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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.

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656 Main Street Chester VT 05143

Chester, VT656 Main Street

Price$649,000

Est. Mortgage: $/month

MLS Number 4998244

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

The Walter Austin House, a 3+ bedroom, 2.5 bath Queen Anne Victorian on .37 +/- acres in the Chester Village is a grand home that blends qualities from the Gilded Age with a more contemporary lifestyle. The first floor features a tiled mudroom, elegant foyer and spacious living room with an attractive marble gas fireplace. Original pocket doors open to the formal dining room. The efficient, classically styled kitchen has a breakfast bar, Corian countertops and accented glass-paned cabinets with a lovely picture window. The inviting Great Room has a cathedral ceiling, skylights and hardwood flooring with radiant heat and features a beautiful palladium-crowned triptych window overlooking the lovely pastoral view which delights in all seasons. The second floor features 3 bedrooms, a spacious bathroom with a clawfoot soaking tub and large tiled walk-in shower. The laundry room with half bath is across the hall and the finished third floor provides a quiet retreat with two finished rooms for office, study or guest overflow. The lovely, private grounds feature a deck with auto awning, a courtyard , a luxurious relaxing hot tub/swim spa, raised garden beds and established flower gardens. In addition to a one car garage, a two story post & beam barn provides additional garage and work space and a second floor rec room or office. Stroll to the Green or play Pickle Ball at the Rec area! Close to skiing, Summer theater, hiking and all the area has to offer. Showings begin on June 2nd.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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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4877 Vt Route 103 Chester VT 05143

Chester, VT4877 Vt Route 103

Price$648,888

Est. Mortgage: $/month

MLS Number 4986618

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Looking for the perfect ready to move in home in Vermont? Look no further than this French Provincial meets Vermont cabin centrally located in the quiet town of Chester, Vermont on Route 103. Within an hour drive to 5+ great ski mountains, within 10 minutes to Okemo mountain. House features so many great amenities and improvements--new black/grey roof just installed June 2024, new egress windows, beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes and state parks, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today! Added bonus is owner is willing to offer financing with 30% down payment to approved buyer.

Listed by Erin Kendall of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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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15 Depot Street Chester VT 05143

MLS Number 5005895

  • Commercial
  • Year Built 1880
  • Square Feet 4,493
  • PricePerSqFt 132.43

Come and invest in Main Street America with this exceptional village center location! Are you seeking a state-of-the-art building with excellent revenue opportunities? Look no further. This property has been meticulously updated from top to bottom, offering a prime investment opportunity. The first floor features an expansive open space, formerly an art and presentation gallery, equipped with a portable stage, media room, fully equipped kitchen, LED lighting, skylights, decorative walls, and black walnut flooring and currently rented as a wonderful Tea Shop. The second floor includes two fully renovated apartments: a one-bedroom and a two-bedroom, both generating approximately $2,800/month . The lower level is climate-controlled with artist stalls, providing additional storage options. Outside, you'll find a handicap ramp for accessibility and and ADA bathrooms; additionally, a large 1850 barn currently used for storage, adds unique character and potential for further utilization. This one-of-a-kind property is a must-see for investors looking to capitalize on a versatile and modern space with substantial income potential.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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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643 Route 103 South Chester VT 05143

MLS Number 5002938

  • Commercial
  • Year Built 1979
  • Square Feet 2,504
  • Acreage 175
  • PricePerSqFt 219.61

OPPORTUNITY KNOCKS! This full-scale restaurant is a deli and bakery with catering business with 20 years cliental of loyal patronage. This is a turn-key operation that comes fully equipped and has a beer & wine license for the restaurant and an outside under the tent. Sales includes real estate with 1.8 acres with frontage on Rte. 103 which is the second busiest tourist route in Vermont,

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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$495,000

Est. Mortgage: $/month

MLS Number 5012763

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

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. There are 2 separate buildings. One needs to be finished, main building 3 floor could be finished for more living space.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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$485,000

Est. Mortgage: $/month

MLS Number 4990677

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

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 2bedroom 1 bathroom which has recently been updated with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's 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: 6.2% last updated on Sep 12, 2024
* 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

MLS Number 5005505

  • Commercial
  • Year Built 1820
  • Square Feet 4,060
  • Acreage 0.25
  • PricePerSqFt 119.46

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 for more units. The first being the business store front with great road visibility and rustic features like the two sided fireplace chimney, the second is a space in the back which could easily be turned into a long term rental with a kitchen and separate bathroom, the third is a second floor 2bedroom 1 bathroom which has recently been updated and rented with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's location comes parking right on the Green and behind the building with an owned park area. Some recent updates are the back portion on the building has a new roof and $80,000.00 worth of solar was added to the whole building making the electric bill extremely low.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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

491 Farrar Road Chester VT 05143

Chester, VT491 Farrar Road

Price$459,000

Est. Mortgage: $/month

MLS Number 5000203

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Nestled on a serene, quiet town maintained dirt road, this spacious home offers the perfect blend of tranquility and comfort. As you approach, you'll be captivated by the stunning long-range views that greet you from the expansive deck, a haven for relaxation and outdoor enjoyment. The deck overlooks a picturesque pond, not on the property but offering a beautiful, calming view that enhances the natural charm of the setting all the same. Step inside to discover a thoughtfully designed interior where ample space meets cozy. The large, finished basement is a true bonus, featuring a cozy and convientent propane stove and serving as an ideal games room or entertainment space for family and friends. Featureing 4 large bedrooms, 3.5 bathrooms, with large primary ensuite, large living room with views and that all enticing party or craft space in the below. This is equally a perfect vacation retreat or spacious family home. Conveniently located close to the popular ski areas of Okemo, Stratton, and Magic this home is perfect for winter sports enthusiasts. Whether you're seeking a peaceful year-round residence or a seasonal getaway, this property promises a lifestyle of serene beauty and endless recreational opportunities. Welcome home to your personal oasis.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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

3057 Vt Route 11 East Chester VT 05143

Chester, VT3057 Vt Route 11 East

Price$444,000

Est. Mortgage: $/month

MLS Number 5005884

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

A cool Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary Saltbox has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high ceilings and huge amount of work space will be appreciated. Set back from the road with plenty of parking area, there is room to add more outbuildings for business needs. The efficient house features a cozy living room, first floor bedroom, full bath and kitchen/dining that opens to the back deck overlooking the private pond. The second floor has a large common area adjoined by two bedrooms and a half bath with laundry. The whole house generator and Fiber Optic internet service will keep your systems and business running during power outages. Commutable to the Upper Valley, convenient to Springfield, skiing, shopping, Chester Village and all the area has to offer.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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

134 Gold River Extension Chester VT 05143

MLS Number 4952929

  • Commercial
  • Square Feet 6,656
  • Acreage 2.49
  • PricePerSqFt 63.85

Rare opportunity with commercial/industrial zoning. 2.49 acres that is fully permitted. Property can be used as one business spot, or share the office building with another business. Currently there are 3 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, office, and rail siding; plus an additional 1500 sq ft storage building. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Video attached to the MLS.

Listed by Andy Paluch of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.2% last updated on Sep 12, 2024
* 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 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 13, 2024 4:23 AM EDT