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Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment.

5 Beds ⋅ 3 Baths ⋅ 5099745 MLS

Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment.

1470 Popple Dungeon Rd, Chester

$749,999

JUST LISTED | NOW OFFERED AT $749,999! FRESHLY PAINTED! 2.88 ACRES! Welcome to 88 Crawford Road, a breathtaking residential haven nestled in the heart of Chester, New Hampshire. This exquisite colonial estate seamlessly blends sophisticated architectural design with the tranquil beauty of its lush, private surroundings. Offering an expansive 3,675 square feet (3146 Above Grade) (529 Below Grade) of meticulously crafted living space, the residence features 4 generously appointed bedrooms, 2.5 elegant bathrooms, and a freshly painted interior throughout that creates a bright, turnkey atmosphere. From the grand, winding driveway to the majestic facade framed by mature trees, every detail of this home exudes luxury. The interior promises unparalleled comfort with expansive room layouts, high-end finishes, and an abundance of natural light pouring through magnificent feature windows. Perfectly situated for those who demand both privacy and convenience, 88 Crawford Road offers an idyllic retreat without sacrificing accessibility. Located in the charming, historic town of Chester, you are mere minutes from top-rated local schools, pristine parks, and boutique community dining. For commuters, the property provides seamless access to major regional routes, putting the bustling commercial hubs of Manchester and Salem within easy driving distance, while offering a straightforward, scenic commute to downtown Boston and the gorgeous New Hampshire seacoast.

4 Beds ⋅ 3 Baths ⋅ 5097711 MLS

JUST LISTED | NOW OFFERED AT $749,999! FRESHLY PAINTED! 2.88 ACRES! Welcome to 88 Crawford Road, a breathtaking residential haven nestled in the heart of Chester, New Hampshire. This exquisite colonial estate seamlessly blends sophisticated architectural design with the tranquil beauty of its lush, private surroundings. Offering an expansive 3,675 square feet (3146 Above Grade) (529 Below Grade) of meticulously crafted living space, the residence features 4 generously appointed bedrooms, 2.5 elegant bathrooms, and a freshly painted interior throughout that creates a bright, turnkey atmosphere. From the grand, winding driveway to the majestic facade framed by mature trees, every detail of this home exudes luxury. The interior promises unparalleled comfort with expansive room layouts, high-end finishes, and an abundance of natural light pouring through magnificent feature windows. Perfectly situated for those who demand both privacy and convenience, 88 Crawford Road offers an idyllic retreat without sacrificing accessibility. Located in the charming, historic town of Chester, you are mere minutes from top-rated local schools, pristine parks, and boutique community dining. For commuters, the property provides seamless access to major regional routes, putting the bustling commercial hubs of Manchester and Salem within easy driving distance, while offering a straightforward, scenic commute to downtown Boston and the gorgeous New Hampshire seacoast.

88 Crawford Rd, Chester

$749,900

First time in 26 years, one of only eight homes on Abenaki Circle is ready for its next chapter. Cared for by the same family since it was built, this distinctive home combines privacy, neighborhood connection, and special spaces, turning everyday moments into warm memories. Walk up onto the farmer's porch and into the home, and the centerpiece of the home greets you: an open-concept kitchen with an extended breakfast bar spills into a warm dining room and oversized great room defined by soaring vaulted ceilings, exposed wood beams, and a striking brick fireplace with custom mantel. Hardwood and tile flooring and natural wood finishes tie all three spaces together, creating the kind of first floor built for both everyday life and holiday gatherings full of stories and laughter. A dedicated home office/den and 1/4 bath with laundry round out this level, adding everyday convenience. Upstairs, the primary suite offers a peaceful retreat with a walk-in closet and ensuite bath, while two additional bedrooms, each with custom closets, share a full bath. The beautifully finished third level, with hardwood floors and exposed beams, extends the home further, providing a versatile bonus room, ideal as an office, playroom, or studio. Step back outside onto the farmer's porch or the expansive two-tiered back deck, framed by mature landscaping, established hydrangeas, and stone hardscaping, creating settings where morning coffee turns into watching deer move quietly through the yard, while hearing birdsong throughout the day. A well-organized custom mudroom, storage shed with firewood lean-to, full irrigation, and two-car garage provide everyday function to make the home easy to live in. Located in the acclaimed Chester Academy and Pinkerton Academy school communities, the home is minutes from Wason Pond with easy access to I-93, Route 101, and Manchester Airport. Lifetimes are built around homes with this type of charm, and rarely come to market in this quiet corner of Chester.

