Vermont & New Hampshire Guide
Homes For Sale in Chester Vermont- 79 Properties Found! Start Over!
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    Vermont is a state in the New England region of the northeastern United States of America. The state ranks 45th by total area and 43rd by land area at 9,250 square miles (24,000 km²). It has a population of 608,827, ranking 49th of all fifty states (surpassing only Wyoming). The only New England state with no coastline along the Atlantic Ocean, Vermont is notable for the Green Mountains running north to south and Lake Champlain which makes up 50% of Vermont's western border. It is bordered by Massachusetts to the south, New Hampshire to the east, New York to the west, and the Canadian province of Quebec to the north.

    Originally inhabited by Native American tribes (Abenaki, and Iroquois), the territory that is now Vermont was claimed by France but became a British possession after France's defeat in the French and Indian War. For many years, the surrounding colonies disputed control of the area, especially New Hampshire and New York. Settlers who held land titles granted by these colonies were opposed by the Green Mountain Boys militia, which eventually prevailed in creating an independent state, the Vermont Republic, which was founded during the Revolutionary War and lasted for 14 years. In 1791, Vermont joined the United States as the fourteenth state.

    The state is noted for its scenery and dairy products. It is the leading producer of maple syrup in the United States. The state capital is Montpelier, and the largest city and metropolitan area is Burlington. No other state has a "largest" city as small as Burlington.

    More Vermont Real Estate, Pick a County:
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    Page 1 of 4 | - Next Page of Properties - Last Page
    Vermont Real Estate
    $14,500,000.00
    4931 Sq Ft
    Chester VT  HOME
    6 Beds
    2356 Lovers Lane  Chester
    5 Baths
    SMOKESHIRE VALLEY PRESERVE: 1,919 AC premier recreation & sporting retreat! Exceptional views & privacy, handsome c. 1819 Cape, guest house, antique barns, log cabin, hay fields, apple & berry orchard ... MLS # 2728011 [Read More!]
    Vermont Real Estate
    $14,500,000.00
     Sq Ft
    Chester VT  LAND
    Beds
     Lovers Lane  Chester
     Baths
    SMOKESHIRE VALLEY PRESERVE: 1,919 AC premier recreation & sporting retreat! Exceptional views & privacy, handsome c. 1819 Cape, guest house, antique barns, log cabin, hay fields, apple & berry orchard ... MLS # 2819890 [Read More!]
    Vermont Real Estate
    $1,250,000.00
     Sq Ft
    Chester VT  COM
    Beds
    523 + 557 Rte 103 North  Chester
     Baths
    If Chester is the heart of Southern VT antiques, then the Stone House Antique Center is the crown jewel. This highly successful operation has been in business since 1989. The property consists of 2.6 ... MLS # 2749060 [Read More!]
    Vermont Real Estate
    $699,000.00
    3000 Sq Ft
    Chester VT  HOME
    4 Beds
    982 Old Stage Rd  Chester
    2 Baths
    Detail oriented owners have updated and enlarged this horse and petfriendly home,lovely amenities for all! Views, radiant heat, three season porch, open floorplan, bamboo & ceramic floors, stainless a ... MLS # 3107990 [Read More!]
    Vermont Real Estate
    $625,000.00
     Sq Ft
    Chester VT  COM
    Beds
    26 Common Street  Chester
     Baths
    Charm, Location and Lots of Curb Appeal. This Classic Victorian is a gem, located in the historic village of Chester right on the green. The street level shop has been restored to its former glory a ... MLS # 4012707 [Read More!]
    Vermont Real Estate
    $589,000.00
    4050 Sq Ft
    Chester VT  HOME
    3 Beds
    352 Davidson Hill Rd  Chester
    3 Baths
    Upscale and grand with over 4000sqft of living space.Includes tile entry/mudroom,3 bedrooms,3 baths, open concept living/dining/kitchen,walk-in pantry. Master suite includes oversized walk-in closet w ... MLS # 3107516 [Read More!]
    Vermont Real Estate
    $574,900.00
    4486 Sq Ft
    Chester VT  HOME
    9 Beds
    225 Pleasant ST  Chester
    9 Baths
    Fantastic opportunity to live/work in a successful bed & breakfast inn. Close to Okemo, Bromley, Magic, etc. makes it a great ski home possibility too. 7 Guest Rooms and Suites, all with private baths ... MLS # 3103548 [Read More!]
