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Land for sale in Chester Vermont

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$5,500,000 1,919.37 acres 6 Beds | 5 Baths | 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.
$1,550,000 118 acres 6 Beds | 5 Baths | 4931 sqft
2356 Lovers Lane, Chester, VT 05143 - Windsor County

118 acres Chester, VT

This 118 acre farm in Southern Vermont has been carefully managed as a family retreat providing complete privacy, and excellent views. The property includes a c1819 brick farmhouse with 4,930 square feet and 6 bedrooms surrounded by stonewalls and beautiful birch trees, a 2-bedroom guest house, 2-bedroom caretaker house, and two antique barns. The diverse landscape includes open meadows suitable for agriculture, a 2-acre pond, orchard and streams. Located just 4 hours from NYC, and 2.5 hours from Boston. Additional land available, see MLS 4507606.
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$599,999 193 acres 6 Beds | 4 Baths | 4316 sqft
1328 Chandler Road, Chester, VT 05143 - Windsor County

193 acres Chester, VT

REDUCED $50K!!! This Contemporary Sanctuary situated on 193 acres of open meadow, hard and soft woods, a year round brook, blue berry bushes, beautiful perennials and a swimming pond, is the perfect Vermont escape. Take in long distance mountain views through the open meadows to include Hawks Mountain. The industrious barn is built for any type of work imaginable with 3 phase power. Relax on the spacious deck over looking the pond taking in spectacular views. The open living concept, exceptionally large, flooded with natural light, unique stone and wood fireplace, and natural stone floors through out. Soap stone counters and farmers sink high light the kitchen with commercial grade stainless steel appliances. This home is in need of some fi
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$484,000 41.24 acres 3 Beds | 3 Baths | 4284 sqft
147 Mineral Springs Road, Chester, VT 05143 - Windsor County

41.24 acres Chester, VT

Perched high on a hill with sweeping panoramic mountain views to include Okemo is this custom contemporary home. The kitchen boast wood cabinetry, stainless appliances and granite counters. Large bedrooms, to include the master suite with adjoining hot tub room with one of many hand painted murals. The Greatest of great rooms is a wide open concept of the dinning, living and wet bar with sitting area flooded with natural light from many large Anderson windows and sliders. Enhanced with wood floors, exposed beams, tongue and groove wood cathedral ceiling and beautiful stone fireplace. Above the loft area 16x25 with natural wood stairs and railings. The downstairs is a blank canvas of 3,500 sq ft of wide open space. This exceptional home is e
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$449,000 170 acres 4 Beds | 2 Baths | 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
$425,000 1.56 acres
7 Pine View Drive, Chester, VT 05143 - Windsor County

1.56 acres Chester, VT

In 2007, Artists built an incredible 3,000 sq ft building on 103 South in Chester, Vermont. They chose this location for their business because of it's hometown location flavor as well as it's placement on one of the most traveled roads in southern Vermont. The building, designed by architect Dan Ferguson , was designed for multi-purpose use. Recently a 25 seat cafe (Green Leaf Cafe), was added to the mix. A portion of the building is also permitted for classes or large gatherings. The owners would like to see the building and property used to promote Crafts and Arts as well as other community orientated, cooperative, and nonprofit ventures. The property is for lease or for sale for this type of venture. We look forward to yo
$359,900 6.41 acres 3 Beds | 2 Baths | 1100 sqft
1438 Lover's Lane, Chester, VT 05143 - Windsor County

6.41 acres Chester, VT

Quality built home perfect for retirement/gentleman's farm or hide-away. Located on picturesque Lover's Lane. At the top of the knoll, you will enjoy a private country setting on a lovey country road, while being only minutes to the Chester Village. This home has so many extras, it is impossible to list them all. Maximum insulation, Geothermal system with radiant heat and full AC. Easy keeper and amazingly efficient with very affordable monthly expenses year round. Only the finest construction materials used, custom kitchen and baths. Full walk out basement for expansion. Septic permitted for 3 bedrooms, but the owners enjoy 1 level living with a large master suite. Open concept with mud room and 3 season porch. Take in the beautiful
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$349,000 90 acres 2 Beds | 1 Bath | 550 sqft
159 Murdock Road, Chester, VT 05143 - Windsor County

