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Homes for sale in South Vermont - Page 1 of 25

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$1,200,000 175 acres 4 Beds | 1 Bath | 4399 sqft
3400 VT- 133, Ira, VT 05777 - Rutland County

3400 VT-133 - Ira

The understated approach to the Teaberry Estate of Ira, VT conceals an expansive property built with elegant craftsmanship & functional design. The sprawling 175+/- acres is free of private & government easements, zoning & anything hindering your vision. The extremely private elevated home site is designed to compliment the surrounding natural beauty & accentuate stunning mountain views. Entertain friends on the 2 level patio offering a screened gazebo, towering fireplace & delightful waterfall. A sophisticated design continues inside; natural light washes over marble, limestone & hardwood floors. Granite counters & exquisite maple finish work sourced from the property. 4 bedrooms & 5 baths include a master s
Curtis Trousdale Preferred Properties
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$895,000 101 acres 6 Beds | 4 Baths | 7902 sqft
1037 Bailey Road, Shrewsbury, VT 05738 - Rutland County

1037 Bailey Road - Shrewsbury

Highfields Farm has been extensively renovated and expanded over the years, not only to preserve its historic character, but to meet and exceed the expectations of the modern family. This 7,902 square foot home features six bedrooms and seven baths, showcasing its ability to host family and friends, further emphasized by the oversized gourmet kitchen, generous rooms and spacious three story guest wing. The stone patio, featuring an outdoor stone fireplace, is a tremendous place for cocktails with guests while soaking in the stunning long range mountain views. Situated on 101+/- acres, there is plenty of space for activities over the diverse landscape of pastures & woodlands. In addition, the home site includes a pond, charming landscapi
Curtis Trousdale Preferred Properties
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$620,000 160.52 acres 2 Beds | 2 Baths
389 Denning Road, Randolph, VT 05061 - Rutland County

389 Denning Road - Randolph

Welcome to the 160.52 +/- acre Sundog Estate! Take a drive up this tree-lined road opening up to magnificent views of the Tunbridge Hills. Approaching the home, you’ll notice your beautiful lower fields with private gardens and fruit trees. Continuing along your driveway, observe your 2,172 sqft home displaying a balcony, expansive windows and elegant, authentic character.  Cool down and enjoy a swim in your private pond, or lay in the sun on your floating docks. Spend time manicuring your berry trees or strolling through the matured-hardwood forest surrounding the upper and lower fields. This is an unbelievably well-maintained property with plenty of trails throughout, a beautiful stream onsite, extensive space, and pristine views. In addi
Curtis Trousdale Preferred Properties
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$575,000 245.5 acres 3 Beds | 1 Bath | 1838 sqft
Plymouth, VT 05056 - Windsor County

881 Johnson Farm Road - Plymouth

Peace and quiet is only the beginning at the Berry View Estate located in Plymouth, VT. Your destination for relaxation and recreation on 245+/- acres and contiguous to the 21,500 acre Coolidge State Forest! A well-kept driveway winds through the lower forestland to the cleared and elevated home site where a modern three bedroom, two bath log home is perched offering stunning panoramic mountain views. Home includes all modern amenities like power, phone, TV & high speed fiber internet. Hike, snowshoe and ski the many trails throughout the well managed forest. Large clearings offer successional wildlife habitat with endless raspberry and blackberry bushes. Hunters will appreciate the abundant moose, deer and grouse along with the clover
Curtis Trousdale Preferred Properties
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$549,000 98.16 acres 3 Beds | 1 Bath | 1200 sqft
2999 Baltimore Road, Baltimore, VT 05143 - Windsor County

98.16 acres Baltimore, VT

This property is stunning. Not for the "faint of heart". Follow a long winding driveway up to the top of the world...or so it seems. Breathtaking views sweep across the landscape for miles on end. This adorable "cabin" is a nice 3 bedroom home with septic and well in place. Electricity is up the mountainside....all the modern conveniences are at your fingertips. Quiet as quiet can be and restful for the weary, this spot cannot be beat. If you are not prepared to pay, you may want to stay away, because you just won't want to leave! There will be no comparable sold properties...they just don't exist! Simply amazing. Abundant wildlife to watch. At night, you can see the lights from Stratton Mountain to New Hampshire mountain ranges. Words cann
Rebecca Sanford Walnut Hill Realty, LLC
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$475,000 59 acres 3 Beds | 2 Baths | 2276 sqft
260 Dan Jarvis, Weathersfield, VT 05030 - Windsor County

