Chesterfield Real Estate

Welcome to Chesterfield, New Hampshire—a hidden gem nestled in the heart of Cheshire County. This picturesque town boasts a rich history and a vibrant community, making it an ideal place for those seeking tranquility and charm. With its stunning natural landscapes, Chesterfield is surrounded by lush forests, serene lakes, and rolling hills, offering endless opportunities for outdoor enthusiasts.

Chesterfield is known for its welcoming atmosphere and tight-knit community, where neighbors become friends and local events foster connections. The town hosts a variety of seasonal festivities, from summer fairs to winter celebrations, ensuring there’s always something happening. The local schools are highly regarded, providing quality education and a nurturing environment for families.

For those who appreciate the arts, Chesterfield offers a range of cultural experiences, including galleries and local theater productions. Nature lovers will find themselves at home here, with ample hiking trails, fishing spots, and parks that invite exploration and relaxation. The nearby Connecticut River adds to the town’s scenic beauty, providing opportunities for kayaking and fishing.

Conveniently located just a short drive from the bustling towns of Keene and Brattleboro, Chesterfield combines the peace of rural living with easy access to urban amenities. Whether you’re looking to settle down in a cozy cottage or a spacious family home, Chesterfield offers a variety of real estate options to suit your needs. Discover the warmth and charm of Chesterfield, where community spirit thrives and nature’s beauty surrounds you. Your dream home awaits in this enchanting New Hampshire town!

Newest Listings in Chesterfield

$389,900

3 Beds ⋅ 2 Baths ⋅ 5106922 MLS

Welcome to 1750 Route 9 Chesterfield NH. Filled with lots of natural light and plenty of space, this 3 bedroom, 2 bath home is ready for new owners to bring their vision and make it their own. The home features a large pantry, hardwood floors, convenient second floor laundry and 2- car garage. The property previously featured an apartment on the 2nd floor, providing potential for additional living space for extended family, guests or rental income. This classic farmhouse is set on 3 acres in a country setting with plenty of land to enjoy outdoor activities and privacy. Just a short drive away is scenic Spofford Lake, known for its great fishing, water quality and water sports. Chesterfield Gorge is an even shorter drive away and is an excellent for short hikes and / or picnics. Nicely situated between both Brattleboro VT and Keene ( about 10 minutes either way )

1750 Rte 9th Rte, Chesterfield

$449,900

3 Beds ⋅ 2 Baths ⋅ 5105943 MLS

Storybook charm in the sweet village of Spofford! Tucked behind a welcoming picket fence and an enchanting English-style garden, this delightful 3-bedroom, 2-bath Antique Cape is filled with warmth, character and unexpected surprises. Step inside to beautiful wide pine floors and an adorable eat-in kitchen featuring granite counters, recessed lighting and even a secret pantry! Just off the kitchen is a ¾ bath with a custom tiled shower. The inviting front living room, complete with a cozy pellet stove, is the perfect place to settle in on a chilly New England evening. The spacious family room addition, added in 1992, may quickly become your favorite room in the house! With plenty of space for a large dining table and comfortable sitting area & wood stove, it was made for gathering with family and friends. Sliders open to the deck overlooking the cozy side yard—perfect for summer dinners, morning coffee and entertaining. Upstairs, the primary bedroom is simply enchanting, with a wonderful cottage-style feel that you are sure to fall in love with. You'll also find an office area, full bath with tiled floor, and an additional bedroom with charming built-ins. And then there are the extras that make this property truly special! A whimsical cottage shed with a loft and sleeping quarters creates the sweetest little escape—grab a good book, sneak away for an afternoon nap or simply enjoy your own private hideaway. Nearby, a cozy fire pit area is ready for summer nights under the stars. The large garage offers yet another bonus: a studio apartment, (currently rented), providing an opportunity for additional income or flexible space for extended guests. All of this is just minutes from beautiful Spofford Lake, the Spofford Post Office and a short drive to Keene. This isn't just a house, it's a chance to slow down, settle in and enjoy the charm of village life. Come experience a simpler way of living…the way it was meant to be.