3 Beds ⋅ 3 Baths ⋅ 5108579 MLS

First time in 26 years, one of only eight homes on Abenaki Circle is ready for its next chapter. Cared for by the same family since it was built, this distinctive home combines privacy, neighborhood connection, and special spaces, turning everyday moments into warm memories. Walk up onto the farmer's porch and into the home, and the centerpiece of the home greets you: an open-concept kitchen with an extended breakfast bar spills into a warm dining room and oversized great room defined by soaring vaulted ceilings, exposed wood beams, and a striking brick fireplace with custom mantel. Hardwood and tile flooring and natural wood finishes tie all three spaces together, creating the kind of first floor built for both everyday life and holiday gatherings full of stories and laughter. A dedicated home office/den and 1/4 bath with laundry round out this level, adding everyday convenience. Upstairs, the primary suite offers a peaceful retreat with a walk-in closet and ensuite bath, while two additional bedrooms, each with custom closets, share a full bath. The beautifully finished third level, with hardwood floors and exposed beams, extends the home further, providing a versatile bonus room, ideal as an office, playroom, or studio. Step back outside onto the farmer's porch or the expansive two-tiered back deck, framed by mature landscaping, established hydrangeas, and stone hardscaping, creating settings where morning coffee turns into watching deer move quietly through the yard, while hearing birdsong throughout the day. A well-organized custom mudroom, storage shed with firewood lean-to, full irrigation, and two-car garage provide everyday function to make the home easy to live in. Located in the acclaimed Chester Academy and Pinkerton Academy school communities, the home is minutes from Wason Pond with easy access to I-93, Route 101, and Manchester Airport. Lifetimes are built around homes with this type of charm, and rarely come to market in this quiet corner of Chester.

29 Abenaki Cir, Chester

$700,000

A wonderful retreat on 35+/- acres in Chester is ready for new owners to enjoy. The gated, serpentine driveway threads its way through the woods and by the large pond, taking in the lovely, open meadow with stone works and gardens leading to the classic custom 2+ bedroom, 3 bath chalet in an absolutely charming setting. As if transported from the Alps, the architectural features, such as handsome exposed wood beams, cathedral ceiling with a large wrought iron chandelier, a dramatic wooden spiral staircase and ceramic tile, all echo elements of style from the slopes of Northern Italy. The current owners have restored and upgraded each of the three full baths with a spa-like sensibility and added cosmetic upgrades to the kitchen and throughout the home. The cozy living room features a woodburning fireplace and as well as a mini split to warm and cool off as needed. The cheerful kitchen with quartz counters and breakfast bar adjoins the dining area. A three-quarter bath with a luxurious tiled shower completes the first floor. The spiral stairway leads to a spacious light filled living/play area with a wood burning fireplace and a balcony to enjoy the stunning view. A third floor loft/aerie makes a wonderful study or play area. A solar array with two Tesla batteries offsets the electric bill and protects the property in a power outage. The two car garage is neatly tucked under the patio that features an inviting hot tub. Out front, the stone patio will delight with its custom granite picnic table and benches- a remarkable conversation piece! There are trails to hike through the woods, frontage along the Williams River for trout fishing, an old stone foundation, and a delightful pond with a floating dock to swim and relax with friends and family, all in a mesmerizing setting within 5 min. to the Chester village. Close to Okemo and several other ski mountains. This unique property would make an awesome vacation or full time home.

