Under Contract Winhall VT Home for sale $799,000 $259 per sq.ft.

$799,000 $259 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3084  |  Acres: 1
Listed on Wednesday Feb 19, 2025
Description: Showings begin Saturday, February 22, 2025. Set in the heart of Vermont's stunning landscape, this handcrafted Lincoln Log home offers the perfect blend of privacy and convenience. Surrounded by towering Maples and classic stone walls, it's just minutes from Stratton's ski slopes and a short drive to Bromley, Magic Mountain, and Manchester. Inside, a bright, open floor plan features soaring cathedral ceilings and large windows that frame year-round mountain views. The main level, with exposed beams, flows from the dining area into the cozy living room, which opens to a peaceful deck. The chef's kitchen boasts stainless steel appliances, an island cooktop, and solid Hickory cabinetry. The private primary suite includes a Vermont Castings propane stove and a luxurious bathroom with a custom two-head shower and two-person whirlpool tub. Upstairs, two bedrooms, a 3/4 bath, and a loft with sweeping views offer space for relaxation or work. The lower level features a family room, perfect for ping pong or game nights, a fourth bedroom with abundant natural light, and a third 3/4 bath. A mudroom and attached two-car garage complete the home, ideal for storing skis or golf clubs. Furnished and meticulously maintained, this Stratton retreat is ready to create lasting memories with family and friends. See Listing Details & 29 images. Includes a Virtual Tour

$875,000 $313 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2797  |  Acres: 1.1
Listed on Friday Sep 6, 2024
Description: Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for intimate gatherings during spring blooms or lively celebrations as summer stretches into long, lazy evenings. Step outside onto the deck, where a bubbling hot tub invites you to unwind under the stars, no matter the season. The spacious kitchen is ready for your culinary explorations, from summer barbecues to winter comfort food, making it the heart of your home in every season. Whether you're savoring the vibrant colors of fall, the fresh green of spring, or the serene snowfalls of winter, this Vermont home offers a sanctuary for all seasons. Don't miss your chance to own this four-season gem. Embrace the beauty of Vermont and create memories that will last a lifetime, no matter the time of year! See Listing Details & 36 images. Includes a Virtual Tour

$975,000 $367 per sq.ft. Winhall VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 2658  |  Acres: 1.27
Listed on Wednesday Mar 12, 2025
Description: Nestled at the end of a quiet road in the highly sought-after Strattonwald community, 73 Cranberry Hill Road is the quintessential European-style ski house, offering the perfect Vermont retreat. This impeccably upgraded home has never been rented and is turn-key, ready for immediate enjoyment. It combines timeless charm with modern conveniences, featuring air conditioning for year-round comfort. Just minutes from Stratton Mountain, with winter weekend shuttle service right from your doorstep, this property ensures effortless access to all your outdoor adventures. Inside, you'll be greeted by a spacious living room with a striking fireplace, ideal for cozying up after a day on the slopes. The large primary suite offers a private sanctuary, and the inviting 3-season porch lets you savor the beauty of each season. Strattonwald residents also enjoy exclusive private beach and pond access, as well as tennis and pickelball courts in the summer. With Bromley and Magic Mountains nearby and the shops and restaurants of Manchester just a short drive away, this home is perfectly located for all your mountain and recreational pursuits. Experience the charm, comfort, and convenience of 73 Cranberry Hill Road--where every season offers a new story. See Listing Details & 33 images.

Under Contract Woodbury VT Home for sale $625,000 $389 per sq.ft.

$625,000 $389 per sq.ft. Woodbury VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1606  |  Acres: 14.9
Listed on Tuesday Jan 14, 2025
Description: Enjoy lake views in the countryside as each season rolls in. This home offers peace and quiet nestled up on the hillside overlooking Woodbury Lake (Sabin Pond). Sitting on 14.9 acres, the house has a private backyard with plenty of space to enjoy outdoor activities. Take a walk into the woods and you'll find streams and wildlife. As you step inside the home, you'll walk right into a spacious mudroom. The kitchen features a gas range, granite countertops and is open to the dining room making it a great place to entertain. The living room has large windows for natural sunlight, cathedral ceilings and a wood stove providing the perfect warmth for the cold winter months. First floor primary bedroom along with a full bath. The three-season sunroom with direct access to the backyard offers the perfect spot to unwind during the warmer months. Upstairs you'll find 2 additional bedrooms and a full bath. Hardwood floors and tile throughout most of the home. Unfinished basement provides plenty of storage space. 2 car attached garage with a 2nd level for storage. Shed with overhang to store wood. Front deck and back patio offer space for outdoor living. Perennial gardens. High speed internet. Shared right of way to Woodbury Lake. Have picnics, go swimming, kayaking, boating and watch the seasons roll in. Less than a one hour drive to 6 different ski resorts! Escape the daily hustle bustle and unwind in this peaceful and serene setting. See Listing Details & 33 images. Includes a Virtual Tour

Under Contract Woodstock VT Home for sale $545,000 $182 per sq.ft.

