Cheshire County Homes under $750,000

Welcome to Cheshire County, New Hampshire, a hidden gem nestled in the picturesque landscapes of the Granite State. Known for its charming small towns, rich history, and stunning natural beauty, Cheshire County offers an idyllic lifestyle for families, retirees, and outdoor enthusiasts alike. With the majestic Monadnock Mountain as a backdrop, residents enjoy an abundance of recreational activities, from hiking and biking to fishing and skiing in the winter months.

Cheshire County is not just about breathtaking vistas; it boasts vibrant communities such as Keene, Swanzey, and Winchester, each with its unique character and charm. Here, you’ll find a mix of quaint shops, local eateries, and cultural attractions that foster a strong sense of community. The county is also home to several parks and nature reserves, perfect for leisurely strolls or family picnics.

If you’re looking to make Cheshire County your home, you’ll be pleased to know that there are fantastic real estate options available under $750,000. Whether you’re searching for a cozy single-family home, a spacious colonial, or a charming cottage, this budget opens the door to a variety of properties that cater to diverse lifestyles. Many homes in this price range feature modern amenities, beautiful gardens, and easy access to local schools and services.

Embrace the tranquility and charm of Cheshire County, where your dream home awaits. With affordable housing options and a warm community spirit, it’s the perfect place to put down roots and create lasting memories. Come explore all that this enchanting region has to offer!

Newest Cheshire County Homes under $750,000

$300,000

2 Beds ⋅ 1 Baths ⋅ 5113565 MLS

Property sits up on a rise with an open view below. Quiet culde sac within a nice established neighborhood. The home has a family room entrance adjacent to the garage and steps into the kitchen. Double french doors open to a formal dining room, which has also been used as a bedroom. There are numerous double closets and plenty of storage space. The kitchen has attractive cabnetry, a pantry, and tile backslash. The basement has been used for entertaining and has a separate alcove used for addition sleeping. One third of the basement is a utility room with a slop sink and close dryer.

31 Pierce Rd, Hinsdale

$524,900

3 Beds ⋅ 3 Baths ⋅ 5113564 MLS

Tucked away in the Hidden Lake Association on a private 1.70 acre lot, you will find this spacious& inviting home that has been lovingly owned and cared for by the same owners for the past 18 years! During their ownership, the home has undergone numerous renovations and updates, thoughtfully improving the home over the years. One of the most notable transformations was the conversion of the original garage into a spacious first-floor primary bedroom with its own 3/4 bath! This property has deeded access to Highland Lake which is 7 miles long encompassing +/-700 acres and is well known for its healthy population of Largemouth Bass! Bring your motorboats, jet skis, kayaks, canoes, & fishing poles - this water setting is perfect for enjoying all that lake life has to offer! The annual association fee of $850 includes not only lake access, but year-round road maintenance, a private boat launch, inground swimming pool, clubhouse, playground, & a tennis/basketball court. Step inside and you will appreciate the open concept floorplan &spacious layout designed for comfortable everyday living. On the first floor you will find the large primary bedroom with 3/4 bath, den, and a laundry room complete with a new washer & dryer. The dining area features vaulted ceilings & a slider leading directly to the fenced in backyard featuring a beautiful patio that was installed in 2021 & a firepit for those cold autumn nights. Storage is plentiful with two large sheds, providing plenty of room for toys & lawn equipment. A standby generator installed in 2022 provides added peace of mind. Head upstairs where you will find an expansive bedroom, full bath, sitting area,& two additional bedrooms, offering plenty of space for guests. This property is located minutes away from the association amenities and Hidden Pond as well! Conveniently located about 30 mins to Keene & Peterborough, & less than 2 hrs from Boston. Schedule your private showing today & meet your forever home!

195 S Hidden Lake Rd, Stoddard

$599,900

2 Beds ⋅ 3 Baths ⋅ 5113502 MLS

Built in 2021 this well-maintained 2-bedroom, 2-bath home set on 2.3 private acres with access to Highland Lake. The main home features an open-concept layout with good natural light and a comfortable year-round living design. A fully self-contained 1-bedroom, 1-bath ADU also offers an open-concept living area and includes its own garage, separate from the main house, providing added privacy and flexibility for guests, extended family, or rental income. The acreage offers a quiet country setting with room to enjoy the outdoors, while Highland Lake access provides opportunities for swimming, boating, and recreation. A versatile property with valuable additional living space in a peaceful Stoddard location.

