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Market info: Currently there are 50 Chester Vermont Single Family Residential Homes for sale with average price of $366,704    

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CHESTER VT Home for sale $$3,750,000 | $5,769 per sq.ft.

$3,750,000 | $5,769 per sq.ft. CHESTER VT HOME FOR SALE

1 Beds | 0 Baths |   Total Sq. Ft. 650  |  Acres: 1804
One of the best investments on the market today. chester forest consists of 1,803.79 acres of well-stocked and managed forest with over $2.6 million of standing timber, dominated by sugar maple. on the property is an easily accessible 650 square foot log home built in 1991 from logs harvested from the land and set in an apple orchard field with tremendous views to the southwest. See MLS Property & Listing Details & 4 images.

CHESTER VT Home for sale $$1,100,000 | $230 per sq.ft.

$1,100,000 | $230 per sq.ft. CHESTER VT HOME FOR SALE

5 Beds | 4 Baths |   Total Sq. Ft. 4786  |  Acres: 170.82
C1850’s hidden pond farm blends the classic vermont farmhouse and setting, views and privacy with tasteful renovation and addition that provide a more open floor plan. sited on 170 acres at the end of a road shared with just one other residence, the farmstead is surrounded by meadows and includes a swimming pond, 5-stall barn, detached garage and trails throughout the property. the farmhouse, with 4,786 square feet and 5 bedrooms, has a classic new england style with brick fireplaces, antique floor boards and original paneled doors. the addition’s complementary style transitions to a great room with high ceilings, big windows and mountain views. located within 3 miles of chester village and 7 miles of route 91. See MLS Property & Listing Details & 27 images. Includes a Virtual Tour

CHESTER VT Home for sale $$990,000 | $201 per sq.ft.

$990,000 | $201 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $560,000 down 57% on October 2nd 2017

6 Beds | 5 Baths |   Total Sq. Ft. 4931  |  Acres: 73.7
This 73.7 acre farm in southern vermont has been carefully managed as a family retreat providing complete privacy, and excellent views. the property includes a c1819 farmhouse with 4,930 square feet and 6 bedrooms surrounded by stonewalls and beautiful birch trees, a 2-bedroom 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. See MLS Property & Listing Details & 17 images. Includes a Virtual Tour

CHESTER VT Home for sale $$989,000 | $260 per sq.ft.

$989,000 | $260 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $111,000 down 11% on September 6th 2017

4 Beds | 4 Baths |   Total Sq. Ft. 3808  |  Acres: 245
Privacy, views, acreage and authentic vermont! this dramatic log home began in 1981 as a small classic log cabin; but the big view and setting just deserved more. between 2003 and 2008 the owner added nearly 3,000 square feet. now this lovely large home sits at the top of an open meadow easily taking in the dramatic southerly views. with 245 acres and being located at the end of the private drive, you don't have to see anything but wildlife. the newer main house features a custom-crafted entry door that was imported from belgium. it takes you in to a large entry area with an additional room just off the entry that is waiting for your finishing (a large half bath, laundry room or pantry - you decide). the kitchen features high ceilings with skylights, jenn-aire cooktop, bosch dishwasher & ge profile refrigerator, granite counters and a wood stove. just off the kitchen/dining area is a huge living room with large windows to take in the amazing views and a stone fireplace to add warmth and ambiance on a cold evening. this south-central small town of chester is just 3 hours from boston, less than 4 hours to nyc and 4 hours to montreal. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour

CHESTER VT Home for sale $$975,000 | $275 per sq.ft.

$975,000 | $275 per sq.ft. CHESTER VT HOME FOR SALE

4 Beds | 5 Baths |   Total Sq. Ft. 4044  |  Acres: 79.5
At the end of a town maintained road and minutes from okemo, this unique home offers incomparable craftsmanship and majestic views. privately situated on 79+/- acres, there is a pond, sugar house, 3+ car garage, lighted tennis court and sophisticated tree house.the kitchen is not only beautiful with cherry cabinetry, quartz counters and soapstone floors, but a cook's delight, outfitted with large subzero freezer and refrigerator, wine refrigerator, refrigerator drawers, wolf double oven and 6-burner range, blodgett salamander, warming drawer, dishwasher, compactor, and winekeeper wine dispenser. the wall of windows in the living area overlooks the pond and beyond with long range views into nh. a round dining room is surrounded in glass and features a mahogany ceiling with a grapevine detail. main floor also comprises an exquisitely detailed office, hot tub room and 2-room guest suite with kitchenette. large wrap-around deck expands the living outdoors. second floor has a grand master suite with views, sitting area, and soapstone bathroom with jetted tub and steam shower. second bedroom has a sky light, window seats and en-suite bathroom. a stairway leads up to a second office. walk-out lower level has a hobby room, wine cellar and family room with bathroom that could serve as a fourth bedroom, and plenty of unfinished space for storage. there is an attached garage, a detached 3-car garage with lift and a 18' x 36" sugar house. this property is a special find and must be seen! See MLS Property & Listing Details & 40 images.

