Cheshire County, NH Homes

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  /59

  $589,900

  $20K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,564 Sq Ft

  137 Prescott Rd, Jaffrey, NH 03452

  Nestled in the heart of New Hampshire’s beloved Monadnock Region, this remarkable circa 1830 Colonial blends rich history, timeless craftsmanship, and breathtaking natural beauty into one extraordinary offering. Set against the backdrop of iconic Mount Monadnock views and overlooking a tranquil mill pond and brook, the property captures the very essence of classic New England living.A rare

  

  Dean Deschenes

  Arris Realty

  137 Prescott Rd, Jaffrey, NH 03452
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  /29

  $3,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,994 Sq Ft
  • House for Rent

  51 Cabot Ln, Walpole, NH 03608

  Updated single family home with 3 bedrooms, 2 baths, set in a spectacular rural setting in Walpole, NH. Located on a quiet rural road that offers serene pastoral views, close enough to enjoy rail trails, parking for 2 cars provided, garage available. Landlord has just updated this home by installing new windows, new lighting, fresh paint through out, NEW KITCHEN, new efficient Buderus furnace

  

  Robin Sanctuary

  Traditions Real Estate LLC

  51 Cabot Ln, Walpole, NH 03608
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  /17

  $284,900

  Sold Mar 02, 2026

  31 North St, Jaffrey, NH 03452

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $259/SF
  • 37 Days On Market

  Current Estimated Value $276,158

  Last Listing Agent Zachary Letourneau North New England Real Estate Group

  31 North St, Jaffrey, NH 03452
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  /60

  Not Listed For Sale

  115 Tigola Trail, Stoddard, NH 03464

  • 4 Beds
  • 4 Baths
  • 3,566 Sq Ft
  • Built 2026

  115 Tigola Trail, Stoddard, NH 03464

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Abby Fino
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  /36

  $220,000

  $30K PRICE DROP

  • Land
  • 3.3 Acres
  • $66,667 per Acre

  164 Gustin Pond Rd, Marlow, NH 03456

  New price improvement! Seller will consider all reasonable offers. There is still time to finish this unique opportunity this year by skipping months of construction delays. If you have always thought of building but overwhelmed as to where to start, this unique opportunity offers the perfect head start. Nestled on 3.3 private acres in a beautiful rural setting, this 26 x 48' Ranch is well

  

  Mary Ann Shepard

  Monadnock Region Real Estate Group, LLC

  164 Gustin Pond Rd, Marlow, NH 03456
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  /50

  Starting at $2,275 Per Month

  • Studio - 2 Beds

  3 Orchard Ln, Swanzey, NH 03446

  The Orchard Overlook Apartments is Swanzey's newest luxury community! This oasis offers many amazing amenities including a heated pool, fitness center, pickleball courts and a putting green!

  Orchard Overlook Apartments

  

  3 Orchard Ln, Swanzey, NH 03446
• 

  

  /17

  $295,000

  Sold Feb 27, 2026

  19 Toofs Dr, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Below List Price
  • $219/SF
  • 19 Days On Market

  Current Estimated Value $296,097

  Last Listing Agent Curtiss Thornbrugh HKS Associates, Inc.

  19 Toofs Dr, Winchester, NH 03470
• 

  

  /41

  Est $326,633

  Not Listed For Sale

  52 Christian Hill Rd, Swanzey, NH 03446

  • 2 Beds
  • 1.5 Baths
  • 2,285 Sq Ft
  • Built 1830

  52 Christian Hill Rd, Swanzey, NH 03446

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Lily Gautot Greenwald Realty Group
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  /40

  $350,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  169 Gilsum St, Keene, NH 03431

  Welcome to 169 Gilsum Street in Keene! This well-located 3–5-bedroom ranch is just minutes from downtown Keene and Keene State College. The main level features an open-concept kitchen and living area, a primary bedroom with a convenient ¾ bath, two additional bedrooms, and a full bath. The partially finished basement offers added flexibility with two bonus rooms, laundry room, another bonus room,

  

  Angeline Gorham

  BHHS Verani Realty Hampstead

  169 Gilsum St, Keene, NH 03431
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  /7

  $1,650 Per Month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  73 Main St Unit 1, Walpole, NH 03608

  In the village of Walpole, NH, conveniently located for easy access to shops, restaurants, library, Post Office, town buildings, and Walpole Common. Easy commute to Keene and Claremont, or 91 that gives access to North or South destinations.This space is designed to be light filled and airy, with 13' high ceilings, large windows and original hardwood floors. Kitchen/living room with lovely

  

  Robin Sanctuary

  Traditions Real Estate LLC

  73 Main St Unit 1, Walpole, NH 03608
• 

  

