Cheshire Homes for Sale

Welcome to Cheshire County, New Hampshire – a hidden gem that beautifully marries the charm of rural living with modern conveniences. Nestled in the southwestern corner of the state, Cheshire County is renowned for its stunning landscapes, vibrant communities, and rich history. With the picturesque backdrop of the Monadnock Region, residents enjoy breathtaking views, abundant outdoor activities, and a serene lifestyle that feels worlds away from the hustle and bustle.

Cheshire County boasts a variety of quaint towns and villages, each with its own unique character. From the artistic allure of Keene to the tranquil beauty of Swanzey, there’s a perfect spot for everyone. The area is also home to excellent schools, local markets, and a thriving arts scene, making it an ideal place for families, retirees, and anyone seeking a welcoming community.

If you're in the market for a new home, Cheshire County offers an impressive selection of properties for sale. Whether you’re looking for a charming historic home, a modern family residence, or a cozy cottage nestled in the woods, you’ll find it here. Many homes feature expansive yards, scenic views, and proximity to outdoor recreational activities like hiking, skiing, and fishing.

With a warm community spirit and a rich tapestry of natural beauty, Cheshire County is more than just a place to live; it’s a place to thrive. Explore our listings today and discover your dream home in this enchanting corner of New Hampshire!

Newest Cheshire Homes for Sale

$99,000

4 Beds ⋅ 2 Baths ⋅ 5107063 MLS

Opportunity awaits on this .30 acre lot. Currently home to a double wide mobile home that has been completely gutted inside, this property is a blank canvas ready for extensive rehabilitation. Bring your vision and make it your own. A wide variety of possibilities exist here, making it a fantastic option for investors or anyone looking to take on a rewarding project. Location is everything, and this one delivers. Directly across the street, the Ashuelot River offers great kayaking right at your doorstep. The property also backs up to Pisgah State Park, home to thousands of miles of trails across both private and state managed lands, perfect for hiking, biking, and exploring right from your backyard. Outdoor recreation enthusiasts will also love the convenience of the OHRV staging area just down the street, offering easy access for off road adventures. property has a shared well with neighboring property. Seller has never occupied the property. Property is being sold AS IS. This property includes a camper and pickup truck, along with various items left on site, all to be conveyed with the sale at no additional cost. Buyer assumes full responsibility for removal and disposal of these items, which are included strictly on as is basis. no warranties expressed or implied. Buyers are responsible for conducting their own due diligence regarding zoning,shared well, and all other aspects of the property. Don't miss this chance to create something special in a location that offers unbeatable access to nature and recreation.

357 Ashuolet Main St, Winchester

$389,900

3 Beds ⋅ 3 Baths ⋅ 5107049 MLS

COME SEE this spacious “Second Empire” influenced 8 room home that has had many tasteful improvements and updates. Just a hop, skip and a jump from the Massachusetts line, it has a lovely village setting. Enter from the patio and proceed straight ahead to the gracious foyer. To the right is a large formal dining room with built-in shelves and a pellet stove that the owners use as their primary heat source, although they also have back-up electric heat. A non-working fireplace is in this room also. Do you work at home If so, you need an office or den of your own and this house has one. Had you gone to the left you’d be in the fully applianced, cabinet kitchen with breakfast bar. Just off the kitchen is a pantry, utility room, ½ bath and entrance to the 2 car garage. The comfortable living room is sufficiently large enough for all of your furniture. Step through the sliding glass doors and you’re on the rear patio. The private rear yard has a screened gazebo and plantings galore; peonies, hydrangeas, other perennials and a storage shed. Back in the house, where the majority of the floors are hardwood, a handsome staircase takes you to the second floor where you’ll find two closeted bedrooms, and a full family bath and a large, sunny primary bedroom with a second full bath. Tired of going up and down the stairs with the laundry? There’s a convenient laundry room to make life easier for you. The two car garage has plenty of storage room. Situated in a nice village setting it will be a great home for your family for years to come. Showings begin at our Open House on Sunday, August 30 from 11AM – 1PM. Look for signs on Route 119. Hope to see you there!

