luxury real estate for sale South Woodstock, United States

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.

Amazing opportunity to own a property, perfect as a full home or a vacation get away, in the highly desired Heritage Condo community. The setting is serene in a low-density area. This condo has been renovated and updated so that you can move right in. The charming living room is complete with wood floors, a stone accent wall and double glass doors leading t0 private deck looking out to woodlands and back lawn. The bright, sunny kitchen is updated with recent appliances. Upstairs the den with skylight offers opportunity for many uses. There is private storage space in the historic red barn. Woodstock Middle and High Schools are across the road. It is a short distance to all the amenities historic Woodstock Village offers, including dining, shopping and entertainment. Ski at Woodstock's own SaskadenaSix and world acclaimed Killington Mountain. Pentangle Arts Center brings year-round entertainment. Please make an appointment to see this beautiful home today as it will not last long on the market!

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 on the pool table 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.

Fully furnished condo nestled in a small quiet community just 5 minutes from Historic Woodstock. Super location! This unit is in very good condition- first floor is comprised of a den/bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom are perfect size for guests. Lower level has a walk out patio with new slider doors, large family room with a small kitchen and eat-in area, spacious laundry and 3/4 bathroom. Newer Buderus boiler. Pets are allowed- Offered furnished with all new custom curtains. Come take a look at this turnkey property

Handsome condo nestled in a small quiet community just 5 minutes from historic Woodstock. This is an end unit in very good condition- first floor comprised of a den/bedroom with pocket doors for added privacy, lots of bookshelves - an adjacent 3/4 bath with updated tile floors and soapstone countertop. Spacious living room anchored by a wood burning fireplace, nicely crafted mantle and hardwood cherry floors. A couple of steps down takes you into a renovated kitchen with newer stainless appliances and cherry butcher block counters... a small eating area overlooking the back deck with privacy facing East. Tall ceilings allow this space to feel spacious with extra windows and an abundance of natural light. Second floor consisted of a very large primary bedroom with 2 walk-in closets and sitting area. Second bedroom is spacious with lots of sunlight and new carpet. Good size full bathroom with tiled floors. Lower level has a walkout patio, large family room with lots of options for use, renovated 3/4-bathroom, storage and laundry. Pets are allowed! Come take a look at this END UNIT -its turn key.

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 originally part of the King Farm) which is now in Vermont Land Trust as conserved land), until it was subdivided in the late 1980's when the Colby family came into ownership and built the existing house. The dwelling has a wraparound deck overlooking the meadows and pond with views to the south. Historic stone walls are reminiscent of days gone by. Some of the interior features include hardwood floors, an open floorplan that includes dining and living room, and large game room on the lower level. If privacy but convenience to Woodstock village is your goal you need not look further. Easy access to Killington, Okemo Mountain and 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 has been named the prettiest small town in America. Come make it your home in this amazing property.

Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertaining with lovely screened in porch with double doors that lead out to a privately enclosed courtyard. First floor also features a mudroom, new 1/2 bath, family room and gracious formal living room accented with bookshelves. Second floor consists of a large primary bedroom, a guest bedroom and newly renovated full bathroom and laundry room. Third level has another 2 bedrooms or could be used as offices. This residence is the south side (left side) of the building and includes new mini split a/c units, a storage shed and perennials gardens. Walk to all of towns amenities, shops and restaurants. Mt. Tom National park and hiking behind the house for those nature enthusiasts, championship golf, skiing and fly fishing near by. 20 minutes to the Upper Valley and Dartmouth. Wonderful opportunity to own this charming home in one of Vermonts prettiest towns. Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertainment with lovely screened in porch with double doors that lead out to a privately enclosed courtyard. First floor also features a mudroom, new 1/2 bath, family room and gracious formal living room accented with bookshelves. Second floor consists of a large primary bedroom, a guest bedroom and newly renovated full bathroom and laundry room. Third level has another 2 bedrooms or could be used as offices. This residence is the south side (left side) of the building and includes new mini split a/cunits, a storage shed and perennials gardens. Walk to all of town’s amenities, shops and restaurants. Mt. Tom National Park and hiking behind the house for those nature enthusiasts, championship golf, skiing and fly fishing nearby. 20 minutes to the Upper Valley and Dartmouth. Wonderful opportunity to own this charming home in one of Vermont’s prettiest towns.

