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Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add to the convenience. The second floor has two more generously sized bedrooms. Additionally, there is an incredible amount of storage in the barn. All this, within walking distance to shopping, restaurants, town hall, and all of the basics you might need in the quintessential town of Chester, Vermont! This house is anxiously awaiting it's next lucky owner.

3 Beds ⋅ 2 Baths ⋅ 5104543 MLS

Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add to the convenience. The second floor has two more generously sized bedrooms. Additionally, there is an incredible amount of storage in the barn. All this, within walking distance to shopping, restaurants, town hall, and all of the basics you might need in the quintessential town of Chester, Vermont! This house is anxiously awaiting it's next lucky owner.

447 Elm St, Chester

$250,000

There’s something quietly reassuring about a home that’s stood the test of time—and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits today’s lifestyle. Built circa 1945, the home offers three comfortable bedrooms—including a convenient ground-floor bedroom—and 1.5 baths, giving you flexibility for guests or single-level living. The layout is practical and easy to live in, and the enclosed rear entry porch adds everyday function—perfect for muddy boots, groceries, or easing into the house after a long Vermont day. Out back, the porch doubles as a relaxed hangout space, or step out onto the sun-filled deck for a bit more light and fresh air. It’s an easy, inviting setup for morning coffee or winding down at the end of the day. Downstairs, a full basement provides solid storage or workspace potential, while the detached two-car garage—with workshop space and automatic openers—offers flexibility for projects, hobbies, or extra gear. The paved driveway, standing seam metal roof, and straightforward systems like the oil-fired hot water setup all point toward low-maintenance ownership—something buyers appreciate more and more. The home is being offered with key appliances already in place, including an electric range, refrigerator, microwave, washer, dryer, and dehumidifier, making for an easy transition whether you’re just starting out or simplifying your next chapter. Set in one of Southern Vermont’s most loved villages, this is the kind of property that works just as well as a first home as it does for downsizing. Simple, solid, and well-located—if Chester’s been on your radar, this one’s worth a closer look before it slips by.

3 Beds ⋅ 2 Baths ⋅ 5088678 MLS

There’s something quietly reassuring about a home that’s stood the test of time—and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits today’s lifestyle. Built circa 1945, the home offers three comfortable bedrooms—including a convenient ground-floor bedroom—and 1.5 baths, giving you flexibility for guests or single-level living. The layout is practical and easy to live in, and the enclosed rear entry porch adds everyday function—perfect for muddy boots, groceries, or easing into the house after a long Vermont day. Out back, the porch doubles as a relaxed hangout space, or step out onto the sun-filled deck for a bit more light and fresh air. It’s an easy, inviting setup for morning coffee or winding down at the end of the day. Downstairs, a full basement provides solid storage or workspace potential, while the detached two-car garage—with workshop space and automatic openers—offers flexibility for projects, hobbies, or extra gear. The paved driveway, standing seam metal roof, and straightforward systems like the oil-fired hot water setup all point toward low-maintenance ownership—something buyers appreciate more and more. The home is being offered with key appliances already in place, including an electric range, refrigerator, microwave, washer, dryer, and dehumidifier, making for an easy transition whether you’re just starting out or simplifying your next chapter. Set in one of Southern Vermont’s most loved villages, this is the kind of property that works just as well as a first home as it does for downsizing. Simple, solid, and well-located—if Chester’s been on your radar, this one’s worth a closer look before it slips by.

202 Mountain Vw, Chester

$240,000

Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below, perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there’s room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery—rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont’s natural beauty. A property that offers privacy, water frontage, land, and mountain access—without giving up convenience.

3 Beds ⋅ 2 Baths ⋅ 5073930 MLS

Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below, perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there’s room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery—rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont’s natural beauty. A property that offers privacy, water frontage, land, and mountain access—without giving up convenience.

1397 Popple Dungeon Rd, Chester

$239,000

Not your cookie cutter home, this charming 2 BR home is located on the outskirts of Chester. One floor living for those wanting an easy keeper and carefree living. Hardwood floors throughout, large living room, formal dining room, galley kitchen and 2 roomy bedrooms. And let's not forget the spacious breezeway/entry. This area is perfect for hosting a gathering of friends and neighbors under shade or away from summer rains. Current owners have spent three years developing extensive perennial beds ensuring that there is always a flower in bloom. Along with perennials, owners have added lots of specialty trees-hardwood and fruit trees and bushes along with raised and in-ground beds and a new garden shed to store your tools. All this and there is still lawn to play on.

