Cheshire County Homes under $500,000

Welcome to Cheshire County, New Hampshire, a hidden gem nestled in the picturesque landscape of the Granite State. Known for its charming small towns, vibrant communities, and stunning natural beauty, Cheshire County offers a delightful blend of rural tranquility and modern convenience. With its rolling hills, lush forests, and sparkling lakes, outdoor enthusiasts will find endless opportunities for hiking, biking, and exploring the great outdoors.

Cheshire County is also rich in history and culture, featuring quaint downtowns filled with unique shops, local eateries, and art galleries that showcase the region’s creative spirit. The county is home to several notable towns, including Keene, the county seat, which boasts a lively arts scene and a robust calendar of community events.

For those looking to settle down in this idyllic region, Cheshire County offers an array of homes under $500,000, making it an attractive option for first-time buyers, families, and retirees alike. These homes range from charming historic properties to modern builds, each with its unique character and appeal. With a variety of options available, you can find the perfect abode that suits your lifestyle and budget.

Living in Cheshire County means enjoying the best of both worlds: a peaceful, community-oriented environment with easy access to urban amenities. Whether you’re drawn to the vibrant local culture or the stunning outdoor landscapes, Cheshire County is a wonderful place to call home. Explore your housing options today, and discover the perfect spot to create lasting memories in this enchanting corner of New Hampshire!

Newest Cheshire County Homes under $500,000

$339,900

4 Beds ⋅ 1 Baths ⋅ 5113382 MLS

This very sweet 4 bedroom Cape has been lovingly maintained by the current owner for 31 years. Nicely nestled into this wonderful family neighborhood, it is also in walking distance to downtown Keene, Keene State College, and Keene Ice Arena, as well as the extensive rail trail. Step inside the bright and spacious Great room, thoughtfully created by removing the wall between the Kitchen and the Living Room. This modern, open layout allows you to effortlessly prepare meals while staying connected to friends and family. Two bedrooms and full bath complete the first floor, creating the highly sought after option for convenient one floor living. Upstairs, you will find two additional generously sized bedrooms, providing ample space for children or guests. Extensive recent upgrades ensure convenience and peace of mind for years to come, including all new windows in 2006, new roof in 2021, new driveway, new water heater, updated electric and updated bathroom. The main staircase has been beautifully rebuilt to offer a more comfortable ascent, and now complements the home's gorgeous hardwood floors. Vinyl siding and sunny level yard make for an easy home to enjoy and maintain! Open Houses coming this weekend: Sat. Oct 10, 12:30-2, and Sunday Oct. 11, 10-11:30. Join us then, or schedule a tour today for your own private showing!

24 Colby St, Keene

$419,900

4 Beds ⋅ 2 Baths ⋅ 5113274 MLS

Nestled on a quiet residential street just a short walk from vibrant downtown Keene, this delightful 1920's home is sure to steal your heart! Lovingly maintained by the same owners for over 40 years, this property seamlessly blends timeless period craftsmanship with thoughtful modern upgrades. Step onto the welcoming, expansive covered front porch, and prepare to be charmed. Inside, you are greeted by a 27-foot Living Room accented by elegant wall sconces, a formal Dining Room featuring a built in china closet, and a charming eat-in Kitchen, equipped with a gas range. The practical main floor also boasts a large mudroom, accessible from the back deck, alongside a convenient half-bath with first floor laundry. Upstairs, the second floor offers 4 roomy bedrooms with a centrally located full bath as well as a wonderful 25-foot enclosed sleeping porch! The ultimate surprise awaits on the third floor. Here you will find two additional versatile rooms boasting high ceilings, large windows, abundant natural light, and generous closet space. These bonus rooms offer endless possibilities for home office, studio, or play area while framing beautiful views that extend to the scenic hills of Keene. The quality of construction shines through in the original wood floors, classic trim and stained glass transom windows. These historic features are perfectly complemented by practical modern upgrages, including high quality Marvin windows. Outside a detached one car garage provides great storage value, while the private yard offers a peaceful retreat. Situated in the sought after Fuller School district, this neighborhood is ideal for families of all ages. This beautiful home has been cherished for decades and is now ready to welcome its next chapter. Schedule your tour today to experience its warmth and character for yourself! Open House Sat. Oct. 10, 10am-12pm, and Sun. Oct. 11, 12-2pm.

