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Chester Vermont Real Estate For Sale

Welcome to ChesterVermontRealEstate.com, a Vermont Country Properties Sotheby's International Realty website, offering fine homes, condominiums, townhouses, land parcels, and commercial real estate properties in the Chester, Vermont area.
 
The mission of Vermont Country Properties Sotheby's International Realty is simple: to provide buyers and sellers with the most professional real estate services available, delivered by a staff of over 50 brokers and sales associates who are experienced, reputable, and knowledgeable. We commit to the highest level of professional conduct and representation. Our marketing platform is constantly evolving and is the most comprehensive in all of Vermont, utilizing extensive web based promotion and broad based print advertising.
 
Browse our exclusive listings below or use the search navigation at the left to refine your search and access all property listings in the Chester, Vermont area. You can also subscribe to our eListings newsletter to receive new properties that match your search in your email inbox as they are listed.
 
 

 

Exclusive Listings for ChesterVermontRealEstate.com

     Cavendish Gulf Road   ·  Cavendish, VT  
View Property Listing for Cavendish Gulf Road - Residential - Cavendish, Vermont (VT) Grand Federal Brick Colonial on 119 acres wonderfully restored in 2000. Architecturally designed renovations include new kitchen, foundation, spacious mudroom, 3-car garage, driveway & mahogany deck. Antique amenities offer living room with Rumford fireplace,...
Type: Residential
Price: $649,000
Acres: 119.0 Bedrooms: 4
Baths: 3
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     Grist Mill House Historic Gem   ·  Chester/Andover, VT  
View Property Listing for Grist Mill House Historic Gem - Commercial - Chester/Andover, Vermont (VT) This dramatic Grist Mill House is an extraordinary property located in the charming town of Chester, Vermont. This very distinctive home offers a private master suite with bath and vaulted ceilings. The spacious and warm kitchen is perfect for the gourmet...
Type: Commercial
Price: $599,000
Acres: 0.2
Square Feet: 5056
Bedrooms: 4
Baths: 2 Full, 1 Half
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     Grist Mill House Historic Gem   ·  Chester/Andover, VT  
View Property Listing for Grist Mill House Historic Gem - Residential - Chester/Andover, Vermont (VT) This dramatic Grist Mill House is an extraordinary property located in the charming town of Chester, Vermont. This very distinctive home offers a private master suite with bath and vaulted ceilings. The spacious and warm kitchen is perfect for the gourmet...
Type: Residential
Price: $599,000
Acres: 0.2
Square Feet: 5056
Bedrooms: 4
Baths: 2 Full, 1 Half
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     Birch Meadow, Middletown Road   ·  Chester/Andover, VT  
View Property Listing for Birch Meadow, Middletown Road - Residential - Chester/Andover, Vermont (VT) This home is filled with light, sits high on a beautiful lot & its location is on a wonderful road between Weston, Stratton & Okemo. Designed & built by Michael Hughes, this home offers light-filled spaces, soaring stone fireplace, fabulous mudroom entry,...
Type: Residential
Price: $539,000
Acres: 7.0
Square Feet: 3175
Bedrooms: 3
Baths: 2 Full, 1 Half
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     Popple Dungeon Rd   ·  Chester/Andover, VT  
View Property Listing for Popple Dungeon Rd  - Residential - Chester/Andover, Vermont (VT) Spacious home overlooking the 3rd green at Tater Hill Country Club. CYR Homes built this custom four bedroom, four bath home in 2004. Enjoy the wide open floor plan, stone fireplace and ground floor master bedroom and bath with its own fireplace. Take advantage...
Type: Residential
Price: $519,000
Acres: 3.7
Square Feet: 3176
Bedrooms: 4
Baths: 3 Full, 1 Half
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     137 Main Street, Chester   ·  Chester/Andover, VT  
View Property Listing for 137 Main Street, Chester - Residential - Chester/Andover, Vermont (VT) Magnificent Village Victorian home. Beautifully updated with today's amenities, yet still retains all the charm and character of its heritage. Incredible gourmet kitchen with original soap stone sink and walk in butler’s pantry. Walk to the quintessential...
Type: Residential
Price: $499,000
Acres: 0.3
Square Feet: 3736
Bedrooms: 5
Baths: 2 Full, 1 Half
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     354 Grout Road, Weathersfield (Pending)   ·  Weathersfield/Perkinsville/Greenbush, VT  
View Property Listing for 354 Grout Road, Weathersfield (Pending) - Residential - Weathersfield/Perkinsville/Greenbush, Vermont (VT) Exquisitely renovated custom post & beam home located on a 6+ acre lot. 2,900 SF on 3 floors with workshop & attached 1-car garage, 3 master bedrooms each with full bath (1 on each floor). Living rm with Rumford-style granite fireplace and cathedral ceiling....
Type: Residential
Price: $450,000
Acres: 6.3 Bedrooms: 3
Baths: 3
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     146 North Street, Chester   ·  Chester/Andover, VT  