  /14

  $45,000

  Sold Jun 30, 2026

  00 Kennedy Brook Dr Unit 11, Stoddard, NH 03464

  • Land
  • 1.4 Acres
  • $32,143 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 292 Days On Market

  Last Listing Agent Brian Michaud Dow Hill Realty

  00 Kennedy Brook Dr Unit 11, Stoddard, NH 03464
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  /52

  Est $486,926

  Not Listed For Sale

  506 Old Walpole Rd, Surry, NH 03431

  • 2 Beds
  • 2 Baths
  • 1,906 Sq Ft
  • Built 1986

  506 Old Walpole Rd, Surry, NH 03431

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Deborah Lucey RE/MAX Town & Country
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  /11

  $199,900

  Under Contract

  • 2 Beds
  • 1 Bath
  • 616 Sq Ft

  22 Wetmore St, Keene, NH 03431

  Welcome to 22 Wetmore Street, a charming and efficient 2-bedroom, 1-bath home tucked away on a quiet dead-end street in Keene. Offering 616 square feet of comfortable living space, this open-concept home makes the most of every inch, with a practical layout that feels bright, welcoming, and easy to maintain.Recent updates include a new roof, new furnace, and new hot water heater, providing

  

  Laurie Mack

  BHG Masiello Keene

  22 Wetmore St, Keene, NH 03431
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  /32

  Starting at $1,660 Per Month

  • Studio - 2 Beds

  175 Monadnock Hwy, Swanzey, NH 03446

  Monadnock Place, Swanzey, NH’s premier luxury apartment community, is now Leasing! Discover the best of modern living in our spacious studio, one-, and two-bedroom apartments, all designed with high-end finishes. Monadnock Place features top tier amenities such as a cybercafé, social lounge, 24 hour-fitness center, pet spa, grilling stations and fire pits! Embrace a lifestyle of comfort and

  Monadnock Place

  

  175 Monadnock Hwy, Swanzey, NH 03446
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  /22

  $155,000

  Sold May 04, 2026

  4 Tara Hill Ln, Hinsdale, NH 03451

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1972

  Last Sold Summary

  • 30% Below List Price
  • $124/SF
  • 134 Days On Market

  Current Estimated Value $231,942

  Last Listing Agent Andrea Thackston R.H. Thackston & Company/Bellows Falls

  4 Tara Hill Ln, Hinsdale, NH 03451
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  /40

  Est $473,299

  Not Listed For Sale

  101 Robbins Rd, Rindge, NH 03461

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1984

  101 Robbins Rd, Rindge, NH 03461

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Lisa Small William Raveis R.E. & Home Services
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  /21

  $110,000

  $10K PRICE DROP Pending

  • Land
  • 2.09 Acres
  • $52,632 per Acre

  42 Bowl Rd, Richmond, NH 03470

  Build your dream home on this 2 Acre lot located in the private 100 Acre Morgan Reservation Association consisting on 35 lots within a permanently protected forest of 460 Acres. Enjoy fishing, swimming, and kayaking/canoeing on Larry's pond which offers beautiful scenery. The lot already has power, a Well, and a storage shed.

  

  Matthew Straight

  Coldwell Banker Realty - Leominster

  42 Bowl Rd, Richmond, NH 03470
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  /16

  $2,400 Per Month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  13 Boggy Meadow Ln, Walpole, NH 03608

  Enjoy the peaceful setting of this 3-bedroom home located in Walpole's agricultural district, where open fields and rural surroundings create a quiet country atmosphere. Conveniently situated just minutes from downtown Walpole, with an easy commute to Keene, NH, and convenient access to Interstate 91, this home offers the perfect balance of privacy and accessibility.Located near local walking

  

  Robin Sanctuary

  Traditions Real Estate LLC

  13 Boggy Meadow Ln, Walpole, NH 03608
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  /45

  $285,000

  Sold May 26, 2026

  14 Hammann Dr, Marlow, NH 03456

  • 3 Beds
  • 1.5 Baths
  • 1,184 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $241/SF
  • 111 Days On Market

  Current Estimated Value $291,018

  Last Listing Agent Shane Moynihan Realty One Group Next Level

  14 Hammann Dr, Marlow, NH 03456
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  /54

  Not Listed For Sale

  573 Granite Lake Rd, Nelson, NH 03457

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 2003

  573 Granite Lake Rd, Nelson, NH 03457

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Linda Hitchcock BHG Masiello Keene
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  /40

