You are viewing All Upper Valley 13 Homes between $1000000 and $99999999 dollars.
$2,950,000 $431 per sq.ft. Orford NH Home »
3 Beds | 3 Baths | Total Sq. Ft. 6852 | Acres: 39.79Tuesday Feb 3, 2026
Description: Exceptional New England luxury estate offering privacy, versatility, and multi-generational living on 40+/- acres of open meadows, beautiful woods, and three scenic ponds. The primary and largest pond features a white sand beach, perfect for swimming and lounging. This rare multi-residence property includes a 6,800-square-foot main house with hardwood floors throughout, efficient multi-zone radiant heat, and a dramatic stone fireplace anchoring the living area. Designed for entertaining, the 1,200-square-foot outdoor patio features a fully equipped Lynx outdoor kitchen with refrigerator and cabinetry, plus a gas fire pit. A one-and-a-half-story detached garage near the main house offers ample storage and flexible use. A charming two-bedroom guest cottage is privately sited above its own pond, ideal for guests, extended family, or potential rental use. Additional amenities include a 50' x 70' open-span hangar with an apartment and a New Hampshire-licensed helipad. Private yet conveniently located near the Hanover-Lebanon Upper Valley area, this one-of-a-kind estate offers luxury living, recreation, and exceptional compound potential. A truly must-see property. See MLS Property & Listing Details & 55 images.
$1,342,500 $324 per sq.ft. Plainfield NH Home »
4 Beds | 4 Baths | Total Sq. Ft. 4144 | Acres: 16.87Thursday 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 MLS Property & Listing Details & 60 images.
$3,490,000 $1,206 per sq.ft. Springfield VT Home »
Waterfront on River Connecticut River4 Beds | 5 Baths | Total Sq. Ft. 2894 | Acres: 157.41
Friday Dec 19, 2025
Description: A circa 1734 Cape, displaying museum quality authentic detailing, in a setting worthy of a Vermont Life Magazine cover! Originally sited in New Hampshire, the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The post and beam construction, gunstock corner posts, exposed beams, extraordinarily wide floor boards, 4 beautiful brick fireplaces, wide board sheathing and hand planed surfaces are desirable components of the original Cape! Now, moving forward to the present day, an experienced designer has recently completely renovated the interior! She has seamlessly blended the early New England architectural features with the benefits of contemporary design amenities! The transformation is truly mesmerizing! Notable major upgrades are all new bathrooms, new bedrooms and a fabulous kitchen that was relocated within the home to benefit from the truly spectacular views. Easily this kitchen is the heart of the home, with an oversized fireplace on one side and long dramatic views on the other side. The additional advantages of contemporary mechanical systems, a full size cement basement and whole house back up generator are unobtrusive nods to present day conveniences! This classic Cape features the traditional Cape floor plan of family oriented rooms and kitchen on the main floor, with luxury bedroom suites above. A 30'x20' wing off the Cape presents the desirable practicality of a privately separated ground level primary bedroom suite. With vaulted ceiling and dramatic windows framing views of the pond and distant hills, this bedroom suite easily becomes a favorite room! Completing this expansive 157 acre estate is a detached private guest cottage with a 4 bay garage below, a large swimming pond, an equipment storage barn and walking trails! Within the extensive 157 acres there is a 24 acre field with agricultural potential! An authentic Cape, in an idyllic setting, without antique home worries! See MLS Property & Listing Details & 58 images.
$2,495,000 $520 per sq.ft. Weathersfield VT Home »
5 Beds | 5 Baths | Total Sq. Ft. 4800 | Acres: 52.12Monday Jun 2, 2025
Description: Perched above the Connecticut River Valley with sweeping views to the New Hampshire mountains, this meticulously maintained five bedroom, four and a half bath home offers a rare opportunity just 30 minutes to Hanover, NH, Dartmouth College, and Dartmouth Hitchcock Medical Center. For medical professionals relocating to the Upper Valley, this property provides privacy, acreage, and panoramic views at a value rarely found closer to Hanover or Lebanon. Easy access to I 91 allows a comfortable commute to Dartmouth Hitchcock Medical Center while enjoying a peaceful Vermont setting. The open concept layout offers a desirable main level living option and is well suited for multigenerational living or extended guest stays. Hardwood floors, tall ceilings, and expansive windows fill the home with natural light. The spacious kitchen is ideal for entertaining with granite countertops, high end cabinetry, built in refrigerator, wine fridge, and a generous island with prep sink. Both the living room and den feature fireplaces and custom built ins. Upstairs bedrooms offer comfort and privacy. The walkout lower level with tall ceilings and natural light provides excellent expansion potential for recreation space, gym, or media room. The three-car attached garage includes a separate bay with private entrance and direct access to unfinished space above, ideal for a future guest suite, studio, or in law apartment. Outside, enjoy a spacious deck, fire pit area, cleared yard, fenced pen, and spring fed pond. Convenient to Okemo Mountain Resort, Lake Sunapee, Crown Point Country Club, and Upper Valley amenities. Approximately 2 hours to Boston, MA and under 3 hours to Fairfield County, CT, offering strong appeal for both primary and second home buyers seeking Vermont lifestyle with New England accessibility. See MLS Property & Listing Details & 52 images. Includes a Virtual Tour
Under Contract
![Woodstock VT Home for sale $$1,195,000 $448 per sq.ft.]()
$1,195,000 $448 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32Wednesday Feb 18, 2026
Description: Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions, timeless materials, and an effortless sense of place. The interior is bright, welcoming, and designed for both everyday living and memorable gatherings. Wide board floors run throughout, while exposed beams lend texture and authenticity to the inviting den and spacious eat-in kitchen. A butler's pantry provides exceptional storage and service flow to the formal dining room, and multiple living spaces -- including a fireplaced living room with gas insert and a den warmed by a wood stove -- offer comfortable options for relaxing or entertaining in every season. Positioned on more than eight private acres, the setting feels peaceful and secluded, yet remains remarkably convenient: Woodstock's celebrated restaurants, boutiques, and cultural attractions are just minutes away, and premier skiing at Killington's Skyeship Base Lodge is under eight miles from your door. Outdoor living is equally compelling, with a large deck perfectly oriented toward the mountains, an in-ground pool for summer enjoyment, and an oversized garage/barn with storage above presenting exciting potential for a guest suite, studio, or party barn. A rare combination of location, quality, and lifestyle flexibility, this property is ideally suited as a full-time residence, seasonal retreat, or investment in Vermont living at its best. See MLS Property & Listing Details & 57 images.
Under Contract
![Woodstock VT Home for sale $$1,300,000 $407 per sq.ft.]()
$1,300,000 $407 per sq.ft. Woodstock VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 3195 | Acres: 1.07Tuesday 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 MLS Property & Listing Details & 60 images. Includes a Virtual Tour
New Listing!
![Woodstock VT Home for sale $$1,895,000 $644 per sq.ft.]()
$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
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 MLS Property & 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: 0.46Sunday 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 MLS Property & 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
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 MLS Property & 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: 2.37Monday 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 MLS Property & 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: 63.88Wednesday 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 MLS Property & 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
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 MLS Property & Listing Details & 59 images. Includes a Virtual Tour
