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Chester VT Real Estate

Chester is located in Windham County. Browse available Chester VT real estate below. 

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308 Adams Road Chester VT 05143

Chester, VT308 Adams Road

Price$900,000

Est. Mortgage: $/month

MLS Number 4916627

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,192
  • Construction Existing

A chain of title for the property began in 1766 when the land was passed from Thomas Chandler to W. Smith. Over a couple of centuries the land was cleared and farmed, often passed down from family member to family member. In 2013, the current owners purchased the 57 acre farm and built a contemporary, energy-efficient, three bedroom house with long range views. The light-filled house has an open floor plan with cathedral ceilings and windows flanking the walls on all four sides. A spacious kitchen anchors the room on one end and a large stone fireplace on the opposite end; in between is dining and a great room gathering area. Downstairs are two additional bedrooms with a family area, woodstove and French doors to the outdoors. Below the house is the former chicken coop, a campy three-season cabin for spill over family visits. A path, lined by stone walls and once used for shepherding sheep and cows into upper pastures, marks the beginning of the trails, which run through the property and connect on to a network of private trails. Walnut and butternut trees edge the fields as well as wild apple and pear trees…we're told the apples make up into a delicious, richly flavored apple sauce. A large post and beam, c1800s barn, in need of work, sits across the road. A fenced in vegetable garden has an asparagus patch and perennial gardens surround the house. Showings begin 6/24/22

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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256 Depot Street Chester VT 05143

Chester, VT256 Depot Street

Price$249,000

Est. Mortgage: $/month

MLS Number 4916572

  • Residential Single Family
  • Bathroom 3
  • Square Feet 1,700
  • Construction Existing
  • Bedrooms 3

This lovely home could be used as a single family home with guest apartment or be used as a 2 bedroom 1 bath unit, 1 bedroom 1 bath unit and an efficiency apartment with a 3/4 bathroom. This well taken care of home was just freshly painted and is ready for a new owner! Located right in the heart of Chester surrounded by shops and restaurants as well as plenty of out door entertainment.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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191 Depot Street Chester VT 05143

Chester, VT191 Depot Street

Price$650,000

Est. Mortgage: $/month

MLS Number 4915868

  • Residential Single Family
  • Square Feet 2,664
  • Bathroom 4
  • Construction Existing
  • Bedrooms 5

Amare! This jewel of Queen Anne architecture adorns a hilltop overlooking the charming village of Chester, VT. The eclectic interior design will delight, surprise, and warm your heart. The 3 bedroom and 3 bath house with attached 2 bedroom/1 bath guest /in-law suite is well appointed to accommodate family and friends. In the main house one will find an open concept kitchen/dining/entertaining area. The kitchen is well designed and equipped with Heartland appliances and opens on one side to an enchanting dining area and on the other side to an entertaining area detailed with a handsome black marble fireplace. A classic covered porch is easy to access for outdoor dining and taking in the Vermont hillside and village life. Additional living space is found in two spacious living rooms and a cozy media room. The attached guest/in-law suite is complete with a fabulous kitchen/dining/living area and an upper-level bedroom with ensuite bath. The exterior is composed of three covered porches, a stone patio, and pergola all detailed with native perennials. A gorgeous 50 x 30 three story barn completes the quintessential Vermont landscape. Updated plumbing, electrical and heating include a Bosch boiler and Buderus panel radiators, and 200 amp electrical! Perfect as a primary or secondary vacation home with easy access to village life and multi-seasonal recreation at nearby Okemo, Stratton, Killington and Bromley resorts. Broker/Public Open House on Saturday June 18 from 1 to 4PM.

Listed by Mary Mayhew of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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418 First Avenue Chester VT 05143-8983

Chester, VT418 First Avenue

Price$249,000

Est. Mortgage: $/month

MLS Number 4915300

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,477

Classic Farmhouse with 4 Bedrooms, 2 baths. Currently zoned two family, it can easily return to its single-family origins. Open one door to live as a single family, or rent out the upstairs 2 bedroom apartment and enjoy the spacious first floor. Many classic features: large foyer, wrap around porch, original wood floors, 2 story bay window and large rooms. Improvements include replacement windows, recently replaced hot water heater, furnace, roof and a 'great' room with pellet stove added to the first floor. Full home energy audit/weatherization in 2018. Has a rural feel with yard and gardens, but located close to amenities right off Chester Depot and Route 103.