$545,000 $182 per sq.ft. Woodstock VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2996  |  Acres: 0.2
Listed on Tuesday May 28, 2024
Description: Constructed in 1840, this post & beam home is situated in the heart of Woodstock Village. A short stroll across the Kedron Brook footbridge to shopping and restaurants, the property is just steps away from all of the amenities this renowned Vermont town has to offer. Woodstock Elementary School, Vail Field and the Woodstock Inn are also just around the corner. Historic High Street, once home to blacksmiths, farriers, and livery stables is a vibrant and connected neighborhood today. The front of the house is anchored by an award-winning ninety-foot mature perennial flower garden and antique stone wall. The private backyard includes raised vegetable beds, fieldstone walls, and terraced garden beds built into the hillside. The property abuts Mt. Peg and all it has to offer, including beautiful walks in the woods, birding, hiking, mountain biking, snowshoeing trails, and XC skiing. Once a two-family dwelling, this spacious single-family home offers a flexible floor plan with room for expansion. The second-floor family room includes a woodstove and opens to an end porch entrance and the backyard. The large second-floor front balcony offers plenty of room for outdoor dining and a birds' eye view of Woodstock Village, High Street and Mt. Tom. See Listing Details & 36 images.

Under Contract Village of Taftsville in Town of Woodstock VT Home for sale $595,000 $350 per sq.ft.

$595,000 $350 per sq.ft. Village of Taftsville in Town of Woodstock VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1700  |  Acres: 0.44
Listed on Thursday Aug 8, 2024
Description: PRICE REDUCTION!! A Quintessential Historic 3 Bedroom, 1,700 sq/ft. Home in Woodstock's coveted Taftsville Village. The "Levi D. Hall House" was built in 1848 by D. Taft & Sons and has been a loved and well-maintained home by the same family for nearly 70 years. Enter into beautiful natural light and a home in pristine condition throughout. The classic country kitchen has high ceilings with original exposed beams, a gas fireplace to add warmth to your colder Vermont days, and direct access to an oversized one car garage. In the Dining and Living Rooms you are greeted with more high ceilings and an abundance of natural light, and the first-floor bedroom/full bath suite has a private dressing area with large closet space. Moving upstairs, there are two attractive bedrooms with wide pine floors and an easy and logical dormer expansion option for larger bedrooms and a large common bath (future investment). There is a generous bonus room for a great home office just off the garage and the property boasts mature perennial beds. Expansive storage space exists above the barn/garage. Attractive covered porch, new furnace in 2023, and upgraded wiring throughout. Be sure to view the Unbranded Tour link. See Listing Details & 40 images. Includes a Virtual Tour

$599,000 $446 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $50,900 down 8% on February 13th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 1344  |  Acres: 0.78
Listed on Thursday Nov 21, 2024
Description: WOODSTOCK-TURNKEY AND CONVENIENT! This totally renovated, move-in ready home located a few minutes to Woodstock Village, 20 minutes to Killington, 30 minutes to DHMC. Enjoy loads of recreational trails of all kinds, just minutes away.  Excellent spot with walking distance to the abutting Woodstock Union Middle School/High School. Newly Renovated inside and out. Spacious open concept living on main floor. The large, finished basement has a TV recreation area, workout space and pool table area. Custom built in cabinetry in the upstairs bedrooms. Private and wooded back yard with a covered porch, perennials, berries and gardens.  Huge potential to add-on, start a home business, create a rental unit or leave quaint and cozy as it is.  This property would be ideal for a primary residence or short-term rental investment property. Schedule your tour today of this sweet Woodstock GEM! See Listing Details & 46 images.

New Listing! Woodstock VT Home for sale $665,000 $248 per sq.ft.

$665,000 $248 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2678  |  Acres: 2.6
Listed on Thursday Apr 10, 2025
Description: Antique Farmhouse just outside of Woodstock Village! c.1903 Dormered Cape set on 2.6 acres of level, open land bordered by a tranquil brook. The property offers a picturesque setting with extensive perennial gardens, a patio by the stream, firepits, covered front porch, rear porch, and deck--perfect for relaxing or entertaining. Inside, the home exudes warmth and comfort, featuring 2,600+ sqft, four bedrooms & three bathrooms. The inviting family room boasts a wood-burning fireplace, while the cozy living room is enhanced by a gas fireplace. The kitchen, with its soapstone Hearthstone brand woodstove and charming breakfast nook, is a delightful gathering space. Updates include newer windows, septic, appliances, and mechanicals, ensuring modern efficiency while maintaining the home's classic appeal. An oversized one-car garage provides ample storage and parking. There is additional storage above the garage with room for potential expansion into an office, game room or studio apartment. This classic Vermont farmhouse offers the perfect balance of historic charm and modern convenience, just 4 minutes from Woodstock's vibrant village center. The Woodstock Green is only a 5 minute drive away as is skiing at Saskadena Six. Close to everything the Upper Valley has to offer while offering a peaceful retreat. A rare opportunity to own a piece of Vermont's pastoral beauty! See Listing Details & 60 images.