66 E Main St, Rindge

$335,000

2 Beds ⋅ 2 Baths ⋅ 5107013 MLS

This updated Sullivan ranch offers all the conveniences of a modern home in a cozy country setting. The propane stove and backup generator provide peace of mind during severe weather and the newer roof and furnace add to the feeling of comfort. Just minutes to Keene, this quiet country house has all the acreage you need to raise vegetables and chickens while having access to all that the Monadnock Region has to offer. Showings begin 4pm Friday 9/4. Open house Friday 9/4 4pm-6pm and Saturday 9/5 10am-12pm

48 Cross Rd, Sullivan

$372,500

1 Beds ⋅ 1 Baths ⋅ 5106995 MLS

Near the village of Fitzwilliam sits “The Little House”. Picture perfect with its wrap around porch and traditional beadboard ceiling, slate roof, and true divided-light, diamond-paned windows. In every room, its early 1900s Victorian charm shows through with original pine floors, push button light switches, and antique lighting, while an antique clawfoot tub sits perfectly at a window overlooking the gardens. The Rumford fireplace with oven (now home to a Harman pellet stove insert) and radiant floor heat throughout bring an exceptionally cozy warmth to New Hampshire winters. It has lived many lives: once a maple syrup house, some say the office for the local quarry, others a honeymoon cottage. The photos tell the rest - the romantic, storybook home the owners dreamed of. This carefully custom-updated gem is set on a picturesque 2+ acres. The property features attractive gardens, a Victorian inspired brick walkway, chicken coop, and original 36’ x 18’ post and beam 3-bay carriage house. The Monadnock Rail Trail is just a few steps away for both exercise and tranquil walks. A rare chance to own a piece of craftsmanship and imagination. The owner would like to hand the key to you and make “The Little House”, your home.

327 Richmond Rd, Fitzwilliam

$499,900

3 Beds ⋅ 3 Baths ⋅ 5106978 MLS

Beautifully maintained 3-bedroom, 2.5-bath Colonial situated on nearly an acre at the end of a quiet cul-de-sac in Jaffrey. Built in 2018 and still presenting in pristine, like-new condition, this home offers a wonderful combination of privacy, comfort, and convenience. The property abuts 2.38 acres of subdivision open space, providing an added sense of privacy and preserving the peaceful setting. The main level features a modern kitchen with a dedicated dining area, a welcoming family room with electric fireplace, formal living room, convenient first-floor laundry, and a comfortable layout ideal for both everyday living and entertaining. Upstairs, you'll find two additional bedrooms and a full bathroom, along with a spacious primary suite complete with walk-in closet and private en-suite bath. Recent improvements include newly installed mini-splits in the living room and primary bedroom, providing efficient cooling during the warmer months, as well as brand-new solar panels installed on the roof. A one-car garage offers added convenience during New Hampshire winters, while the basement provides a practical mudroom-style entry where coats, boots, and outdoor gear can be kept out of the main living spaces. Enjoy the tranquility of a quiet Jaffrey neighborhood while remaining close to local schools, grocery stores, restaurants, and downtown. Peterborough and Rindge are also just a short drive away for additional shopping, dining, and amenities. Outdoor enthusiasts will appreciate the home's proximity to Mount Monadnock and the area's many opportunities for hiking and recreation. A truly turnkey home in beautiful condition, offering modern updates, a peaceful setting, and an ideal location. Simply move in and enjoy! **OPEN HOUSES 8/29 & 8/30 from 11am-12:30pm**

