You are viewing all listings Homes between $1000000 and $99999999 dollars.
Under Contract
$2,800,000 $392 per sq.ft. Wolfeboro NH Home »
Price Change! Reduced by $195,000 down 7% on May 11th 2026
7 Beds | 5 Baths | Total Sq. Ft. 7138 | Acres: 2.7
Listed on Friday Nov 7, 2025
Description: Built in 1895, this magnificent Victorian residence stands as one of Wolfeboro's finest off-lake estates--where historic craftsmanship meets contemporary luxury living. Set on 2.7 acres along the town's idyllic North Main Street, the home offers rare privacy within walking distance to the village and Lake Winnipesaukee. Inside, original woodwork, oversized windows and five fireplaces evoke a grander era, while thoughtful renovations introduce contemporary comfort. The designer kitchen features Miele, Bosch and Wolf appliances along with custom cabinetry and a butler's pantry with a copper sink. 7 bedrooms and 5 baths provide ample space for family and guests. Gathering rooms, a movie room and a workshop add versatility, while a ground-level studio opens to a 35×25 patio -- perfect for a painter, potter, or summer entertainer. The original 2,500 sq. ft. carriage house includes a four-car garage ideal for collectors. Outdoors, an 18×40 heated pool with swim jet and pergola anchors lush, landscaped grounds. With town approval, the property would also be suitable for a luxury inn, wedding venue or condominiums. Property is on public water and sewer. Meticulously maintained and lovingly restored, this home represents Wolfeboro's architectural heritage at its most graceful -- a timeless in-town estate that balances history, artistry, and modern ease. See Listing Details & 60 images. Includes a Virtual Tour
$3,995,000 $1,496 per sq.ft. Wolfeboro NH Home »
250 Ft. of Waterfront on Lake Winnipesaukee3 Beds | 3 Baths | Total Sq. Ft. 2670 | Acres: 1.9
Listed on Wednesday Apr 15, 2026
Description: 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. See Listing Details & 52 images. Includes a Virtual Tour
$4,990,000 $1,250 per sq.ft. Wolfeboro NH Home »
100 Ft. of Waterfront on Lake Winnipesaukee4 Beds | 4 Baths | Total Sq. Ft. 3993 | Acres: 1.15
Listed on Wednesday Apr 29, 2026
Description: Die Vier Jahreszeiten - The Four Seasons - is the name the owners chose for this beautiful Winnipesaukee waterfront home because it truly can be enjoyed during each of the Four Seasons. Custom built in 1999, the home features generously sized rooms including three primary suites - one on the first floor and two on the second floor as well as two dens which can provide extra sleeping space for out-of-town guests, a wonderful living room with a cathedral ceiling and a two -story fireplace adjacent to a very pretty dining room with a gas fireplace which opens to a spacious kitchen that was completely renovated in 2025. The attached Carriage House has a lovely studio apartment on the second floor which can provide extra space for family and friends as well as a popular rental. Of course, what you will appreciate the most is the incredible setting in an enchanting cove, protecting the home from the prevailing winds but offers magnificent views across The Broads to the Belknap Mountain Range and glorious sunsets....and your own sugar sand beach along the shoreline just a few steps off the patio. See Listing Details & 35 images.
New Listing!
$5,400,000 $1,421 per sq.ft. Wolfeboro NH Home »
175 Ft. of Waterfront on Lake Winnipesaukee6 Beds | 6 Baths | Total Sq. Ft. 3800 | Acres: 5.84
Listed on Wednesday May 27, 2026
Description: Have you been dreaming of lakefront living? Welcome to 74 Keewaydin Road in Wolfeboro, on Lake Winnipesaukee! This property has over 5 acres of land that sit on the shores of Winter Harbor in Wolfeboro, one of the premier areas of the lake! The southwest exposure allows for sun all day and beautiful sunsets. With a winding driveway thru the woods, there is plenty of privacy as you approach the home. The waterfront boasts a sandy beach and a U-shaped covered dock with a storage shed. The home has plenty of room for everyone plus all the friends and guests! Sitting close to the water, there are endless views from just about every room in the house plus the outdoor space! There are 6 bedrooms with 5 baths. There is a full living space on the first floor with a fireplaced living room, primary suite bedroom, second bedroom, office, kitchen and screened porch as well as an outside deck to enjoy all the waterfront activities! The full second floor has four bedrooms, three baths, a second kitchen, living room with woodstove and deck. The lower level is daylight with plenty of storage space for all the toys! Showings begin on 5/24 with the open house from 11:00 to 1:00. Come and see what lake living is really all about! See Listing Details & 60 images. Includes a Virtual Tour
$9,500,000 $1,167 per sq.ft. Wolfeboro NH Home »
310 Ft. of Waterfront on Lake Winnipesaukee6 Beds | 7 Baths | Total Sq. Ft. 8144 | Acres: 3.03
Listed on Wednesday May 20, 2026
