$395,000 $244 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $44,000 down 11% on March 1st 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1617  |  Acres: 0.65
Wednesday Oct 1, 2025
Description: Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full time residence or a Vermont getaway , this property offers an excellent opportunity to enjoy one of Vermont's most desirable areas at an attractive price point. Call today for a private viewing. See MLS Property & Listing Details & 47 images.

$639,000 $293 per sq.ft. Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2183  |  Acres: 1.32
Friday Mar 20, 2026
Description: You know that feeling when you walk through a door and you can already see future memories being made? That's what you feel as you turn every corner of this gem. This thoughtfully updated raised ranch blends comfort, style, and convenience seamlessly with plenty of natural light filling much of the home. Recent improvements include beautifully renovated bathrooms, gleaming hardwood floors, a new roof and central air for year-round comfort. The kitchen is the heart of the home, perfectly positioned for cooking, gathering and listening to laughter fill the living room just steps away. The exercise room and sitting room offer flexible spaces for hosting family and friends or for escaping to a quiet space to work from home. The expansive deck provides a perfect setting for relaxing or entertaining as it overlooks the front yard while the backyard features a fenced-in space ideal for your four-legged companions to enjoy. Just minutes from Woodstock Union High School and the charming shops, restaurants, and amenities of downtown Woodstock, this home is ready to begin its next chapter with you! See MLS Property & Listing Details & 27 images. Includes a Virtual Tour

$675,000 $212 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $14,000 down 2% on March 26th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3190  |  Acres: 2.94
Friday Feb 20, 2026
Description: Historic Woodstock, Vermont - Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont's most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local regulations).Inside, you'll find two charming fireplaces that add warmth and character, perfect for cozy Vermont evenings. The home's classic architecture blends timeless appeal with endless possibilities for customization. Set on over 2 acres, the property features a fenced yard ideal for pets, gardening, or outdoor entertaining. A one-car garage adds convenience, while the separate potting shed--complete with electricity and a heater--offers wonderful space for gardening enthusiasts, creative projects, or additional storage. Located just minutes from Woodstock Village, you'll enjoy easy access to boutique shopping, dining, and the renowned Woodstock Inn & Resort and its spa amenities. Vermont's natural beauty surrounds you--world-class skiing, hiking, biking, and year-round recreation make this an exceptional place to unwind, recharge, and truly enjoy life. A unique property with space, charm, and opportunity in historic Woodstock. See MLS Property & Listing Details & 45 images.

$695,000 $194 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $30,000 down 4% on March 2nd 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3584  |  Acres: 5.1
Saturday Oct 25, 2025
Description: This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont's changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons. See MLS Property & Listing Details & 40 images.

$725,000 $239 per sq.ft. Woodstock VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 3028  |  Acres: 1.18
Wednesday Jan 21, 2026
Description: Charming property located just minutes from historic Woodstock Green. The main house first floor features 3 bedrooms/ 1bath with formal dining room, living room and kitchen on first level anchored by an expansive deck for entertaining or enjoying the afternoon sun. Handsome hardwood floors throughout, stainless appliances in the kitchen accented with granite countertops. The lower level is walk out and includes a very large family room with a 3/4 bathroom and 4th bedroom. Bonus!- there is a wonderful apt located on the ground level for easy access. This apt features a one bedroom, 1bath with living room , dining and kitchen along with its own washer and dryer. It is completely independent from the main house except for water and sewer. Lower level is a 2 bay garage. This apt has been used for both long term and short term rentals with very good rental history. This property is in wonderful condition and close to all of towns amenities including restaurants, shopping, skiing, championship golf and fly fishing. The back of property is abutted by conservation land, located on a dead end road for lots of privacy. Come take a look! See MLS Property & Listing Details & 45 images.

$749,000 $451 per sq.ft. Woodstock VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 1660  |  Acres: 0.19
Saturday Mar 28, 2026
Description: Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and pickleball courts. The homeowners have meticulously updated the property, featuring a stunning new kitchen and a refreshed second-floor bath, blending modern comfort with timeless charm. Unwind on the covered porch with a favorite drink while soaking in the serene surroundings. The inviting living room has a cozy gas fireplace, perfect for cool evenings. The spacious dining area opens to the expanded kitchen, boasting elegant cabinetry, sleek quartz countertops, and top-quality appliances. Newly installed pine flooring adds sophistication throughout. With three spacious bedrooms and two updated bathrooms, each room is designed for comfort. A versatile sitting room off the primary bedroom is perfect as a playroom or quiet study. Additional features include a new boiler, new dining room windows, and upgraded wiring with 200 AMP service. The property also offers a two-stall garage with partially finished space above, presenting endless customization possibilities. Whether you're seeking a forever home or a peaceful retreat, this move-in-ready gem is a must-see! See MLS Property & Listing Details & 39 images.

