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$390,000

Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester’s Stone Village, the Grist Mill, and Smitty’s Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals.

3 Beds ⋅ 2 Baths ⋅ 5086202 MLS

Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester’s Stone Village, the Grist Mill, and Smitty’s Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals.

663 Depot St, Chester

$549,000

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

4 Beds ⋅ 3 Baths ⋅ 5086105 MLS

Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

3341 Trebo Rd, Chester

$899,900

WOW Price Reduced ! No Cookie Cutter Here! Check Out this Stunning Contemporary Farmhouse in the Quintessential New England small town Of Chester, NH located in a fantastic Small Development with only 9 Detached Condo's. The home Features 3 beds,2 1/2 baths with an Open concept layout. The GORGEOUS Kitchen has all the bells and whistles, granite counter tops, a Huge island, stainless steel gas stove with vent hood that connects to a large living room with Gleaming Hardwoods floors. You are sure to Enjoy the Elegant Dining room adjacent to the kitchen along with a home office with French Doors. The 1st Floor Primary Suite has Hardwood floors and a STUNNING Tiled Shower, double Vanity, and a walk-in closet that also connects to the Laundry Room. The mud area and powder room complete the first level. Upstairs you will find a MASSIVE Bonus room that is sure to be an amazing place to entertain or just hang out with the family. The 2nd bedroom is Gigantic and can be another primary suite, it has a large walk-in closet and connects to a large full bathroom with double vanity. The 3rd bedroom is also Huge and connects to the full bathroom as well. Outside you have a huge deck and plenty of room for the kids or pets to run around. The massive basement provides tons of storage and space that is ready to finish. Quick Closing Possible. Some photos are Virtually Staged. This is a MUST SEE HOME !

3 Beds ⋅ 3 Baths ⋅ 5084557 MLS

WOW Price Reduced ! No Cookie Cutter Here! Check Out this Stunning Contemporary Farmhouse in the Quintessential New England small town Of Chester, NH located in a fantastic Small Development with only 9 Detached Condo's. The home Features 3 beds,2 1/2 baths with an Open concept layout. The GORGEOUS Kitchen has all the bells and whistles, granite counter tops, a Huge island, stainless steel gas stove with vent hood that connects to a large living room with Gleaming Hardwoods floors. You are sure to Enjoy the Elegant Dining room adjacent to the kitchen along with a home office with French Doors. The 1st Floor Primary Suite has Hardwood floors and a STUNNING Tiled Shower, double Vanity, and a walk-in closet that also connects to the Laundry Room. The mud area and powder room complete the first level. Upstairs you will find a MASSIVE Bonus room that is sure to be an amazing place to entertain or just hang out with the family. The 2nd bedroom is Gigantic and can be another primary suite, it has a large walk-in closet and connects to a large full bathroom with double vanity. The 3rd bedroom is also Huge and connects to the full bathroom as well. Outside you have a huge deck and plenty of room for the kids or pets to run around. The massive basement provides tons of storage and space that is ready to finish. Quick Closing Possible. Some photos are Virtually Staged. This is a MUST SEE HOME !

14 Stacey Ln Unit 2, Chester

$419,900

Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless steel appliances. Relax by the gas fireplace in the inviting living room, highlighted by soaring vaulted ceilings and rustic exposed wood beams. Accommodating family and guests with ease, the layout features 5 generous bedrooms and 2 updated baths. The primary suite acts as your own private sanctuary, complete with an ensuite bath featuring a double vanity, and a private balcony. The flexible lower-level bonus space easily adapts to your lifestyle - ideal for a home gym, media room, or private office. Outdoor living is a breeze while you're relaxing bug-free on the screened porch! Tucked away on a quiet dead-end street, this turn-key residence pairs privacy with convenience with an easy walk to the vibrant Chester Green. Additional highlights include the boiler replaced in 2021, the freshly painted interior in 2022, new windows installed throughout the house in 2021 and 2025, a new sump pump installed in 2023, and a newly paved driveway in 2024. Electrical updates and a full foundation restoration have been completed in 2026 for long-term structural integrity (inquire for more information or see under Attached Documents), providing peace of mind for years to come. Don't miss your chance to own this move-in ready gem in a prime Chester location!