New Listing! CHESTER VT Home for sale $$483,900 | $113 per sq.ft.

$483,900 | $113 per sq.ft. CHESTER VT HOME FOR SALE

3 Beds | 3 Baths |   Total Sq. Ft. 4268  |  Acres: 41.24
Your own piece of vermont on the top of the world! come take in all this spacious contemporary has to offer with spectacular mountain views including okemo mountain, situated just right on 41 plus acres on the outskirts of picturesque, chester, vt. travel up the private driveway and admire the handsome stonework that surrounds the house including a large stone patio perfectly placed to enjoy the views. the three car garage is perfect for all of your toys! come in the front door and take in the hand painted mural, continue on into the great room with cathedral ceilings, a massive fireplace which is the centerpiece of the home, a wet bar and floor to ceiling windows. the chef's kitchen is massive and boasts granite counter-tops, plenty of cabinetry, a warm wood stove and a lovely breakfast area. the master suite is where you might find yourself spending lots of time having access to the spa room that enjoys an in ground hot tub, perfect for relaxing after a long day on the slopes as well as large windows to enjoy the stunning view. the main level enjoys two more spacious bedrooms and two full baths. the loft has additional sleeping space for guests and overlooks the great room. this property has it all and is an exceptional value for all it has to offer. don't miss an opportunity to claim this amazing piece of vermont which is just a short distance ludlow, chester and springfield. See MLS Property & Listing Details & 22 images.

CHESTER VT Home for sale $$470,000 | $106 per sq.ft.

$470,000 | $106 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $20,000 down 4% on October 18th 2017

7 Beds | 8 Baths |   Total Sq. Ft. 4424  |  Acres: 0.6
Come explore this charming, historic victorian home located in the heart of the chester village on the village green of shops and restaurants, adjacent to a historical schoolhouse, a cemetary dating back to 1761 and city owned open space. built circa 1820, the inn was established in 1982 and is currently an operating bnb inn. it has been lovingly maintained over the years and it shows. appreciate the grand staircase, the exquisite bay windows, turret and wrap around porch. enjoy the formal entry, comfortable living room, and the oak pocket door entry to the library! relax with a book by the fireplace! the 2nd floor has 7 bedrooms all with private baths and plenty of closet space. the house and carriage barn buildings are on the national historic the back of the house, in the attached barn is the current toy and teddy bear shop. additional to the property is a two story carriage horse barn. in the rear of the property stands a delightful 3 bedroom, 2 bath cottage ready for service as an inn keeper cottage, mil, or income producing rental. this property includes an expansive yard for family activities, pets, and even chickens. this amazing home, rich in history, is ready and waiting for your commercial or residential inquiry. okemo, magic & grafton nordic ski center are all close by. See MLS Property & Listing Details & 12 images.

CHESTER VT Home for sale $$445,000 | $154 per sq.ft.

$445,000 | $154 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $104,000 down 23% on September 29th 2017

5 Beds | 3 Baths |   Total Sq. Ft. 2885  |  Acres: 10.19
This quintessential farmhouse has many unique features throughout, including a fireplace in the kitchen, living room, and master, the home is prominently sited on 10 acres of farmland with a separate barn for animals and another that houses an indoor swimming pool and hot tub! a large first floor master suite and expansive great room shares views both in the front and back of the farmhouse of the pasture land. enjoy the screened in patio and fenced in yard area out back! the home’s central eat-in kitchen joins casual living spaces with the more formal living & dining rooms, upper-level guest bedrooms. beautiful stone walls surround this classic new england style home that reaps the benefits of the surrounding farmland and picturesque setting, and offers fun for all with the pool and animal barns! See MLS Property & Listing Details & 27 images.

CHESTER VT Home for sale $$368,000 | $150 per sq.ft.

