Cheshire County, NH 6+ Bedroom Homes for Sale

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Newest Cheshire County, NH 6+ Bedrooms Homes for Sale

$5,999,000

13 Beds ⋅ 10 Baths ⋅ 5097639 MLS

A stone pillared entry drive by a mature rhododendron and mountain laurel hedges leads to Knollwood... a singular country estate set in the heart of New Hampshire's Monadnock region. A compelling opportunity to acquire a legacy property at a fraction of its replacement cost and on 100+ acres. Built in 1900 by Franklin MacVeagh, U.S. Secretary of the Treasury, and later owned by Ernest Henderson, founder of Sheraton Hotels, the estate has had only two owners in 124 years. From 1910-1913, President William Howard Taft used Knollwood as his occasional Summer White House, while Mark Twain spent weeks here reading Huckleberry Finn to guests... Set on a ridge of Mount Monadnock with sweeping 40-mile views, the property spans 100+ acres of gardens, forests, and vineyard—an increasingly rare offering in the Northeast. The 14,500+ sq ft Georgian residence includes 13 bedrooms, 9.5 baths, a 26-seat dining room, library, terraces, and a 120-person ballroom. Additional structures include a heated 3-car garage with apartment above and a historic barn... In addition to its appeal as a one-of-a-kind grand residential estate, Knollwood’s scale, layout, and global narrative position it for luxury retreats, weddings, or boutique hospitality ventures (subject to approvals)—offering a significantly lower basis than comparable New England opportunities. Located less than 2 hours from Boston and ~20 minutes from a private jet airport, this is a rare opportunity to acquire, reposition, and create a destination asset of lasting significance. Proof of funds required...showings by appointment only please.

4 Windmill Hill Rd, Dublin

Listing courtesy of Andrew Peterson from Four Seasons Sotheby's International Realty. ()

$699,000

6 Beds ⋅ 6 Baths ⋅ 5093058 MLS

Country living at its finest! Nestled on 15 private acres, this expansive farmhouse offers the perfect blend of rural charm, versatility, and modern convenience. Weather your seeking a peaceful homestead, multi-generational living, or a property ideal for animals and hobby farming, this exceptional estate delivers. This property features a spacious main farmhouse, separate guest suite, along with a separate accessory dwelling unit. This property provides excellent flexibility for extended family, guest, rental income or a home-based business. The ADU is handicap accessible and includes a functional stair chair, offering enhanced accessibility and comfort. Outside you will find ample open space for horses, livestock, gardening or simply enjoying the privacy and beauty of the countryside. Mature fruit trees, raspberry bushes and grape vines for homemade treats await you. Enjoy the view from your covered porch that overlooks the pond and sprawling flat acreage that truly creates a special setting. Relax and entertain with the pool at your feet and enjoy the hot tub for the brisk winter weather. A rare opportunity to own a private country retreat with room to grow, explore and enjoy the lifestyle you have been dreaming of. Benefit from land in current and receive a property tax reduction. Walking distance to class VI road, great for snowmobiling, ATVs horseback riding or a nature walk. SHOWINGS START AT THE OPEN HOUSE 6/13/26 11:30AM-1:30PM

360 Jaffrey Rd, Marlborough

Listing courtesy of Katelyn A Heaney from Greenwald Realty Group. ()

$390,000

6 Beds ⋅ 3 Baths ⋅ 5079870 MLS

Located just a short walk from the town beach on Contoocook Lake, this spacious 6-bedroom, 3-bath home offers the opportunity to enjoy a relaxed lifestyle close to water, nature, and town conveniences. Set on a level 1.05-acre lot with generous yard space, there’s plenty of room for outdoor gatherings, gardening, or simply enjoying the open space. Originally a single-story home, the property was expanded into a two-story Colonial in 2013, creating a versatile layout with three bedrooms on each level—ideal for hosting guests, multi-generational living, or creating dedicated home office and hobby spaces. The main living area features a cozy wood stove with hearth, perfect for cooler seasons, and flows into a pass-through dining room and kitchen that invite connection and everyday living. Upstairs, the primary suite includes a walk-in closet and ¾ bath, along with the convenience of second-floor laundry. A walk-up attic adds additional storage or potential for future use. Enjoy easy access to downtown Jaffrey’s local shops, schools, restaurants, and community amenities, along with nearby outdoor recreation including trails and Mount Monadnock. Property is being sold as-is.