260 Dan Jarvis, Weathersfield

Welcome to the Stone Hearth Estate! A country lifestyle property focused around a beautiful & spacious 2276 SF New England style Cape, gorgeous Mount Ascutney views & privately situated on 59+/- acres of hardwood forest in Weathersfield, VT. Workshop or farming enthusiasts will covet the spacious clear-span heated workshop, quaint animal barn and sugarhouse with 500 potential taps (not currently used). Home features pine floors sourced from the property, wood timber frame accents & a stone hearth built from the foundation of the original farmhouse. All this adds amazing character to this 3 bedroom, 2 bath home. Enjoy an oversized first floor master with private balcony & whirlpool tub. Exquisitely landscaped with fruit trees
Curtis Trousdale Preferred Properties
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$449,000 170 acres 4 Beds | 2 Baths | 1 ½ Bath | 2620 sqft
2319 Vt Route 11, Chester, VT 05143 - Windsor County

170 acres Chester, VT

Kingdom Valley Farm. Enjoy a visit to this beautiful antique farm house with graceful pillars greeting you as you arrive.All the original detail you are seeking mixed with the modern conveniences we need!Large open living area encompasses the country kitchen, dining room, tavern area and parlor.Big pantry, office and family room also on the first floor. Large bedrooms, high ceilings and beautiful wood floors at the top of the stairs.Big closets, nooks and crannies everywhere, built-ins a bunch! Passers-by in the springtime enjoy the line of lilac bushes that shield the farm house from the road. It is a hallmark of this farm for as long as most of us can remember! Tall maples provide privacy and surprisingly traffic noise is minimal at this
Rebecca Sanford Walnut Hill Realty, LLC
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$344,900 10.06 acres 3 Beds | 3 Baths | 2294 sqft
105 Atcherson Hollow Road, Rockingham, VT 05143 - Windham County

10.06 acres Rockingham, VT

A picture is worth a thousand words! This beautiful contemporary cape with 5 garages, paved drive, a view that just doesn't get any better, upgraded kitchen and baths, sun room and deck with a top of the line Otter Creek retractable awning, landscaping that includes a beautifully built bridge (over the babbling brook!) that is on National Registry of Romantic Bridges and VAST access are just some of the amazing qualities of this home! From the moment you walk in the door, you will be charmed by this home! Quality built with all of the comforts and amenities you could ask for, including central air and a full house generator. Amazing offering just waiting for you.
Rebecca Sanford Walnut Hill Realty, LLC
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$299,000 23 acres 6 Beds | 3 Baths | 2700 sqft
44 Bisbee Road, Springfield, VT 05156 - Windsor County

23 acres Springfield, VT

Steeped in history is this remarkable, antique brick federal home with 23 pastoral and wooded acres. The property offers multiple outbuildings including a 30x40 barn with 6 box stalls, hay lofts, electricity and water. Amazing views plus the charm and comfort only found in older homes and privacy at the end of a town maintained road. Enjoy the in-ground swimming pool and sauna. The land offers views from every angle, as well as high-bush blueberries, and wild grapes, strawberries and black raspberries. Close to highways, vast trails, ski areas and an easy distance from downtown. Every window is a frame for an amazing view. This value can't be beat. We invite you to take a look! You won't be disappointed!
Rebecca Sanford Walnut Hill Realty, LLC
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$99,000 2.4 acres 2 Beds | 1 Bath | 1200 sqft
363 Piper Hill Road, Weston, VT 05161 - Windsor County

2.4 acres Weston, VT

Ideal Weston location on over 2 acres of mostly meadow. The house has been well maintained and has known lots of love over the years. Good times have been enjoyed by many over the generations. This home is being offered without the two additional rental cabins (will be removed by seller prior to closing). Desirable location makes this an excellent choice for either a primary home (school choice!) or a vacation get-a-way! Enjoy all that Weston has to offer you in the summer (Weston Play House) and come winter, it is a short distance to multiple ski areas. Truly a four season location! Easy to show.
Rebecca Sanford Walnut Hill Realty, LLC
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$499,000 60 acres 3 Beds | 4 Baths | 1 ½ Bath | 3033 sqft
251 Youlin Rd, Rupert, VT 05776 - Bennington County

