Featured Listings


Eleven The Green – Woodstock Village


Historic Gem on The Green - Woodstock Village. The setting for this eye catching antique brick Federal is unmatched. Expansive side and rear lawns overlook the Ottauquechee River, famous Middle Covered Bridge and Mount Tom. Original antique features abound in this 11 room, 5 bedroom/5 bath majestic home; 4 wood burning fireplaces warm living spaces and bedrooms. A short stroll to everything Woodstock Village has to offer – dining, shopping, cultural events, and so much more! Premier location in one of the prettiest villages in America.



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Woodstock Vermont Real Estate

Hartland Hill Garden Gambrel


This sweetheart property was a sheep barn in about 1914, when the hills surrounding Woodstock Village were devoid of trees and large flocks of sheep grazed the hillsides. It is now one of those rare Vermont gems: a great 2 bedroom house w/ expansion possibility on 4.1 acres, lawn with stone wall borders, professionally landscaped perennials , vegetable gardens, pond, and a brook side meditation garden. This property is in walking distance to the center of the village, just .3 miles from the Village of Woodstock. There is a woodstove that may heat the house with its open floor plan or a new efficient oil fired boiler. It is a work from home site to consider with a work station alcove that doubles for an extra bedroom for guests, 1 ½ baths, a walkout basement with windows on the south/west side. Convenient yet so, so private, there is an outdoor shower !!!




Woodstock Vermont Real Estate


Button Up Farm

Button Up Farm is paradise! 95 acres of rolling open and wooded land. The views from the extremely well built (2006) 4 bedroom residence are magnificent. A horse lovers delight, with impressive 6 stall barn and drive in hay loft. Miles of trails. Multiple run-in shed and fenced pastures. A hilltop outdoor arena amidst the apple orchard is breathtaking. 4 bay equipment barn and heated drive in workshop. The sheep and chicken barn is conveniently located away from the residence. A wonderful swimming pond with charming pond house complete the package! Priced to sell at a fraction of the replacement value. Come see for yourself!



Cabot Road Cape


Idyllic, serene,scenic and private best describes this lovely home and property. It is a 4 bedroom, 2 1/2 baths quintessential center hall New England Cape, located only 4 miles from the Woodstock Village Green....It sits on 6.5 beautiful acres....with a great mountain view, a peaceful brook, all of which abuts 174 conserved acres. Privacy at its best and yet so close to everything! This home also features an eat in kitchen, formal dining room, large sun filled living room with a wood burning fireplace, a den/ study, plus a mudroom all on the main floor. The 2 car attached garage is an added bonus, especially during the winter months...and let's not forget the Dog kennel for the family pet! This home also has abundant storage throughout! Lastly, there is a spacious daylight/ walkout basement for either a workshop/ hobbies or studio......No doubt, this is a must see home!




Woodstock Vermont Real Estate


High Views in North Bridgewater

High Views from this North Bridgewater home will awe you. One looks to the White Mountains in the East and when you turn to the North you look over the beautiful wildlife pond. There is a 3 bedroom main house and a cozy 1 bedroom 1 bath apartment over the large garage. There is an expanded septic system for 5 bedrooms. The rooms are spacious and filled with light. There is a wood- burning fireplace in the living room with a pizza oven on the back side in the very well equipped kitchen. 3 full baths and a powder room for guests. There is a large 3 bay workshop / equipment barn. The property is very nicely landscaped with old stonewalls, fruit trees, perennials, and blueberries. Built in 2004, this home offers modern amenities in a rural setting. One may sit in the rocker on the front porch or BBQ on the more private patio and enjoy the BIG, BIG VIEW.



Blackbriar Bungalow - Woodstock Town

This is a very private home on 2.5 acres at the end of a town maintained road just over the Village of Woodstock line. The fenced yard with colorful perennials and a stone patio for outdoor enjoyment give the feeling of a country cottage.
There are two bedrooms that share a fresh new bath, a wood burning fireplace for the cool Fall evenings or the snowy chill of Winter, and a fenced yard for the family dog. Built in 1964, the house has been well maintained and a Buderus boiler, some new appliances and an updated septic system make it a great buy at $310,000.