A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully updated bathrooms throughout. Natural light floods the living spaces, which flow easily for everyday living or entertaining. A large, unfinished studio apartment is ready for your design—perfect for an in-law suite, au pair quarters, or as a short- or long-term rental. Above the detached barn, a finished space provides a quiet work-from-home setup or creative studio. With close proximity to the Mt. Peg trail system, this location offers direct access to hiking, mountain biking, and nordic skiing, while the restaurants, shops, and cultural amenities of Woodstock Village are just a short stroll away. A rare opportunity for turn-key living in one of Vermont’s most picturesque towns. Showings begin 7/5 with an open house from 10:30am - 12:30pm.

Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are plenty of spots for a homesite, a family retreat, or even a simple rustic getaway to relax, recharge, and dream about the future.

The Richmond House Unit B , Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three luxurious residences in the heart of the Village.Unit B occupies the top two floors and offers over 3,200 square feet of beautifully appointed living space with the feel of a private home. The main level features gracious living and dining rooms with a wood-burning fireplace, a spacious family room, and an en-suite study or guest bedroom with its own fireplace. The kitchen opens to the family room and is filled with southern light. A built-in bar near the dining area leads to a private balcony overlooking the Village and landscaped groundsperfect for morning coffee or evening entertaining.The upper level opens to a charming landing with built-in bookcases, a serene primary suite, and an ensuite guest bedroom. A rear Carriage House provides covered garage and storage. With timeless character, refined interiors, and walk-to-everything convenience, this is a rare opportunity to own one of Woodstocks most photographed and cherished historic homes.

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-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.

This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont country kitchen-dining and family room flow into a south facing sunroom overlooking the Ottauquechee River with a terraced yard providing direct access to the water. The home is midway between the resort communities of Woodstock and Killington 5 and 9 miles away. A public park and the Bridgewater Mill showcasing nationally and internationally recognized handmade furniture and pottery of Charles Shackelton and Miranda Thomas, respectively, in addition to a popular restaurant with live entertainment all within walking distance. Ideally sited offering an array of amenities at an attractive price.

Perched on a private hilltop and surrounded by nature, this stunning recently renovated home offers over 141 acres of open and wooded land enrolled in Vermont’s Current Use Forestry Program. Thoughtfully designed by Beilman Design, the residence features gracious living spaces filled with natural light and an exceptional floor plan ideal for entertaining. The handsome chef’s kitchen is appointed with high-end stainless-steel appliances, beautiful countertops, and an exquisite walk-in pantry dedicated to preparation and storage. A spacious guest suite includes two bedrooms and a comfortable sitting area, while the finished lower level offers an additional recreation room with a fireplace. The luxurious primary suite features oversized walk-in closets and a gas fireplace that adds warmth and ambiance. Enjoy the peaceful surroundings from the lovely, screened porch or the expansive covered porch overlooking the sweeping lawn and natural landscape. Offering three levels of refined living, the property also includes a large, oversized barn for storage, a generator, and a driveway alarm system. Conveniently located with easy access to GMHA, skiing, championship golf, and exceptional fishing, this private retreat presents outstanding potential for a family compound or countryside getaway. Landscaping plans are available.