    Vermont Real Estate
    $574,900.00
    4486 Sq Ft
    Chester VT  COM
    Beds
    225 Pleasant ST  Chester
     Baths
    Fantastic opportunity to live/work in a successful bed & breakfast inn. Close to Okemo, Bromley, Magic, etc. makes it a great ski home possibility too. 7 Guest Rooms and Suites, all with private baths ... MLS # 3103550 [Read More!]
    Vermont Real Estate
    $490,000.00
     Sq Ft
    Chester VT  COM
    Beds
    279-291 Pleasant St.  Chester
     Baths
    Unique property, suitable for many uses. 15000sf of commercial/industrial space in v.good condition. Has been used for food-processing. Town sewer & water. Single & 3-phase power. Forklift accessible ... MLS # 2802521 [Read More!]
    Vermont Real Estate
    $475,000.00
    3900 Sq Ft
    Chester VT  HOME
    4 Beds
    137 Main Street  Chester
    3 Baths
    This "Pink Lady" is perhaps the most photographed Victorian home in the village of Chester. It is as lovely on inside as the outside. It is completely updated from top to bottom. A grand home with ha ... MLS # 4006718 [Read More!]
    Vermont Real Estate
    $399,900.00
    2900 Sq Ft
    Chester VT  HOME
    4 Beds
    146 North Street  Chester
    2 Baths
    Historic Chester Stone Village property offering unique craftsmanship and old world charm you would expect from a period home. Wide pine floors, rumford fireplaces, detailed moldings, paneled wainscot ... MLS # 3103466 [Read More!]
    Vermont Real Estate
    $399,000.00
    3376 Sq Ft
    Chester VT  HOME
    3 Beds
    544 Remington Rd  Chester
    4 Baths
    No compromises taken on this solidly constructed newer home from frame to fixtures. 3 bed/2.5 baths up with gorgeous hardwood floors & stone fireplace in livingroom. Spacious familyroom in finished ba ... MLS # 3076379 [Read More!]
    Vermont Real Estate
    $395,000.00
    4443 Sq Ft
    Chester VT  HOME
    8 Beds
    232 Depot Street  Chester
    7 Baths
    Currently closed without furniture and some appliances, this 5-guest B&B with 3-bedroom owner's quarters has up-to-date permits and the sale includes signage, phone number and the name. It has great ... MLS # 3068931 [Read More!]
    Vermont Real Estate
    $379,000.00
    2560 Sq Ft
    Chester VT  HOME
    3 Beds
    758 Clemons Road  Chester
    2 Baths
    Single family home with horse barn on 25 acres. Located on quiet country road this 28' x 40' open concept cape has cathedral ceilings, loft area currently set up for office and full walk out basement ... MLS # 4021656 [Read More!]
    Vermont Real Estate
    $350,000.00
     Sq Ft
    Chester VT  LAND
    Beds
    159 Murdock  Chester
     Baths
    Big views of valleys and mountainsides from this private piece of land. Build your dream home, be it an incredible vacation home, primary estate or hunting preserve. This land is in land use and mar ... MLS # 4002069 [Read More!]
    Vermont Real Estate
    $325,000.00
    2200 Sq Ft
    Chester VT  HOME
    4 Beds
    39 North Street  Chester
    2 Baths
    A wonderful juxtaposition of bygone days and modern convenience w/400' of frontage on the Williams River. New country cook's kitchen w/antique walk-in pantry; roof 3 years new;Dining w/built-in cupboa ... MLS # 4010628 [Read More!]
    Vermont Real Estate
    $319,000.00
    2280 Sq Ft
    Chester VT  HOME
    2 Beds
    238 High ST  Chester
    2 Baths
    Classic 2 bedroom, 1 1/2 bath cape on 2.2 acres offering many attractive features including: spacious living rm w/fireplace, formal dining rm, 3 season rm w/granite fireplace, 1st floor laundry, attac ... MLS # 3106428 [Read More!]
    Vermont Real Estate
    $309,000.00
    2848 Sq Ft
    Chester VT  HOME
    4 Beds
    214 Vt Rte. 11 West  Chester
    3 Baths
    Antique/Vintage former Chester schoolhouse on 1.4 acres updated for contemporary living with 4 large bedrooms, 2.5 baths, eat-in-kitchen with professional gas stove, dining room, living room, family r ... MLS # 4011042 [Read More!]
    Vermont Real Estate
    $299,000.00
    2908 Sq Ft
    Chester VT  HOME
    4 Beds
    428 Depot ST  Chester
    2 Baths
    Walking distance to everything in town! Spacious rooms a woodstove, galley kitchen w/soapstone sink and all new appliances, built-ins, an exceptional barn with a studio, and a 2 car garage are only t ... MLS # 4020640 [Read More!]