$368,000 | $150 per sq.ft. CHESTER VT HOME FOR SALE

4 Beds | 3 Baths |   Total Sq. Ft. 2747  |  Acres: 4.5
Step away from the hustle and bustle, leave the pavement, and wind through the tree canopy on a quiet road with gentle curves carved by the rocky stream alongside. pull into a true vermont homestead exposing a traditional saltbox, car barn and sugarhouse with sunshine, open lawn and room to park and play. the green mountain view from anywhere feels private whether you are working in the organic garden or oversize potting shed, sitting at the fire pit, or enjoying a beverage on the screened porch. spacious open-living emerges after the entry/mudroom. granite counters and warm wood cabinets anchor the kitchen side with dining centered and living area enjoying the radiating wood stove. adjacent is the office/study and beyond are the family room and porch. light and views from the southern exposure and 8/8 oversize windows is enjoyed all throughout most of the first floor and second. the second floor hosts three bedrooms with hall bath plus a master wing with private bath featuring a custom vermont slate shower, walk-in closet and skylights. wood flooring, handcrafted wood doors and access to the bonus area of a walk-up attic complete the upstairs. the lower level finished area is now used as a weight room and unfinished areas as workshop, utilities and lots of storage. the newer detached oversize garage with storage wings offers wood heat on the first floor while the spacious finished upstairs is utilized as an office and heated by propane heater- again with views- lovely site! See MLS Property & Listing Details & 40 images.

CHESTER VT Home for sale $$352,000 | $111 per sq.ft.

$352,000 | $111 per sq.ft. CHESTER VT HOME FOR SALE

4 Beds | 3 Baths |   Total Sq. Ft. 3185  |  Acres: 23
This federal style 1870 home is handsomely located in a quiet rural setting, but convenient to several communities. 12 minutes to the village green in chester, 12 minutes to downtown springfield, 21 minutes to ludlow & okemo. this picturesque setting was once operated for most of the 20th century as the mattson dairy, for which the road is named. several of the original barns still proudly stand and may provide any number of possibilities for productive use. the current owners have upgraded many of the home features including a new septic system and added a convenient second floor laundry. it has been thoughtfully modernized and you will find an extremely comfortable and spacious country home awaits you. with four bedrooms, converted attic space, 2 bathrooms, 2 living rooms, the cutest front porch with views to the nearby pond, a large rear porch with built in fireplace and a secret hidden pond you will find lots of quiet spaces to relax. See MLS Property & Listing Details & 16 images.

CHESTER VT Home for sale $$337,000 | $135 per sq.ft.

$337,000 | $135 per sq.ft. CHESTER VT HOME FOR SALE

3 Beds | 3 Baths |   Total Sq. Ft. 2700  |  Acres: 3.7
A beautiful setting for this newer custom built 3+ bedroom 3 full bath log home. situated on 3.7+/- acres conveniently located just off route 10 in chester. boasting a floor to cathedral ceiling stone fireplace, open living concept and first floor bedrooms. this custom log home has an upstairs private master suite with it's own loft area, perfect area for the reading nook. look out over the serene pond setting with firepit and zip line from the wrap around deck. the oversized attached two car garage has ample storage for vehicles, your toys or a combination. the large mudroom just off the garage will store all of your gear and then some. downstairs to another bedroom, open family room, full bath and laundry/utility room which houses a state of the art budarus furnace that supplies the radiant heat throughout this wonderful home. the covered front porch the perfect finishing touch to this custom home. bonus space above the garage can also be finished, already plumbed for heat. just minutes to okemo skiing and ludlow and all it has to offer as well as the charming village of chester. See MLS Property & Listing Details & 40 images.

CHESTER VT Home for sale $$335,000 | $88 per sq.ft.

$335,000 | $88 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $14,000 down 4% on September 16th 2016

5 Beds | 5 Baths |   Total Sq. Ft. 3800  |  Acres: 5.1
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. See MLS Property & Listing Details & 24 images.

CHESTER VT Home for sale $$335,000 | $86 per sq.ft.

$335,000 | $86 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $30,000 down 9% on December 1st 2017

4 Beds | 3 Baths |   Total Sq. Ft. 3915  |  Acres: 21
Imagine stepping out of your aromatherapy shower and basking in the light from the home's many south facing over-sized windows. walk outside and smell the mature rhododendron bushes or pick fruit from your pear, plum, and crab apple trees. stroll through the 21 acres of private woods listening to the birds and the small winding brook. with a massive mudroom, walk in pantry, newer standing seam metal roof, on demand hot water, wood stove and so much more, you don't want to miss this one! endless possibilities with this secluded custom built post and beam colonial! looking for a ski home? at only 20 minutes to okemo and 15 minutes from i91, the nearly 4,000 finished square feet could make this an ideal ski retreat for you and your friends. horse property? absolutely! the exterior shed was previously used as a 1 stall barn and comes with a fenced in pen. motivated seller, bring all offers! See MLS Property & Listing Details & 25 images.

