Cheshire County, NH 5 Bedroom Homes for Sale

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Newest Cheshire County, NH 5 Bedroom Homes for Sale

$825,000

5 Beds ⋅ 3 Baths ⋅ 5116548 MLS

Unique 53-Acre Property in Sullivan, NH — Your Own Private Country Retreat! Discover an extraordinary opportunity to own 53 acres of beautiful New Hampshire countryside with multiple living spaces and endless possibilities! The 1970 post-and-beam contemporary features 3 bedrooms, 1½ baths, an open-concept living and dining area, sunroom, and full basement. Perched on a hill, the home enjoys fantastic views, while a pond and hiking trails through the woods invite you to explore and enjoy the natural beauty surrounding you. A second home and a 2-bedroom apartment over the garage provide wonderful options for rental income, guests, extended family, or a caretaker. With abundant open land for gardening, farming, and raising animals, this is an ideal setting for those dreaming of a self-sufficient lifestyle. Enjoy absolute privacy and the freedom of country living, yet remain just minutes from Keene's shopping, restaurants, and theater. Approximately 2 hours to Boston and 4 hours to NYC. Don't miss this rare opportunity to own your own piece of New Hampshire paradise! Whether you're looking for a private retreat, a multi-generational property, rental income, or the perfect place to live off the land, this remarkable property deserves your attention. Schedule your private showing today and imagine the possibilities! Open House Saturday, November 7th from 12:30- 2

23 White Brook Dr, Sullivan

Listing courtesy of Nancy Proctor from BHG Masiello Keene. ()

$385,000

5 Beds ⋅ 2 Baths ⋅ 5115907 MLS

Tucked behind the historic Frost Free Library, dating to 1866, is this charming 1876 New England home filled with character and potential. Currently configured as a three-family property, it offers flexibility for an investor, owner-occupant, or buyer looking to create a unique single-family home. The main living space spans two floors, with bedrooms and a bathroom upstairs. The original breezeway to the barn has been converted into a second unit. Renovations were started, leaving the space partially open to the studs and ready for the next owner to bring their vision to life. The third unit is located downstairs and has its own driveway. Each unit has a separate entrance, parking, and electric meter. 2020 main building was re-roofed. A true highlight is the 36' x 36' post-and-beam barn, featuring two floors and a basement, offering plenty of possibilities for storage, workspace, studio space, or more. With its historic charm, versatile layout, impressive barn, and potential for a single-family conversion, this property is truly one-of-a-kind. Come see the possibilities for yourself!

17 Pleasant St, Marlborough

Listing courtesy of Jonathan L Bafundi from Realty One Group Next Level. ()

$1,275,000

5 Beds ⋅ 6 Baths ⋅ 5115065 MLS

From the moment you arrive via the expansive driveway, you are greeted by striking Hardie Board siding, gable rooflines, and a stunning fieldstone wall that gracefully breaks the freshly manicured front lawn into two tiers. Lush annual and perennial flower beds frame the inviting covered front porch, which is beautifully detailed with cedar shake siding, composite decking, and a standing seam metal roof. Boasting over 4,800 square feet of meticulously finished living space, this 2015-built retreat perfectly balances a quintessential rural New England setting surrounded by pure nature with the convenience of being just minutes from the amenities and excitement of Keene, the county's largest city. Step inside to a bright, open-concept floor plan featuring gleaming hickory hardwood floors and a striking double-sided propane fireplace. The spectacular chef's kitchen is an entertainer’s dream, equipped with custom white cabinetry, quartz countertops, a large center island, and stainless steel appliances. The main level offers ultimate flexibility with a convenient first-floor bedroom, while the upper level hosts three additional bedrooms and two full bathrooms—highlighted by a well-appointed primary suite complete with a jetted tub and walk-in shower. In total, the residence offers five generously sized bedrooms (plus bonus spaces) and five-and-a-half bathrooms. A standout feature is the exceptionally spacious, attached Accessory Dwelling Unit (ADU)—perfect for multi-generational living or rental income—boasting a large bedroom, two full bathrooms, a four-season porch, and a bonus room all on the first level. Outside, the private grounds feature mature raised garden beds, a gorgeous paver patio with a hot tub, and direct abutter access to the 42-mile Cheshire Recreational Rail Trail for endless outdoor recreation. This property checks so many boxes its hard not to fall in love, schedule your private showing today!

