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254 Route 20, Chester, MA
$229,900
2 Beds ⋅ 2 Baths ⋅ 73594709 MLS
Welcome to this historic Colonial home nestled in the center of Chester, offering charm and modern potential. Featuring 6 spacious rooms, including 3 generous bedrooms and 1.5 bathrooms, this home is ideal for Living, investors, or those seeking an Airbnb rental opportunity. Inside, enjoy the warmth of beautiful wood floors throughout most of the home, a large kitchen with ample counter and cabinet space, and closets galore for all your storage needs. Additional features include a spacious three-season front porch that’s surrounded by natural light accented by a beautiful wood ceiling, vinyl windows, an attached 1-car garage, and a storage shed — all situated on a 0.36-acre lot. Located along the scenic Westfield River, this property is a haven for outdoor lovers, with nearby hiking and riding trails, and is just a short drive to Jacobs Pillow, Tanglewood, Lee Outlets, and only 30 minutes to Westfield or the Berkshires.

254 Route 20, Chester, MA
47 Lyon Hill Rd, Chester, MA
$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. 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, MA
545 Lane Rd, Chester, NH
$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, NH
47 Wells Village Rd, Chester, NH
$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, NH
27 Maple Ave, Chester, MA
$290,000
3 Beds ⋅ 2 Baths ⋅ 73589335 MLS
Very well-maintained home on dead end street within walking distance to store, 2 restaurants and library. Walk out onto the back deck, to a nice size yard, with the West Branch of the Westfield River in your back yard. Come home and stick your toes in the water and relax to the serene sound of the babbling river, after a long day. 2 story conventional style home with 6 rooms, 3 bedrooms, 1.25 baths, 1 car attached garage and a cute front porch. Title V failed, perc test done, design completed and out for bid. and new septic system to be installed. Same owner for 50 years and it is time for new owners to enjoy this ready to move in home. Be in for the holidays. Don't miss this sweet home.

27 Maple Ave, Chester, MA
256 Villager Rd, Chester, NH
$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, NH
124 Haverhill Rd, Chester, NH
$524,900
3 Beds ⋅ 2 Baths ⋅ 5112964 MLS
New price! The expensive work is already done in this 3-bedroom, 1.75-bath raised ranch, set on a private 0.62-acre wooded lot in Chester. Major updates include a newer architectural roof, a freshly paved driveway, and a newly finished lower level with brand-new LVP flooring. A pellet stove on a classic brick hearth keeps winter heating costs down. Upstairs, hardwood floors run throughout the bright main level. The eat-in kitchen has a large center island, generous cabinet space and room for a full dining table. The living room has recessed lighting, and the sunroom looks out over the back deck and wooded backyard. The primary bedroom has its own ¾ bath. The lower level adds flexible space for a rec room, home office or gym, with walls primed and ready for your colors. About 1,676 sq ft on the main level, plus a one-car garage under. Quiet setting with an easy commute to Derry, Manchester and I-93. Served by Chester Academy (PreK–8) and Pinkerton Academy (9–12); buyer to verify school assignment.

124 Haverhill Rd, Chester, NH
2 Taft Rd, Chester, MA
$39,000
73586614 MLS
Unique Property with Multiple Outbuildings and Versatile Use Potential Discover a rare opportunity in Chester — a property offering multiple outbuildings, upgraded utilities, and flexible space for storage, recreation, or future development.The land includes two well-built sheds:Utility Shed — insulated, equipped with electric heat, and houses the well pump, providing reliable year-round functionality. Cabin-Style Shed — transformed into a comfortable retreat with 200-amp electrical service, electric heat, and full insulation, making it ideal as a workshop or hobby space.A metal shipping container on the property adds substantial secure storage for equipment, tools, or recreational gear. Whether you’re looking for a getaway spot, a base for outdoor activities, or a property with ready-made utility structures, this location offers exceptional versatility.

2 Taft Rd, Chester, MA
11 Robin Way Unit 2, Chester, NH
$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, NH
11 Robin Way Unit 2, Chester, NH
$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, NH
25 Villager Rd, Chester, NH
$433,900
2 Beds ⋅ 2 Baths ⋅ 5112444 MLS
Seller is offering a $5,000 credit toward the buyer's closing costs on an accepted contract that closes by December 15, 2026. Vacant and move-in ready! End-unit townhouse at The Villages at Chester with 1,954 finished square feet and your own private garden area. Hardwood on the first two floors, a stacked-stone gas fireplace, and a kitchen with granite, stainless and a five-burner gas stove. Deck runs the full width of the house. Vaulted-ceiling primary bedroom with a skylight and California Closets walk-in. Spacious second bedroom. Walkout lower level with a second living area, full-size windows and a slider to the patio, plus separate rooms for guests and an office or gym. Attached garage, mudroom with half bath, first-floor laundry. Newer Andersen windows and a tankless on-demand water heater. The building is getting new vinyl siding this fall, paid for by the Association. The HOA fee covers plowing, shoveling of walkways, landscaping, water, sewer and trash, plus the pool, clubhouse and nature trails. Pets welcome. Looking for an investment? The Association rules allow owners to rent their units. Please check out the virtual tour!