$669,000 $456 per sq.ft. Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1468  |  Acres: 1.71
Listed on Thursday Mar 27, 2025
Description: 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. Schedule your private tour today! See Listing Details & 19 images. Includes a Virtual Tour

Under Contract Woodstock VT Home for sale $679,000 $319 per sq.ft.

$679,000 $319 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2128  |  Acres: 1.85
Listed on Friday Mar 21, 2025
Description: 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. See Listing Details & 34 images.

Under Contract Woodstock VT Home for sale $695,000 $194 per sq.ft.

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

4 Beds | 3 Baths |   Total Sq. Ft. 3584  |  Acres: 5.1
Listed on Monday Dec 9, 2024
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 Listing Details & 40 images. Includes a Virtual Tour

$699,000 $357 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1958  |  Acres: 0.68
Listed on Thursday Sep 12, 2024
Description: This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is light filled with a large deck looking out to the Kedron Brook and the Green Mountain Horse Association fields . The Honey Shop is where the Wood family sold honey from the large Bass trees on the property. It is now a lovely room for entertaining or enjoying a quiet spot to take a nap or read a favorite book. The barn could easily convert to garage space with plenty of room for storage . The very back of the barn is the only part of the buildings that is in the Flood zone. The grounds are beautifully landscaped . Cross over the brook on the little bridge to miles and miles of trails. Country living at its best but only 6 miles from Woodstock Village and short distances to skiing , golf, biking, all season sports and of course fly fishing on the Kedron Brook out your back door !. Call today for an appointment . See Listing Details & 39 images.

$785,000 $506 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1550  |  Acres: 0.16
Listed on Monday Mar 24, 2025
Description: Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances, maple flooring and lighting that opens into the dining room accented with a lovely bay window for additional lighting. High ceilings with moldings throughout. Living room features lots of windows and propane stove for those looking to curl up with a book on a cold winter day. Ample room for entertaining. New front door opens to a renovated wrap around covered porch for afternoon tea. Upstairs has 3 bedrooms, renovated bath, shiplapped walls along with all the charm that comes with a 1920's home. New windows, lovely perennial gardens accented with stunning apple tree in front yard when it bloom...as well as a privacy fence. Come take a look... charming cottage in one of America's prettiest towns. See Listing Details & 26 images.

Under Contract Woodstock VT Home for sale $795,000 $432 per sq.ft.

$795,000 $432 per sq.ft. Woodstock VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1840  |  Acres: 33.16
Listed on Tuesday Mar 18, 2025
Description: Enchanting cottage perched on a private knoll with short range views. This property consist of 33 acres with a mixture of open meadow and woods for those looking for an afternoon of walking or snowshoeing. It is currently enrolled in the Current Use Forestry program. Stunning perennial gardens enhance the handsome stone walls and stone walk way to the residence. It's a Garden enthusiasts haven with different variety of ferns. This cozy cottage boast 2 bedrooms, 1.5 baths with 2 loft spaces. It's a perfect open floor plan for entertaining with wide pine floors, exposed beams and anchored by a pellet stove in the living room to cozy up with a book on a winter afternoon. This residence has the advantage of being on one level. Large mudroom leads out to a wonderful covered porch or sunbath on the south-facing back deck in the afternoons. There is a large detached 2 bay garage and generator hook up. Just minutes to GMHA and the Kedron Valley Inn. Championship golf, skiing and fly-fishing on the Black River near by. Woodstock Green is approx 6 miles for access to all the stores, restaurants and amenities. It's a lovely cottage being sold by the original owners- come take a look! See Listing Details & 40 images.

$795,000 $469 per sq.ft. Village of Woodstock in Town of Woodstock VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1694  |  Acres: 0.42
Listed on Friday Feb 7, 2025
Description: This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A comprehensive renovation several years ago opened the main level floorplan to eliminate partitions adapting the house to modern lifestyles. The backyard rises in tiers from the lower level with picnic table and grilling area to an elevated plateau used for expansive vegetable and flowers gardens. Truly a joyful place to call home in the heart of Woodstock's historic community. See Listing Details & 48 images. Includes a Virtual Tour

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