Listed by Brian Gehlich of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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1187 Potash Brook Road Chester VT 05143

Chester, VT1187 Potash Brook Road

Price$459,900

Est. Mortgage: $/month

MLS Number 4915330

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,264

This home has been completely refinished with fresh paint, both interior and exterior, new flooring, bathrooms, kitchens, a 200 amp electric panel and wiring, a Buderus boiler, insulation, decks, light fixtures and more! If you're looking for a turn-key home on a private road with plenty of land, look no further. Enter into a large open concept kitchen/dining/living room with a cozy fireplace. Upstairs you'll find 3 spacious bedrooms including a primary bedroom with shiny wood floors and a gorgeous ensuite bathroom with double sink. Upstairs you'll also find an office, laundry room and another full bath and an additional 3/4 bath. Plus a loft!! A very sturdy ladder brings you to a great reading nook or possibly a child's dream bedroom, with plush new wall-to-wall carpeting. Back downstairs, off the living room is a beautiful refinished in-law suite! This features a galley kitchen with butcher block counters, rustic white wooden backsplash and an eat-in bar. There are two bedrooms or offices in the suite as well as a full bathroom and expansive living room. In addition to all this, there are two walk out basements with big enough doors to drive your lawn mower or possibly something larger into. All this on almost 12 acres of sloping lawn and garden space surrounded by the privacy of the woods. Come see if this is the dream house for you!

Listed by Chelsea Cary of Barrett & Valley Associates,Inc/Sprin

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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418 First Avenue Chester VT 05143-8983

Chester, VT418 First Avenue

Price$249,000

Est. Mortgage: $/month

MLS Number 4917491

  • Multifamily
  • Square Feet 2,477
  • Units 2
  • Bathroom 2
  • Acreage 0.67

Classic Farmhouse with 4 Bedrooms, 2 Baths. Each floor has separate 2 Bedroom, one bath apartment. Zoned two family, it can easily return to it's single-family origins. Open one door to live as a single family, or rent out the upstairs 2 bedroom apartment and enjoy the spacious first floor. Many classic features: large foyer, wrap around porch, original wood floors, 2 story bay window and large rooms. Needs updating. Improvements include replacement windows, recently replaced hot water heaters, furnace and roof. Full home energy audit/weatherization in 2018. Has a rural feel with yard and gardens, but located close to amenities right off Chester Depot and Route 103.

Listed by Brian Gehlich of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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289 Fletcher Hill Chester VT 05143

Chester, VT289 Fletcher Hill

Price$375,000

Est. Mortgage: $/month

MLS Number 4914836

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,848

This beautifully crafted salt- box style home features high ceilings, 3 large bedrooms, 2 bathrooms, spacious living room with Vermont casting stove, all located in a private rural neighborhood making this a great fulltime home or vacation retreat. Close to the welcoming village of Chester and 20 minutes to Okemo Mountain this is ideally situated close to I91 giving you easy access to all Vermont has to offer. Standing seam metal roof, large 2 car garage with direct entry via the newly added breezeway will make for easy living in the winter months. And the private deck off the kitchen is great for cooling off on a hot summer day. Open house is scheduled for Sunday June 12th from Noon to 3PM. Come see this beautiful home.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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529 Nudist Camp Road Chester VT 05143

Chester, VT529 Nudist Camp Road

Price$495,000

Est. Mortgage: $/month

MLS Number 4912532

  • Residential Single Family
  • Square Feet 1,665
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Now's your chance to finally own an immaculate log cabin in Vermont. Meticulously built and maintained, the owners are heartbroken to let this house go. Nestled on 5+ acres the home has a full covered front porch for enjoying evenings outdoors. Open concept living room/kitchen with vaulted ceilings are accented by a brick floor to ceiling chimney and a soapstone woodstove. There is a matching separate 2 car garage for cars with loft area for toys. Large deciduous trees shade the property perfect for a hammock. Nudist Camp road is a quiet dead end road with little traffic. Williams River State Forest abuts this property offering wonderful opportunities for snowshoeing, hiking and wildlife viewing. Sellers are installing a brand new efficient hot air furnace and water heater. Taxes are based on current town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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835 Quarry Road Chester VT 05143

Chester, VT835 Quarry Road

Price$675,000

Est. Mortgage: $/month

Pending

MLS Number 4908734

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,221
  • Construction Existing

