Chesterfield Homes under $750,000

Welcome to Chesterfield, New Hampshire, a picturesque town nestled in the heart of Cheshire County. Known for its stunning natural beauty and rich history, Chesterfield offers a perfect blend of serene rural living and vibrant community spirit. With its rolling hills, lush forests, and tranquil lakes, this charming town is an ideal retreat for nature lovers and outdoor enthusiasts alike.

Chesterfield is not just about breathtaking landscapes; it boasts a strong sense of community with friendly neighbors and local events that bring residents together. The town’s small population fosters a close-knit atmosphere, where you can enjoy the peace of country living while still being just a short drive away from the bustling towns of Keene and Brattleboro.

For those looking to make Chesterfield their home, you’ll be delighted to discover a variety of beautiful residences available for under $750,000. Whether you're seeking a cozy cottage, a spacious family home, or a contemporary retreat, Chesterfield has something to fit every lifestyle and budget. These homes often feature charming architectural details, expansive yards, and proximity to local amenities, ensuring that you can enjoy both comfort and convenience.

Explore the vibrant real estate market in Chesterfield, where you can find your dream home surrounded by the beauty of New Hampshire’s landscapes. With its affordable housing options and welcoming community, Chesterfield is not just a place to live, but a place to truly call home. Come and experience the magic of Chesterfield for yourself!

Newest Chesterfield Homes under $750,000

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

$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

$639,000

3 Beds ⋅ 3 Baths ⋅ 5096595 MLS

Nestled in the picturesque hills of Chesterfield, New Hampshire, this remarkable property offers an unparalleled living experience. Imagine waking up to breathtaking panoramic views that stretch for 90 miles into the mountain landscapes of Vermont, culminating in spectacular sunsets that paint the sky each evening. This home isn't just a residence; it's a front-row seat to nature's most stunning performances. Step inside and discover a thoughtfully designed interior boasting three spacious bedrooms and two and a half bathrooms. The open-concept living areas flow seamlessly, creating an inviting atmosphere perfect for both quiet evenings by the gas fireplace, a space for large family dinners, or entertaining in the open living room. The recently remodeled kitchen, complete with newer appliances, is a chef's dream, offering both functionality and style. Adjacent to the main living space, a relaxing, warm, and welcoming sunroom provides a serene retreat. Enjoy year-round access with lots of sunlight, spectacular views and direct access to the expansive deck where you can entertain guests or simply unwind while soaking in the magnificent vistas. Beyond the main living areas, this home continues to impress with a finished basement, offering additional versatile space for a home office, gym, or recreation room. Practical amenities like an on-demand generator ensure comfort and convenience, and ample storage throughout the property keeps everything organized. Outside, the custom landscaping is a true work of art, featuring over 5 acres, charming flowering trees, meticulously maintained bushes, and classic New England stonewalls, all reflecting a true testament to pride of homeownership. This property has been lovingly cared for, ready for its next chapter with you. Perfectly located between Brattleboro Vt and Keene NH, this property offers quick access to shopping, restaurants, highways, schools, and pristine Spofford Lake. Come see it today before it's gone.

78 Wellington Dr, Chesterfield

$600,000

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

$689,000

2 Beds ⋅ 3 Baths ⋅ 5091566 MLS

Welcome to lake living at its finest! This beautifully maintained 2-3 bedroom, 3 bath home offers sweeping views of picturesque Spofford Lake and is just a short walk to two local beaches. Whether you're looking for a year-round residence, vacation getaway, or an investment opportunity for Airbnb/rental income, this property offers endless possibilities. Inside, you’ll find a fully applianced kitchen, dining area, spacious living room, great room, study, and a 3/4 bath on the main level. The upper floor features 2-3 spacious bedrooms and a full bath, while the lower level offers a recreation room, laundry area, workshop, and an additional 3/4 bath. Enjoy stunning lake views from both inside and outside the home, complemented by soaring 14-foot cathedral ceilings, beautiful oak hardwood floors, and a spacious deck perfect for relaxing or entertaining. The large backyard is ideal for hosting summer gatherings, and the 20x12 heated storage building provides excellent additional space for hobbies, storage, or workshop use. Lower level can be finished to add more living space already plumbed, heated and framed. Conveniently located near public 2 beaches, shopping and restaurants, and just approximately 15 minutes to Keene and Brattleboro with easy access to I-91. Winter sports, skiing at Mount Snow, Parker Mountain, Killington and Granite Gorge to mention a few. Don’t miss this opportunity to own your slice of lake life, schedule your showing today!

495 N Shore Rd, Chesterfield

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