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84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermont’s Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Don’t miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.

5023272 MLS

84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermont’s Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Don’t miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.

000 Green Mountain Tpke, Chester

$229,000

27.8 +/- acre wooded parcel close to Chester Village with beautiful views. Driveway is roughed in and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Newly opened views from the plateau along the ridge accessed by an established logging road are a must see. Soil tests indicate a 3 bedroom home site is possible at the scenic viewpoint. Property has old stone walls and gorgeous rocks and stone on site for landscaping. Possible to subdivide. Adjoins town forest along the back property line. The 27.8 acres meets the minimum requirement for enrollment in the VT Current Use Forestry program for tax savings. Close to the charming village of Grafton for x-country skiing and dining at the historic Grafton Tavern. Okemo, Magic and Bromley Mountains are within easy reach. 15 min. to I91. Whether you are a summer recreational enthusiast, enjoy winter sports, or just want to chill in a small village atmosphere, this property is ready for your building plans!

5098347 MLS

27.8 +/- acre wooded parcel close to Chester Village with beautiful views. Driveway is roughed in and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Newly opened views from the plateau along the ridge accessed by an established logging road are a must see. Soil tests indicate a 3 bedroom home site is possible at the scenic viewpoint. Property has old stone walls and gorgeous rocks and stone on site for landscaping. Possible to subdivide. Adjoins town forest along the back property line. The 27.8 acres meets the minimum requirement for enrollment in the VT Current Use Forestry program for tax savings. Close to the charming village of Grafton for x-country skiing and dining at the historic Grafton Tavern. Okemo, Magic and Bromley Mountains are within easy reach. 15 min. to I91. Whether you are a summer recreational enthusiast, enjoy winter sports, or just want to chill in a small village atmosphere, this property is ready for your building plans!

00 Quarry Rd, Chester

$225,000

Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102142.

5102143 MLS

Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102142.

3781 Flamstead Rd, Chester

$225,000

Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102143.

3 Beds ⋅ 2 Baths ⋅ 5102142 MLS

Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102143.

3781 Flamstead Rd, Chester

$159,000

There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town maintained road is easy access and power near by. It is the perfect time to escape, start a new beginning, or just take a weekend to breathe. Please call GMP and communications for availability and cost.

5069927 MLS

There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town maintained road is easy access and power near by. It is the perfect time to escape, start a new beginning, or just take a weekend to breathe. Please call GMP and communications for availability and cost.

00 Contro Rd, Chester

$129,900

This cozy home presents so many opportunities-Live here, vacation here, rental property, renovate as you want and flip, ski home! Offering 2 bedrooms, 1 full bathroom, eat in kitchen/dining room, and living room. Outside is a great 1 car garage with plenty of space for all your tools, lawnmower, etc. Set right in the town of Chester in short walking distance to stores or the town green with wonderful coffee shops and other great shops! Close to ski areas, hospital, schools, and much more, whatever you are looking for this single floor home could check all your boxes! Or would make a great investment property with a little work! Call for your appointment today.

2 Beds ⋅ 1 Baths ⋅ 5114929 MLS

This cozy home presents so many opportunities-Live here, vacation here, rental property, renovate as you want and flip, ski home! Offering 2 bedrooms, 1 full bathroom, eat in kitchen/dining room, and living room. Outside is a great 1 car garage with plenty of space for all your tools, lawnmower, etc. Set right in the town of Chester in short walking distance to stores or the town green with wonderful coffee shops and other great shops! Close to ski areas, hospital, schools, and much more, whatever you are looking for this single floor home could check all your boxes! Or would make a great investment property with a little work! Call for your appointment today.

473 Elm St, Chester

$114,900

Bring Your Vision to Life in Beautiful Chester, Vermont! Discover the potential of this partially constructed A-frame home nestled on approximately 2 acres along VT Route 11 in scenic Chester, Vermont. Offering approximately 980 square feet of planned living space, this 3-bedroom, 2-bathroom property presents an exciting opportunity for investors, builders, contractors, or buyers looking to create a personalized Vermont retreat. The renovation is awaiting a complete build-out, including windows, doors, and all interior and exterior finish materials, allowing the next owner to take the project from its current stage to a finished home tailored to their vision. With its distinctive A-frame design and nearly 2 acres of land, the property offers a blank canvas for a weekend getaway, year-round residence, or investment opportunity. Enjoy the possibilities of owning a property in the charming town of Chester, surrounded by Vermont's natural beauty and four-season appeal. Bring your plans, creativity, and finishing expertise to transform this unfinished project into something special. Property is being sold in its current, unfinished condition. Buyers should perform their own due diligence regarding construction requirements, permits, utilities, and completion costs.

