Land for sale in Chester Vermont | Page 1 of 2 | Lands of America
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Land for sale in Chester Vermont - Page 1 of 2

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$69,000 0 acres
1599 Mattson, Chester, VT 05143 - Windsor County

0 acres Chester, VT

Property offers 10 + acres with an old mobile home that will need to be removed.
April Shepard CENTURY 21 Shepard & Flint Realty
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$160,000 2.5 acres 2 Beds | 1 Bath | 640 sqft
18 Linquist Road, Chester, VT 05143 - Windsor County

2.5 acres Chester, VT

PRICE REDUCTION: If you are looking for a Handy man's Special, that is ideally located in close proximity to fishing, golfing, kayaking, skiing & snowmobiling, then this may be the home & property for you. The sale includes the handy mans special home, plus a two bedroom mobile home with drilled well & septic system. Additionally, there are two dug wells & two additional septic systems, all on 2.5 acres. One could live in the mobile home, while rehabbing the existing framed home. If this sounds right for you, then schedule a time today to explore the possibilities.
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$160,000 1 acres 3 Beds | 1 Bath | 1340 sqft
62 Davidson Hill Road, Chester, VT 05143 - Windsor County

1 acres Chester, VT

Charming, bucolic setting with easy access to Ludlow, Chester and Woodstock. Perennials, blueberry bushes, large deck, smaller deck as well as a private balcony off the second floor master bedroom. A short drive off the main road for easy access...Sits up high and is set back from the road for privacy and prestige. 15 Minutes to Downtown Ludlow, 10 to Chester. Large Fenced in area to one side of the home for your pets to play. The current owners have put a lot of TLC over the years into making this a very welcoming, very comfortable second home to spend time with friends and family. If you're looking for your own special place (whether it be seasonal, occasional or year-round) here in ski country...you owe it to yourself to come ta
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$129,500 1.65 acres 2 Beds | 1 Bath | 920 sqft
1036 Farrar Road, Chester, VT 05143 - Windsor County

1.65 acres Chester, VT

PRICE REDUCTION! Ready for your piece of Vermont? Not quite a tiny house, but on this back road in the wonderful town of Chester is this cute bungalow waiting for new owners. The main level is open with a good-sized deck. The upper level has two bedrooms. One is currently set up as a walk through to the other one. The Vermont charm in this home includes natural wood on some ceilings, walls, and floors. Sellers have been sprucing it up and will be installing a new range and efficient hot water heater to go with the efficient boiler. The well was drilled in 2006. Feel free to drive by and see if you like the location and setting. (Property is in both Chester and Andover, but address is Chester).
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$165,000 1 acres 3 Beds | 2 Baths | 1 ½ Bath | 1452 sqft
5032 Vt Rte 103 Highway, Chester, VT 05143 - Windsor County

1 acres Chester, VT

This 3 bedroom energy efficient ranch has been fully and professionally insulated, in addition to the weatherization that includes exterior vinyl siding and newer replacement windows, and a standing seam roof. An adjacent two story 4 bay garage.....perfect storage for all of your toys, to include automobiles, snowmobiles, motorcycles. There is concrete flooring, a separate office area, and the the garage is also set up for heat (the oil tank and oil lines are in place for a furnace) and there is separate circuit breaker power. The second floor, with full stairway access, is open for a variety uses. Three of the doors are 8'x 8' and one is 8' x 10'. The home interior has a large, centrally located, eat-in kitchen adjacent to both the li
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$329,999 1.79 acres 4 Beds | 3 Baths | 1 ½ Bath | 2124 sqft
662 Remington Road, Chester, VT 05143 - Windsor County

1.79 acres Chester, VT

Private setting but only 7 miles to I91. Beautiful downtown Chester is only 5 minutes away and 20 minutes to 3 major ski areas. VAST trails, town pool and tennis courts are near by. This lovely 4 bedroom 3 bath home was built in 2007 but the interior was completed in 2013. Radiant hardwood floors with radiant inland ceramic tile in the bathrooms. Master bedroom has a walk-in closet and a bath. Large 12x48 deck that has glass doors from the master bedroom and dining room. Kitchen boasts granite counters with stainless steel appliances. The living room has cathedral ceilings and a area framed out for a gas fireplace. The family room has glass doors that lead out to a a patio area. The home has fiber optic internet, WiFi programable rem
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$169,000 0.5 acres 4 Beds | 2 Baths | 1930 sqft
431 Elm Street, Chester, VT 05143 - Windsor County

