Land for sale, Residential Property for sale in Chester Vermont | Page 1 of 2 | Lands of Vermont
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Land for sale including Residential Property in Chester Vermont - Page 1 of 2

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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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$299,000 23 acres 4 Beds | 3 Baths | 1 ½ Bath | 3185 sqft
2141 Mattson Road, Chester, VT 04143 - Windsor County

23 acres Chester, VT

Calling all gentleman farmers! Here are 23 beautiful acres for your imagination and BARNS located in a quiet rural setting! The Federal style 1870 home is handsome and ready for a new family to love it! Notice it's convenience to several communities. (12 minutes to Chester, 12 minutes to Springfield, 21 minutes to Ludlow) The picturesque setting was well known as Mattson Dairy and operated for most of the 20th century, hense, the road is named for the family. Several of the original barns still proudly stand and may provide any number of possibilities for productive use. The current owners have upgraded the home including a new septic system and a convenient second floor laundry, as well as a unique space which might be a studio or office
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$599,000 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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$149,000 0.5 acres 4 Beds | 2 Baths | 1930 sqft
431 Elm Street, Chester, VT 05143 - Windsor County

0.5 acres Chester, VT

Just reduced! 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
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$125,000 1.77 acres 4 Beds | 3 Baths | 2958 sqft
289 Grafton Street, Chester, VT 05143 - Windsor County

1.77 acres Chester, VT

Handyman special! This property was once a historic gem and had many upgrades when it was operated as a bed and breakfast. Through the years it has had some deferred maintenance and could use a good polish to bring it back to life. The main entry welcomes you into a massive country kitchen with custom cabinetry, warm softwood floors and an expansive deck that overlooks the rear yard. The front sitting room and formal dining room offer an open concept and enjoy a large wood stove that is a focal point. The other two rooms could be converted into private quarters for guest or used as a first-floor master bedroom. Travel up the original grand staircase and find four more rooms with 2 full baths. The home is heated with a forced air furnace but
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$285,000 6 acres 3 Beds | 2 Baths | 2063 sqft
3698 Flamstead Road, Chester, VT 05143 - Windsor County

6 acres Chester, VT

Just off the beaten path, conveniently located near Chester and Okemo Mountain, sits this charming updated Vermont farmhouse. Enter through the covered porch into the convenient mudroom, shed your outside gear and get ready to relax knowing there's a place for everything and everything is in its place. Updated with beautiful wide hardwood floors in the open plan living, dining, and kitchen areas, you and your guests will appreciate the modern farmhouse feel as you warm by the wood stove, create a meal with the gas range and gather in the ample dining area. A bonus room off the living area could be an office, den, yoga space,or extra bedroom-you decide! A staircase over the main living area leads to a private master bedroom oasis, complet
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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

Dream home and proven income producing property surrounded by major ski areas including Jackson Gore/Okemo, Magic Mountain, Grafton, Bromley, Straton and others. 30 mins away from the shops in Manchester. Situated on /- 55 acres -- wooded and open pasture. Bring your horses! This is a wonderful place to raise a family on a quiet, lightly travelled back country road. Great retreat for artists, writers, executives, and anyone looking to disconnect and recharge. (High speed internet if you can't handle solitude.)This is a perfect home, whether full time or vacation, for anyone who values gazing at the starlit evening sky, listening to the streams located on the property, walking through the woods, or cross country skiing / snow-shoeing the
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$94,000 1 acres 3 Beds | 2 Baths | 1790 sqft
335 Grafton Road, Chester, VT 05143 - Windsor County

1 acres Chester, VT

Ranch style home with plenty of room for everyone. Home boasts 3 bedrooms, 2 full baths, a loft with balcony and is handicap accessible!
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$319,000 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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$215,000 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

This home has been loved by the current owners since 1977. Their children grew up here, but it is now time to move closer to those grown kids. A delightful offering in Chester's Stone Village. This 1810 classic Federal has unusual brick ends & clapboard front design. You will benefit from the new sheathing and shingle roof over the mid-section. In the spring, the front metal roof will be professionally treated and paintedit will be ready to go for many more years. 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 in
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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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$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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$795,000 245 acres 4 Beds | 4 Baths | 3808 sqft
231 Christmas Tree Farm Rd, Chester, VT 05143 - Windsor County

245 acres Chester, VT

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 wi
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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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$699,000 26.4 acres 4 Beds | 3 Baths | 3445 sqft
1502 Popple Dungeon Road, Chester, VT 05143 - Windsor County

26.4 acres Chester, VT

Be ready to fall in love! Just 3.5 miles from the green in Chester, you will find this stunning Farmhouse built in 1989. A superb country location. The land is split into both sides of the road providing permanent protection. Across the street from the house is a large, flat field that is perfect for horses. Over 1,300 feet of frontage along the South Branch of the Williams River. On the house side of the street, you will find multiple outbuildings & barns. Sheep & horses are currently at home here. Gardens, sheds, & a car barn with a huge studio above awaits craftspeople, writers, woodworkers, or exercise enthusiasts. Saving the best for last, the home is just stunning. Covered porches for quiet time. Enter through the front door to large
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$35,000 5 acres
1031 Cummings Road, Chester, VT 05143 - Windsor County