    Vermont Real Estate
    $299,000.00
    2300 Sq Ft
    Chester VT  HOME
    4 Beds
    1425 Trebo Road  Chester
    2 Baths
    An antique farmhouse living in a modern world, yet exuding the country charm expected, inside and out. Perched just right on 2 acres, it offers a private rear yard and easy access to the village. Spac ... MLS # 4007687 [Read More!]
    Page 1 of 4 | - Next Page of Properties - Last Page

    Try all real estate & homes for sale in Windsor County Vermont!
    Recently Listed Homes For Sale in Windsor County Vermont

    VT MLS # 2728011 - HOME .. $14500000 .. 2356  Lovers Lane, Chester VT  .. Updated: 6/9/2010 6:45:56 PM
    VT MLS # 2819890 - LAND .. $14500000 ..   Lovers Lane, Chester VT  .. Updated: 6/9/2010 6:48:36 PM
    VT MLS # 2749060 - COM .. $1250000 .. 523 + 557  Rte 103 North, Chester VT  .. Updated: 7/19/2010 10:22:56 PM
    VT MLS # 3107990 - HOME .. $699000 .. 982  Old Stage Rd, Chester VT  .. Updated: 9/6/2010 10:01:39 AM
    VT MLS # 4012707 - COM .. $625000 .. 26  Common Street, Chester VT  .. Updated: 7/18/2010 12:26:51 PM
    VT MLS # 3107516 - HOME .. $589000 .. 352  Davidson Hill Rd, Chester VT  .. Updated: 7/15/2010 2:19:16 PM
    VT MLS # 3103548 - HOME .. $574900 .. 225  Pleasant ST, Chester VT  .. Updated: 8/27/2010 12:43:58 PM
    VT MLS # 3103550 - COM .. $574900 .. 225  Pleasant ST, Chester VT  .. Updated: 8/27/2010 12:43:58 PM
    VT MLS # 2802521 - COM .. $490000 .. 279-291  Pleasant St., Chester VT  .. Updated: 5/19/2010 3:51:02 PM
    VT MLS # 4006718 - HOME .. $475000 .. 137  Main Street, Chester VT  .. Updated: 7/23/2010 11:58:24 AM
    VT MLS # 3103466 - HOME .. $399900 .. 146  North Street, Chester VT  .. Updated: 5/20/2010 6:50:25 PM
    VT MLS # 3076379 - HOME .. $399000 .. 544  Remington Rd, Chester VT  .. Updated: 7/20/2010 8:51:29 AM
    VT MLS # 3068931 - HOME .. $395000 .. 232  Depot Street, Chester VT  .. Updated: 8/20/2010 2:57:25 PM
    VT MLS # 4021656 - HOME .. $379000 .. 758  Clemons Road, Chester VT  .. Updated: 9/1/2010 2:20:19 PM
    VT MLS # 4002069 - LAND .. $350000 .. 159  Murdock, Chester VT  .. Updated: 6/1/2010 11:29:41 AM
    VT MLS # 4010628 - HOME .. $325000 .. 39  North Street, Chester VT  .. Updated: 7/10/2010 6:54:27 AM
    VT MLS # 3106428 - HOME .. $319000 .. 238  High ST, Chester VT  .. Updated: 8/27/2010 11:17:28 AM
    VT MLS # 4011042 - HOME .. $309000 .. 214  Vt Rte. 11 West, Chester VT  .. Updated: 9/2/2010 8:37:31 PM
    VT MLS # 4020640 - HOME .. $299000 .. 428  Depot ST, Chester VT  .. Updated: 9/3/2010 10:06:45 AM
    VT MLS # 4007687 - HOME .. $299000 .. 1425  Trebo Road, Chester VT  .. Updated: 7/28/2010 11:24:57 AM
    VT MLS # 4012111 - HOME .. $295000 .. 33  Trebo Road, Chester VT  .. Updated: 8/5/2010 12:13:44 PM
    VT MLS # 4017875 - HOME .. $289000 .. 191  Green Mountain Turnpike, Chester VT  .. Updated: 9/1/2010 12:51:51 PM
    VT MLS # 3068613 - HOME .. $279000 .. lot 1  Flamstead Rd, Chester VT  .. Updated: 8/27/2010 12:44:52 PM
