Cheshire County, NH Homes

• 

  

  

  /60

  $775,000

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  2221 Valley Rd, Stoddard, NH 03464

  Tucked away on Valley Road you will find this charming year-round cape on .43 acres with 105 ft of exclusively owned water frontage on the desirable Highland Lake! This home is positioned to maximize lake views overlooking a peaceful and private cove. This home is tastefully landscaped and thoughtfully designed, with no detail overlooked. Some recent upgrades were made including the installation

  Abby Fino

  2221 Valley Rd, Stoddard, NH 03464
• 

  

  

  /53

  $350,000

  Sold Jul 24, 2025

  125 Westport Village Rd, Swanzey, NH 03446

  • 3 Beds
  • 2 Baths
  • 1,849 Sq Ft
  • Built 1900

  Last Sold Summary

  • $189/SF
  • 48 Days On Market

  Current Estimated Value $354,948

  Last Listing Agent Norma Couture BHG Masiello Keene

  125 Westport Village Rd, Swanzey, NH 03446
• 

  

  

  /17

  Est $256,657

  Not Listed For Sale

  76 Mechanic St, Winchester, NH 03470

  • 4 Beds
  • 1 Bath
  • 1,918 Sq Ft
  • Built 1900

  76 Mechanic St, Winchester, NH 03470

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /50

  $799,900

  $200K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  78 Colburn Ln, Rindge, NH 03461

  LAKE LIFE at it's best! Set along the shores of Lake Monomonac, this property is all about the water, the view, and the lifestyle. Enjoy an unobstructed 180 panorama across the lake, including a front-row view of Commodore Island—the heart of lake life and a true gathering place for the community. From your deck, you’ll have a direct line of sight to summer highlights like the July 4th boat

  Denise Thomas BHG Masiello Keene

  78 Colburn Ln, Rindge, NH 03461
• 

  

  

  /24

  $132,500

  Sold Apr 13, 2026

  32 Main St, Hinsdale, NH 03451

  • 3 Beds
  • 4 Baths
  • 3,221 Sq Ft
  • Built 1856

  Last Sold Summary

  • 35% Below List Price
  • $41/SF
  • 227 Days On Market

  Current Estimated Value $214,840

  Last Listing Agent A.J. Bellville Bellville Realty

  32 Main St, Hinsdale, NH 03451
• 

  

  /18

  Not Listed For Sale

  161 Keene Rd, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft
  • Built 1880

  161 Keene Rd, Winchester, NH 03470

  Last Sold Summary

  • 70 Days On Market
• 

  

  /43

  $790,000

  • 3 Beds
  • 3 Baths
  • 2,790 Sq Ft

  216 Old Forest Rd, Stoddard, NH 03464

  Escape to the peace and beauty of New Hampshire's Monadnock Region with this exceptional retreat nestled in a private country setting. Tucked away among mature trees and surrounded by nature, this property offers the rare combination of seclusion, tranquility, and direct water frontage. Whether you're seeking a year-round residence, weekend getaway, or investment opportunity, you'll appreciate

  Denise Whitney BHG Masiello Peterborough

  216 Old Forest Rd, Stoddard, NH 03464
• 

  

  /44

  $380,000

  Sold Aug 22, 2025

  6 Mcgregor Ln, Rindge, NH 03461

  • 4 Beds
  • 4 Baths
  • 2,680 Sq Ft
  • Built 1977

  Last Sold Summary

  • 2% Below List Price
  • $142/SF
  • 3 Days On Market

  Current Estimated Value $417,106

  Last Listing Agent Maria Isotti Appleshed Realty

  6 Mcgregor Ln, Rindge, NH 03461
• 

  

  /32

  Est $315,215

  Not Listed For Sale

  57 Old Westport Rd, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft
  • Built 1987

  57 Old Westport Rd, Winchester, NH 03470

  Last Sold Summary

  • 19 Days On Market
• 

  

  /22

  $319,000

  • 3 Beds
  • 1.5 Baths
  • 1,805 Sq Ft

  7 Purcell Rd, Ashuelot, NH 03441

  Roomy, solidly built Post & Beam home awaits your tasteful touches and TLC! Enter this center-foyer cape by way of the spacious front covered porch built to enjoy many of our glorious New England seasons. Inside, the three main first-floor rooms offer options for living, dining, family room or den. A sizeable room off the kitchen can store all that seasonal gear or remain a walk-in pantry. Brand