37 High St, Chesterfield

$485,000

2 Beds ⋅ 2 Baths ⋅ 5104430 MLS

Storybook Craftsman on 1.5 Parklike Grounds. This former residence of the childrens' author Charles Tazewell was completely renovated in 2017. Elegant one floor living with beautiful finishes. Granite countertops and stainless steel appliances with pantry cupboards in the kitchen. All systems have been updated. A gazebo with ceiling fan and light compliments the stunning landscaping. Two car garage and central AC round out the property amenities. Convenient to both Keene and Brattleboro.

7 Winchester Rd, Chesterfield

$849,900

3 Beds ⋅ 3 Baths ⋅ 5104307 MLS

Charming Colonial Retreat on 12+ Private Acres Welcome to your ultimate private sanctuary! This beautiful 3-bedroom, 3-bathroom Colonial offers the perfect blend of modern convenience, space, and tranquil living. Nestled on a sprawling 12.1-acre lot, this home provides exceptional privacy while remaining ideally situated near the Vermont and New Hampshire borders for easy commuting, dining, and outdoor recreation. Inside, you’ll find a bright and airy open-concept layout designed for seamless everyday living and effortless entertaining. Showings will begin on August 17th 2026.

131 Friedsam Dr, Chesterfield

$1,125,000

3 Beds ⋅ 3 Baths ⋅ 5103600 MLS

A home 250+ years in the making, has just been offered for the first time! A perfect representation where classic New England style meets brand new modern convenience and elegance. This 3-bedroom, 2.5-bath home features high end finishes, historic displays of craftsmanship, and an incredible vision that makes this house a home. The outside features field stone siding and harmonious landscaping all on a sprawling private parcel of 6.6 acres. Yes, you also have your very own, perfectly manicured, apple orchard, an oversized 3 car garage with ample additional storage, a gazabo, trellis, and much more. Inside you'll find a vaulted ceiling in the chef inspired kitchen featuring high end appliances, custom wood cabinets, center island, and farmhouse style sink. Just off the kitchen you'll start the day enjoying your morning coffee, reading the paper, or watching the news in the wrap-around breakfast nook. The main living space is primarily on one floor with a large ensuite bedroom boasting hand hewed beams, wide plank flooring, large windows, vaulted ceiling, ceiling fan, and 2 large walk-in closets; all finished with a perfect touch in the spa style bathroom. The warm living room offers a stone fireplace, built-in bookshelves and ample sunlight. The dedicated dining room has a secret pass-through to the kitchen sure to impress any dinner guests. Upstairs you'll be amazed with the guest bedroom and incredible lines of the adjoining bathroom. This private space offers guests a soaking tub, walk-in shower and plenty of impressive design features. The finished basement offers even more space to relax and unwind, this space could be a private office, media room, workout room, or just an extra TV room. Located perfectly between two large towns, your shopping and restaurant needs are just minutes away. Close to beautiful Spofford Lake, ski areas, hiking/walking/snowmobile trails, and easy access to highways. THIS HOME IS AN ABSOLUTE MUST SEE!

3 Apple Hl, Chesterfield

$899,000

4 Beds ⋅ 2 Baths ⋅ 5101977 MLS

YES!!!! that's right, TWO homes on 1 Parcel. Imagine the possibilities of having 2 homes on beautiful Spofford Lake. Come see the Rustic Charm of these classic, seasonal cottages. There certainly aren't many original vacation homes left on the lake, take advantage of owning (2) of your very own. The "Lakeside Cottage" is just a few feet from the water's edge where you can walk across the sand and dip your toes in the pristine, sandy bottom, clear water. Enjoy waterfront views and easterly sunrises from your enclosed porch as you enjoy your morning coffee. The lake front cottage also offers all the necessities of a cozy kitchen, living room with stone fireplace, 3/4 bathroom and two upstairs bedrooms to re-energize for the next day's lake excitement/activities. The "Roadside Cottage" sets only a few feet behind and is equally as charming. It also has views to the lake, use it as a guest home, rental property, or extra family space. This cottage features an enclosed porch, vaulted ceilings, brick fireplace, a loft, one downstairs bedroom, 3/4 bathroom and an upstairs bedroom. Each cottage features a time capsule of history, just waiting for your family to make more memories at Spofford Lake. Brand new septic system installed 2023 servicing both homes, updated 100amp electrical services, and new retaining wall on lake front cottage. Did I mention the convenient location? Easy access from Rte91, and just minutes from major shopping, restaurants, and grocery stores and more. See you at the Lake!