Woodstock Vermont Real Estate


Maplecrest Farm

Grove Hill - Woodstock


This fine property once a part of the historic Old Bailey Farm is three miles up in the hills above Woodstock Village. Backed by a mature forest and fronted by vast rolling meadows, this unique property was thoughtfully sited to maximize the spectacular views of Killington Mountain to the West and the breath taking
unfolding Green Mountain ranges to the North. Maplecrest benefits from protective covenants to neighboring properties.
The 4 bedroom main house has cathedral ceilings and towering, two-story windows, and skylights. The rooms are large and gracious with handsome fireplaces. These spaces lend themselves to any owner's life style from large family gatherings to formal parties.
Adjacent to the main house is one of two guesthouses. This charming, self-contained little Guest House is connected to the main house by a sprawling deck and ramp. It offers relaxing amenities; an efficiency kitchen, a wood burning fireplace, a full bath and a giant whirlpool tub with the BIG view.
The other guesthouse or artist’s studio, nestled in the woods beyond the newly constructed state-of-the art- sauna, has a full kitchen, bath and laundry. It has served as accommodation for overflow guests and also, as a caretaker's cottage. This little house has been a successful vacation rental.
A lovely ride through groomed trails to the south is a horse lover's dream. The trails connect to the country lane that leads to South Woodstock and the well known Green Mountain Horse Association.
This property has a very productive 5000 tap maple sugaring operation, a varietal apple orchard, a rich organic garden plot and an established exuberant blueberry patch!


1845 American Greek Revival
at 28 Pleasant Street

This home has retained much of the original charm & character throughout the years of owners and renovations. It is a "slab~stack” construction. The 2x4 studs were nailed down horizontally and "stacked”, one~on~top of the next. The end result is a solid wood wall with no air space. This construction is from foundation all the way to the peak of roof gables. (including the cantilevered gable above the elegant, recessed front porch). Structural interior walls are made in the same manor. This type of "Slab~ Stack" framing makes for a very sound proofed and tightly insolated home.
The exterior colors were chosen, based on two precedents. An 1868 photo from the Historical Society showing a deeper value color, and the original old doors within the home have this same blue as the finish color. The interior walls are strapped and plastered ~ newer walls have been redone with sheetrock. Most interior walls, are refinished in a hard coat of colored French Teramed Limestone.
The owners of this property call their home the "Gemini House", for its dual personality. The front porch is facing the village
hub-bub with all the village life and activity several blocks away, while the very large lot in the back provides a haven of "Country Living". The privacy of the lower natural terrace on the river provides a feeling of not being in the village. There is a wonderful view looking out at historical Billings Farm & Museum and the National Park.
The Guest House has a history of being a barn, then a two car garage, then an antique store, dentist & law office, guest house and now a design studio. It has had many variable renovations according to the use. The current barn, used as a flower shoppe, is pre-framed to accommodate three single garage door bays. There is an insolated Floras Walk in Cooler within the barn at this time.

The property at 28 Pleasant is a special hidden oasis in the village of Woodstock . There are country gardens, the Ottauquechee River frontage, the fabulous view and privacy. This is truly a magical home to escape time.




Woodstock Vermont Real Estate


High Pastures Farm - Orange County

If you are looking for the best of the best, you've found it. High Pastures Farm features a gracious 5200 square foot, 11 room residence sited to take full advantage of exceptional long range views to the south and west. Nearly all of the 200+ acres are visible from the residence. Totally private with no neighboring homes in view. The entire property, land and structures, have undergone recent and extensive quality, finish and functional improvements. Numerous outbuildings including 3 barns, screened gazebo, studio apartment, workshop and rustic mountain top cabin. Water features include a swimming pond and multiple streams.




Woodstock Vermont Real Estate



Church Hill to old timers, now known as Prospect Street, #16 is a Village of Woodstock property with a view of Mount Tom. There is an oversized two car garage under a home office / a rental studio, or it could be a master bedroom suite. This space is connected to the main house and the deck by a mudroom hallway.
The deck and patio offer a private retreat with a hot tub and out-door shower. There is a screened gazebo for alfresco dining. The main floor is an open floor plan encompassing dining area, well equipped kitchen , and a lovely living room with a cathedral ceiling and a Rumford style fireplace. Many book shelves, yet wonderful spaces for hanging artwork. There is a bath w/ shower and a small bedroom on this main level. The second floor is devoted to a master bedroom suite with dressing room/ laundry, a bathroom that has not only a shower but an antique claw foot tub, for those quiet moments gazing out to the private back yard. The bedroom features a propane fireplace and floor to ceiling glass. This charming residence is a rare opportunity to live in Woodstock Village.