2 Beds ⋅ 3 Baths ⋅ 5107796 MLS

A wonderful retreat on 35+/- acres in Chester is ready for new owners to enjoy. The gated, serpentine driveway threads its way through the woods and by the large pond, taking in the lovely, open meadow with stone works and gardens leading to the classic custom 2+ bedroom, 3 bath chalet in an absolutely charming setting. As if transported from the Alps, the architectural features, such as handsome exposed wood beams, cathedral ceiling with a large wrought iron chandelier, a dramatic wooden spiral staircase and ceramic tile, all echo elements of style from the slopes of Northern Italy. The current owners have restored and upgraded each of the three full baths with a spa-like sensibility and added cosmetic upgrades to the kitchen and throughout the home. The cozy living room features a woodburning fireplace and as well as a mini split to warm and cool off as needed. The cheerful kitchen with quartz counters and breakfast bar adjoins the dining area. A three-quarter bath with a luxurious tiled shower completes the first floor. The spiral stairway leads to a spacious light filled living/play area with a wood burning fireplace and a balcony to enjoy the stunning view. A third floor loft/aerie makes a wonderful study or play area. A solar array with two Tesla batteries offsets the electric bill and protects the property in a power outage. The two car garage is neatly tucked under the patio that features an inviting hot tub. Out front, the stone patio will delight with its custom granite picnic table and benches- a remarkable conversation piece! There are trails to hike through the woods, frontage along the Williams River for trout fishing, an old stone foundation, and a delightful pond with a floating dock to swim and relax with friends and family, all in a mesmerizing setting within 5 min. to the Chester village. Close to Okemo and several other ski mountains. This unique property would make an awesome vacation or full time home.

1260 Grafton Rd, Chester

$699,900

Here is your opportunity to get into Chesterbrook Estates! Welcome to 98 Lady Slipper Lane. Set in a private neighborhood, this 3-bedroom Colonial home in Chester NH offers 2.5 baths, approximately 3,260 square feet of finished living space across three levels, and more than 1.25 acres. Priced under $700,000, this 2004-built home pairs a spacious floor plan with a peaceful setting overlooking a serene pond. Inside, you'll find plenty of room to spread out, including a large family room designed for comfortable everyday living and gatherings. Three finished levels provide added flexibility, highlighted by a third-floor bonus room that expands the possibilities for additional living, work, recreation, or hobby space. Need more space? The walk-out lower level offers future expansion possibilities. Outside, the back deck creates an inviting place to enjoy the natural surroundings and pond views. Additional features include a newer roof and two-car garage and whole house pellet stove heating system that is connected to the duct work. Enjoy the private oasis in your back yard, while still benefitting from a neighborhood setting. All of this and part of the Pinkerton Academy School District, this is one that you will not want to miss out on. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ 5112319 MLS

Here is your opportunity to get into Chesterbrook Estates! Welcome to 98 Lady Slipper Lane. Set in a private neighborhood, this 3-bedroom Colonial home in Chester NH offers 2.5 baths, approximately 3,260 square feet of finished living space across three levels, and more than 1.25 acres. Priced under $700,000, this 2004-built home pairs a spacious floor plan with a peaceful setting overlooking a serene pond. Inside, you'll find plenty of room to spread out, including a large family room designed for comfortable everyday living and gatherings. Three finished levels provide added flexibility, highlighted by a third-floor bonus room that expands the possibilities for additional living, work, recreation, or hobby space. Need more space? The walk-out lower level offers future expansion possibilities. Outside, the back deck creates an inviting place to enjoy the natural surroundings and pond views. Additional features include a newer roof and two-car garage and whole house pellet stove heating system that is connected to the duct work. Enjoy the private oasis in your back yard, while still benefitting from a neighborhood setting. All of this and part of the Pinkerton Academy School District, this is one that you will not want to miss out on. Schedule your private showing today!

