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If you're looking for a tranquil, move-in-ready 3-bedroom home nestled on 3.77 wooded acres, your search is over! Enjoy the peaceful surroundings from the brand-new 12' x 16' deck the perfect spot to relax with a book and take in nature. This beautifully remodeled home offers worry-free living with a new roof, new windows, a stunning new kitchen featuring leathered granite countertops, soft-close cabinetry, and stainless steel appliances, plus two completely renovated bathrooms. Thoughtfully updated throughout, this property combines modern comforts with the privacy and serenity of a wooded setting. Don't miss the opportunity to own this turnkey retreat that feels miles away from it all while still providing the conveniences of home. Agent Interest

3 Beds ⋅ 2 Baths ⋅ 5092425 MLS

If you're looking for a tranquil, move-in-ready 3-bedroom home nestled on 3.77 wooded acres, your search is over! Enjoy the peaceful surroundings from the brand-new 12' x 16' deck the perfect spot to relax with a book and take in nature. This beautifully remodeled home offers worry-free living with a new roof, new windows, a stunning new kitchen featuring leathered granite countertops, soft-close cabinetry, and stainless steel appliances, plus two completely renovated bathrooms. Thoughtfully updated throughout, this property combines modern comforts with the privacy and serenity of a wooded setting. Don't miss the opportunity to own this turnkey retreat that feels miles away from it all while still providing the conveniences of home. Agent Interest

51 Halls Village Rd, Chester

$599,900

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

2 Beds ⋅ 3 Baths ⋅ 5077914 MLS

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

32 Gypsum Ln Unit 30, Chester

$599,900

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

2 Beds ⋅ 3 Baths ⋅ 5077910 MLS

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

34 Gypsum Ln Unit 31, Chester

$579,900

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The basement has tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion July 2026. Photos are from previously built unit.

2 Beds ⋅ 3 Baths ⋅ 5100454 MLS

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The basement has tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion July 2026. Photos are from previously built unit.

16 Gypsum Ln Unit 26, Chester

$569,900

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

2 Beds ⋅ 3 Baths ⋅ 5107531 MLS

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

4 Gypsum Ln Unit 24, Chester

$569,900

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

2 Beds ⋅ 3 Baths ⋅ 5107530 MLS

WOW check out Southwood's Phase 4, this Brand NEW Gorgeous Townhouse is The Best value in Rockingham County. The home Features 2 potential primary bedrooms. The 1st Floor primary Bedroom with an En suite. The gorgeous Kitchen has an Island with Granite Countertops and Stainless-Steel appliances that is sure to please and connects to a Generous sized Trex Deck with woods out back. The large Living room has hardwood floors and is open to the kitchen with Gleaming hardwood floors, 1st floor, laundry and half bath complete the first level. The 2nd Floor features a Huge Bedroom with an Ensuite for a second potential primary bedroom a massive walk-in closet, another BONUS room that is Huge which can be an office or study etc. There is also another HUGE space that can be storage or convert to more living space. The walkout basement has a day light window with tons of storage and ready to be finished for more living space. Central AC will keep you cool in the summer. Expected completion May 2026. Photos are from previously built unit.

12 Gypsum Ln Unit 25, Chester

$569,000

Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive. The heartbeat of the home comes from a bright and inviting great room that opens through sliding doors to an expansive deck where mornings begin with coffee and birdsong, and evenings end with the sound of rushing water under the stars. The flowing layout offers spaces that adapt beautifully to modern living — a dedicated office for remote work, room for a home gym, studio, creative retreat, media lounge, or whatever your lifestyle calls for next. The dining room is ready for gatherings both large and small, while the attached 2-bay garage and generous outdoor space make everyday living feel effortless. Whether you're hosting friends, growing a garden, creating art, working from home, or simply looking for a peaceful place to recharge, this property offers the flexibility to make it your own. Private yet convenient, peaceful yet connected — this home delivers a lifestyle that’s increasingly hard to find.

3 Beds ⋅ 2 Baths ⋅ 5084462 MLS

Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive. The heartbeat of the home comes from a bright and inviting great room that opens through sliding doors to an expansive deck where mornings begin with coffee and birdsong, and evenings end with the sound of rushing water under the stars. The flowing layout offers spaces that adapt beautifully to modern living — a dedicated office for remote work, room for a home gym, studio, creative retreat, media lounge, or whatever your lifestyle calls for next. The dining room is ready for gatherings both large and small, while the attached 2-bay garage and generous outdoor space make everyday living feel effortless. Whether you're hosting friends, growing a garden, creating art, working from home, or simply looking for a peaceful place to recharge, this property offers the flexibility to make it your own. Private yet convenient, peaceful yet connected — this home delivers a lifestyle that’s increasingly hard to find.

147 Pleasant View Ln, Chester

$565,000

OPEN HOUSE SUNDAY 5/17 2-4pm!! This antique beauty has been completely restored and sits on an absolutely heavenly piece of property. Wide pine floors will be the showcase of your living space anchored by the brick hearth and wood stove insert. You have a separate dining space, although that's flexible to use as you choose. The kitchen sits at the back of the home and is equipped with a brand new dishwasher, electric range, newer fridge and room for a stackable washer/dryer-the hook-up is already done! You'll appreciate the luxury vinyl tile and especially drool over the custom pantry! The first of 3 full bathrooms conveniently located the kitchen. On this level you have more great space that could be a dreamy primary master ensuite. This space has a separate entry leading out to the back deck; perfect potential for an in-law here-equipped with a 3/4 bathroom. Head up the newly treaded staircase for 3 more bedrooms and another full bath! ALL with brand new LVP flooring. This charmer has virtually all new plumbing, a new boiler, and of course the entire home has been freshy painted. TWO driveways and several choices for entry making grocery shopping a breeze. Don't forget the detached garage for your car, toys or whatever you decide!