90 acres Chester, VT

Fishing, hunting, birding, relaxing, outdoor recreation, you name it....this private piece of land is like your very own wonderland. Amazing views, frontage on the Williams River that is known for it's hot spots! A renovated Single wide is on the property currently and it is utilizing the drilled well, power and septic ( for 4 bedroom home). High speed internet is also on site! If removed from Land use, buyer to pay penalty.
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$349,000 90 acres
159 Murdock, Chester, VT 05143 - Windsor County

90 acres Chester, VT

Big views of valleys and mountainsides from this private piece of land. Build your dream home, be it an incredible vacation retreat, primary estate or hunting preserve. A drilled well, septic for 4 bedroom home, electric and internet is on the site. Fronts on the Willimas River which is known for it's hotspots! If removed from Land use, buyer to pay penalty.
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$335,000 5.1 acres 5 Beds | 5 Baths | 3800 sqft
514 First Avenue, Chester, VT 05143 - Windsor County

5.1 acres Chester, VT

EXCEPTIONAL CHESTER VILLAGE HOME on 5+ ACRES! Handsome brick home offering 5 bedrooms, 4 baths, wide board floors, fireplaces, 2 car carriage barn. Large barn plus 3 acre meadow with river frontage. Would make an ideal horse property. Nice country feel with village amenities!1 bedroom, 1 bath on 1st floor wing, with separate entry, set-up as an in-law apartment.
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$300,000 17.43 acres 3 Beds | 4 Baths | 3314 sqft
343 Snell Rd., Chester, VT 05143 - Windsor County

17.43 acres Chester, VT

Quality Contemporary 3 bedroom, 4 bath log home on 17.43 +/- acres in wooded, private setting. Living room with cathedral ceiling and soaring two story granite fireplace. Spacious Master bedroom with granite gas fireplace and luxurious Master Bath w/corner vanity and whirlpool tub. Other features include country kitchen, finished basement with tile floor, large family game room, 3/4 bath, and two rooms for guests or office space. Outstanding value, close to skiing.
$299,000 2.48 acres 5 Beds | 3 Baths | 2587 sqft
301 Remington Road, Chester, VT 05143 - Windsor County

2.48 acres Chester, VT

Well designed & built colonial ski house, c.2008, close to Chester village and I-91 exit 6, within easy driving distance to several ski areas. So fully furnished all one would need is a toothbrush and skis for a wonderful vacation. Cherry floors set the tone for this meticulously maintained home. Four bedrooms & bunk room can sleep 12 comfortably. Two full and one half bath make mornings a breeze. The Master Suite has an over-sized bath and walk-in closet. The kitchen boasts stainless steel appliances, composite counter tops and an island. There is a Family room in the basement for a second entertainment space. Come take a look at this wonderful offering, priced to sell at below town assessment. The owners have enjoyed this property
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$298,000 5 acres 4 Beds | 3 Baths | 2348 sqft
501 Marc's Drive, Chester, VT 05143 - Windsor County

5 acres Chester, VT

SIGNIFICANT PRICE REDUCTION! Snowmobile from your property. Discover the beauty of Chester. Great restaurants, pizza, pubs and community. A choice of ski mountains within minutes. Recently renovated spacious home is move-in ready! The first floor has an updated eat-in kitchen with birch cabinets and new appliances. The living and dining rooms have refinished maple flooring. The updated powder room and laundry room are just off the kitchen. The family room with wood-burning fireplace completes the main level. The upper level has four bedrooms including a master suite and a shared hall bathroom. All bedrooms have new carpet. The bathrooms have new tubs, tile, and more. There is a fresh coat of paint throughout. The attached two-car garage ha
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$274,700 12 acres 3 Beds | 3 Baths | 1872 sqft
590 Gould Road, Chester, VT 05143 - Windsor County

12 acres Chester, VT

This Northeast Log home is located readily to Chester, Ludlow, and Springfield, and enjoys an exceptional piece of land. A beautifully appointed country kitchen is open to the formal dining room. The living room is accentuated by the field stone fireplace and is open to the den for relaxation in style. The second floor enjoys a large master bedroom with a bath. Two additional bed rooms as well as a computer study area completes the space. Linger on the farmers porch and enjoy the peace of the country. The large open yard is lovingly landscaped with ponds, outstanding gardens, fruit trees, and out buildings for equipment, as well as animals. The basement enjoys a fabulous workshop area with a garage door opening for projects and ease of a
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$259,000 2.1 acres 5 Beds | 3 Baths | 3736 sqft
501 Main Street, Chester, VT 05143 - Windsor County