60 acres Rupert, VT

Set privately back on /-60 acres of wooded land and gorgeous rolling meadowland is this 3 bedroom, 3 bath , beautifully built and maintained (1998) home. The setting is incredible with /-25 acres of open meadowland great for horses, etc., and the balance in woodland with a brook and pond. The home takes full advantage of the setting with beautiful distant views overlooking the property. Great living space with open kitchen and dining area with french doors to the deck with awning that overlooks the pond. The living room has lots of glass, soaring cathedral ceiling and massive stone fireplace impressive. Other amenities include 1st floor master suite, 28x28 attached heated garage, laundry/mud room with tile floor, skylights and det
Scott Mcchesney Lee D. McChesney Real Estate
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$369,000 8.3 acres 4 Beds | 3 Baths | 1 ½ Bath | 2850 sqft
287 Andrus Drive, Pawlet, VT 05761 - Rutland County

8.3 acres Pawlet, VT

Set up off a dead-end town gravel road on /- 8 1/4 acres with beautiful southern exposure and views (to Mount Equinox!) is this c1983 4 bedroom, 2 1/2 bath home. The home takes full advantage of the magical setting with a marble sunroom (great solar gain), large porch and the master bedroom all taking in this incredible view overlooking your gorgeous, deep (swim) pond and protected land beyond (Vermont Land Trust). Great rustic charm throughout with exposed timbers and wood floors, and great space with 2 large living areas, a dining room and spacious/open kitchen, and of course, the marble sunroom! Other amenities include mud/laundry room, attached 2 car garage, wood/oil furnace, walk-out basement, 5 bay equipment barn, year round brook
Scott Mcchesney Lee D. McChesney Real Estate
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$319,000 37.32 acres 3 Beds | 3 Baths | 1 ½ Bath | 2783 sqft
488 Betts Bridge Rd, Pawlet, VT 05761 - Rutland County

37.32 acres Pawlet, VT

Set on 37 Acres - mostly wooded with seasonal stream and pastureland, this artfully designed, passive solar, sun-filled home exudes warmth.Home has old brick and cherry floors, exposed beams and lots of windows. You enter from a brick side porch to an impressive 22x30 great room with a 13 window seat, wood stove w/ hearth, plant bench/greenhouse area, open kitchen w/ walk-in pantry and wonderful outdoor space including 2 screen porches and a large full wrap-around whole house deck. Finishing off the downstairs is an entry/mud room and utility room, 1/2 bath and master bedroom suite w/ its own glass porch, walk-in closet with separate cedar closet and laundry room plus full bath. Up are 2 large bedrooms, with window seats taking in the incr
Scott Mcchesney Lee D. McChesney Real Estate
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$299,900 2.75 acres 4 Beds | 3 Baths | 1 ½ Bath | 2900 sqft
315 Maple Grove, Pawlet, VT 05761 - Rutland County

2.75 acres Pawlet, VT

State of the art efficiency: 4 cold climate split heat pumps for heating and cooling. Solar panels (9.35 net meter) for electric storage with Green Mountain power. Viessman oil boiler for baseboard and radiant heat and 80 ga electric heat pump hot water heater. Incredibly efficient and majority powered by the sun! 26x36 2 floor barn/garage, 3 bay and would make an incredible shop! Beautiful, private and quiet (dead-end private road) level yard backing up to forest and farm land. Nice outdoor space with full length front porch and large patio. 1/5 ownership/interest of over 12A of open/common land. Inside enjoy great living space with wood and tile floors and new carpeting. Large family room and vaulted ceiling sun room with wood
Scott Mcchesney Lee D. McChesney Real Estate
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$299,000 4.89 acres 5 Beds | 2 Baths | 2900 sqft
2812 VT Rte 30, Pawlet, VT 05761 - Rutland County

4.89 acres Pawlet, VT

Nestled back off the road for total privacy in a park-like setting is this c1800 5 bedroom, 2 full bath home. The great outdoor space with slate terrace, 11x23 deck and 12x21 three season porch takes nice advantage of the westerly views over the Mettawee River and the lovely grounds with flower beds and apple trees. The spacious living area includes large eat-in kitchen, formal dining room and large "L" living room with slate fireplace. Upstairs contains the 5 bedrooms and a small office. Other amenities include walk-in pantry with original cabinets, beautiful wood floors throughout, laundry room, mudroom, attached 2 story, 2 car garage and 2 small outbuildings. The well maintained house has been updated over the years. A very special
Scott Mcchesney Lee D. McChesney Real Estate
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$249,900 55.56 acres 3 Beds | 2 Baths | 1650 sqft
342 High Chapparal Road, Wells, VT 05774 - Rutland County

