Cheshire County, NH Real Estate Search

Cheshire County, NH 5 Bedroom Homes for Sale

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Newest Cheshire County, NH 5 Bedroom Homes for Sale

$439,000
5 Beds 2 Baths 5101693 MLS
There’s more than meets the eye at this spacious Greenwood Avenue home! Nestled in Keene’s established and highly desirable Edgewood neighborhood, this inviting 5 bedroom, 2 bath home offers the perfect blend of classic character, modern updates, and exceptional versatility. Enjoy this beautifully renovated kitchen, featuring elegant quartz countertops, abundant cabinetry, and plenty of workspace for everyday living and entertaining. Just beyond, the bright four-season sunroom expands your living space with both heat and air conditioning, making it the perfect place to relax, work, or gather year round. Timeless architectural details add warmth and charm throughout, including graceful arched doorways, built-in shelving, and a fireplace that is being enhanced with new flue liners and a wood-burning insert. Hardwood floors run through most of the home, with professional refinishing already scheduled to begin in August, giving the next owner beautifully refreshed living spaces. In addition, the home's major systems are receiving their annual maintenance, providing added peace of mind. With five generously sized bedrooms, including two conveniently located on the first floor, this home easily adapts to your lifestyle, whether you need space for multigenerational living, a home office, guests, or creative hobbies. Additional highlights include central air conditioning, an attached garage, a fully fenced backyard, and the added security of a portable generator. Ideally located just minutes from downtown Keene, you'll enjoy easy access to shopping, restaurants, parks, walking trails, and recreation. If you've been looking for a home with generous space, thoughtful updates, enduring character, and the opportunity to make it your own, this Greenwood Avenue gem is one you won't want to miss.

25 Greenwood Ave, Keene

Listing courtesy of Gina Paight from Greenwald Realty Group. ()

$3,250,000
5 Beds 2 Baths 5100007 MLS
"Wildair". Built in 1928, the era of families gathering at expansive summer residences to enjoy each other's company and to commune with nature, this quintessential shingled seasonal residence of 5 bedrooms with boathouse has been cherished by members of the same family for nearly 100 years. It features over 687 feet of frontage on deep water, 781 acre Nubanusit Lake, the premiere lake in Southern New Hampshire. Much of its shoreland is protected by conservation easements or ownership, as is this property's 25.1 acres. The last house on a privacy ensuring, 3/4 mile long, seasonal driveway shared by 5 owners. the property is an oasis of peace. Live outside on the 12' x 47' + 12' x 18' wraparound screened porch. Gather the family in the 29' living room in front of the massive wood burning hearth (the chimney was serviced this spring) for game night and story telling. Around the corner is an office for staying connected -- the property has high speed internet! There's room for everyone around the dining room table in front of a second fireplace and viewing the lake through the screened porch. A butler's pantry with sink and dishwasher connects to the kitchen. In place but no longer used are the Glenwood woodcookstove and the old wooden front ice boxes. The soapstone sink, wood countertops and built in hutch are in use. Off the back hall is a utility room, shower bath, and sleeping porch. Upstairs are two primary bedrooms, three twin bedded rooms and a hall bath. Each bedroom has its own sink! Electrical service, plumbing and the septic system were updated 25-30 years ago. Water is from the lake. The boathouse at the water's edge has a rec room or overflow sleeping space on the second floor. Storage for boats and outdoor accessories are on the ground floor, which opens to a huge top deck surrounded by a lower deck for swimming and boat launching. Outbuildings include a woodshed and a former ice house, now used for storage. Be Wildair's next stewards.