0.5 acres Chester, VT

Charming 4 bedroom/2 bath Victorian-era farmhouse with modern amenities and old-world charm. Renovated in 2017. New pellet stove, updated wiring, new plumbing. Large eat-in-kitchen with all new appliances. First floor bedroom, laundry and full bath, beautifully refinished softwood floors in living/dining, and restored ceilings to original height. Energy efficient furnace with two zones and Ecobee thermostat, town water & sewer. A large wrap-around porch and period details such as original doors and a stained glass window enhance the charm. Large detached two story barn with 2 car garage and additional work rooms on first floor, and an enormous second floor perfect for studio, gym or business. Paved driveway and lush yards with ma
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$244,000 1 acres 7 Beds | 7 Baths | 1 ½ Bath | 3136 sqft
87 North Street, Chester, VT 05143 - Windsor County

1 acres Chester, VT

A piece of history situated so perfectly in the historic Stone Village awaits you. Come explore all this incredible property has to offer. This property could suit so many buyers as it has been used in many ways in the past. Once opperated as the perfect B&B and also as a community cares home as well as currently home to a massage business with private office and treatment room, the possibilities are endless. Ready for full-time use with plenty of room for family and guests. Enjoy being central to skiing, boating, hiking and within minutes of Interstate 91 for easy access to your property. The main house offers 6 bedrooms and each bedroom is equipped with its own bath. The country kitchen offers ample space chafing up family dinners which
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$335,000 21 acres 4 Beds | 3 Baths | 1 ½ Bath | 3915 sqft
4419 Trebo Rd Road, Chester, VT 05143 - Windsor County

21 acres Chester, VT

Priced almost $100,000 below assessed value! 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 i
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$329,000 19 acres 3 Beds | 3 Baths | 1 ½ Bath | 2112 sqft
690 Trebo Road, Chester, VT 05143 - Windsor County

19 acres Chester, VT

Bring the horses to multiple fenced pastures, shed and barn with water and electric which currently has one stall but could accommodate two more...all on almost 20 acres. Bright charming colonial with large country kitchen, Family room with vaulted ceilings, skylight, and soapstone wood-stove and large combination living room/dining room. Also on the first floor is a study, foyer and 1/2 bath. There is radiant heating on the main floor. Upstairs is a spacious master bedroom suite with a bath and walk-in closet. Full basement has high ceilings and could easily be finished for additional space as well as an attached two car garage. Buderus boiler with 3 zones, whole house generator, and solar panels make this home energy efficient.
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$329,000 5 acres 3 Beds | 3 Baths | 1 ½ Bath | 2250 sqft
50 Howard Road, Chester, VT 05143 - Windsor County

5 acres Chester, VT

Elegantly tucked away in the woods near the end of a private dirt road sits this carefully crafted and inviting timber frame home. The warm wood tones invites you in and conjures images of cozy family gatherings by the fire while the wind and snow whistles outside. In summer the home is cooled by the shade of the surrounding mature trees allowing for you to live out on the large deck and enjoy the established and colorful flower beds which are dotted throughout the enchanting landscape. The classic New England Saltbox style allows for a large master bedroom with high ceilings and spacious room throughout. And with three full floors of living space, with a bathroom on each floor, this will make an ideal family home or vacation hideaway. Whil
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$249,000 0.75 acres 4 Beds | 2 Baths | 1 ½ Bath | 1880 sqft
124 Grafton Street, Chester, VT 05143 - Windsor County

0.75 acres Chester, VT

Artfully updated 4 bedroom, 1.5 bath village farmhouse that shines inside and out! Beautifully designed entry off the paved driveway opens to the convenient mudroom area adjoining the spacious, attractively outfitted gourmet kitchen featuring a generous center island, ample cabinets and counter work space, stainless steel farm-style sink and appliances, recessed lighting, pantry cupboard with pullouts, a first floor laundry room with barn style door and a half bath. A light filled dining room with bay window and built-ins just off the kitchen area is accented by charming french doors. The large, comfortable living room features a wood burning fireplace, built-in bookcases and wood flooring. The second floor features a large landing with 4 b
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$200,000 0.5 acres 3 Beds | 3 Baths | 2 ½ Baths | 2964 sqft
270 North Street, Chester, VT 05143 - Windsor County

