Cheshire County, NH homes for sale & real estate

202 homes

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ABOUT THIS HOME
Cheshire County, NH Homes for Sale
If you’ve ever dreamed of buying an endearing farmhouse with a barn, this is your sign! Set against a backdrop of rolling countryside, this 18th century 3 bed 3 bath farmhouse with classic barn offers over 4,000± square feet of living space and a rare opportunity to own a property steeped in history. Lovingly held by the same family for 48 years, this home reflects generations of care, character, and timeless New England charm. Perfectly positioned halfway between Keene, NH and Brattleboro, VT, the property offers the best of rural living without isolation. You’re just 15 minutes to I-91, ~60 minutes from ski mountains, only five minutes from Spofford Lake, and just a sh

$669,000

3 beds3 baths4,001 sq ft

24 Hunt Rd, Westmoreland, NH 03467

30x40 barn • Endearing farmhouse • Classic barn

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
Welcome to this beautifully and thoughtfully renovated 3-bedroom, 1-bath home located on North Street in the heart of downtown Jaffrey. This property has been painstakingly updated from top to bottom, with no expense spared to create a bright, comfortable, and truly move-in-ready home. Every detail has been carefully considered, featuring brand-new appliances, elegant quartz countertops, and a fresh, modern interior that blends style with everyday functionality. Unlike many homes in the downtown area, this property offers the rare convenience of in-home washer and dryer hookups, adding meaningful practicality to its charm. The home has been fully insulated for improved comfort and energy ef

$299,900

3 beds1 bath1,100 sq ft

31 North St, Jaffrey, NH 03452

Fully insulated • Renovated home • Turnkey property

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
Contemporary 3-bedroom, 3 bath home with 2-car garage attached, with storage above, and separate 2-story post & beam barn. Home has newer galley kitchen with a lot of cabinets, stainless steel appliances. Floors are tiled, hard wood and carpet. Newer Primary suite on 2nd floor with tiled shower and own porch to back yard. Wood stove between the dining room and living room with spiral staircase to the 2nd floor. Outside there is a good-sized hoop green house, new large deck, shed, raised beds, 100 plants of different types of lavender and your own solar array for assistance with your electric bill. The barn would make a great shop or add onto home water & sewer, and you have addi

$599,000

3 beds3 baths2,037 sq ft

95 Blackjack Xing, Walpole, NH 03608

Large deck • Galley kitchen • Solar array

3D WALKTHROUGH

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
SERENE WOODED RETREAT! NATURE AND PRIVACY ABOUND IN THIS INVITING HOME! Set back from a pretty country road, a gently curving drive leads to a lovely reveal of a striking blue ranch framed by panoramic skies, stone walls and a sense of peaceful seclusion. A welcoming front porch invites you to enter through French doors into a sunlit living room enveloped in soft seaside tones, where pale wide-plank luxury vinyl flooring flows seamlessly through spaces. Relax in the living room with guests, or lose yourself in a book in the adjacent cozy reading nook. Work from home in a painted paneled office that provides ideal room for creativity, making or studies. Head to the happy heart of the home fo

$425,000

3 beds2 baths1,438 sq ft

1639 Main St, Dublin, NH 03444

One-level living • Wooded retreat • Refreshed kitchen

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
Peaceful Country Living at 21 Heights Lane – Sullivan, NH Tucked away on a quiet lane in the charming town of Sullivan, this property offers the perfect blend of privacy, nature, and New England character. Surrounded by scenic beauty and fresh country air, 21 Heights Lane is ideal for those seeking a tranquil retreat while still being within reach of nearby towns and amenities. Just 10 minutes to Downtown Keene. Enjoy a serene setting with ample outdoor space, perfect for relaxing, entertaining, or exploring the natural surroundings. Whether you’re looking for a full-time residence, a weekend getaway, or an investment opportunity, this property offers the calm and simplicity of