96 Miller Dr, Nelson

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

$799,000
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 large, 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. The bedroom configurations provide exceptional privacy and comfort: two bedrooms feature private en-suite bathrooms, including a luxurious primary suite complete with an expansive walk-in closet and a spa-like bathroom featuring a jetted soaking tub. Modern comforts abound, including a 2-car heated attached garage to handle New Hampshire winters with ease. The backyard is an absolute private oasis designed for premier outdoor entertaining. Step outside to a beautifully crafted patio and deck area that centers around a fully equipped outdoor kitchen. Spend hot summer days lounging by the pristine above-ground pool, or host vibrant weekend barbecues under the stars. Whether you are gathering around the dining table, relaxing by the fire, or hosting a crowd outdoors, this West Keene gem delivers the lifestyle you have been looking for. Open House Saturday 7/11/26 10am to Noon.

33 Queens Rd, Keene

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

$895,000
5 Beds 5 Baths 5098271 MLS
Welcome to 29 Rand Road! A truly breathtaking property set on 3.09 private acres, offering the perfect blend of peace, privacy, and convenience. Proudly owned by the original owners since it was built, this meticulously maintained home is truly one of a kind. Enjoy the tranquility of country living while remaining just minutes from shopping, major highways, dining, and other everyday amenities. The spacious main home offers 4 bedrooms, 4 bathrooms, and an abundance of living space throughout. The updated kitchen features newer stainless steel appliances, ample cabinet space, and an abundance of natural light, making it the perfect place to cook and gather. Beautiful natural woodwork flows throughout the home, adding warmth and timeless character. The main level also offers a sun filled living room space, dining area that's open to the kitchen, a half bathroom, and a laundry area. Step up to the 2nd floor and you will find your very own. sun-filled primary suite offers direct access to a private walkout deck, creating the perfect retreat. The 2nd floor offer 3 additional, generously sized bedrooms, and an additional full bathroom for convenience. The walk-up attic is completely finished offing the perfect space to make a play room, library, office, etc. The finished basement provides additional living space and even includes a relaxing sauna. Adding even more versatility to the property is a detached 612 sqft ADU complete with its own kitchen, full bathroom, and bedroom, deal for extended family, guests, a home office, or potential rental income. A detached shed provides storage for tools and outdoor essentials. With its exceptional living space, unique features, and picturesque setting, 29 Land Road is a rare opportunity to own a property that offers both comfort and flexibility! Please see floor plans and subdivision plans attached to MLS listing.Showings will start at the open house on Saturday 7/11 from 12-2pm.

29 Rand Rd, Rindge

Listing courtesy of Salah Amrani from EXP Realty. (Cell: 978-457-3571)

$849,000
5 Beds 3 Baths 5097961 MLS
Set on nearly 8 private acres in Rindge, just minutes from the Massachusetts border for an easy commute, this charming country property offers the perfect blend of privacy, space, and comfort. Set back from the road on a paved driveway, the home is surrounded by a beautiful mix of wooded landscape, perennial gardens, and open lawn. The large fenced backyard features a picturesque gazebo, mature plantings, and plenty of room to relax or entertain. Inside, you'll find 4,284 square feet of living space with five bedrooms and three bathrooms, offering a flexible layout for everyday living and gatherings alike. The spacious kitchen flows into the dining area and sunroom, creating the heart of the home. Enjoy abundant counter and cabinet space, a double oven, and peaceful backyard views. A first-floor laundry room is conveniently located near a full bath and a well-maintained sauna. The first-floor primary suite provides the ease of single-level living and features hardwood floors, a dressing area, and a recently remodeled private bath. Upstairs, skylights fill the home office and bonus room with natural light, while generous closet space and a full bath with double vanities comfortably accommodate family and guests. An unfinished basement offers endless potential for future living space, a workshop, or additional storage. A durable metal roof with a lifetime warranty, automatic whole-house generator, and attached three-car heated and cooled garage with a utility sink add lasting value and peace of mind. Conveniently located near shopping, dining, and everyday amenities, the home is approximately 1 hour 15 minutes from Manchester-Boston Regional Airport and about 1½ hours from Logan International Airport. Whether you're looking for room to grow, space to entertain, or a peaceful country retreat, this exceptional Rindge property is ready to welcome you home.

