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109 Crowley Rd, Chester
$1,379,900
4 Beds ⋅ 3 Baths ⋅ 5106863 MLS
Stunning Brand-New Home READY NOW! Over 3.8 acres in Chester, NH showcasing over 3840 sq ft of an eye-catching design inside and out with metal roof accents, board/batten detail, stone veneer, black windows, 3 car garage plus gorgeous curb appeal with landscaping, granite paver walkway with 2 front porches. Inviting you inside to a 2-story foyer, wide plank natural white oak HDWD floors throughout, 9' first floor ceilings, interior transoms, coffered ceilings, solid core craftsman style doors, Baldwin door handles, crown molding, built-in bookcases to name a few... Designer dream mudroom complete with 2 built ins, closet, cabinetry and floating shelves. Top notch kitchen embraces all your senses with natural quartzite counters, CAFE appliances, 36" commercial stove with pot filler, oversized island, subtle yet striking backsplash, butler pantry area with glass cabs and a walk-in pantry. Light filled family room with a stone veneer gas fireplace. Spacious yet private 1st floor office/den with French door entry. Magnificent HDWD staircase makes a statement in this home from the light wood tone, boxed newels and rod iron balusters to the well-appointed 2nd floor. Private primary suite with a comfortable yet expansive space. His and hers oversized light and bright Walk in Closets. The primary bath tile shower with rain head/handheld features, glass enclosure, soaking tub, extra drawers in the double vanity, quartz counters, linen closet and private water closet. Every detail in this home has you in mind. Three roomy secondary bedrooms share a super functional full bathroom with double sinks, private tub shower/toilet room and 2 linen closets. 2nd floor laundry room with quartz counters/cabinets and designer floating shelves. Your private landscaped back yard oasis starts just steps from your impressive granite paver patio/back porch to plan all the best moments and create the best memories. Welcome Home! Agent interest.

109 Crowley Rd, Chester

1302 Popple Dungeon Rd, Chester
$1,349,000
5 Beds ⋅ 5 Baths ⋅ 5087874 MLS
Set on 18 private acres, Popple Fields is a very special Vermont property one that feels less like a house that was built and more like a home that was lovingly crafted. Built in 1989 by its owner, a true master craftsman, this Williamsburg saltbox reproduction reflects a lifelong appreciation for traditional architecture, fine woodworking, and the quiet beauty of things made by hand. The builder was a skilled Windsor chair maker whose work was featured in Yankee Magazine, and that same extraordinary attention to detail can be felt throughout the home. Inside, the craftsmanship is warm and beautifully understated. Wide plank wood floors, paneled walls, reclaimed beams, layered moldings, and custom woodwork give the rooms an authentic sense of age and character. The house has the gracious proportions and enduring appeal of an earlier era, while offering the comfort and livability of a thoughtfully designed modern home. Originally created as a bed and breakfast. There are inviting spaces for conversation and entertaining, along with quieter rooms that offer privacy and retreat. The result is a home that feels equally natural filled with family and friends. The land is every bit as evocative. Stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch unfold across the 18 acres. There is a wonderful feeling of discovery here paths to wander, gardens to tend, places to sit, and changing views through every season. A woodworking barn adds another layer of possibility, A genuine space for woodworking, craftsmanship and other creative pursuits. Just outside the charming village of Chester, Popple Fields is ideally situated to enjoy skiing, hiking, and exploring the surrounding countryside. But what makes this property truly distinctive is something that is difficult to replicate: the hand of the maker. The home carries the mark of the craftsman who designed and built it. This is a private VT retreat to be enjoyed for generations.