284 Hurricane Rd, Keene

Listing courtesy of Ross P Doody from Century 21 Highview Realty. (Off: 603-542-7766)

$324,000

5 Beds ⋅ 1 Baths ⋅ 5113130 MLS

A rare opportunity to own a property where historic character, versatility, and an exceptional in-town location come together. Set behind a welcoming front porch, 87 Water Street offers the warmth and architectural details of an earlier era with thoughtful updates for today’s lifestyle. Inside, you’ll find an inviting eat-in kitchen with a distinctive tin ceiling and pantry, wood floors, bullseye molding, updated windows, a thoughtfully preserved original stained-glass window, and an abundance of oversized closets. Original character is thoughtfully woven throughout, creating a sense of warmth and authenticity that is increasingly difficult to find. Tidy, comfortable, and move-in ready, the home also features a newer boiler. The backyard offers ample space for gardening, entertaining, recreation, and outdoor enjoyment. A substantial outbuilding provides exceptional versatility, with generous workshop and storage space, vehicle parking, electricity, and a second floor. The structure has received City of Keene Planning Board approval for conversion to a one-bedroom residential unit, offering valuable potential for additional living space or other uses. Buyer to verify current status, approvals, and permitted use with the City. The location is equally compelling, with downtown Keene, the Co-op, playgrounds, schools, shops, restaurants, and other amenities all within easy walking distance. Enjoy the convenience of an in-town lifestyle with the added space and flexibility this property provides. With its character-filled interior, substantial outbuilding, inviting outdoor spaces, and walkable location, 87 Water Street offers a unique combination of history, functionality, and future potential. Most furnishings may also be available for purchase. Schedule your showing today!

87 Water St, Keene

Listing courtesy of Paul Rodenhauser from BHG Masiello Keene. ()

$1,595,000

5 Beds ⋅ 6 Baths ⋅ 5110896 MLS

A rare opportunity: this extraordinary 1794 Colonial and its four-story barn, set on 30+ acres in the Monadnock region, form one of southern NH's most significant historic properties, a unique blend of period character, land, and privacy, with Mt. Monadnock views. Thirteen rooms across 6,200 sq feet, plus 5 bedrooms (with the option for 4 more) and 6 baths: space for family, homestead, multigenerational living, or reinvention as a venue, inn, or business. Four masonry fireplaces, granite foundation, wide-board floors, and exposed beams carry forward 18th-century craftsmanship. An expansive back deck, covered porch, and balcony extend outdoor living. The barn is the showstopper: a one-of-a-kind, 7,400 sq ft structure built in 1894 with timber from Mt. Monadnock, includes four soaring floors plus a cupola. Its granite foundation, quarried by the original owner, joins a massive granite wall enclosing the paddock. Original horse stalls, a woodworking shop, and finished studio space fill the floors, upgraded with septic and water, in a once-in-a-lifetime chance to preserve barn history. The mature maple-lined driveway leads in from a state route and a local road. 30+ acres divide between open, flat fields and mature woodland, laced with walking paths, a goldfish pond, antique silo, glass greenhouse and raised beds. Keene: 10 min | Manchester Airport: <1 hr | Boston: approx. 2 hrs | NYC: approx. 4.5 hrs 18th-century New Hampshire heritage, ready for its next chapter.

45 Thatcher Hill Rd, Marlborough

Listing courtesy of Sadie Halliday from EXP Realty. (Cell: 603-660-2321)

$599,000

5 Beds ⋅ 4 Baths ⋅ 5107155 MLS

Step into the warmth and character of this distinctive 5-bedroom, 4-bath home, set on 5.8 acres and filled with the timeless details that make an older New England property so special. Exposed timber beams, beautiful wide-plank wood floors, classic paneled doors, built-in cabinetry, and multiple brick fireplaces create an inviting sense of history throughout the home. Generously sized rooms feature an in law suite on the main level plus a primary bedroom suite on the 2nd level offers plenty of flexibility for family, guests, entertaining, or creating dedicated spaces for work and hobbies. The fireplaces serve as striking focal points, while the abundant natural wood and traditional architectural details give the home a warmth and character that is difficult to replicate in newer construction. Updated windows, a new heating system and fuel tanks as well as many other improvements have been done. Outside, the property offers even more versatility with a detached two-car garage featuring an expansive two-level workshop. Whether you're looking for space for woodworking, hobbies, projects, equipment, storage, or a home-based venture, this substantial outbuilding provides possibilities well beyond a typical garage. Come experience the character and possibilities of this special property for yourself.