185 Thomas Rd, Rindge

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

$599,900
5 Beds 3 Baths 5094732 MLS
This expansive Victorian on an oversized Lot has been lovingly restored, improved and maintained. 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. ()

$1,399,950
5 Beds 4 Baths 5089798 MLS
BREATHTAKING VIEWS, STUNNING SUNSETS, ACREAGE, & PRIVACY! Purposely sited to take advantage of long-range mountain views, this METICULOUSLY maintained property is the epitome of the QUALITY OF LIFE New Hampshire is known for. A winding driveway will lead you with anticipation into this very special Country Estate nestled on 30 acres of open and forested land w/stone walls. Once you arrive, it feels like you are on top of the world, away from it all in your own private sanctuary! A covered porch will greet you with a welcoming entry to step inside, and then the experience begins… Attention to detail and quality of construction are evident throughout this custom-built open concept 5,600 sq. ft home. There are dramatic angles, lots of windows, and beautiful wood & tile flrs. A spacious Gourmet kitchen w/granite countertops, double ovens, large center island w/breakfast bar, and wet bar opens to adjoining living areas conducive for entertaining family & friends. At the end of the day, step outside onto the expansive deck to watch the SPECTACULAR colors as the sun sets followed by stars in the quietness of the night. Other features include a 1st flr primary bdr suite w/walk-in closet, jetted tub, & tiled shower w/jets, a home office w/French drs & fireplace, a spacious family rm w/custom stonework, beamed ceilings, and views, plus a mudrm & laundry. There are 2 bdrms and a full bath on the 2nd flr w/balcony overlooking a 2-story wall w/windows that radiate natural light throughout. The walkout lower level offers more finished living area - 2 bdrms, a bath, a recreation rm w/stone fireplace, private gym area, and a sitting rm w/views. The floor plan is versatile and lends itself to multi-generational living, w/Central Air, Stand-Alone Generator, & High-Speed Internet. For the outdoor enthusiast, hike, bike, ski and enjoy your natural surroundings and all that the activities the Monadnock area and NH offer. Approx.15 min to Central Keene. Showings by appt.

72 Corey Mine Rd, Sullivan

Listing courtesy of Deborah L Lucey from RE/MAX Town & Country. ()

$599,900
5 Beds 3 Baths 5087336 MLS
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! Motivated Sellers

137 Prescott Rd, Jaffrey

Listing courtesy of Dean Deschenes from Arris Realty. ()

$499,999
5 Beds 3 Baths 5086353 MLS
Welcome to this spacious five-bedroom, three-bath New England home, where timeless charm meets endless potential. Set on a picturesque lot surrounded by rolling hills and tranquil countryside, this inviting property offers the perfect balance of privacy, space, and opportunity. Designed with versatility in mind, the property features a barn and a detached two-car garage with radiant heat—ideal for year-round projects, hobbies, storage, or a workshop. Above the garage, unfinished space provides a blank canvas for your vision, whether you're imagining a guest suite, home office, studio, or additional living quarters. Inside, expansive living spaces are filled with natural light and highlighted by beautiful floors milled directly from the property, creating warmth, character, and a unique connection to the land. With generous room throughout and the opportunity to make it your own, this home is ready for its next chapter while retaining the authentic charm that makes it so special. Conveniently located near Keene, Brattleboro, the Massachusetts border, and just minutes from Pisgah State Park, you'll enjoy easy access to shopping, dining, hiking, and year-round outdoor recreation, all while savoring the peace and beauty of country living. Whether you're seeking a primary residence, a place to pursue your passions, or simply more room to spread out, this exceptional property offers endless possibilities. Schedule your private showing today and discover everything this special home has to offer.

