Chester VT Real Estate

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Chester, Vermont is a charming small town tucked away in the Green Mountains. From its quaint buildings to its tranquil rivers and lakes, this beautiful town has something for everyone. Spend an afternoon wandering through the picturesque downtown area and local businesses, take a peaceful stroll through the surrounding countryside, or simply sit back and marvel at the magnificent mountain views – no matter what you choose to do, Chester will offer an unparalleled experience!

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218 Gunderson Road Chester VT 05143

Chester, VT218 Gunderson Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 5005114

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing
  • Zip 05143

This quintessential 4BR/2.5 bath farmhouse, fully renovated and absolutely gorgeous, is perched on a grassy knoll overlooking 32 acres of rolling meadow, hardwood forest and private pond. (House has 5br State engineered septic system installed this July.) The modern touches that are essential for today's style of living pair perfectly with the warmth and charm of an old farmhouse. The house was renovated in 2017, including new roof, insulation, pine flooring as well as all plumbing, electrical and heating systems. The open kitchen/living area features a beautiful fieldstone fireplace and there's a main level family room with a side office. Upstairs are 4 bedrooms and 2 full bathrooms, including the principal bedroom with its en-suite bath. The large mudroom can handle all your clothes and gear. Sun or Shade? You have choices of two elevated stone patios to enjoy outdoor living in total privacy. The large majestic barn offers plenty of options for events or storage, so bring your dancing boots and have an old fashioned barn dance! The fields, pond and apple trees attract all sorts of wildlife and there couldn't be a more perfect hill for wintertime sledding, snow-shoeing or skating! The expansive fields are currently mowed by a local farmer in exchange for the hay, and Gunderson Road is maintained and plowed by the town. Located 5 minutes to the Chester green, 22 minutes to Okemo or Bromley ski areas, and only 13 minutes to Lowell Lake State Park.

Listed by Katherine Burns and Joseph Karl of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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Whitmore Brook Road Chester VT 05143

Chester, VTWhitmore Brook Road

Price$69,000

Est. Mortgage: $/month

MLS Number 5005113

  • Land
  • Acreage 13.69
  • PricePerSqFt 5040.18
  • Zoning Res

This four lot subdivision is a builders dream. The abutting house took two of the lots for a buffer. Two remaining subdivided lots come complete with state permits for waste water and septic designs. Come take a look and bring your plans. These lots average less than $35k per lot.

Listed by Frank Provance of Diamond Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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665 Route 10 Chester VT 05143

Chester, VT665 Route 10

Price$899,999

Est. Mortgage: $/month

MLS Number 5003697

  • Residential Single Family
  • Bedrooms 9
  • Bathroom 10
  • Construction Existing
  • Zip 05143

Discover a unique turnkey opportunity with this beautifully updated 1800's farmhouse, perfect for an inn, B&B, short-term rental or wedding venue. Recently renovated, the stunning home combines modern comforts with timeless charm, making it an ideal choice for both private and commercial ventures. As you enter, a grand staircase warmly welcomes you, leading to spacious interiors with original wide board floors. The property has been meticulously insulated and painted, giving it a fresh, contemporary feel. The serene landscape offers a perfect setting for a retreat, ski trip, or wedding. This property is offering 9 large bedrooms, most with ensuite bathrooms. The commercial kitchen, dining room, and separate owner's quarters enhance its functionality. Additionally, the Speak Easy, cozy library, and inviting sitting room offer numerous possibilities for creating a welcoming environment. Outside, the large 2000 sqft barn is ideal for a workshop, studio or event space. The property also features a large parking area, a tranquil pond, and open areas for tents to host weddings, all set on over 10 beautiful acres. The pond is surrounded by tranquil areas to sit and relax and nature watch. Whether you're looking to create a large family home, a thriving B&B, a ski club, or an artist retreat, this versatile property is just 10 minutes from Okemo Mountain and less than 10 minutes from the stunning Victorian village of Chester. Seize the day and invest in this Vermont heriloom home!

