You are viewing Woodstock VT Homes between $0 and $30000000 dollars.
$8,000,000 $1,486 per sq.ft. Woodstock VT Home »
3 Beds | 4 Baths | Total Sq. Ft. 5384 | Acres: 68.92Listed on Monday May 5, 2025
Description: Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a testament to elegant durability. From the mahogany exterior to the hand crafted front doors and custom-wrought hardware, this spacious and meticulously considered home celebrates the skill of Vermont's most talented craftspeople. The unparalleled 180 degree views over the Woodstock valley are spectacular in every season, offering year-round sunlight and ever-changing vistas. With a gourmet kitchen custom-built for entertaining, a 1,000 bottle wine cellar, and a double-sided great room fireplace, Sorgenfrei perfects conviviality. The measures taken to ensure the property's efficiency and durability are too numerous to name - among them, an 18kw solar array, Pella Architect-Series windows, and custom mortise and tenon fir construction. At home among Woodstock's most lauded residences, and gorgeously situated in one of the area's most prestigious neighborhoods, this home is a testament to uncompromising vision and a paean to unparalleled enjoyment of Vermont's Green Mountains. See Listing Details & 47 images. Includes a Virtual Tour
$7,250,000 $1,425 per sq.ft. Woodstock VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 5087 | Acres: 65.45Listed 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 65 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, chicken coop, 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. Showings begin June 7th. See Listing Details & 48 images. Includes a Virtual Tour
$3,500,000 $644 per sq.ft. Woodstock VT Home »
6 Beds | 6 Baths | Total Sq. Ft. 5433 | Acres: 10Listed 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 10 acres comprises of lovely landscaping around the home and plenty of land for gardens and animals. The 18th century barn and corn crib lend much charm to the setting. 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
$2,450,000 $440 per sq.ft. Woodstock VT Home »
48 Ft. of Waterfront on River Ottauquechee River4 Beds | 4 Baths | Total Sq. Ft. 5573 | Acres: 40
Listed on Friday Jan 3, 2025
Description: "All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers unparalleled access to recreational pursuits. Its 40-acre grounds feature single-track biking, hiking, and snowshoeing trails, a firepit, patio, grills, and owned riverfront access. A 32-foot indoor pool, and hot tub under the stars make this a year-round haven. The acreage also includes a potential building lot with mountain views and an existing roadway, adding versatility. Nearby, enjoy world-class skiing, golf, and other outdoor activities, with Woodstock Village offering charming shops and restaurants. Inside, the chef's kitchen boasts Viking appliances, granite counters, dual refrigerators, a pantry, and a custom island. Two expansive great rooms provide gathering spaces with large-screen TVs and plush seating, including a wet bar in the second-floor game room. Accommodations include four bedrooms, three full baths, and space for up to 12 guests. A highly successful Airbnb rental, "All Sessons" is an extraordinary opportunity to own a Vermont escape combining privacy, beauty, and income potential in one of the region's most picturesque towns. See Listing Details & 60 images. Includes a Virtual Tour
$2,250,000 $642 per sq.ft. Woodstock VT Home »
5 Beds | 4 Baths | Total Sq. Ft. 3502 | Acres: 2.57Listed on Monday Feb 10, 2025
Description: The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron Brook, along with a firepit, a barn, and a river meadow. The barn--currently used for storage--could easily be converted to accommodate a couple of horses or sheep. The 3-bedroom main house has elegant 12-over-12 windows, high ceilings, and beautifully preserved period details, including a 2nd-floor ballroom with a coved ceiling and fiddler's stage--a nod to its past as a lively gathering space. The newer addition overlooking the brook has a magnificent great room with 17' cathedral ceilings and a gourmet kitchen and wood burning brick fireplace. The renovated Kingsley Barn guest house offers 2 bedrooms, a loft, and a deck overlooking the brook. Below there is a heated workshop, ideal for puttering and creating. A timber bridge spans the waterway, connecting the property's field, barn and trails. With direct access to the Upwey Trail system and equestrian paths leading to the Green Mountain Horse Association, this property is ideal for outdoor enthusiasts. Located along South Road in the South Woodstock Historic District. See Listing Details & 43 images. Includes a Virtual Tour
$2,200,000 $406 per sq.ft. Woodstock VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 5422 | Acres: 31.43Listed on Wednesday May 28, 2025
Description: Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire home is a unique showplace of clever spaces, built-ins, with custom detail throughout; featuring mahogany, cherry, and locally sourced stone. The ten room- three bedroom, three bath main residence was carefully sited to optimize a stunning northeasterly view, and to communicate directly with exterior terraces, and established gardens overlooking a pond, rolling hills and fields. There is a detached one bedroom guest house (or caretaker's cottage), garage, horse barn, equipment shed and two garden sheds. Easy access to hiking trails. Three minutes to Fitness Ctr., 15 minutes to Saskadena Six skiing. 2.25 hours to Boston, 4.5 to NYC. Property enrolled in Current Use. See Listing Details & 60 images.
