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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595 Main Street Chester VT 05143

Chester, VT595 Main Street

Price$395,000

Est. Mortgage: $/month

MLS Number 4985576

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

Exciting Investment Opportunity! Discover this expansive 2-unit side-by-side duplex conveniently nestled on Main Street, yet cleverly set back for peaceful seclusion and views of the tranquil Williams River. Each generously sized unit spans 1,900 square feet and boasts three inviting bedrooms, each accompanied by its own ensuite bathroom-a luxurious touch ensuring comfort and privacy for all residents. Step inside to find spacious, light-filled interiors characterized by airy open floor plans, lofty ceilings, and rustic exposed beams, creating an atmosphere of warmth and charm. The heart of each unit features a well-appointed kitchen, perfect for entertaining, while convenient in-unit laundry facilities add an extra layer of convenience to daily living. Embrace the serene outdoors from the expansive decks, offering ample space for dining, relaxation, and enjoying the soothing sounds of the river. This property presents an excellent opportunity for savvy investors or homeowners seeking supplemental income. Consider residing in one unit while leasing the other-a smart financial move that could offset your mortgage and expenses. Location-wise, you'll find yourself ideally situated within easy reach of the vibrant town green, with local amenities and Okemo and Stratton Mountain just a short drive away, outdoor adventure and recreation are always within reach. While the units could benefit from some cosmetic updates they are structurally sound and poised for the next chapter.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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595 Main Street Chester VT 05143

Chester, VT595 Main Street

Price$395,000

Est. Mortgage: $/month

MLS Number 4985574

  • Multifamily
  • Units 2
  • Bathroom 3
  • Acreage 1.51
  • Square Feet 3,892

Exciting Investment Opportunity! Discover this expansive 2-unit side-by-side duplex conveniently nestled on Main Street, yet cleverly set back for peaceful seclusion and views of the tranquil Williams River. Each generously sized unit spans 1,900 square feet and boasts three inviting bedrooms, each accompanied by its own ensuite bathroom-a luxurious touch ensuring comfort and privacy for all residents. Step inside to find spacious, light-filled interiors characterized by airy open floor plans, lofty ceilings, and rustic exposed beams, creating an atmosphere of warmth and charm. The heart of each unit features a well-appointed kitchen, perfect for entertaining, while convenient in-unit laundry facilities add an extra layer of convenience to daily living. Embrace the serene outdoors from the expansive decks, offering ample space for dining, relaxation, and enjoying the soothing sounds of the river. This property presents an excellent opportunity for savvy investors or homeowners seeking supplemental income. Consider residing in one unit while leasing the other-a smart financial move that could offset your mortgage and expenses. Location-wise, you'll find yourself ideally situated within easy reach of the vibrant town green, with local amenities and Okemo and Stratton Mountain just a short drive away, outdoor adventure and recreation are always within reach. While the units could benefit from some cosmetic updates they are structurally sound and poised for the next chapter.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

233 Dodge Road Chester VT 05143

Chester, VT233 Dodge Road

Price$799,000

Est. Mortgage: $/month

MLS Number 4985500

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 4
  • Construction Existing
  • Zip 05143

Nestled on a picturesque 3.6-acre lot, this expansive Colonial home offers the epitome of Vermont living. Boasting 6 bedrooms, the residence exudes comfort and space. The heart of the home is the generous kitchen with an island, abundant counter space, and cabinets, all adorned with elegant granite countertops. Entertain in the large dining room or relax in the spacious living room that seamlessly flows to the front deck, bringing the outdoors in. An inviting sunroom opens to a very private back deck featuring a rejuvenating hot tub. The new walkout basement entrance leads to a convenient mudroom with ample ski storage, making winter adventures a breeze. The basement encompasses a recreational room with extra sleeping quarters and a delightful game room, offering endless entertainment options. An attached oversized garage provides convenience and additional storage. Beyond the main residence, a substantial barn accommodates equipment and toys, while an attached cottage offers the potential for restoration into a charming playhouse or office. This turnkey offering includes full furnishings, ensuring a seamless transition into your new abode. Secluded and serene, yet just a half mile from town, this property provides the perfect balance of tranquility and accessibility. Enjoy a short 15-minute drive to Okemo Mountain and easy access to other major resorts. Immerse yourself in the Vermont experience at its finest, embracing the beauty and charm this property has to offer.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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242 Mattson Road Chester VT 05143

Chester, VT242 Mattson Road

Price$225,000

Est. Mortgage: $/month

Pending

MLS Number 4984020

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

Built in 2004 sits this ranch style home situated on 2.3 acres. Features 3 bedrooms. 2 full baths, eat in kitchen , full basement, 2 car detached garage, back deck and a nice level yard!