231 Chesterfield Rd, Hinsdale

Listing courtesy of Megan Manley from North New England Real Estate Group. (Cell: 603-903-3907)

$1,550,000
5 Beds 5 Baths 5086270 MLS
Set atop a majestic, private setting with sweeping views—including a stunning balcony vista of Mt. Monadnock—this exceptional 5-bedroom home in Swanzey offers the perfect blend of elegance, comfort, and quality craftsmanship. Designed for both everyday living and entertaining, the home features multiple inviting gathering spaces, from the sun-drenched sunroom to the beautifully appointed living and family rooms. A gracious morning staircase adds charm and functionality, while the first-floor office with custom built-ins provides an ideal work-from-home retreat. The expansive kitchen impresses with generous workspace, abundant cabinetry, and seamless flow into the surrounding living areas. Thoughtful architectural details, warm wood finishes, and high-end construction are evident throughout.  Large island, wine fridge.  Enjoy extensive hardscaping, including a spacious patio perfect for outdoor dining, relaxing, and taking in the serene landscape. Gazebo with hot tub, multiple outbuildings for projects and landscaping storage.  The property continues to impress with an additional detached 3-bay garage and beautifully maintained grounds that enhance the home’s sense of privacy and scale. A rare offering combining refined living, breathtaking views, and timeless quality—this is New Hampshire living at its finest.  Additional 7.5 acre building lot abutting included for $1,650,000.

101 Highland Cir, Swanzey

Listing courtesy of Joshua Greenwald from Greenwald Realty Group. ()

$599,900
5 Beds 4 Baths 5084061 MLS
Discover the perfect blend of New England charm, modern comfort, and scenic beauty in this inviting 5 bedrooms, 3.5 baths home with over 2,600 square feet of finished living space in one of Swanzey’s most picturesque settings. From the moment you step inside, you’ll appreciate the warmth and character of the beautiful hickory hardwood floors, harvested directly from the property, creating a one of a kind connection between the home and its natural surroundings. Fresh paint throughout gives the interior a bright, refreshed feel, making this home truly move in ready. Designed for both everyday living and entertaining, the main level offers generous living space filled with charm and functionality. Upstairs, the spacious primary suite provides a relaxing retreat with its own private bath and walk in closet, while three additional bedrooms offer plenty of flexibility for family, guests, or home office needs. The finished basement is in-law suite ready as this space adds exceptional versatility, featuring a a bedroom, private living area, walk in closet, and a spa inspired bathroom, easily converted to a full in law with the addition of a kitchenette, ideal for multigenerational living, guest accommodations, or expanded living space. What truly sets this property apart is the breathtaking setting. Enjoy picturesque views of the covered bridge, peaceful river scenery, and direct access to the rail trail spanning from Keene to Hinsdale, right from your doorstep. Whether you enjoy morning walks, biking, or simply taking in the beauty of nature, this location offers a lifestyle that is hard to match. With a two stall garage, spacious layout, and a setting that perfectly balances recreation, and timeless charm, this is more than just a home; it’s a place to create lasting memories. Rarely does a property offer this much character, versatility, and natural beauty in one exceptional package. Come take a look at the Open House June 20th 11 am - 1 pm

8 Matthews Rd, Swanzey

Listing courtesy of Aimpoint Realty Group from Keller Williams Realty-Metropolitan. ()