55.56 acres Wells, VT

Set way back off a town gravel road on 55 acres is this 2001 built 3 bedroom, 3 bath home with an incredible 38x48 shop/garage space. Set up high with total privacy and beautiful views this spacious home and shop sits on the edge of a several acre meadow with balance in woods- great for small farm, hunting or just enjoying the quiet and playing. (Test pits have been done and are promising for additional home site if desired) Currently, the finished living space, including open kitchen/dining/living and 3 bedrooms is all on second level while the spacious shop/garage is ready for tractors, snowmobiles and ATV's to play!
Scott Mcchesney Lee D. McChesney Real Estate
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$249,500 6.88 acres 3 Beds | 2 Baths | 2500 sqft
6885 Route 153, Rupert, VT 05768 - Bennington County

6.88 acres Rupert, VT

Set along a winding county road on nicely varied land with a pond. Beautiful valley views, stone walls, woods, open hillside pasture, pretty yard with gardens and apple trees and the Indian River right across the road. Spacious house with large LR with brick FP, kitchen with island, formal DR with sliders to screened porch and patio. 3 BR and huge 18x30 studio space (or MA BR) over the attached 2 car garage. Other amenities include separate garden shed with electricity, propane generator automatic back-up system and covered slate walkway/breezeway. Newer furnace, new tile bath, interior paint and more- shows well! Great location. Mettawee school district.
Scott Mcchesney Lee D. McChesney Real Estate
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$249,500 10 acres 3 Beds | 2 Baths | 1800 sqft
2878 Tinmouth Road, Danby, VT 05739 - Rutland County

10 acres Danby, VT

Set privately off a quiet country town road on /- 10 Acres is this c2001 built 3 bedroom, 2 bath log home. Great living space with newly remodeled (all new appliances) eat-in kitchen, cathedral ceilinged living room with Jotul wood stove with hearth/stonework, plus formal dining room with french doors to huge deck taking in the views. Finishing off the downstairs is a master bedroom with walk-in closet and 3 season porch plus newly done full tile bath. Upstairs are 2 cathedral ceilinged bedrooms and a full tile bath with jacuzzi tub. Amenities include full basement with laundry room plus 2 car garage, Buderus boiler and 10A of mostly woods with frontage on Baker Brook.
Scott Mcchesney Lee D. McChesney Real Estate
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$199,500 6.73 acres 2 Beds | 2 Baths | 1 ½ Bath | 1530 sqft
1896 Lilly Hill Rd, Danby, VT 05739 - Rutland County

6.73 acres Danby, VT

Perched up on a knoll off a town gravel road amidst beautiful gardens and fruit trees offering privacy and tranquility is this charming 2 bedroom cape on 6 acres. This classic cape has an eat-in kitchen, formal dining room, spacious living room with fireplace, den/office and 1/2 bath on the first floor and 2 large bedrooms and full bath up. The land is comprised of the magical gardens to be enjoyed from the brick terrace with the balance in hardwood (nice sugarbush for the sugar maker). There is even a garden shed for the lawn tractor. A beautiful home and setting in a great location and a super value!
Scott Mcchesney Lee D. McChesney Real Estate
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$197,500 10 acres 4 Beds | 3 Baths | 1 ½ Bath | 2058 sqft
2804 Tinmouth Rd, Danby, VT 05739 - Rutland County

10 acres Danby, VT

Easy living is affordable with this 4 bedroom 2 1/2 bath one level home set way back from the road with nice meadowland and hardwoods leading back to a year round stream. Recent improvements include new roof (2012), new furnace (2013) a wood and pellet stove (2011) and antique Crawford cooking stove gracing the kitchen. Two outbuildings, including sizable garden shed and 2 stall horse run in barn. Very well priced, well under the assessed value at only $197,500
Scott Mcchesney Lee D. McChesney Real Estate
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$159,500 4 acres 5 Beds | 2 Baths | 2250 sqft
2736 Route 153, Pawlet, VT 05775 - Rutland County