2 Beds ⋅ 1 Baths ⋅ 5086079 MLS

Not your cookie cutter home, this charming 2 BR home is located on the outskirts of Chester. One floor living for those wanting an easy keeper and carefree living. Hardwood floors throughout, large living room, formal dining room, galley kitchen and 2 roomy bedrooms. And let's not forget the spacious breezeway/entry. This area is perfect for hosting a gathering of friends and neighbors under shade or away from summer rains. Current owners have spent three years developing extensive perennial beds ensuring that there is always a flower in bloom. Along with perennials, owners have added lots of specialty trees-hardwood and fruit trees and bushes along with raised and in-ground beds and a new garden shed to store your tools. All this and there is still lawn to play on.

15 Breezy Ln, Chester

$210,000

Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

3 Beds ⋅ 1 Baths ⋅ 5048752 MLS

Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

419 Coach Rd, Chester

$205,000

Charming opportunity on 3.18 open acres with a stream along the back of the property adding natural beauty and a peaceful setting. This 3-bedroom ranch offers easy single-level living and a functional layout, ready for updates and your personal touch. Ideal for handy buyers, renovators, or buyers looking to build equity. The spacious land provides room for gardening, animals, recreation, or future expansion while enjoying privacy and a country feel. Property includes a garage, chicken coop, and additional shed for storage, hobbies, or projects. A rare chance to create your dream rural retreat, homestead, or renovation investment with land, outbuildings, and water feature all in one.

3 Beds ⋅ 2 Baths ⋅ 5075068 MLS

Charming opportunity on 3.18 open acres with a stream along the back of the property adding natural beauty and a peaceful setting. This 3-bedroom ranch offers easy single-level living and a functional layout, ready for updates and your personal touch. Ideal for handy buyers, renovators, or buyers looking to build equity. The spacious land provides room for gardening, animals, recreation, or future expansion while enjoying privacy and a country feel. Property includes a garage, chicken coop, and additional shed for storage, hobbies, or projects. A rare chance to create your dream rural retreat, homestead, or renovation investment with land, outbuildings, and water feature all in one.

1876 Popple Dungeon Rd, Chester

$190,000

Set on 18 forested acres along quiet, dead-end Potash Brook Road in Chester, this peaceful cabin offers a simple and inviting Vermont retreat with no through traffic and a true sense of calm. Well suited for a hunting camp, recreational getaway, or quiet place to unwind, the property provides privacy, natural surroundings, and easy access to the outdoor lifestyle Southern Vermont is known for. The cabin includes propane heat, a spring well, septic, and an inviting and cozy living space for weekends, seasonal use, or time away from the noise of everyday life. The structure will require new footings and is being sold as is, offering an opportunity for the next owner to make needed improvements while enjoying the land, setting, and existing cabin. The property is wooded and rustic in feel, with room to explore, observe wildlife, and enjoy the changing seasons. A brook runs through the land, adding natural character to the setting. Whether used as a base for hunting, hiking, snowmobiling, skiing, or simply relaxing in the woods, this property offers a practical and appealing Vermont escape. Ski areas, trail networks, fishing, and year-round recreation are all within reach, while the setting itself remains quiet, private, and refreshingly simple. If you are looking for land, privacy, and a modest cabin with key systems already in place, this Chester retreat is well worth a look.

2 Beds ⋅ 1 Baths ⋅ 5098053 MLS

Set on 18 forested acres along quiet, dead-end Potash Brook Road in Chester, this peaceful cabin offers a simple and inviting Vermont retreat with no through traffic and a true sense of calm. Well suited for a hunting camp, recreational getaway, or quiet place to unwind, the property provides privacy, natural surroundings, and easy access to the outdoor lifestyle Southern Vermont is known for. The cabin includes propane heat, a spring well, septic, and an inviting and cozy living space for weekends, seasonal use, or time away from the noise of everyday life. The structure will require new footings and is being sold as is, offering an opportunity for the next owner to make needed improvements while enjoying the land, setting, and existing cabin. The property is wooded and rustic in feel, with room to explore, observe wildlife, and enjoy the changing seasons. A brook runs through the land, adding natural character to the setting. Whether used as a base for hunting, hiking, snowmobiling, skiing, or simply relaxing in the woods, this property offers a practical and appealing Vermont escape. Ski areas, trail networks, fishing, and year-round recreation are all within reach, while the setting itself remains quiet, private, and refreshingly simple. If you are looking for land, privacy, and a modest cabin with key systems already in place, this Chester retreat is well worth a look.

