You are viewing Upper Valley Homes between $1000000 and $99999999 dollars.
Under Contract
$1,395,000 $515 per sq.ft. Norwich VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2710 | Acres: 2Listed on Wednesday Sep 17, 2025
Description: This one-of-a-kind spacious home was designed by the architect, George T. Hathorn, and built by G.R. Porter and Sons - both of whom represent an era of home building quality unsurpassed to this day. As befits the climate, the centerpiece of this house is a woodstove, framed by a grand 3-story brick chimney and adjacent staircase - a unique layout that is both beautiful and wonderfully efficient for air-flow and comfort. An abundance of well-placed windows allows natural light to pour through every room. The main floor offers a mudroom, spacious foyer, large living room with fireplace, open concept kitchen-to-dining area, walk-in pantry, and a half bath. The next level boasts a primary en-suite with full bath and walk-in closet, and a bedroom currently set-up as an office. The walk-out basement offers 2 more bedrooms, one with an en-suite full bath, and both with walk-in closets, a recreation room, and utility room with a workshop and laundry area. Situated on 2 acres of beautifully manicured land, it is just a short walk to the village of Norwich, home to the coveted Marion Cross Elementary School (top-rated Hanover High is Norwich's designated high school), and the beloved Dan and Whit's general store. A short drive to Dartmouth College, Dartmouth Health Medical Center, and King Arthur Bakery. This property offers the perfect blend of privacy and convenient access to all that the Upper Valley has to offer. Open House Saturday September 20, 11 AM - 1 PM. See Listing Details & 50 images. Includes a Virtual Tour
New Listing!
$1,595,000 $331 per sq.ft. Norwich VT Home »
5 Beds | 4 Baths | Total Sq. Ft. 4813 | Acres: 10Listed on Monday Apr 27, 2026
Description: Set on 10 private acres bordering conserved land, 15 Happy Hill offers direct access to miles of walking and skiing trails. The property is surrounded by woodland, mature landscaping, and established perennial gardens. The interior features a bright, open-plan design centered around a kitchen built for both cooking and gathering. Anchored by a custom walnut island, the space is equipped with a Sub-Zero refrigerator and Wolf range. This area flows seamlessly into a spacious living room highlighted by a wood-burning fireplace. The main level also provides formal dining and living rooms alongside a relaxed family area, while a full-length back deck overlooks the expansive lawn and gardens. The second floor hosts four well-proportioned bedrooms and two baths, including a primary suite with a large walk-in closet and a spa-like bath featuring a steam shower and soaking tub. Adding to the home's versatility is a two-bedroom apartment with a private entrance and deck; an ideal setup for guests, an au pair, or a quiet home office. This expertly cared-for residence has been extensively updated and renovated with a focus on both interior design and high-end infrastructure. Recent upgrades include a rooftop solar array, Tesla backup batteries, and a new high-efficiency heating and cooling system in addition to kitchen, bathroom, mudroom and basement renovations. If you are seeking a spacious, thoughtfully designed home that offers a private sanctuary within easy reach of Norwich and Hanover, this is it. See Listing Details & 29 images.
Under Contract
$1,845,000 $359 per sq.ft. Norwich VT Home »
3 Beds | 5 Baths | Total Sq. Ft. 5136 | Acres: 10.2Listed on Thursday Apr 16, 2026
Description: Privately set on 10 acres, this stunning contemporary offers the perfect blend of comfort, style, and natural beauty. The gorgeous gourmet kitchen--complete with wet bar and pantry--anchors the home's open-concept design. The sun-filled living room features western exposure and a striking stone hearth. Three bedroom suites, one on main floor and two upstairs provide flexibility and privacy for everyone. Upstairs primary suite has fabulous newly renovated bathroom. Enjoy western views, fun outdoor living spaces - including hot tub, and access to a network of trails from your property. The inviting screened porch with fireplace is ideal for cozy nights. Walkout lower level adds even more living space with a family room, another potential bedroom option, full bathroom, workout area, and abundant storage. A rare opportunity in a coveted Norwich setting. See Listing Details & 60 images.