1302 Popple Dungeon Rd, Chester

37 Colby Farm Rd, Chester
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 5072786 MLS
HOME TO BE BUILT! THIS IS THE LAST LOT REMAINING!! Welcome to Colby Farm, an exclusive enclave of just 10 beautifully crafted single family homes, tucked away on a quiet cul de sac. Thoughtfully designed with both elegance & functionality in mind, each home offers spacious, customizable floor plans, allowing buyers to select finishes, appliances, and details to reflect their personal style. BRING YOUR OWN PLAN OR BUILD THIS FEATURED HOME. This farmhouse style home is a 3,018 sq. ft. retreat that blends timeless charm with modern living. The plan includes three generously sized bedrooms, two and a half well appointed bathrooms, & a convenient second floor laundry. At the heart of the home, the gourmet kitchen is designed to be tailored to your taste, with allowances for appliances, cabinetry, countertops, and finishes. A large center island & walk in pantry create a space that works beautifully for both everyday living and entertaining. The layout also features a flexible room ideal for a home office or den, an expansive great room for gatherings, & a welcoming mudroom leading to a spacious two car garage, all designed with comfort and livability in mind. Set along a scenic country road, Colby Farm offers the perfect balance of modern luxury and rural charm. A neighboring horse farm and 18 acres of conservation land enhance the peaceful surroundings, while the absence of condo fees adds to the appeal. Choose from the builder’s thoughtfully designed plans or bring your own vision to life. Photos are a facsimile of previous build.

37 Colby Farm Rd, Chester

76 Goldthwaite Rd, Chester
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 5088175 MLS
Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the fire pit beneath star filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55’ x 40’ barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small town charm that make Vermont so special.

76 Goldthwaite Rd, Chester

545 Lane Rd, Chester
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 5115257 MLS
A Home for the Holidays is calling. Tranquility awaits at this remarkably private, hilltop sanctuary set on 22.49 acres. A winding 700-foot driveway guides you past a serene pond, expansive stone walls, and mature landscaping. Custom-built this elegant 12+ room Cape seamlessly blends timeless character with modern luxury. Featuring 1,700 feet of road frontage, the property offers exceptional privacy, potential in-law accommodations, and room for entertaining. Inside, 9-foot ceilings, crown molding, and hardwood flooring run throughout the first floor. The main level opens to a soaring cathedral foyer with a balcony overlook, leading into a light-filled living room anchored by gorgeous stone fireplace. The gourmet kitchen boasts cherry cabinetry, granite countertops, a porcelain tile floor, a wine cooler, and a professional-grade 6-burner stove. An adjacent breakfast nook opens directly onto the rear deck for effortless indoor-outdoor living. A large coffered ceiling family room and dining room complete the first-floor entertaining spaces. The primary bedroom is a retreat featuring a large walk-in closet and a spa-like bath with double console sinks, a walk-in dual shower, and a 6-foot slipper clawfoot tub. A dedicated main-floor library/office with pocket doors and a mahogany-floored three-season porch with wood-paneled walls complete the level. Upstairs, find three spacious bedrooms, a full bath, a large flexible bonus room to suit your needs and a walk-in attic. The walk-out basement is built for multi-generational living, offering a recreation room, with a back-lit coffered ceiling, a stone fireplace, an additional bedroom, a 3/4 bath, an outdoor shower, and a custom wet bar with maple cabinets. Other amenities include a finished two-car garage with architectural doors, EV Charger, workshop area, shed, generator ready, top-tier mechanical systems and wired for an outdoor hottub. With over 270 acres of conservation land abutting the lot, this one is special!

545 Lane Rd, Chester

47 Wells Village Rd, Chester
$949,900
3 Beds ⋅ 2 Baths ⋅ 5114966 MLS
Discover the perfect blend of country living and equestrian functionality, all within walking distance to the charming center of Chester. Set on 9.6 picturesque acres, this well-maintained horse property offers approximately 5 acres of lush, verdant pasture, complemented by wooded areas that provide beauty, privacy, and endless riding enjoyment. The equestrian facilities include two barns with a total of four horse stalls and one pony stall. The barn setup is equipped with hot and cold running water, and an insulated tack room that provides comfortable year-round storage and workspace. The inviting home offers just under 2,300 square feet of living space with a warm, functional layout. Featuring three bedrooms and two full baths, the home showcases beautiful hardwood floors, a bright and spacious kitchen, and a bonus room ideally suited for a home office, hobby space, or den. First-floor laundry adds to everyday convenience. Just off the kitchen, a charming, screened porch provides the perfect place to relax and take in the natural beauty that surrounds you. Enjoy peaceful mornings with a cup of coffee, listen to the sounds of nature, and watch the changing seasons unfold from this tranquil retreat. Outside, the backyard also features a dedicated fenced-in area, offering a safe and versatile space for pets, play, or gardening. Lovingly cared for and thoughtfully updated, the home boasts improvements including vinyl siding, an updated heating system, a whole-house water filtration system, and much more. Whether you're an avid equestrian, hobby farmer, or simply seeking a peaceful country lifestyle with modern comforts, this rare Che