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Woodstock Vermont Real Estate



Wyman Hill – Woodstock, Vermont

      A rare opportunity to acquire one of Woodstock’s most prestigious historic estates. The tasteful renovation has enhanced the charm and function of this light filled, exceptional property. Superb detailed woodwork including raised panel wainscoting, dental and crown moldings. Seven fireplaces many with old delft tiling. A variety of choice wood and tile flooring throughout. Enjoy the sunsets from the pond side stone patio. Rebuilt antique stone walls line the mile of road frontage and meander through the interior of the land along the extensive carriage road-trail network. Bring your wine and cheese to the top of the high meadow and take in the long range southerly views. The rustic cabin and new carriage barn gracefully complement the residence.



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Woodstock Vermont Real Estate


Rush Meadow – West Windsor

   Built in 2004 this Custom Center Chimney Colonial is a scant 2 miles from GMHA and South Woodstock Village. The out open layout on the main level is ideal for gathering friends, family and entertaining. Large windows fill the home with an abundance of natural light. Careful craftsmanship and quality materials include beautiful reclaimed wide plank native pine flooring throughout the first and second levels, solid cherry kitchen cabinetry and mahogany exterior clapboard siding. Direct access from the kitchen/living area to the large rear facing deck. Local views can be expanded with some additional clearing. The master bedroom, with its own fireplace spans the entire width of the house. The lower level includes a family room with sliding door access to the back yard. Need more room? The 3rd level has full staircase access and is ready for finishing! Got horses? Jump right on the GMHA trail system. Plenty of acreage to clear for modest pasture.


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Woodstock Vermont Real Estate


Magnificent Post & Beam frame residence on private setting abutting conserved land and open meadow. Oriented to take full advantage of the breathtaking long range westerly views of the Green Mountains from every room. Every detail of this very special home was carefully thought-out by owner/builder, a timber frame master craftsman. Main level boasts an open floor plan: 24 x 24 Great Room w/ field stone fireplace, soaring cathedral ceilings, master suite, well appointed chef's kitchen & dining space, each light filled w/ direct access to the large deck. The generous mudroom/laundry and office space separate the main living area from the over sized 2 car finished garage. Total of 10+ rooms with 4 bedrooms and 4 baths. Top quality materials and surfaces throughout. Advanced systems & radiant heat. 10 minutes to Woodstock Village & abundance of recreation, shop/dining. Main level is complete, upper/lower levels are partially finished.


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Woodstock Vermont Real Estate


        Saddlebow Farm,

                   Bridgewater c. 1786

This is the only Bridgewater farm listed in the National Register of Historic Places, it has a rich history: the land once owned by Asa Jones, Bridgewater’s first settler, a Vermont hill farm for 145 years until 1931, when it became the Saddlebow Inn for early skiers and a stop-over on the Green Mountain Horse Association Bridle Paths. Since 1937 it has been owned by the same family. During those 73 years it has been a US Army Bivouac in 1941, an Outward Bound winter expedition site in 1975, one of Vermont’s first Christmas tree plantations and Certified Tree Farms, and for recent years an active sheep and horse farm. The farm is now conserved by the Vermont Land Trust as part of the Chateauguay Notown Conservation Project. Its 140 acres feature hayfields, equestrian indoor and outdoor arenas, stable, barns, equipment sheds, caretaker’s house, lean-to campsite, and a rustic cabin on a mountain trout pond. The 5 bedroom house has original random width pine and spruce flooring, basswood & butternut paneling, and original hardware. There are 4 fireplaces, including an antique Franklin Stove, and also a reconditioned cast iron Dockash wood cook stove in the modern, well equipped kitchen. The attached woodshed is an outdoor living room with space above for a future master bedroom suite with fireplace. First and foremost, this well loved and cared for Bridgewater farm has a 3 mile maintained trail system that climbs to Saddlebow Rock at an elevation of 2300 feet on the ridge-line of Ohio Hill. From this well-known lookout there is a 360 degree view deep into New Hampshire and Vermont. This beautiful landmark farm is the keystone of the Gold Coast of Bridgewater. Saddlebow Farm is an 18 karat gold nugget.








Woodstock Vermont Real Estate


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Woodstock Vermont Real Estate