  Barbara Cleveland Century 21 Highview Realty

  7 Purcell Rd, Ashuelot, NH 03441
• 

  

  /33

  $1,000,000

  Sold May 13, 2026

  241 Skatutakee Rd, Harrisville, NH 03450

  • 2 Beds
  • 1 Bath
  • 1,070 Sq Ft
  • Built 1965

  Last Sold Summary

  • 20% Below List Price
  • $935/SF
  • 304 Days On Market

  Current Estimated Value $814,493

  Last Listing Agent Pamela Thomas Coldwell Banker Realty Bedford NH

  241 Skatutakee Rd, Harrisville, NH 03450
• 

  

  /19

  Est $289,279

  Not Listed For Sale

  111 Howard St, Winchester, NH 03470

  • 3 Beds
  • 1 Bath
  • 1,602 Sq Ft
  • Built 1922

  111 Howard St, Winchester, NH 03470

  Last Sold Summary

  • 19 Days On Market
• 

  

  /40

  $689,000

  • 2 Beds
  • 3 Baths
  • 2,532 Sq Ft

  495 N Shore Rd, Chesterfield, NH 03462

  Welcome to lake living at its finest! This beautifully maintained 2-3 bedroom, 3 bath home offers sweeping views of picturesque Spofford Lake and is just a short walk to two local beaches. Whether you're looking for a year-round residence, vacation getaway, or an investment opportunity for Airbnb/rental income, this property offers endless possibilities. Inside, you’ll find a fully applianced

  Charlotte Marrocco-Mohler BHHS Verani Nashua

  495 N Shore Rd, Chesterfield, NH 03462
• 

  

  /17

  $425,000

  Sold Apr 14, 2026

  143 Village Rd, Surry, NH 03431

  • 2 Beds
  • 1.5 Baths
  • 1,603 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $265/SF
  • 6 Days On Market

  Current Estimated Value $421,498

  Last Listing Agent Susan Doyle BHG Masiello Keene

  143 Village Rd, Surry, NH 03431
• 

  

  /39

  Est $382,916

  Not Listed For Sale

  97 Howard St, Winchester, NH 03470

  • 4 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Built 2007

  97 Howard St, Winchester, NH 03470

  Last Sold Summary

  • 3 Days On Market
• 

  

  /42

  $475,000

  Open Fri 4PM - 6PM $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,822 Sq Ft

  175 River St, Keene, NH 03431

  Tucked away on a quiet cul-de-sac just minutes from downtown Keene, this home offers the perfect balance of neighborhood living and easy access to everything the city has to offer. Inside, you'll find a bright and airy main living area with vaulted ceilings and abundant natural light. The thoughtful layout includes a first-floor primary bedroom with ensuite and oversized walk-in closet making

  Kelsey Malloy Keller Williams Realty Metro-Keene

  175 River St, Keene, NH 03431
• 

  

  /28

  $344,000

  Sold Oct 24, 2025

  43 Old Stage Rd, Hinsdale, NH 03451

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft
  • Built 1968

  Last Sold Summary

  • 1% Above List Price
  • $159/SF
  • 9 Days On Market

  Current Estimated Value $352,130

  Last Listing Agent Robert Calkins Calkins Realty LLC

  43 Old Stage Rd, Hinsdale, NH 03451
• 

  

  /15

  Est $281,958

  Not Listed For Sale

  29 Michigan St, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 1,239 Sq Ft
  • Built 1900

  29 Michigan St, Winchester, NH 03470

  Last Sold Summary

  • 10 Days On Market
• 

  

  /39

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 1,524 Sq Ft

  102 Goodell Ave, Swanzey, NH 03446

  Opportunity awaits in a desirable Swanzey neighborhood surrounded by well-maintained homes. This 1850 Cape sits on over 5 acres and offers tremendous potential for buyers looking to restore and build equity. The property features 3 bedrooms, 11⁄2 baths, a newer barn built in 2023, and a chicken coop/shed, providing flexibility for hobby farming, storage, livestock, or workshop space. Several

  Denise Thomas BHG Masiello Keene

  102 Goodell Ave, Swanzey, NH 03446
• 

  