0.5 acres Chester, VT

Owners heading closer to family!! A delightful offering in Chester's Stone Village. This 1810 classic Federal has unusual brick ends & clapboard front design. Four fireplaces! Imagine, convenient village living with views to the front and rear. A fine example of New England's connected architecture. From front to back, there is finished usable space. If you have the need for a home occupation or a studio, look no further. The attached heated and insulated barn will serve you well. Many updates include new windows, updated mechanicals including all new wiring, insulation, new kitchen/breakfast room. You will fall in love with the many rooms...front parlor, living room, den on the first floor. Master, two bedrooms, & a hobby room on the secon
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$325,000 20.4 acres 3 Beds | 3 Baths | 1 ½ Bath | 2752 sqft
1637 Trebo Road, Chester, VT 05143 - Windsor County

20.4 acres Chester, VT

This "end of then road" location offers a spectacular contemporary log home on 20.4 acres with plenty of privacy. The warm wood interior with cathedral ceilings provides a comfortable open design which is family, as well as entertainment, friendly. A gas fireplace is the focal point in the Great Room and warms it nicely! The potential views through the massive windows that look out over the land will be readily noticeable. The fully applianced kitchen is stylish and functional with stone counter tops and plenty of cabinetry. Enjoy dining on the expansive screened porch during the warmer months or the adjacent breakfast nook or the formal space inside . The main level also offers a large master suite, cathedral ceilings, and a 1/2 bath. Head
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$625,000 28.6 acres 4 Beds | 3 Baths | 1 ½ Bath | 2721 sqft
2595 Flamstead Road, Chester, VT 05143 - Windsor County

28.6 acres Chester, VT

Highland Ponds Country Estate Living. While maintaining historical charm and traditional New England architecture, this four bedroom, 1820 brick cape has received updates designed for modern living and entertaining. Dutch-tiled fireplace and built-in shelves in the library, classic windows, wood floors and formal dining room showcase original character. Entertaining options abound in the living room with wood stove, sun room and adjacent patio with hot tub. Lovely views of Okemo from the 28 peaceful acres of stone wall-lined pastures, ponds, woodlands and berry gardens. Several outbuildings complete the estate. The artists studio has an attached 2 car garage, while the cozy guest cottage offers open living, kitchenette, dining room, u
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$995,000 2.28 acres
40 Common Street, Chester, VT 05143 - Windsor County

2.28 acres Chester, VT

For over a century the Fullerton Inn has remained a keystone to historic Chester, Vermont. Though the hands of time have changed the facility and its ownership, The Fullerton has remained an institution. Having continued to deliver excellent quality of service throughout the years, since before the Civil War. The Inn has very spacious public rooms which include a huge reception room with stone fireplace and comfortable seating areas, tavern, several dining rooms, breakfast room, conference room, very large front porches and Rear deck. The front porches take in the activity of the Village plus offer alfresco dining in warmer weather. The huge rear deck allows for privacy and large parties. All 20 guest rooms have private baths and are indi
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$379,000 10.1 acres 3 Beds | 2 Baths | 2529 sqft
604 Church, Chester, VT 05143 - Windsor County

10.1 acres Chester, VT

In town but private totally renovated farmhouse on 10 open acres with long frontage on the Williams River and pleasant views. With 3 ponds, fruit trees, fertile planting areas and water & electric field stations in 2 locations, there are many ways to enjoy this lovely property. The 2529 sq. ft main house has been renovated to include a state of the art kitchen, new bathes, (one with a steam shower) mud room, timber framed addition, and a large deck overlooking the 10 acres. New boiler, updated plumbing and wiring, and a new septic system will make this a trouble free investment for years to come. Easy one floor living. This home has an airy open floor plan with brick fireplace perfect for relaxing with family or friends. There is an effic
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$439,000 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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$65,000 1.5 acres
40 Fenton Road, Chester, VT 05143 - Windsor County