$817,000 $296 per sq.ft. Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2760  |  Acres: 10.1
Thursday Jul 3, 2025
Description: This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house .The dwelling has a wrap around deck overlooking the meadows and pond with views to the south. Antique stone walls are reminiscent of days gone by .If privacy but convenience to Woodstock village is your goal you need not look further. Some of the features include hardwood floors , open floorplan that includes dining and living room , large downstairs game room. Easy access to Killington, Okemo Mountain and of course Woodstock's own Saskadena Six for Skiing . Golf, tennis . biking and fishing are just a few of the many outdoor activities in the area . Pentangle Arts provides music and theater throughout the year. Woodstock was named the prettiest small town in America . Come make it your home in this amazing property. Call today for an appointment. See MLS Property & Listing Details & 57 images.

$825,000 $212 per sq.ft. Woodstock VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 3886  |  Acres: 2.36
Saturday Sep 6, 2025
Description: NEW PRICE! This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a kitchen with granite countertops, island with seating & storage, double pantry and all new appliances; dining room with fireplace, an all season sun room w/gas fireplace and deck access, a wonderful new laundry room with half bath, lovely primary bedroom and bath with soaking tub, tiled zero step shower(roll-in), & double sinks, & living room w/fireplace. Lots of light and warm wood floors throughout. Two bedrooms with sitting areas and lots of storage and full bath upstairs. The connected 2 bedroom apartment lends flexibility-it can be used as additional living space, overflow for guests or for extra income as a rental. Full kitchen,first floor bedroom and bath,second floor bedroom & storage loft and one car garage with second driveway, private entrance, deck and laundry.The back of the property slopes down to a babbling brook and then up to meet direct trail access to Mount Peg.Expansive deck,generator,attached two car garage & partially finished walk out basement with tons of storage, a recreation room or office and powder room too. So many possibilities! Easy to show and move-in ready! See MLS Property & Listing Details & 60 images.

$845,000 $1,408 per sq.ft. Woodstock VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 600  |  Acres: 6.07
Monday Jun 6, 2022
Description: Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location. See MLS Property & Listing Details & 14 images.

$895,000 $466 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1920  |  Acres: 6.02
Tuesday Jul 1, 2025
Description: PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you'll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot. Well-planned interior space, inside you will find a warm and inviting atmosphere, offering an eat-in kitchen enhanced by the heat from the wood stove or relax by the fireplace in the living room open to the dining room. The primary bedroom with a full bath featuring a jacuzzi tub, while the remaining rooms provide flexible options for guests. Recent updates like a new oil tanks, freshly painted interior, and a new water pressure tank ensure reliable modern living. Located just minutes from the heart of Woodstock, this home gives you easy access to local favorites like the Billings Farm and year-round fun at Okemo Mountain Resort. Whether you're into skiing, hiking, or something entirely more relaxed, there's something nearby for everyone. The neighborhood boasts a strong sense of an upscale community while maintaining a rural, secluded vibe. It's that rare find that feels remote but keeps you close to all the essentials. Ideal for year-round living or a seasonal getaway, this property invites you to experience the best of Vermont in a setting that's equal parts comfort and character. See MLS Property & Listing Details & 45 images.

$915,000 $426 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2150  |  Acres: 1.49
Thursday Jun 5, 2025
Description: Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens. The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes , stone patio and 2 decks offering plenty of spaces for outdoor living and entertaining. The open floor plan provides easy flow and the large windows and glass doors bring the out of doors in. A big bonus is central air conditioning ! The detached 2 car garage provides lots of storage and work space area . Enjoy the charm and various amenities of Woodstock Village that consistently is named one of the prettiest small towns in America . Easy access to sports for every season.. Twenty minutes to the Upper Valley , two and a half hours to Boston and 5 hours to NYC. Call today for an appointment . See MLS Property & Listing Details & 55 images.

$985,000 $354 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2785  |  Acres: 5.01
Monday Jul 21, 2025
Description: This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples. See MLS Property & Listing Details & 37 images.

$1,195,000 $448 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2668  |  Acres: 8.32
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 MLS Property & Listing Details & 57 images.

$1,300,000 $407 per sq.ft. Woodstock VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3195  |  Acres: 1.07
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 MLS Property & 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: 0.46
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 MLS Property & Listing Details & 54 images.