$2,199,000 $617 per sq.ft. Woodstock VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 3564 | Acres: 4.15Listed on Friday May 30, 2025
Description: An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a "Vermont Farmhouse" aesthetic. The vaulted ceiling timber frame great-gathering room has reclaimed barn board floors, fireplace, dining area and a gourmet kitchen, with farm sink, soapstone countertops, and Subzero/Kitchen-Aid/Bosch appliances. It opens to a screened-in porch outdoor lounge-area with propane fireplace, and looks down onto the stone patio and dock on the wonderful private pond with walking trail around it, and has a door to the in-ground stone patio and heated swimming pool with automatic cover and a nearby outdoor shower. Upstairs in the house is the primary bedroom with ensuite bathroom, a separate laundry room, an office/bedroom, and two other bedrooms with a large hall bath. Downstairs is a rec room with stacked stone propane fireplace, reclaimed wood cabinets, and a bar. Also downstairs is a full bath with stone/glass shower that opens to a room with a built-in pull-down murphy bed. How fun! OFFERED TURN-KEY, nearly everything now in the house stays/conveys, including all furniture, furnishings, lamps, rugs, kitchen appliances, dinnerware, cookware and utensils - nearly everything in the house stays/conveys. See Listing Details & 34 images.
$1,995,000 $742 per sq.ft. Woodstock VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 2688 | Acres: 0.33Listed on Tuesday Mar 25, 2025
Description: Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had an extensive renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a quaint library with fireplace to curl up with a book on a cold winter day. Off the library is a bathroom and den/bedroom/office. Upstairs includes two more guest bedrooms and bathroom. The new back ell has beautiful architectural lines and features a large kitchen open into an informal and formal dining room anchored by an Austrian- Biofire wood stove. Handsome woodwork, immense amount of sunlight overlooking the perennial gardens. The back of the house has a gracious primary suite with an abundance of space including a reading nook, large en suite bathroom, generous walk in-closet and laundry. New foundation with poured concrete floors, ample storage space as well as an oversized 2 bay detached garage- with generator. Walk to all of towns amenities, restaurants and theatre. Easy stroll to Mtn Peg and Mtn Tom for those hiking enthusiasts. Championship golf, skiing and fly-fishing near by. This is truly an idyllic village home in historic Woodstock that is considered one of the 'prettiest towns in America". See Listing Details & 57 images.
$1,895,000 $450 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $104,000 down 5% on May 14th 2025
5 Beds | 5 Baths | Total Sq. Ft. 4214 | Acres: 1.07
Listed on Tuesday Mar 11, 2025
Description: 10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE. See Listing Details & 35 images.
$1,850,000 $370 per sq.ft. Village of Taftsville in Town of Woodstock VT Home »
Price Change! Reduced by $150,000 down 8% on May 27th 2025
4 Beds | 4 Baths | Total Sq. Ft. 5000 | Acres: 0.56
Listed on Friday Oct 25, 2024
Description: INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, café, or retail store), Post Office (with current lease), smaller Apartment 1 (with excellent AIRBNB rental history), larger Apartment 2 (The owner's unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. See Listing Details & 60 images.
