$720,775Average Value$317Average Price per Sq Ft9Homes For Sale
Rural Chester has access to nearby towns
Chester, 6 miles from Derry, is a town in Rockingham County with a rural environment and access to connective roadways. Chester has two major roadways running through it: State Route 102, which runs east-west, and State Route 121, which runs north-south. It also has access to Interstates 93 and 95. “Specifically for Chester, people like the affordability with proximity to some of the other, bigger towns, without the price increase,” says Heather Hanlon, a Realtor with Coldwell Banker Realty who sells in New Hampshire and Massachusetts. Hanlon has 8 years of experience in the real estate industry. “If you’re looking for land, it’s a good option.” The area has rolling hills and acres of old farmland and trees, with a few shops in the center of town. While Chester remains mainly rural, several housing communities are being built, leading to more growth in the area.
Pawtuckaway State Park is known for its glacial boulders, scenic lake, and hiking trails.
Chester locals may visit the local Hannaford for their everyday grocery needs.
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Homes on large lots
Most homes in Chester are in the central part of town along State Routes 102 and 121. Owing to the fact that the town’s economy was largely agricultural for much of its early existence, houses here are typically on large lots of old farmland. "One of the homes I sold had leftover orchard trees," says Hanlon. "They may have been for personal use or part of a larger orchard. We don't know. There's lots of farmland and lots of old houses on farmland." Most homes are in the Colonial Revival style and range from $375,000 to $775,000, while townhouses and condos range from $395,000 to $600,000. New single-family and condominium communities are in the New Traditional style, ranging from $800,000 to over $1.4 million. Townhouses and condos range from $615,000 to $835,000.
Homes in Chester often feature large front and back yards.
Colonial-style homes with attached garages are a common sight in Chester.
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Students attend schools in Chester and Derry
Chester School District SAU 82 serves the area, and children may attend Chester Academy, which receives a C-plus from Niche, for kindergarten through eighth grade. Students can continue to the private Pinkerton Academy in Derry, which also gets a C-plus, for high school. Chester is a sending town for Pinkerton, meaning that students attend the school free of charge, as New Hampshire’s Town Tuitioning Program covers the cost. Pinkerton Academy has over 60 student clubs, including art, skiing and a literary magazine.
Chester Academy provides a well-rounded education and promotes academic excellence.
The Pinkerton Academy in Suburban Rockingham County has over 3,000 students and a ratio of 20:1.
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Commuters use State Routes 102 and 101
Using State Route 102, commuters can head southwest to reach Derry in about 12 minutes or northeast to reach Raymond, 9 miles away, in 15 minutes. Using State Route 101, residents can typically get to the coast in less than 40 minutes. Using Interstate 93, commuters may head south into Lawrence, Massachusetts, about 25 miles away. Residents can also access the Cooperative Alliance for Regional Transportation (CART), a ride-request service that serves Southern New Hampshire. CART takes residents to Manchester, 13 miles north, on Tuesdays and Thursdays. “People wouldn’t go into Manchester unless it was for something specific,” notes Hanlon.
The Parkland Medical Center is 7 miles southwest in Derry along State Route 102, and the Manchester-Boston Regional Airport is 17 miles north. Several houses of worship are in the area, such as the nearly 300-year-old Chester Congregational Baptist Church, the Christ Covenant Church and the Fellowship Bible Church.
Horseback riding and swimming in Chester
Horseback riding is a popular pastime in the area, and several area horse farms offer lessons, boarding and training. The Wason Pond Conservation and Recreation Area has a beach and baseball fields for pick-up games, and hiking trails encircle the pond. There is also a playground in the area, along with a small beach area, and leashed dogs are welcome. Fishing is allowed on the pond, but no motorized boats are permitted, and ATVs, snowmobiles and motorcycles are prohibited in the conservation area. Near Chester Academy is the Chester Skatepark, which has a basketball, baseball and soccer field, and a skatepark. Just outside Chester is the Hidden Valley RV & Golf Park, 7 miles away, which is a campground with a swimming pool and an 18-hole golf course that is open to the public. In the summer, many head to North Hampton State Beach, 31 miles away, to swim, boat, camp and hike.