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

Prominently and privately sited overlooking the desirable Bible Hill region of West Windsor, this exceptional, meticulous Davis Timber Frame contemporary home has a panoramic view of Mt Ascutney and sweeping views of the New Hampshire hillside and down the CT River Valley. Masterfully crafted with superior fit and finish, the home is anchored by a 36’ cathedral ceiling with floor to ceiling windows, and a commanding fieldstone fireplace. Gourmet chef’s kitchen with excellent quality appliances, custom Alder Wood cabinetry, soapstone counters and hammered copper farm sink. Luxury primary suite on main level with renovated bathroom and walk in closet. Three additional bedrooms on the second level. The finished walk out lower level featuring a billiards room, media room with pellet stove, a wet bar, steps out to a stone terrace with hot tub, tearoom, outdoor shower. Entertain and wow your guests in your very own heated, covered pizza pavilion. The well-appointed post and beam barn has two stalls with direct turn-out and a 3-bay utility garage. Saddle up, or hop on your bike, and ride into the extensive dirt road and trail systems of West Windsor. Easy access to Interstate, Woodstock and Hanover NH.

Well-maintained Nordic Haus 1BR/BA condo with loft and separate study, ready for new owners. This corner unit has a covered porch, an updated kitchen, and upgraded flooring. Enjoy comfortable, low maintenance living just steps from Ascutney Outdoors for hiking, biking, skiing, and winter tubing. Minutes from the acclaimed Brownsville Butcher Pantry, with easy access to I-91. This property is ideal for first-time buyers, investors, or those seeking a weekend getaway. Right of First Refusal (ROFR)

Views of Mt. Ascutney from this well cared for contemporary home that has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy flow. The charming kitchen leads into a spacious dining room with fireplace. The living room with stunning fireplace leads out to a large deck for outdoor dining. Off the living room the cozy family room features a wall of built-in bookcases. The downstairs bedroom complete with private bath opens onto the spacious screened in porch. The primary bedroom is upstairs. It features a built-in king-sized bed with drawers for extra storage, walk in closets ,and full bath. also on the second floor is another bedroom and bath with walk in shower. The grounds of mature gardens, antique apple trees , blueberry, raspberry bushes ,and original stone walls that border the north and east boundaries create a magical setting. There is ample land to add a garage. Easy access to the Upper Valley with all of the amenities including shopping , Dartmouth College , and world class Dartmouth Medical Center. Woodstock, named by many magazines one of the prettiest small towns in America is less than 25 minutes away.5 hrs. to NYC 2 hrs. to Boston.

Privately sited at the end of a quiet dead end road on beautiful Mt. Ascutney, this cozy 2 BR, 2 BA Chalet style home is an ideal-low maintenance vacation home, or an efficient starter. LR/DR with cathedral ceiling anchored by a sweeping fieldstone fireplace, with woodstove insert; and a spiral staircase leading to aloft perfect for your home office. Kitchen with built ins, and updated appliances. A 3/4 BA further completes the main level. Two bedrooms, full bath and laundry on walkout lower level. Miles of trails for hiking and biking just outside your door, and a short stroll to the year-round recreation and festivities at Ascutney Outdoors. This sweet Chalet is a great opportunity! Most furnishings are available, with a few exceptions. Off peak electric radiators provide heat. Subject to standard ROFR.

This impeccably orchestrated cottage style contemporary home was crafted by Ennis Builders in 2006 with an eye to meticulous detail. The sweeping cherry spiral staircase, beautiful stonework and superior fit and finish imbue a quality of workmanship that reflects throughout the home. The main level features an open-concept kitchen with maple butcher block counters, and quality stainless steel appliances, a dining area with a bank of Pella windows providing plenty of natural light throughout the day. The living room is anchored by a fieldstone fireplace designed and built by master stonemason, Hector Santos flanked by custom cabinetry. There isa guest bedroom/office, and ¾ bathroom. Moving upstairs, the generous primary suite has a walk-in closet and luxury spa bathroom. Watch sunsets from the west facing Juliet balcony. The basement level has laundry/utility room with excellent quality Viessmann boiler and heated two car garages. Central vacuum, radiant and baseboard heat. Mini split to cool those hot summer days. Bamboo floors run throughout main floor, and cherry on second level. Tranquil, private end of road location with sweeping westerly views over an expansive open field. Proximity to State Forest for hiking, 35 miles of biking trails on Mt Ascutney. Easy access to Interstate, Woodstock, and Hanover NH, and all recreation