Listed by Daire Gibney and Eben Viens of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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160 Peck Road Chester VT 05143

Chester, VT160 Peck Road

Price$375,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5003646

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Nestled on a private lot just minutes from the heart of Chester Village, this delightful three-bedroom, two-bathroom Cape Cod-style home offers the perfect blend of tranquility and convenience. As you step inside, you'll be greeted by a great room flooded with natural light, featuring a vaulted ceiling and a cozy double-sided fireplace, ideal for Vermont's chilly evenings. The home's interior boasts elegant wood and slate floors that add a touch of rustic charm. This property is truly an entertainer's paradise with its heated inground pool and expansive stone patio, perfect for summer gatherings. Enjoy your morning coffee on the covered front porch, or unwind on the additional covered porch at the back of the house. Car enthusiasts and hobbyists will appreciate the detached garage, plus an additional garage under the home, both providing ample storage space. The large garage even includes extra storage space above. This home is in a prime location, close to schools, a variety of restaurants, and convenient shopping options. Adventure seekers will love the short drive to Okemo Mountain, offering year-round recreational activities. To top it all off, the home is equipped with a whole-house generator, ensuring peace of mind no matter the weather. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Katherine Burns and Sarah Sheehan of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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3483 Popple Dungeon Road Chester VT 05143

Chester, VT3483 Popple Dungeon Road

Price$285,000

Est. Mortgage: $/month

Pending

MLS Number 5003042

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 2
  • Construction Existing
  • Zip 05143

This well maintained home is located on a country road in Chester that meanders along a brook. One level living with high ceilings and tasteful upgrades throughout. A wood stove warms the living space in the cooler months. A wood shed and patio area located off the main living area, perfect to enjoy outdoor dining. A heated two car garage with a second floor that would be perfect to finish off for additional living space. A Tesla wall is rented so that the home stays functional during power outages. Beautiful stone walls and garden beds surround the exterior. A wood shed and patio area located off the main living area, perfect to enjoy outdoor dining.

Listed by Jessica Citera of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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810 Quarry Road Chester VT 05143

Chester, VT810 Quarry Road

Price$855,000

Est. Mortgage: $/month

MLS Number 5002963

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing
  • Zip 05143

The Grafton Village Inn was the inspiration for this truly remarkable custom built colonial home, perfectly sited on 77 private acres on the outskirts of quaint Chester, VT. High quality craftsmanship is on display throughout this lovely home. The blue stone mudroom floor leads you directly through the stone archway into a chef's kitchen with custom Vermont soapstone sink, countertops and island gas range. Dine more casually in the kitchen, or in the adjacent formal dining room. The main floor plan is complete with a large living room with beautiful built in cabinetry and a gorgeous wood burning fireplace. The elegant stairway beckons you to the second floor where you'll find two spacious bedrooms, as well as a lovely primary ensuite with a soaking tub, double vanity and a huge walk-in closet. Continue through the walk-in closet to the bonus room over the attached 2 car garage. Complete with it's own wood burning stove, this would make an ideal studio or home office. The top level, or attic is beautifully finished and would make a terrific playroom, or studio space. The full basement offers excellent storage space, and the surrounding landscape is an outdoorsman's delight with over 2 miles of marked trails ideal for hiking, running, snowshoeing, XC skiing, mountain biking or just wandering. 75 acres are enrolled in the land use program offering significant tax benefits. Great views in a tranquil, seemingly rural setting just outside of downtown.

Listed by Christopher Cummings of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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199 Maple Ridge Road Chester VT 05143

Chester, VT199 Maple Ridge Road

Price$350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5002751

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Located halfway between the towns of Chester and Springfield, this immaculate, vacant, and well cared for raised-ranch style home is ready for new owners to love it. You'll enjoy the TREX decks that look out onto a large, groomed lawn surrounded by mature trees which offer complete privacy! Enter from the front door or from the two-bay garage. Go up the stairs for one-story living, or down another set of stairs to find a spotless, spacious basement with a workshop room, a large room with a bar, and a utility room. Lower level is not finished, but there is plenty of opportunity to create more living space within the three rooms! Showing to prequalified buyers only.

Listed by Heather Gleim of CENTURY 21 MRC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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1328 Chandler Road Chester VT 05143

Chester, VT1328 Chandler Road

Price$2,345,000

Est. Mortgage: $/month

MLS Number 5002063

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing
  • Zip 05143

Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside a wide-open main living area and great room overlooks the 10 foot deep swimming pond, and the nearby stream can be heard from the deck or kitchen with the windows open. Step into the luxurious primary suite, a sanctuary with large windows and a spa inspired bath with a free-standing tub that boasts one of the best views from the house. Enjoy the newly renovated lower level with additional bedrooms and expansive family room. This area is ready for your touch and enjoys walkout access to the yard and pond. The 2nd level of the barn is currently a wood shop with wood-stove and a 2nd access from the road allows for storing large pieces or equipment on this upper level. The ground level of the barn has traditional sliding barn doors and extensive parking in front. Underground power and water lines travel from the house to a nearby site where another barn or horse arena could be built. A unique home treasure and like its organic architectural design the land has its own special quality of character and beauty. 193 acres are in the VT Land Use program. There is a 6 bedroom septic.

