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

$974,900

4 Beds ⋅ 3 Baths ⋅ 5113494 MLS

Welcome to your dream Colonial in the charming Village of Spofford, NH, just moments from Spofford Lake. Enjoy peekaboo lake views from this beautifully maintained 4-bdrm, 3-bath home, where detailed craftsmanship and thoughtful upgrades shine in every room. Highlights include: Four spacious bedrooms (one on first floor), 3-car garage, classic colonial architecture with timeless curb appeal, whole house generator for year-round peace of mind. From the moment you arrive, the care and quality are unmistakable. Whether hosting holiday gatherings, riding out a winter storm in comfort, swimming, boating, fishing, sunset strolls or catching a glimpse of the water from home, this property delivers style, security and lasting value. Homes like this don’t last. Schedule your private showing today!

363 N Shore Rd, Chesterfield

13 B, BA, L20 & Farr Unit 13 B, BA, L20 & M13 B, L A11 & A11-1, Chesterfield

$645,000

3 Beds ⋅ 3 Baths ⋅ 5112527 MLS

Do not miss the opportunity to get this new "To Be Constructed" home under contract with over 9 acres of land with direct brook access for a spring build. You can choose the plans provided for this three bedroom 1700+/- square foot cape or work with the builder to adjust the size and style of the home to be built in the spring. The builder has done capes and ranches in the area with various sizes and has plans for a colonial as another option. An adjacent Ranch is currently being built with the ability to tour the design and quality of the build with an appointment. Enjoy this home with the primary bedroom, closet and en suite on the first floor along with the laundry, half bath, open dining room and kitchen with direct entry from the two car garage. The living room has easy access to the front entry and stairway to the two generously sized bedrooms with walk in closets and shared full bath on the second floor as well as an office. Enjoy the deck off the dining area for great extended living and front entry that welcome you into the home. This location allows you to access the near by boat launch on the Connecticut River and town beach on North Shore Road and public boat launch on Spofford Lake.

13 B, BA, L20 & Farr Unit 13 B, BA, L20 & M13 B, L A11 & A11-1, Chesterfield

$435,000

3 Beds ⋅ 2 Baths ⋅ 5111996 MLS

Set among the hills of Chesterfield, 21 Split Oak Circle offers a peaceful setting, beautiful mountain views, and a glimpse of Spofford Lake as you make your way up Pinnacle Springs Rd. Perched atop the hill on 1.27 acres, this well-loved property combines privacy, mature landscaping, and thoughtful updates with plenty of space to enjoy both inside and out. Step inside to a bright and airy great room that welcomes you into the home and provides a comfortable living space with an easy connection to the kitchen. Upstairs, you will find three bedrooms and a full bathroom, offering a convenient layout for everyday living. The finished lower level adds even more flexibility with a bonus room that could serve as a home office, workout space, hobby room, or whatever best fits your needs. A half bath and direct access to the basement garage add to the functionality of this level. Outside, the property continues to impress with mature landscaping, a large wrap-around driveway lined with fruiting pear trees, and additional fruiting trees throughout the property. Three separate outbuildings provide excellent storage or the opportunity to create a garden shed, workshop, hobby space, or other outdoor retreat. The home has been thoughtfully maintained over the years, with a brand-new PVC membrane roof and freshly painted exterior, including two of the outbuildings. Offered to the market for the first time in 30 years, this is a special opportunity to make a well cared for Chesterfield property your own. Whether you are looking for a full-time home, a peaceful retreat, or simply a place where you can enjoy the beauty of the Monadnock Region, 21 Split Oak Circle is ready for its next chapter. Just 15 minutes to both Keene, NH and Brattleboro, VT. Don't miss the Open Houses this weekend. Friday 10/02 from 4:30pm - 6:30pm and Saturday 10/03 from 11am-1pm!