Description: Lake Winnipesaukee waterfront living at its finest. "Woodland Cove" is set on three private acres with 310 feet of pristine sandy shoreline and coveted southern exposure, this extraordinary custom estate captures sweeping views of the lake and the Belknap Mountain range while offering rare protection from prevailing winds. The sugar sand beach allows you to wade in slowly with a sandy bottom extending well off shore. The park-like grounds are a masterpiece of natural beauty, featuring mature gardens, handcrafted stonework, and multiple outdoor living spaces designed to embrace the waterfront setting. A stunning mahogany-and-fieldstone boathouse which is architecturally exceptional--stands as a true centerpiece of the property. The boathouse features a large lift to keep your boat pristine as well. Spanning more than 8,000 square feet, the 13-room residence combines timeless craftsmanship with luxurious comfort. The home features six spacious bedrooms and seven baths, with every bedroom offering its own en-suite bath for ultimate privacy and convenience. Soaring ceilings, elegant crown molding, and walls of glass create an atmosphere of light, space, and sophistication throughout. The decorator furnishings have been curated specifically for this home and are included. Designed for both relaxed lake living and entertaining, the home offers expansive decks, patios, and a beautiful screened porch that seamlessly blends indoor and outdoor living. The first-floor primary suite is a private retreat with breathtaking lake and mountain views, a generous walk-in closet, and a spa-inspired bath. Located just 10 minutes from downtown Wolfeboro, this remarkable property delivers the perfect balance of convenience, exclusivity, and complete privacy on New Hampshire's most sought-after lake. This is truly a special property in the nations "Oldest Summer Resort." See Listing Details & 46 images. Includes a Virtual Tour
$10,950,000 $741 per sq.ft. Wolfeboro NH Home »
430 Ft. of Waterfront on Lake Winnipesaukee7 Beds | 8 Baths | Total Sq. Ft. 14778 | Acres: 6.2
Listed on Wednesday Apr 29, 2026
Description: 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. Select imagery has been thoughtfully enhanced to illustrate the home's potential with refined updates. 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. See Listing Details & 45 images. Includes a Virtual Tour
$1,249,950 $411 per sq.ft. Woodbury VT Home »
3 Beds | 4 Baths | Total Sq. Ft. 3041 | Acres: 218Listed on Friday Sep 26, 2025
Description: Welcome to 187 East Hill Road, an extraordinary 218-acre estate in the serene town of Woodbury, Vermont. This remarkable property is a rare find, offering unparalleled natural beauty and luxurious rustic living. At the heart of this expansive estate lies a charming log cabin, meticulously crafted with exotic hardwoods that infuse warmth and character into every room. Flooring is Brazilian Cherry, the kitchen is custom crafted of Guyana Mahogany, the great room ceiling is finished in Spanish cedar, and the expansive decks and porches are made of luxurious Ipe decking. The cabin seamlessly blends with its surroundings, providing a cozy retreat while offering modern comforts. The property boasts extensive frontage on the pristine Woodbury Lake. Enjoy serene water views from your private dock, or while kayaking, fishing, and peaceful lakeside moments on your private beach, or your additional deeded access to the lake. The estate's vast network of trails invites you to explore the diverse landscape, whether by foot, horseback, or ATV, making it an outdoor enthusiast's dream. Trails follow waterfalls on one border of the property and will allow the perfect location for a zen / meditation garden allowing the opportunity to get lost in the sound of rushing water as your stress melts away. Whether you seek a private retreat, a family compound, or a nature lover's paradise, 187 East Hill Road offers endless possibilities. See Listing Details & 52 images. Includes a Virtual Tour
$1,250,000 $301 per sq.ft. Woodstock NH Home »
Price Change! Reduced by $49,900 down 4% on May 19th 2026
5 Beds | 4 Baths | Total Sq. Ft. 4148 | Acres: 5
Listed on Saturday Feb 21, 2026
Description: Perched high above the valley in the heart of the White Mountains, 81 Meadow Lane offers an extraordinary combination of privacy, flexibility, and breathtaking mountain views. Set on 5 private acres with over 90 degrees of unobstructed views stretching across Franconia Notch and the surrounding peaks, this remarkable property captures the essence of luxury mountain living while remaining just minutes from the energy of Lincoln, Woodstock, and Loon Mountain Resort. Rich in historic character yet thoughtfully updated for modern comfort, the home showcases handcrafted finishes, warm living spaces, and a layout designed to accommodate large gatherings, multiple families, or income-producing opportunities. Configured in a rare tri-plex style arrangement connected by breezeways, the property comfortably hosts 18+ guests while offering exceptional privacy between each section. With three full kitchens, the possibilities are endless -- create the ultimate multi-generational retreat, luxury vacation getaway, or investment property with strong short-term rental potential in one of New Hampshire's most sought-after four-season destinations. Recent improvements include standing seam metal roofing, updated electrical, plumbing, and heating systems, as well as a whole-home standby propane generator for peace of mind year-round. Whether you are seeking a private mountain escape, a second home for gathering with friends and family, or a versatile investment opportunity in the thriving Woodstock/Lincoln market, 81 Meadow Lane delivers a truly rare offering. Experience unforgettable sunsets, unmatched tranquility, and the timeless beauty of the White Mountains from your own mountaintop sanctuary. See Listing Details & 60 images.