13 Old Sullivan Rd, Gilsum

Listing courtesy of Robert Inman from RE/MAX Town & Country. ()

$699,900

5 Beds ⋅ 3 Baths ⋅ 5099423 MLS

Discover the ultimate blend of rural serenity and modern luxury in Southwestern NH. Perched at the crest of a hill at the end of a town-maintained road, this meticulous 3,548 sq ft home sits on 5.02 rolling acres wrapped in historic stone walls. Ideal for equestrian or hobby farm enthusiasts, the property features a well-maintained 3-stall shed row barn with electricity, water, and a tack room. Inside, wide-pine floors flow through an expansive layout. The chef’s kitchen boasts custom Shaker cabinets, quartz counters, a Kraus sink, induction cooktop, and double ovens. Relax in the sun-drenched living room or the vaulted 3-season porch overlooking established perennial gardens. The 1st floor primary suite features three closets and an updated marble ensuite. Two additional spacious main-floor bedrooms plus two massive 2nd-floor bedrooms, a family room, and office offer endless space. Unmatched privacy just minutes from amenities- a true must see!

72 Old Northfield Rd, Hinsdale

Listing courtesy of Jared R Rowland from Lamacchia Realty, Inc.. ()

$624,900

5 Beds ⋅ 4 Baths ⋅ 5099328 MLS

ADU with income potential! Nestled at the end of a quiet cul-de-sac in one of Keene’s most desirable neighborhoods, this charming 5-bedroom home offers an ideal blend of comfort, flexibility, and modern updates. A standout feature is the versatile ADU, offering excellent potential for additional rental income while also providing an ideal space for extended family, guests, an au pair suite, or a private home office. The ADU includes a private bedroom, full bath, laundry, kitchen, and living area, providing a comfortable and self-contained space. The main level features an open floor plan that seamlessly connects the updated kitchen, complete with granite countertops, to the dining and living rooms, creating an inviting space for everyday living and entertaining. The main floor also includes a convenient laundry room and powder room. Enjoy morning coffee or evening relaxation on the screened-in porch overlooking the backyard. Upstairs, you’ll find four well-appointed bedrooms and a full bath. A partially finished basement with a half bath provides additional space that can be tailored to your needs. The two-car garage offers ample storage and convenience. With its desirable location, modern updates, versatile ADU, and income-producing potential, this property offers a wonderful opportunity for a variety of living arrangements. Seller is a licensed NH Realtor.

35 Salisbury Rd, Keene

Listing courtesy of Zach Verow from Keller Williams Realty-Metropolitan. ()

$399,500

5 Beds ⋅ 3 Baths ⋅ 5098806 MLS

This is a charming must-see property set on a generous .71-acre lot in beautiful Swanzey NH. with the added benefit of an income producing in-law apartment! The main residence has 3 bedrooms and 2 baths along with a large living, dining area, wonderful full kitchen as well a 3-season porch and office/craft area. The attached in law suite has its own private paved driveway entry, light filled living area with French doors leading onto a trex patio deck, large kitchen, laundry area with sunroom, and 2 bedrooms on the 2nd level. (Tenant currently in place with a 12-month lease at $1,600 per month) Add in the expansive level front yard, versatile and expansive stand-alone workshop with electricity, pellet stove, and carport plus plenty of parking for all your friends and you have the total package!