1372 Potash Brook Rd, Chester

$180,000

Opportunity awaits with this charming home nestled in the heart of Chester, Vermont. Just steps from the village's quaint shops, restaurants, galleries, and local amenities, this property offers a great location and endless potential. In need of some updating, this home is the perfect project for investors, contractors, or buyers looking to restore its character and create something truly special. Whether you're envisioning a primary residence, vacation getaway, or investment property, the possibilities are wide open. With solid bones, classic Vermont charm, and a highly desirable village setting, this is your chance to bring your take to one of Southern Vermont's most beloved communities. Enjoy easy access to skiing, hiking, snowmobiling, and year round recreation all while being part of Chester's vibrant small town atmosphere.

3 Beds ⋅ 2 Baths ⋅ 5100719 MLS

Opportunity awaits with this charming home nestled in the heart of Chester, Vermont. Just steps from the village's quaint shops, restaurants, galleries, and local amenities, this property offers a great location and endless potential. In need of some updating, this home is the perfect project for investors, contractors, or buyers looking to restore its character and create something truly special. Whether you're envisioning a primary residence, vacation getaway, or investment property, the possibilities are wide open. With solid bones, classic Vermont charm, and a highly desirable village setting, this is your chance to bring your take to one of Southern Vermont's most beloved communities. Enjoy easy access to skiing, hiking, snowmobiling, and year round recreation all while being part of Chester's vibrant small town atmosphere.

641 Depot St, Chester

$135,000

Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State Wastewater Permit and Town Subdivision Permit. This property is located within a mile from Pinnacle Recreation Facility and only 12 miles to Okemo Mt. Ski area.

5058859 MLS

Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State Wastewater Permit and Town Subdivision Permit. This property is located within a mile from Pinnacle Recreation Facility and only 12 miles to Okemo Mt. Ski area.

918 Lovers Lane Rd, Chester

$80,000

Building opportunity! This lot is ready to go with a Waste water permit and septic design in place. Utility easements have also been made so the property should be able to benefit from being able to start construction swiftly. The lot features two fields separated by a tree line with potential for great views.

5100498 MLS

Building opportunity! This lot is ready to go with a Waste water permit and septic design in place. Utility easements have also been made so the property should be able to benefit from being able to start construction swiftly. The lot features two fields separated by a tree line with potential for great views.

734 Gould Rd, Chester

$28,500

This 3.2-acre lot is ideal for anyone seeking a piece of Vermont to enjoy the outdoors. With Great Brook running through the property, you can catch brook trout, pick elderberries, or explore the terrain right at home. A flat, cleared half-acre area is ready for use. Bring your camping gear or RV to relax in a quiet setting that remains close to local conveniences. Just six miles away, quaint downtown Chester offers antique shops, bookstores, the historic Stone Village, local dining, and community events like the annual Chester Fall Festival. Use this location as a central starting point to explore nearby attractions all within 12 miles, including Okemo Mountain Resort, Ludlow, Grafton Village Cheese, and the Vermont Country Store in Rockingham, plus all the everyday conveniences of Springfield. Outdoor enthusiasts can also head to Williams River State Park for fishing and hiking, or enjoy hiking, snowshoeing, and Nordic skiing along the Lost Mine Trail while taking in views of Mount Ascutney. No permitting or perc testing has been completed. Buyers must do their own due dillegence.

5108359 MLS

This 3.2-acre lot is ideal for anyone seeking a piece of Vermont to enjoy the outdoors. With Great Brook running through the property, you can catch brook trout, pick elderberries, or explore the terrain right at home. A flat, cleared half-acre area is ready for use. Bring your camping gear or RV to relax in a quiet setting that remains close to local conveniences. Just six miles away, quaint downtown Chester offers antique shops, bookstores, the historic Stone Village, local dining, and community events like the annual Chester Fall Festival. Use this location as a central starting point to explore nearby attractions all within 12 miles, including Okemo Mountain Resort, Ludlow, Grafton Village Cheese, and the Vermont Country Store in Rockingham, plus all the everyday conveniences of Springfield. Outdoor enthusiasts can also head to Williams River State Park for fishing and hiking, or enjoy hiking, snowshoeing, and Nordic skiing along the Lost Mine Trail while taking in views of Mount Ascutney. No permitting or perc testing has been completed. Buyers must do their own due dillegence.

1673 Dean Brook Rd, Chester