4 Beds ⋅ 3 Baths ⋅ 5086317 MLS

OPEN HOUSE SUNDAY 5/17 2-4pm!! This antique beauty has been completely restored and sits on an absolutely heavenly piece of property. Wide pine floors will be the showcase of your living space anchored by the brick hearth and wood stove insert. You have a separate dining space, although that's flexible to use as you choose. The kitchen sits at the back of the home and is equipped with a brand new dishwasher, electric range, newer fridge and room for a stackable washer/dryer-the hook-up is already done! You'll appreciate the luxury vinyl tile and especially drool over the custom pantry! The first of 3 full bathrooms conveniently located the kitchen. On this level you have more great space that could be a dreamy primary master ensuite. This space has a separate entry leading out to the back deck; perfect potential for an in-law here-equipped with a 3/4 bathroom. Head up the newly treaded staircase for 3 more bedrooms and another full bath! ALL with brand new LVP flooring. This charmer has virtually all new plumbing, a new boiler, and of course the entire home has been freshy painted. TWO driveways and several choices for entry making grocery shopping a breeze. Don't forget the detached garage for your car, toys or whatever you decide!

17 Derry Rd, Chester

$563,000

Charming Renovated Farmhouse in the Heart of Chester This beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway. Inside, enjoy a spacious kitchen with custom pantry shelving, a convenient first-floor laundry room and cozy mudroom. Two main-floor bedrooms provide flexible living options. The second level has a cozy 3rd bedroom and 3/4 bath plus the luxurious primary suite boasting a brand-new custom bathroom with a soaking tub, oversized steam shower, walk-in closet, and a peaceful sitting area. Outdoor living is equally inviting, with a covered wrap-around porch, screened porch opening to a stone patio, and a tranquil Zen garden. A vegetable garden awaits your green thumb, and the small attached barn offers extra storage or workshop potential. A newly added one-car garage and whole-house generator completes the package. Conveniently situated within 15 minutes of Okemo or Magic Mountain, and under 30 minutes to Bromley and Stratton—this is Vermont living at its best!

4 Beds ⋅ 3 Baths ⋅ 5054818 MLS

Charming Renovated Farmhouse in the Heart of Chester This beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway. Inside, enjoy a spacious kitchen with custom pantry shelving, a convenient first-floor laundry room and cozy mudroom. Two main-floor bedrooms provide flexible living options. The second level has a cozy 3rd bedroom and 3/4 bath plus the luxurious primary suite boasting a brand-new custom bathroom with a soaking tub, oversized steam shower, walk-in closet, and a peaceful sitting area. Outdoor living is equally inviting, with a covered wrap-around porch, screened porch opening to a stone patio, and a tranquil Zen garden. A vegetable garden awaits your green thumb, and the small attached barn offers extra storage or workshop potential. A newly added one-car garage and whole-house generator completes the package. Conveniently situated within 15 minutes of Okemo or Magic Mountain, and under 30 minutes to Bromley and Stratton—this is Vermont living at its best!

95 Church St, Chester

$542,500

Own the lifestyle you want! An absolutely amazing opportunity to live in this beautifully updated one-level home in the desirable town of Chester, located within the sought-after Pinkerton Academy School District, where turnkey living meets privacy, space, and versatility. Set on just under 2 acres of flat, usable land, this property offers the perfect blend of modern updates and functional living. The stunning kitchen features brand-new quartz countertops, all-new cabinetry, stainless steel appliances, and sleek under-cabinet lighting, creating a stylish and highly functional space at the heart of the home. The living room impresses with soaring cathedral ceilings, delivering an open, airy feel filled with natural light. Fresh paint and updated lighting flow seamlessly throughout, complementing two spacious bedrooms with ample closet space, plus a flexible bonus room ideal for a third bedroom, home office, or guest space. Significant exterior upgrades include all-new siding, a brand-new roof, and stylish black windows and doors on the home, along with new siding and a new roof on the barn, creating a cohesive modern exterior and offering peace of mind for years to come. Outside, enjoy newly installed pavers leading to the entrance and a brand new back deck overlooking your private backyard retreat. The detached barn or garage offers excellent storage, workshop, or hobby space, while the greenhouse, equipped with power and heat, is perfect for year-round gardening or homesteading. A rare combination of land, updates, and versatility, this is one you will not want to miss. Showings begin at the open houses Saturday, 4/18, & Sunday, 4/19, from 11:00AM to 1:00PM. Properties like this in Chester with this level of updates and land rarely come to market.

2 Beds ⋅ 1 Baths ⋅ 5083923 MLS

Own the lifestyle you want! An absolutely amazing opportunity to live in this beautifully updated one-level home in the desirable town of Chester, located within the sought-after Pinkerton Academy School District, where turnkey living meets privacy, space, and versatility. Set on just under 2 acres of flat, usable land, this property offers the perfect blend of modern updates and functional living. The stunning kitchen features brand-new quartz countertops, all-new cabinetry, stainless steel appliances, and sleek under-cabinet lighting, creating a stylish and highly functional space at the heart of the home. The living room impresses with soaring cathedral ceilings, delivering an open, airy feel filled with natural light. Fresh paint and updated lighting flow seamlessly throughout, complementing two spacious bedrooms with ample closet space, plus a flexible bonus room ideal for a third bedroom, home office, or guest space. Significant exterior upgrades include all-new siding, a brand-new roof, and stylish black windows and doors on the home, along with new siding and a new roof on the barn, creating a cohesive modern exterior and offering peace of mind for years to come. Outside, enjoy newly installed pavers leading to the entrance and a brand new back deck overlooking your private backyard retreat. The detached barn or garage offers excellent storage, workshop, or hobby space, while the greenhouse, equipped with power and heat, is perfect for year-round gardening or homesteading. A rare combination of land, updates, and versatility, this is one you will not want to miss. Showings begin at the open houses Saturday, 4/18, & Sunday, 4/19, from 11:00AM to 1:00PM. Properties like this in Chester with this level of updates and land rarely come to market.

