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Chester VT Real Estate

Chester is located in Windham County. Browse available Chester VT real estate below. 

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176 Meadow Road Chester VT 05143

Chester, VT176 Meadow Road

Price$349,000

Est. Mortgage: $/month

Pending

MLS Number 4880555

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,862
  • Construction Existing

Enjoy the sweet Vermont life in this spacious tri-level 5 bedroom, 2 bathroom renovated farmhouse with detached garage. As you walk through the front door, an over whelming feeling of warmth and comfort envelops you. With newly laid solid hickory flooring along with stunning hand hewn beams which compliment the striking cathedral ceilings above the living room. We invite you to explore this extraordinary open space concept home. This forever home features a brand new heating system along with updated plumbing and electrical. Truly move in ready. The master suite has a private deck to enjoy your morning coffee as you watch the wildlife and listen to the zen sounds of the Williams River from your very own modern farmhouse oasis. The kitchen boasts hand poured concrete counter tops and new state of the art stainless steel appliances. Conveniently located on a quiet dead end street, overlooking the majestic Buttonwood Farms rolling green fields. A stroll around the block leads to the lively charm of Chester Village. With shops, dining and more. A short 15 minute drive takes you to Vails Okemo mountain resort for summer and winter fun, with even more shopping and excursions to choose from. Not to mention the Vas trail access. A property not to be missed. Schedule your showing today!

Listed by Hergenrother Realty Group and Daniel Preston of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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125 and 61 Trebo Road Chester VT 05143

Chester, VT125 and 61 Trebo Road

Price$249,000

Est. Mortgage: $/month

MLS Number 4878812

  • Residential Single Family
  • Square Feet 1,900
  • Bathroom 2
  • Construction Existing
  • Bedrooms 2

This unique home has been a great seasonal property as well as a full time home during it's lifetime. Cozy and simple in design with a comfortable common area open to the eat-in kitchen flanked on either side by bedrooms and baths. On the lower level walk in to a den or family room with a wood stove. Then, up the stairs to the main living quarters. Enjoy the one car garage which has walk in access to the home. PLUS: A additional small cottage is on the lot. Perfect for an in law suite or rental or caretaker. A tenant currently resides there and would like to stay.

Listed by Amanda Stearns and Joan Morey of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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690 Trebo Road Chester VT 05143

Chester, VT690 Trebo Road

Price$475,000

Est. Mortgage: $/month

Pending

MLS Number 4877533

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,112

Country colonial playground - Everything just feels right from the moment you pull in the driveway and slide into the large two car attached garage. Spacious oversized modern kitchen with cozy woodstove in the dining area will keep you warm on those long winter days. A half bath, bedroom and "comfy" living room round out the main floor. A large deck spans the full width of the house to take in the beautiful eastern views and fields. Upstairs are a private master suite with a beautiful tiled bath, two bedrooms and another tiled bath. The full basement is ready for a transformation to a movie or rec room. Current owners have sheep and chickens but you can remove the fencing and open the land back up. There are endless trails woven throughout the 19 acres consisting of open fields and woodland. There's even a small creek that runs through the bottom corner of the lot. Outbuildings consist of a heated "she shed", a free standing two car work barn, a run in shed and a chicken coop. This updated home is equipped with a state of the art solar array. If you are looking for your slice of Vermont, this charming house is minutes off Rte 103 and a five minute ride to Smitty's general store for some of the best deli meats, craft beer and sandwiches in the area.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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133 Marshall Road Chester VT 05143

Chester, VT133 Marshall Road

Price$245,000

Est. Mortgage: $/month

Pending

MLS Number 4876951

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 1
  • Square Feet 1,443

Beautifully renovated split level home with 4 bedrooms and an open concept kitchen/living space. This bright and cozy home is located in a quiet neighborhood, conveniently located within walking distance to historic downtown Chester. There is plenty of parking and a garden/storage shed. A lovingly landscaped front yard bordered with antique stone hitching posts and ornamental trees frames this sunny home. The real magic of this property is the private backyard. Step out from the kitchen onto the expansive deck which overlooks a beautiful play-friendly flat yard with custom stone walls, built-in stone benches, and hearty perennials. Complete with a fire pit, jacuzzi tub, and overlooking the gorgeous South Branch Williams River, perfect for a summer dip, this private backyard truly feels like a world of your own. Great place for fun and entertaining. Easy access to local hiking trails and ski resorts Okemo, Stratton, Magic Mountain, and Bromley. Move in ready! Plan for a showing today!

Listed by Jason Saphire of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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278 VT RT 11 West Chester VT 05143

Chester, VT278 VT RT 11 West

Price$179,000

Est. Mortgage: $/month

MLS Number 4876546

  • Mobile
  • Listing Agent Name Daire Gibney
  • Bedrooms 3
  • Year Built 2006
  • Square Feet 1,512

This spacious double wide features a large master en suite, cozy fireplace, two full bathrooms and an open concept living area. Situated on a bright and open 3 acre lot this home has quick access to Chester Village and the surrounding mountains. One level living is the way to go whether you are retiring to a more easily manageable home or you are just starting out with your first home. This property is turnkey and ready to go. Come see this lovely home today.