47 Wells Village Rd, Chester

1470 Popple Dungeon Rd, Chester
$879,900
5 Beds ⋅ 3 Baths ⋅ 5099745 MLS
Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment.

1470 Popple Dungeon Rd, Chester

11 Robin Way Unit 2, Chester
$789,900
3 Beds ⋅ 3 Baths ⋅ 5112505 MLS
The Eagle Farmhouse blends a classic colonial layout with a fresh, modern exterior. Step inside and you'll love the spacious open-concept design, perfect for both everyday living and entertaining! The kitchen features beautiful quartz countertops, ample cabinetry, and a seamless flow into the main living areas. Conveniently located off the garage, the mudroom provides the perfect drop zone for coats, shoes, and everyday essentials. A versatile den offers an ideal space for a home office, playroom, or guest area, while the inviting family room provides plenty of room to relax by the fireplace and gather with family and friends. Thoughtfully designed with comfort and functionality in mind the second floor offers two spacious bedrooms with walk-in closets, a dedicated laundry room, a full bath, and a spacious primary with en-suite with a lovely tiled walk-in shower designed to satisfy even the most discerning homeowner. Beautiful hardwood and tile flooring throughout. The full basement could be finished later for future additional living space if desired. Pet friendly and no age restrictions. Come and see what this small, charming community of detached condos in desirable Chester, NH has to offer. Builder's last home at Pipit Estates - do not miss out!

11 Robin Way Unit 2, Chester

11 Robin Way Unit 2, Chester
$789,900
3 Beds ⋅ 3 Baths ⋅ 5112504 MLS
The Eagle Farmhouse blends a classic colonial layout with a fresh, modern exterior. Step inside and you'll love the spacious open-concept design, perfect for both everyday living and entertaining! The kitchen features beautiful quartz countertops, ample cabinetry, and a seamless flow into the main living areas. Conveniently located off the garage, the mudroom provides the perfect drop zone for coats, shoes, and everyday essentials. A versatile den offers an ideal space for a home office, playroom, or guest area, while the inviting family room provides plenty of room to relax by the fireplace and gather with family and friends. Thoughtfully designed with comfort and functionality in mind the second floor offers two spacious bedrooms with walk-in closets, a dedicated laundry room, a full bath, and a spacious primary with en-suite with a lovely tiled walk-in shower designed to satisfy even the most discerning homeowner. Beautiful hardwood and tile flooring throughout. The full basement could be finished later for future additional living space if desired. Pet friendly and no age restrictions. Come and see what this small, charming community of detached condos in desirable Chester, NH has to offer. Builder's last home at Pipit Estates - do not miss out!

11 Robin Way Unit 2, Chester

18 Pomp Rd, Chester
$739,900
3 Beds ⋅ 2 Baths ⋅ 5108594 MLS
Welcome to your own private New Hampshire retreat! Set on approximately 2 acres in desirable Chester, this beautifully renovated 3-bedroom, 2-bathroom home has been completely transformed from top to bottom, offering modern comfort and style in a peaceful country setting. Step inside to a thoughtfully designed open-concept floor plan with a seamless flow between the living, dining, and kitchen areas. The extensive renovation provides the opportunity to move right in and enjoy a beautifully updated home without the projects that often come with country properties. Outside, the possibilities are endless. The property features a horse barn, making it an ideal setting for equestrian enthusiasts, while the private pond adds a picturesque touch and creates a serene backdrop for enjoying the outdoors. With approximately 2 acres, there is plenty of space for animals, recreation, gardening, entertaining, or simply enjoying the privacy and beauty of your surroundings. A truly special property offering the perfect combination of turnkey renovation, acreage, a horse barn, and a private pond, all in the charming town of Chester. Come experience the peaceful lifestyle and exceptional setting this property has to offer!