  /60

  $763,000

  Sold Aug 15, 2025

  236 Main St, Jaffrey, NH 03452

  • 4 Beds
  • 2.5 Baths
  • 3,105 Sq Ft
  • Built 1790

  Last Sold Summary

  • 4% Below List Price
  • $246/SF
  • 39 Days On Market

  Current Estimated Value $727,969

  Last Listing Agent Matthew Cabana EXP Realty

  236 Main St, Jaffrey, NH 03452
• 

  

  /22

  Est $318,533

  Not Listed For Sale

  16 Chapel St, Winchester, NH 03470

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 2025

  16 Chapel St, Winchester, NH 03470

  Last Sold Summary

  • 27 Days On Market
• 

  

  /42

  $495,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft

  27 Boulder Dr, Dublin, NH 03444

  Welcome to 27 Boulder Drive in Dublin, a charming Cape-style home offering the perfect blend of comfort, functionality, and natural beauty. Built in 1975 and set on 2.78 acres with frontage on White Pond, this residence provides direct water access and tranquil pond views in a private, wooded setting. The home features 3 bedrooms, 2.5 baths, and over 1,700 square feet of finished living space. A

  Sadie Halliday EXP Realty

  27 Boulder Dr, Dublin, NH 03444
• 

  

  /38

  $329,500

  Sold Jun 01, 2026

  20 Gates Rd Unit B15, Marlborough, NH 03455

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $190/SF
  • 73 Days On Market

  Last Listing Agent Wesley St. Pierre Keller Williams Realty Metro-Keene

  20 Gates Rd Unit B15, Marlborough, NH 03455
• 

  

  /25

  Not Listed For Sale

  21 Mechanic St, Winchester, NH 03470

  • 4 Beds
  • 2 Baths
  • 2,006 Sq Ft
  • Built 1900

  21 Mechanic St, Winchester, NH 03470

  Last Sold Summary

  • 8 Days On Market
• 

  

  /60

  $395,000

  $30K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  785 Brattleboro Rd, Hinsdale, NH 03451

  Spacious & Inviting Home in a Convenient Location! Ideally located just minutes from Brattleboro and I-91, this wonderful home offers the perfect blend of comfort, space, and convenience. The first floor features a bright bedroom with abundant natural light and a handicap-accessible bath complete with a beautiful walk-in tile shower — ideal for single-level living or guests. Enjoy cooking and

  Carol Slocum Keller Williams Realty Metro-Keene

  785 Brattleboro Rd, Hinsdale, NH 03451
• 

  

  /51

  $581,000

  Sold Oct 24, 2025

  45 Monadnock View Rd, Rindge, NH 03461

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $256/SF
  • 74 Days On Market

  Current Estimated Value $605,608

  Last Listing Agent Dean Deschenes Arris Realty

  45 Monadnock View Rd, Rindge, NH 03461
• 

  

  /25

  Not Listed For Sale

  44 Michigan St, Winchester, NH 03470

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1850

  44 Michigan St, Winchester, NH 03470

  Last Sold Summary

  • 45 Days On Market
• 

  

  /29

  $115,000

  $30K PRICE DROP

  • Land
  • 21.2 Acres
  • $5,425 per Acre

  525 Richmond Rd, Winchester, NH 03470

  Discover a rare opportunity to own 21.2+/- acres of pristine New Hampshire wilderness in the heart of Winchester. This expansive parcel is defined by its stunning frontage along the tranquil Roaring Brook, offering a picturesque and peaceful setting for your future dream home or private getaway. A standout feature of this property is its significant standing timber value; the land has remained

  Bob Barnard Monadnock Realty Group LLC

  525 Richmond Rd, Winchester, NH 03470
• 

  

  /24

  $38,000

  Sold Jul 01, 2025

  10 Starling St, Keene, NH 03431

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft
  • Built 1972

  Last Sold Summary

  • 24% Below List Price
  • $45/SF
  • 17 Days On Market

  Last Listing Agent Kirsten Perkins BHG Masiello Keene

  10 Starling St, Keene, NH 03431
• 

  

  /40

  Est $329,285

  Not Listed For Sale

  21 Keene Rd, Winchester, NH 03470

  • 5 Beds
  • 2.5 Baths
  • 4,678 Sq Ft
  • Built 1790

  21 Keene Rd, Winchester, NH 03470

  Last Sold Summary

  • 38 Days On Market
• 

  

  /58

  $640,000

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  25 Orchard Ln, Gilsum, NH 03448