142 N Shore Rd, Chesterfield

$420,000

3 Beds ⋅ 2 Baths ⋅ 5101873 MLS

Nestled along a quiet country road in desirable Chesterfield, this classic Cape-style home offers the perfect blend of timeless charm and thoughtful updates. Set on 1.4 beautifully landscaped acres, the property overlooks a picturesque pond and open meadow, creating a peaceful setting you'll enjoy year-round. Inside, natural sunlight fills the spacious living areas, highlighting the hardwood floors and warm, inviting character throughout. The flexible floor plan offers 3 bedrooms, a formal dining room, a comfortable living room with a cozy hearth and gas stove, plus a convenient first-floor laundry room and half bath. Classic details preserve the home's original charm while newer windows, vinyl siding, and an architectural shingle roof provide peace of mind. Step outside to enjoy the tranquil surroundings from the deck overlooking the backyard, where mature landscaping, open green space, and scenic views create the perfect backdrop for relaxing or entertaining. An attached one-car garage, drilled well, private septic, and easy access to Keene, Brattleboro, and nearby Spofford Lake make this property as practical as it is beautiful.

95 Poocham Rd, Chesterfield

$665,000

4 Beds ⋅ 3 Baths ⋅ 5096591 MLS

Welcome to the heart of Spofford, where small-town charm meets one of New Hampshire's most desirable lake communities. Just minutes from Spofford Lake, this classic Cape offers a lifestyle that's increasingly hard to find. Start your mornings with coffee on the balcony overlooking the lake's peaceful inlet, spend summer afternoons at the town beach, and unwind in the hot tub at day's end. A standout feature is the stunning office in the barn. Warm wood walls still carry the welcoming scent of natural timber, creating an inspiring workspace with a private balcony overlooking the lake inlet. Inside, history and modern updates blend beautifully. The eat-in kitchen features granite countertops, an island, large pantry, and access to the private deck. Enjoy a bright sunroom, curl up with a book in the library with built-in bookshelves, formal dining room with fireplace, and convenient first-floor office and half bath. Upstairs offers three bedrooms, two full baths, laundry room, walk-in attic storage, and a flexible office or fourth bedroom. The level yard is bordered by classic stone walls and includes the lot across the street with apple and pear trees plus overflow parking. Improvements include triple-pane windows, well, septic system, oil tank, mini-splits, wood stove, sunroom, updated kitchen, EV charger, and a security system. Residents enjoy access to the Spofford Lake town beach, known for its clear waters, boating, fishing, and swimming. Conveniently located just 10 minutes to Keene and 15 minutes to Brattleboro, VT, this home offers the perfect balance of peaceful lake living with easy access to shopping, dining, healthcare, and entertainment. Rich in history, full of character, and thoughtfully updated for today's lifestyle, this is more than a home, it's a place to put down roots and enjoy everything the Spofford community has to offer.

373 Rte 9a, Chesterfield

$325,000

3 Beds ⋅ 2 Baths ⋅ 5095623 MLS

Welcome to 205 Route 9 in Chesterfield, NH, a home designed for easy living. This inviting ranch combines the convenience of a single-level floor plan with valuable updates, including a newer metal roof (2020), Harmon pellet stove, and updated appliances. Downstairs, the finished bonus room provides flexibility that's hard to find. Use it as a playroom, home office, workout space, game room, or whatever best fits your lifestyle. It's a great extension of the home's living area without sacrificing storage space. Outside, the large yard offers plenty of room to spread out and enjoy. Whether you're gardening, entertaining, setting up a fire pit, or just soaking up some sunshine, there's plenty of space to make it your own. Conveniently located just minutes from Keene and a short drive to Brattleboro, this home offers the best of both worlds: easy access to shopping, dining, and commuting routes while still enjoying all that Chesterfield has to offer. With thoughtful updates already completed and room to make it your own, this home is ready for its next chapter.

