Discover the charm of historic Woodstock in this beautifully maintained late-1800s residence, set on just over an acre of flat, open lawn and ideally located within walking distance to the village. Bordering the scenic Billings Farm & Museum, this 4-bedroom home blends timeless New England character with thoughtful modern updates. Inside, youâ??ll find light-filled living spaces, a well-appointed kitchen, and the convenience of a laundry room on each floorâ??an uncommon luxury in a home of this era. The flexible layout offers room to gather, work, and unwind, while preserving the warmth and craftsmanship of its 19th-century origins. A standout feature is the spacious studio with its own bathroom above the two-car garageâ??perfect as a guest suite, home office, creative workspace. The expansive yard provides abundant space for gardens, play, entertaining, or simply enjoying the peaceful surroundings. With its ideal location, historical charm, and extensive updates, this Woodstock property is a rare opportunity to enjoy village life with room to spread out. A classic Vermont home ready for its next chapter.
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 spaceâ??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 Woodstockâ??s most desirable walk-to-town locations. A rare opportunity to enjoy newer construction in the heart of Vermontâ??s most charming village.
Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end road just minutes west of the historic village of Woodstock. This bright 856 sq/ft two-level home offers an open-concept first floor with a carpeted living/dining area warmed by Empire gas heat (plus electric backup). From this space, step through a newer sliding door to a private deck overlooking landscaped, level grounds on 7 acres of shared land. The kitchen is light-filled and efficient, ideal for everyday living. Hardwood hallway and stairs with dual handrails lead to the second-floor loft, a versatile space with a newer skylight - perfect for an office, studio, or reading nook. The spacious bedroom features newer double-hung windows for an easy-insert air conditioner, Empire gas heat, carpet, and an extra-large closet. The full shower/bath is fully appointed and has electric heating. Additional highlights include; attic storage and a large red barn on the property offering shared storage for bikes, plus an individual security stall for each condominium. Conveniently located near golf, skiing, schools, and shopping, this home blends efficiency and comfort in a serene Woodstock settingâ??ideal as a year-round residence or weekend retreat.
Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end road just minutes west of the historic village of Woodstock. This bright 856 sq/ft two-level home offers an open-concept first floor with a carpeted living/dining area warmed by Empire gas heat (plus electric backup). From this space, step through a newer sliding door to a private deck overlooking landscaped, level grounds on 7 acres of shared land. The kitchen is light-filled and efficient, ideal for everyday living. Hardwood hallway and stairs with dual handrails lead to the second-floor loft, a versatile space with a newer skylight - perfect for an office, studio, or reading nook. The spacious bedroom features newer double-hung windows for an easy-insert air conditioner, Empire gas heat, carpet, and an extra-large closet. The full shower/bath is fully appointed and has electric heating. Additional highlights include; attic storage and a large red barn on the property offering shared storage for bikes, plus an individual security stall for each condominium. Conveniently located near golf, skiing, schools, and shopping, this home blends efficiency and comfort in a serene Woodstock settingâ??ideal as a year-round residence or weekend retreat.
Situated on a lovely .4 acre parcel in the heart of Woodstock Village, this newer construction open-concept home offers modern conveniences combined with superb access to all that Woodstock has to offer. The main floor opens to a vaulted-ceiling living room, dining area, and well-appointed kitchen. Down the hall are two nicely sized bedrooms, and a full bath and laundry/utility room. A 3rd bedroom upstairs rounds out the beautifully functional floor plan. Adding to the comfort of this home is an efficient, on-demand hot water heating system, plus air conditioning via mini-splits in almost every room. There is ample storage throughout the main home and an easily accessible crawl space. Enjoy a cup of coffee in the backyard while listening to the stream that runs along the edge of the property, or take a short stroll and enjoy a meal at one of the many restaurants just minutes away. Walking and biking trails are right out the door, and skiing at Killington is less than 25 minutes away. Don't miss out on this incredible opportunity. Open House Saturday, November 1 from 2 - 4 PM.
Welcome to 33 Mountain Avenue â?? a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one car garage. An exquisite multi-terraced exterior landscape design is predominately and privately located at the back of the property. Plentiful space for gardening, a fire-pit, or even an in-ground pool - where once there was one!  Take in the trails of Mt.Tom and Marsh-Billings-Rockefeller National Park just outside your door. Enjoy a lovely stroll along Mountain Ave and thru the iconic Middle Covered Bridge to tap into a multitude of dining options, shopping, and performances at Pentangle Arts. A rare, unique, and coveted Woodstock Village location!