98 Lady Slipper Ln, Chester

$635,999

BACK ON MARKET DUE TO BUYER FINANCING NO FAULT OF THE HOME! Property previously appraised above the current list price, offering added confidence for buyers. Now offered at $635,999! Sellers are also willing to assist with buyer closing costs with an acceptable offer. Beautifully renovated 4-bedroom, 2-bath Chester home offering nearly 2,000 sq. ft. of finished living space on 1.2 private acres. Enjoy a renovated kitchen, updated bathrooms, new flooring, fresh paint and a finished lower level offering flexible additional living space. Outside, enjoy your own backyard retreat featuring an in-ground pool with brand-new liner, spacious new deck and plenty of room for entertaining. An oversized detached 3-car garage provides exceptional space for vehicles, storage, hobbies or a workshop. Additional improvements include new siding, updated windows and a newer roof. Located in desirable Chester and the Pinkerton Academy school district. POOL • 3-CAR GARAGE • 1.2 ACRES • FINISHED LOWER LEVEL • RENOVATED INTERIOR • MOVE-IN READY

4 Beds ⋅ 2 Baths ⋅ 5094684 MLS

BACK ON MARKET DUE TO BUYER FINANCING NO FAULT OF THE HOME! Property previously appraised above the current list price, offering added confidence for buyers. Now offered at $635,999! Sellers are also willing to assist with buyer closing costs with an acceptable offer. Beautifully renovated 4-bedroom, 2-bath Chester home offering nearly 2,000 sq. ft. of finished living space on 1.2 private acres. Enjoy a renovated kitchen, updated bathrooms, new flooring, fresh paint and a finished lower level offering flexible additional living space. Outside, enjoy your own backyard retreat featuring an in-ground pool with brand-new liner, spacious new deck and plenty of room for entertaining. An oversized detached 3-car garage provides exceptional space for vehicles, storage, hobbies or a workshop. Additional improvements include new siding, updated windows and a newer roof. Located in desirable Chester and the Pinkerton Academy school district. POOL • 3-CAR GARAGE • 1.2 ACRES • FINISHED LOWER LEVEL • RENOVATED INTERIOR • MOVE-IN READY

632 Raymond Rd, Chester

$599,900

Step back in time without giving up today’s modern comforts in this thoughtfully designed antique replica Cape, beautifully crafted by the renowned Tammy Grimes. Set privately on 2.8 serene acres, this exceptional home captures the character, warmth, and timeless charm of an antique New England home while offering the conveniences and updates today’s buyers desire. Inside, you’ll find beautifully preserved character paired with thoughtful modern improvements. The newly redesigned first-floor bathroom features a stunning tiled shower, while the custom kitchen offers both functionality and distinctive style. Cozy up by the pellet stove or enjoy the comfort of forced hot-air heat throughout the home. A whole-house generator provides added peace of mind in every season. The private, peaceful setting offers plenty of room to relax, entertain, garden, or simply enjoy the tranquility of your surroundings. With its classic Cape architecture, inviting interior, custom details, and modern amenities, this is a truly special property that blends the romance of an antique home with the comfort of contemporary living. A rare opportunity to own a piece of timeless New England charm in a beautiful Chester setting.

3 Beds ⋅ 2 Baths ⋅ 5106758 MLS

Step back in time without giving up today’s modern comforts in this thoughtfully designed antique replica Cape, beautifully crafted by the renowned Tammy Grimes. Set privately on 2.8 serene acres, this exceptional home captures the character, warmth, and timeless charm of an antique New England home while offering the conveniences and updates today’s buyers desire. Inside, you’ll find beautifully preserved character paired with thoughtful modern improvements. The newly redesigned first-floor bathroom features a stunning tiled shower, while the custom kitchen offers both functionality and distinctive style. Cozy up by the pellet stove or enjoy the comfort of forced hot-air heat throughout the home. A whole-house generator provides added peace of mind in every season. The private, peaceful setting offers plenty of room to relax, entertain, garden, or simply enjoy the tranquility of your surroundings. With its classic Cape architecture, inviting interior, custom details, and modern amenities, this is a truly special property that blends the romance of an antique home with the comfort of contemporary living. A rare opportunity to own a piece of timeless New England charm in a beautiful Chester setting.