18 Pomp Rd, Chester

8 Robin Way Unit 7, Chester
$724,900
3 Beds ⋅ 3 Baths ⋅ 5102111 MLS
New Construction Without the Wait! Recently completed and loaded with premium upgrades, this beautifully appointed detached condominium offers modern design, quality craftsmanship, and low-maintenance living at Pulpit Estates, an exclusive, non-age-restricted and pet friendly community of just eight detached condominiums set on 16 picturesque acres in desirable Chester, NH. The sought-after Osprey floor plan offers the ease of FIRST FLOOR living with a spacious PRIMARY SUITE on the main level, while the second floor features two generously sized bedrooms and a full bath - ideal for family, guests, or a home office. Designed for today's lifestyle, the open-concept living, dining, and kitchen area is anchored by a gas fireplace and showcases numerous builder upgrades throughout. The custom kitchen features Wolf Grantley recessed-panel shaker cabinetry with soft-close drawers, a tall pantry cabinet, 30-inch upper cabinets with crown molding, a 60-inch center island with seating, granite ctops, recessed lighting and Frigidaire Galley SS applcs, including a gas range. Quality finishes continue throughout with 3¼-inch red oak flooring finished in upgraded Bona Traffic HD satin throughout the main living areas and primary bedroom, while all baths feature elegant 12" x 24" staggered brick-pattern tile. Central air conditioning, a whole-house water filtration system, upgraded lighting, and thoughtful designer selections complete the home. Need additional space? The daylight walk-out lower level offers outstanding potential for future finished living space, a home gym, rec room, or media area. Enjoy all the benefits of brand-new construction - without the delays, decisions, or surprises of building. Lawn was seeded/virtual grass pictured. Conveniently located in the charming town of Chester with easy access to shopping, major commuter routes, and the highly regarded Pinkerton Academy school district. OPEN HOUSE - Saturday, October 24th (1 to 2:30pm)

8 Robin Way Unit 7, Chester

98 Lady Slipper Ln, Chester
$699,900
3 Beds ⋅ 3 Baths ⋅ 5112319 MLS
Here is your opportunity to get into Chesterbrook Estates! Welcome to 98 Lady Slipper Lane. Set in a private neighborhood, this 3-bedroom Colonial home in Chester NH offers 2.5 baths, approximately 3,260 square feet of finished living space across three levels, and more than 1.25 acres. Priced under $700,000, this 2004-built home pairs a spacious floor plan with a peaceful setting overlooking a serene pond. Inside, you'll find plenty of room to spread out, including a large family room designed for comfortable everyday living and gatherings. Three finished levels provide added flexibility, highlighted by a third-floor bonus room that expands the possibilities for additional living, work, recreation, or hobby space. Need more space? The walk-out lower level offers future expansion possibilities. Outside, the back deck creates an inviting place to enjoy the natural surroundings and pond views. Additional features include a newer roof and two-car garage and whole house pellet stove heating system that is connected to the duct work. Enjoy the private oasis in your back yard, while still benefitting from a neighborhood setting. All of this and part of the Pinkerton Academy School District, this is one that you will not want to miss out on. Schedule your private showing today!

98 Lady Slipper Ln, Chester

3630 Vt Route 103 N, Chester
$650,000
5044879 MLS
Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic. In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use. Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, it is conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow. This versatile property allows for multiple avenues of income - whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless. Don't miss your chance to own a piece of this thriving community.