$1,850,000 $878 per sq.ft. Woodstock VT Home »
2 Beds | 3 Baths | Total Sq. Ft. 2106 | Acres: 1.13Listed on Thursday May 29, 2025
Description: Stunning Renovated Antique Cape in the Heart of Woodstock Village! Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village green, shops, restaurants, schools, and trailheads--leave the car behind and enjoy the best of village living. Every system in the home has been thoughtfully updated: all new wiring, plumbing, windows, roof, and high-performance heating and cooling. Geothermal and solar systems power the home efficiently and sustainably, while central air conditioning and radiant floor heating ensure year-round comfort. The floor plan is both flexible and inviting, with two spacious bedrooms--including a primary suite--located on the first floor and easily adaptable to accommodate a third bedroom. Upstairs, a bright, open-concept kitchen and living/dining area lead directly to a glass-covered deck that offers a birds-eye view of the surrounding gardens, village homes, and the conserved forest of Mt. Tom. Outside, extensive perennial beds, raised gardens, and mature plantings create a lush, private oasis. This is a home that lives lightly on the land while offering the walkable, in-town lifestyle so many seek--an exceptional opportunity in one of Vermont's most desirable villages. See Listing Details & 59 images. Includes a Virtual Tour
$1,550,000 $258 per sq.ft. Village of Woodstock in Town of Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 6014 | Acres: 0.05Listed on Thursday Mar 6, 2025
Description: 15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to become Adjutant and Inspector General to organize and direct Vermont's military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owner, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock for office or residential use. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock's future. See Listing Details & 43 images.
New Listing!
$1,495,000 $590 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2532 | Acres: 0.79Listed on Tuesday Jul 1, 2025
Description: A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors--just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully updated bathrooms throughout. Natural light floods the living spaces, which flow easily for everyday living or entertaining. A large, unfinished studio apartment is ready for your design--perfect for an in-law suite, au pair quarters, or as a short- or long-term rental. Above the detached barn, a finished space provides a quiet work-from-home setup or creative studio. With close proximity to the Mt. Peg trail system, this location offers direct access to hiking, mountain biking, and nordic skiing, while the restaurants, shops, and cultural amenities of Woodstock Village are just a short stroll away. A rare opportunity for turn-key living in one of Vermont's most picturesque towns. Showings begin 7/5 with an open house from 10:30am - 12:30pm. See Listing Details & 41 images. Includes a Virtual Tour
Under Contract
$1,390,000 $352 per sq.ft. Woodstock VT Home »
Waterfront on River Ottauquechee River5 Beds | 4 Baths | Total Sq. Ft. 3953 | Acres: 0.6
Listed on Wednesday Apr 30, 2025
Description: Welcome to 11 College Hill Road - Situated in the heart of Woodstock Village, this classic 1919 Gambrel offers space, charm, and incredible views of both the Ottauquechee River and the town's beloved Mount Tom. This beautifully maintained home is perched perfectly above the river with over a half an acre of landscaped outdoor space, including 50 feet of river frontage, mature fruit trees, and stunning perennial gardens. Inside, you'll find hardwood floors throughout, a wonderful cook's kitchen, and sun-filled rooms with views from nearly every window. The flexible layout in the main house features 4 bedrooms and 2 baths, including a spacious primary en-suite, large media/office/recreation room, and two additional above-grade bonus rooms. A separate well-appointed accessory dwelling, built in 2007, offers ideal guest accommodations or income potential, and the soaring ceilings are perfect for a gym or studio. From both structures, enjoy direct access to outdoor living with a huge deck, screened-in porch, and peaceful sounds of the nearby river rapids. Additional features include a heated garage, whole-house generator, lightning-fast internet, and town water/sewer. Walk to restaurants, shops, schools, and hiking trails. Minutes to year-round recreation and a short drive to world-class skiing. This is a must-see property. Book your private tour starting Saturday May 3, 2025. See Listing Details & 52 images.
Under Contract
$1,350,000 $506 per sq.ft. Woodstock VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2668 | Acres: 8.32Listed on Friday Jun 20, 2025
Description: This traditional New England Colonial home was professionally designed and custom built by the renowned Vermont Vernacular Builders. The home is strategically sited to enjoy the long views of the distant hills and to benefit from its southern exposure. This 4 bedroom is a quintessential classic example of pure Vermont living apparent in this gracious sun-filled home. There are wide board floors throughout and ceramic tile in mudroom, kitchen & baths. The home is adorned with exposed ceiling beams in the den & eat-in chefs kitchen. This spectacular home is privately located on over 8 acres just a few miles from Woodstock Village. World class skiing--no problem! Killington Skyeship Base Lodge is a few miles away. The site also boasts an oversized garage/barn with storage and space above for possible additional sleeping accommodations. There is also a lovely in-ground swimming pool with large deck overlooking the mountains. There will be an Open House Sunday, June 29, 11:00 - 2:00. See Listing Details & 35 images.