39 Windy Fields Ln, Jaffrey

$399,900

3 Beds ⋅ 2 Baths ⋅ 5106932 MLS

Nestled in a picturesque setting at the base of Mount Monadnock, just moments from the Marlborough Trail, this charming 3-bedroom, 2-bath Cape offers the perfect blend of comfort, privacy, and outdoor adventure. Featuring a desirable first-floor bedroom and full bath, this home provides flexible living for every stage of life, while two additional spacious bedrooms and a full bath complete the second floor. The open kitchen and dining area is designed for gathering, showcasing beautiful granite countertops, quality cabinetry, and plenty of space for family and friends. Relax in the inviting three-season porch, the perfect spot for entertaining, enjoying your morning coffee, or simply taking in the peaceful sights and sounds of nature. The walk-out basement offers excellent potential to create additional finished living space, whether you envision a family room, home office, fitness area, or workshop. Outside, a thoughtfully treehouse adds a touch of magic and adventure, creating a special retreat for all ages. Enjoy the tranquility of the exceptional location while being just a short walk from the most climbed mountain in the United States. Whether you are hiking, exploring nature, or simply appreciating the peaceful surroundings, this property offers an unmatched lifestyle in one of the Monadnock Region's most scenic settings. A wonderful place to call home!

22 Shaker Farm S Rd, Marlborough

$389,900

3 Beds ⋅ 2 Baths ⋅ 5106922 MLS

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. 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 9th Rte, Chesterfield

$489,000

3 Beds ⋅ 3 Baths ⋅ 5106888 MLS

Tucked into a convenient Keene location just minutes from downtown shops, restaurants and everyday amenities, this charming home offers warmth, character, and a peaceful backyard setting. Set on .23 acres, the property features an incredible backyard with a covered patio including outdoor kitchen, TV, Hot Tub and gas fire pit-perfect for relaxing and entertaining. Inside, the home welcomes you with beautiful wood floors that run throughout much of the main level. A cozy eat-in kitchen offers a comfortable space for everyday meals and opens directly to the dining room which also opens up to your back porch and patio, creating an easy and natural flow for gatherings. Just beyond, the dining is the spacious living room giving the main living space an airy and inviting feel filled with natural light. Three bedrooms are located on the 2nd floor with a 3/4 bathroom conveniently located between them. The primary bedroom suite has its own 1/2 bathroom with washer and dryer. The home also includes a full unfinished concrete basement offering excellent storage or workshop potential, and second washer dryer hook ups. An oversized, two car, heated garage adds convenience and additional space. Public water and sewer, along with baseboard oil heat, and a pellet stove make for simple and efficient living. With its flexible living space, private backyard bursting with amenities and convenient location close to downtown Keene this property offers a wonderful opportunity to make a home your own.

32 Matthews Rd, Keene

$375,000

3 Beds ⋅ 2 Baths ⋅ 5106765 MLS

*OPEN HOUSE SAT 8/29 from 11am-1 + SUN 8/30 from 1-2:30pm * Extensively refreshed and ready for its next owner, 7 Danforth Road is a 3-bedroom, 2-bath ranch set on 1.5 acres in a quiet country setting. Almost every part of this home and property has been touched in recent weeks by the homeowner, to make it perfect for its next caretaker! Everything you look at inside has had some kind of cleaning, repairing, painting or general sprucing up done to it. Numerous recent updates include brand new flooring (lifetime warranty!) and lighting throughout, a complete kitchen refresh, pellet stove and new laundry. This home offers easy one-level living with a primary bedroom and bath, along with two additional bedrooms, a second full bath, kitchen, dining area and living room with the new pellet stove. Nothing needed here except to move your furniture in and make it yours! The walkout lower level provides a large amount of additional space for storage, hobbies, a workshop or future finished living area. Two former basement bedroom spaces remain framed and offer you the chance to make them into whatever you need. The basement also includes a workbench, newer hybrid water heater, a dehumidifier, and a 50-amp generator hookup. Outside, the property has a paved driveway, detached carport for vehicle or equipment storage, a separate shed, fully-fenced backyard and a spacious rear deck. Lots of sunshine everywhere, and an abundance of room for gardening, pet areas or other outdoor activities. Located in Rindge, you'll be close to the area's lakes, ponds, conservation trails and recreation, with Mount Monadnock local and Lake Monomonac only a mile away. Just 2 minutes to the MA border, 5 minutes to shopping and groceries, and 25 minutes to Peterborough, this house sits in a lovely and convenient location. A well-rounded property with a long list of recent improvements make this a "must see" home, so we look forward to having you over soon!