211 Sandown Rd, Chester

$535,000

OPEN HOUSE CANCELED - In-Law / Multi-Generational Style Setup. You have a bedroom, bath and sitting area over the garage and at the other end of the house between a family room, kitchen, porch and living room are 3 more bedrooms and a bathroom with laundry. DON'T MISS THIS RARE OPPORTUNITY! Discover this hard-to-find Ranch-style home set on two beautiful, level acres with exceptional backyard privacy in the heart of Chester's highly sought-after equestrian community. Properties like this don't come along often! This spacious 4-bedroom, 2-bath home offers desirable southern exposure across the backyard, creating the perfect setting to relax on the deck or porch while enjoying stunning sunsets. Inside, you'll find a large living room featuring a classic brick-hearth wood-burning fireplace and expansive hardwood floors that add warmth and timeless appeal. The main level includes three generously sized bedrooms with hardwood flooring, a full bath, and the convenience of first-floor laundry. The kitchen is well-appointed with stainless steel appliances, granite countertops, two pantry cabinets, and stylish recessed and pendant lighting. A bonus family room leads to the attached two-car garage, while the private primary suite above the garage features a sitting area, creating the perfect retreat at the end of the day. The full basement offers excellent potential for additional finished living space, giving you room to grow. Outside, the expansive level lot provides endless possibilities for entertaining, gardening, or enjoying the peaceful surroundings. The pool will require a new liner and possibly a new filter. This house needs some love and being sold in the present condition. AGENTS & BUYERS to do their own Due Diligence to verify all listing information. Room sizes are for reference only; not guaranteed. Some photos are digitally decluttered, altered and virtually staged.

4 Beds ⋅ 2 Baths ⋅ 5096954 MLS

OPEN HOUSE CANCELED - In-Law / Multi-Generational Style Setup. You have a bedroom, bath and sitting area over the garage and at the other end of the house between a family room, kitchen, porch and living room are 3 more bedrooms and a bathroom with laundry. DON'T MISS THIS RARE OPPORTUNITY! Discover this hard-to-find Ranch-style home set on two beautiful, level acres with exceptional backyard privacy in the heart of Chester's highly sought-after equestrian community. Properties like this don't come along often! This spacious 4-bedroom, 2-bath home offers desirable southern exposure across the backyard, creating the perfect setting to relax on the deck or porch while enjoying stunning sunsets. Inside, you'll find a large living room featuring a classic brick-hearth wood-burning fireplace and expansive hardwood floors that add warmth and timeless appeal. The main level includes three generously sized bedrooms with hardwood flooring, a full bath, and the convenience of first-floor laundry. The kitchen is well-appointed with stainless steel appliances, granite countertops, two pantry cabinets, and stylish recessed and pendant lighting. A bonus family room leads to the attached two-car garage, while the private primary suite above the garage features a sitting area, creating the perfect retreat at the end of the day. The full basement offers excellent potential for additional finished living space, giving you room to grow. Outside, the expansive level lot provides endless possibilities for entertaining, gardening, or enjoying the peaceful surroundings. The pool will require a new liner and possibly a new filter. This house needs some love and being sold in the present condition. AGENTS & BUYERS to do their own Due Diligence to verify all listing information. Room sizes are for reference only; not guaranteed. Some photos are digitally decluttered, altered and virtually staged.

224 Haverhill Rd, Chester

$520,000

If you’re looking for a home you can move into comfortably while adding your own personal touches over time, this property is worth a look. Set on 3.20 private acres, this 3-bedroom, 2-bath Raised Ranch offers a peaceful setting with plenty of room to make it your own. It’s a great opportunity for a first-time homebuyer looking for a place to start, a buyer ready to downsize, or anyone seeking privacy and space without giving up convenience. The main level features a kitchen, dining area, and living room, creating a comfortable layout for everyday living and entertaining. Down the hall, you’ll find a full bathroom, a primary bedroom with a convenient 3/4 bath, and two additional bedrooms. Just off the dining area, the screened-in deck offers a relaxing spot to enjoy the peaceful, private surroundings. The lower level adds even more versatility with a generous bonus room that could be used as a game room, home office, playroom, or whatever best fits your lifestyle. This level also includes a large utility room and a two-car garage, providing plenty of space for storage, projects, and everyday convenience. Easy access to Route 102 and Route 101 in Raymond. The property also offers access to the highly desirable Pinkerton Academy. Whether you’re purchasing your first home, looking to simplify and downsize, or searching for a property where you can settle in and make it your own, this home offers a great combination of privacy, flexibility, and convenience. Professional pictures coming. Showings to begin at Open House on Saturday 8/15/26 ~ 11:00 - 12:30

3 Beds ⋅ 2 Baths ⋅ 5104497 MLS

If you’re looking for a home you can move into comfortably while adding your own personal touches over time, this property is worth a look. Set on 3.20 private acres, this 3-bedroom, 2-bath Raised Ranch offers a peaceful setting with plenty of room to make it your own. It’s a great opportunity for a first-time homebuyer looking for a place to start, a buyer ready to downsize, or anyone seeking privacy and space without giving up convenience. The main level features a kitchen, dining area, and living room, creating a comfortable layout for everyday living and entertaining. Down the hall, you’ll find a full bathroom, a primary bedroom with a convenient 3/4 bath, and two additional bedrooms. Just off the dining area, the screened-in deck offers a relaxing spot to enjoy the peaceful, private surroundings. The lower level adds even more versatility with a generous bonus room that could be used as a game room, home office, playroom, or whatever best fits your lifestyle. This level also includes a large utility room and a two-car garage, providing plenty of space for storage, projects, and everyday convenience. Easy access to Route 102 and Route 101 in Raymond. The property also offers access to the highly desirable Pinkerton Academy. Whether you’re purchasing your first home, looking to simplify and downsize, or searching for a property where you can settle in and make it your own, this home offers a great combination of privacy, flexibility, and convenience. Professional pictures coming. Showings to begin at Open House on Saturday 8/15/26 ~ 11:00 - 12:30

42 Great Oak Dr, Chester

$515,000

Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous room off the kitchen easily accommodates larger meals and celebrations. Original wood floors, exposed beams, and durable early craftsmanship add character throughout. A separate rental unit, currently occupied, provides steady income or flexible use for guests, family, or workspace. The barn offers storage, workshop potential, or agricultural use, expanding what the property can support. Chester’s shops and everyday conveniences are close by, and skiing, rivers, and trails are within easy reach. Okemo is just minutes away, with Stratton, Magic, and Bromley all within a short drive of 20-30 minutes. Several AT access point within similar distance. The Okemo Valley is on your doorstep, and it's magical! This is a historic home ready for its next chapter—solid, adaptable, and full of possibility. Come See Today!!