15 Ledge Rd, Chester

$579,900

This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

5090837 MLS

This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

197a Chester St, Chester

$579,900

This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

2 Beds ⋅ 2 Baths ⋅ 5090733 MLS

This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

197 Chester St, Chester

$475,000

Discover the ideal combination of a serene setting with this turnkey property nestled in an idyllic neighborhood just minutes from major commuter routes and everyday conveniences. Fresh, neutral paint throughout paired with brand-new carpeting ensure this residence is prepped for its' next owner. High-value recent updates including a newer furnace, modern windows, and durable 50-year architectural shingles with plenty of life left provide an enduring sense of comfort, security, and peace of mind. Inside, you will be delighted by the spacious, flexible layout. The main level features a flexible floor plan with an open flow between the eat-in kitchen and large dining or living room, offering abundant space for memorable gatherings, just in time for the upcoming Holidays. You will also find two versatile rooms, ideal as a den plus a dedicated home office for the executive. A practical 3/4 bath with convenient main-level laundry rounds out the first floor nicely. Retreat to the second level to find a wonderful primary suite, two additional nicely-sized bedrooms, and a full bathroom. The "begging to be finished" lower level, already equipped with a pellet stove and custom bar, provides even more living space potential. Customize it to fit your needs, whether as an exercise area, home theater, or game room. Step outside to your nearly 5-acre, fully fenced private yard surrounded by nature. You'll love relaxing on the deck with your morning coffee, hosting vibrant summer barbecues, playing outdoor games, or taking advantage of the abundant space to build your dream garden. Chester is a quintessential New England town known for its' historic character and peaceful rural setting, complete with beloved year-round traditions such as the Chester Town Fair. The property is part of the prestigious Pinkerton Academy school district & offers endless nearby recreation at the Wason Pond Conservation Area, featuring walking trails & swimming. OFFER DEADLINE 10/19 @ 7 PM.

3 Beds ⋅ 2 Baths ⋅ 5114691 MLS

Discover the ideal combination of a serene setting with this turnkey property nestled in an idyllic neighborhood just minutes from major commuter routes and everyday conveniences. Fresh, neutral paint throughout paired with brand-new carpeting ensure this residence is prepped for its' next owner. High-value recent updates including a newer furnace, modern windows, and durable 50-year architectural shingles with plenty of life left provide an enduring sense of comfort, security, and peace of mind. Inside, you will be delighted by the spacious, flexible layout. The main level features a flexible floor plan with an open flow between the eat-in kitchen and large dining or living room, offering abundant space for memorable gatherings, just in time for the upcoming Holidays. You will also find two versatile rooms, ideal as a den plus a dedicated home office for the executive. A practical 3/4 bath with convenient main-level laundry rounds out the first floor nicely. Retreat to the second level to find a wonderful primary suite, two additional nicely-sized bedrooms, and a full bathroom. The "begging to be finished" lower level, already equipped with a pellet stove and custom bar, provides even more living space potential. Customize it to fit your needs, whether as an exercise area, home theater, or game room. Step outside to your nearly 5-acre, fully fenced private yard surrounded by nature. You'll love relaxing on the deck with your morning coffee, hosting vibrant summer barbecues, playing outdoor games, or taking advantage of the abundant space to build your dream garden. Chester is a quintessential New England town known for its' historic character and peaceful rural setting, complete with beloved year-round traditions such as the Chester Town Fair. The property is part of the prestigious Pinkerton Academy school district & offers endless nearby recreation at the Wason Pond Conservation Area, featuring walking trails & swimming. OFFER DEADLINE 10/19 @ 7 PM.