If you are searching for the perfect Vermont setting for year round living and enjoyment look no further than "Hidden Meadow". Situated on a very private 23.52 acres you will find a home and property that has been lovingly cared for by its original owners. The house features a tile entry way that leads to a comfortable living room with vaulted ceilings, hardwood floors and a custom built modified Rumford Fireplace that will heat the room on those winter nights. The living room leads out to a screened in porch were you can relax, bird watch and look out over one of the most beautiful properties you will ever see. The rest of the main floor boasts an open kitchen with an island, ample counter and cabinet space, a formal dining room, 3 large bedrooms including a Master with private bath and a laundry room. The second floor space can used as a bedroom or a great home office with fiber optic internet. 2 car attached garage with heated workshop and a full basement offers a tremendous amount of storage. The property is special with a wealth of perennial gardens, mature abundantly producing blueberry bushes, lupine fields, custom stonework and steps. The large pond is 20 ft deep suitable for swimming and home to 100's of rainbow trout. The barn is suitable for animals with plenty of open pasture. The location is ideal, just 1 mile to the historic Chester Green and only minutes to the picturesque town of Grafton. Skiing and outdoor activities are also just minutes away.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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374 Richardson Road Chester VT 05143

Chester, VT374 Richardson Road

Price$699,000

Est. Mortgage: $/month

MLS Number 4908861

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,776
  • Bathroom 2
  • Bedrooms 3

Gracefully settled between the villages of Chester and Londonderry, sits a Vermont Farmhouse at road's end, sited on eleven+ acres of wood'n meadow. Dotted with old stone walls, a wildlife pond and enchanting views. The setting is magical. A wide country porch invites rocking chairs and visitors while the screened area encourages outdoor entertaining much of the year. The vintage flavor is apparent throughout the home- opening panel doors with antique latches or stepping foot on wide wood floors milled from indigenous trees from decades ago. This location is central to recreating: ski, hike, snowmobile, swim, or enjoy our local restaurants, theater and shopping. A center island kitchen with breakfast nook overlooks the rolling meadows and glass doors allows life to spill over onto the porch, deck or firepit area. A traditional dining room, adjacent to the intimate living room, awaits memorable dinner parties. The great room's remarkable soaring ceiling creates a central gathering spot and includes a cast iron wood burning stove to warm by when winter is settling in and snow abounds . The main floor bedroom would also make a delightful home office overlooking the fields to the rear. Upstairs you'll find additional bedrooms including a large “beamed ceiling” primary and a fun multi-functional den/game room. Two sets of farmhouse stairs give easy access. If quiet and open and vintage is your desire..Look no further. Showings begin Thursday, May 12th. Owner is a licensed Realtor.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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17 Grafton Street Chester VT 05143

Chester, VT17 Grafton Street

Price$325,000

Est. Mortgage: $/month

MLS Number 4895672

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,824

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: 5.81% last updated on Jun 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.

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17 Grafton Street Chester VT 05143

Chester, VT17 Grafton Street

Price$325,000

Est. Mortgage: $/month

MLS Number 4894930

  • Multifamily
  • Square Feet 1,824
  • Units 2
  • Acreage 0.37
  • Area In Town

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.

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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

316 Depot Street Chester VT 05143

Chester, VT316 Depot Street

Price$170,000

Est. Mortgage: $/month

MLS Number 4871589

  • Multifamily
  • Square Feet 2,135
  • Units 4
  • Acreage 0.5

Chester Vermont multi family , excellent rental history. Conveniently located in town. 4 units plus a garage barn space.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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.

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1377 VTRT 103 Chester VT 05143

Chester, VT1377 VTRT 103

Price$400,000

Est. Mortgage: $/month

MLS Number 4871606

  • Multifamily
  • Square Feet 2,280
  • Units 2
  • Bathroom 2
  • 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: 5.81% last updated on Jun 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.

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2220 Vt Route 103 South Chester VT 05143

Chester, VT2220 Vt Route 103 South

Price$147,900

Est. Mortgage: $/month

Pending

MLS Number 4766090

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 2,688

Great opportunity, with a commercial first floor and a residential upper level unit. Located just outside of Chester and 15 minutes away from Bellows Falls with great sign and advertisement capabilities. A new septic was just installed. Property is primed and ready to be finished by a new owner.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 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

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Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 June 26, 2022.