5 acres Chester, VT

Prime 5 /- acre Chester wooded corner lot with frontage on Cummings Rd. and Rte 11 East has residential and/or home business potential. Remainder land from old farm across the road, the parcel has Stone walls, dirt road and paved road frontage. A Stream traverses the property. Located in close proximity to Chester and convenient to Springfield. Make your access off the country road or utilize the major road frontage and exposure this property affords. The old camp on Cummings Road side marks the spot as possible building site.
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$448,000 10.25 acres 9 Beds | 7 Baths | 1 ½ Bath | 5482 sqft
665 10 Route, Chester, VT 05143 - Windsor County

10.25 acres Chester, VT

A curving grand staircase nostalgically welcomes all who enter this sprawling quirky 1800s farmhouse with original wide board floors. The uses for this property are endless whether it be for private or commercial purposes. The calm and serene landscape make it perfect for a retreat. While its quick access to local attractions make it ideal for vacationers and full time residents alike. This home was once a charming B&B offering 9 bedrooms (most ensuite) which ensures there is room for everyone. A commercial kitchen, dining room that seats 24 and separate owners quarters, media room, cozy library and charming sitting room offer many possibilities. The large 2000sqft barn with room for a massive workshop or studio space alongside the run-i
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$239,000 0.5 acres 3 Beds | 2 Baths | 1960 sqft
67 Main Street, Chester, VT 05143 - Windsor County

0.5 acres Chester, VT

Enjoy life in this wonderful antique farmhouse within walking distance of the many conveniences in Chester's village. This home has been thoughtfully updated with an eye toward simplicity. Room sizes are just right, two full baths are in place, an office or den is located just off the bright kitchen. The formal dining room leads to the front parlor and the stairway to the second floor where you will find three bedrooms and a spacious bath. The master bedroom enjoys a sitting area perfect for conversation or a quiet reading nook. Don't miss the porches on the front and side of the home, as well as the spacious yard with it's deck ready for your family and friends. A paved driveway leads to the over sized garage with plenty of room for storag
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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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$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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$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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$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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$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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$164,900 5 acres 2 Beds | 1 Bath | 1056 sqft
299 Ethan Allen Road, Chester, VT 05143 - Windsor County

5 acres Chester, VT

Attention Snow sledders!! This cozy cottage feels like you are a million miles from the busy world outside but is just minutes from the VAST trails and 12 minutes from both Chester and Grafton Vermont. This lovingly maintained home will make the perfect getaway as either a full-time residence or vacation retreat. Quietly hidden away among 5 wooded acres you wont want leave whether it is to enjoy the surrounding nature or just lounge in the hot tub. The spacious workshop with large garage door is ready to for any hobbyist or serious craftsman to set up shop. Come take a look today!
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$225,000 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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$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
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$119,900 5.64 acres
0 Brookside Lot 10-D Drive, Chester, VT 05143 - Windsor County

5.64 acres Chester, VT

Awesome 5.64 /- acre Chester parcel in 8 lot subdivision with clearing and dramatic views to valley and ridges to southwest. State approved septic for 4 bedroom residence- inground leachfield is already installed. This parcel drops slightly below the private road and opens up to a dramatic long range southwesterly view offering a private setting as the open section is surrounded by mature forest and protected from the road.
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$159,000 6.7 acres 3 Beds | 2 Baths | 1860 sqft
1436 VT Route 103 North Route, Chester, VT 05143 - Windsor County

6.7 acres Chester, VT

Big price reduction, owner is extremely motivated. Tastefully up-dated farm house with lots of charm & space to spread out. Some of the features here are brick fire place in the living room & wood stove & hearth in the family room, office space, heated mud/laundry/exercise room, work shop, barn/garage with overhead storage, detached one car garage. Also of note are built in corner cupboards in the dining room, a first floor bedroom & a first floor full bath, two bedrooms upstairs, the master bedroom with a wee little wood stove, an attic & lots of closets, three porches all situated on 6.7 country acres. The water has been tested and the septic tank has been pumped & inspected. The owner to pay for sun-porch removal & small foundation repa
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$124,900 5 acres
47 Balch Road, Chester, VT 05143 - Windsor County

5 acres Chester, VT

Just imagine! This land opportunity has numerous permitted and conditional uses. The existing drilled well is amazing! The old barn may still be serviceable for your needs. Great signage exposure for your venture on Route 11. A beautiful lot for your home, as well. Perhaps a home occupation? Many varied possible endeavors possible in this zoning district. The lot is almost level with road frontage on Balch Road and VT Route 11 great solar exposure and local mountain view. Just a short drive to downtown Chester Village for shopping and banking, with great access to all the recreational facilities in southern Vermont. There is high speed internet availability at this site. Former site for many years of the Mackenzie Construction. Come take
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$225,000 1.82 acres 3 Beds | 3 Baths | 1 ½ Bath | 1865 sqft
638 Remington Road, Chester, VT 05143 - Windsor County

1.82 acres Chester, VT

Comfortable Chester country ranch that is secluded but not isolated. Well built, energy efficient, 3 bed rooms 2 &1/2 baths, handicapped accessible set on 1.82 acres within minutes drive of VT Route 103 & Chester Village. Some of the other features: 2 car attached garage with remote & another garage in the basement, full dry basement, porch, deck & a pleasant vista to the mountains to the east. Other features: some radiant heated floors, solar heater & a few kitchen goodies: fold away butcher block & hide a way mixer for the cook. Planned residential community with covenants to help protect your investment. Listed well below town assessment, don't let this one get away! Buy now pay later the American way!