Cheshire County, NH homes for sale & real estate

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ABOUT THIS HOME
Cheshire County, NH Homes for Sale
A home 250+ years in the making, has just been offered for the first time! A perfect representation where classic New England style meets brand new modern convenience and elegance. This 3-bedroom, 2.5-bath home features high end finishes, historic displays of craftsmanship, and an incredible vision that makes this house a home. The outside features field stone siding and harmonious landscaping all on a sprawling private parcel of 6.6 acres. Yes, you also have your very own, perfectly manicured, apple orchard, an oversized 3 car garage with ample additional storage, a gazabo, trellis, and much more. Inside you'll find a vaulted ceiling in the chef inspired kitchen featuring high end applianc

$1,125,000

3 beds2.5 baths4,048 sq ft

3 Apple Hl, Chesterfield, NH 03443

Field stone siding • Vaulted ceiling • Private parcel

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
Welcome to 166 Keene Road in Winchester, a charming 3-bedroom, 1.5-bath New Englander that combines classic character with thoughtful modern updates. This inviting home offers comfortable living spaces, abundant natural light, and a warm atmosphere that immediately feels like home. Recent improvements include an updated roof, solar panels for enhanced energy efficiency, a spacious back deck ideal for entertaining and outdoor enjoyment, fresh paint throughout the interior, updated light fixtures, and a new dishwasher, allowing the next owner to move in with confidence. The functional floor plan provides flexibility for everyday living, whether you're gathering with family, working from home,

$449,900

3 beds1.5 baths1,808 sq ft

166 Keene Rd, Winchester, NH 03470

Spacious back deck • Fresh paint • Updated roof

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
Nestled along a picturesque country road in the charming town of Walpole, this gracious 1791 Colonial is a rare opportunity to own a true piece of New Hampshire history. Just minutes from the tranquil Connecticut River, this stately home has been welcoming generations for more than two centuries and is ready for its next steward. Offering over 4,000 square feet of living space, the home is rich with the warmth and character that only time can create. Wide pine floors, soaring ceilings, and four original decorative (non-working) fireplaces speak to its remarkable heritage, while generous rooms provide plenty of space for gathering with family and friends. Covered porches invite you to slow d

$499,900

4 beds2 baths4,078 sq ft

95 North Rd, Walpole, NH 03608

Covered porches • Large attached barn • Soaring ceilings

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
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

$584,900

5 beds3 baths2,660 sq ft

67 Park Ave, Keene, NH 03431

New primary bath • Vinyl harvey windows • Updated kitchen

ABOUT THIS HOME
Cheshire County, NH Homes for Sale
Located in the desirable Wright Estate, this condominium is nestled within a 16-acre wooded setting centered around the historic Wright Mansion. Residents enjoy beautifully maintained park-like grounds, scenic walking trails and tennis courts. This second-floor unit offers a lovely view of the historic mansion. The efficient galley kitchen includes a peninsula that opens to the living area, creating an inviting space for everyday living and entertaining while keeping the cook connected to family and guests. A convenient laundry room is located just off the kitchen. The primary bedroom features a private bath and a walk-in closet. Ideally situated just minutes from downtown, the hospital, sc

$257,000

2 beds2 baths1,071 sq ft

15 Windsor Ct Unit G, Keene, NH 03431

Galley kitchen • Tennis courts • Park like grounds

Property at 79 West Lake Rd, Fitzwilliam, NH 03447, 2 beds, 1 bath

$225,000

2 beds1 bath1,260 sq ft

79 West Lake Rd, Fitzwilliam, NH 03447

Property at 110 Upper Jaffrey Rd, Dublin, NH 03444, 2 beds, 2 baths

$499,000

2 beds2 baths2,022 sq ft

110 Upper Jaffrey Rd, Dublin, NH 03444

Property at 27 Sheehan Ln, Harrisville, NH 03450, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths2,092 sq ft