55 Wilder St, Keene

$365,000

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

$259,000

3 Beds ⋅ 1 Baths ⋅ 5113121 MLS

This sweet home is located on a dead end, neighborhood rd, situated close to shopping and amenities. There are 3 bedrooms and 1 full bath, a large living room and the addition of a 23x10ft fully enclosed sun porch. The yard has a mix of open grass and shade. There's a metal roof and vinyl siding for easy upkeep. The 1 car garage opens up to the full basement, with laundry and updated systems. Don't wait! Make 25 Pierce Rd your new home.

25 Pierce Rd, Hinsdale

$319,000

2 Beds ⋅ 2 Baths ⋅ 5113066 MLS

OPEN HOUSE...SAT. OCTOBER 10, 2026 11 TO 1 PM. WHEN IS A CONDO A VERY SPECIAL HOME? Located a short walk to a pretty historic village, a river park, a sports complex and some local stores. Just a few minutes or two to Rte. 10 leading North to Keene, NH and heading South to Massachusetts. There are 3 units here at VILLAGE HILL CONDOS all sharing an OVERSIZED sunny level yard. So ideal for gardeners! Plenty of parking including 2 assigned spots. Let's step inside!! There is a spacious hallway entry area with a big closet and a half bath/laundry to the right. Then you will enter the comfortable living room leading to the easy to work in kitchen..Take your meals , coffee or drinks to the diningroom or the seasonal porch. The second floor has 2 large bedrooms. The master has a walk in closet with a desk . Keep those clothes and paperwork in this separate attached closet. The full bath is on this floor. Most condos don't have this full useable basement ideal for a workshop and for storing belongings. The Association fee is $350. a month and includes plowing, landscaping, exterior insurance, exterior building maintenance and more.** **

3 Swanzey St Unit 1, Swanzey

$139,900

2 Beds ⋅ 1 Baths ⋅ 5112987 MLS

GREAT OPPORTUNITY to buy into the housing market at an AFFORDABLE PRICE! Use your sweat equity to update this property to reflect you and your style. Owned for two generations within the same family, this modest two-bedroom home with one car garage is like a blank slate welcoming a makeover limited only by your imagination and yearning to be enjoyed like it has been over the past years. Located in a desirable W. Keene neighborhood, the lot is level and not too big to maintain with open space for gardening or relaxing. The location is within walking distance of parks, schools, the YMCA, and paths throughout the area. Just step out your door and access Cheshire Rail Trail’s extensive network of nearby biking and walking trails or ride into town to your favorite coffee shop. Conveniently located within 5-10 minutes of shopping, restaurants, the theater, medical facilities, the library and other Keene amenities, this property also has easy access to Routes 9, 10, and 12. Why rent? Have fun making this be your home worth coming home to and to love and enjoy for years to come! Showings begin Friday, October 9th by appointment only.

87 Pinehurst Ave, Keene

$352,500

3 Beds ⋅ 2 Baths ⋅ 5112957 MLS

Proudly call this this stylish 3 bedroom, 2 bath Townhome at Forest View Estates your new home. The moment you enter, the grand 2 story foyer invites you in to an open, spacious and homey main living area, perfect for hosting friends and family. The newly updated kitchen features black stainless appliances, tile back splash, granite island for seating & serving and a pantry which is also plumbed for a stackable washer/dryer if you like your laundry on the main level. Hardwood floors throughout. A first floor bedroom, or den/office if you prefer, plus a 3/4 bath with oversized shower and decorative tile create the opportunity and convenience of first floor living. An open staircase takes you to the second floor landing which leads to 2 nice sized bedrooms with great closet space and a second full bath. The french door off the kitchen brings you to a newly rebuilt deck overlooking a private wooded setting and lush green lawn. On the lower level you'll find a bonus room perfect for office, hobbies, crafts, working out or watching TV. Also direct entry to your oversized, heated garage. At just $305 per month, the HOA fee is one of the lowest in the area and surprisingly includes both water & sewer, plus plowing, landscaping and trash removal. Just minutes to shopping/dining in Keene, and very convenient to the Mass border.