3 Beds ⋅ 2 Baths ⋅ 5114547 MLS

Bring Your Vision to Life in Beautiful Chester, Vermont! Discover the potential of this partially constructed A-frame home nestled on approximately 2 acres along VT Route 11 in scenic Chester, Vermont. Offering approximately 980 square feet of planned living space, this 3-bedroom, 2-bathroom property presents an exciting opportunity for investors, builders, contractors, or buyers looking to create a personalized Vermont retreat. The renovation is awaiting a complete build-out, including windows, doors, and all interior and exterior finish materials, allowing the next owner to take the project from its current stage to a finished home tailored to their vision. With its distinctive A-frame design and nearly 2 acres of land, the property offers a blank canvas for a weekend getaway, year-round residence, or investment opportunity. Enjoy the possibilities of owning a property in the charming town of Chester, surrounded by Vermont's natural beauty and four-season appeal. Bring your plans, creativity, and finishing expertise to transform this unfinished project into something special. Property is being sold in its current, unfinished condition. Buyers should perform their own due diligence regarding construction requirements, permits, utilities, and completion costs.

4351 Vermont Route 11 W, Chester

$105,000

As a neighbor, I can vouch for this location... Discover the perfect setting for your Vermont dream home on this beautiful 3+ acre parcel located along Route 103 in Chester. For 23 years I have driven by this lot on my way to Okemo... No traffic just a zen like 15 minute drive along the Williams River. A super convenient location with easy access to town amenities, shopping, dining, and nearby ski resorts, this property combines the charm of a country setting with year-round convenience. The gently sloping, partially wooded landscape features beautiful mature trees and classic New England stone walls, adding character and natural beauty to the property. Whether you envision a cozy country retreat or a full-time residence, this parcel offers an opportunity to create your own Vermont getaway in a desirable location close to outdoor recreation and all that the Okemo Valley has to offer. Visit the Okemo real estate community today. (survey and ww permit for a 3br septic available also abutting lot is also available for sale)

5114886 MLS

As a neighbor, I can vouch for this location... Discover the perfect setting for your Vermont dream home on this beautiful 3+ acre parcel located along Route 103 in Chester. For 23 years I have driven by this lot on my way to Okemo... No traffic just a zen like 15 minute drive along the Williams River. A super convenient location with easy access to town amenities, shopping, dining, and nearby ski resorts, this property combines the charm of a country setting with year-round convenience. The gently sloping, partially wooded landscape features beautiful mature trees and classic New England stone walls, adding character and natural beauty to the property. Whether you envision a cozy country retreat or a full-time residence, this parcel offers an opportunity to create your own Vermont getaway in a desirable location close to outdoor recreation and all that the Okemo Valley has to offer. Visit the Okemo real estate community today. (survey and ww permit for a 3br septic available also abutting lot is also available for sale)

Lot 4 Vt Route 103, Chester

$105,000

As a neighbor, I can vouch for this location... Discover the perfect setting for your Vermont dream home on this beautiful 3+ acre parcel located along Route 103 in Chester. For 23 years I have driven by this lot on my way to Okemo... No traffic just a zen like 15 minute drive along the Williams River. A super convenient location with easy access to town amenities, shopping, dining, and nearby ski resorts, this property combines the charm of a country setting with year-round convenience. The gently sloping, partially wooded landscape features beautiful mature trees and classic New England stone walls, adding character and natural beauty to the property. Whether you envision a cozy country retreat or a full-time residence, this parcel offers an opportunity to create your own Vermont getaway in a desirable location close to outdoor recreation and all that the Okemo Valley has to offer. Visit the Okemo real estate community today. (survey and ww permit for a 3br septic available also abutting lot is also available for sale)

5114885 MLS

As a neighbor, I can vouch for this location... Discover the perfect setting for your Vermont dream home on this beautiful 3+ acre parcel located along Route 103 in Chester. For 23 years I have driven by this lot on my way to Okemo... No traffic just a zen like 15 minute drive along the Williams River. A super convenient location with easy access to town amenities, shopping, dining, and nearby ski resorts, this property combines the charm of a country setting with year-round convenience. The gently sloping, partially wooded landscape features beautiful mature trees and classic New England stone walls, adding character and natural beauty to the property. Whether you envision a cozy country retreat or a full-time residence, this parcel offers an opportunity to create your own Vermont getaway in a desirable location close to outdoor recreation and all that the Okemo Valley has to offer. Visit the Okemo real estate community today. (survey and ww permit for a 3br septic available also abutting lot is also available for sale)