1.5 acres Chester, VT

Are you looking for a piece of Vermont for your primary or secondary residency that contains a drilled well, septic, paved driveway & that can be easily accessed in all seasons? If so, then this may be the ideal parcel for you. It is located only 35 minutes from I-91 & is in close proximity to biking, hiking, golfing, kayaking, skiing & snowmobiling or visit & enjoy quaint New England Villages, with their historic country stores & summer theaters. If this sounds right for you, then schedule a time today to see if this parcel fits your needs.
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$273,900 0.67 acres 6 Beds | 6 Baths | 1 ½ Bath | 3573 sqft
166 North Street, Chester, VT 05143 - Windsor County

0.67 acres Chester, VT

Classic c. 1840 large stone home on North Main Street ( locally called Stone Village ) in Chester, VT. This lovely home has lots of appealing features: on the outside a stone Cooper's shed, paved driveway, lovely landscaped yard, small pond, slate & standing seam metal roof, 2 awnings on the sun porch, a few apple trees, stone work & a small covered bridge. On the inside more than 3500 square feet of comfortable living space on 3 floors, over sized 2 car garage, 4 bed rooms, 4 1/2 baths plus, central air, 3 room extended family living space on the second level. Priced below recent appraised value & town assessment. Come see and invest in this lovely well maintained home.
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$239,900 6.5 acres 5 Beds | 3 Baths | 2922 sqft
642 High Street, Chester, VT 05143 - Windsor County

6.5 acres Chester, VT

Price reduced! 6.5 acres /-, great location! 1810 cape with spacious addition is ready for new ownership. Features include softwood flooring, formal living and dining rooms, 2 fireplaces, 1 with soapstone wood stove and original beehive oven, 4 bedrooms with large common area, 2 baths and family room. The 2002 addition features a generously appointed kitchen with soaring cathedral ceilings, interesting woodwork, clerestory windows, great cabinet space, reading nook and a master bedroom with study & bath that could easily convert to a private master suite. Walkout basement with mudroom & 2 car heated garage, workshop/utility room. The old barn/garage with fenced paddock area has been a home for a horse and goats. Potential for more mountain
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$275,000 0.56 acres 4 Beds | 6 Baths | 1 ½ Bath | 5814 sqft
35 Depot Street, Chester, VT 05143 - Windsor County

0.56 acres Chester, VT

An incredible investment awaits you nestled right inside of the Chester Village. The property is perfect for a live-in business with exceptional parking, walking distance to the Village Green which offers, shopping, dining and so much more. The interior offers a handsome staircase to the apartment unit and all throughout the home you can admire the beautiful crown moldings and all the charm this property enjoys. Having such a short drive to three different ski resorts you can enjoy through the winter months or a great rental option. This property has so many different options and you won't want to miss your chance to view today!
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$150,000 2.4 acres 2 Beds | 2 Baths | 1 ½ Bath | 1302 sqft
1447 Flamstead Road, Chester, VT 05143 - Windsor County

2.4 acres Chester, VT

They say that location is the most important thing in real estate. If that is the case then this property has it all and then some. This peaceful home is situated just 3 minutes to the Village of Chester and 10 minutes to Springfield and is set among some of the most beautiful pastoral landscapes Vermont has to offer. Just 15 miles from Okemo Mountain, this bright and quiet 2 bedroom 2 bath one level Ranch will make the perfect first home, retirement retreat or vacation home. The large 2 car detached garage has plenty of space for a workshop and room to store all your toys. The 2.4 /-acre flat parcel, with small pond, would make for a great hobby farm. With access to high speed fiber optic internet this would also make the most perfect w
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$348,500 12.42 acres 3 Beds | 2 Baths | 2344 sqft
814 Dodge Road, Chester, VT 05143 - Windsor County