5 Beds ⋅ 5 Baths ⋅ 5068855 MLS

Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous room off the kitchen easily accommodates larger meals and celebrations. Original wood floors, exposed beams, and durable early craftsmanship add character throughout. A separate rental unit, currently occupied, provides steady income or flexible use for guests, family, or workspace. The barn offers storage, workshop potential, or agricultural use, expanding what the property can support. Chester’s shops and everyday conveniences are close by, and skiing, rivers, and trails are within easy reach. Okemo is just minutes away, with Stratton, Magic, and Bromley all within a short drive of 20-30 minutes. Several AT access point within similar distance. The Okemo Valley is on your doorstep, and it's magical! This is a historic home ready for its next chapter—solid, adaptable, and full of possibility. Come See Today!!

514 First Ave, Chester

$500,000

Storybook charm meets thoughtful modern updates in the heart of Chester! From the moment you arrive, you'll feel the character and the warmth of or this charming 3 bedroom, 1.5 bath cape. Thoughtfully remodeled through the years, the home has been lovingly updated while preserving the original charm and details that make it feel truly special. The inviting first floor offers a comfortable flow for everyday living, including a first floor primary bedroom and convenient first-floor laundry. Throughout the home, you'll find a wonderful balance of timeless character and practical updates, creating a home that feels both classic and comfortable. And then there's the yard! Level, spacious, and incredibly usable, it provides the perfect backdrop for summer gatherings, lawn games, entertaining, gardening, or simply enjoying a quiet afternoon outdoors. There's room here to make memories. Located in Chester, NH, a town known for its quintessential New England charm this home offers a wonderful sense of community while still being conveniently positioned for commuters. It's the kind of place that feels like home the moment you arrive-and a property you'll be proud to call your own and the perfect place to start your next chapter.

3 Beds ⋅ 2 Baths ⋅ 5107281 MLS

Storybook charm meets thoughtful modern updates in the heart of Chester! From the moment you arrive, you'll feel the character and the warmth of or this charming 3 bedroom, 1.5 bath cape. Thoughtfully remodeled through the years, the home has been lovingly updated while preserving the original charm and details that make it feel truly special. The inviting first floor offers a comfortable flow for everyday living, including a first floor primary bedroom and convenient first-floor laundry. Throughout the home, you'll find a wonderful balance of timeless character and practical updates, creating a home that feels both classic and comfortable. And then there's the yard! Level, spacious, and incredibly usable, it provides the perfect backdrop for summer gatherings, lawn games, entertaining, gardening, or simply enjoying a quiet afternoon outdoors. There's room here to make memories. Located in Chester, NH, a town known for its quintessential New England charm this home offers a wonderful sense of community while still being conveniently positioned for commuters. It's the kind of place that feels like home the moment you arrive-and a property you'll be proud to call your own and the perfect place to start your next chapter.

40 Old Sandown Rd, Chester

$500,000

Welcome to 79 Haverhill Road in the charming town of Chester, New Hampshire—a property that perfectly blends New England character with everyday comfort. Set on a spacious lot surrounded by natural beauty, this home offers a peaceful retreat while still being conveniently located near local amenities and major routes. Step inside to find a warm and inviting interior featuring an open floor plan with an abundance of natural light, functional living spaces, and timeless design elements that make you feel right at home. The kitchen provides ample cabinetry and workspace with beautiful granite counters, stainless appliances and tile backsplash and island ideal for both daily living and entertaining. Comfortable living areas create the perfect setting for relaxing evenings or gathering with family and friends. Generously sized bedrooms offer flexibility for a variety of needs, whether you're looking for space to grow, work from home, or host guests. Outside, enjoy a private yard with plenty of room for outdoor activities, gardening, or simply soaking in the tranquility of the surrounding landscape. Whether you're sipping your morning coffee or enjoying a summer evening, this property offers the kind of outdoor space that makes New Hampshire living so special. Located in the desirable town of Chester, known for its historic charm and community feel, this home is a wonderful opportunity to enjoy a quieter lifestyle without sacrificing convenience. Home also features a newer roof that was installed in 2024 and the entire house was fully renovated within the last six years to include updated plumbing and electrical. All of this and Part of the Pinkerton Academy School District. Don’t miss your chance to make this inviting property your own. Schedule your showing today!

2 Beds ⋅ 2 Baths ⋅ 5081598 MLS

Welcome to 79 Haverhill Road in the charming town of Chester, New Hampshire—a property that perfectly blends New England character with everyday comfort. Set on a spacious lot surrounded by natural beauty, this home offers a peaceful retreat while still being conveniently located near local amenities and major routes. Step inside to find a warm and inviting interior featuring an open floor plan with an abundance of natural light, functional living spaces, and timeless design elements that make you feel right at home. The kitchen provides ample cabinetry and workspace with beautiful granite counters, stainless appliances and tile backsplash and island ideal for both daily living and entertaining. Comfortable living areas create the perfect setting for relaxing evenings or gathering with family and friends. Generously sized bedrooms offer flexibility for a variety of needs, whether you're looking for space to grow, work from home, or host guests. Outside, enjoy a private yard with plenty of room for outdoor activities, gardening, or simply soaking in the tranquility of the surrounding landscape. Whether you're sipping your morning coffee or enjoying a summer evening, this property offers the kind of outdoor space that makes New Hampshire living so special. Located in the desirable town of Chester, known for its historic charm and community feel, this home is a wonderful opportunity to enjoy a quieter lifestyle without sacrificing convenience. Home also features a newer roof that was installed in 2024 and the entire house was fully renovated within the last six years to include updated plumbing and electrical. All of this and Part of the Pinkerton Academy School District. Don’t miss your chance to make this inviting property your own. Schedule your showing today!