  $399,000

  $36K PRICE DROP

  • 5,000 Sq Ft

  87 Mechanic St, Alstead, NH 03602

  Dreaming of riverfront living with income potential?This one-of-a-kind multi-family property overlooks the scenic Cold River, renowned for its excellent fishing opportunities. Rich in history, the building was originally a grist mill and has been thoughtfully converted into a three-unit multi-family property while preserving much of its original character.The first floor apartment is

  

  Robin Sanctuary

  Traditions Real Estate LLC

  87 Mechanic St, Alstead, NH 03602
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  /40

  Starting at $1,775 Per Month

  • Studio - 3 Beds

  222 West St, Keene, NH 03431

  Keene’s landmark Colony Mill has been fully renovated, and now features 89 pet-friendly loft apartments with sleek, modern kitchens, in-unit washer/dryer, central air, on-site fitness center, community gathering room, theatre room, Wifi lounge and off-street parking! Residents of Colony Mill are also sure to love the easy walk to Keene’s quaint downtown, which offers an excellent array of dining,

  Colony Mill

  

  222 West St, Keene, NH 03431
• 

  

  /28

  $235,000

  Sold Jun 12, 2026

  26 Stone Pond Rd, Marlow, NH 03456

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft
  • Built 1980

  Last Sold Summary

  • 34% Above List Price
  • $367/SF
  • 5 Days On Market

  Current Estimated Value $219,981

  Last Listing Agent Jonathan Griffus BHG Masiello Keene

  26 Stone Pond Rd, Marlow, NH 03456
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  /38

  Est $483,719

  Not Listed For Sale

  135 Number 4 Rd, Fitzwilliam, NH 03447

  • 3 Beds
  • 3 Baths
  • 2,560 Sq Ft
  • Built 2002

  135 Number 4 Rd, Fitzwilliam, NH 03447

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Robin Smith BHG Masiello Keene
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  /60

  $859,000

  $34K PRICE INCREASE Under Contract

  • 1 Bed
  • 1 Bath
  • 1,276 Sq Ft

  562 Alstead Center Rd, Alstead, NH 03602

  Properties like this rarely come available! Nestled on over 17 private acres, this beautifully built Craftsman-style home offers exceptional quality, privacy, and a lifestyle that feels worlds away from the everyday.From the moment you arrive, the inviting large front porch sets the tone for this peaceful retreat, providing the perfect spot to sit back, relax, and take in the surrounding

  

  Robin Sanctuary

  Traditions Real Estate LLC

  562 Alstead Center Rd, Alstead, NH 03602
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  /30

  Starting at $775 Per Month

  • 4 Beds

  120 Emerald St, Keene, NH 03431

  Off campus living is made easy with all-inclusive rent, fully furnished apartments, and amenities designed for students. Located just down the street from Keene State College, we offer individual lease agreements within spacious 3 or 4 bedroom floorplans. Call or email our leasing team to arrange for a personal tour and see for yourself why you will love living at Arcadia

  Arcadia Apartments

  

  120 Emerald St, Keene, NH 03431
• 

  

  /14

  $370,000

  Sold Jun 30, 2026

  44 Pearl St, Keene, NH 03431

  • 2,119 Sq Ft
  • Built 1850

  Last Sold Summary

  • $175/SF
  • 0 Days On Market

  Current Estimated Value $337,157

  Last Listing Agent No MLS Listing Agent No MLS Listing Office

  44 Pearl St, Keene, NH 03431
• 

  

  /36

  Est $295,542

  Not Listed For Sale

  126 Hill Rd, Alstead, NH 03602

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1992

  126 Hill Rd, Alstead, NH 03602

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Robert Westover Galloway Real Estate LLC
• 

  

  /60

  $720,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  341 Ingalls Rd, Jaffrey, NH 03452

  Imagine a place where life slows down, and nature, thoughtful design, and exceptional craftsmanship come together. Set on 5.06 acres, this 2,200-square-foot contemporary colonial offers a seamless connection to the outdoors. The three-bedroom, three-bath home combines the character of a carefully considered design with the efficiency of a home built in 2020. Nine-foot ceilings, solid white oak

  

  Peg Walsh

  Four Seasons Sotheby's International Realty

  341 Ingalls Rd, Jaffrey, NH 03452
• 

  

  /27

  Starting at $1,695 Per Month

  • 1 - 2 Beds

  24 Monadnock Hwy, Keene, NH 03431

  Princeton at Mill Pond Apartments for Rent in Keene, NH boasts exciting amenities such as heat and hot water included, pet friendly locations, online rent pay and maintenance notifications as well as reserved covered parking. Take a stroll around the property in a wooded peaceful environment to get some air and clear your head. Taking your four-legged friend out to play, there is plenty of

  Princeton at Mill Pond

  