205 Rte 9, Chesterfield

$295,000

5094216 MLS

Enjoy the sights and sound of the Connecticut River. 2.11 Acres with over 392 feet of water frontage. The land comes with private access to the River making a great site to plan your dream home. When you drive up Mountain Road the lot is on the left with the river on the right. The road dead ends with the access to the trailhead containing a 520 acre trail system that leads to the summit of Wantastiquet Mountain and connects to the Madame Sherri Forest off Mountain Road also. The lot has some shade and sun with young growth, long road frontage, level lot along the road with a tall rock ledge background for privacy. This is a rare find minutes from the Vermont boarder with easy access to Interstate 91, off of Rt 9 within 25 minutes East to Route 9 and 101.

00 Mountain Rd, Chesterfield

$360,000

3 Beds ⋅ 2 Baths ⋅ 5092773 MLS

Welcome to 174 Pond Brook Road, a Contemporary Mountain Chalet nestled on a private, wooded 2.8-acre lot in West Chesterfield. Built in 1977, this unique home offers impressive architectural character, beginning with a wide entry foyer that opens up to a dramatic, three-story barrel stairway. The main living space features soaring vaulted ceilings, a cozy wood fireplace, and massive windows that bring the beauty of the surrounding nature indoors. Seamlessly connected is the galley-style kitchen and a dining bump-out offering panoramic woodland views on three sides. The main level also includes a convenient half-bath and a versatile bonus room, ideal for a home office, den, or main-floor guest space. Upstairs, the open landing and second-floor foyer look down over the living room below, leading to three distinct bedrooms and a large full bathroom. The walk-out lower level is built for functional New England living, featuring a practical mudroom with a separate entrance, a dedicated laundry room, and direct access to the integrated one-car garage. Exterior highlights include a durable metal roof and a spacious wrap-around front deck, perfect for relaxing and watching the local wildlife. Situated with 371 feet of public road frontage in a quiet rural residential area, this property offers a peaceful, private retreat ready for your personal touch. Join us for an open house on Saturday 6/6/26 from 11am-1pm, or schedule your private tour today!

174 Pond Brook Rd, Chesterfield

$888,000

4 Beds ⋅ 3 Baths ⋅ 5092335 MLS

A truly exceptional home offering quality craftsmanship, generous living space, and a private setting with breathtaking mountain views. Thoughtfully designed and impeccably maintained, this stunning property combines elegance, comfort, and functionality throughout. The heart of the home is a chef’s dream kitchen, featuring premium stainless-steel appliances, including a Wolf range and Sub-Zero refrigerator, abundant cabinetry, and beautiful finishes. The kitchen flows seamlessly into the sun-filled great room, where gleaming hardwood floors and a cozy fireplace create a warm and inviting atmosphere for everyday living and entertaining. Step outside to the expansive deck and take in the peaceful mountain views an ideal setting for morning coffee, outdoor dining, or simply relaxing and enjoying the tranquility of your surroundings. The home offers four generously sized bedrooms, including a luxurious primary suite complete with a spacious walk-in closet and a well-appointed en-suite bath. The walkout lower level provides additional finished living space, perfect for a home office, media room, gym, or guest accommodations, along with ample storage space. An oversized garage offers plenty of room for vehicles, recreational equipment, and all your outdoor gear. Located in one of the area's most desirable neighborhoods, just minutes from beautiful Spofford Lake, this home also provides convenient access to both Brattleboro, Vermont, and Keene, New Hampshire. Enjoy nearby shopping, restaurants, healthcare facilities, cultural attractions, theaters, museums, churches, and several colleges, all within easy reach. This remarkable property offers the perfect balance of luxury, privacy, and convenience an extraordinary place to call home.

22 Phillip Dr, Chesterfield

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