CHESTER VT Home for sale $$299,000 | $125 per sq.ft.

$299,000 | $125 per sq.ft. CHESTER VT HOME FOR SALE

3 Beds | 3 Baths |   Total Sq. Ft. 2400  |  Acres: 5
Enjoy a comfortable, five acre country setting with the spacious, modern home at the end of an easy, level driveway. cathedral ceilings, about a 2400 square feet floor plan offering ample family space inside and out. enjoy 3 baths, 3 bedrooms, an office, great room, well placed kitchen with plenty of storage, main level foyer and comfortable family room. this bright, open contemporary home is looking for a new owner. underground electricity from the road offers unobstructed sight and use of the level grounds. the location is close to several ski areas, lakes, ponds, hiking and antiquing. only 4 miles to all the conveniences of chester's village. See MLS Property & Listing Details & 19 images.

CHESTER VT Home for sale $$299,000 | $111 per sq.ft.

$299,000 | $111 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $19,000 down 6% on October 4th 2017

4 Beds | 3 Baths |   Total Sq. Ft. 2688  |  Acres: 7.06
This 4 bed/3 bath home sits on over 7 acres of land near the end of a dead-end country road and is minutes to the village of chester. built in 2008 to custom specifications, this home has plenty of storage, a large laundry room with a ¾ bath and a master suite with custom tile shower, a japanese soaking tub and its own deck. the main level of the house has a large living room with brand- new flooring, woodstove and stone hearth and sits adjacent to the gourmet kitchen featuring a commercial hood over the “blue star” 6 burner gas range and pot-filler faucet. the dining room opens to the covered deck and 12 x 22 blue stone patio. rounding out the main floor and just off the living room is a large den/office which could be used as a 2nd living room, library or a bedroom. all of this is flanked by the farmer’s porch where you will want to spend all your time. this home was built in a controlled environment using 2 x 6 construction with plywood (not composite), copper piping, 10” basement concrete walls & radiant heat in the basement floor. the decking is all low-maintenance trex material and the siding is a high-quality vinyl. the grounds include several perennial gardens and a 6’ deep pond. the basement level is just waiting for your own touches. if you are a skier, snowborder, snowmobiler, or just an outdoor enthusiast, this is an ideal property and location; less than 30 minutes to 3 major ski resorts, close to vast snowmobile trail and a short drive to the chester green! See MLS Property & Listing Details & 40 images. Includes a Virtual Tour

CHESTER VT Home for sale $$299,000 | $109 per sq.ft.

$299,000 | $109 per sq.ft. CHESTER VT HOME FOR SALE
Price Change! reduced by $25,900 down 9% on November 18th 2017

3 Beds | 3 Baths |   Total Sq. Ft. 2750  |  Acres: 4.54
Post & beam construction with soft wood flooring, a fireplace with a wood stove, expanded butcher block island in the kitchen with seating and cook top stove, first floor bedroom and a lovely office, studio or library will get us started. three additional bedroom, two baths and a laundry room completes the second floor! this country treasure is located perfectly. almost equidistant to chester and, springfield. also not far to ludlow. a kohler stand by generator was installed in 2006, as well as anderson windows. the propane boiler with 3 zones was new in 2008 and the seller owns the 2 large propane tanks. (negotiate your own deal with propane providers.) the heated over sized two car garage is home to an "endless pool" ready to keep you fit and huge second floor storage space will be noted above the garage. enjoy the wooded acreage with rock outcroppings and old trails for meandering. See MLS Property & Listing Details & 30 images.

CHESTER VT Home for sale $$299,000 | $207 per sq.ft.

$299,000 | $207 per sq.ft. CHESTER VT HOME FOR SALE

2 Beds | 2 Baths |   Total Sq. Ft. 1444  |  Acres: 6.5
Comfortable country log home with westerly mountain view over the half acre cold water pond stocked with trophy rainbow trout. enjoy the pleasant view from the large back porch. this clean two bedroom, two bath log home, with a log sided two car garage situated on 6.5 surveyed acres on a town maintained road a few miles from chester village, awaits your inspection. a few other amenities add to the comfort and utility of this fine home, such as a vermont casting wood stove, with generator, full dry basement with walkout access. it comes with appliances, dining room furniture, porch furniture, propane barbecue and a boat. the pond is quite an attraction as it is reported to be 19 feet deep, for swimming, ice skating, fishing or just paddling around on a lazy afternoon. this home and property is picture perfect, all systems are in fine shape, ready for new owners. See MLS Property & Listing Details & 29 images.

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