$2,195,000 $390 per sq.ft. Norwich VT Home »
Price Change! Reduced by $255,000 down 12% on April 28th 2026
5 Beds | 6 Baths | Total Sq. Ft. 5625 | Acres: 7.5
Listed on Monday Jan 26, 2026
Description: 16 OLCOTT ROAD- Elegant, spacious, and immaculate reproduction colonial constructed by premier builder Douglas Gest in an idyllic location minutes to Norwich Village yet privately set with lovely westerly views. This gorgeous home is well-appointed, bright, and has fine finish work at every turn. The main level flows effortlessly from a spacious kitchen and pantry to open concept dining and family room areas and a grand granite patio with persistent views. Also on this level is a library in the southeast corner and a private office space that could provide the option for a future ground floor primary suite. The main second floor has three well-sized bedrooms while the primary suite features a large ensuite bathroom oriented to the west. Additionally, there is a spacious guest bedroom suite and a gym over the garage. On the third level is a bedroom with a full bath, and a bonus room. The land component consists of 7.5 acres with a large open field, mixed woods, and a perfect spot for an additional barn if desired on the northern side of the grounds. This highly desirable location and well-maintained home provide easy access to Hanover, Dartmouth College, Dartmouth Health, local schools, and abundant local trail access. See Listing Details & 60 images. Includes a Virtual Tour
Under Contract
$3,275,000 $696 per sq.ft. Norwich VT Home »
Waterfront on Pond _Unnamed4 Beds | 5 Baths | Total Sq. Ft. 4708 | Acres: 17.5
Listed on Thursday Mar 19, 2026
Description: 207 WILLEY HILL ROAD- Gorgeous, recently updated, sophisticated home a stone's throw away from Norwich, Hanover, Dartmouth College, and the best of the Upper Valley. Expertly renovated by renowned builders O'Hara & Gercke, the result is a seamless blend of luxury, charm, and comfort. The sunlit gourmet kitchen is both functional and elegant and commands breathtaking views of the pond, with an adjoining living room featuring a striking stone fireplace and a sizable deck both offering year-round enjoyment and entertainment. The main floor also includes a library/bedroom and a guest bedroom with scenic views of the lovely grounds. Upstairs, the spa-like primary suite is immersed in nature, with sunrise views and a luxurious soaking tub beneath the sky, while a second ensuite bedroom completes the level. On the lower level is a spacious family room opening to a stone patio plus a multi-purpose room that can be used as either a bedroom or office. The main house was the former home of beloved children's television actor & producer Bob Keeshan, better known as Captain Kangaroo. A separate two-bedroom guest house with a strong rental history adds versatility and possibility to the property. The dwellings are set on 17 private acres with a wildlife-rich pond as its center, beautifully landscaped grounds drawing seasonal long-range views, a pool, woodland trail, and a park-like fenced area. A detached four-bay garage provides ample additional space for cars and storage. This exceptional property is a rare combination of convenience and luxury in a highly desirable locale. Note: Some guest house photos are virtually staged. See Listing Details & 60 images. Includes a Virtual Tour
$1,342,500 $324 per sq.ft. Plainfield NH Home »
4 Beds | 4 Baths | Total Sq. Ft. 4144 | Acres: 16.87Listed on Thursday Mar 12, 2026
Description: A private 16+ acre setting with views of Mt. Ascutney, a pond, barn, and open land to explore make this Plainfield property a special Upper Valley retreat. This home was completedly renovated in 2019. Large windows throughout the home bring in natural light and take full advantage of the surrounding landscape. The main level features a primary suite with walk-in closet and a spacious bath with soaking Jacuzzi tub and separate shower. The kitchen is well equipped for both everyday living and entertaining, with quartz countertops, a Thor Professional gas range, and generous cabinet and storage space. The open kitchen, dining, and living area creates a comfortable central gathering space for family and friends. The finished lower level adds great additional living space with a custom bar, pool table area, office, and exercise room--ideal for entertaining, working from home, or relaxing at the end of the day. Outside, two decks offer inviting spaces for outdoor dining and gathering. Spend summer evenings enjoying the peaceful setting, relax in the hot tub under the stars, or gather around a fire by the pond. In winter, the pond becomes a perfect spot for skating. The property also includes a barn, chicken coop, greenhouse, 2 sheds, treehouse and open acreage to explore. A two-car garage plus additional garage space provides plenty of room for vehicles, equipment, workshop and hobbies. Located just 7 miles from I-89, the property offers an easy commute to all Upper Valley employment while maintaining the privacy and space of a rural setting. See Listing Details & 60 images.