67 Champney Rd, Stoddard

$375,000

5113478 MLS

A unique opportunity to own a well-maintained and thoughtfully updated 2-unit property on a quiet dead-end street in a convenient Keene location. Set among just a handful of homes, this property offers a welcoming residential setting while remaining just a short distance from downtown shops, dining, and local amenities. The first-floor two-bedroom unit features its own dedicated washer and dryer along with efficient oil heat that has been recently serviced. Upstairs, the spacious three-plus-bedroom unit offers propane heat, a newly installed dishwasher, and brand-new dedicated laundry. Mature trees provide a natural buffer along the side of the property, while established perennial plantings add seasonal color around the front and sides of the home. The backyard provides open space with room for gardening or creating an inviting outdoor area. A generous driveway accommodates up to four vehicles, and each unit has its own laundry for added convenience. Tenants pay their primary utilities, with the landlord currently responsible for water, sewer, and snowplowing. There is also a large storage space onsite that is currently shared. Whether you're looking for an investment property or an owner-occupied duplex with additional rental income, this well-positioned property offers flexibility, thoughtful updates, and the comfort of a residential setting close to all that downtown Keene has to offer. Showings available on Wednesdays and Saturdays by appointment.

8 Mystic Pl, Keene

$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

$524,900

3 Beds ⋅ 2 Baths ⋅ 5113333 MLS

Welcome to this contemporary 3-bedroom, 2-bath home featuring a one bay attached garage and a great West Keene location near the rail trail, Wheelock Park, golf courses, and schools. The spacious first floor layout features vaulted ceilings, a comfortable living room, and an added family room with a Harman pellet stove, creating a warm and inviting space for relaxing or entertaining. The galley-style kitchen offers an efficient layout, while a first-floor bedroom and full bath provide flexible living options. Upstairs, the primary bedroom features a walk-in closet, along with an additional bedroom and full bath. The basement provides plenty of bonus space for a home gym, hobbies, storage and laundry. Recent updates include a 2-year-old boiler, oil tank and a new washer & dryer. Outside, enjoy the updated large cedar fenced backyard with a deck, patio and fire pit area, offering plenty of space for entertaining, gardening, pets, and outdoor activities. A versatile home offering comfortable living space, desirable features, and a convenient West Keene location!

66 Robbins Rd, 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

$695,000

3 Beds ⋅ 3 Baths ⋅ 5113128 MLS

Welcome to 146 Bryant Road. Nestled on a serene, 5 acre tree-lined lot, this beautiful contemporary new construction home offers the perfect blend of privacy, comfort and function. The stamped concrete farmers porch across the front of the home is the perfect place to enjoy morning coffee. Open concept interior with engineered hardwood floors, central ac and natural light throughout. Chef's kitchen complete with solid surface countertops, tile backsplash and stainless steel appliances. 1st floor primary bedroom boasts a large tiled bathroom, tiled walk-in shower and generous closet. Upstairs, 2 spacious bedrooms and a full bathroom. Convenient Walkout basement for storage or future living space. 2 car garage and paved driveway. Call today to schedule a showing!

146 Bryant Rd, Jaffrey

$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

$649,900

4 Beds ⋅ 3 Baths ⋅ 5113039 MLS

Welcome to 9 Schuyler Way, a beautifully maintained 4 Bedroom, 2.5 Bath home offering an impressive blend of space, privacy, and flexibility on 1.21 acres. Step inside to find refinished hardwood floors (2025) that bring warmth and a classic feel throughout the home. With over 3,000sq.ft. of finished space there is an abundance of room to live, work, entertain, and grow. The spacious layout is designed for comfortable everyday living and effortless entertaining with both living and family room spacing boasting gas fireplaces. Generously proportioned bedrooms include a primary suite that provides a private retreat at the end of the day. Plus, the 2nd floor laundry room saves you time and energy. The home's substantial finished lower level is a standout feature, offering tremendous flexibility for a home office, recreation space, guest accommodations, studio, or potential for ADU -style living arrangement, subject to applicable approvals. Located on a nice private cul-de-sac, 9 Schuyler Way remains close to all that Keene NH has to offer, you will find this 1.21 acre setting provides plenty of room to relax, entertain, garden and cook a smore on the fire pit. Come experience the setting, space and possibilities for yourself. Showings to start Friday October 9th as well as Open House 10/9 4-6:30

9 Schuyler Way, Keene

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