Chester

Explore the latest real estate for sale in Chester, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-760-3100 or contact us online.

Create a free account to save your favorite Vermont real estate listings and get notified when similar properties become available.

683 Church Street Chester VT 05143

Chester, VT683 Church Street

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4932616

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 6

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. There is another half bathroom near the mudroom. 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: 6.58% last updated on Nov 23, 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
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • 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: 6.58% last updated on Nov 23, 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
  • County Windsor
  • Square Feet 22,203,839
  • Acreage 509.73

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: 6.58% last updated on Nov 23, 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

604 Church Street Chester VT 05143

Chester, VT604 Church Street

Price$649,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4933748

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

A true Vermont setting - perched on a knoll with 10 acres bordering both sides of the Williams River, the landscape overlooks a swimming pond, gardens, fruit trees, perennials and beautiful vistas. Share a meal in the open updated kitchen that adjoins the dining area with fireplace and living area with a wood stove. Each of the bedrooms have their own bath. The detached post and beam barn, constructed in 2008, is fully insulated, has three levels including a drive out lower level with water, a Jotel wood stove and electricity. Recent improvements include a new septic system (2017), new heating system (2016), roof (2013), kitchen and baths (2018, 2021). Many specimen trees including several types of apples, plums, hazelnuts and more. A magical spot to take in all four seasons - watch the Green Mountain Flyer go by in the fall, ski at nearby Okemo Mountain in the winter, and swim in the pond in the summer!

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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
  • County Windsor
  • Square Feet 12,915,540
  • Acreage 296.5

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: 6.58% last updated on Nov 23, 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
Active With Contract

MLS Number 4908570

  • Commercial
  • County Windsor
  • 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: 6.58% last updated on Nov 23, 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

656 Main Street Chester VT 05143

Chester, VT656 Main Street

Price$575,000

Est. Mortgage: $/month

MLS Number 4933749

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Historic turn of the Century 3+ bedroom, 2.5 bath Victorian on .37 +/- acres known as the Walter Austin house in Chester Village. This grand home has many period features fusing qualities from the Gilded Age to a more contemporary style. The first floor features a tiled mudroom, elegant foyer and spacious living room with an attractive gas marble fireplace. Pocket doors open from the living room to the large formal dining room. The classically styled kitchen has a breakfast bar, Corian countertops and accented glass paned cabinets. The splendid great room with cathedral ceilings and skylights has a palladium-crowned triptych window that showcases a pastoral view which will delight year round. The second floor features 3 bedrooms and continues the elegance of the foyer with crown moldings and stained glass windows. A spacious bathroom with a clawfoot soaking tub and tiled shower is located across the hall from a laundry room with half bath. The finished third floor Aerie offers two cozy rooms for office and study or guest overflow. Outside is a lovely deck with awning, a courtyard and- the centerpiece of the backyard- a luxurious relaxing swim spa. In addition to the 1 car garage, a 2 story post & beam barn provides additional garage and workshop space with a second floor rec room or private office. Proximity to skiing, Chester Village Green and rec area make this a wonderful primary or second home.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

12 Common Street Chester VT 05143

MLS Number 4928621

  • Commercial
  • County Windsor
  • 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: 6.58% last updated on Nov 23, 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
  • County Windsor
  • Bathroom 2
  • 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 to the whole building recently as well.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

81 Main Street Chester VT 05149

MLS Number 4937012

  • Commercial
  • County Windsor
  • Square Feet 4,264
  • Acreage 0.44

Welcome to 81 Main Street! Built in 1820 and located in the heart of the Chester village, this property is historically known as the Guy Earle House and has been a year round vacation home, short term rental property, dance studio and psychologist's office. This quintessential VT gem on .44 acres+/- features 5 bedrooms and 4 baths. Among its many attractive features are a large living room with wood burning fireplace, formal dining room, two first floor bedrooms, one en suite and an additional bathroom. The 2nd floor includes a large living area, en suite bedrooms, a bonus game room with a handsome wet bar, hand-crafted from school benches and a pellet stove. Additional Features include: first floor laundry, mudroom/workshop and unfinished attic space. The double lot has generous parking, an oversized 1 car detached garage with potential space to be finished and a separate shed for gardening in the large level yard. Has been used as owner occupied with 2 commercial units. Close to 5 ski areas, recreational activities and year round fun! Also listed as mls#4129143.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

