Woodstock VT
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$395,000 | $244 per sq.ft.
Price Change! reduced by $44,000 down 11% on March 1st 2026
5798 West Woodstock Road
4 Beds | 2 Baths | Total Sq. Ft. 1617 | Acres: 0.65
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.
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Under Contract
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$495,000 | $200 per sq.ft.
Price Change! reduced by $54,000 down 11% on January 2nd 2026
3364 West Woodstock Road
4 Beds | 3 Baths | Total Sq. Ft. 2470 | Acres: 1.96
Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway. Inside, you'll find four comfortable bedrooms and a warm, inviting layout designed for making memories. Gather around the beautiful wood-burning fireplace after a day on the slopes, or enjoy a game in the pool table room with friends and family. Period details and thoughtful updates create a cozy balance of history and comfort, while natural light and open spaces bring the outdoors in. This home is equally suited as a vacation retreat, an investment property, or a welcoming primary residence. Wide lawns offer plenty of room for play and gardening, and river views provide a peaceful backdrop in every season. Here, relaxation and adventure are always close at hand -- whether it's skiing, hiking, or simply soaking in the Vermont lifestyle. See
MLS Property & Listing Details & 35 images. Includes a Virtual Tour
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$527,000 | $289 per sq.ft.
88 Happy Valley Road
4 Beds | 3 Baths | Total Sq. Ft. 1824 | Acres: 0.42
Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including energy-efficient heat pumps, enhanced electrical systems, basement insulation, and newer windows--ensuring comfort and efficiency in every season. Recent capital improvements, such as updated siding, a newer drilled well, and new oil and propane tanks, underscore the home's turnkey reliability, while generator-ready capability provides an added layer of confidence. Enjoy a kitchen built for making memories anchored by a newly installed and sleek granite island perfect for connection and celebration. Outdoors, the revitalized grounds invite both quiet relaxation and effortless entertaining, all framed by the natural splendor of this picturesque village setting. Positioned on coveted Happy Valley Road, the property offers a lifestyle as desirable as the home itself--where morning strolls and evening bike rides become part of your daily rhythm. Just minutes from the boutiques, dining, and charm of Woodstock, as well as convenient access to Interstate 89, this location perfectly balances a charming, village-like setting with accessibility. Imagine summer evenings spent beside the gently flowing stream, gathered around a glowing fire under the stars--an experience that captures the very essence of elevated Vermont living. Showings begin at the open house on Sunday, April 26th, from 1-3pm. See
MLS Property & Listing Details & 48 images. Includes a Virtual Tour
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Under Contract
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$530,000 | $276 per sq.ft.
Price Change! reduced by $165,000 down 31% on April 17th 2026
1514 South Road
3 Beds | 2 Baths | Total Sq. Ft. 1920 | Acres: 6.88
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. See
MLS Property & Listing Details & 43 images.
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$675,000 | $212 per sq.ft.
Price Change! reduced by $14,000 down 2% on March 26th 2026
598 East Woodstock Road
4 Beds | 3 Baths | Total Sq. Ft. 3190 | Acres: 2.94
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.
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$695,000 | $304 per sq.ft.
11 Maple Street
Waterfront Shared 4 Beds | 2 Baths | Total Sq. Ft. 2288 | Acres: 0.15
A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location! See
MLS Property & Listing Details & 11 images.
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$749,000 | $451 per sq.ft.
37 South Street
3 Beds | 2 Baths | Total Sq. Ft. 1660 | Acres: 0.19
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.
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$750,000 | $328 per sq.ft.
New Listing!
47 Pleasant Street
3 Beds | 2 Baths | Total Sq. Ft. 2285 | Acres:
Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4. See
MLS Property & Listing Details & 33 images.
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$815,000 | $248 per sq.ft.
2605 Cox District Road
5 Beds | 4 Baths | Total Sq. Ft. 3284 | Acres: 2.84
This lovely four-bedroom, 2.5-bath cape features a two-car attached garage and a separate 700+/- sq. ft. one-bedroom apartment. The property also includes a separate outbuilding ideal for a workshop or additional storage. The primary living space boasts a modern kitchen with updated cabinetry, granite countertops, and cherry floors. The open-concept family and dining rooms flow into a bright living room equipped with a Woodstock soapstone woodstove, brick hearth, and built-in bookshelves. A three-season porch offers additional space for entertaining. Showings to start May 18, 2026. Open House on May 23, 2026 from 11am to 1pm. The first-floor master suite includes a private full bathroom, two large closets, and a deck. Upstairs, you will find three additional bedrooms, an office/study, and a full bathroom. The separate one-bedroom apartment provides an excellent opportunity for rental income or private guest accommodations. Additional features include a two-car garage and a dog fence/kennel. Located near Mount Tom trails, the home is just five minutes from Woodstock, two minutes from the high school, and twenty minutes from Killington, making it a perfect primary residence or vacation getaway. See
MLS Property & Listing Details & 41 images.
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Under Contract
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$817,000 | $296 per sq.ft.
Price Change! reduced by $168,000 down 21% on October 30th 2025
616 Rose Hill Road
3 Beds | 2 Baths | Total Sq. Ft. 2760 | Acres: 10.1
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.
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