  24 Monadnock Hwy, Keene, NH 03431
• 

  

  /55

  $475,000

  Sold May 05, 2026

  24 Village Rd, Surry, NH 03431

  • 3 Beds
  • 2 Baths
  • 2,111 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Below List Price
  • $225/SF
  • 153 Days On Market

  Current Estimated Value $480,138

  Last Listing Agent Ryan Goodell EXP Realty

  24 Village Rd, Surry, NH 03431
• 

  

  /20

  Not Listed For Sale

  Map 6 Lot 15-3 Off Opportunity Dr, Winchester, NH 03470

  Map 6 Lot 15-3 Off Opportunity Dr, Winchester, NH 03470

  Last Sold Summary

  • 1,005 Days On Market

  Last Listing Agent Penelope Seaver Coldwell Banker Realty Nashua
• 

  

  /59

  $875,000

  $124K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,757 Sq Ft

  20 Keene Ave, Fitzwilliam, NH 03447

  Experience the ultimate turnkey New England Lake retreat at 20 Keene Ave, a masterfully renovated compound set on a beautifully landscaped one-acre lot with coveted deeded beach access to pristine, spring-fed Laurel Lake. Both the main home and the detached Accessory Dwelling Unit (ADU) are fully winterized and designed for comfortable year-round living. This exceptional offering blends high-end

  

  Laurie Mack

  BHG Masiello Keene

  20 Keene Ave, Fitzwilliam, NH 03447
• 

  

  /20

  Starting at $1,129 Per Month

  • Studio - 2 Beds

  311-323 Maple Ave, Keene, NH 03431

  The Pines Apartments are located just a short distance from downtown Keene, New Hampshire, Keene Medical Center and major highways. Keene has so much to offer: great dining, shopping and the advantages of access to Keene State College. You can enjoy the view of Mt. Monadnock from our meticulously maintained grounds. Our pool is a great summertime meeting place. We are owner managed with pride for

  The Pines Apartments

  

  311-323 Maple Ave, Keene, NH 03431
• 

  /2

  $105,000

  Sold Aug 27, 2026

  113 Farm Rd, Surry, NH 03431

  • Land
  • 2.03 Acres
  • $51,724 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sandy Cormier Greenwald Realty Group

  113 Farm Rd, Surry, NH 03431
• 

  

  /16

  Est $410,375

  Not Listed For Sale

  140 W Hill Rd, Troy, NH 03465

  • 4 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 2021

  140 W Hill Rd, Troy, NH 03465

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Kellie Williams Keller Williams Realty Metro-Keene
• 

  

  /29

  $298,000

  $19K PRICE INCREASE

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  295 Gilsum Rd, Sullivan, NH 03445

  Welcome to 295 Gilsum Road in Sullivan, NH—a beautifully renovated 2-bedroom, 1-bath home set on 2 peaceful acres in a picturesque rural setting just 20 minutes from Keene. Back on the market due to the previous buyer’s inability to obtain financing.Every inch of this bright and sunny home has been thoughtfully updated, including a newly installed, state-approved septic system. The stunning

  

  Laurie Mack

  BHG Masiello Keene

  295 Gilsum Rd, Sullivan, NH 03445
• 

  

  /20

  Starting at $1,795 Per Month

  • 1 - 2 Beds

  742 W Swanzey Rd, Swanzey, NH 03446

  Princeton Square Apartments in Swanzey, NH offers comfortable, garden-style living in a peaceful, convenient setting just minutes from Keene. Choose from well-designed one and two bedroom apartment homes featuring functional layouts, ample closet space, and bright living areas that make it easy to feel at home. Enjoy beautifully maintained grounds, off-street parking, on-site laundry, and

  Princeton Square

  

  742 W Swanzey Rd, Swanzey, NH 03446
• 

  

  /60

  $730,000

  Sold Mar 17, 2026

  183 Tower Hill Rd, Hinsdale, NH 03451

  • 4 Beds
  • 3.5 Baths
  • 2,715 Sq Ft
  • Built 1992

  Last Sold Summary

  • 72% Above List Price
  • $269/SF
  • 6 Days On Market

  Current Estimated Value $583,809

  Last Listing Agent Jonathan Bafundi Realty One Group Next Level

  183 Tower Hill Rd, Hinsdale, NH 03451
• 

  

  /23

  Est $215,462

  Not Listed For Sale

  710 Main St Unit 4, Keene, NH 03431

  • 2 Beds
  • 1.5 Baths
  • 1,364 Sq Ft
  • Built 1985

  710 Main St Unit 4, Keene, NH 03431

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Shirley Marcello BHG Masiello Keene

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