3630 Vt Route 103 N, Chester

23 School St, Chester
$649,000
5111465 MLS
A rare opportunity to acquire a fully occupied, well-maintained mixed-use property in one of Chester’s most recognizable village locations. The front portion of the building is leased as professional office space for $5,000 per month, with the commercial tenant responsible for heat and electricity. The tenant has expressed interest in entering into a significantly longer-term lease, with the lease length and additional terms to be negotiated directly with the next owner. The property includes four additional residential units, all currently rented, including one leased by the commercial tenant for employee housing. Detailed income, expense, and lease information is available through your agent. Carefully maintained over the years, the building requires no known major upgrades or repairs and is ready for its next owner. More than sufficient parking is available on both sides of the building, along with abundant storage throughout the property, including basement garage space. Its location just off the historic Chester Village Green provides excellent visibility and steady Main Street traffic for commercial use, while remaining comfortable and quiet for residential tenants. Local shops, restaurants, and village amenities are all nearby, and Chester’s iconic Swinging Bridge, the Williams River, and its scenic footpath are less than a quarter mile away at the end of School Street. With established tenants, multiple income streams, ample parking and storage, and an outstanding village location, 23 School Street offers an exceptional opportunity to step into a strong-performing property from day one.

23 School St, Chester

168 Chandler Rd, Chester
$627,000
3 Beds ⋅ 2 Baths ⋅ 5097737 MLS
Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet reflection. Step inside to discover warm, curated interiors where a matching floor-to-ceiling indoor fireplace anchors a cozy great room...an ideal focal point for gatherings and quiet nights in. The custom kitchen is a chef’s and designer's showcase making meal prep effortless and stylish. Cute, artful decor and exceptional millwork accentuate every room..every little detail has been considered and executed with eye-popping precision. Natural light pours through thoughtfully placed windows, highlighting textures, finishes, and curated vignettes around nearly every corner. In addition to the four private bedrooms, the special loft above the second-floor den offers a “fun” sleeping area and great retreat for the “kids”. Unique sightlines and charming nooks reveal something special at every turn.unexpected architectural details, refined accents, and cozy gathering spots create a home rich in personality and comfort. The floorplan flows intuitively while offering distinct spaces for entertaining and everyday living. Practicality meets luxury with a spacious second garage providing room for toys, workshop space, or secure storage perfect for multi-vehicle households or hobbyists. The gated setting ensures peace of mind and exclusivity, while the manicured wooded grounds offer a serene backdrop and a strong connection to nature. Come see how every corner captures your attention and inspires a sense of wonder at home. This mini-estate is only 10 miles from world-class skiing at Okemo and golf at Fox Run...then enjoy the 5 lakes of Okemo Valley and the nearby VAST trails!

168 Chandler Rd, Chester

256 Villager Rd, Chester
$624,900
2 Beds ⋅ 3 Baths ⋅ 5113580 MLS
Welcome to 256 Villager Road, a beautifully upgraded ranch style condo offering a unique floor plan, exceptional living space and one of the more private settings in the community. Surrounded by woods to the left and rear, this home enjoys a peaceful setting with no neighboring condo on one side or directly behind. Inside, hardwood floors flow throughout the first floor, where a spacious family room at the front of the home takes the place of the typical second bedroom, creating an inviting and open layout for everyday living and entertaining. The kitchen features granite countertops, a large center island, stainless steel appliances, including a gas range, and plenty of workspace and storage. The primary suite is a true retreat with a large soaking tub, oversized walk-in shower and double sinks. A convenient first-floor half bath includes laundry hookups, offering the option for one level living. An inviting sunroom provides the perfect place to relax and enjoy the peaceful surroundings and leads directly to a spacious deck overlooking the wooded setting, ideal for morning coffee, outdoor dining or entertaining. The attached two car garage provides easy access to the home with just two steps inside and an oversized entry door. The finished walkout lower level significantly expands the living space and offers tremendous flexibility. Here you’ll find a large family room, bedroom, office/study and a full bath with double sinks, along with an additional set of laundry hookups. Whether you’re looking for space for guests, a home office, hobbies or a separate living area, this level offers plenty of possibilities. Enjoy low maintenance condo living along with community amenities including an inground pool and clubhouse. With its upgraded finishes, flexible floor plan, generous living space and exceptionally private location, 256 Villager Road offers the space and comfort of a single-family home with the convenience of condominium living.