79 Haverhill Rd, Chester

$499,900

STAY-CATION LIVING IS CALLING. Nestled on a gorgeous, private, flat acre in Chester, this home delivers the outdoor lifestyle you've been dreaming of. Pull into the paved driveway and you'll already see it - the lush landscaping, the natural shade, and a backyard that's pure paradise. Three sheds plus a detached garage with partially finished bonus space give you room for all your gear and then some. Step inside through the foyer and you're greeted by warm wood floors and natural light throughout. The open concept kitchen features an island, updated cabinets, and a gas range - ideal for cooking after a long day outside. It opens to a cozy family room with a wood fireplace, one of TWO fireplaces in the home. Heat with propane, wood or electric baseboard. The half bath and laundry are conveniently tucked on the main level. Upstairs, the living room and dining area offer flexible everyday space, and the top floor holds the primary suite with a walk-in closet, a second bedroom with its own large closet, and a completely renovated full bath for both bedrooms to share. The middle floor is designed for a three-bedroom configuration - easy to convert back. Now for the MAIN EVENT: the backyard. Above-ground pool. Hot tub. Garden space. Deck. This is where summers happen. NEW SEPTIC & LEACH FIELD and 2-year-old heating system mean the big-ticket items are already done. Pinkerton Academy district. Book your tour today!

3 Beds ⋅ 2 Baths ⋅ 5096706 MLS

STAY-CATION LIVING IS CALLING. Nestled on a gorgeous, private, flat acre in Chester, this home delivers the outdoor lifestyle you've been dreaming of. Pull into the paved driveway and you'll already see it - the lush landscaping, the natural shade, and a backyard that's pure paradise. Three sheds plus a detached garage with partially finished bonus space give you room for all your gear and then some. Step inside through the foyer and you're greeted by warm wood floors and natural light throughout. The open concept kitchen features an island, updated cabinets, and a gas range - ideal for cooking after a long day outside. It opens to a cozy family room with a wood fireplace, one of TWO fireplaces in the home. Heat with propane, wood or electric baseboard. The half bath and laundry are conveniently tucked on the main level. Upstairs, the living room and dining area offer flexible everyday space, and the top floor holds the primary suite with a walk-in closet, a second bedroom with its own large closet, and a completely renovated full bath for both bedrooms to share. The middle floor is designed for a three-bedroom configuration - easy to convert back. Now for the MAIN EVENT: the backyard. Above-ground pool. Hot tub. Garden space. Deck. This is where summers happen. NEW SEPTIC & LEACH FIELD and 2-year-old heating system mean the big-ticket items are already done. Pinkerton Academy district. Book your tour today!

111 Shepard Home Rd, Chester

$495,000

"HIGHEST AND BEST OFFERS DUE WEDNESDAY 3:00 PM" Don’t miss this unique and versatile two-family ranch in desirable Chester, New Hampshire! Conveniently located with easy access to Route 101, this property offers incredible potential for owner occupants, investors, multi-generational living, or possible in home business use. The property offers convenient first floor ranch style living in both units, which have been freshly painted, with some flooring updates already completed, creating a move in ready opportunity with plenty of room to continue building equity through additional updates and improvements over time. The lower level adds even more flexibility, featuring several semi-finished rooms, a full bath, wet bar, cabinetry, and bonus space ideal for recreation, office space, workshop areas, storage, hobbies, or extended use. With ample parking and a functional layout, the possibilities are extensive. The lower level also has potential to be incorporated into one of the units by adding a stairway from the first floor, creating additional living or functional space. Live in one unit while renting the other to help offset your mortgage, create an income producing investment property, or customize the space to fit your needs. Properties with this much flexibility, usable space, and future potential are difficult to find at this price point. Set on over an acre with a large deck and peaceful surroundings, the property offers privacy, usable space, and a scenic country setting. Offered at $499,900.

5087407 MLS

"HIGHEST AND BEST OFFERS DUE WEDNESDAY 3:00 PM" Don’t miss this unique and versatile two-family ranch in desirable Chester, New Hampshire! Conveniently located with easy access to Route 101, this property offers incredible potential for owner occupants, investors, multi-generational living, or possible in home business use. The property offers convenient first floor ranch style living in both units, which have been freshly painted, with some flooring updates already completed, creating a move in ready opportunity with plenty of room to continue building equity through additional updates and improvements over time. The lower level adds even more flexibility, featuring several semi-finished rooms, a full bath, wet bar, cabinetry, and bonus space ideal for recreation, office space, workshop areas, storage, hobbies, or extended use. With ample parking and a functional layout, the possibilities are extensive. The lower level also has potential to be incorporated into one of the units by adding a stairway from the first floor, creating additional living or functional space. Live in one unit while renting the other to help offset your mortgage, create an income producing investment property, or customize the space to fit your needs. Properties with this much flexibility, usable space, and future potential are difficult to find at this price point. Set on over an acre with a large deck and peaceful surroundings, the property offers privacy, usable space, and a scenic country setting. Offered at $499,900.

414 Fremont Rd, Chester

$480,000

This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached garage. This light-filled home with two floors of living (plus a multi-room lower-level walkout ready to finish) has great open space on the main level. The kitchen with updated granite counters is open to the dining area which has a sliding door to the large back deck. This is the perfect space to have dinner overlooking the landscaped back yard. Try your green thumb in the vegetable garden that is ready for planting. The living room is also connected to the dining area making this space perfect for friends and family to gather. A convenient bedroom and bathroom complete this level. Upstairs are two generous bedrooms, a bonus room for a home office or more plus space above the garage that is currently being used as an amazing walk-in closet. Come and take a look at this low-maintenance home in a park-like setting with berry bushes, fruit trees, a gazebo, and a combination garden and wood shed. The stone firepit could be a favorite spot for relaxing by the fire after a day on the slopes. There is a third bay workshop next to the attached garage and an additional detached garage that has a vent pipe for a wood stove and can be of multiple uses. This property will check boxes that you didn't even know you had!

