a classic Vermont retreat. The updated kitchen opens to the dining area, while multiple living spaces provide room for family and friends. The expansive four season sunroom is a highlight, with a vaulted ceiling and walls of glass overlooking the surrounding woods. An additional office or den offers flexibility, and the attached one car garage adds everyday convenience. Late summer means days at the pond and evenings around the firepit. Fall brings hiking, foliage and cool evenings by the fire. When winter arrives, Strattonwald's shuttle makes ski days at Stratton remarkably easy, with Bromley and Magic Mountain also nearby. Manchester is within easy reach for dining, shopping and entertainment. Whether the day is spent swimming, hiking, skiing or simply enjoying the quiet of the woods, 33 Burnt Hill Road offers an inviting home base for experiencing Southern Vermont in every season. See MLS Property & Listing Details & 26 images. Includes a Virtual Tour

$605,000 $386 per sq.ft. Winhall VT Home »

Price Change! Reduced by $20,000 down 3% on August 28th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2288  |  Acres: 1.05
Friday Jun 12, 2026
Description: Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you'll enjoy easy access to skiing, dining, shopping, and year-round recreation. Inside, the home features a spacious living room filled with natural light, creating a warm and inviting atmosphere for gathering and entertaining. Numerous bonus spaces throughout the home provide flexibility for additional sleeping areas, a home office, workout room, or play space. The finished walk-out lower level adds even more living space and functionality, while the corner lot offers a nice yard and deck perfect for relaxing, outdoor dining, or enjoying the fresh mountain air. From ski season to summer adventures, this inviting home offers the perfect setting to enjoy Vermont year-round. See MLS Property & Listing Details & 38 images.

$765,000 $528 per sq.ft. Winhall VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2322  |  Acres: 1
Friday Aug 14, 2026
Description: Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room for family and friends. The dramatic main living area features soaring vaulted ceilings, warm wood accents, a floor-to-ceiling stone fireplace and an impressive wall of windows that fills the home with natural light and brings the outdoors in. The open-concept kitchen, dining and living areas create an inviting setting for gathering after a day on the mountain. Glass doors open to an expansive wraparound deck, perfect for outdoor dining, morning coffee or simply relaxing while taking in the surrounding scenery. At the end of the day, unwind in the private hot tub beneath the Vermont sky. Three comfortable bedrooms are complemented by two bonus rooms and two dens, providing exceptional flexibility for additional sleeping space, a game room, home office, exercise area or quiet retreat. The lower-level den offers a comfortable second gathering space, making it easy to host a full house while still giving everyone room to spread out. A convenient entry mudroom provides practical storage for skis, boots and outdoor gear. Whether you are looking for a ski getaway, a year-round Vermont retreat or a home with room to host family and friends, this inviting property offers the space, comfort and mountain atmosphere to enjoy every season near Stratton. See MLS Property & Listing Details & 32 images.

$1,100,000 $450 per sq.ft. Winhall VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 2745  |  Acres: 10.4
Wednesday Jun 10, 2026
Description: Nestled on 10 private acres just off the Stratton Mountain Access Road, 65 Lower Taylor Hill Road offers a rare opportunity to own a beautifully renovated Vermont retreat ideally positioned between Stratton Mountain Resort and the area's endless four-season recreation. Surrounded by mature woodlands and exceptional privacy, this property offers a three-bedroom, three-bath main house along with a charming bunk house. The home combines refined craftsmanship, modern amenities, and timeless mountain charm. The thoughtfully redesigned interior is highlighted by a dramatic entryway featuring soaring ceilings with exposed beams and beautiful sight lines to the original great room and spacious dining area surrounded by spectacular forest views. French doors from the great room flow onto an expansive covered deck providing sweeping views of the gorgeous mountain surroundings - the perfect place to begin or end the day. Grounding the entry are heated slate tile floors and a convenient mudroom. The stunning all-new custom kitchen features hardwood shaker-style cabinetry, crown molding, elegant slate countertops and professional-grade stainless steel Café appliances. The first-floor master suite includes custom wardrobes and large French doors leading to a private deck. The private en-suite bath features heated slate tile floors, walk-in tile shower, and Kohler finishes. Completing the main floor is a full bath with spacious walk-in tile shower and heated floors. The sunny second floor features two large bedrooms and loft area. The full bath also boasts heated slate tile floors as well as a curved basin tub, and Kohler finishes. The finished basement area includes family space and an adjacent laundry room with new full-sized washer and dryer. The "family favorite" bunk house provides a rustic studio-style flex space with kitchen, full bath, living area, and a roomy loft. Beautiful French doors provide treetop views and lead to a private outdoor sitting area. See MLS Property & Listing Details & 60 images.