Under Contract
$1,495,000 $564 per sq.ft. Woodstock VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 2650 | Acres: 5Listed on Monday May 18, 2026
Description: PROPERTY WILL CONTINUE TO BE SHOWN, UNTIL PENDING. Known affectionately as "Green Gable Farm," this beautifully renovated 1884 Vermont farmhouse sits on 5 picturesque acres in Woodstock, complete with a year-round babbling brook, just minutes from South Woodstock, the Woodstock Inn Fitness Center, golf course, cross-country ski trails, mountain biking, and the Woodstock Village Green. The current owners undertook a comprehensive renovation, thoughtfully preserving the home's historic character--including original barnboard floors and exposed beams--while updating every major system and living space. New mechanicals, upgraded insulation, all new double-pane windows, central HVAC with heating and cooling, high-speed fiber internet, new baths, and a fully redesigned kitchen bring modern comfort to this classic country home. The architecturally reimagined floor plan creates an open, inviting first floor centered around a gourmet eat-in kitchen with Viking appliances, farmhouse sink and abundant workspace. A highly functional mudroom entry, marble tile floors, new laundry room, full bath, and first-floor bedroom add everyday practicality. The kitchen flows into a cozy sitting area with fireplace and additional flexible living spaces ideal for dining, reading, or entertaining. Upstairs are 2 spacious ensuite bedrooms, including a serene primary suite with dressing area, double sinks, smart toilet, glass-enclosed shower, and freestanding soaking tub overlooking stone walls, open fields, and berry patches. Sliding doors off the kitchen open to a large rear deck featuring a heated 12' swim spa for year-round enjoyment. A charming historic shed-barn offers space for a workshop, studio, or recreation area, while unfinished space above the attached two-car garage provides expansion potential. See Listing Details & 52 images. Includes a Virtual Tour
$1,495,000 $410 per sq.ft. Woodstock VT Home »
5 Beds | 4 Baths | Total Sq. Ft. 3648 | Acres: 6.2Listed on Monday May 18, 2026
Description: Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef's kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces--including a wood-burning and gas-ready--add warmth and character throughout the home. The flexible floor plan includes 3-4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage--ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America's first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay--offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England's most iconic villages. See Listing Details & 52 images.
$1,895,000 $644 per sq.ft. Woodstock VT Home »
1000 Ft. of Waterfront on River Ottauquechee River2 Beds | 3 Baths | Total Sq. Ft. 2944 | Acres: 14.9
Listed on Tuesday Apr 21, 2026
Description: Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE. See Listing Details & 33 images. Includes a Virtual Tour
$2,500,000 $488 per sq.ft. Woodstock VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 5127 | Acres: 17.65Listed on Wednesday May 6, 2026
Description: See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock's rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen--complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler's pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies--including a whole-house generator and rooftop solar--offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont's finest amenities. See Listing Details & 60 images. Includes a Virtual Tour
$2,599,000 $434 per sq.ft. Woodstock VT Home »
9 Beds | 11 Baths | Total Sq. Ft. 5993 | Acres: 0.46Listed on Sunday Sep 21, 2025
Description: This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont's most beloved communities. Woodstock is often hailed as "the prettiest small town in America," and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner's quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home! See Listing Details & 54 images.
$2,950,000 $543 per sq.ft. Woodstock VT Home »
6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 2Listed on Friday Jun 28, 2024
Description: Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing. See Listing Details & 40 images. Includes a Virtual Tour
New Listing!
$3,100,000 $640 per sq.ft. Woodstock VT Home »
5 Beds | 6 Baths | Total Sq. Ft. 4843 | Acres: 105.1Listed on Wednesday May 27, 2026
Description: CURTIS HOLLOW FARM- Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef's kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead--with its native timbers and stone fireplace--creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House--a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience. See Listing Details & 58 images. Includes a Virtual Tour