3 Beds ⋅ 2 Baths ⋅ 5095371 MLS

This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached garage. This light-filled home with two floors of living (plus a multi-room lower-level walkout ready to finish) has great open space on the main level. The kitchen with updated granite counters is open to the dining area which has a sliding door to the large back deck. This is the perfect space to have dinner overlooking the landscaped back yard. Try your green thumb in the vegetable garden that is ready for planting. The living room is also connected to the dining area making this space perfect for friends and family to gather. A convenient bedroom and bathroom complete this level. Upstairs are two generous bedrooms, a bonus room for a home office or more plus space above the garage that is currently being used as an amazing walk-in closet. Come and take a look at this low-maintenance home in a park-like setting with berry bushes, fruit trees, a gazebo, and a combination garden and wood shed. The stone firepit could be a favorite spot for relaxing by the fire after a day on the slopes. There is a third bay workshop next to the attached garage and an additional detached garage that has a vent pipe for a wood stove and can be of multiple uses. This property will check boxes that you didn't even know you had!

3078 Vt Route 10, Chester

$460,000

MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The rooms are nicely sized and in close proximity to bathrooms. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has an en suite with a full bathroom and lots of closet space! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won’t want to miss on your home buying adventure! Truly a stunning property with so much to offer!

3 Beds ⋅ 2 Baths ⋅ 5085214 MLS

MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The rooms are nicely sized and in close proximity to bathrooms. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has an en suite with a full bathroom and lots of closet space! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won’t want to miss on your home buying adventure! Truly a stunning property with so much to offer!

547 Williams Rd, Chester

$449,900

Just in time for summer, this elegant and spacious townhouse offers the perfect blend of comfort and style. Step inside to an updated kitchen featuring sleek granite countertops, quality cabinetry, and stainless steel appliances. The space is complete with a charming dining nook—and the perfectly fitted table and chair set are included! Relax in the inviting living area anchored by a lovely gas fireplace, where the mounted TV above the mantle stays for the new owners to enjoy. This home is designed for flexibility, offering true first-floor living potential. The main level features a large bedroom with soaring cathedral ceilings, located just steps from a 3/4 bath and convenient first-floor laundry. Upstairs, you’ll find a second spacious bedroom with a full bath and a sun-drenched office nook illuminated by bright windows and skylights. The walk-out lower level adds incredible versatility with a partially finished space—currently used as a third bedroom, it could easily serve as a home gym or media room. The unfinished side provides massive storage for all your seasonal collections. Outside, the beautiful in-ground community pool makes every day feel like a vacation, while the attached garage offers even more storage and convenience. Ideally situated in a quiet and peaceful setting, this home puts you right near the best of local recreation. You are just a short distance from Wason Pond Conservation and Rec Area, Pawtuckaway State Park, and Lake Massabesic. With the highway close by, you can enjoy a tranquil lifestyle without sacrificing an easy commute. Don’t miss out—be settled in just in time for pool season! Open House 5/16 1-3PM & 5/17 11AM-1PM.

2 Beds ⋅ 2 Baths ⋅ 5087750 MLS

Just in time for summer, this elegant and spacious townhouse offers the perfect blend of comfort and style. Step inside to an updated kitchen featuring sleek granite countertops, quality cabinetry, and stainless steel appliances. The space is complete with a charming dining nook—and the perfectly fitted table and chair set are included! Relax in the inviting living area anchored by a lovely gas fireplace, where the mounted TV above the mantle stays for the new owners to enjoy. This home is designed for flexibility, offering true first-floor living potential. The main level features a large bedroom with soaring cathedral ceilings, located just steps from a 3/4 bath and convenient first-floor laundry. Upstairs, you’ll find a second spacious bedroom with a full bath and a sun-drenched office nook illuminated by bright windows and skylights. The walk-out lower level adds incredible versatility with a partially finished space—currently used as a third bedroom, it could easily serve as a home gym or media room. The unfinished side provides massive storage for all your seasonal collections. Outside, the beautiful in-ground community pool makes every day feel like a vacation, while the attached garage offers even more storage and convenience. Ideally situated in a quiet and peaceful setting, this home puts you right near the best of local recreation. You are just a short distance from Wason Pond Conservation and Rec Area, Pawtuckaway State Park, and Lake Massabesic. With the highway close by, you can enjoy a tranquil lifestyle without sacrificing an easy commute. Don’t miss out—be settled in just in time for pool season! Open House 5/16 1-3PM & 5/17 11AM-1PM.

21 Villager Rd, Chester

$445,000

Welcome to this like-new home in the sought-after Villages at Chester, a non-age-restricted community offering flexibility for a variety of lifestyles. This beautifully updated condo features a one-car garage, a first-floor bedroom with an attached bath, a spacious kitchen and dining area, and a living room with a vaulted ceiling that adds warmth and openness to the space. Upstairs, you’ll find a loft, a private ensuite bedroom, and a walk-in closet. Recent improvements include all new carpeting, LVL flooring, fresh interior paint throughout, new toilets, and newly painted kitchen cabinets. Step out onto the back deck and enjoy peaceful views overlooking The Pond, one of the best locations in the neighborhood. Located within highly rated public school systems, including Chester Academy and Pinkerton Academy, this home offers both comfort and convenience in a desirable setting. This home truly feels like new and is ready for its next owner to enjoy.