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 Church Street Chester VT 05143

Chester, VT14 Church Street

Price$329,000

Est. Mortgage: $/month

MLS Number 4874093

  • Multifamily
  • Units 5
  • Square Feet 4,700
  • Bathroom 5
  • Acreage 0.75

Fantastic investment opportunity. 5 Unit multi-family located in the heart of the village on the corner of Church and Main. One two bedroom, 3 one bedroom and one studio. Excellent condition throughout. Many updates including standing seam roof in approx 2016, 2 of the units totally renovated in 2018 and 2019, new propane furnace and heating system in 2018, multiple windows replaced, rear deck and stairs replaced in 2018. This is a revenue producer. Live in one unit and rent the other for income. Many possibilities exist with the lovely property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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308 Church Street Chester VT 05143

Chester, VT308 Church Street

Price$245,000

Est. Mortgage: $/month

MLS Number 4873684

  • Residential Single Family
  • Bedrooms 2
  • Square Feet 1,354
  • Bathroom 1
  • Construction Existing

This pretty home sits proudly on Church Street and will, with a little effort, make a fabulous home. Just a few minutes walk to the center of the village and with three major ski resorts all within 15 -30 minutes drive this will be perfect for a second OR primary home. The house has had several updates over the years leaving you the opportunity live in comfort as you put your finishing touches to the remaining spaces. The 2 car garage is an excellent space with plenty of storage up above. The lot has lovely stone walls and a nice private area in the back to enjoy with lots of space for flower or vegetable gardens. A lovely old attached barn also offers opportunity to restore and create additional space for whatever you decide. This home is being offered As Is. Come see this quaint Chester home today!

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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316 Depot Street Chester VT 05143

Chester, VT316 Depot Street

Price$180,000

Est. Mortgage: $/month

MLS Number 4871589

  • Multifamily Multi-Family
  • Square Feet 2,135
  • Units 4
  • Acreage 0.5

Chester Vermont multi family , excellent rental history. Conveniently located in town. 4 units plus a garage barn space.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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198 Peck Road Chester VT 05143

Chester, VT198 Peck Road

Price$169,000

Est. Mortgage: $/month

MLS Number 4871598

  • Multifamily Multi-Family
  • Square Feet 1,824
  • Units 2
  • Bathroom 2
  • Acreage 0.57

Peck Road Chester Vt. multi family home 1 two bedroom and 1 one bedroom , Live in one rent the other. minutes to town.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1377 VTRT 103 Chester VT 05143

Chester, VT1377 VTRT 103

Price$400,000

Est. Mortgage: $/month

MLS Number 4871606

  • Multifamily
  • Square Feet 2,280
  • Units 2
  • Bathroom 2
  • Acreage 3

Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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981 Cavendish Road Chester VT 05143

Chester, VT981 Cavendish Road

Price$220,000

Est. Mortgage: $/month

MLS Number 4871275

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,700

Country home perched on a one acre lot in Chester, Vermont! Ready and waiting! Welcome yourself through the convenient mudroom to the spacious living room warmed by a pellet stove. Continue on to find an eat in kitchen with granite counter tops. Enjoy dinner by the stone fireplace! Peer around the corner and see the cozy master bedroom suite with it's full bath. Traveling up the stairs, you will find two more bedrooms with a bonus room ready for your office or play space! Other notable features include the private country location, equidistant to Ludlow and Chester villages, convenience to I-91, skiing, shopping, golf, not to mention the newly engineered 3 bedroom septic system. A country gem worth visiting!

Listed by Amanda Stearns of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$1,135,000

Est. Mortgage: $/month

MLS Number 4869423

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,044

This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to many of Vermonts best ski areas which create an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands including a sugarbush with state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$539,000

Est. Mortgage: $/month

MLS Number 4845016

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Square Feet 5,242

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5051 VT RT 103 N Chester VT 05143

Chester, VT5051 VT RT 103 N

Price$105,000

Est. Mortgage: $/month

MLS Number 4837679

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 864

Single level living with large two bay garage. This house is located an equal distance to Chester and Ludlow via VT RT 103, both offer small town shopping and dining. Ludlow is home to Okemo Mountain Ski Resort and is a short 10 minute drive. Bring your imagination with you when you view this property, the possibilities are endless.

Listed by Amanda Stearns of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

371 Dodge Road Chester VT 05143

Chester, VT371 Dodge Road

Price$69,000

Est. Mortgage: $/month

MLS Number 4830453

  • Mobile
  • Listing Agent Name Daire Gibney
  • Year Built 1980
  • Bedrooms 2
  • Square Feet 858

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Stage Road Chester VT 05143

Chester, VTStage Road

Price$149,000

Est. Mortgage: $/month

MLS Number 4827417

  • Mobile
  • Listing Agent Name Daire Gibney
  • Year Built 1996
  • Bedrooms 2
  • Square Feet 924

This picturesque lot commands a stunning view from its lofty perch overlooking Stage Road in Chester. The lot is a mix of open field and forest. This would be perfect for your new dream home, gentleman's farm or simply a great getaway location. This location has so much potential for expansion and will be easily developable. Just insert your imagination.

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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698 Vermont RT 11 Chester VT 05143

Chester, VT698 Vermont RT 11

Price$650,000

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 12
  • Square Feet 6,848

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated September 26, 2021.