24 Rand Dr, Chester

$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

$330,000

If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad bedrooms make up the second floor. The home has a new roof, new on-demand hot water system, fresh stain on the log exterior, updated electrical, brand new LVL carrying beam and floor joists, new interior trap door basement access and stairs, and new laundry station in the basement. Many other practical upgrades and extensive landscaping has been made and this home is in mint condition. The sellers recently did a drinking water test, had the septic pumped, and did a home inspection, leaving no stone unturned. The 11 acre parcel transitions from a large sunny open yard to old stone walls and hemlock-hardwood forest and rises nearly to the humble summit of Davidson Hill (1053' elevation). The owners let a neighboring property tap most of the maple trees in exchange for maple syrup. The house is located just feet from Trail #5 of the Hawks Mountain Ridge Riders VAST trail network, and is minutes from downtown Springfield and Chester. Just 15 minutes from I-91 and Okemo. While surrounded by forest and situated for optimum privacy, this home does have seasonal views of Mt. Ascutney and there is a good possibility of spectacular views higher up on the property. The height of the property would make an awesome camping or gazebo spot. Many logging roads and four wheeler trails throughout the property. The dog on the couch does not convey.

2 Beds ⋅ 1 Baths ⋅ 5102316 MLS

If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad bedrooms make up the second floor. The home has a new roof, new on-demand hot water system, fresh stain on the log exterior, updated electrical, brand new LVL carrying beam and floor joists, new interior trap door basement access and stairs, and new laundry station in the basement. Many other practical upgrades and extensive landscaping has been made and this home is in mint condition. The sellers recently did a drinking water test, had the septic pumped, and did a home inspection, leaving no stone unturned. The 11 acre parcel transitions from a large sunny open yard to old stone walls and hemlock-hardwood forest and rises nearly to the humble summit of Davidson Hill (1053' elevation). The owners let a neighboring property tap most of the maple trees in exchange for maple syrup. The house is located just feet from Trail #5 of the Hawks Mountain Ridge Riders VAST trail network, and is minutes from downtown Springfield and Chester. Just 15 minutes from I-91 and Okemo. While surrounded by forest and situated for optimum privacy, this home does have seasonal views of Mt. Ascutney and there is a good possibility of spectacular views higher up on the property. The height of the property would make an awesome camping or gazebo spot. Many logging roads and four wheeler trails throughout the property. The dog on the couch does not convey.

302 Davidson Hill Rd, Chester

$255,000

Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly blending old-world appeal with boundless equity-building potential, this quintessential New England abode serves as the perfect canvas for your personal touch. It is entirely ready for cosmetic enhancements, custom modern finishes, and tailored design choices that will allow you to completely personalize the space to match your unique vision. Just 15 minutes from I-91 and Springfield VT, 35 minutes to Keene, NH and 40 minutes to Lebanon NH. Stop on by and see it for yourself!

3 Beds ⋅ 2 Baths ⋅ 5106226 MLS

Welcome to 159 Lower Bartonsville Road, a charming carriage house nestled along a scenic country farm road in Rockingham, Vermont, just moments from the picturesque restored Bartonsville covered bridge. This 3 bed, 1.5 bath property features authentic 1830s architecture and timeless rustic character, offering a solid structural foundation with much of its original detail preserved. Seamlessly blending old-world appeal with boundless equity-building potential, this quintessential New England abode serves as the perfect canvas for your personal touch. It is entirely ready for cosmetic enhancements, custom modern finishes, and tailored design choices that will allow you to completely personalize the space to match your unique vision. Just 15 minutes from I-91 and Springfield VT, 35 minutes to Keene, NH and 40 minutes to Lebanon NH. Stop on by and see it for yourself!

159 Lower Bartonsville Rd, Chester

$229,000

Sometimes, just the right amount of space is exactly what you need. Set on two pleasant acres in Chester, this tidy 2-bedroom, ¾-bath home offers comfortable, efficient one-level living with a practical layout that makes everyday life easy. Inside, the home is bright and well cared for, with a modern kitchen, comfortable living space, two nicely sized bedrooms, laundry, and the convenience of everything on one floor. Propane heat keeps things simple and efficient, while the manageable footprint means less house to maintain and more time to enjoy Vermont. Outside, the level lawn provides plenty of usable space for gardening, pets, a fire pit, or simply relaxing outdoors without taking on an overwhelming property. A detached two-car garage offers excellent parking, storage, and room for the tools and gear that come with Vermont living. Whether you're looking for a first home, ready to simplify, or searching for a comfortable retirement property with minimal stairs and manageable upkeep, this Chester home checks a lot of boxes. Simple, practical, and easy to maintain, it is a home that makes perfect sense.