2.1 acres Chester, VT

Remarkable piece of history. This brick colonial farmhouse has been lovingly maintained and has a story to tell! Big beautiful rooms, with period details in place. Original flooring, trim,doors, windows and charm! Well equipped and welcoming, the rooms are ample and the home offers 5 bedrooms and 3 full baths. Property includes a secret pine nave through the property's meadow. Stroll down the raspberry-bordered path to the banks of the Williams river. Large hay barn, covered parking, fun outdoor space to socialize or sit quietly for a bit in the private shelter. The home has two living rooms with fireplaces and a formal dining room large enough to seat a big crowd. No question that the kitchen is the heartbeat of the home....from the moment
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$225,000 4.2 acres 3 Beds | 3 Baths | 1800 sqft
833 Lovers Lane Road, Chester, VT 05143 - Windsor County

4.2 acres Chester, VT

Unwind from the hustle and bustle of metro life by absorbing Vermont's beauty in this hillside contemporary overlooking the Lovers Lane Brook and surrounding forest. Multi-level layout with spiral stairs to Master suite with skylights, cathedral ceiling, pellet stove in living room, multiple decks and a detached finished 3 season studio with a/c! Across the road are two heated, two car garages with paved driveway! Rustic touches with modern convenience. Professionally landscaped with numerous perennial plantings including blueberry bushes! Turnkey investment property for ski/summer rentals. Close to snowmobile, hiking trails & town rec area.
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$220,000 4.6 acres 2 Beds | 2 Baths | 2160 sqft
87 VT Rte. 103 North, Chester, VT 05143 - Windsor County

4.6 acres Chester, VT

This lovely 8 year old modular home offers a great 4.60 acre lot close to the stone village and a short walk to the center of town. Offering a large eat-in kitchen with plenty of cabinets, expansive granite counter tops and adjacent to the formal dining room which offers great natural light. Entertain family and friends in the spacious family room or relax in the living room. The main level also enjoys a 1/2 bath with laundry, large foyer with wood stove and entrance out to the two bay attached garage.Head upstairs and you will find a cozy landing perfect for a sitting area or small office space. The master bedroom is massive and could potentially be split into a third bedroom. With private balcony that walks down the back deck and a large
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$219,000 14 acres 5 Beds | 2 Baths | 2668 sqft
228 North Street, Chester, VT 05143 - Windsor County

14 acres Chester, VT

Located in the historic Stone Village district of charming Chester this 5br 2 ba home is ideally suited for the horse lover or gentleman farmer with a 45 x 34 barn situated on 14+/- acres. Country style kitchen, large dining and living rooms with lots of storage space. Some upgrades completed and ready for your personal touches. Close to many major ski areas. Priced way under assessed value for a quick sale. Come take a look.
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$217,000 2.1 acres 3 Beds | 3 Baths | 2600 sqft
855 Marcs Drive, Chester, VT 05143 - Windsor County

2.1 acres Chester, VT

A 10 year old cape style home set on 2.1 acres less than 2 miles to the center of the Town of Chester. The house is near the end of a well maintained town road in a pet friendly and quiet location with beautiful landscaping which you will enjoy relaxing out on any one of 4 different decks. You can enter through the lower entrance into a partially finished basement with lots of storage and is heated by a pellet stove providing for warm first floor floors in the winter. Or you can enter thru the upper first floor entrance into a spacious, open concept first floor with a living room, dining room, kitchen and a half bath with laundry. The first floor offers a spacious master bedroom with a full bath with double sinks and linen closet. Upstairs
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$167,500 4.63 acres 2 Beds | 1 Bath | 868 sqft
314 VT Route 10, Chester, VT 05143 - Windsor County

4.63 acres Chester, VT

EXCEPTIONAL..PRISTINE..FURNISHED.. 2BR Home, ideally located only minutes from Okemo Mtn, lakes, golf, snowmobiling & other recreational activities. This home is easily accessed in all seasons & only 20 min. from I-91. Equipped with a standing seam roof, relatively new carpeting, granite composite sink & counter top, new refrigerator & other amenities. If you are just looking to kick back & enjoy a country atmosphere, then there are two decks & one comes equipped with a hot tub. If this sounds right for you, then schedule a time to see what this home has to offer..
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$125,000 11.22 acres
00 Trebo, Chester, VT 05143 - Windsor County