139 Squantum Rd, Jaffrey

Listing courtesy of Jill Exel from BHG Masiello Keene. ()

$575,000

6 Beds ⋅ 4 Baths ⋅ 5077952 MLS

Tucked away on a quiet hilltop, this charming home offers the perfect escape with views over the Connecticut river and mountains afar. A 900-foot private driveway welcomes you home with many opportunities any spacious parking. Designed with true first floor living, the main residence offers everyday functionality without compromise. Expansive windows flood the home with natural light. The open layout flows seamlessly for comfortable living and effortless entertaining. Step outside your own private oasis-featuring a stone patio, charming screened in gazebo, and relaxing hot tub. This home is also equipped with solar panels, helping reduce energy costs while supporting sustainable living. Adding even more versatility, the attached dwelling unit provides ideal space for multigenerational living, extended guest, a private office, or rental income potential which is currently in place. Primary residence and ADU have separate entrances, utilities and both have full basements. Do not miss out on this amazing opportunity, there is so much to see!

89 Butler Ave, Hinsdale

Listing courtesy of Katelyn A Heaney from Greenwald Realty Group. ()

$1,995,000

6 Beds ⋅ 6 Baths ⋅ 5067451 MLS

***SUBSTANTIAL PRICE IMPROVEMENT! Never before lived in, this extraordinary Connecticut River estate offers a rare opportunity to own 18± private acres and 1,200± feet of pristine river frontage, complete with a sandy beach and breathtaking views. One of the last remaining undivided waterfront parcels of its kind, this newly constructed 6,400± sq ft residence blends luxury, privacy, and natural beauty in an irreplaceable setting. Designed for both everyday living and exceptional entertaining, the home features 6 bedrooms, 6.5 baths, and an accessory dwelling unit with a private entrance—ideal for multigenerational living, guests, or extended stays. Thoughtful craftsmanship is evident throughout, including 3/4” oak flooring, Marvin windows, porcelain-tiled baths, and custom cabinetry. Whether launching a boat from your shoreline, enjoying sunsets over the river, or hosting family and friends in a truly remarkable setting, this property delivers an unparalleled lifestyle rarely found in New England. A one-of-a-kind waterfront estate offering a legacy property for generations to come. A seller credit will be provided at closing for kitchen, bathroom, and closet accoutrements, offering the opportunity to personalize the finishing touches to suit your own taste and style. Competitive seller financing options available. Just 5 minutes from Brattleboro and I-91 and only 15 minutes from Keene.

30 Farr Rd, Chesterfield

Listing courtesy of TJ Kelly from Greenwald Realty Group. ()

$2,400,000

7 Beds ⋅ 7 Baths ⋅ 5061882 MLS

A Legacy Estate Rich with History and privacy! This Exquisite Asher Benjamin Greek Revival built in 1812 has more than 8,000 square feet across 24 rooms and 11 private acres with woods, mature plantings and a secret walled garden located at the south end of Main Street in Walpole NH. Memorable gatherings and holidays are assured with 10 fireplaces, 8 bedrooms (most with en-suite baths), high ceilings, original wide plank wood floors, glass windows and ornamental millwork, while the modernized tile bathrooms and heating system ensure comfort. The home's formal dining room, elegant library/den, and 2 sitting rooms set the stage for grand entertaining. One parlor showcases rare original "Monuments of Paris" hand-painted Dufor wallpaper also hanging at the Winterthur Museum and the Metropolitan Museum of art. The family-sized kitchen is a cook's dream with premium appliances, two ovens and a separate baking area. Direct kitchen access to a large, screen porch guarantees maximum family dining enjoyment whatever the season. This home is central to the history of Walpole, and its grandeur has only grown with time. Out front there is a majestic yellowwood tree, one of the oldest and largest in New England, planted in 1855 by Frederick Newman Knapp to honor his marriage. It brings breathtaking color in the fall and offers a forty-foot span of shade in the summer. Modern creativity also has a place here: a professional recording studio, complete with equipment elevator and direct garage access, opens doors for musicians, podcasters or producers seeking a dedicated workspace. The layout of the home lends itself to multigenerational living and guest accommodations. From grand entertaining to quiet reflections, this property has been an oasis for more than 200 years.

31 Wentworth Rd, Walpole

Listing courtesy of Kathryn A Beam from Galloway Real Estate LLC. ()

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