112 S Winchester St, Swanzey

Listing courtesy of Joshua Benner from RE/MAX Town & Country. ()

$734,000

5 Beds ⋅ 4 Baths ⋅ 5098638 MLS

Nestled in highly desirable West Keene, this stunning 5 bedroom home offers the perfect blend of neighborhood charm and ultimate convenience. Minutes from local shopping, dining, top rated schools, the YMCA, and the Rail Trails, the location is unbeatable. Inside, the heart of the home features a large kitchen and an expansive dining room designed perfectly for hosting memorable family gatherings. This flows effortlessly into a welcoming living room anchored by a cozy fireplace, a dedicated home office, and a finished bonus basement room ideal for a gym or media space. Designed with ultimate flexibility and luxury in mind, the layout boasts dual primary suites providing exceptional privacy and comfort for multigenerational living, longterm guests, or a secondary main retreat. The true primary suite serves as your personal sanctuary, complete with an expansive walk in closet and a spa like bathroom featuring a jetted soaking tub. Modern comforts abound throughout, including a 2 car heated attached garage built to handle New Hampshire winters with ease. The backyard transforms into your own private oasis, anchored by an extraordinary, custom outdoor kitchen crafted for premier outdoor entertaining. Step outside to the beautifully designed patio and deck area where outdoor dining and entertaining take center stage. Spend hot summer days lounging by the above ground pool, prepare gourmet meals at your outdoor chef’s station, and host vibrant weekend barbecues under the stars. This West Keene gem delivers the lifestyle you have been looking for.

33 Queens Rd, Keene

Listing courtesy of Bob Barnard from Monadnock Realty Group LLC. ()

$549,900

5 Beds ⋅ 3 Baths ⋅ 5094732 MLS

This expansive Victorian on an oversized Lot has been lovingly restored, improved and maintained. Over $140,000. in recent upgrades. Convenient to Downtown Keene, hospitals and shopping, this amazing home blends classic elegance and workmanship with modern convenience. Vinyl Harvey windows throughout, updated kitchen with Granite and nearly new appliances, and a First Floor Primary added by the current owner, with French Door entrance at grade, and a new Primary bath combined with laundry room. The original First floor full bath has been fully remodeled, and all floors professionally refinished. A unique offering with two First Floor bedrooms. All the classic Victorian features remain, with a lovely fireplace and hearth and the stunning woodwork attendant to the homes of this era. Lovely stained glass greets you as you go upstairs to three additional bedrooms, full bath, and a generous family room. This home is truly perfect for multi-generational living. In just the last three years, a new Owens-Corning roof and ridge vent, structural repairs, both first floor baths remodeled, chimney repointed, aluminum wrap on exterior windows, new fencing for pets/kids in back yard, electrical upgrades and more. Please see attached list of upgrades. The basement is full and dry for tons of storage, and there is an unfinished walk-up attic for further storage or additional future finished space. Two lovely porches, on front and on the right side entry, and a private, fenced, paver patio on the left rear is perfect for outside meals and gatherings. Truly turn-key. All the heavy lifting has been done, and this home is ready for it's next chapter and family to enjoy.

67 Park Ave, Keene

Listing courtesy of Karl Zahn from Pat Clancey Realty. ()

$589,900

5 Beds ⋅ 3 Baths ⋅ 5087336 MLS

A Remarkable Property. A New Opportunity. Sellers Ready for Their Next Chapter. Nestled in the heart of New Hampshire’s beloved Monadnock Region, this remarkable circa 1830 Colonial blends rich history, timeless craftsmanship, and breathtaking natural beauty into one extraordinary offering. Set against the backdrop of iconic Mount Monadnock views and overlooking a tranquil mill pond and brook, the property captures the very essence of classic New England living. A rare treasure for antique home enthusiasts, the residence proudly features original murals attributed to renowned folk artist Rufus Porter, whose historic works are celebrated throughout New England. Inside, the expansive home offers five spacious bedrooms, oversized sun-filled rooms, and a warmth and character rarely found today. The renovated kitchen seamlessly blends period charm with modern convenience, complete with a functional antique cookstove and a cozy dining nook with serene water views. From the large screened porch, enjoy sweeping views of Mt. Monadnock while listening to the peaceful sounds of the brook below. The rear second-floor living area, featuring a sitting room, three bedrooms, full bath, and private staircase—offers outstanding flexibility for extended family, guest quarters, or potential Airbnb opportunities. Outside, a stately carriage house provides abundant space for vehicles, hobbies, equipment, or a home-based business, while the surrounding pasture and open fields create an idyllic setting for equestrian pursuits or simply enjoying the beauty of the countryside. Rich in history, impressive in scale, and set within one of New Hampshire’s most sought-after scenic regions, this is far more than a home—it is a rare opportunity to own a true piece of New England heritage. Come tour this remarkable home!