7 Danforth Rd, Rindge

$199,900

2 Beds ⋅ 1 Baths ⋅ 5106731 MLS

Welcome to 22 Wetmore Street, a charming and efficient 2-bedroom, 1-bath home tucked away on a quiet dead-end street in Keene. Offering 616 square feet of comfortable living space, this open-concept home makes the most of every inch, with a practical layout that feels bright, welcoming, and easy to maintain. Recent updates include a new roof, new furnace, and new hot water heater, providing peace of mind for the next owner. Vinyl windows add to the home's efficiency and low-maintenance appeal. Outside, enjoy a level .25-acre lot with plenty of room for gardening, relaxing, or entertaining. A garden shed provides convenient storage for tools and outdoor equipment. The location offers the best of both worlds, peaceful neighborhood surroundings while being close to shopping, dining, schools, recreation, and other everyday amenities. Whether you're looking for a comfortable first home, a downsizing opportunity, or an investment property, 22 Wetmore Street offers affordability, convenience, and easy living in a desirable Keene location.

22 Wetmore St, Keene

$835,000

3 Beds ⋅ 2 Baths ⋅ 5106672 MLS

This one-of-a-kind private waterfront log cabin retreat offers an exceptional waterfront lifestyle. This 1.1 acre lot nestled in a cove is shielded from main part of boat traffic and offers peaceful enjoyment as well as stunning views. Water frontage is 305' with multiple sections of floating boat docks making this an ideal spot for water enthusiasts.***** Step inside this open concept post and beam log home where warmth & character shine throughout. The spacious kitchen flows seamlessly into the living and dining areas, creating an inviting space for entertaining. A cozy wood stove anchors the room, while wide pine finishes & windows throughout showcase breathtaking lake views. ******* Upstairs is the primary bedroom with a private bath, plus a 2nd room & laundry area in a loft-style layout. ****** Main level has 2 additional bedrooms providing flexibility for guests, family or a home office. Also on the main level is a full bathroom. One of many standout features is the enclosed 8x22 porch perfect for relaxing and enjoying lake views.********* In addition to the porch, there's a 2 car garage with a huge bonus room area above, perfect for a fun family hangout, game room or guest area. Even better, this home has been thoughtfully updated with all major systems recently replaced, including a brand-new hot water tank, electrical panel, furnace, water softener system, and sump pump-providing peace of mind for years to come. Come check out this beautiful slice of heaven and make it your forever home or a peaceful vacation retreat. Showing appointments start at 12 noon on 8/28/26. Seller will review any offers on 08/31 by 5 pm.

232 Tigola Trl, Stoddard

$430,000

3 Beds ⋅ 1 Baths ⋅ 5106633 MLS

Welcome to the newest listing in Rindge, at 71 Butterfield Road! This beautiful, turn key, move in ready home is awaiting its new family and is sure to not be on the market long! Located near the end of a dead end road on 3.2 acres, sits this cozy 3 bedroom, 1 bath, 1,072 sqft ranch home that is full of windows and plenty of natural light! Walking up the stairs onto the porch, you enter the kitchen and dining area. The kitchen has been tastefully upgraded, and includes beautiful stainless steel appliances, that are sure to cook up many tasty meals for years to come! The centrally located living room is ready for movie nights or just relaxing after a long day at work. A second entryway with mudroom space is located off of the living room. On the other side of the living room is the first bedroom as well as the homes full bath. Down the hallway you will find the second bedroom as well as the primary bedroom. Downstairs you will find an additional 390 sqft of finished space. A large flex room perfect for a lower level movie room, a family game room or work out room awaits on one side of the stairs and on the other is the downstairs laundry room. Located next to the laundry room is a large closet that houses a newer whole-house water filtration system that will help ensure great drinking water! Through the door in the laundry room you enter a very oversized 1 car under-house garage (maybe 2 cars inline?) Outside you will find a small shed, as well as a large detached garage good for parking another vehicle, atv, or lawn equipment. Open Houses this weekend Saturday 8/29 from 10-12Pm and Sunday 8/30 from 11-1Pm Private showings begin after the open house on Saturday.

71 Butterfield Rd, Rindge

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