2 Beds ⋅ 2 Baths ⋅ 5083016 MLS

Welcome to this like-new home in the sought-after Villages at Chester, a non-age-restricted community offering flexibility for a variety of lifestyles. This beautifully updated condo features a one-car garage, a first-floor bedroom with an attached bath, a spacious kitchen and dining area, and a living room with a vaulted ceiling that adds warmth and openness to the space. Upstairs, you’ll find a loft, a private ensuite bedroom, and a walk-in closet. Recent improvements include all new carpeting, LVL flooring, fresh interior paint throughout, new toilets, and newly painted kitchen cabinets. Step out onto the back deck and enjoy peaceful views overlooking The Pond, one of the best locations in the neighborhood. Located within highly rated public school systems, including Chester Academy and Pinkerton Academy, this home offers both comfort and convenience in a desirable setting. This home truly feels like new and is ready for its next owner to enjoy.

205 Villager Rd, Chester

$432,500

You pull up to a quiet cul-de-sac, the noise of the world already fading behind you. A COVERED PORCH waits at the front door, the kind you actually use. Step inside and you'll know: this is the one. Nestled in Chester's Shaker Heights Estates, this meticulous MOVE-IN READY townhouse checks every box and then some. Pride of ownership shines through every room. The open main level welcomes you with gleaming hardwood floors and NATURAL LIGHT pouring in from every angle. The eat-in kitchen, a generous 17x15, features stainless steel appliances and flows right into the dining area, making everyday meals and weekend entertaining equally effortless. The living room is HUGE at 24x16 with a private DECK. Step outside, breathe in the wooded views, and make it your morning coffee spot or evening wind-down zone. A half bath and FIRST-FLOOR LAUNDRY round out the main level. Upstairs, two OVERSIZED bedrooms impress. The primary suite spans 24x16 with a private bath and walk-in closet, and the second bedroom at 20x18 has its own walk-in closet too. Everyone gets their own space here. Head downstairs to a FINISHED REC ROOM with daylight windows and walkout access - perfect for hobbies, a home gym, movie nights, or extra storage. The garage is OVERSIZED. Big enough to fit a truck and all the toys and tools you need. Out back, enjoy a patio in a wooded, country setting. HOA covers landscaping, water, sewer, plowing, and trash - truly low-maintenance living. Won't last!

2 Beds ⋅ 3 Baths ⋅ 5092343 MLS

You pull up to a quiet cul-de-sac, the noise of the world already fading behind you. A COVERED PORCH waits at the front door, the kind you actually use. Step inside and you'll know: this is the one. Nestled in Chester's Shaker Heights Estates, this meticulous MOVE-IN READY townhouse checks every box and then some. Pride of ownership shines through every room. The open main level welcomes you with gleaming hardwood floors and NATURAL LIGHT pouring in from every angle. The eat-in kitchen, a generous 17x15, features stainless steel appliances and flows right into the dining area, making everyday meals and weekend entertaining equally effortless. The living room is HUGE at 24x16 with a private DECK. Step outside, breathe in the wooded views, and make it your morning coffee spot or evening wind-down zone. A half bath and FIRST-FLOOR LAUNDRY round out the main level. Upstairs, two OVERSIZED bedrooms impress. The primary suite spans 24x16 with a private bath and walk-in closet, and the second bedroom at 20x18 has its own walk-in closet too. Everyone gets their own space here. Head downstairs to a FINISHED REC ROOM with daylight windows and walkout access - perfect for hobbies, a home gym, movie nights, or extra storage. The garage is OVERSIZED. Big enough to fit a truck and all the toys and tools you need. Out back, enjoy a patio in a wooded, country setting. HOA covers landscaping, water, sewer, plowing, and trash - truly low-maintenance living. Won't last!

15 Shaker Heights Ln, Chester

54 Fremont Rd Unit Unit A and Unit B, Chester

$429,000

Investment opportunity! For the cash Buyer only. This 2 unit duplex boasts 7.22 acres, long secluded driveway. Renters intact. Each unit has 2 spacious bedrooms, kitchen and dining combo, spacious living room . All bedrooms and full bathroom are upstairs and 1/2 bath off kitchen. Kitchen has fridge, dishwasher and stove. Laundry hookups are in the walk out basement. All electric heat and hotwater heater. Newer roof, new siding, new decks, new asphalt driveway. Renters are responsible for cable, and electric.

5070453 MLS

Investment opportunity! For the cash Buyer only. This 2 unit duplex boasts 7.22 acres, long secluded driveway. Renters intact. Each unit has 2 spacious bedrooms, kitchen and dining combo, spacious living room . All bedrooms and full bathroom are upstairs and 1/2 bath off kitchen. Kitchen has fridge, dishwasher and stove. Laundry hookups are in the walk out basement. All electric heat and hotwater heater. Newer roof, new siding, new decks, new asphalt driveway. Renters are responsible for cable, and electric.

54 Fremont Rd Unit Unit A and Unit B, Chester

$420,000

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

$379,000

Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the community as a schoolhouse until the early 1960s, the property was thoughtfully converted into a residence that honors its roots while offering comfortable modern living. The original schoolroom now anchors the home as a warm, open living space filled with natural light, where hardwood floors and tall windows create an airy yet cozy environment ideal for everyday living and gathering. The farmhouse-style kitchen flows seamlessly into the living area and features butcher block countertops, a professional-grade gas convection range with double ovens, and a breakfast bar with a charming pass-through window, perfect for casual meals and entertaining. A spiral staircase adds rustic character and leads to the upper level, offering a spacious bedroom or studio and flexible use for guests, creative space, or a private retreat. The primary suite serves as a peaceful sanctuary with vaulted ceilings, custom built-in shelving, a private full bath, and a cozy wood stove. Doors open to a rear deck overlooking the private yard and surrounding countryside. Additional features include a generous first-floor laundry area, enclosed sun porch, outdoor patio, a private hot tub with a heated walkway for truly maintenance-free winter access (no shoveling, ever!) and an attached two-car garage currently used as a game room, easily adapted back to garage space or reimagined as a workshop, studio, or home office. With commercial zoning, just 10 minutes from Okemo Mountain Resort, and a history as a successful Airbnb, this rare property offers character, flexibility, income potential, and true country charm.