$324,900

2 beds1 bath1,080 sq ft

21 Heights Ln, Sullivan, NH 03445

1.25 acre lot • Built 1957 • Listed 7 days

Property at 14 Hammann Dr, Marlow, NH 03456-6435, 3 beds, 1.5 baths

$305,000

3 beds1.5 baths1,184 sq ft

14 Hammann Dr, Marlow, NH 03456-6435

Property at 7 Rogers St, Walpole, NH 03608, 3 beds, 2 baths

$574,000

3 beds2 baths1,790 sq ft

7 Rogers St, Walpole, NH 03608

Property at 657 New Hampshire Route 12 S, Fitzwilliam, NH 03447, 3 beds, 2 baths

$380,000

3 beds2 baths1,864 sq ft

657 New Hampshire Route 12 S, Fitzwilliam, NH 03447

Property at 78 Mackey Rd, Troy, NH 03465, 3 beds, 1.5 baths

$425,000

3 beds1.5 baths1,625 sq ft

78 Mackey Rd, Troy, NH 03465

Property at 787 Route 10, Gilsum, NH 03448, 2 beds, 2 baths

$379,000

2 beds2 baths1,420 sq ft

787 Route 10, Gilsum, NH 03448

Property at 521 County Rd, Walpole, NH 03608, 3 beds, 2 baths

$599,000

3 beds2 baths2,675 sq ft

521 County Rd, Walpole, NH 03608

Property at 11 Cream Pot Hill Rd, Hinsdale, NH 03451, 6 beds, 4.5 baths

$899,000

6 beds4.5 baths5,950 sq ft

11 Cream Pot Hill Rd, Hinsdale, NH 03451

Property at 534 Cobble Hill Rd, Swanzey, NH 03446, 3 beds, 3 baths

$730,000

3 beds3 baths3,212 sq ft

534 Cobble Hill Rd, Swanzey, NH 03446

Property at 34 E Lake Rd, Fitzwilliam, NH 03447-9998, 3 beds, 1 bath

$225,000

3 beds1 bath1,533 sq ft

34 E Lake Rd, Fitzwilliam, NH 03447-9998

Property at 259 Bolton Rd, Winchester, NH 03470, 2 beds, 2 baths

$899,000

2 beds2 baths3,472 sq ft

259 Bolton Rd, Winchester, NH 03470

Property at 130 Watson Rd, Winchester, NH 03470, 3 beds, 2 baths

$694,900

3 beds2 baths2,145 sq ft

130 Watson Rd, Winchester, NH 03470

Property at 658 Main St, Marlborough, NH 03455, 4 beds, 4 baths

$450,000

4 beds4 baths2,713 sq ft

658 Main St, Marlborough, NH 03455

Property at 1100 Route 12A, Surry, NH 03431, 3 beds, 2 baths

$509,900

3 beds2 baths2,016 sq ft

1100 Route 12A, Surry, NH 03431

Property at 64 Old Homestead Hwy, North Swanzey, NH 03431, 2 beds, 1 bath

$254,900

2 beds1 bath911 sq ft

64 Old Homestead Hwy, North Swanzey, NH 03431

Property at 19 Toofs Dr, Winchester, NH 03470, 3 beds, 2 baths

$299,000

3 beds2 baths1,344 sq ft

19 Toofs Dr, Winchester, NH 03470

Property at 103 Route 119 W, Fitzwilliam, NH 03447, 4 beds, 3.5 baths

$449,995

4 beds3.5 baths3,900 sq ft

103 Route 119 W, Fitzwilliam, NH 03447

Property at 98 Monadnock St, Troy, NH 03465, 3 beds, 2 baths

$325,000

3 beds2 baths1,272 sq ft

98 Monadnock St, Troy, NH 03465

Property at 127 Holbrook Ave, Swanzey, NH 03446, 3 beds, 1 bath

$320,000

3 beds1 bath1,012 sq ft

127 Holbrook Ave, Swanzey, NH 03446

Property at 64 Summit Dr, Jaffrey, NH 03452, 2 beds, 2 baths

$105,000

2 beds2 baths924 sq ft

64 Summit Dr, Jaffrey, NH 03452

Property at 82 Howard St, Winchester, NH 03470, 2 beds, 2 baths

$189,900

2 beds2 baths1,060 sq ft