Under Contract
$1,195,000 $448 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32Listed on Wednesday Feb 18, 2026
Description: Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions, timeless materials, and an effortless sense of place. The interior is bright, welcoming, and designed for both everyday living and memorable gatherings. Wide board floors run throughout, while exposed beams lend texture and authenticity to the inviting den and spacious eat-in kitchen. A butler's pantry provides exceptional storage and service flow to the formal dining room, and multiple living spaces -- including a fireplaced living room with gas insert and a den warmed by a wood stove -- offer comfortable options for relaxing or entertaining in every season. Positioned on more than eight private acres, the setting feels peaceful and secluded, yet remains remarkably convenient: Woodstock's celebrated restaurants, boutiques, and cultural attractions are just minutes away, and premier skiing at Killington's Skyeship Base Lodge is under eight miles from your door. Outdoor living is equally compelling, with a large deck perfectly oriented toward the mountains, an in-ground pool for summer enjoyment, and an oversized garage/barn with storage above presenting exciting potential for a guest suite, studio, or party barn. A rare combination of location, quality, and lifestyle flexibility, this property is ideally suited as a full-time residence, seasonal retreat, or investment in Vermont living at its best. See Listing Details & 57 images.
Under Contract
$1,300,000 $407 per sq.ft. Woodstock VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 3195 | Acres: 1.07Listed on Tuesday Nov 11, 2025
Description: Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor primary suite offers ease and convenience, with generous closet space and a private bath. With three additional bedrooms plus a dedicated office, the home offers plenty of room to spread out. The large finished basement provides flexible bonus space--perfect for a playroom, media room, fitness area, or hobbies. Central air conditioning ensures year-round comfort, while an oversized, heated garage and an in-ground irrigation system make this home convenient in every season. Step outside to a private patio, surrounded by terraced gardens and stonework that add character and curb appeal. Located in a quiet setting yet within easy reach of restaurants, shops, and the village green, this property offers modern convenience in one of Woodstock's most desirable walk-to-town locations. A rare opportunity to enjoy newer construction in the heart of Vermont's most charming village. See Listing Details & 60 images. Includes a Virtual Tour
$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
$2,599,000 $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 »
Price Change! Reduced by $550,000 down 19% on March 13th 2026
6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 2
Listed 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
$3,300,000 $896 per sq.ft. Woodstock VT Home »
3 Beds | 5 Baths | Total Sq. Ft. 3682 | Acres: 2.37Listed on Monday Dec 15, 2025
Description: Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary residence is perfectly sited to overlook Woodstock's iconic Mount Tom and the Marsh-Billings Museum, Vermont's only National Park. The property sits at the end of a quiet road with only one other neighboring residence and is surrounded by over 400 acres of conserved land. There is a bedroom suite on each of the three levels, allowing family members or guests to claim their own space. The open living room on the main level is a natural gathering place, either by the fire in the winter, or out on the deck in the summertime to take in the views. The adjoining 1,040-sqft modern pool house was completed in 2023, providing a luxurious new extension of the home. Inside is an open floor plan, where floor-to-ceiling windows showcase unobstructed mountain views to the North and West. Thoughtfully designed with a custom Viking kitchen, spa-style walk-in shower, and guest bed, the pool house is ideal for entertaining guests, hosting family parties, or relaxing apres-ski. The outdoor heated pool is a centerpiece of the property, providing four-season enjoyment. See Listing Details & 28 images. Includes a Virtual Tour
$6,750,000 $1,327 per sq.ft. Woodstock VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 5087 | Acres: 63.88Listed on Wednesday Jun 4, 2025
Description: Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef's kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby. See Listing Details & 48 images. Includes a Virtual Tour
$14,900,000 $1,190 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $3,100,000 down 21% on April 10th 2026
7 Beds | 10 Baths | Total Sq. Ft. 12520 | Acres: 183.7
Listed on Thursday Oct 16, 2025
Description: Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont. See Listing Details & 59 images. Includes a Virtual Tour