12.42 acres Chester, VT

A short distance from town on a country road, a private, contemporary saltbox on 12.42 /- acres awaits! A farmer's porch connects with a deck wrapping around the large, inviting open concept living/dining space with cathedral ceiling, wood stove accented with beams and flooring milled from the property. The upgraded kitchen with quartz counters and stainless appliances is great for entertaining! There is a large first floor bedroom with adjoining full bath. The second floor loft-styled master suite will delight with private bath and covered porch. The large finished basement is a great gathering space and includes a third bedroom and tiled entry closet area. The grounds feature a large spring-fed pond, a nice combination of open and wooded
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$199,000 5.5 acres 3 Beds | 2 Baths | 1900 sqft
527 Church, Chester, VT 05143 - Windsor County

5.5 acres Chester, VT

Location, location! This home is situated just 1/2 mile from Chester Town Green and boosts 5.5 acres! Bright and sunny home has 3 bedrooms and 2 baths - there is a bedroom with private bath on the first floor. Large fireplace in the living room with open floor plan to the dining area. This property also has a 2 car detached garage and a shed with power. 10 - 15 minutes to Okemo and near the VAST trails - make it your own with just a few updates!
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$459,999 193 acres 6 Beds | 4 Baths | 2 ½ Baths | 4316 sqft
1328 Chandler Road, Chester, VT 05143 - Windsor County

193 acres Chester, VT

This Contemporary Sanctuary situated on 193 acres of open meadow, hard and soft woods, a year round brook, blueberry 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 the living, kitchen and entryway. Soap stone counters and farmers sink high light the kitchen with commercial grade stainless steel appliances. This home is in
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$212,500 55.5 acres 2 Beds | 2 Baths | 1 ½ Bath | 1464 sqft
138 Farrar Road, Chester, VT 05143 - Windsor County

55.5 acres Chester, VT

Contemporary chalet on 55 acres close to outdoor recreational activities such as skiing, hiking, fishing and snowmobiling. The land is in Current use and suitable for horses, farm animals and organic gardening as well as a large amount of wooded acres for wildlife and hunting. The home has an open floor plan with a stone fireplace and marble floors on main level. Peaceful and quiet location.
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$239,500 12 acres 4 Beds | 2 Baths | 1696 sqft
440 Davidson Hill Road, Chester, VT 05143 - Windsor County

12 acres Chester, VT

PANORAMIC VIEWS - 12 Acres - Close to Okemo Mountain and Southern Vermont Ski Areas and Resorts. This is a four-bed and two-bath home on 12 rural acres of land on a hill overlooking panoramic views of the Green Mountains and New Hampshire. Built in 1988 to custom specifications, this modular home is low maintenance with plenty of storage. The main level of the house has a large living room, and sits adjacent to the kitchen/dining area overlooking a wraparound deck to enjoy the beautiful view and evening sunsets. Take the stairs to two additional bedrooms and a large newly renovated bath. The basement is unfinished and waiting for your own touches. Enter the house through an attached lower-level garage or deck entrance. Designed and located
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$149,000 0.57 acres 3 Beds | 2 Baths | 1800 sqft
198 Peck Road, Chester, VT 05143 - Windsor County

0.57 acres Chester, VT

So many options for this charming home located just outside of the Chester Village. The home offers a spacious 2 bedroom unit with a handsome fireplace, hardwood floors, and a cozy covered porch. The in-law unit in the rear is perfect for overflow of guests or mother-law suit with a great loft space and spacious living area on the first level. The current owner has updated the heating with heat pumps and offers efficient heating and cooling. The level lawn is perfect space for gardens or plenty of room for children to play. Just minutes from I91, Chester, Rockingham, and Springfield. Come take in all this property has to offer.
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$87,500 8 acres 1 Bed | 1 Bath | 512 sqft
3648 Smokeshire Road, Chester, VT 05143 - Windsor County

8 acres Chester, VT

Just imagine...a four season cabin to get away to. In the summer, you will enjoy the river for soaking, fishing, and panning for gold. Yes, really! You will also kick back on your screened porch for some quiet R&R. In winter, you will fire up the gas heater and the woodstove, and you will enjoy your post skiing relaxation. Perhaps you would rather snowmobile. Route 12 is just a 1/2 mile away, and an easy connection right up the road. There is a brand new bathroom that is just waiting for the mini wall hung hot water heater, then you will have a hot shower after a day of play. One large bedroom, living room with stone fireplace. The kitchen is all set up and ready for you to cook away with your gas stove and gas refrigerator. All new