$1,650,000 $325 per sq.ft. Winhall VT Home »

Waterfront on Pond
3 Beds | 4 Baths |   Total Sq. Ft. 5072  |  Acres: 1
Wednesday Jul 1, 2026
Description: Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you're hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute drive to Manchester, where you'll find excellent dining and local shops. Step inside the main house to a soaring great room with exposed beams, a dramatic stone fireplace, and lodge vibes that scream cozy comfort. At the heart is a chef's kitchen that opens to a bright sunroom and dining area, ideal for gathering with family and friends. Fireplaces throughout, plus a game-packed entertainment zone with pool table, shuffleboard, arcade games, TVs, and a wet bar bring endless fun indoors. With 3 bedrooms, 2 bonus rooms and 4 bathrooms, there's room for everyone to relax in comfort. But that's not all - this expansive property also includes a 2,250 sqft guest house with an open kitchen, 1.5 baths, covered porch, and an epic downstairs arcade/bar. Outside is a private playground for all ages: fire pit, hot tub, full outdoor kitchen with fireplace, TV, and grills. Enjoy the pond, playground, horseshoes, and a court for basketball, pickleball, or badminton. Whether you're carving fresh powder, basking in summer nights or soaking in Fall colors - this is Vermont living on a whole new level! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$385,000 $139 per sq.ft. Wolfeboro NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2762  |  Acres: 1.93
Thursday Apr 9, 2026
Description: 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! See MLS Property & Listing Details & 43 images. Includes a Virtual Tour

$438,000 $226 per sq.ft. Wolfeboro NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1940  |  Acres: 2.12
Monday Aug 24, 2026
Description: Only 2 miles to downtown Wolfeboro, this charming 3-bedroom, 1½-bath Cape offers classic character, beautiful woodwork, and lovely wood flooring throughout. The inviting kitchen features a sweet breakfast nook, while the dining room overlooks the private backyard. The sunny living room is sure to be a favorite gathering spot, and the first floor is rounded out by a comfortable bedroom and full bath. Upstairs, you'll find two additional bedrooms, a ½ bath with room to expand. A full basement and 1-car garage provide plenty of storage. Outside, the beautiful grounds feature a large garden shed, a vintage stone fireplace, garden space, stone walls, a level yard, and one of the property's most special features, a gorgeous, maturely treed side yard that creates a peaceful, private setting. With its charming character, beautiful grounds, convenient location, and attractive price, this Wolfeboro property is truly a home run! Open House Saturday, 10 AM-1 PM. See MLS Property & Listing Details & 30 images.