137 Prescott Rd, Jaffrey

Listing courtesy of Dean Deschenes from Arris Realty. ()

$564,800

5 Beds ⋅ 3 Baths ⋅ 5083431 MLS

Welcome to the prettiest house in Fitzwilliam! You deserve the best. Circa 1809, your 5-Bdrm, 3-Bath, Greek Revival home awaits you. Here, you’re uniquely positioned to entertain friends, be entertained, & take-in all the best that New England has to offer. Located right across from the Fitzwilliam Village Green, take-in small concerts & farmers markets. The Town Library is right next door, Townhall is 2 doors down. Fitzwilliam Common Historic District is a part of the National Register of Historic Places! Come be a part of its history. Enter through the white picket-fenced frontyard. You can’t help but to notice the grand fluted columns & large granite slab walkway here to greet you. Come onto the covered porch or head to the side yard where your pretty patio awaits. Interior antique features include your original wood-burning hearth in the livingroom, a gracious formal diningroom, wide-planked pumpkin pine flooring, & original antique mouldings.The Walk-Up 3rd Floor Attic was known as a bell-shaped ballroom in history! Most recently, the property had been lightly lived-in as a sole residence. Previously, she'd hosted small businesses including a Christmas shop and real estate business. More than charming, your spacious home has practical means, too. Well-maintained & updated utilities, the 1st floor’s layout can easily be adapted for multigenerational living. You have an excellent furnace with many heating zones plus alternative heat with a propane stove in the huge kitchen. Tremendous amount of storage with 2 attics, 2 basements, 2 livingrooms, as well as relatively short commuting distances - 20 mins to shopping & dining amenities in Keene & Rindge, 1/2 hr to Peterbough, and 1 hr 40 mins to Boston Proper. Truly, you have found a wonderful dot-on-the-map for adventure & gracious living. Have you been dreaming of a quintessential New England classic? You’ve found it in real life! More than just gorgeous scenery, go to lakes, mountains, & all New England offers!

9 Templeton Tpke, Fitzwilliam

Listing courtesy of Mary M. Belle Isle from EXP Realty. (Cell: 603-852-0333)

$789,000

5 Beds ⋅ 3 Baths ⋅ 5070076 MLS

The Hudson is a 5-bedroom 3-bathroom home with a stunning view of Grand Monadnock! The combination of farmhouse style and colonial architecture offers a timeless charm, and a floorplan that versatile enough to accommodate different lifestyles, from entertaining guests to working from home. The setting at the foot of Mount Monadnock and Stony Brook meandering through the development provide a truly unique lifestyle.

40 Roberts Dr Unit 3, Jaffrey

Listing courtesy of Denise Whitney from BHG Masiello Peterborough. ()

$789,000

5 Beds ⋅ 3 Baths ⋅ 5070073 MLS

40 Roberts Dr Unit 3, Jaffrey

Listing courtesy of Denise Whitney from BHG Masiello Peterborough. ()

$795,000

5 Beds ⋅ 4 Baths ⋅ 5069006 MLS

Elegant Colonial on Expansive Corner Lot in Charming Walpole Village. Step into timeless charm with this stately Colonial nestled on a large private corner lot in the heart of Walpole Village. Rich in character, this home showcases eight fireplaces and wide soft pine floors throughout. The first floor offers high ceilings and light-filled spacious rooms, including a bedroom with a walk-in closet and a ¾ bath—perfect for guests or convenient single-level living. Upstairs, you’ll find four additional bedrooms and flexible space ideal for an in-law suite, studio or home office. The impressive barn provides three bays for vehicles plus ample workshop or storage space. Outside, enjoy a private oasis featuring an in-ground pool with cabana, mature hemlock hedges, sunny garden areas, and access to a pond. Located just a five-minute walk from Walpole’s charming downtown shops, post office, library, restaurants, and churches—with easy access to I-91—this property is priced to sell and ready to be loved again.

26 Old N Main St, Walpole

Listing courtesy of Cynthia M Westover from Galloway Real Estate LLC. ()

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Cheshire County, NH 5 Bedroom Homes for Sale

Newest Cheshire County, NH 5 Bedroom Homes for Sale

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