View Property Listing for 146 North Street, Chester - Residential - Chester/Andover, Vermont (VT) Historic Chester Stone Village property offering unique craftsmanship and old world charm you would expect from a period home. Wide pine floors, rumford fireplaces, detailed moldings, paneled wainscot windows and beamed ceilings are just a few features of...
Type: Residential
Price: $399,900
Acres: 11.0
Square Feet: 2900
Bedrooms: 4
Baths: 2
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     High Street   ·  Chester/Andover, VT  
View Property Listing for High Street - Residential - Chester/Andover, Vermont (VT) Impeccable 1840 historic property located on nearly 4 pastoral acres with peaceful Williams River frontage. Tastefully restored and updated, the "Old Parsonage" offers charming details and a walk to town location over classic swinging bridge and private backyard....
Type: Residential
Price: $360,000
Acres: 3.9
Square Feet: 2200
Bedrooms: 3
Baths: 1 Full, 1 Half
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     Andover Ridge Road, Andover   ·  Chester/Andover, VT  
View Property Listing for Andover Ridge Road, Andover - Residential - Chester/Andover, Vermont (VT) Enjoy sunrise and sunset from this wonderful location on Andover Ridge! Comfortable first floor features oak flooring, kitchen with breakfast bar, open living room with wood stove, half bath with custom cabinetry and newly finished three-season room to take...
Type: Residential
Price: $349,000
Acres: 4.3
Square Feet: 1800
Bedrooms: 3
Baths: 2 Full, 1 Half
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     859 Hitchcock Hill Road, Windham   ·  Chester/Andover, VT  
View Property Listing for 859 Hitchcock Hill Road, Windham - Residential - Chester/Andover, Vermont (VT) Magnificent Montana Log home sited on 10+/- private acres. Beautiful gourmet kitchen with granite countertops and stainless steel appliances. Two car timber peg garage with overhang for all your extra toys. Located on the VAST snowmobile trail and just minutes...
Type: Residential
Price: $339,000
Acres: 10.6 Bedrooms: 3
Baths: 2
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     977 White Road   ·  Chester/Andover, VT  
View Property Listing for 977 White Road  - Residential - Chester/Andover, Vermont (VT) Classic Vermont cape featuring renovated country kitchen, first floor master bedroom & French doors to deck, pegged oak, pine floors and exposed beams. A generous screened porch provides the perfect summer spot for taking in spectacular western sunsets. The...
Type: Residential
Price: $310,000
Acres: 3.0
Square Feet: 2200
Bedrooms: 3
Baths: 2
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     Chester Gambrel Log Home   ·  Chester/Andover, VT  
View Property Listing for Chester Gambrel Log Home - Residential - Chester/Andover, Vermont (VT) This spacious and well maintained 4-bedroom (+loft)log home features a wonderfully landscaped yard and meadering stream for summer enjoyment. Interior wood beams, several French doors and slated wood stove area in the great room provide for indoor winter comfort...
Type: Residential
Price: $300,000
Acres: 1.5
Square Feet: 2974
Bedrooms: 4
Baths: 3
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     17 River Street, Chester   ·  Chester/Andover, VT  
View Property Listing for 17 River Street, Chester - Residential - Chester/Andover, Vermont (VT) Stunning 4 bdrm 2 bath magnificent home located in the quaint town of Chester Vermont. This wonderful spacious Cape Cod boasts a bright and airy floor plan with beautiful grounds for your enjoyment. Ceramic tile and hardwood flooring add quality and charm...
Type: Residential
Price: $299,000
Acres: 1.1
Square Feet: 2100
Bedrooms: 4
Baths: 2
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     37 Acres with Dramatic Views   ·  Chester/Andover, VT  
View Property Listing for 37 Acres with Dramatic Views - Land - Chester/Andover, Vermont (VT) Substantial acreage with outstanding views located on Marsh Hill Road in Andover just over the Weston town line. Preliminary engineering supports a 6 bedroom mound system. This desirable building lot offers mature hardwoods, dramatic views of Magic and Bromley...
Type: Land
Price: $295,000
Acres: 37.0
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     Crown Point Road, Cavendish lot H   ·  Cavendish, VT  
View Property Listing for Crown Point Road, Cavendish lot H - Land - Cavendish, Vermont (VT) Quiet and private location in the country. Small subdivision with easterly views to Mount Ascutney. Wonderful location to build a home with easy access to area amenities including snowmobiling trails, skiing, nearby lakes and golf. Restrictive covenants protect...
Type: Land
Price: $245,000
Acres: 1.0
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     Crown Point Road, Cavendish lot G   ·  Cavendish, VT  
View Property Listing for Crown Point Road, Cavendish lot G - Land - Cavendish, Vermont (VT) Quiet and private location in the country. Small subdivision with easterly views to Mount Ascutney. Wonderful location to build a home with easy access to area amenities including snowmobiling trails, skiing, nearby lakes and golf. Restrictive covenants protect...
Type: Land
Price: $235,000
Acres: 1.0
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     Crown Point Road, Cavendish lot D   ·  Cavendish, VT  