4 acres Pawlet, VT

Set up from the road in the heart of West Pawlet Village on /-4A is this early 1800's 4-5 bedroom home. With over 2A of open fenced meadow and a small barn with run in shelter it's all ready for the chickens and horses to move in! (Great riding on the Rails to Trails trail across the road). The 1800's home with 1970's addition has great space- Eat-in kitchen with pass thru to large den/office, spacious living room with fireplace, formal dining room with french doors and original wide plank floors, 3/4 bath and entry mudroom. Upstairs are 4-5 bedrooms and a large full bath with laundry hook-up. A very rare and special offering. Live in town and out in the country all in one! And at a great value at $159,500! Additionally there is a larg
Scott Mcchesney Lee D. McChesney Real Estate
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$6,900,000 468.36 acres 5 Beds | 4 Baths | 1 ½ Bath | 4165 sqft
2358 Long Hill Road, Woodstock, VT 05071 - Windsor County

468.36 acres Woodstock, VT

The 468-acre Birch Tree Farm is an unparalleled family recreational retreat offering privacy and a vast array of activities within eight miles of Woodstock. The five-bedroom main lodge offers a generous open floor plan with a well-appointed kitchen and a great room featuring an impressive floor-to-ceiling fieldstone fireplace and tall windows framing the Ottauquechee River Valley. An expansive deck faces the view overlooking the infinity pool, stocked pond, apple orchard and meadow. The three-level bank barn is finely finished in fir, oak and pine with 7 box stalls on the first level, and an extraordinary recreation and media room on the 2nd level. Miles of carriage-width trails connect to the GMHA trail networks, and to the top of 2,409 fo
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$5,500,000 1,919.37 acres 6 Beds | 5 Baths | 1 ½ Bath | 4931 sqft
2356 Lovers Lane, Chester, VT 05143 - Windsor County

1,919.37 acres Chester, VT

This 1,929 acre farm in Southern Vermont has been assembled over 40 years and carefully managed as a family retreat providing complete privacy and excellent views. The property includes a c1819 Farmhouse with 4,930 s.f. and 6 bedrooms, Guest House with 2 bedrooms, Caretaker House with 2 bedrooms, 2 Antique Post & Beam Barns, and a secluded Log Cabin. The diverse landscape has 60 acres of meadows suitable for agriculture, a stocked 2-acre pond, orchards, streams, and 3.5 miles of top grade access roads throughout the property. The 1,839 acres of carefully managed northern hard wood forest, predominate in Sugar Maple, has a Timber Capital Value estimated at $2.67M. Located 4 hours from NYC, and 2.5 hours from Boston.
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$4,900,000 128.06 acres 8 Beds | 10 Baths | 2 ½ Baths | 9587 sqft
1095 Eastman Road, Sharon, VT 05065 - Windsor County

128.06 acres Sharon, VT

EASTAWAY ESTATE - The breathtaking Eastaway Estate sits on 128 acres tucked away on a mountainside at the end of a gated private drive. Theelegant main residence and guest house are perched at an elevation of 1,400 feet overlooking the Green Mountains,creating the ultimate country escape. The sophisticated contemporary homesofferthe highest quality materials including mahogany ceilingsand marble floors.The floor-to-ceiling windows and inviting exterior decks and terraces provide full views of the majestic professionally landscaped surroundings. An extensive trail network winds throughout the rolling, wooded property for walking,snowmobiling, cross country skiing and more. The two homes offer over 9,000 square feet of luxurious living space,
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$4,500,000 82.5 acres 4 Beds | 8 Baths | 2 ½ Baths | 6980 sqft
387 Benedict Road, Woodstock, VT 05071 - Windsor County

82.5 acres Woodstock, VT

"SUNNYSIDE" is one of the most perfectly designed and constructed brick Georgian Revival residences in New England - located on a prestigious South Woodstock hilltop on 82.5 acres, with beautiful panoramic views of the surrounding hills and offering absolute privacy. Construction was completed in 2002, with unparalleled attention to detail. And the property has been meticulously manicured and maintained. The 7,000 square foot main residence combines a formal elegance with a beautiful Vermont hilltop setting. The residence features four fireplaces, expansive living and dining rooms, a butternut paneled library, den, continuous flow swimming pool, three-story elevator and a large, beautifully appointed gourmet kitchen with adjoining pantry. T
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$4,150,000 396 acres 4 Beds | 6 Baths | 2 ½ Baths | 10256 sqft
1055 Sayer Road, Barnard, VT 05031 - Windsor County