81 Main Street Chester VT 05143

Chester, VT81 Main Street

Price$479,000

Est. Mortgage: $/month

MLS Number 4929143

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 4

Welcome to 81 Main Street! Built in 1820 and located in the heart of the Chester village, this property is historically known as the Guy Earle House and has been a year round vacation home and short term rental property. This quintessential VT gem on .44 acres+/- features 5 bedrooms and 4 baths. Among it's many attractive features are a large living room with wood burning fireplace, formal dining room, two first floor bedrooms, one en suite and an additional bathroom. The 2nd floor includes a large living area, en suite bedrooms, a bonus game room with a handsome wet bar, hand-crafted from school benches. and a pellet stove. Additional Features include: first floor laundry, mudroom/workshop and unfinished attic space. The double lot has generous parking, an oversized 1 car detached garage with potential space to be finished and a separate shed for gardening in the large level yard. The 4 porches adorning the house offer outdoor covered gathering spaces. Stroll to the green for coffee and browse the shops. Close to 5 ski areas, recreational activities and year round fun! Also listed as Commercial see mls# 4937012

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

1377 Vtrt 103 Chester VT 05143

Chester, VT1377 Vtrt 103

Price$400,000

Est. Mortgage: $/month

MLS Number 4871606

  • Multifamily
  • County Windsor
  • 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: 6.58% last updated on Nov 23, 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

32 VT Route 10 Chester VT 05143

MLS Number 4905205

  • Commercial
  • County Windsor
  • Square Feet 3,306
  • Acreage 9.4

Outstanding business location! This great 9.4 acre parcel has retail space, walk-in refrigerator and freezer, and a commercial kitchen at ground level, with residential space above for owner/operator or staff! The property is located at the intersection of two state highways - Route 10 and Route 103 which provides excellent access for motorists and tourists. Permitting allows seating for 22. Imagine your local farm to table eatery, a great burger place or maple creamery with activities in the field - perhaps even a 4-wheeler and snowmobile track. This property has amazing possibilities! Bring your passion and imagination when you come see this prime location. Schedule a showing today!

Listed by Suzanne Garvey and Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

3208 Green Mountain Turnpike Chester VT 05143
Active With Contract

MLS Number 4933652

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

Simplicity is the key to this newly renovated 3 bedroom, 2 bath country cape on .33 acres +/- in Chester Stone Village. Located just steps away from the walking loop and poised to enjoy the picturesque open valley view, this thoughtfully reconstructed and reimagined 1880 homestead is filled with natural light and wide pine flooring and will capture your heart with its minimal artisan sensibility. The open concept floorplan is accentuated with exposed beams and features a first floor bedroom and full bath with laundry hookups. The expanded second floor features 2 additional bedrooms with ample, walk-in storage and a tiled full bath. Across from the Williams River and convenient to skiing, shopping, Upper Valley, I91 and beyond.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

312 North Street Chester VT 05143

Chester, VT312 North Street

Price$365,000

Est. Mortgage: $/month

MLS Number 4935430

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 1

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, 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 30minutes from several major ski areas. A new propane furnace was installed in November 2022, along with a new water heater.

Listed by Heather Gleim of CENTURY 21 MRC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

Grafton Road Chester VT 05143

Chester, VTGrafton Road

Price$360,000

Est. Mortgage: $/month

MLS Number 4903171

  • Land
  • County Windsor
  • Square Feet 6,189,876
  • Acreage 142.1

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 142.1 +/- lot is made up of two separate but adjoining parcels, one in Chester comprising of 70.1 acres and 72 acres in Grafton. Each has road frontage on onto route 35 between Chester and Grafton. If you have conservation on your mind both parcels are enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded with small ponds on the Chester lot. There are also a network of logging trails throughout the property. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

3838 Trebo Road Chester VT 05142

Chester, VT3838 Trebo Road

Price$335,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4925816

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 2
  • 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: 6.58% last updated on Nov 23, 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

837 VT 11 West Chester VT 05143

Chester, VT837 VT 11 West

Price$329,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4932398

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

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: 6.58% last updated on Nov 23, 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

17 Grafton Street Chester VT 05143

Chester, VT17 Grafton Street

Price$305,000

Est. Mortgage: $/month

MLS Number 4936368

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a 2 unit apartment, it's top floor consists of a two bedroom one bath unit while the downstairs is set up as a one bedroom cozy apartment. The house can very easily be converted back to a single family home by simply removing a wall on the lower level which was installed only a few years ago. The whole house has electric and plumbing updates. Two recent hybrid water heaters and furnace. A new roof was just installed. Priced to sell, please note current tenants are occupying both units. Appointments with at least 48 hours notice are needed. Showings will be scheduled in blocks of time. Preferred closing is this spring. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Taxes are based on current town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