Listed by Dick Thackston of R.H. Thackston & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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102 Church Street Chester VT 05143

Chester, VT102 Church Street

Price$449,000

Est. Mortgage: $/month

MLS Number 4983222

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Artfully renovated VT 1895 farmhouse located just a quick stroll away from the quaint and vibrant Chester Green. Generously appointed with 3+ bedrooms and 2 baths, this charming home has been elegantly refreshed and upgraded with a nod to contemporary and modern sensibilities while preserving the original character. A welcoming covered front porch is a great spot to relax three seasons. The open and inviting first floor living space includes large living/dining rooms and an upgraded kitchen with marble flooring and new appliances. A first floor bedroom area adjoins a large three-quarter tiled bath and also features a sunny reading nook. The second floor features two large bedrooms, a full, tiled bath with radiant heat in the floor and a spacious bedroom/study that could also be used as a primary bedroom. Established perennial gardens and stonework surround the house and a large side yard and rear patio provide ample room for outdoor enjoyment. Close to Okemo, Magic and Bromley Mountains and year-round recreation, shops, crafts, farmers markets, town recreation area and conveniences.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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3089 Vt Route 11 West Chester VT 05143

Chester, VT3089 Vt Route 11 West

Price$159,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4982791

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05143

Charming 1850's Cape in need of restoration. Due to a freeze up, most of the first floor has been taken down to the studs and is ready for renovation except for the living room which is still intact with fireplace. The second floor has 3 bedrooms and has been newly sheet rocked and primed. The second floor bath has been reconfigured to accommodate a 3/4 bath with tiled shower. The roof has been replaced on the main house and the first floor windows have been replaced. The attached carriage barn, with the original outhouse, would make a wonderful great room or studio. There is also a detached two car garage. Come and see if this renovation project is a good fit for you. Convenient to Magic, Bromley, Okemo and Stratton mountains.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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00 Quarry Road Chester VT 05143

Chester, VT00 Quarry Road

Price$249,000

Est. Mortgage: $/month

MLS Number 4982433

  • Land
  • Acreage 27.8
  • PricePerSqFt 8956.83
  • Zoning R40

Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel would qualify for the VT Current Use Program for timber management and tax savings. 1 acre (R-40) zoning and 1478' of frontage along Quarry Road makes further subdivision a possibility. Enjoy the year-round recreation the area offers. Close to Grafton for x-country skiing and mountain biking. Convenient to Magic, Okemo, Stratton and Bromley Mountains for downhill enthusiasts. Convenient to I-91, 3 hours to Boston and 4.5 hours to NYC.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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341 Whitmore Brook Road Chester VT 05149

Chester, VT341 Whitmore Brook Road

Price$645,000

Est. Mortgage: $/month

Open House

MLS Number 4981700

  • Residential Single Family
  • Next Open House: Sun 02/25 2:00 pm. to 4:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing

Living in a log home has a special kind of warmth and coziness that embodies the essence of the Vermont lifestyle. The stone fireplace, exposed beams and the textured logs contribute to a feeling of authentic connection to the outdoors. For the outdoor enthusiast, the house is less than 8 miles to Okemo Mountain, with close proximity to hiking, VAST trails, golfing and swimming. Located right off of 103, Whitmore is a steep but town maintained road that is incredibly secluded. If privacy is what you're searching for, look no further. Nestled in between the birch trees, 341 Whitmore presents a charming opportunity for those looking to invest in a property with major potential. The house itself needs TLC, but with some imagination and elbow grease, this could be a dream retreat. Picture transforming the expansive living space with an impressive stone fireplace to suit your vision. Cathedral ceilings create an open and airy atmosphere. Ideal for entertaining, a designated area features a bar and the potential to create an impressive gathering space. Seize the chance to add your personal touch to this property-a practical and inviting home with endless possibilities. Next to the house, there is a poured foundation approved for a barn. Complete the vision or let your imagination run wild . Escape the hustle of modern life and schedule a showing today. Your Vermont retreat is just a vision away.