2 Beds ⋅ 1 Baths ⋅ 5112828 MLS

Sometimes, just the right amount of space is exactly what you need. Set on two pleasant acres in Chester, this tidy 2-bedroom, ¾-bath home offers comfortable, efficient one-level living with a practical layout that makes everyday life easy. Inside, the home is bright and well cared for, with a modern kitchen, comfortable living space, two nicely sized bedrooms, laundry, and the convenience of everything on one floor. Propane heat keeps things simple and efficient, while the manageable footprint means less house to maintain and more time to enjoy Vermont. Outside, the level lawn provides plenty of usable space for gardening, pets, a fire pit, or simply relaxing outdoors without taking on an overwhelming property. A detached two-car garage offers excellent parking, storage, and room for the tools and gear that come with Vermont living. Whether you're looking for a first home, ready to simplify, or searching for a comfortable retirement property with minimal stairs and manageable upkeep, this Chester home checks a lot of boxes. Simple, practical, and easy to maintain, it is a home that makes perfect sense.

547 Andover Rd, Chester

$209,500

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

5097621 MLS

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

3668 Vt Route 103 N, Chester

$209,500

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

4 Beds ⋅ 3 Baths ⋅ 5097620 MLS

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

3668 Vt Route 103 N, 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

$168,000

Looking for mountain views and privacy, but wanting to be close enough to walk to downtown Chester? This beautiful surveyed lot has all that and much, much more! The seller has already cleared for the perfect house site, roughed in a driveway for easy access, and secured a Wastewater Design/Permit and Potable Water Supply permit -doing so much of the hard work so you can come in and install them and build the house of your dreams! Easy access of Interstate 91, room for animals, close to many mountains for skiing and snowboarding, snowmobiling, nearby hiking, easy drive or walk to downtown Chester's shops and amenities. Call to schedule your showing, bring your imagination and dreams while you walk this remarkable property!

5113361 MLS

Looking for mountain views and privacy, but wanting to be close enough to walk to downtown Chester? This beautiful surveyed lot has all that and much, much more! The seller has already cleared for the perfect house site, roughed in a driveway for easy access, and secured a Wastewater Design/Permit and Potable Water Supply permit -doing so much of the hard work so you can come in and install them and build the house of your dreams! Easy access of Interstate 91, room for animals, close to many mountains for skiing and snowboarding, snowmobiling, nearby hiking, easy drive or walk to downtown Chester's shops and amenities. Call to schedule your showing, bring your imagination and dreams while you walk this remarkable property!

377 Coach Rd, Chester

$149,000

Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont Wastewater Permit for a five-bedroom residence. With zoning requiring a minimum of three acres and 200 feet of road frontage, the property presents an excellent opportunity for subdivision. One building site has already been identified as suitable, while the extensive road frontage provides the flexibility to explore additional potential home sites. A rare opportunity to create a private estate, family compound, or thoughtfully planned development in a quintessential Vermont setting. The location makes it easy to participate in all of the Chester Community events. Just a short drive to Okemo Mountain Resort for all of your outdoor adventures.

5102503 MLS

Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont Wastewater Permit for a five-bedroom residence. With zoning requiring a minimum of three acres and 200 feet of road frontage, the property presents an excellent opportunity for subdivision. One building site has already been identified as suitable, while the extensive road frontage provides the flexibility to explore additional potential home sites. A rare opportunity to create a private estate, family compound, or thoughtfully planned development in a quintessential Vermont setting. The location makes it easy to participate in all of the Chester Community events. Just a short drive to Okemo Mountain Resort for all of your outdoor adventures.

Trebo Rd, Chester

$99,999

This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn, ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifully, creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.

5082636 MLS

This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn, ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifully, creating a prime site to build your dream home. State wastewater permit WW-2-4040-1 approved for a 5-bedroom home.

508 Mattson Rd, Chester

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