Woodstock VT Luxury Homes

Woodstock VT: $595,000      [ 11 Extra Photos ]
6615 Dunham Hill Road
If you are seeking a charming cottage on 5.05 private wooded acres in Woodstock, this home will speak to you. Built in 1915 by the Gillingham family, and later sold to the daughter of a Russian princess and cousin of Prince Phillip of England. This 3 bedroom, end-of road bungalow offers the writer, artist or recluse the perfect escape to a by-gone era. Hiking, biking and nature trails are easily accessible from the property. Well landscaped and wooded, with a wonderful private forest pond at the entrance. Near the top (and end) of desirable Dunham Hill Road in Woodstock, with lovely sunset and mountain views and privacy. Just minutes from the Woodstock Inn & Resort golf course and the Woodstock town Green. Step back in history and appreciate the very best of fine country living!

Woodstock VT: $1,895,000      [ 11 Extra Photos ]
6001 Worden Road
Whether you are an American history enthusiast, a writer, an artist or a person of fame seeking Vermont privacy, let this property in its unmatchable old time charm inspire you to greater heights of creativity. Apple Hill comprises an historic 1784 cape house on 53.75 acres, two ponds, hiking trails and fabulous views over Killington Mountain. Located in the desirable Dunham Hill area of Woodstock Vermont, the property is only a stone's throw from the famous Woodstock Golf and Country Club and the fine amenities it offers. The restored interior pays respect to the simplicity of a period house, yet has the modern amenities to make you comfortable. The 20x30 three season historic lodge adds value to this remarkable property, which was reportedly visited by presidents. This property has not been listed on the open market in 60 years.

Woodstock VT: $575,000      [ 11 Extra Photos ]
455 Woodstock Road
Wonderful 19th century Victorian appointed with a chef's kitchen, formal dining room, hardwood floors, tin ceilings, comfortable wrap-around porch. Each bedroom offers its own private bath. Master suite has cathedral ceilings and private deck. Enjoy this home with plenty of room for company or guests. Additionally this property has some income potential as a B&B. Close to schools, the Union Arena, and the Farmers Market. Short drive to Killington or other ski areas.

Woodstock VT: $935,000      [ 11 Extra Photos ]
7802 Sawyer Road
Customed designed 2010 mountain home sited on 2.37 acres with lovely views south, west and north towards Marsh Billings National Park, Mt Tom and the Pomfret Hills. There is an open floor plan blending all the main living spaces. Anderson French doors open onto the 12'x 35' mahogany deck. This newly constructed home offers all the best amenities, a gourmet kitchen and baths with granite countertops, Cathedral ceilings, central vac, ADT alarm, propane fireplace and Viessman heating system. Move right in and enjoy private country living with views all within 1/2 mile of Woodstock village.

Woodstock VT: $1,595,000      [ 11 Extra Photos ]
13 mountain avenue
Beautifully situated on Mountain Avenue, this 1840s colonial home has been immaculately maintained and lovingly renovated.Center hall leads to wonderfully proportioned rooms.Lovely side porch traps the afternoon sun. Home is cozy and elegant at the same time. Central air conditioning. Garage has beautiful office and guest space.

Woodstock VT: $2,345,000      [ 11 Extra Photos ] | Ottaquechee
4921 Carlton Hill Rd
Attention fly fisherman and river enthusiast, this is an unrivaled opportunity to own 800 feet of river frontage with a large level lawn and scenic views, all within 2 miles of the Village of Woodstock, Vermont. The lodge style home was architecturally planned with views in mind. The open living room features high ceilings, a stone fireplace, cherry floors, custom cabinets and fine finishes. The kitchen is dressed with high end appliances, custom cherry cabinets and granite counter tops. The spacious master suite has a Jacuzzi tub and separate tile shower and his and her designer closets. The tavern room is a welcoming retreat with its own custom bar and stone fireplace. The home has 4 Bedrooms and 4 baths. There are several outdoor living spaces with an outdoor fireplace.

Woodstock VT: $599,000      [ 11 Extra Photos ]
2008 Grassy Lane
Charming cape hidden away on a country road in one of Woodstock's most sought after locations. Enjoy lovely open fields, stonewalls and miles of trails for hiking and snowshoeing. This quintessential 3 bedroom home features wide pine floors, hand-hewn beams, first floor master bedroom and a wonderful summer porch. A truly special property.

Woodstock VT: $795,000      [ 11 Extra Photos ]
5215 College Hill Rd
Contemporary architect designed home with generous proportions and high ceilings to create airy interior spaces throughout the common areas. First level master suite, LR with stone fireplace, carefully crafted custom kitchen, family BRs on both 2nd and lower levels. Beautiful plantings and grounds including pond, walk to village center.

Woodstock VT: $2,450,000      [ 11 Extra Photos ]
3 Border Lane
This individual style contemporary home, was thoughtfully and meticulously renovated in 2004 and reflects the highest quality of interior and exterior finishes. The property is located on 8 private acres with spectacular long range western mountain views and sunsets, and is within easy walking distance of Woodstock Village. The interior provides one level living with an open floor plan, that gracefully blends all the main living areas. The house has many special features i.e. gourmet kitchen with imported Brazilian granite counter tops, Brazilian leopard wood cabinets, new addition with master bedroom suite, walk-in closet and bath with imported Spanish marble. Surrounded by landscaped grounds and gardens there is a 15' stone waterfall and oversized flagstone patio with Viking outdoor grill. A magnificent home of charm and understated elegance with views, views, views.