21 Split Oak Cir, Chesterfield

$432,000

3 Beds ⋅ 2 Baths ⋅ 5111438 MLS

There’s something special about a home that has been loved by the same owners for 45 years. Built in 1860, this 3-bedroom, 2-bathroom home offers a wonderful combination of historic character, comfortable updates and space to make your own. Step onto the inviting wraparound front porch before heading inside, where wood floors and a wood stove add warmth and classic New England charm. The updated kitchen features granite countertops and a gas stove, while a spacious, recently renovated first-floor bathroom includes a walk-in shower and conveniently located laundry. Mini-split provide cooling during the warmer months, and an automatic generator offers added peace of mind year-round. Outdoor spaces include a composite side deck and a newly paved driveway completed in 2025. One of the property's most intriguing features is the attached walk-up barn/garage/woodshop with a metal roof. Whether you envision a workshop, studio, hobby space or simply exceptional storage, there's plenty of room for possibilities. The barn may also offer potential for future conversion to additional living space with appropriate town approvals. Enjoy being close to Spofford Lake and all the recreation and natural beauty the area is known for, while remaining conveniently situated between Keene, NH and Brattleboro, VT. With more than 160 years of history behind it, this well-loved Spofford home is ready for someone new to make it their own.

513 N Shore Rd, Chesterfield

$799,000

3 Beds ⋅ 3 Baths ⋅ 5110466 MLS

Nestled at Spofford Lake, New Hampshire, this custom-built masterpiece offers an unparalleled blend of rustic charm and modern luxury. With exclusive, privately owned lake and dock access, this home is a true New England dream, promising a year-round, relaxing lifestyle, of serene beauty and outdoor adventure. Step inside to discover an open-concept living space with natural light, where the warmth of "cove style" wooden, bead board ceilings create an inviting atmosphere. The kitchen is where the heart is and allows for meaningful conversations at the kitchen island or breakfast nook. This meticulously designed home boasts, beautiful hardwood floors, 2 warm pellet stoves, 3 spacious bedrooms and 2.5 baths, each detail reflecting a commitment to quality and comfort. The upstairs bathroom conveniently offers easy access laundry, so no lugging your linens up/down stairs. In the basement you'll love the extra space for workout room and a private, direct walk-out, office to complete all your work projects. The exterior, adorned with classic wood shake siding, perfectly complements the stunning seasonal lake views that greet you from various vantage points. Every inch of this property, from the intricate woodwork to the well-maintained utilities, speaks volumes about the care and craftsmanship invested in its creation. This isn't just a house; it's a beautifully refined New England HOME, ready to captivate the heart of any discerning homeowner. Just a 2-minute walk to your private dock space and sandy beach common area where you can enjoy breathtaking sunsets or hit the water for all your watersport entertainment. Located just minutes from major shopping, restaurants, highways, ski areas, and lots of biking/hiking/snowmobile trails. Come see the Lake Life Living at it's best.

17 Echo Cv, Chesterfield

$559,000

3 Beds ⋅ 2 Baths ⋅ 5108383 MLS

Set on 2.29 acres in Spofford, this inviting three-bedroom home offers flexible living space, a fully fenced yard and an oversized heated two-car garage-plenty of room for everyday life, projects and storage. Inside, the open-concept kitchen, dining and living area feels bright and comfortable, with updated windows, laminate flooring and an electric fireplace adding warmth to the main gathering space. The kitchen features a new electric range and dishwasher. Walk right out from your dining/living area to a large side deck that connects to a 3 season porch, the perfect spot to unwind, be creative, add a hot tub or anything else you can imagine! The main level includes two bedrooms, a full tiled bath and a primary suite with two closets and a private 3/4 bath. Downstairs the finished space expands the possibilities with a tiled bonus room, a separate office or home gym, laundry area and convenient walkout access. Enjoy the outdoors from the side porch or three-season porch overlooking the fenced yard. Additional features include central vacuum, a 200-amp electrical panel, sump pump, carport and a new roof on the garage! With useful indoor and outdoor space and easy access to Spofford Lake, Keene and Brattleboro areas, this Spofford property is ready for its next chapter.

205 Sugar Maple Ln, Chesterfield

$379,900

3 Beds ⋅ 2 Baths ⋅ 5106922 MLS

Motivated Seller, here is your chance to Chesterfield and enjoy all this town has to offer! 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. (complete with an EV Charging station) 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 9, Chesterfield

$419,900

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

$475,000

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

$699,900

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

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