Tucked away in the peaceful woods of Vermont, this charming Quechee Lakes property offers the perfect escape from the everyday. Surrounded by trees and quiet natural beauty, this property captures the essence of true Vermont livingsimple and serene. This renovated, cozy house is ideal for a weekend getaway or year-round retreat, with plenty of spaces to meet everyone's needs. Inside, youll find warm flooring, exposed beams, and a welcoming open living area centered around a gas stoveperfect for crisp Vermont evenings, relaxing after a day outdoors. The compact yet functional kitchen flows into a comfortable living and dining space, creating an inviting atmosphere for gathering with family and friends. Large windows bring in natural light and frame peaceful wooded views in every season. Step outside onto either deck to enjoy your morning coffee, listen to birdsong, or unwind under the stars. The surrounding area provides privacy and endless opportunities for hiking, snowshoeing, skiing, golf, or finding the local swimming spotmaking it an ideal base for year-round adventure and access to all of Quechee Lakes' amenities.

Conveniently situated on a secluded knoll central to Woodstock Village and beautiful Silver Lake, this impeccably maintained 13.4 AC property offers privacy and convenience. Classic Cape Home is spotless and turn-key. The rooms are bright, and airy, with a great flow for everyday living and entertaining. The living room features a wood burning stove. The kitchen has quality appliances, quartz counters and a butcher block island. There is a main level Primary Bedroom suite. The full basement offers endless opportunity for Family Room, or workshop. Huge level yard ideal for gardening or pasture. The detached barn is perfect for farm animals or as a two-car garage. The animal barn could be easily transformed into a garden shed. Hike the mile long trail network on your own property. Easy access to skiing, and area recreation.

Perched at 1,600 feet elevation between Okemo and Killington, this beautifully furnished 3-bedroom, 2-bath condo at Hawk Resort offers the perfect mountain escape--complete with everything you need to move right in.Step into an open-concept living and dining area that flows onto a private deck through glass sliders--perfect for enjoying the sunsets. The living room features soaring cathedral ceilings, a striking stone fireplace, and abundant natural light, creating a warm and inviting space to unwind after a day on the slopes or trails. The kitchen is equipped with new stainless steel appliances and everything you need for everyday living or entertaining. Each of the three bedrooms is thoughtfully appointed, and two full bathrooms ensure comfort and convenience for guests and family alike. A bonus 14x11 unfinished space is ready to be transformed--windows have already been purchased--offering a customizable opportunity for a home office, studio, or additional sleeping quarters. This condo comes fully furnished, including all furniture, kitchenware, linens, and essential household items--just bring your suitcase. Theres also dedicated storage for outdoor gear and seasonal items, making year-round living or vacationing a breeze.Located steps from Hawks hiking trails and just minutes from world-class skiing at Okemo and Killington, this turnkey mountain getaway combines comfort, convenience, and beautiful natural surroundings

Ledges 8 at Hawk Resort offers the ultimate Vermont mountain retreat, featuring sweeping westerly views and year-round recreation. This spacious 4-bedroom, 3-bath end-unit townhouse spans three levels and is filled with natural light throughout.After a day on the slopes or trails, relax by the striking stone fireplace or unwind on the deck while taking in the mountain scenery. Start and end each day with inspiring views from this peaceful alpine setting.Ideally located halfway between Killington Resort and Okemo Mountain Resort, the property offers easy access to skiing, golfing, mountain biking, hiking, and a full range of four-season activities. Hiking trails are right outside your door, making it simple to enjoy Vermonts natural beauty in every season.