25 Villager Rd, Chester, NH
98 Lady Slipper Ln, Chester, NH
$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, NH
251 Villager Rd, Chester, NH
$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, NH
136 Haverhill Rd, Chester, NH
$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, NH
21 Smith Rd, Chester, NH
$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, NH
Mica Mill Rd, Chester, MA
$129,000
73582709 MLS
Opportunity to own 28.00 acres in Chester's rural hilltown setting. Located at 0 Mica Mill Rd, this vacant parcel is identified in town records as AR Agricultural Residential and offers a canvas for a future homesite or other potential use, subject to all required approvals. Enjoy a quiet western Massachusetts location with access to the Berkshires and Pioneer Valley region. Buyer and buyer's agent to independently verify all information and perform all due diligence, including boundaries, legal access and road status, zoning, permitted uses, wetlands, soils/perc, septic, utilities, and any development or subdivision potential. Parcel map is for location reference only and is not a survey.

Mica Mill Rd, Chester, MA
93 Crane Rd, Chester, MA
$129,900
1 Baths ⋅ 73579781 MLS
Escape to the scenic hills of Chester with this unique 5.2-acre property offering the opportunity to create your year-round country home. Two major infrastructure investments are already in place with the well and three bedroom septic system. Giving you the head start on your new home. The existing 560-square-foot cottage provides a comfortable retreat while you plan and develop your vision for the property. Surrounded by wooded acreage, the setting offers privacy, natural beauty, and plenty of room to enjoy the outdoors. In the meantime, the existing cottage makes an excellent weekend getaway, hunting lodge, or recreational retreat. Built in 2011 with a metal roof, wood exterior, the cottage provides a solid starting point. A special opportunity to build a year-round home in a peaceful Western Massachusetts setting while enjoying the property today. Buyer to perform all due diligence regarding zoning, permitting, building requirements, and future use.

93 Crane Rd, Chester, MA
18 Pomp Rd, Chester, NH
$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, NH
56 Shepard Home Rd, Chester, NH
$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, NH
109 Crowley Rd, Chester, NH
$1,379,900
4 Beds ⋅ 3 Baths ⋅ 5106863 MLS
OPEN HOUSE Sat Oct. 31st 12pm-3pm/Sun Nov 1st-10am-3pm. 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 & landscaping, granite paver walkway w/ 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, NH
15 Ledge Rd, Chester, NH
$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, NH
23 Maple St, Chester, MA
$215,000
2 Beds ⋅ 1 Baths ⋅ 73563768 MLS
Welcome home to your little slice of a rural countryside community. This property is situated on the west branch of the Westfield River in a quiet but convenient location. Enjoy your coffee on the porch and get lost in the sounds of nature. Inside you will find an open floor plan, a newer primary first floor bedroom, and three rooms upstairs with closets. This home is a hidden gem with tons of potential. Book your showing and bring your vision. Water heater purchased in 2021. Roof on addition was put on this year APO. Roof on main part of house is about 12 years old. 500 gal propane tank is owned. Buyer to do due diligence. Property appraised for 239k.

23 Maple St, Chester, MA
50 Smith, Chester, MA
$40,000
73563694 MLS
10-Acre Land OpportunityBring your vision to this beautiful 10-acre parcel of land and imagine what could be created here. The sellers once had grand plans for this property, but life has changed, creating an exciting opportunity for someone else to bring those plans to life.The property offers the potential to recreate what was once here, with building limited to the footprint/use of the former structure. A well and septic system will be required. Buyers are encouraged to conduct their own due diligence with the town regarding building, septic, well, permits, and allowable uses.Bring your design. Bring your vision. Bring your dreams. This could be the opportunity to create something truly your own on 10 acres of land.

50 Smith, Chester, MA
166 Route 20, Chester, MA
$80,000
2 Beds ⋅ 2 Baths ⋅ 73561688 MLS
Investors take note of the potential offered by this charming colonial home. Property is being sold as-is. The seller prefers a 60-day closing to allow sufficient time for removal of personal items from the house, yard, and barn. Title V has failed and will be the buyer’s responsibility. The home features partially updated plumbing and electrical systems, including an electrical panel and hot water tank installed approximately three years ago.

166 Route 20, Chester, MA
8 Robin Way Unit 7, Chester, NH
$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, NH
lot 3 Holcomb Road, Chester, MA
$60,000
73543996 MLS
Open land. Prime 2-acre pasture, building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land, One of 4 lots available.

lot 3 Holcomb Road, Chester, MA
lot 2 Holcomb Road, Chester, MA
$45,000
73543991 MLS
Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

lot 2 Holcomb Road, Chester, MA
lot1 Holcomb Road, Chester, MA
$45,000
73543989 MLS
Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

lot1 Holcomb Road, Chester, MA
91 Lynes Rd, Chester, MA
$50,000
73542747 MLS
Discover 3.47 acres of wooded land tucked along a tree-lined, unpaved road in Chester, known as the "Gem of the Valley." Chester offers a blend of small-town charm and outdoor recreation, from the Chester on Track festival and the Railway Museum to the Keystone Arch Bridges Trail and a vibrant local theatre community. Public records identify the parcel as residential (use code 130). If you’ve been searching for a wooded retreat or a land opportunity in a scenic hilltown, this parcel is worth a look. Seller says they had a successful perc test in the 80s. Photos provided are shown for reference only. Buyer to perform all due diligence for use, suitability, property lines, and boundaries. Schedule your visit today! Please do not walk the property without an appointment.

91 Lynes Rd, Chester, MA
27 Main St, Chester, MA
$225,000
73529752 MLS
Mixed-Use Building with Commercial Storefront and Residential Unit Mixed-use building with street-level commercial storefront and residential unit above. The 1,290 SF commercial space is available for lease and it includes hardwood flooring, track lighting, and a dedicated rear work area with industrial wash basins. It also includes a newly updated oil furnace. Located on a corner along Main Street in Chester, the property combines commercial and residential use within a single structure. Additional details available upon request. Sale Price: $225,000

27 Main St, Chester, MA

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