256 Villager Rd, Chester

21 Smith Rd, Chester
$620,000
3 Beds ⋅ 3 Baths ⋅ 5111937 MLS
Tucked into a private setting in the charming town of Chester, this 3-bedroom, 2.5-bath home offers plenty of space, natural light and a few unexpected surprises! The updated kitchen features granite countertops, stainless steel appliances, ample cabinetry and workspace, while radiant heat adds warmth and comfort throughout. Upstairs, the primary suite is a standout, featuring a beautifully appointed, luxurious private bath and access to its own balcony overlooking the natural surroundings, a peaceful spot to enjoy your morning coffee or unwind at the end of the day. Two additional bedrooms and another bath complete the upper level. Need more space? The finished lower level provides flexible bonus space for a family room, home office, gym or playroom, along with plenty of additional storage. Set back in a peaceful location with wonderful sun exposure and a sense of privacy, this home offers an opportunity to enjoy the quieter side of New Hampshire living while remaining convenient to surrounding towns, shopping and commuter routes. Bring your vision and make this Chester home your own!

21 Smith Rd, Chester

15 Ledge Rd, Chester
$599,900
3 Beds ⋅ 2 Baths ⋅ 5106758 MLS
Step back in time without giving up today’s modern comforts in this thoughtfully designed antique replica Cape, beautifully crafted by the renowned Tammy Grimes. Set privately on 2.8 serene acres, this exceptional home captures the character, warmth, and timeless charm of an antique New England home while offering the conveniences and updates today’s buyers desire. Inside, you’ll find beautifully preserved character paired with thoughtful modern improvements. The newly redesigned first-floor bathroom features a stunning tiled shower, while the custom kitchen offers both functionality and distinctive style. Cozy up by the pellet stove or enjoy the comfort of forced hot-air heat throughout the home. A whole-house generator provides added peace of mind in every season. The private, peaceful setting offers plenty of room to relax, entertain, garden, or simply enjoy the tranquility of your surroundings. With its classic Cape architecture, inviting interior, custom details, and modern amenities, this is a truly special property that blends the romance of an antique home with the comfort of contemporary living. A rare opportunity to own a piece of timeless New England charm in a beautiful Chester setting.

15 Ledge Rd, Chester

548 Crow Hill Rd, Chester
$599,000
4 Beds ⋅ 2 Baths ⋅ 5106579 MLS
Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for. Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide confidence and convenience for years to come. Inside, the practical floor plan includes a desirable first-floor primary bedroom and first-floor laundry, making everyday living comfortable and accessible. The remaining bedrooms offer flexibility for guests, a home office, hobbies, or creative space. Step outside to enjoy beautifully landscaped grounds, a spacious deck built around an above-ground pool, and the quiet surroundings that define rural Vermont living. Multiple barns and sheds provide exceptional versatility, whether you're looking for a workshop, tractor or recreational vehicle storage, equipment space, or even a former horse stall ready for new possibilities. Combining privacy, usable acreage, and a property that has been lovingly maintained over the years, this home offers the opportunity to enjoy country living without sacrificing comfort. Whether you're looking for room to spread out, space for projects, or simply a peaceful place to call home, this property is ready to welcome its next owners.

