Welcome to Watson Realty & Associates PLC

Sign Up Today!

Get fresh listings via email, save your favorite listings, match with similar properties, and unlock additional property info.

Create Your Account

Do not fill in this field:

Already have an account? Log in

Chester Vermont Real Estate

Windsor County
Chartered: February 22, 1754
Area: 35,773 Acres = 55.9 Square Miles
Population (US Census, 2000): 3,044
Population Density (persons per square mile): 54.5

Schools

Windsor Southwest Supervisory Union 802-875-3365
Chester-Andover School 802-875-2108
Green Mountain Union High School 802-875-2146

Chester Vermont is a short drive from Springfield Vermont and Bellows Falls Village Vermont. A picturesque downtown with family-owned shops, restaurants, and bread and breakfasts beckons residents for an afternoon stroll along Main Street or a picnic in the town green. An annual fall craft show and a late winter chili contest are just a taste of the goings-on in this quaint Vermont town. Chester Vermont real estate and properties puts Vermont skiing less than an hour away, like Okemo Mountain Resort, Ascutney Mountain Resort, Pico Ski Resort, Killington Resort, Magic Mountain Ski Resort, Stratton Mountain Ski Resort, Suicide Six Ski Area, and Bromley Mountain Ski Resort.

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$924,000

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Area Near Skiing, Rural
  • Acreage 509.73
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 509+/- acres has it all. Made up of 4 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Stage Road Chester VT 05143

Chester, VTStage Road

Price$622,650

Est. Mortgage: $/month

MLS Number 4931759

  • Land
  • Acreage 296.5
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning property has it all. Made up of 3 contiguous preexisting lots with a right of way via Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

7 Pine View Drive Chester VT 05143

MLS Number 4908570

  • Commercial
  • Year Built 2006
  • Square Feet 3,164
  • Acreage 1.56

Excellent opportunity presents itself with this outstanding commercial property located on Route 103 Chester. High volume traffic and exposure gives this property unlimited potential for the entrepreneur buyer. This exceptional post and beam structure sits on 1.56 acres and was built in 2006. Currently used as office space, it had been a retail shop, gallery and cafe in the past. Mixed use zoning allows for a future residential possibility. Over 3,000 usable square feet, ample parking, radiant heat, gorgeous tile flooring, natural wood beams. Town water and septic hooked up to the town line. Bring your vision and energy and create your dream.

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

12 Common Street Chester VT 05143

MLS Number 4928621

  • Commercial
  • Year Built 1820
  • 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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 7:24 AM EDT.