    VT MLS # 3068616 - HOME .. $279000 .. lot 2  Flamstead Rd, Chester VT  .. Updated: 8/27/2010 12:44:52 PM
    VT MLS # 3108571 - HOME .. $279000 .. 514  Elm Street, Chester VT  .. Updated: 5/27/2010 3:12:18 PM
    VT MLS # 3069213 - COM .. $279000 .. 128  Main ST, Chester VT  .. Updated: 8/20/2010 2:52:47 PM
    VT MLS # 3108291 - HOME .. $275000 .. 855  Marcs Dr, Chester VT  .. Updated: 8/24/2010 7:06:45 AM
    VT MLS # 4005258 - HOME .. $274500 .. 402  Flamstead Rd, Chester VT  .. Updated: 8/24/2010 5:03:56 PM
    VT MLS # 4020620 - LAND .. $256900 .. 1175  QUARRY ROAD, Chester VT  .. Updated: 8/26/2010 3:36:07 PM
    VT MLS # 3103985 - HOME .. $250000 .. 3873  Route 11 West, Chester VT  .. Updated: 8/19/2010 4:55:23 PM
    VT MLS # 3107347 - HOME .. $249900 .. 273  Depot ST, Chester VT  .. Updated: 6/16/2010 10:03:15 AM
    VT MLS # 3049259 - LAND .. $239000 ..   Brookside Dr, Chester VT  .. Updated: 5/19/2010 4:39:43 AM
    VT MLS # 3105224 - HOME .. $235000 .. 489  Main ST, Chester VT  .. Updated: 5/24/2010 11:36:25 AM
    VT MLS # 4013477 - HOME .. $235000 .. 650  Clemons Rd., Chester VT  .. Updated: 8/11/2010 3:08:54 PM
    VT MLS # 4021468 - HOME .. $230000 .. 371  Fletcher Hill Road, Chester VT  .. Updated: 9/1/2010 9:36:42 AM
    VT MLS # 3106762 - COM .. $228000 .. 46  South Main Street, Chester VT  .. Updated: 4/6/2010 8:30:23 AM
    VT MLS # 3051817 - LAND .. $225000 ..   Popple Dungeon Rd, Chester VT  .. Updated: 6/29/2010 10:02:55 AM
    VT MLS # 2820562 - HOME .. $220250 .. 57  River Street, Chester VT  .. Updated: 8/19/2010 11:33:15 AM
    VT MLS # 2820602 - MULTI .. $220250 .. 57  River Street, Chester VT  .. Updated: 8/19/2010 11:34:45 AM
    VT MLS # 4018335 - HOME .. $218500 .. 142  Meadow Road, Chester VT  .. Updated: 8/24/2010 9:08:15 PM
    VT MLS # 4013916 - HOME .. $204900 .. 3715  Trebo Road, Chester VT  .. Updated: 8/27/2010 9:48:12 AM
    VT MLS # 3069908 - HOME .. $199000 .. 1910  Popple Dungeon Rd, Chester VT  .. Updated: 7/19/2010 3:07:25 PM
    VT MLS # 4022423 - HOME .. $199000 .. 96  Kingsbury Rd, Chester VT  .. Updated: 9/6/2010 3:40:55 PM
    VT MLS # 3060364 - HOME .. $194000 .. 455  Depot ST, Chester VT  .. Updated: 5/24/2010 11:36:25 AM
    VT MLS # 4013575 - HOME .. $189900 ..   , Chester VT  .. Updated: 7/28/2010 12:54:13 PM
    VT MLS # 3105203 - HOME .. $184500 .. 755  Snell Rd, Chester VT  .. Updated: 8/23/2010 10:35:18 AM
    VT MLS # 4010252 - HOME .. $179900 .. 328  Snell Road, Chester VT  .. Updated: 7/27/2010 1:42:01 PM
    VT MLS # 4021590 - HOME .. $179000 .. 1582  Route 103 South, Chester VT  .. Updated: 9/1/2010 12:49:30 PM
    VT MLS # 4008678 - HOME .. $170000 .. 4928  Popple Dungeon Road, Chester VT  .. Updated: 9/2/2010 7:45:32 PM
    VT MLS # 3104964 - HOME .. $159900 .. 161  Maple Ridge Rd, Chester VT  .. Updated: 7/28/2010 12:57:43 PM
    VT MLS # 3068566 - HOME .. $154900 .. 63  Marshall Rd, Chester VT  .. Updated: 6/2/2010 4:42:04 PM
