Woodstock Vermont homes for sale starting at Fifty Thousand Dollars

$7,250,000 - Woodstock, VT

412 Skyland Lane Woodstock, VT - 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.

$2,250,000 - Woodstock, VT

4945 South Road Woodstock, VT - 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.

$2,199,000 - Woodstock, VT

15 Hathorn Hill Extension Woodstock, VT - 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.

$1,895,000 - Woodstock, VT

10 College Hill Road Woodstock, VT - 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.

$1,850,000 - Woodstock, VT

2706 East Woodstock Road Woodstock, VT - 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.

$1,800,000 - Woodstock, VT

484 Carlton Hill Road Woodstock, VT - Make this unique Adirondack-style home, with its rich stone and timber frame, and perfect location along the banks of the Ottauquechee River, your new Vermont retreat. Every window offers a stunning view of Mt. Tom, and the rushing river, making it a nature lover's paradise. The fieldstone fireplace soars two stories high in the great room, which is flooded with natural light through expansive thermal glass windows. This generous gathering space hosts a dining area and breakfast bar adjacent to an outstanding chef's kitchen. Crafted with meticulous attention to detail, this remarkable residence features four bedrooms and five bathrooms. The first-floor primary suite is a private sanctuary, boasting custom built-in 'his & hers' closets, a spacious spa-like bathroom, and a secluded sundeck. The tavern room, with its vaulted ceiling, stone fireplace and cherry wood bar makes this the go-to house for friends gathering at any time, but especially on Fourth of July. On the second floor, you'll find a luxurious Primary Bedroom with an en suite bath, an office/study with an adjacent ¾ bath, and a whimsical Children's Suite complete with cozy sleeping alcoves, and charming nooks.Conveniently located within walking distance to Woodstock High and Middle Schools, the Union Ice Arena, and the ever-popular Woodstock Farmer's Market grocery store, this splendid home offers the perfect balance of privacy without isolation.

$1,390,000 - Woodstock, VT

11 College Hill Road Woodstock, VT - 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.

$995,000 - Woodstock, VT

4 River Street Woodstock, VT - This impeccably restored 1847 Woodstock village cape set upon a captivating river front landscape is truly magical! The complete and meticulous efficiency upgrades and renovations combined with the perfect village location offers an incomparable opportunity for those buyers coveting a village location. All new windows and red birch floors set the stage for the interior design. The sun-filled living/dining room with handsome custom built-ins, wood-burning fireplace, and an east facing wall framed beautifully with windows to capture the stunning river view is the focal point of the main level. A warm and delightful kitchen with a custom built-in island detailed with a slate countertop is located just off the living/dining room. An office/study with attached half bath and laundry complete the main level. The upper level offers a primary ensuite bedroom with tiled bath and walk-in shower, walk-in closet, built-ins, and a gorgeous view of the river. A second bedroom and bath complete the upper level. The finished walkout basement is an open and ready canvas for the next owner to transform. Mini-splits and new mechanicals offer comfort and peace of mind for every season in Vermont. A spacious deck and a lush and level lawn are perfect for outdoor dining, recreation, and gardening. Marsh-Billings-Rockefeller National Park is just steps out your door and dining, theatre, and shopping are a lovely stroll away! Schedule your private showing today!

$679,000 - Woodstock, VT

294 Barberry Hill Road Woodstock, VT - Discover this delightful 3-bedroom, 2.5-bath home nestled on 1.8 acres at the end of a peaceful dead-end road. Conveniently located near Woodstock Middle/High School, the Thompson Senior Center, and the popular Woodstock Farmers’ Market. This home offers a spacious and functional layout, the welcoming mudroom features generous storage space and a laundry area cleverly tucked behind sliding doors, along with a recently updated half bath. The low-maintenance slate flooring in the entryway transitions into oak hardwood, that flows seamlessly through the kitchen, living/family room, and dining area. Vaulted ceilings and skylights bring natural light into these expansive spaces, perfect for entertaining. Two wood stoves provide warmth during chilly days and nights. The kitchen is a chef’s dream with a central island, ample counter space, and modern appliances. The cozy den is equipped with beautiful built-ins for books and media storage, while a bay window offers a lovely view of the serene patio. The sunken living and dining area is bright and inviting, ideal for hosting intimate dinners or holiday gatherings. The primary suite features a large, renovated bath and a spacious walk-in closet. A full bath serves the additional two bedrooms. Imagine unwinding on the front porch, listening to the tranquil sounds of the nearby brook. Enjoy outdoor activities like hiking the AT or skiing at Saskadena Six or Killington. The property also includes a large shed for firewood or tools.

$645,000 - Woodstock, VT

187 Dana Road Woodstock, VT - This delightful gambrel cape offers a wonderful combination of thoughtful and charming updates, energy efficient upgrades, and a coveted and convenient location! An intelligent interior design offers an all-season functional flow for everyday living as well as entertaining. Step inside by way of a spacious entryway/mudroom that also has direct entry from the attached garage. One will find the main level design to be a seamless flow from the lovely sunlit living room detailed with handsome woodwork framing a gas fireplace to the cozy kitchen/dining area that opens to an inviting three-season porch. A newly added half bath and a bonus room – perfect for an office/study/media room complete the main level. The upper-level offers three bedrooms – all with lovely views - and a full bath. Recent improvements include blown-in cellulose insulation and 2” exterior insulation, new windows throughout, and a whole-house generator. The exterior landscape consists of 1.71 acres of plentiful open and level lawn area detailed with your quintessential stone wall. Private but convenient makes this location the perfect fit for a primary or vacation home. Enjoy easy access to a multitude of multi seasonal recreating including Killington, Saskadena 6, Marsh Billings Rockefeller National Park, and a terrific neighborhood trail system for hiking and mountain biking. Fabulous dining/shopping/ and the arts are just minutes away in the vibrant village of Woodstock. OPEN HOUSE June 8 from 11am - 2pm

Woodstock, Vermont listings for sale

End of list

There were no properties mapped for this search