Vintage homes for sale & real estate in Cheshire County, NH

68 homes

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NEW 22 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Cheshire County, NH:
Charming 1925 Bungalow in N Swanzey, just minutes From downtown Keene and amenities. This 2-bedroom bungalow offers convenient one-level living and a great blend of classic character and modern improvements. Recent upgrades include new windows throughout the home and added insulation in the attic and basement for enhanced comfort and efficiency. While the home is move-in ready, it still offers the opportunity for updates and personal touches if so desired. The fenced-in backyard provides a cozy outdoor space for pets, gardening, or relaxing, and the low-maintenance lot keeps upkeep simple. A 1-car garage adds useful storage and convenience. This property makes an excellent starter home, a c

$257,500

2 beds1 bath911 sq ft

64 Old Homestead Hwy, North Swanzey, NH 03431

Fenced in backyard • Low maintenance lot • 1 car garage

NEW 23 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Cheshire County, NH:
Nestled in the heart of Spofford , Village, this inviting 3-bedroom, 2-bath home blends classic character with modern updates. Beautifully crafted curved walls add unique architectural appeal, while the updated kitchen offers both style and functionality to include exercise rm and sauna . Enjoy relaxing on the welcoming farmer’s porch, perfect for morning coffee or evening unwinding. A spacious two-car garage provides ample storage, including a full loft area above. This home offers comfort, charm, and convenience in a desirable location, only minutes to Spofford Lake. Includes a one yr Home Warranty. Showings start Wed Dec 3

$429,000

3 beds2 baths2,611 sq ft

48 Church St, Spofford, NH 03462

Sauna • Full loft area • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in Cheshire County, NH:
ATTENTION INVESTORS!! Here is a great rehab project. House is being sold 'AS IS" . Cash sale or Rehab loan only. Old barn is unsafe and will need to be taken down. But the house has potential. Buyers do their own due diligence.

$225,000

3 beds1 bath1,533 sq ft

34 E Lake Rd, Fitzwilliam, NH 03447-9998

2.6 acre lot • Built 1885 • Listed 2 days

NEW 16 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Cheshire County, NH:
Prime Investment Opportunity in the Heart of Keene, NH! Secure a high-value, income-producing property in one of Keene’s most convenient locations. This well-maintained 2-unit multifamily includes a massive, versatile partitioned barn, a rare asset that delivers exceptional upside and flexibility. Both units offer 3 bedrooms and 1 bathroom with fully separate utilities (one oil furnace, one gas furnace, individual circuit panels, and electric water heaters), keeping expenses simple and largely tenant-responsible. One unit is vacant, making it ideal for an owner-occupant house hack or for placing a new tenant at market rent immediately. Enjoy manageable yard space as well. The oversiz

$325,000

6 beds2 baths2,496 sq ft

49-51 Howard St, Keene, NH 03431

Customizable space • 5,662 sq ft lot • Built 1900

ABOUT THIS HOME
Vintage Home for sale in Cheshire County, NH:
A grand 2700+ sq. ft. Colonial ready to be reborn. Perched proudly above Terrace Street in the heart of the Monadnock Region, just steps from the historic bell tower, this once-magnificent residence is waiting for its next visionary. With roots tracing back to the Valley Woolen Mill and later cherished by the Morse family for more than 80 years, this property offers history, character—and incredible upside. Major improvements were completed in the late 1990s, including wiring, plumbing, and electric. Approximately 2018 new architectural shingle roof and in 2021, the exterior was refreshed with paint, replacement windows, new gutters, and a new furnace. Inside, the home still boasts it

$225,000

3 beds1.5 baths2,127 sq ft

26 Terrace St, Marlborough, NH 03455

New gutters • Colonial • Historic bell tower

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 9 Templeton Tpke, Fitzwilliam, NH 03447, 5 beds, 2.5 baths