    VT MLS # 3108522 - HOME .. $149500 .. 862  Mattson Rd, Chester VT  .. Updated: 8/30/2010 8:06:21 AM
    VT MLS # 4012343 - COM .. $149000 .. 656  Depot Street, Chester VT  .. Updated: 8/30/2010 8:47:22 PM
    VT MLS # 3106620 - LAND .. $149000 ..   VT.Route 10 Dean Brook Road, Chester VT  .. Updated: 6/11/2010 1:34:56 PM
    VT MLS # 3105759 - HOME .. $145000 .. 254  Kevadus Circle, Chester VT  .. Updated: 8/27/2010 12:44:53 PM
    VT MLS # 4008708 - COM .. $145000 .. 0  Depot Street, Chester VT  .. Updated: 6/29/2010 11:28:13 AM
    VT MLS # 4006139 - MULTI .. $145000 .. 0  Depot Street, Chester VT  .. Updated: 7/20/2010 9:04:16 AM
    VT MLS # 3104083 - HOME .. $139000 .. 507  Snell Rd, Chester VT  .. Updated: 3/15/2010 2:14:15 PM
    VT MLS # 3106477 - HOME .. $134900 .. 3019  Popple Dungeon, Chester VT  .. Updated: 3/30/2010 9:32:35 AM
    VT MLS # 4016497 - HOME .. $129900 .. 468  VT Rte 103S, Chester VT  .. Updated: 9/1/2010 6:36:52 PM
    VT MLS # 3108220 - HOME .. $129900 .. 132  Kevadus Cir, Chester VT  .. Updated: 6/16/2010 9:58:59 AM
    VT MLS # 2816318 - MULTI .. $129000 .. 135  Grafton Street, Chester VT  .. Updated: 8/19/2010 11:46:30 AM
    VT MLS # 3075002 - LAND .. $125000 ..   Popple Dungeon Road, Chester VT  .. Updated: 6/9/2010 3:12:07 PM
    VT MLS # 3076252 - LAND .. $125000 .. 1436  Lovers Lane, Chester VT  .. Updated: 8/27/2010 12:44:52 PM
    VT MLS # 4003006 - HOME .. $125000 .. 9  River Street, Chester VT  .. Updated: 7/8/2010 1:54:55 PM
    VT MLS # 3107387 - LAND .. $119000 ..   Murdock Rd, Chester VT  .. Updated: 8/28/2010 10:51:17 AM
    VT MLS # 4016001 - HOME .. $111900 .. 2012  Route 103S, Chester VT  .. Updated: 8/20/2010 4:34:50 PM
    VT MLS # 3105581 - LAND .. $99900 ..   Williams Road, Chester VT  .. Updated: 6/9/2010 3:00:46 PM
    VT MLS # 4014112 - LAND .. $99900 .. 3098  Wyman Falls Rd, Chester VT  .. Updated: 7/25/2010 6:45:39 AM
    VT MLS # 3040780 - LAND .. $94900 .. Lot #1  Flamstead Road, Chester VT  .. Updated: 8/27/2010 12:44:51 PM
    VT MLS # 3040786 - LAND .. $94900 .. Lot #2  Flamstead Road, Chester VT  .. Updated: 8/27/2010 12:44:51 PM
    VT MLS # 3073591 - HOME .. $93500 .. 25  Circle Drive, Chester VT  .. Updated: 5/28/2010 6:18:35 PM
    VT MLS # 3063106 - LAND .. $90000 ..   Hidden Heights, Chester VT  .. Updated: 6/9/2010 2:26:32 PM
    VT MLS # 4021380 - LAND .. $59900 ..   Graham Road, Chester VT  .. Updated: 9/1/2010 10:09:41 AM
    VT MLS # 3071866 - LAND .. $39900 .. 1539  Chandler Road, Chester VT  .. Updated: 6/10/2010 3:20:41 PM
    VT MLS # 4015315 - LAND .. $36999 ..   Popple Dungeon, Chester VT  .. Updated: 8/2/2010 2:30:11 PM
    VT MLS # 3107345 - LAND .. $29900 ..   Maple Ridge Road VT. Rte. 1, Chester VT  .. Updated: 6/7/2010 4:55:56 PM
    VT MLS # 4021700 - RENTAL .. $2200 ..   Grafton Road, Chester VT  .. Updated: 9/3/2010 11:05:00 AM
    VT MLS # 4021683 - RENTAL .. $1300 ..   Grafton Road, Chester VT  .. Updated: 9/2/2010 10:43:20 AM

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