$599,900
5 Beds 3 Baths 5083431 MLS
4 to 5-Bdrm, 3-Bath, Grand Greek Revival home Circa 1809 uniquely positioned to entertain and be entertained. On the village square, take-in village concerts, the sociable library nextdoor, & farmers markets. Your white picket-fenced frontyard offers a covered porch, flanked with fluted columns, pretty patio awaits on the side yard, & your fielded backyard slopes gently. The 3rd floor bell-shaped ballroom’s often noted in Fitzwilliam history. Offers 2 attics of storage space along with the newer dry basement space. Spacious home has updated utilities, potential for 1st-floor living, a tremendous amount of storage, and a kitchen propane fireplace on stonehearth. Antique features include your original wood-burning hearth in the livingroom, a gracious formal diningroom, wide-planked pumpkin pine flooring, large granite slab walkway, & original antique mouldings. While the property has been a lightly lived-in sole residence for nearly the past twenty years, it has also hosted small businesses including an antique Christmas shop and real estate office. Truly, you have found a wonderful dot-on-the-map for adventure and gracious relaxation, and an undoubtedly delightful classic New England home to call your own. More than just gorgeous scenery, you're just 20 mins to amenities in Keene & Rindge, 1/2 hour from Peterbough, & 1 hr & 40 mins to Boston Proper. That’s some view just outside your door! Did you know that Fitzwilliam Common Historic District is a part of the National Register of Historic Places? Come be a part of its history.

9 Templeton Tpke, Fitzwilliam

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

$357,000
5 Beds 2 Baths 5082393 MLS
New beginnings start here. This classic 1880 New Englander sits prominently on Main Street in Marlborough, blending timeless charm with thoughtful system updates. Rich in character, the home showcases hardwood floors and original details throughout, including a striking tin ceiling in the kitchen. A spacious mudroom entry leads into the updated kitchen, complete with granite countertops, updated appliances, and an oversized pantry designed for everyday functionality. Just off the kitchen, a screened porch overlooks a private courtyard, offering the perfect setting for outdoor dining, gardening, and relaxing to the peaceful sounds of the nearby babbling brook. The flexible floor plan includes a first-floor bedroom and three-quarter bath, ideal for multigenerational living or guests. The light-filled dining room provides an inviting space for gathering, while the second floor offers multiple living areas to suit a variety of lifestyle needs. A true standout, the attached three-story barn opens the door to endless possibilities, whether for storage, workshop space, or an in-home business. Recent improvements include a newer roof, oil tank, hot water heater, and new HVAC 4 Zone heat pump offering, offering added efficiency and peace of mind. A property filled with character, versatility, and opportunity. Come experience all that this special home has to offer. Village setting, 10 minute commute to Keene and 20 minutes to Peterborough. Seller offering a $15,000 concession towards exterior painting.

291 Main St, Marlborough

Listing courtesy of Hvizda Realty Group from EXP Realty. (Cell: 603-557-6661)

$476,500
5 Beds 4 Baths 5078492 MLS
Welcome to your spacious sanctuary in the heart of Alstead! Conveniently located near the town center, this expansive home offers room for everyone and is move-in ready with a new septic installed in 2020. Sellers are motivated & ready for a quick closing. Set on a sunny lot, this beautifully maintained home features 5 bedrooms, multiple gathering spaces, and a finished walkout basement offering endless possibilities - guest space, recreation room, home office, or media area. The open-concept kitchen and dining room make entertaining easy. Relax in the cozy living room, or sip morning coffee on the covered front porch. The breezeway entry from the attached 2-car garage doubles as a mudroom space. Upstairs, you'll find generously sized bedrooms and a convenient laundry area and full bath. The standout is the primary bedroom suite—your private retreat—featuring a walk-in closet, private bathroom, and a balcony overlooking the backyard, perfect for peaceful mornings or stargazing at night. The finished lower level offers a large bonus room, walkout access to the backyard, an additional bedroom, and a half bath—ideal for guests or multi-generational living. Outside, enjoy summer afternoons in the pool, evenings on the back deck, and plenty of space for gardens or outdoor play. With newer upgrades, central air, high-speed internet availability, & a location close to Lake Warren, hiking, skiing, and snowmobile trails, this home is both a peaceful escape & aa practical everyday haven. This is a short sale, subject to third-party approval, being sold “As-Is”. Short Sale Advisors LLC, a licensed New Hampshire Debt Adjuster, has been retained by the Seller to facilitate short sale and loss mitigation negotiations with lienholders.

16 Vilas Rd, Alstead

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

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