View Property Listing for Crown Point Road, Cavendish lot D - Land - Cavendish, Vermont (VT) Quiet and private location in the country. Small subdivision with easterly views to Mount Ascutney. Wonderful location to build a home with easy access to area amenities including snowmobiling trails, skiing, nearby lakes and golf. Restrictive covenants protect...
Type: Land
Price: $235,000
Acres: 1.0
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     Crown Point Road, Cavendish lot B   ·  Cavendish, VT  
View Property Listing for Crown Point Road, Cavendish lot B - Land - Cavendish, Vermont (VT) Quiet and private location in the country. Small subdivision with easterly views to Mount Ascutney. Wonderful location to build a home with easy access to area amenities including snowmobiling trails, skiing, nearby lakes and golf. Restrictive covenants protect...
Type: Land
Price: $235,000
Acres: 1.0
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     Crown Point Road, Cavendish lot A   ·  Cavendish, VT  
View Property Listing for Crown Point Road, Cavendish lot A - Land - Cavendish, Vermont (VT) Quiet and private location in the country. Small subdivision with easterly views to Mount Ascutney. Wonderful location to build a home with easy access to area amenities including snowmobiling trails, skiing, nearby lakes and golf. Restrictive covenants protect...
Type: Land
Price: $235,000
Acres: 1.0
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     Brookside Drive Lot 10c, Chester   ·  Chester/Andover, VT  
View Property Listing for Brookside Drive Lot 10c, Chester - Land - Chester/Andover, Vermont (VT) This 5.91 acre parcel has the most amazing long range views with its own private pond with stone steps. The sweeping driveway amidst stone walls leads you up to the magnificent building site. Very quiet and peaceful setting yet minutes to the quaint town of...
Type: Land
Price: $225,000
Acres: 5.9
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     Federal Building with Living Quarters   ·  Chester/Andover, VT  
View Property Listing for Federal Building with Living Quarters - Commercial - Chester/Andover, Vermont (VT) This village home is located in a central location to the quaint town of Chester. Previously used as an office building, this distinguished Federal home would be perfect for a residence with a home occupation. It boasts antique floors, charming exposed brick...
Type: Commercial
Price: $219,000
Acres: 1.0 Bedrooms: 2
Baths: 1
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     1830's Federal Home with space for home business   ·  Chester/Andover, VT  
View Property Listing for 1830's Federal Home with space for home business - Residential - Chester/Andover, Vermont (VT) This village home is located in a central location to the quaint town of Chester. Previously used as an office building, this distinguished Federal home would be perfect for a residence with a home occupation. It boasts antique floors, charming exposed brick...
Type: Residential
Price: $219,000
Acres: 0.3
Square Feet: 1900
Bedrooms: 2
Baths: 1 Full, 1 Half
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     Scott Pet Road   ·  Chester/Andover, VT  
View Property Listing for Scott Pet Road - Residential - Chester/Andover, Vermont (VT) Private location with 9 acres of hiking trails, pond and stream come with this cute two bedroom Ranch style home. Recreational activities are within easy access.
Type: Residential
Price: $159,000
Acres: 9.0
Square Feet: 1068
Bedrooms: 2
Baths: 1 Full, 1 Half
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     Running Road   ·  Chester/Andover, VT  
View Property Listing for Running Road - Land - Chester/Andover, Vermont (VT) Fabulous price on this pretty parcel. Privacy (own your own road) yet close to Okemo and Weston. Build your dream home and have the best of both worlds. Beautiful southern views, babbling brook and old stone walls. Permitted for three bedroom home. Hike the...
Type: Land
Price: $99,999
Acres: 1.0
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     Weston Andover Road Parcel   ·  Chester/Andover, VT  
View Property Listing for Weston Andover Road Parcel - Land - Chester/Andover, Vermont (VT) Delightful lot that has been mostly cleared. Winter and summer views. Access from paved road. Options for bldg site. Stone walls at edge of meadow and in rear of property near northern boundary. Build your dream home and be close to quintessential Vermont...
Type: Land
Price: $89,500
Acres: 6.3
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     Crown Point Road, Cavendish lot E   ·  Cavendish, VT  
View Property Listing for Crown Point Road, Cavendish lot E - Land - Cavendish, Vermont (VT) Quiet and private location in the country. Small subdivision with easterly views to Mount Ascutney. Wonderful location to build a home with easy access to area amenities including snowmobiling trails, skiing, nearby lakes and golf. Restrictive covenants protect...
Type: Land
Price: $79,000
Acres: 1.0
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Stowe
Stowe, Vermont
802.253.7267
Sugarbush
Stowe, Vermont
802.496.6000
Stratton
Bondville, Vermont
802.297.1100
Okemo
Ludlow, Vermont
802.228.4537
Manchester
Manchester, Vermont
802.362.5040
Shelburne
Shelburne, Vermont
802.985.8566
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