  Tucked away in a peaceful setting, this handcrafted 11⁄2-story farmhouse offers charm, character, and thoughtful craftsmanship throughout. The heart of the home is the beautiful post-and-beam kitchen, featuring custom cabinetry, tile flooring, ample storage, and included appliances. Just off the kitchen, the pantry/mudroom provides exceptional functionality with a utility sink, coat closet,

  Bruce Murphy Keller Williams Realty Metro-Keene

  25 Orchard Ln, Gilsum, NH 03448
• 

  

  /60

  $495,900

  Sold Mar 02, 2026

  1100 Route 12a, Surry, NH 03431

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $246/SF
  • 53 Days On Market

  Current Estimated Value $501,800

  Last Listing Agent Emily Lagerberg R.H. Thackston & Company

  1100 Route 12a, Surry, NH 03431
• 

  

  /39

  Est $243,546

  Not Listed For Sale

  15 Old Mill Ct, Winchester, NH 03470

  • 4 Beds
  • 1 Bath
  • 1,792 Sq Ft
  • Built 1900

  15 Old Mill Ct, Winchester, NH 03470

  Last Sold Summary

  • 7 Days On Market
• 

  

  /34

  $274,900

  New Construction $5K PRICE DROP

  • 1,536 Sq Ft

  1046 Kings Hwy, Stoddard, NH 03464

  Secluded on a hill is this quaint, ready-to-be-completed cabin in this low-taxed, beautiful New Hampshire town. Enjoy watching the sunrise or viewing the fall foliage on this elevated 3.2 acre lot without a neighbor in sight. A 3 bedroom septic is already installed and ready to go. The 24'x32' footprint has a loft for additional living space or storage, and a full walk-out basement offers plenty

  Connie Lester Broadvest Real Estate Group

  1046 Kings Hwy, Stoddard, NH 03464
• 

  

  /33

  $688,000

  Sold Oct 10, 2025

  15 Meetinghouse Rd, Keene, NH 03431

  • 4 Beds
  • 2.5 Baths
  • 1,968 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $350/SF
  • 6 Days On Market

  Current Estimated Value $678,180

  Last Listing Agent Vicky Pratt Monadnock Realty Group LLC

  15 Meetinghouse Rd, Keene, NH 03431
• 

  

  /18

  Est $280,382

  Not Listed For Sale

  31 Hildreth St, Winchester, NH 03470

  • 3 Beds
  • 1 Bath
  • 1,405 Sq Ft
  • Built 1896

  31 Hildreth St, Winchester, NH 03470

  Last Sold Summary

  • 7 Days On Market
• 

  

  /32

  $299,900

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft

  200 Glebe Rd, Westmoreland, NH 03467

  Loads of potential with this 2–3 bedroom, 2-bath split level ranch home located in the desirable town of Westmoreland. The main level offers two bedrooms, a full bath, comfortable living room, and kitchen with dining area. A sliding glass door leads to the back deck, providing a great space to relax or entertain. The lower level features a rec room, three-quarter bath, laundry room, and a third

  Michelle Howe BHG Masiello Keene

  200 Glebe Rd, Westmoreland, NH 03467
• 

  

  /40

  $340,000

  Sold Dec 23, 2025

  16 Jewett St, Marlborough, NH 03455

  • 4 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Built 1870

  Last Sold Summary

  • 3% Below List Price
  • $241/SF
  • 32 Days On Market

  Last Listing Agent Deb Farrow Coldwell Banker Realty Nashua

  16 Jewett St, Marlborough, NH 03455
• 

  

  /6

  Not Listed For Sale

  4 Pine Ct, Winchester, NH 03470

  • 3 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 2010

  4 Pine Ct, Winchester, NH 03470

  Last Sold Summary

  • 4 Days On Market
• 

  

  /19

  $85,000

  Pending

  • Land
  • 1.5 Acres
  • $56,667 per Acre

  00 Forrest Dr Unit 50, Marlborough, NH 03455

  Your Monadnock dream home starts here. Tucked away at the very end of a quiet, established cul-de-sac, this pristine 1.5-acre building lot on Forrest Drive offers the perfect blend of absolute privacy and small-town New England charm. If you’ve been searching for the ideal canvas to design your dream home, this is it. Situated at the dead end of the road, the property ensures zero through traffic

  Bob Barnard Monadnock Realty Group LLC

  00 Forrest Dr Unit 50, Marlborough, NH 03455

Showing Results 561 - 600, Page 15 of 18