Shopping and dining along State Route 121 and Derry
Along State Route 121, the Olde Post Restaurant offers American comfort food in a rustic setting. Next door, Center Scoop is a locally owned ice cream shop serving soft serve and specialty ice creams. Also along Route 121 is the Chester General store, which sells groceries and has a deli and house-made take-and-bake pizzas. The Hazelton Orchards is a farm stand that sells seasonal fruits, fruit products and vegetables. For groceries and more shopping and dining, residents head into Derry, which has several strip malls lining Manchester Road, including the Derry Meadows Shoppes, which has a Hannaford. Also in Derry, shoppers will find a Dollar Tree and a Walmart Supercenter, as well as other big-box retailers and chain restaurants.
Residents enjoy the well maintained greenhouse at Osborne's Farm & Garden Center just a short distance from Chester.
The local Market Basket in Hooksett is a choice option for groceries near Chester.
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Events at the Chester Public Library
The Chester Public Library hosts events throughout the year, including several book clubs and DIY art events. The library also partners with local organizations to host events like the Annual Community Pet Show in July, when residents can show off their furry family members. In August, residents set up yard sales outside their homes for Chester's Town-Wide Yard Sale, which helps fund the library’s programming.
The Chester Public Library has been servicing the community for over forty years.
Residents of Chester will find several houses of worship in the area.
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Written By
Isabella Pontecorvo
Photography Contributed By
Joan Wall
Video By
Joan Wall
Interested in learning more about homes in this area?
Reach out to
Andrea Delahunty,
an experienced agent in this area.
GreatSchools:
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On average, homes in Chester, NH sell after 33 days on the market compared to the national average of 56 days. The median sale price for homes in Chester, NH over the last 12 months is $677,983, up 2% from the median home sale price over the previous 12 months.
Most ranch homes play it safe. This one doesn't.Tucked at the end of a cul-de-sac with conservation land bordering the back and one side, 51 Colby Farm Road was built for people who actually thought about how they wanted to live — and then built it that way.The double-sided gas fireplace is the first thing that stops you. Open to both the living room and dining room, it's the kind of
Some homes check boxes. This one rewrites the list entirely.32 Colby Farm Road is a 5,100 sq ft modern farmhouse on a pristine acre in one of Chester's most exclusive new subdivisions. From the sweeping farmers porch to the last carefully chosen finish, every detail tells you this one is different. Inside, 9-ft ceilings, hardwood floors, a custom coffered 10-ft ceiling in the family room, and
Back on Market due to buyer financing, this will go quickly! Investors, flippers and DIY enthusiasts, here is your opportunity to bring this magnificent Federal Colonial back to life! Located in picturesque Chester and built in 1795, this home offers over 3500 square feet of historic charm. Fireplaces adorn many of the rooms, and you’ll find unique features such as built-in cabinets and
Collectors, auto or motorcycle enthusiasts or those needing an ADU take notice! Classic Country Colonial with Farmers Porch on lovely almost 6 acre lot; Sunroom with gas fireplace, cathedral ceiling and fan; Combination Dining/Kitchen with induction cooking stove and plenty of cabinets, fan and hardwood flooring; 1st floor Half bath with laundry; Formal Dining Room with wainscoting and hardwood
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
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$20,000 July Price Drop! 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
50K PRICE CUT! OPEN HOUSE | 11AM to 1PM | Sunday, July 26th, 2026 Welcome to 88 Crawford Road, a breathtaking residential haven nestled in the heart of Chester, New Hampshire. The PropertyThis exquisite colonial estate seamlessly blends sophisticated architectural design with the tranquil beauty of its lush, private surroundings. Offering an expansive 3,675 square feet of meticulously crafted
Zachariah OjaRealty One Group Next Level- Portsmouth
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. Welcome to 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
Catherine ZerbaKeller Williams Gateway Realty/Salem
Enjoy all that Derry has to offer after moving in to this beautifully updated and freshly painted 2 bedroom townhouse! Enter into the sun-drenched living room which features durable vinyl plank flooring and loads of natural light. Round the corner into the bright and airy kitchen which boasts ample cabinetry and a lovely eat-in area. Upstairs you'll find generously sized bedrooms accompanied by a
Laura BaliestieroColdwell Banker Realty Westford MA
Antique colonial home. Country location. Formal living room with wood stove, formal dining room or family room, large eat in kitchen with pantry. 3+ bedrooms up 3/4 bath./ First floor laundry room. FHA-Oil. Credit check, back ground check and references for all occupants over 18 years of age are required. Tenant is responsible for the Electric-Fuel-Cable - snow removal and lawn mowing.The tenant
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