17 Grafton Street Chester VT 05143

Chester, VT17 Grafton Street

Price$305,000

Est. Mortgage: $/month

MLS Number 4936369

  • Multifamily
  • County Windsor
  • Square Feet 1,824
  • Acreage 0.37

Classic 1852 brick colonial home located on the corner of Grafton and Main Streets in beautiful downtown Chester. A short stroll to the town green, library, shops and antique shops. Currently a two unit apartment, it's top floor consists of a two bedroom one bath unit while the downstairs is set up as a one bedroom cozy apartment. The house can very easily be converted back to a single family home by simply removing a wall on the lower level which was installed only a few years ago. The whole house has electric and plumbing updates. Two recent hybrid water heaters and furnace. A new roof was just installed. Priced to sell, please note current tenants are occupying both units. Appointments with at least 48 hours notice are needed. Showings will be scheduled in blocks of time. Preferred closing is this spring. This is an excellent opportunity to either convert the home back to a single family or live in one and rent the other. Taxes are based on town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

547 Williams Road Chester VT 05143

Chester, VT547 Williams Road

Price$299,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4937157

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

Lovely ski chalet in Chester - just in time for winter! Have you ever wanted to kick back and relax at your Vermont getaway? Here's your chance. Seclusion and serenity are your friends here, and this home on 10+ acres is perfect for a ski vacation getaway. It has been lovingly maintained and is ready for new owners. Enjoy the partially open backyard and fire pit. Then, head inside to warm up next to the cozy fireplace. Vaulted ceilings and the open-concept kitchen/living space make it perfect for entertaining. The two main level bedrooms share a full bathroom. The primary bedroom is upstairs, just off the loft area which is perfect for your at-home office, and features its own 3/4 attached bathroom. New furnace and huge propane tank - great for epic winters. Williams Road is on the VAST trail. The driveway is steep but nothing crazy, with plenty of room to turn around at the top. Close to ski trails but far enough away to forget about the traffic for a while. Fiber optic internet is on site. A bit on how to get here: "You can't get there from here". Williams Road is a dirt road that follows the Williams River. Be careful not to follow phone GPS, but follow written directions. Enter from Popple Dungeon Road onto Nudist Camp Road. Don't wait. This one won't last long! Video tour available upon request.

Listed by Rachael Hyjek of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

63 Highland Court Chester VT 05143

Chester, VT63 Highland Court

Price$259,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4937151

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1

Beautifully maintained 3 BR Ranch only minutes to town. Home boasts 3 good sized bedrooms including a primary with Bath/Laundry room and direct access to the side deck. Entryway Mudroom with built in cabinetry that serves as a pantry. Nice kitchen and dining area that opens up to a large living room. The sunroom is a bright space overlooking the yard with access to the side deck. Can also be used as an excellent office space. Hardwood floors throughout with the exception of the kitchen. Full unfinished basement with garage and stair access to the main floor. The driveway is paved and you also have a paved landing for parking by the side entrance which is used as the main entry. The 1/2 acre lot is level with a great backyard. Close to several major ski areas and all of what Vermont has to offer. This is a gem so come and take a look.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

346 First Avenue Chester VT 05143

Chester, VT346 First Avenue

Price$249,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4926996

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

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: 6.58% last updated on Nov 23, 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

Lot 4 VT Route 103 North Chester VT 05143

Chester, VTLot 4 VT Route 103 North

Price$238,000

Est. Mortgage: $/month

MLS Number 4937718

  • Land
  • County Windsor
  • Square Feet 5,216,310
  • Acreage 119.75

Here is land with a variety of options! Streams, open areas, wooded areas & various levels of terrain make this property attractive for many avenues of fun and adventure! Go fishing, ride your ATVs, build your dream home, you name it- AND you are located just minutes from the quaint village of Chester as well as Okemo Mountain. Access to the property is via a deeded 50' ROW.

Listed by Amy Bedor of Parkway Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

739 Gould Road Chester VT 05143

Chester, VT739 Gould Road

Price$235,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4927784

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 1

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.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 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

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 November 27, 2022 10:08 AM EST.