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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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683 Church Street Chester VT 05143

Chester, VT683 Church Street

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4932616

  • Residential Single Family
  • Construction Existing
  • Square Feet 5,566
  • Bedrooms 7
  • Bathroom 4

Spectacular 7-bedroom country home on 45+/- acres located in Chester, Vermont. This luxurious home combines the beauty of its architectural features with its magnificent country setting. Starting in the kitchen, there is an open kitchen design, large center island, a breakfast bar, a pantry with an additional oven and wine cooler, an oversized kitchen sink, and a commercial grade oven fit for a chef. In the living room there is an amazing stone fireplace with vaulted ceilings, an open post and beam design, and floor to ceiling windows. The dining room is sizeable and could be a perfect place for friends and family to gather for a meal. The main level has two bedrooms located near the back of the home. Both include their own private bathrooms. Upstairs, above the three-car garage, there is a spacious primary suite with a full bath and walk-in closet. On the second floor there are three bedrooms, two of those bedrooms share a beautiful bathroom and the other bedroom has its own private bath. There are two lofted areas on the second floor. One of the lofts is spacious enough for a pool table and an extra living room space. This home includes 4 wood burning fireplaces, 1 outside fireplace and, 2 wood burning stoves. Come see a truly spectacular home that offers unique architectural accents to make you feel like you are in a house fit for royalty. Taxes are based on current town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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837 VT 11 West Chester VT 05143

Chester, VT837 VT 11 West

Price$329,900

Est. Mortgage: $/month

MLS Number 4932398

  • Residential Single Family
  • Square Feet 2,412
  • Bathroom 2
  • Construction Existing
  • Bedrooms 4

This well-loved home sits handsomely overlooking the middle branch of the Williams River and provides exceptional access to all that VT has to offer. Just a few moments from the village of Chester and an easy drive to Okemo, Stratton or Magic Mountains. And with I91 just 15 minutes away this is a great access point for commuting and exploring the area. This home has so much potential whether it be a full-time residence, home-based business or vacation getaway. The "workshop/office" with almost 1500 square feet of additional space that can easily be a rec room; garage, host your toy collection, or additional living space. The choice is yours!!Abutting town-owned land on one side and an open meadow on the other this lot feels vast yet easily maintained. There is a wonderful 2-stall horse barn with power and water. Also, there is a neat fenced-in area for the precious pooch in your life. A small-scale home hobby farm would be ideal on this well-laid-out level lot. The central breezeway provides access to the large patio and gardens that overlook the river behind and will provide an exceptional outdoor living space! Come see this wonderfully versatile home today!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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312 North Street Chester VT 05143

Chester, VT312 North Street

Price$365,000

Est. Mortgage: $/month

MLS Number 4931626

  • Residential Single Family
  • Bathroom 1
  • Bedrooms 4
  • Square Feet 2,090
  • Construction Existing

This charming Greek revival located within the stone village of Chester, VT, has remained true to it's original in many ways. The yard is small but inviting. A beautiful view, an apple tree, raspberry bushes and white lilacs and a side patio off the kitchen are all yours! There are many closets as well as a larger enclosed area that could be used as a sewing or art room. The back stairway from the master leads you to to the kitchen where you'll find plenty of room, douglas fir flooring and exposed beams. Much of the house has pine flooring and many replacement windows. There is a detached 16x24 studio that's finished space which has electric and heat. Perfect for someone to have a small business or office on site. There is a large attached two bay garage with custom doors as well as another separate one bay detached garage, both with ample storage for cars, ATVs or snowmobiles. Chester is a vital local arts and music community that's close proximity to many VAST trails as well as 30 minutes from several major ski areas. A new propane furnace is being installed 11/21, along with a new water heater.

Listed by Heather Gleim of Walnut Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$525,000

Est. Mortgage: $/month

MLS Number 4929151

  • Multifamily
  • Bathroom 2
  • Units 3
  • Square Feet 4,060
  • Acreage 0.25

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2 bedroom 1 bathroom with much potential! Along with the many benefits of this properties location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added recently as well.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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95 Church Street Chester VT 05143

Chester, VT95 Church Street

Price$495,000

Est. Mortgage: $/month

Pending

MLS Number 4927983

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,794

Welcome to 95 Church St in the charming town of Chester. This 1800's home has seen many changes over the years including most recently a whole house renovation. This is a great property for someone that loves the charming features of an older home but in turn key condition. Renovations include but are definitely not limited to the kitchen, bathrooms, flooring, windows, heating systems including in floor radiant heat, siding, electrical, pex plumbing, spray foam insulation, and a new standing seam roof. The kitchen features beautiful hand made cherry cabinets with custom pantry cabinets as well. While we are talking about cabinets the walk-in closet features walnut shelving and drawers. The floors throughout most of the home are a beautiful hickory. In addition to the the two bathrooms there is an en suite bathroom that is ruffed in and waiting for your final touches. Sit back and enjoy the village location from the screened in porch or patio.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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739 Gould Road Chester VT 05143

Chester, VT739 Gould Road

Price$235,000

Est. Mortgage: $/month

MLS Number 4927784

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Square Feet 1,664
  • Bedrooms 4