Listed by Frank Provance and Dana Haley of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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50 Grafton Street Chester VT 05143

Chester, VT50 Grafton Street

Price$329,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4977939

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

Discover your new home in Chester, VT! This versatile property features 4 beds, 3 baths, a spacious garage, and an RV port, accommodating single or two-family living. The flexible layout includes the potential for an in-law suite, or rental unit, making it adaptable to your needs. Well-maintained, has modern updates, and is a family-friendly and practical space filled with possibilities. Life in Chester is both convenient and charming. Enjoy the village atmosphere within walking distance to the Victorian village boasting historic charm, quaint shops, and local eateries. Schools and churches are within walking distance, adding to the community feel. Explore the Vermont outdoors with scenic trails and fishing spots, creating a serene environment. Winter enthusiasts can delight in the proximity of Okemo and Magic Mountain ski resorts for endless snow-filled adventures. Quick access to both I91 and VT Route 11 makes this a wonderful access point to the entire state of Vermont. This property isn't just a house; it's an opportunity to craft your ideal Vermont lifestyle. Join the welcoming community and make this house your home. Chester, VT offers practical living, a genuine community, and endless possibilities. Your dream home awaits in the heart of Vermont!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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49 Putnam Hill Road Chester VT 05143

Chester, VT49 Putnam Hill Road

Price$399,000

Est. Mortgage: $/month

MLS Number 4973364

  • Land
  • Acreage 3.2
  • PricePerSqFt 124687.5
  • Zoning Res 20

The heavy lifting has been done on this 3.2 acre+/- parcel in the Putnam Hill neighborhood overlooking the village of Chester. A nicely sited driveway leads to the building site with foundation, framing, installed windows and solid wood doors and wide pine flooring on site for 2.5 levels of above ground living space. 200 Amp power is in place as well as a 5 bedroom septic system and drilled well/pressure tank. Designed for a total of 4,500 sf with 5 bedrooms and 4 baths plus a full 1800 sf walk out basement that could be finished as well. Owner built by experienced master tradesman. Views of the surrounding Green Mountains and within walking distance to Chester Village. No drive-bys please. Private driveway. Please note adjoining property also listed as mls # 4972814.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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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49 Putnam Hill Road Chester VT 05143

Chester, VT49 Putnam Hill Road

Price$399,000

Est. Mortgage: $/month

MLS Number 4972797

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 4
  • Construction New Construction
  • Zip 05143

Located in the neighborhood of Putnam Hill in Chester, this newly constructed dormered 2.5 story 5 bedroom, 4 bath home on 3.2+/- acres has been framed and is utility ready with septic, well, electric in place. The first floor space features a Great Room with 16' ceilings at its highest points, large kitchen with work area and plenty of cabinet space, a separate dining room for large gatherings, a formal living room and full bath which could also function as a first floor bedroom. The second floor is designed for 4 bedrooms and 2 full baths and the third floor has flex space with four large dormers and beautiful views. This thoughtfully designed home includes a walkout basement with 9' ceilings and intentional framing to include large windows. Solid wood doors are on site along with 10” wide plank pine flooring, furnace and misc. materials. This home was built by a Master tradesman with years of experience. The architectural framing is quite remarkable as is the desirable location of Chester VT with short drives to various ski mountains.

Listed by Geralyn Donohue of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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

Whitmore Brook Road Chester VT 05143

Chester, VTWhitmore Brook Road

Price$159,000

Est. Mortgage: $/month

MLS Number 4972447

  • Land
  • Acreage 18.54
  • PricePerSqFt 8576.05
  • Zoning Res

This four lot subdivision is a builders dream. Four subdivided lots with state permits for waste water and septic designs. Come take a look and bring your plans. These lots average less than $40k per lot.

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Feb 15, 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

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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 February 22, 2024 7:08 AM EST