Lot 3 Vt Route 103, Chester

$100,000

Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are available at the street, adding convenience for development. A gravel driveway provides easy access from First Avenue, and a recent survey is available. An existing foundation remains on the property and may offer the potential to be repurposed for a garage, shed, or other accessory structure. Buyers should perform their own due diligence and consult with a qualified contractor regarding its condition and suitability, as no representations or guarantees are being made. Enjoy a convenient location just 0.6 miles from the Chester Farmers Market and The Common shopping plaza, where you'll find local shops and cafés. The nearest hospital is approximately 10 minutes away, and Boston MA is 2.5 hours away, making this an ideal location for a primary residence, vacation home, or investment opportunity. Whether you're looking to build now or invest for the future, this well-located lot combines accessibility, utilities, and small-town Vermont charm.

5100755 MLS

Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are available at the street, adding convenience for development. A gravel driveway provides easy access from First Avenue, and a recent survey is available. An existing foundation remains on the property and may offer the potential to be repurposed for a garage, shed, or other accessory structure. Buyers should perform their own due diligence and consult with a qualified contractor regarding its condition and suitability, as no representations or guarantees are being made. Enjoy a convenient location just 0.6 miles from the Chester Farmers Market and The Common shopping plaza, where you'll find local shops and cafés. The nearest hospital is approximately 10 minutes away, and Boston MA is 2.5 hours away, making this an ideal location for a primary residence, vacation home, or investment opportunity. Whether you're looking to build now or invest for the future, this well-located lot combines accessibility, utilities, and small-town Vermont charm.

427 Depot St, Chester

$87,500

CHESTER 10.4+/- acre parcel of land offers offers 180 degree ridgeline views with clearing from an elevated plateau for either a house site or a camp site with a home closer to the town maintained road. A nice stream meanders through the property which is dotted with large rocks and stone walls. There is 245 ft. of frontage on Snell Road and utility pole at the road. Close to Okemo and Magic Mountain, Chester Village.

5094246 MLS

CHESTER 10.4+/- acre parcel of land offers offers 180 degree ridgeline views with clearing from an elevated plateau for either a house site or a camp site with a home closer to the town maintained road. A nice stream meanders through the property which is dotted with large rocks and stone walls. There is 245 ft. of frontage on Snell Road and utility pole at the road. Close to Okemo and Magic Mountain, Chester Village.

00 Snell Rd, Chester

$79,000

Privacy doesn't have to mean isolation!! Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a primary residence or Vermont getaway without sacrificing proximity to local shops, restaurants, and community events. Power and fiber-optic internet are available, and a state-approved 4 Bedroom wastewater permit is already in place, helping streamline the path toward future development. The parcel also includes frontage along Route 35, providing an additional access option for future consideration. Ideally located for four-season recreation, the property is within easy driving distance of Okemo, Magic Mountain, Stratton, and Bromley ski areas, as well as hiking, biking, fishing, and countless outdoor adventures throughout Southern Vermont. Whether you're planning a year-round residence or a Vermont retreat, this property offers a rare combination of privacy, accessibility, and convenience in a sought-after Chester location.

5093908 MLS

Privacy doesn't have to mean isolation!! Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a primary residence or Vermont getaway without sacrificing proximity to local shops, restaurants, and community events. Power and fiber-optic internet are available, and a state-approved 4 Bedroom wastewater permit is already in place, helping streamline the path toward future development. The parcel also includes frontage along Route 35, providing an additional access option for future consideration. Ideally located for four-season recreation, the property is within easy driving distance of Okemo, Magic Mountain, Stratton, and Bromley ski areas, as well as hiking, biking, fishing, and countless outdoor adventures throughout Southern Vermont. Whether you're planning a year-round residence or a Vermont retreat, this property offers a rare combination of privacy, accessibility, and convenience in a sought-after Chester location.

Linden Way, Chester

$75,000

Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

2 Beds ⋅ 1 Baths ⋅ 5093286 MLS

Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

1144 Potash Brook Rd, Chester

$74,500

Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots, beautiful in every season! Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

5074848 MLS

Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots, beautiful in every season! Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

Tbd Farrar Rd, Chester

$74,000

Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

5061671 MLS

Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

00 Remington Rd, Chester

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