548 Crow Hill Rd, Chester

197a Chester St, Chester
$579,900
5090837 MLS
This property presents a rare opportunity to own a large lot on desirable Chester St. Many options here: Update the house and create a huge farm property, build a new house and use the existing house as an ADU/cottage or other, subdivide into two lots with town approvals ** A beautiful country setting for this 16.4+/- acre farm with wooded areas to explore. ** This classic farmhouse offers 2 bedrooms, 2 baths, large eat-in kitchen, laminate, tile and soft wood floors. NEWER forced hot water boiler. Many farm features: Chicken coop, fenced in areas, 20x24 2-stall horse pole barn, a large barn that was moved to the property from another site in Chester. Peaceful, yet conveniently located, about 8.5 miles to Exit 4 I-93 and about 6.9 miles to Exit 2 Route 101. About Chester ** WASON POND is where residents can go to enjoy a quiet, natural place to walk, hike, cross-country ski, walk dogs, kayak, picnic, and swim. SCHOOLS: Consists of elementary & middle school, Chester Academy and the High School is Pinkerton Academy, in Derry. SCARECROWS: The town has been going scarecrow crazy for many years. Every October there are over 400 scarecrows placed all over town with a map showing the locations. The scarecrows will be on display through Oct. 31. HALLOWEEN NIGHT: Brings many visitors to Chester Street, where over the years Trick or Treat has become a must-see event. AGENTS & BUYERS to do their own Due Diligence to verify all listing information and verify options with town and necessary approvals to do so. Room sizes are for reference only; not guaranteed. *** House being sold in current condition and all items on the property to remain after month-to-month tenant leaves. House is tenant occupied and works from the house.

197a Chester St, Chester

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

136 Haverhill Rd, Chester
$569,000
3 Beds ⋅ 2 Baths ⋅ 5112156 MLS
Welcome to your own private retreat on 2.2 picturesque acres in beautiful Chester, New Hampshire! Set back on a peaceful lot surrounded by nature, this charming single-family home offers the perfect blend of peaceful country living, thoughtful updates, and everyday comfort. Inside, you’ll find 3 bedrooms and 1.5 newly renovated bathrooms, along with an inviting, recently updated kitchen featuring quartz countertops, a stylish tile backsplash, and brand-new stainless-steel appliances. The bright eat-in kitchen is made even more welcoming by a beautiful bay window, creating a wonderful spot to enjoy morning coffee or casual meals while taking in the view. Warm bamboo flooring & new carpet throughout the home, while the brick wood-burning fireplace adds a cozy focal point for relaxing evenings in the living room. One of the home’s true showstoppers is the breathtaking screened-in porch, a serene space surrounded by nature where you can unwind, entertain, dine, & relax to the sounds of the outdoors. The 20x22 basement provides ample bonus space, as well as a half bath, laundry, & plenty of storage options. Step outside and discover everything this special property has to offer. The expansive, private lot features an open field, mature apple trees, a small barn, and a shed with electricity, providing plenty of space for hobbies, gardening, storage, animals, or simply enjoying the outdoors. Whether you’re seeking a peaceful place to call home or a property that allows you to fully embrace the beauty of nature, this Chester gem offers a rare opportunity of privacy, charm, and modern updates. Come experience the setting, explore the possibilities, and discover all this special property has to offer.

136 Haverhill Rd, Chester

124 Haverhill Rd, Chester
$545,000
3 Beds ⋅ 2 Baths ⋅ 5112964 MLS
Welcome to 124 Haverhill Road, a well-cared-for raised ranch on a beautifully landscaped lot in Chester, NH. Mature pear, cherry, apple and peach trees, along with blooming magnolias and established plantings, frame the property with color in spring and a harvest each season. The main level features gleaming hardwood floors throughout. The spacious living room is bright with natural light and recessed lighting. Near the entry, a pellet stove set on a classic brick hearth adds cozy warmth and helps keep heating costs down. The eat-in kitchen offers two ways to dine: a large center island with seating for three, perfect for quick breakfasts and casual conversation, plus a separate dining area with room for a full-size table, set beside a sunny picture window. Plenty of wood cabinet storage and pendant lighting complete the space. Three bedrooms include a primary bedroom with its own private 3/4 bath, plus a full bath for a total of 1.75 baths. Step out back to the three-season porch overlooking the private yard, a relaxing spot for quiet evenings or entertaining from spring through fall. The partially finished lower level has been updated with brand-new luxury vinyl plank flooring and features a second stove on a brick hearth, ready for a rec room, home office or gym. The one-car garage under offers everyday convenience and extra storage, and the driveway has been recently paved. Small-town Chester living with easy access to Derry, Manchester and I-93.