Discover the charm of historic Woodstock, Vermont in this spacious, light-filled home just minutes from the village green. Blending timeless New England character with modern comfort, this property offers an abundance of space and versatility â?? ideal as a full-time residence or a relaxing ski-season getaway.This inviting home features hardwood floors, custom cherry built-ins, and two fireplaces, creating warmth and character throughout. The in-law suite provides flexibility for guests, extended family, or potential rental income. A heated porch offers year-round enjoyment, while the private backyard provides a peaceful retreat surrounded by nature. The property also includes a one-car garage and ample additional parking. Located only a few miles from Woodstock Village, youâ??ll enjoy easy access to wonderful restaurants, charming shops, Billings Farm & Museum, and scenic hiking trails. Just a short drive to Killington Ski Resort, this home is perfectly situated for both adventure and tranquility.Experience the best of Vermont living in a home that combines charm, comfort, and convenience in one exceptional property.
Idyllic Village condo located a short distance from the Woodstock Country Club, the elementary school, and downtown restaurants and shopping. Perched at the top of Terrace St., there are lovely views across to Mt. Peg, the golf course and Vail Field. Around back, the sunlit deck welcomes you for a morning coffee or dinner on the grill. Tiered gardens and wood steps rise to an upper level grass yard and common area. Inside, beautiful wide pine floors run throughout the condo on both floors. On the main level there are two large bedrooms, both of which share a full bath and there is a spacious foyer with open stairs to the second floor. Upstairs, the floor plan is open and bright. The living room, which has high vaulted ceilings and views across South Road, connects to the dining area, which opens to the kitchen. There are sliding glass doors to the back deck and warm afternoon sun shines in. Across the top of the stairs is an office/den, ideal for a pullout couch, with a 3/4 bath attached. Convenient in town living either as a primary residence or second home getaway.
Gilbertâ??s Hill: The birthplace of American skiing and one of Vermont's most celebrated properties for its contribution to the ski industry. Spanning 112.88± acres in Woodstock (79.31 acres) and Pomfret (33.57 acres), the farm is recognized as the birthplace of lift-served skiing in America, where the first rope tow was installed in 1934. Today, its open pastures, rolling terrain, and historic ski hill remain wonderfully intact â?? a living landscape that forever changed the trajectory of winter sport and the development of recreational skiing in the United States. At the heart of the property is a restored circa 1855 Greek Revival brick farmhouse with four bedrooms, two bathrooms, and a classic mid-19th-century clapboard addition with kitchen and garage. Original details have been thoughtfully preserved, blending historic integrity with comfort and charm. Surrounding the main house is a collection of restored historic buildings, including: a 1934 ski hut, now a three-season cottage with two bedrooms, kitchen and full bathroom; a carriage barn with seasonal kitchen and half bathroom; a dairy barn with milking parlor and six stanchions; and the original milk house. There is also a modern greenhouse pavilion with seasonal half bathroom and a detached 4-bay equipment shed. The land, which includes a vineyard with 700 vines, is conserved with the Vermont Land Trust. The house, dairy barn, milk house and 1934 ski hut are also protected by a historic preservation easement.
Introducing the Mt Peg Condos â?? Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some are virtually staged. Units A and D are end units, and Units B and C are interior units.
Introducing the Mt Peg Condos â?? Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.
Introducing the Mt Peg Condos â?? Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.
Introducing the Mt Peg Condos â?? Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.
Stunning Views overlooking beautiful pastoral meadows as you gaze to the Pomfret Hills. This handsome condo has been completely renovated with cathedral ceilings accented with fireplace and tall bookshelves. Open floor concept ideal for entertaining guests and family with doors to a balcony for outdoor relaxing. An abundance of light fills this home with warm hardwood floors. Second level features a renovated 3/4 bathroom and expansive bedroom with large closets. Lower lever consists of 2 more generous size guest bedrooms with shared bathroom, storage and office. Both bedrooms are walkout overlooking the meadow below. Detached one bay garage, in-ground swimming pool, new skylights with remote control screens and new deck. Just minutes from historic Woodstock Village with access to all of towns amenities, championship golf, skiing, shopping and hiking. Come take a look at this lovely turn-key property with extraordinary views.
Bright and efficient 1-bedroom ground-level condo in the sought-after Heritage Way association, just one mile from Woodstock Village. This move-in-ready coveted end unit offers comfort, privacy, and numerous recent updates. Features include a new Rinnai furnace (2023), new Anderson sliding glass door and bedroom windows (2024), drop ceiling with added sound insulation, and full-size washer and dryer. The kitchen is equipped with a double oven, and the living area opens to a full slate patio overlooking an expansive yard. Enjoy two outdoor storage areas, a quiet setting, and easy access to the Thompson Senior Center next door. Perfect as a year-round home or a low-maintenance Woodstock retreat close to all village amenities.