5 Beds ⋅ 2 Baths ⋅ 5082995 MLS

Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless steel appliances. Relax by the gas fireplace in the inviting living room, highlighted by soaring vaulted ceilings and rustic exposed wood beams. Accommodating family and guests with ease, the layout features 5 generous bedrooms and 2 updated baths. The primary suite acts as your own private sanctuary, complete with an ensuite bath featuring a double vanity, and a private balcony. The flexible lower-level bonus space easily adapts to your lifestyle - ideal for a home gym, media room, or private office. Outdoor living is a breeze while you're relaxing bug-free on the screened porch! Tucked away on a quiet dead-end street, this turn-key residence pairs privacy with convenience with an easy walk to the vibrant Chester Green. Additional highlights include the boiler replaced in 2021, the freshly painted interior in 2022, new windows installed throughout the house in 2021 and 2025, a new sump pump installed in 2023, and a newly paved driveway in 2024. Electrical updates and a full foundation restoration have been completed in 2026 for long-term structural integrity (inquire for more information or see under Attached Documents), providing peace of mind for years to come. Don't miss your chance to own this move-in ready gem in a prime Chester location!

176 Meadow Rd, Chester

$299,000

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

$399,000

This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.

4 Beds ⋅ 3 Baths ⋅ 5073147 MLS

This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.

40 Fenton Rd, Chester

$1,250,000

HOME TO BE BUILT! THIS IS THE LAST LOT REMAINING!! Welcome to Colby Farm, an exclusive enclave of just 10 beautifully crafted single family homes, tucked away on a quiet cul de sac. Thoughtfully designed with both elegance & functionality in mind, each home offers spacious, customizable floor plans, allowing buyers to select finishes, appliances, and details to reflect their personal style. BRING YOUR OWN PLAN OR BUILD THIS FEATURED HOME. This farmhouse style home is a 3,018 sq. ft. retreat that blends timeless charm with modern living. The plan includes three generously sized bedrooms, two and a half well appointed bathrooms, & a convenient second floor laundry. At the heart of the home, the gourmet kitchen is designed to be tailored to your taste, with allowances for appliances, cabinetry, countertops, and finishes. A large center island & walk in pantry create a space that works beautifully for both everyday living and entertaining. The layout also features a flexible room ideal for a home office or den, an expansive great room for gatherings, & a welcoming mudroom leading to a spacious two car garage, all designed with comfort and livability in mind. Set along a scenic country road, Colby Farm offers the perfect balance of modern luxury and rural charm. A neighboring horse farm and 18 acres of conservation land enhance the peaceful surroundings, while the absence of condo fees adds to the appeal. Choose from the builder’s thoughtfully designed plans or bring your own vision to life. Photos are a facsimile of previous build.

3 Beds ⋅ 3 Baths ⋅ 5072786 MLS

HOME TO BE BUILT! THIS IS THE LAST LOT REMAINING!! Welcome to Colby Farm, an exclusive enclave of just 10 beautifully crafted single family homes, tucked away on a quiet cul de sac. Thoughtfully designed with both elegance & functionality in mind, each home offers spacious, customizable floor plans, allowing buyers to select finishes, appliances, and details to reflect their personal style. BRING YOUR OWN PLAN OR BUILD THIS FEATURED HOME. This farmhouse style home is a 3,018 sq. ft. retreat that blends timeless charm with modern living. The plan includes three generously sized bedrooms, two and a half well appointed bathrooms, & a convenient second floor laundry. At the heart of the home, the gourmet kitchen is designed to be tailored to your taste, with allowances for appliances, cabinetry, countertops, and finishes. A large center island & walk in pantry create a space that works beautifully for both everyday living and entertaining. The layout also features a flexible room ideal for a home office or den, an expansive great room for gatherings, & a welcoming mudroom leading to a spacious two car garage, all designed with comfort and livability in mind. Set along a scenic country road, Colby Farm offers the perfect balance of modern luxury and rural charm. A neighboring horse farm and 18 acres of conservation land enhance the peaceful surroundings, while the absence of condo fees adds to the appeal. Choose from the builder’s thoughtfully designed plans or bring your own vision to life. Photos are a facsimile of previous build.

37 Colby Farm Rd, Chester

$169,000

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway. A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons. This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

1 Beds ⋅ 1 Baths ⋅ 5067929 MLS

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny house while working on the original home. Consider the possibility of removing the older structure to make way for something new, or simply use the tiny house as your Vermont getaway. A stone walkway leads gracefully down to the river, providing a tranquil connection to nature. Both structures are believed to be elevated above the flood zone, ensuring peace of mind in all seasons. This lovely property is a nature lover's dream and a rare opportunity to embrace the essence of Vermont's natural beauty.

3019 Popple Dungeon Rd, Chester