124 Haverhill Rd, Chester

251 Villager Rd, Chester
$539,900
2 Beds ⋅ 3 Baths ⋅ 5112231 MLS
Live, love, leave the yardwork to someone else! This beautiful condo at the Villages of Chester will capture your heart as soon as you walk in. As you stand on the front porch you'll have a view of nothing but greenery and sky across the street. Step into the welcoming entryway and you'll see almost the entire first floor, from the living room to the dining area, kitchen, and sunroom in back. The living room is graced with a gas fireplace for cozy ambiance, the tall bookcases will stay with the property, and those lovel bamboo floors carry throughout the home. The dining area is open to everything, and the gorgeous kitchen has a 3-seat oversized island, so it will be the hub of activity in the home. And with so many cabinets, you'll have to buy extra gadgets to fill them all! The sunroom flows right out to the 15' x 11' deck, integrating indoors with outdoors seamlessly and creating a great flow for visiting friends and family. Upstairs is a spacious primary suite, second bedroom, and convenient laundry room with an extra half bath. The basement is almost fully finished, with two spacious rooms for workouts, guest space, or whatever you want, as well as another three-quarter bathroom (with perhaps a sauna?) and a small kitchenette area. The 2-car garage is an uncommon feature as well, and has an extra pantry closet and additional storage above the doors and behind the stairs. The Villages includes trails, a pond, a pool & clubhouse, and has easy access to the quaint center of Chester as well as Rt. 101, and cats and dogs are welcome as well. You're at the tail end of a cul-de-sac so you won't see many cars going by, and you can set up a little garden in the green space across the street. Schedule your visit and start planning how you'll live in and love this home! OPEN HOUSES Sat. 10/17, 10am-Noon, Sun. 10/18, 11am-1:00 pm.

251 Villager Rd, Chester

3341 Trebo Rd, Chester
$535,000
4 Beds ⋅ 3 Baths ⋅ 5086105 MLS
Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical.

3341 Trebo Rd, Chester

47 Lyon Hill Rd, Chester
$495,000
3 Beds ⋅ 2 Baths ⋅ 73594566 MLS
Custom-built Contemporary is ready for its second owner. Perfect blend of comfort, privacy and natural beauty on 9.7 acres. Meander on the 9.7 acres with a babbling brook that can be heard from the front porch. There are distant mountain views, not visible from the house. The main floor features a kitchen with cabinets galore and a wine frig, cathedral ceiling in the dining room with a fireplace, generous size living room with views to the outside, two bedrooms and a bathroom. The second floor features a generous size bedroom with a private bathroom and an open sitting area that could function as a study. Partially finished basement with a room that functioned as a prior wine cellar. The kitchen and bathroom were updated 14 years ago, approximately. The roof was replaced in 2010 and the heating system in 2012. There is enough frontage for the potential for another lot or lots, buyer to verify, the property is being sold as one lot. The seller is installing a new septic system.

47 Lyon Hill Rd, Chester

56 Shepard Home Rd, Chester
$459,000
3 Beds ⋅ 1 Baths ⋅ 5107622 MLS
NEW PRICE and 1 year home warranty! Enjoy peaceful riverfront living in this charming, light-filled Ranch with direct access to the Exeter River (not in a flood zone)! Privately situated on a beautiful lot in Chester with no neighboring homes visible on either side, this property offers a wonderful blend of comfort and natural surroundings. Inside, you’ll find easy one-level living with 2–3 bedrooms, an updated kitchen, full bathroom, and a cozy wood stove for those chilly New Hampshire nights. The spacious deck overlooks the river, providing the perfect spot to relax, entertain, or enjoy the abundant wildlife. Fish from your backyard or launch a canoe when water levels allow! Additional features include a basement for storage& two sheds. Located outside the designated flood zone, this unique property is ideal for those seeking privacy, nature, and a relaxed lifestyle. Quick close possible!

56 Shepard Home Rd, Chester

81 Main St, Chester
$445,000
5 Beds ⋅ 4 Baths ⋅ 5095551 MLS
Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont outdoor destinations, this property offers year-round access to skiing, hiking, recreation, and travel throughout the region.

81 Main St, Chester

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