82 Howard St, Winchester, NH 03470

Property at 66 Sugar Hill Rd, Swanzey, NH 03446, 3 beds, 1.5 baths

$425,000

3 beds1.5 baths1,580 sq ft

66 Sugar Hill Rd, Swanzey, NH 03446

Property at 85 Pierce Rd, Fitzwilliam, NH 03447, 10 beds, 6 baths

$1,200,000

10 beds6 baths3,984 sq ft

85 Pierce Rd, Fitzwilliam, NH 03447

Property at 14 Anthony Cir, Swanzey, NH 03446, 3 beds, 2 baths

$75,000

3 beds2 baths924 sq ft

14 Anthony Cir, Swanzey, NH 03446

Property at 603 Route 12A, Surry, NH 03431, 3 beds, 2.5 baths

$500,000

3 beds2.5 baths2,026 sq ft

603 Route 12A, Surry, NH 03431

Property at 849 Route 10, Gilsum, NH 03448, 4 beds, 2 baths

$795,000

4 beds2 baths3,492 sq ft

849 Route 10, Gilsum, NH 03448

Property at 4 Tara Hill Ln, Hinsdale, NH 03451, 3 beds, 1.5 baths

$199,000

3 beds1.5 baths1,248 sq ft

4 Tara Hill Ln, Hinsdale, NH 03451

Property at 206 New Hampshire Route 119 E, Fitzwilliam, NH 03447, 3 beds, 2 baths

$399,900

3 beds2 baths1,388 sq ft

206 New Hampshire Route 119 E, Fitzwilliam, NH 03447

Property at 22 Blue Jay Ct, Keene, NH 03431, 2 beds, 1 bath

$59,999

2 beds1 bath924 sq ft

22 Blue Jay Ct, Keene, NH 03431

Property at 821 Route 9, West Chesterfield, NH 03466, 4 beds, 2 baths

$314,000

4 beds2 baths1,425 sq ft

821 Route 9, West Chesterfield, NH 03466

Property at 1046 Kings Hwy, Stoddard, NH 03464

$279,900

0 beds— baths— sq ft

1046 Kings Hwy, Stoddard, NH 03464

Property at 26 Terrace St, Marlborough, NH 03455, 3 beds, 1.5 baths

$225,000

3 beds1.5 baths2,127 sq ft

26 Terrace St, Marlborough, NH 03455

Property at 269 Branch Rd, Roxbury, NH 03431, 2 beds, 2 baths

$349,900

2 beds2 baths1,248 sq ft

269 Branch Rd, Roxbury, NH 03431

Property at 12 Wetherby Dr, Winchester, NH 03470, 2 beds, 2 baths

$130,000

2 beds2 baths924 sq ft

12 Wetherby Dr, Winchester, NH 03470

Property at 17 Blue Jay Ct, Keene, NH 03431, 2 beds, 2 baths

$109,900

2 beds2 baths952 sq ft

17 Blue Jay Ct, Keene, NH 03431

Property at 240 Forest Lake Rd, Winchester, NH 03470, 4 beds, 2.5 baths

$610,000

4 beds2.5 baths2,200 sq ft

240 Forest Lake Rd, Winchester, NH 03470

Property at 142 Brattleboro Rd, Hinsdale, NH 03451, 3 beds, 1 bath

$279,000

3 beds1 bath1,053 sq ft

142 Brattleboro Rd, Hinsdale, NH 03451

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Average home prices near Cheshire County, NH

Cities

Counties

Windsor County homes for sale
$614,000
Hillsborough County homes for sale
$549,900
Merrimack County homes for sale
$499,999

Cheshire County, NH real estate trends

All Home Types trends in Cheshire County, NH

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$400,000

+7.5% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Cheshire County, NH

$400,000

+7.5%

See more Cheshire County, NH market insights

More to explore in Cheshire County, NH

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