The owners have done some significant work on the lower level, removing floor tiles, wall paper and have freshly painted! At it's new reduced price it's a great value. This four-bedroom, one-bath home is located in Chester, Vermont on a peaceful and quiet road. As you enter the house, you walk into the large living room that has a wood burning stove and skylights that provide great natural light. Directly through the large living room is the dining room and kitchen. The main level also features a full bathroom, laundry room and has access to the secluded back deck. Two of the bedrooms are located on the main floor near the living room, and both bedrooms are spacious with wooded views. As you go down the stairs, there are two more bedrooms and an exterior door. For those that enjoy fresh air, the front of the house features a screened in porch and the rear large deck is ready for stargazing. The house is a blank canvas ready to update to your vacation dream home. Taxes are based on current town assessment. This property has been used only seasonally since 1986.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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346 First Avenue Chester VT 05143

Chester, VT346 First Avenue

Price$249,000

Est. Mortgage: $/month

MLS Number 4926996

  • Residential Single Family
  • Bathroom 2
  • Square Feet 1,610
  • Construction Existing
  • Bedrooms 4

Welcome to 346 First Avenue! This family home is ready for new owners to make their own lifetime of memories! Come sit on the welcoming front porch and watch the Green Mountain Flyer or just listen to birds chirping from the perennial gardens. Stroll to the local store and downtown Chester. Only a few minutes drive to several ski areas, shopping and easy access to I91. Once inside you can tell this home was LOVED! Lots of light, pretty woodwork and main level bedroom are on your wish list and this home offers all those things. Kitchen is functional with tons of cabinet space and counter top space. Need more room? The attached barn is ready for your ideas! Expand the kitchen and take advantage of the large pantry! The bedrooms are spacious and upstairs bathroom is sunny and bright! This home is deserving of the work that someone will put into it and will be well worth it and most of what needs to be done is cosmetic. Two car garage with lean-to off the back are perfect to hold "all the toys, tools and equipment". Unfinished space in the upper part of the garage could be awesome game room, man cave or yoga studio! This is a truly wonderful property just waiting for you...come take a look.

Listed by Lisa Kelley of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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784 VT RT 103 N Chester VT 05143

Chester, VT784 VT RT 103 N

Price$229,000

Est. Mortgage: $/month

Pending

MLS Number 4926106

  • Residential Single Family
  • Square Feet 1,214
  • Bedrooms 3
  • Construction Existing
  • Bathroom 1

Ranch style home on 9.2 acres. This home is solid and very functional but could use updating. Good sized kitchen with ample counter space and cabinets. Eat in with dining area. Large living room and 3 bedrooms with full bath completes this easy keeper home. Unfinished walkout basement. The house is set up off of Rt 103 and provides total privacy. Cannot be seen from the road. The 9.2 acres is mostly wooded and has level areas beyond the home giving you the potential to build another home in the future should you desire. The location is steller only a few minutes to town and just 10 miles to Okemo Mountain resort. There is a lot to like here and wonderful possibilities exist. Come take a look!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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3838 Trebo Road Chester VT 05142

Chester, VT3838 Trebo Road

Price$335,000

Est. Mortgage: $/month

MLS Number 4925816

  • Residential Single Family
  • Bedrooms 2
  • Construction Existing
  • Square Feet 1,236
  • Bathroom 2

Ever dreamed of getting away from it all? Here is your chance to own a secluded, mountain home in the woods! It offers the best of all worlds- privately tucked away on nearly 26 acres but only 12 miles to Okemo Mountain and minutes to the quaint town of Chester! The living room is the star of the show for this house with cathedral ceilings, ample picture windows and a large deck for entertaining or just watching the wildlife. There are two bedrooms on the main floor and a bonus lofted room with it's own balcony. The galley kitchen opens to the living room. Large unfinished walkout basement with sliding doors and a bathroom could be finished to provide another living area and has a pellet stove as an additional heating source. Okemo Mountain is less than 20 mins, Stratton and Killington Mountains less than 50 mins, close to VAST trail and less than 5 miles to Chester town center with dining and shopping. 2.5 hours to Boston

Listed by Mandolyn McIntyre of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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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538 Clemons Road Chester VT 05143

Chester, VT538 Clemons Road

Price$410,000

Est. Mortgage: $/month

Pending

MLS Number 4919284

  • Residential Single Family
  • Bathroom 3
  • Bedrooms 3
  • Construction Existing
  • Square Feet 1,900

All the possibilities! Prime location, desirable size, level secluded lawn, oversized three bay garage with ample storage...the list goes on and on. Enter through the attached garage and into the wonderful mudroom to find yourself comfortably moving around the open floor plan. This well maintained home is ready for all of your ideas and plans. Let's talk about the garage! Built with big ideas in mind, this building can house all of your toys and equipment. Equipped with oversized doors and one drive-through bay. The office area and upstairs storage space offer endless possibilities. This building is a huge bonus. The location is spectacular, complete with a beautiful fire pit and tons of open space for all of your gardening visions. We can't wait to show you what this property has to offer!

Listed by Chelsea Bevis of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Oct 6, 2022
* 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$1,685,000

Est. Mortgage: $/month

MLS Number 4918189

  • Residential Single Family
  • Square Feet 4,444
  • Bedrooms 4
  • Construction Existing
  • Bathroom 5

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 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 a 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 private 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: 6.66% last updated on Oct 6, 2022
* 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$170,000

Est. Mortgage: $/month

MLS Number 4871589

  • Multifamily
  • Units 4
  • Square Feet 2,135
  • 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: 6.66% last updated on Oct 6, 2022
* 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
  • Units 2
  • Bathroom 2
  • Square Feet 2,280
  • 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: 6.66% last updated on Oct 6, 2022
* 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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Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 October 7, 2022 2:39 AM EDT.