11.22 acres Chester, VT

Improved 11 acre building lot with incredible views to the east. Drilled well on site and waste water design permit. House site is cleared and partially dug and survey is available. Wooded lot offers privacy with mountain views. Ready to build your dream home!
$119,000 2 acres 4 Beds | 1 Bath | 1632 sqft
125 Whitmore Brook Road, Chester, VT 05143 - Windsor County

2 acres Chester, VT

Tucked away on a quiet town road between Chester and Ludlow is this 4 bedroom home with lots of natural light, wood floors and open beams. large open floor plan downstairs with a big newly remodeled and applianced kitchen, dining area and large living room with a stone hearth and gas burning stove. Enjoy the 2 +/- acres with an ample yard, matured landscaping & wooded trails. Poured slab for a garage. Would make a great ski house only 6 miles to Jackson Gore/ Okemo... don't miss this one!
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$109,000 4.99 acres 3 Beds | 1 Bath | 1438 sqft
159 River Street, Chester, VT 05143 - Windsor County

4.99 acres Chester, VT

Investors and contractors take note. This great in-town 4.99 acre lot has an antique farmhouse and huge potential with a large lot fronting on 3 roads. Find a roomy kitchen, dining room, living room, den and a full bath. There is also an attached work shop. The upstairs offers a great bonus room that could work well as a game room or large office as well as three plus bedroom. The one bay garage with a covered carport is great storage. The large level yard is perfect for gardening or whatever your imagination can think up. The hearty blackberry bushes are a sweet treat in the summer months. Convenient in-town living, just a short walk to the village. This home is ready and waiting for your big hug!
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$82,500 2.5 acres 1 Bed | 1 Bath | 600 sqft
106 Hall Rd, Chester, VT 05143 - Windsor County

2.5 acres Chester, VT

Back on the market and price reduced! 1 bedroom, 1 bath cottage on 2.5 acres on dead end road. Great getaway for 1 or 2 people on wooded lot within easy access to Springfield and Chester. Close to skiing. Renovated stylishly, with hobbit-like details, a perfect pied-a-terre for skiing, antiqueing, or just relaxing!
$69,900 44 acres
621 VT RT 10, Chester, VT 05143 - Windsor County

44 acres Chester, VT

Large 44 acre+/- parcel within easy driving distance to skiing and shopping. Clearing for driveway in place, power pole on site where a mobile home was once located. Potential for bigger views and more privacy if house is sited further in and up. Nice Southern Exposure. Property has been logged but may still be eligible for Current Use program.
$59,950 2.34 acres
Lot 1 Vt Rt 103 S, Chester, VT 05143 - Windsor County

2.34 acres Chester, VT

Incredible building opportunity on a great 2.34 acre lot with over 500 feet of road frontage. Already permitted for a 3 bedroom home with 30' x 60' shop, perfect for builders, electricians or similar trades with great road exposure! Come take a look today!
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$59,000 19.5 acres
0 Lovers Lane, Chester, VT 05143 - Windsor County

19.5 acres Chester, VT

Lovely, wooded Chester location with a total of 19.5 acres +/- on a winding, country road with frontage along the Lovers Lane Brook. Site your home close to the road or high on a knoll for optimum privacy and southerly exposure. Good location for solar power and/or off the grid lifestyle. Soil tests on 9.42 acre parcel indicate several building spots. Adjacent lot with 10 acres included for protection and recreational use. Great area for mountain biking, hiking, kayaking, skiing and snowmobiling. Close to town Recreation area with pool, tennis courts & skateboard park. Near town forest, walking trails, and within 15 min. to skiing. Motivated Seller, price reduced, encouraging offers.
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$39,900 4.7 acres
1 Fenton Road, Chester, VT 05143 - Windsor County

4.7 acres Chester, VT

This 4.7 acre lot is ready to build on! Great spot for a vacation home or primary home! Easy access, beautiful year round brook on the property, septic design completed and just short drive into Chester Village.This lot is truly a "hidden" treasure! Have a look for yourself....maybe this spot is what you have been looking for!
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$36,900 5.8 acres
lot #7 Davidson Hill Rd, Chester, VT 05143 - Windsor County

5.8 acres Chester, VT

Only 1/3 mile off of pavement on a pretty gravel town road. Lightly wooded, sloping, with septic design for a mound system. Possible views with clearing. Utilities at roadside, easy access from road into land.