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1260 Grafton Rd, Chester
$650,000
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
47 Edwards Mill Rd, Chester
$625,000
3 Beds ⋅ 2 Baths ⋅ 5085711 MLS
This exclusive yet accessible home will not last long! Enjoy entertaining in the 22x18 open concept family room with a pellet stove. The large living space with a custom built in bar leads out to the screened porch overlooking the large, but easily maintained, fenced in backyard. Enjoy cooking in the open kitchen with center island, granite counters, stone backsplash, and stainless steel appliances including a gas range. Formal dining room with hardwood floors. The front to back living room with a pellet stove is sure to keep you cozy on cool winter nights. Large Master Bedroom with his/her closets including a walk-in. 2 car garage for additional space. This amazing location is only 30 minutes to Portsmouth and under an hour from Boston! Showings begin at open houses on Saturday, May 2 from 12-1:30 and Sunday 11-12:30.

47 Edwards Mill Rd, Chester
519 Candia Rd, Chester
$620,000
3 Beds ⋅ 1 Baths ⋅ 5085913 MLS
Do you love a log cabin? Don't miss this opportunity for country living. Spacious detached heated garage for hobbies, well-built chicken coop, 4 raised garden beds, fruit trees, trails and an above ground pool. The living room offers a beautiful fireplace with plenty of room for a dining room table. The master bedroom on the first floor has a cedar closet. There are two rooms in the loft, and one has a full-length crawl space. Come see for yourself at the open houses on Saturday May 2nd 11:00-1:00 and Sunday May 3rd 12:00-2:00.

519 Candia Rd, Chester
149 Pheasant Run Dr, Chester
$615,000
3 Beds ⋅ 2 Baths ⋅ 5089049 MLS
Beautifully maintained 3-bedroom, 2-bath home situated on a scenic 1.1-acre sloping lot overlooking the Exeter River. Features include a walkout basement, detached 2-car garage, and large rear deck with river views. Recently finished upstairs offers a private bedroom suite with ¾ bath and office area. Peaceful setting with plenty of outdoor enjoyment and flexible living space.

149 Pheasant Run Dr, Chester
267 Haverhill Rd, Chester
$608,000
3 Beds ⋅ 3 Baths ⋅ 5105191 MLS

267 Haverhill Rd, Chester
51 Halls Village Rd, Chester
$600,000
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
32 Gypsum Ln Unit 30, Chester
$599,900
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
34 Gypsum Ln Unit 31, Chester
$599,900
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
506 Skyline Trl, Chester
$580,000
4 Beds ⋅ 2 Baths ⋅ 73513068 MLS
Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and a seamless open layout. A long, estate-style concrete approach creates a striking sense of arrival, leading into a thoughtfully updated interior featuring porcelain tile flooring, modern upgrades, and two fireplaces that add warmth and architectural character. A versatile finished bonus space off the main living area provides flexibility, ideal as a family room, studio, fitness area, or easily converted back to a two-car garage. A charming barn offers additional space for equestrian pursuits or curated hobby use without overpowering the setting. Included is a separate buildable lot, presenting exceptional opportunity for future development, guest accommodations, or long-term investment. Surrounded by mature rhododendrons and natural landscape, the home offers exceptional privacy, a peaceful setting, and a true retreat-like atmosphere.

506 Skyline Trl, Chester
16 Gypsum Ln Unit 26, Chester
$579,900
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
197 Chester St, Chester
$579,900
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
4 Gypsum Ln Unit 24, Chester
$569,900
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
12 Gypsum Ln Unit 25, Chester
$569,900
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
147 Pleasant View Ln, Chester
$569,000
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
17 Derry Rd, Chester
$565,000
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
211 Sandown Rd, Chester
$542,500
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
224 Haverhill Rd, Chester
$535,000
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
42 Great Oak Dr, Chester
$520,000
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
274 Goss Hill Rd, Chester
$515,000
3 Beds ⋅ 3 Baths ⋅ 73518494 MLS
Highest & Best by Wed. 4/20 @ 5pm. Tucked just minutes off Route 112, this well-maintained 2,644 sq ft cedar-sided Colonial is located in Chester, on the Huntington/Worthington line. Set on 4.25 private acres abutting state land, the property offers scenic views, a peaceful pond, and charming stone walls—creating a picturesque and tranquil setting. Inside, the spacious kitchen is ideal for entertaining, with sliding doors that open to a full-length composite deck overlooking the backyard. The living room features a cozy wood stove insert, while the dining room, currently used as an office, offers flexibility to fit your needs. A generous family room with deck access could easily be converted into a first-floor primary suite with additional laundry hook ups on the 1st & 2nd floor. The 2nd floor offers three comfortable bedrooms and two full baths. Additional highlights include a heated three-car attached garage with workspace a 1 ton trolly hoist and a detached second garage.

274 Goss Hill Rd, Chester
514 First Ave, Chester
$515,000
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
40 Old Sandown Rd, Chester
$500,000
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
79 Haverhill Rd, Chester
$500,000
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
111 Shepard Home Rd, Chester
$499,900
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
414 Fremont Rd, Chester
$495,000
4 Beds ⋅ 3 Baths ⋅ 73514081 MLS
-HIGHEST AND BEST OFFERS DUE WEDNESDAY - 3:00 PM - Don’t miss this versatile two-family ranch in desirable Chester, NH. Perfect for owner-occupants, investors, multi-generational living, or possible in-home business use, this property offers flexibility and future potential. Both first-floor ranch-style units have been freshly painted with some flooring updates completed, creating a move-in ready opportunity with room to build equity over time. The lower level with separate entry adds additional versatility with semi-finished rooms, a full bath, wet bar, cabinetry, and bonus space ideal for recreation, office space, workshops, hobbies, storage, or extended use (not a 3rd unit). There is also potential to connect the lower level to one unit for expanded living space. Live in one side while renting the other to help offset your mortgage, create an income-producing property or customize the space to fit your needs. Set on over an acre with a large deck and peaceful surroundings,

414 Fremont Rd, Chester
414 Fremont Rd, Chester
$495,000
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
3078 Vt Route 10, Chester
$480,000
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
547 Williams Rd, Chester
$460,000
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
21 Villager Rd, Chester
$449,900
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
64 Maple St, Chester
$449,000
3 Beds ⋅ 3 Baths ⋅ 5087175 MLS
Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area that works just as well for casual dining as it does for a home office setup. The dining space flows easily into a sunken living room, where the pellet stove becomes a natural gathering spot. Two bedrooms on the main level, each with their own bath, make this a great fit for a variety of living situations. Upstairs, you’ll find a spacious bedroom, a separate flex room currently used as a movie room, and an unfinished bonus area ready for whatever you have in mind. Storage is not an issue here, between the closets and full basement, there’s plenty of space to keep things organized. The home is equipped with a new furnace and four heating zones, offering efficiency and control throughout. Outside, a wide back patio gives you a great place to relax, while the barn and oversized three-bay garage offer serious utility for storage, equipment, or hobbies. The detached garage is currently rented for $500 per month, and the tenant would be open to continuing that arrangement with the next owner. The property borders Lovers Lane Brook, adding to the natural setting and privacy, all just minutes to Chester’s shops, dining, and village amenities. If you’ve been looking for an in-town property with more space and versatility than most, this one is worth a look. Furnishings are negotiable for anyone looking for a truly turn-key property!

64 Maple St, Chester
205 Villager Rd, Chester
$445,000
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

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