$614,800

5 beds2.5 baths3,878 sq ft

9 Templeton Tpke, Fitzwilliam, NH 03447

Property at 194 Marlboro St, Keene, NH 03431, 2 beds, 2 baths

$279,900

2 beds2 baths1,824 sq ft

194 Marlboro St, Keene, NH 03431

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

$199,900

2 beds2 baths1,060 sq ft

82 Howard St, Winchester, NH 03470

Property at 40 Charlonne St, Jaffrey, NH 03452, 1 bath

$250,000

0 beds1 bath4,680 sq ft

40 Charlonne St, Jaffrey, NH 03452

Property at 21 Clark Rd, Winchester, NH 03470, 1 bed, 1 bath

$169,900

1 bed1 bath840 sq ft

21 Clark 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

Property at 16 Jewett St, Marlborough, NH 03455, 4 beds, 2 baths

$349,900

4 beds2 baths1,411 sq ft

16 Jewett St, Marlborough, NH 03455

Property at 37 Church St #3, Keene, NH 03431, 2 beds, 1.5 baths

$349,000

2 beds1.5 baths1,052 sq ft

37 Church St #3, Keene, NH 03431

Property at 471 Chapman Rd, Keene, NH 03431, 3 beds, 1.5 baths

$575,000

3 beds1.5 baths2,560 sq ft

471 Chapman Rd, Keene, NH 03431

Property at 106 Pako Ave, Keene, NH 03431, 2 beds, 2 baths

$325,000

2 beds2 baths2,312 sq ft

106 Pako Ave, Keene, NH 03431

Property at 50 Forest St, Keene, NH 03431

$395,000

— beds— baths2,490 sq ft

50 Forest St, Keene, NH 03431

Property at 26 Old North Main St, Walpole, NH 03608, 5 beds, 3.5 baths

$845,000

5 beds3.5 baths4,804 sq ft

26 Old North Main St, Walpole, NH 03608

Property at 16 Stone Rd, Stoddard, NH 03464, 2 beds, 1 bath

$765,000

2 beds1 bath1,689 sq ft

16 Stone Rd, Stoddard, NH 03464

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

$349,000

4 beds2 baths1,425 sq ft

821 Route 9, West Chesterfield, NH 03466

Property at 61 Elm St, Walpole, NH 03608, 5 beds, 3.5 baths

$750,000

5 beds3.5 baths3,958 sq ft

61 Elm St, Walpole, NH 03608

Property at 22 Fairfield Ct, Keene, NH 03431, 3 beds, 1 bath

$310,000

3 beds1 bath1,143 sq ft

22 Fairfield Ct, Keene, NH 03431

Property at 9 Center St, North Walpole, NH 03609, 3 beds, 1.5 baths

$315,000

3 beds1.5 baths1,497 sq ft

9 Center St, North Walpole, NH 03609

Property at 15 Waters Edge Rd, North Swanzey, NH 03446, 2 beds, 1.5 baths

$295,000

2 beds1.5 baths1,215 sq ft

15 Waters Edge Rd, North Swanzey, NH 03446

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

$690,000

4 beds2.5 baths2,436 sq ft

24 Sawyers Crossing Rd, Swanzey, NH 03446

Property at 15 Jennison St, Keene, NH 03431, 5 beds, 2 baths

$359,900

5 beds2 baths2,785 sq ft

15 Jennison St, Keene, NH 03431

Property at 4 Windmill Hill Rd, Dublin, NH 03444, 13 beds, 9.5 baths

$9,999,000

13 beds9.5 baths14,546 sq ft

4 Windmill Hill Rd, Dublin, NH 03444

Property at 41 Hillside Ave, Keene, NH 03431, 4 beds, 2 baths

$355,900

4 beds2 baths2,440 sq ft

41 Hillside Ave, Keene, NH 03431

Property at 14 Hurricane Rd, Westmoreland, NH 03467, 7 beds, 3.5 baths

$1,395,000

7 beds3.5 baths5,704 sq ft

14 Hurricane Rd, Westmoreland, NH 03467

Property at 1025 Route 123, Stoddard, NH 03464, 2 beds, 1.5 baths

$309,900

2 beds1.5 baths1,345 sq ft

1025 Route 123, Stoddard, NH 03464

Property at 46 Belmont Ave, Keene, NH 03431, 4 beds, 2 baths

$337,900

4 beds2 baths1,656 sq ft

46 Belmont Ave, Keene, NH 03431

Property at 257 Park Ave, Keene, NH 03431, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths1,752 sq ft

257 Park Ave, Keene, NH 03431

Property at 431 Main St, Keene, NH 03431, 4 beds, 2 baths

$499,500

4 beds2 baths2,579 sq ft

431 Main St, Keene, NH 03431

Property at 40 Jaffrey Rd, Marlborough, NH 03455, 3 beds, 2 baths

$349,900

3 beds2 baths1,820 sq ft

40 Jaffrey Rd, Marlborough, NH 03455

Property at 32 Main St, West Chesterfield, NH 03451, 3 beds, 4 baths

$195,000

3 beds4 baths3,221 sq ft

32 Main St, West Chesterfield, NH 03451

Property at 28 Village Rd, Surry, NH 03431, 3 beds, 1.5 baths

$499,000

3 beds1.5 baths2,628 sq ft

28 Village Rd, Surry, NH 03431

Property at 91 Sullivan St, Keene, NH 03431, 3 beds, 1 bath

$249,900

3 beds1 bath720 sq ft

91 Sullivan St, Keene, NH 03431

Property at 27 Shadowland Rd, Alstead, NH 03602, 3 beds, 1 bath

$479,000

3 beds1 bath1,094 sq ft

27 Shadowland Rd, Alstead, NH 03602

Property at 26 Weidner Dr, Rindge, NH 03461, 1 bed, 1 bath

$374,000

1 bed1 bath470 sq ft

26 Weidner Dr, Rindge, NH 03461

Property at 89 Main St, Marlborough, NH 03455, 5 beds, 2 baths

$400,000

5 beds2 baths5,624 sq ft

89 Main St, Marlborough, NH 03455

Property at 153 Back Ashuelot Rd, Winchester, NH 03470, 3 beds, 3.5 baths

$355,000

3 beds3.5 baths2,688 sq ft

153 Back Ashuelot Rd, Winchester, NH 03470

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Vintage Homes for Sale in Cheshire County

There are currently 68 vintage homes for sale in Cheshire County at a median listing price of $440K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Cheshire County stay on the market for 56 days and receive 1 offers. This map is refreshed with the newest listings in Cheshire County every 15 minutes.

In the past month, 99 homes have been sold in Cheshire County. In addition to houses in Cheshire County, there were also 35 condos, 1 townhouse, and 14 multi-family units for sale in Cheshire County last month. Find your dream home in Cheshire County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Cheshire County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Cheshire County. If you're looking to sell your home in the Cheshire County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Cheshire County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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