Woodstock VT: $590,000      [ 10 Extra Photos ]
1625 Westerdale
Sited ideally for southern exposure,long range views,& protection on northside. This 1987 antique cape replica is minutes from Woodstock village. Offers 1st floor MBDRM with full ensuite BA,26'x36'heated with power detached workshop,15'x22'office above garage, & 17'x14' studio above attached apartment which could become 2nd BDRM for apt.

Woodstock VT: $795,000      [ 11 Extra Photos ] | Ottauquechee River
5 CHURCH STREET
AN HISTORIC VILLAGE PARSONAGE, WITH AN EXTENSIVE LAWN, BOUNDED BY THE BEAUTIFUL OTTAUQUECHEE RIVER! IDEALLY LOCATED JUST A FEW STEPS FROM THE VILLAGE GREEN. THE EXPANSIVE INTERIOR FEATURES AN ARCHITECT DESIGNED KITCHEN, WITH QUALITY APPLIANCES. EXCELLENT IN HOME OFFICE SPACE, GENEROUS SIZE PRIMARY BEDROOM SUITE, A GRACIOUS FAMILY ORIENTED INTERIOR.

Woodstock VT: $1,089,000      [ 11 Extra Photos ]
745 Atwood Lane
The Cottage- A handsome, newly renovated residence. Enjoy lovely views over the Vermont countryside with a large pond, perennial gardens and stonewalls surrounding the estate. Beautiful craftsmanship with fir/pine floors, custom cherry cabinetry, granite countertops and stone fireplace. Property may be subdivided into several other building lots or created into a family compound. Several other building sites available with views. Quiet, private road 6 miles to Woodstock Village and all of towns amenities. Suicide Six, Killington and Okemo Mtns in close proximity. Enjoy fishing and championship golf.

Woodstock VT: $4,200,000      [ 11 Extra Photos ]
3607 Fletcher Hill Extension
Set on a country road in serene South Woodstock, Lottery Hill Farm is an elegant Vermont farm on 121+/- acres of meadows, woodlands and ponds. Legend has it that the handsome 16 room brick Federal was built in 1817 by Salmon Hoisington with winnings from the Louisiana lottery. The colorful history continued with a complete restoration by former owner Michael J Fox retaining much of the original period detail while offering the expected amenities. The property also includes a significant barn, outbuildings, and a 3 bedroom guest house.

Woodstock VT: $575,000      [ 4 Extra Photos ]
7315 Hartland Hill
Just outside the village of Woodstock sets the property known as the former " MacKenzie Farm ". This property consists of a small 1280 sq. foot , 3 bedroom, 2 bath reidence, a large 3 story 30' x 50' barn plus other out buildings all situated on 47.90 + or - open and wooded acres with a small year round stream running through the property.

Woodstock VT: $695,000      [ 11 Extra Photos ]
THIS IMPRESSIVE BRICK CAPE BENEFITS FROM BOTH OLD AND NEW SPLENDID ARCHITECTURAL FEATURES. WELL LOCATED, FOR PARTAKING OF THE AMENITIES OF WOODSTOCK VILLAGE, AS WELL AS THE LIMITLESS RECREATIONAL OPPORTUNITIES OF MOUNT TOM PARK. THE EXTRAORDINARY, PROFESSIONAL QUALITY KITCHEN AND LARGE FIREPLACED LIVING ROOM ARE DESIGNED FOR GRACIOUS ENTERTAINING.

Woodstock VT: $525,000      [ 4 Extra Photos ] | Ottauquechee River
26 Pleasant Street
Woodstock Village,Pleasant Street, River Frontage constructed in 1840 with solid wood walls and originally known as the Ransom Russell house. Mr. Russell was a cooper smith.Total of 9 rooms, 5 bedrooms and 1 1/2 baths plus an attached garage and former horse and stable barn. Property runs from Pleasant St. to the Ottauquechee River.

Woodstock VT: $795,000      [ 11 Extra Photos ]
4508 Peterkin Hill
Enjoy spectacular sunsets and long range westerly views of Killington and the Green Mountains. High level of finish throughout - mouldings, granite counters, tile, hickory floors. Maple lined Drive. Stone Walls. Includes 3 stall barn, fenced pastures and round pen. Expansion for additional 800+ sg ft of living space on 2nd floor. Like New

Woodstock VT: $875,000      [ 11 Extra Photos ]
6106 Kendall Road
Merrily Farm- Charming classic stone cape nestled in the heart of horse country near the hamlet of So. Woodstock. A beautiful setting surrounded by meadows and lovely perennial gardens. This property features a large 5 stall barn w/loft, 4 pastures, heated studio w/3 bay car garage. The interior- 3 FP, spacious rooms w/handsome wide pine floors.

Woodstock VT: $1,500,000      [ 9 Extra Photos ]
4402 Cloudland Road
Minutes from downtown Woodstock at the bottom of Cloudland Road.3 Bedrooms,3 1/2 baths. Open floor plan around fieldstone chimney serving fireplae & woodstove. Large triangular kitchen counter/cooktop/bar creates amiable atmosphere in this spacious area. Efficient. Warm wood, tiles and slate. A/C, Brook, Private, View, Sunny

Woodstock VT: $1,295,000      [ 11 Extra Photos ]
8104 Thomas Hill Rd
Thomas Hill Farm consists of a fully renovated, spacious 1872 farmhouse with spectacular barn conversion guest house (5 rooms/1 BR/2 BA) set on rolling lawns with ancient maples, mature apple trees, beautiful landscaping, stone walls and terraces. Abutting 158 acres of conserved property, nearby the national park, and just 1 mile to Village center