$468,900 $271 per sq.ft. Wolfeboro NH Home »

Price Change! Reduced by $11,000 down 2% on August 23rd 2026
Waterfront on Lake Winnipesaukee
3 Beds | 2 Baths |   Total Sq. Ft. 1968  |  Acres: 1.05
Sunday Jun 28, 2026
Description: Welcome to 5 Council Tree Lane in beautiful Wolfeboro, New Hampshire a wonderful opportunity to enjoy life in one of the Lakes Region's most desirable communities. Tucked away in a peaceful setting, this home offers the perfect blend of privacy, comfort, and convenience while still being close to everything Wolfeboro has to offer. Step inside and you'll find a warm and inviting layout with plenty of space for everyday living, entertaining, or simply relaxing after a day on the lake. The home offers a comfortable flow, natural light, and a setting that makes it easy to feel right at home. Whether you are looking for a year-round residence, vacation getaway, or investment opportunity, this property has plenty of potential. Outside, enjoy the quiet surroundings and the charm of a private neighborhood setting. There is room to garden, gather, play, or simply take in the fresh New Hampshire air. Located just minutes from downtown Wolfeboro, Lake Winnipesaukee, shops, restaurants, marinas, beaches, walking trails, golf, skiing, and year-round recreation, this location is hard to beat. Known as "The Oldest Summer Resort in America," Wolfeboro offers small-town charm with four-season fun. From boating and swimming in the summer to snowmobiling, skiing, and cozy local dining in the winter, there is always something to enjoy.5 Council Tree Lane is a great chance to own in a highly sought-after area with access to all the beauty and lifestyle the Lakes Region is known for. Don't miss your opportunity to make this Wolfeboro property your own! (Could potentially be converted to 4 bedroom with one wall install and movement of door entrance and necessary steps etc) See MLS Property & Listing Details & 60 images.

$499,000 $247 per sq.ft. Wolfeboro NH Home »

Price Change! Reduced by $76,000 down 15% on July 24th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2017  |  Acres: 3.3
Friday Feb 27, 2026
Description: 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. See MLS Property & Listing Details & 49 images.

$499,000 $371 per sq.ft. Wolfeboro NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1824  |  Acres: 1.44
Friday Jun 19, 2026
Description: Welcome to 527 North Main Street, a move-in ready home offering over 1,800 square feet of comfortable living space just minutes from downtown Wolfeboro. This charming property features 3 spacious bedrooms, 2 bathrooms, and thoughtful updates throughout, including fresh interior and exterior paint and new appliances, making it easy to settle in and enjoy from day one. The inviting floor plan provides plenty of room to spread out, highlighted by a large finished basement that offers excellent flexibility for a family room, home office, recreation space, or guest overflow. Upstairs, you'll find generously sized bedrooms and a beautifully appointed bathroom featuring a large walk-in shower. Step outside and enjoy the private deck, perfect for entertaining friends and family, summer cookouts, or simply relaxing while overlooking the yard. The property also offers great curb appeal with a nicely sized lawn and a large driveway capable of accommodating multiple vehicles with ease. Conveniently located just 5 minutes from downtown Wolfeboro, you'll enjoy easy access to shopping, restaurants, grocery stores, local amenities, and all that "The Oldest Summer Resort in America" has to offer. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this property combines space, comfort, and a desirable location in one attractive package. See MLS Property & Listing Details & 39 images. Includes a Virtual Tour

$540,000 $301 per sq.ft. Wolfeboro NH Home »

Price Change! Reduced by $8,000 down 1% on August 5th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1796  |  Acres: 1.38
Wednesday Jul 22, 2026
Description: 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. See MLS Property & Listing Details & 30 images. Includes a Virtual Tour

$549,900 $358 per sq.ft. Wolfeboro NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2112  |  Acres: 2.06
Wednesday Jul 15, 2026
Description: 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. See MLS Property & Listing Details & 55 images.

$575,000 $553 per sq.ft. Wolfeboro NH Home »

Price Change! Reduced by $54,000 down 9% on July 20th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2016  |  Acres: 0.74
Thursday Jul 9, 2026
Description: 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 See MLS Property & Listing Details & 14 images.

$589,000 $342 per sq.ft. Wolfeboro NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2344  |  Acres: 0
Wednesday Jul 15, 2026
Description: 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! See MLS Property & Listing Details & 40 images. Includes a Virtual Tour