Listed by Suzanne Garvey and Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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Remington Road Chester VT 05143

Chester, VTRemington Road

Price$40,000

Est. Mortgage: $/month

MLS Number 5001944

  • Land
  • Acreage 5.51
  • Area Neighborhood
  • PricePerSqFt 7259.53
  • Zoning residential

One of the larger lots in the lower Remington subdivision. This private lot has underground power at the lot and the permitted septic is an inground system. Bring your plans and your builder or have the seller build your dream home! The seller is a Vermont licensed Realtor.

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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Remington Road Chester VT 05143

Chester, VTRemington Road

Price$125,000

Est. Mortgage: $/month

MLS Number 5001940

  • Land
  • Acreage 9.91
  • Area Neighborhood
  • PricePerSqFt 12613.52
  • Zoning residential

Just minutes from the Chester Green. The largest available lot in the subdivision with end of the road privacy. This almost 10 acre parcel will afford long distance mountain views with clearing. Underground power is at the lot and the permitted septic is an inground system. All of the heavy lifting is done. Bring your plans and your builder or have the seller build your dream home! The seller is a Vermont licensed Realtor.

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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2356 Lovers Lane Chester VT 05143

Chester, VT2356 Lovers Lane

Price$4,275,000

Est. Mortgage: $/month

MLS Number 5001473

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 6
  • Construction Existing
  • Zip 05143

In Southern Vermont's Green Mountains, Owl Hill Reserve is a sanctuary spanning 1,928 acres, an expanse over twice the size of New York City's Central Park. Assembled over half a century, this land has united generations in the celebration of the great outdoors. At the heart of the reserve stands an 1800s brick farmhouse, a testament to earlier days of farming, complemented by two historic barns, a two-bedroom barn apartment and guest house. Surrounding the farmstead are apple trees, stonewalls and a spring fed two-acre swimming pond, creating a quiet retreat or jubilant family gatherings. A 3.5-mile private, gravel road meanders with the brook, unwinding through a carefully managed northern hardwood forest, predominantly Sugar Maple, home to a rich ecosystem including bear, moose, coyote, bobcat, and deer. The changing landscape includes exceptional mountain views and rolling meadows either cut for hay or used for grazing cattle. The clear waters of the brook beckon fly fisherman to cast lines. Cross country skiing, snowshoeing, biking, hiking and equestrian pursuits are all out the backdoor with endless trails to explore. A remote cabin near an apple orchard offers a place to immerse in nature or a place to write. Owl Hill Reserve is a legacy offering. It offers the luxury of simplicity, the wealth of nature, and the bond of family heritage. Less than 3 miles from the village center and skiing nearby: 25 mins to Okemo, 33 mins to Bromley. 2.5 hrs to Boston, 4.5 hrs to NY.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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255 Linden Way Chester VT 05143

Chester, VT255 Linden Way

Price$129,000

Est. Mortgage: $/month

MLS Number 5001005

  • Land
  • Acreage 2.01
  • Area Rural
  • PricePerSqFt 64179.1
  • Zoning residential

A very rare find! Here is your chance to own 2+/- acres of beautiful "action ready" land in the town of Chester. Situated in a woodsy setting, your new home will feel intimate and private, yet only a 15 minute walk into the town of Chester. Best of all, the under ground electric, well, septic, cable and gravel pad are existing and ready to be built on! There is a flat upper pad for your home site with a flat lower grass backyard or walkout basement. In addition, enjoy the sound of the babbling brook that is set safely below the home site. This is truly a one of a kind opportunity for your dream home with all your utilities and pad ready to go! A huge money and time saver! This land is ideally located for skiing! Just 18 minutes to Okemo, 30 minutes to Bromley and 45 minutes to Stratton. Grafton is 10 minutes by car, I-91 is just 15 minutes, and Lebanon/Hanover NH is 1 hour. The road has been newly renamed so there is no sign post yet. Use the Directions provided here on MLS.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Jul 11, 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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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 July 18, 2024 5:24 PM EDT