28 Owens Dr Unit 40, Swanzey

$349,900

4 Beds ⋅ 2 Baths ⋅ 5112930 MLS

When you look for a good family home, I hope you're lucky enough to find one like this! Same owners for the past 35yrs, mountains of updates and improvements, and investment! From the plumbing, heating system, 200A electrical, hot water, appliances, siding and so much more! (see the disclosures) The icing on the cake is the 24x36' garage with two full stories! You'll walk into a large sunroom, then step into a big family kitchen, with doorways to the office and living room. A full ADA bath on the first floor has a large step in shower, whirlpool tub and laundry! Beautiful floors throughout, replacement windows and tall ceilings will make you feel right at home. The garage is absolutely amazing, has dedicated electrical service, GOBS of storage or hobby space! (Garage was $75k) This is an affordable family home in a quiet setting that you can move into with confidence and pride.

44 Gunn Mountain Rd, Winchester

$195,000

2 Beds ⋅ 1 Baths ⋅ 5112914 MLS

Investment Opportunity in Westmoreland, NH! Bring your vision and explore the potential this property has to offer. An opportunity for investors, contractors, or buyers looking for their next project. Whether you're considering a renovation, rental investment, or redevelopment potential, this property offers a chance to put your plans into action. Conveniently located in Westmoreland, with access to the surrounding communities of Keene, Brattleboro, and the Massachusetts border. Property is being sold AS IS. CASH or REHAB Loan ONLY. Rehab Needed, Buyers must conduct their own due diligence regarding the property's condition, permitted uses, and potential.

884 Nh Route 12, Westmoreland

$489,000

5112878 MLS

Great Investment Opportunity in Keene! This versatile property offers an excellent combination of rental income, storage, and future development potential, all situated on 1.3 acres of level, cleared land in a desirable Keene location. The property features a two-family residence with a spacious 4–5 bedroom home plus an additional 1-bedroom apartment, providing valuable rental income or flexible living arrangements. A large commercial-style garage offers plenty of room for storage, a workshop, vehicles, or other uses. Adding even more potential, there is the possibility of constructing an ADU or additional residence, creating an opportunity for a buyer to build their own home while using the existing two-family property as an income-producing asset to help offset the cost. Conveniently located within walking distance of the clinic and hospital, downtown Keene, shopping, restaurants, and a network of biking and hiking paths. A rare opportunity to own a property with income potential, substantial land, and exciting possibilities for future development. Bring your ideas and make the most of this exceptional Keene property!

470 Elm St, Keene

$365,000

4 Beds ⋅ 2 Baths ⋅ 5112873 MLS

This is a great 4-bedroom 2-bath house on a .20 acres corner lot. The yard is level and waiting for you to enjoy with the kids, dog and friends. And plenty of room for a firepit. New kitchen with brand new appliances and a counter with stools. The dining room opens to a spacious living room. Enter through the front door and pass through the enclosed porch and into the generous size foyer. Upstairs you will find 4 bedrooms with great closets, a completely renovated full bathroom and a walkup attic. One car detached garage with auto open. This home is within walking distance to downtown Keene, close to Carpenter Field, Robin Hood Park, tennis courts and Gathering Waters, a Waldorf school. Newer windows, 7-year-old roof, 9-year-old hot water heater. Great location with easy access to all the amenities and services you will need. This home is ready for its new owner and all the happy memories to be made.

259 Church St, Keene

$442,260

2 Beds ⋅ 2 Baths ⋅ 5112594 MLS

Ready and waiting to welcome you, this quality-built post-and-beam home offers warmth, character, and privacy on two acres near the end of a quiet cul-de-sac. Set on a knoll, the property enjoys seasonal views of Mount Monadnock and the Contoocook River. Step inside to a beamed cathedral ceiling, pine floors, and an inviting open-concept kitchen featuring a Jenn-air dual-fuel range. A stone-faced gas fireplace and westerly views create a comfortable setting for everyday living and entertaining. The first floor includes a bedroom with a three-quarter bath and direct access to the connecting deck. An open staircase showcasing classic post-and-beam details leads to the second-floor primary bedroom, complete with east-facing windows, a balcony with westerly views, and a full bath with a jetted tub. The basement offers a finished Coring-panel area ideal for hobbies or play, along with abundant storage. Tucked away on Fox Run Lane, this two-bedroom, two-bath home is close to all that Rindge has to offer, including commuter routes 202 and 119, shopping, schools, and the seasonal farmers market on West Rindge Common. Thoughtfully cared for since it was built, this distinctive home is ready for its next owner.

62 Fox Run Ln, Rindge

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