2 Beds ⋅ 2 Baths ⋅ 5074728 MLS

Set on .76 acres in the peaceful Chester VT countryside, this former schoolhouse offers timeless farmhouse charm, rich history, and a setting that feels both private and inviting. Framed by classic stone walls, a pond site, and a gently wooded backdrop, the home sits just off a main road, providing easy access to town while maintaining a quiet, pastoral atmosphere. Originally serving the community as a schoolhouse until the early 1960s, the property was thoughtfully converted into a residence that honors its roots while offering comfortable modern living. The original schoolroom now anchors the home as a warm, open living space filled with natural light, where hardwood floors and tall windows create an airy yet cozy environment ideal for everyday living and gathering. The farmhouse-style kitchen flows seamlessly into the living area and features butcher block countertops, a professional-grade gas convection range with double ovens, and a breakfast bar with a charming pass-through window, perfect for casual meals and entertaining. A spiral staircase adds rustic character and leads to the upper level, offering a spacious bedroom or studio and flexible use for guests, creative space, or a private retreat. The primary suite serves as a peaceful sanctuary with vaulted ceilings, custom built-in shelving, a private full bath, and a cozy wood stove. Doors open to a rear deck overlooking the private yard and surrounding countryside. Additional features include a generous first-floor laundry area, enclosed sun porch, outdoor patio, a private hot tub with a heated walkway for truly maintenance-free winter access (no shoveling, ever!) and an attached two-car garage currently used as a game room, easily adapted back to garage space or reimagined as a workshop, studio, or home office. With commercial zoning, just 10 minutes from Okemo Mountain Resort, and a history as a successful Airbnb, this rare property offers character, flexibility, income potential, and true country charm.

3466 Vt Route 103 N, Chester

$359,000

Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you’ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area — perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity — come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment.

3 Beds ⋅ 1 Baths ⋅ 5070720 MLS

Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you’ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area — perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity — come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment.

531 Main St, Chester

$340,000

***Open House Wednesday August 12th, from 4pm-5:30pm*** Attention Contractors, flippers, and Investors! Great opportunity to build some sweat equity. Single Family with 4 beds 2 baths and 3,734 sqft. This is a property with a TON of potential. SOLD AS IS! Cash or Hard Money ONLY. Sale is contingent upon the seller completing their purchase; seller currently has the property under contract. Seller and seller’s reps. hold a real estate broker or agent license. Some personal items to remain and become the buyer's responsibility.

4 Beds ⋅ 2 Baths ⋅ 5104013 MLS

***Open House Wednesday August 12th, from 4pm-5:30pm*** Attention Contractors, flippers, and Investors! Great opportunity to build some sweat equity. Single Family with 4 beds 2 baths and 3,734 sqft. This is a property with a TON of potential. SOLD AS IS! Cash or Hard Money ONLY. Sale is contingent upon the seller completing their purchase; seller currently has the property under contract. Seller and seller’s reps. hold a real estate broker or agent license. Some personal items to remain and become the buyer's responsibility.

55 Chester St, Chester

$289,000

Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided from the parcel across the street and they may be purchased together. See MLS #5069927 This is a nice level to rolling lot with some open and some woods, has a 2 car garage, 2 enclosed porches and is well put together inside. The outside needs some finish work, so not likely to go a federal program. With some TLC this will be a fab get away. The town maintains the road to the house...such a benefit! This is a must see for location

2 Beds ⋅ 3 Baths ⋅ 5069928 MLS

Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided from the parcel across the street and they may be purchased together. See MLS #5069927 This is a nice level to rolling lot with some open and some woods, has a 2 car garage, 2 enclosed porches and is well put together inside. The outside needs some finish work, so not likely to go a federal program. With some TLC this will be a fab get away. The town maintains the road to the house...such a benefit! This is a must see for location

106 Contro Rd, Chester

$275,000

Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops and appliances. The main level offers a bedroom, dining room, office space and living room. All of the windows have been replaced (except in the attic), updated electric panel, insulation done by Efficiency VT, new stoves in the barn room and living room (see MLS docs for the complete list). This property is perfect for anyone looking for a TRUE Vermont home with loads of potential. Great natural light, large bedrooms, hardwood floors and attached garage. One of the features I personally love is the screened stone patio (barn room) off the back of the house. The rustic beams and barn boards with wood stove is a wonderful space to relax and entertain. Above is unfinished space ready for your ideas, work out space? yoga studio? game room? There are pretty perennials and gardens surrounding the home. The back yard is private with attached shed space and back deck. Chester is a wonderful community and this home is perfectly situated for easy access to I91, Grafton, ski resorts, shopping and walking to the village green. The sellers have loved owning this home and have created many many memories here. Don't miss your chance to be the next stewards of this truly special property.

4 Beds ⋅ 3 Baths ⋅ 5087965 MLS

Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops and appliances. The main level offers a bedroom, dining room, office space and living room. All of the windows have been replaced (except in the attic), updated electric panel, insulation done by Efficiency VT, new stoves in the barn room and living room (see MLS docs for the complete list). This property is perfect for anyone looking for a TRUE Vermont home with loads of potential. Great natural light, large bedrooms, hardwood floors and attached garage. One of the features I personally love is the screened stone patio (barn room) off the back of the house. The rustic beams and barn boards with wood stove is a wonderful space to relax and entertain. Above is unfinished space ready for your ideas, work out space? yoga studio? game room? There are pretty perennials and gardens surrounding the home. The back yard is private with attached shed space and back deck. Chester is a wonderful community and this home is perfectly situated for easy access to I91, Grafton, ski resorts, shopping and walking to the village green. The sellers have loved owning this home and have created many many memories here. Don't miss your chance to be the next stewards of this truly special property.

397 River St, Chester

$269,000

This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list.

3 Beds ⋅ 1 Baths ⋅ 5082324 MLS

This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list.

45 Dalrymple St, Chester