27 Sheehan Ln, Harrisville, NH 03450

Property at 24 Sawyers Crossing Rd, Swanzey, NH 03446, 4 beds, 2.5 baths

$565,000

4 beds2.5 baths2,398 sq ft

24 Sawyers Crossing Rd, Swanzey, NH 03446

Property at 40 Wilford St, Keene, NH 03431, 2 beds, 2 baths

$325,000

2 beds2 baths1,632 sq ft

40 Wilford St, Keene, NH 03431

Property at 96 Miller Dr, Nelson, NH 03457, 5 beds, 2 baths

$2,950,000

5 beds2 baths2,676 sq ft

96 Miller Dr, Nelson, NH 03457

Property at 61 Winter St, Keene, NH 03431, 6 beds, 4 baths

$555,000

6 beds4 baths3,608 sq ft

61 Winter St, Keene, NH 03431

Property at 25 Base Hill Rd, Keene, NH 03431, 3 beds, 2.5 baths

$387,500

3 beds2.5 baths2,424 sq ft

25 Base Hill Rd, Keene, NH 03431

Property at 32 Atlantic Dr, Rindge, NH 03461, 4 beds, 2.5 baths

$739,000

4 beds2.5 baths3,655 sq ft

32 Atlantic Dr, Rindge, NH 03461

Property at 407 Middle Winchendon Rd, Rindge, NH 03461, 4 beds, 2 baths

$549,000

4 beds2 baths1,986 sq ft

407 Middle Winchendon Rd, Rindge, NH 03461

Property at 40 Mill Rd, Richmond, NH 03470-4804, 4 beds, 2 baths

$449,000

4 beds2 baths2,542 sq ft

40 Mill Rd, Richmond, NH 03470-4804

Property at 78 Colburn Ln, Rindge, NH 03461, 3 beds, 1.5 baths

$749,000

3 beds1.5 baths1,404 sq ft

78 Colburn Ln, Rindge, NH 03461

Property at 26 Blue Jay Ct, Keene, NH 03431, 2 beds, 1 bath

$74,000

2 beds1 bath576 sq ft

26 Blue Jay Ct, Keene, NH 03431

Property at 45 Roberts Dr #24, Jaffrey, NH 03452, 3 beds, 2.5 baths

$849,900

3 beds2.5 baths2,400 sq ft

45 Roberts Dr #24, Jaffrey, NH 03452

Property at 373 Route 9A, Chesterfield, NH 03443, 4 beds, 2.5 baths

$650,000

4 beds2.5 baths2,984 sq ft

373 Route 9A, Chesterfield, NH 03443

Property at 190 Ashuelot St, Winchester, NH 03470, 3 beds, 1 bath

$120,000

3 beds1 bath1,457 sq ft

190 Ashuelot St, Winchester, NH 03470

Property at 484 Scofield Mountain Rd, Winchester, NH 03470, 3 beds, 2 baths

$599,000

3 beds2 baths2,516 sq ft

484 Scofield Mountain Rd, Winchester, NH 03470

Property at 26 Pleasant St, Alstead, NH 03602, 4 beds, 2 baths

$249,999

4 beds2 baths2,402 sq ft

26 Pleasant St, Alstead, NH 03602

Property at 31 Crowcroft Dr, Rindge, NH 03461, 2 beds, 2 baths

$549,000

2 beds2 baths1,284 sq ft

31 Crowcroft Dr, Rindge, NH 03461

Property at 356 NH Rt 119, Rindge, NH 03461, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths2,005 sq ft

356 NH Rt 119, Rindge, NH 03461

Property at 47 Maplewood Cir, Walpole, NH 03608, 4 beds, 2 baths

$439,900

4 beds2 baths2,442 sq ft

47 Maplewood Cir, Walpole, NH 03608

Property at 350 Woodbound Rd, Jaffrey, NH 03452, 2 beds, 1 bath

$530,000

2 beds1 bath1,550 sq ft

350 Woodbound Rd, Jaffrey, NH 03452

Property at 39 Plantation Way, Fitzwilliam, NH 03447, 2 beds, 1 bath

$149,700

2 beds1 bath674 sq ft

39 Plantation Way, Fitzwilliam, NH 03447

Property at 21 Hancock St, Keene, NH 03431, 3 beds, 1 bath

$335,000

3 beds1 bath1,278 sq ft

21 Hancock St, Keene, NH 03431

Property at 137 Prescott Rd, Jaffrey, NH 03452, 5 beds, 2.5 baths

$589,900

5 beds2.5 baths3,564 sq ft

137 Prescott Rd, Jaffrey, NH 03452

Property at 17 Sheila Ave, West Chesterfield, NH 03466, 4 beds, 2 baths

$250,000

4 beds2 baths1,854 sq ft

17 Sheila Ave, West Chesterfield, NH 03466

Property at 33 Queens Rd, Keene, NH 03431, 5 beds, 3.5 baths

$769,000

5 beds3.5 baths4,264 sq ft

33 Queens Rd, Keene, NH 03431

Property at 2 A-H Valley Creek Ln, Swanzey, NH 03446, 20 beds, 12 baths

$2,829,000

20 beds12 baths9,504 sq ft

2 A-H Valley Creek Ln, Swanzey, NH 03446

Property at 35 Salisbury Rd, Keene, NH 03431, 5 beds, 3 baths

$624,900

5 beds3 baths2,671 sq ft

35 Salisbury Rd, Keene, NH 03431

Property at 15 Elmi Dr, Rindge, NH 03461, 3 beds, 2 baths

$664,900

3 beds2 baths2,845 sq ft

15 Elmi Dr, Rindge, NH 03461

Property at 37 Base Hill Rd, Keene, NH 03431, 3 beds, 1.5 baths

$380,000

3 beds1.5 baths1,484 sq ft

37 Base Hill Rd, Keene, NH 03431

Property at 423 Old Walpole Rd, Keene, NH 03431, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths2,276 sq ft

423 Old Walpole Rd, Keene, NH 03431

Property at 71 Headlands Rd, Winchester, NH 03470, 3 beds, 2 baths

$445,000

3 beds2 baths1,066 sq ft

71 Headlands Rd, Winchester, NH 03470

Property at 108 Prospect St, Troy, NH 03465, 2 beds, 1 bath

$350,000

2 beds1 bath1,245 sq ft

108 Prospect St, Troy, NH 03465

Property at 131 Friedsam Dr, Chesterfield, NH 03443, 3 beds, 3 baths

$724,500

3 beds3 baths3,210 sq ft

131 Friedsam Dr, Chesterfield, NH 03443

Property at 294 Matthews Rd, Swanzey, NH 03446, 3 beds, 1 bath

$270,000

3 beds1 bath1,072 sq ft

294 Matthews Rd, Swanzey, NH 03446

Viewing page 4 of 8

Average home prices near Cheshire County, NH

Cities

Counties

Windham County homes for sale
$485,000
Hillsborough County homes for sale
$565,900
Merrimack County homes for sale
$549,000

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)

$398,666

+6.3% YoY | Aug 2026

1 year
3 year
5 year

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

Location

Data

Aug 2026

Growth

% YoY

Cheshire County, NH

$398,666

+6.3%

See more Cheshire County, NH market insights

More to explore in Cheshire County, NH

How to buy a house in Cheshire County, NH

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First-time homebuyer's guide

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5 Redfin agents serving Cheshire County

169

Deals*

4.8

Satisfaction

1065

Homes closed*

* Data from the last year

Popular Markets in New Hampshire

Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Mon Sep 21 2026 on the search page

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