396 acres Barnard, VT

Prominent New England equestrian estate located in the hills of Barnard, Vermont a short distance from Woodstock and Hanover, New Hampshire. Circa 1998 6800 square foot main residence with three-car attached garage and spectacular post and beam six-stall barn. 396 acres of managed pasture and forest with 13 miles of riding trails, one of which terminates at a hilltop picnic area with a magnificent 360 degree view a short half-mile ride from the barn. A 2400 square foot caretaker residence with an attached two-car garage and a beautiful seven-stall post and beam barn occupies a hilltop across the road from the main residence. Two ponds complete this perfect setting. The main residence was five years in the building by a local builder renown
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$3,980,000 948 acres 8 Beds | 7 Baths | 2 ½ Baths | 8143 sqft
1048 Black Hole Hollow Rd, Arlington, VT 05250 - Bennington County

948 acres Arlington, VT

The serene setting of Black Hole Hollow Farm in a quiet valley on the border of Vermont and New York is threaded by the White Creek brook, tiered ponds and 30 miles of trails on 948 acres. The 6-bedroom, 8,143-square-foot main house is surrounded by English-style country gardens with the mountains as backdrop. The original 1772 farmhouse was expanded and designed by noted architect Jerome Cerny. Living room, dining room and downstairs bedrooms open to the gardens and the recently updated kitchen is a welcoming hub with its AGA stove. The farm has a rich history including visits from author Ian Fleming who gained inspiration for several of his James Bond books, and former owner Josephine Hartford Bryce, heir to the A&P dynasty. There is a la
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$3,750,000 119.6 acres 5 Beds | 8 Baths | 2 ½ Baths | 6866 sqft
164 Hewitt Lane, Woodstock, VT 05091 - Windsor County

119.6 acres Woodstock, VT

A sophisticated country family retreat, Havenwood combines close-tothe-village location with end of the road privacy on 119.6 /- acres. Impeccably renovated and intelligently planned, the main house feels intimate yet expands to fit a crowd. The central open kitchen/family area is centered around a big fireplace with ample separation for a quiet study. Other gathering spaces include a beautiful screen porch and multiple outdoor terraces to enjoy the gorgeous landscape. The lower level has a fun game room as perfect recreation space that opens on to a stone terrace, and a sophisticated temperature controlled wine room. The gracious master suite is on the ground level, with 4 additional bedrooms on the second floor. The guest house-barn
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$3,200,000 566 acres 4 Beds | 8 Baths | 2 ½ Baths | 10500 sqft
89 Mountain Spring Road Road, Chittenden, VT 05737 - Rutland County

566 acres Chittenden, VT

Spectacular Mountain and Water Views / 566 Acres Adjoining The Green Mountain National Forest. Pristine, conserved property with expansive trails, wildflower meadows, orchards, ponds and forest.Exclusive use of native plants, shrubs and trees supports a large population of over 100 species of birds, butterflies, fish and wildlife. Five buildings with extensive infrastructure. Suitable for further development. Located adjacent to The Mountain Top Inn and Resort (four season resort with Nordic, lake and equestrian activities). Killington Ski resort 30 minutes away. Airport is 20 minutes away. Call for private web site link that shows the property.
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$3,199,000 241 acres 7 Beds | 6 Baths | 7945 sqft
1599 Cavendish Gulf Road, Cavendish, VT 05142 - Windsor County

241 acres Cavendish, VT

GRAHALL- A feat of architecture and engineering, this is a spectacular, one of kind estate on 240 acres in prime central Vermont. Drawing inspiration from an iconic castle on a loch, Grahall sits atop Hawk's Mountain with breathtaking views in all directions. The home was built with stunning Glimmerstone Granite that is indigenous to the area and quarried directly from the property. An incredible amount of thought and planning went into the creation of the exteriors and interiors. While the structure is commanding the interiors feel warm and embracing. Many of the gathering rooms are circular with large granite fireplaces. There is wonderful light throughout the house providing passive solar. There are 7 well appointed bedrooms and 5 baths