This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chefâ??s kitchen and den. New Thor stainless steel 48" propane range installed October 2025. Privately set on over 8 acres, the property offers true seclusion with the convenience of being just minutes to Woodstock Village, close to Killington and Okemo skiing, and near local favorites including Ramuntoâ??s Pizza and nearby event venues. Amenities include a private in-ground pool with expansive mountain views, plus an oversized garage/barn with storage and space above for potential guest quarters. An ideal countryside retreat for year-round living or a second home escape.
Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room complete with a wood burning fireplace. A bedroom and full bath on the first floor adds to convenience of living . The charming front porch with views of Killington is a lovely place to enjoy relaxing and entertaining friends . Make an appointment today to view this lovely property .
Open House! Saturday Oct 18 from 10-12. Once known as the Sunshine Nursery School, this home's history expands back to ~1870 and now it stands as a spacious and beautifully updated residence with an expansive terraced yard (one of the largest near the village) and elegant interiors. High ceilings, high-quality wood floors, and sun-filled rooms define the main level, where a gracious primary ensuite with step-in shower, and a glass-lined sunroom create an effortless flow. Thoughtful conveniences include a mini-split for year-round comfort, laundry on the main level, and an eight-foot slider off the dining room that opens to a private deck overlooking the backyard. Upstairs, an apartment with private entrance extends the homeâ??s versatility with its own kitchen, living area, ¾ bath, and two bedroomsâ??perfect for guests, extended family, or private quarters. Outdoors, the property is framed by beautifully established perennial gardens and an expansive yard, offering rare in-village green space on +-.89 acres! A paved drive, two-car garage with overhead storage, standby whole-house generator, and public water and sewer add to the ease of ownership. The location is unmatchedâ??just a street away from the elementary school, Vail Fields, the Village Green, and miles of walking trails. Schedule a private showing and see this grand home for yourself!
Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensiveâ??every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air conditioning. A brand-new two-car garage will be completed before closing, adding convenience and value. Inside, light-filled spaces showcase new, wide-plank white oak flooring, a beautifully designed kitchen, and spa-like bathrooms. The thoughtful floor plan includes a private office, perfect for working from home or creative pursuits. Outdoors, a covered porch with handsome stone entry steps frames gorgeous northerly views, and the roomy 1.53 acre lot provides plenty of room for gardening and outdoor activities. This turnkey home is a rare find: a character-filled property where every detail has been reimagined, offering modern comfort, low-maintenance peace of mind, and proximity to all that makes Woodstock one of New Englandâ??s most desirable communities.
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 Vermontâ??s most beloved communities. Woodstock is often hailed as â??the prettiest small town in America,â? 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 ownerâ??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!
New price! 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!
This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car garage with ample storage above is connected by a breezeway. 3 mini splits for efficiency and comfort. Backup generator, pellet stove, wood stove. Newer heat pump water heater, new windows. Huge shed barn for storage or workshop.
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!Call for showings starting 9/8.
Prime In-Village location on Mountain Avenue just steps to Faulkner Park, The Mt Tom trail system and Woodstock Rec Center. This classic New England duplex (eastern side) home serves perfectly as a full time residence, or an easy keep as a second home. Through a classic covered porch enter the foyer with gleaming hardwood floors and high ceilings. The spacious living room has a propane stove, and large six over six windows flooding the room with natural light. The DR has original built-ins, and connects to a roomy farmhouse eat-in kitchen. Rear mudroom steps out to covered porch and detached garage. Office or overflow bedroom with 3/4 bath completes the main level. Moving upstairs there are three bedrooms, a full and a half bath. Opportunity to expand into the attic space above.
Charming Woodstock Condo in Prime Location Located in the highly desirable High Street neighborhood of Woodstock, this 2-bedroom condo offers the perfect blend of convenience and charm. Just steps from cafes, restaurants, and village amenities, the property provides easy access to everything the village has to offer. A highlight of the home is the inviting screened porch, perched above the Kedron Brook, where you can relax to the soothing sounds of the water. Inside, the condo features comfortable living spaces filled with natural light, well-proportioned bedrooms, and a layout ideal for full-time residence or a weekend retreat. With its walkable location, peaceful setting, and classic Woodstock character, this condo is a rare opportunity to enjoy village living with the beauty of the brook right outside your door.
Woodstock is located in Vermont. Woodstock, Vermont 05091has a population of 3,011. Woodstock 05091 is more family-centric than the surrounding county with 37.05% of the households containing married families with children. The county average for households married with children is 26.01%.
The median household income in Woodstock, Vermont 05091 is $104,716. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Woodstock 05091 is 53.8 years.
The average high temperature in July is 81.4 degrees, with an average low temperature in January of 6.3 degrees. The average rainfall is approximately 46.1 inches per year, with 82.3 inches of snow per year.
