Land for sale, Residential Property for sale in Chester Vermont | Page 1 of 2 | Lands of Vermont
#1 in Rural Real Estate Online

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

34 photos
$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
40 photos
$183,529 1.25 acres 3 Beds | 2 Baths | 1 ½ Bath | 1462 sqft
1242 VT Route 11E, Chester, VT 05143 - Windsor County

1.25 acres Chester, VT

Home Sweet Home. Meticulously maintained Cape. Lovely kitchen with granite countertops. Plenty of cabinets. Dining area with builtin. Full bath with ceramic tile floor. Spacious living room with beautiful Brazilian cherry wood floor, propane fireplace with marble surround, and beamed ceiling. Newer windows throughout. Second floor has 3 bedrooms and half bath. Three car heated garage space. One of garage spaces has a great workshop space. Wonderful back and side yard for gardening or play. Sit and relax by the brook located on the back side of the yard. Storage shed. House is wired for Generac propane generator.
25 photos
$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!
30 photos
$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
11 photos
$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.
37 photos
$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
40 photos
$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
38 photos
$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
19 photos
$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
23 photos
$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
29 photos
$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
32 photos
$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
14 photos
$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
39 photos
$369,500 3.7 acres 3 Beds | 3 Baths | 3174 sqft
93 Rachel's Way, Chester, VT 05143 - Windsor County

3.7 acres Chester, VT

LOG CABIN.....Bright & Cheery and ready to move right in. This home is only 10 years old and has been lightly lived in and its immaculate condition reflects just that. The wall of windows that overlook the pond as well as the soaring stone fireplace immediately draw your attention as you walk through the front door. There is radiant wood flooring throughout and beautiful custom wood walls and ceilings. The living & dining areas have vaulted ceilings and you can enjoy the very pretty and peaceful views of the pond and backyard area from both. The main floor also offers an oversize bedroom with office space and the open kitchen/dining area includes a breakfast bar and upgraded lighting. The upper level consists of a very large en-suite and a
25 photos
$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
37 photos
$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
22 photos
$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).
32 photos
$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
33 photos
$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.
36 photos
$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
32 photos
$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
23 photos
$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.
21 photos
$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 owe it to yourself to come ta
14 photos
$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
22 photos
$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
16 photos
$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!
26 photos
$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!
225 photos
$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
10 photos
$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.
35 photos
$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