Cheshire, NH Homes

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  /15

  $1,125,000

  • 5 Beds
  • 4.5 Baths
  • 5,846 Sq Ft

  13 Harkness Rd, Jaffrey, NH 03452

  Welcome to 13 Harkness Road, a rare opportunity to own a piece of New England history. Originally built in 1790 and once home to the beloved Rice’s Hotel, this elegant estate offers timeless charm. Set on over 3 picturesque acres in the heart of the Monadnock Region, this 5-bedroom, 5-bathroom residence is a masterclass in heritage craftsmanship and sophisticated living.From the moment

  

  Zack LeRoy

  BHG Masiello Keene

  (844) 855-1450

  13 Harkness Rd, Jaffrey, NH 03452
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  /22

  $1,750 per month

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Condo for Rent

  8 Christian Ct, Jaffrey, NH 03452

  This three family property offers very large, full floor apartments with both front/back porches. There is on site parking and a small back yard. Each apartment has washer and dryer appliances. Well maintained property located on a quiet dead-end side street, walkable to downtown Jaffrey and convenient drive to Peterborough, Keene, Milford and surrounding communities. Large attractive, sunny

  8 Christian Ct, Jaffrey, NH 03452
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  /38

  $537,000 Sold Aug 21, 2025

  • 2,350 Sq Ft
  • $229/SF
  • 39 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2004

  38 Howard Hill Rd, Jaffrey, NH 03452

  Welcome to this spacious and beautifully updated 4-bedroom, 3 3/4 bath cape nestled in a prime location in Jaffrey, NH. Featuring brand new flooring on both the first and second levels, this home combines classic charm with modern convenience. The open-concept kitchen, living, and dining area creates a bright, flowing space perfect for everyday living and entertaining.Enjoy the ease of a

  Stephanie Schubert Anagnost Realty & Development

  38 Howard Hill Rd, Jaffrey, NH 03452
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  /39

  Est $1,062,389 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,948 Sq Ft

  439 Gilmore Pond Rd, Jaffrey, NH 03452

  439 Gilmore Pond Rd, Jaffrey, NH 03452
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  /37

  $549,900

  • 2 Beds
  • 2 Baths
  • 1,788 Sq Ft

  57 Prescott Rd, Jaffrey, NH 03452

  Discover the perfect blend of classic New England charm and thoughtful modern updates in this beautifully crafted Antique Reproduction Saltbox Colonial, set on 1.76 private, landscaped acres. Built in 1979, this home features wide pine floors, custom woodwork, and period-style finishes throughout. The formal living room offers rich wood paneling, Indian shutters, and a brick fireplace. A spacious

  

  Sharon Corr

  The Corr Group, LLC

  (844) 512-0428

  57 Prescott Rd, Jaffrey, NH 03452
• 

  

  /22

  $1,800 per month

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Condo for Rent

  8 Christian Ct, Jaffrey, NH 03452

  This three family property offers very large, full floor apartments with both front/back porches. There is on site parking and a small back yard. Each apartment has washer and dryer appliances. Well maintained property located on a quiet dead-end side street, walkable to downtown Jaffrey and convenient drive to Peterborough, Keene, Milford and surrounding communities. Large attractive, sunny

  8 Christian Ct, Jaffrey, NH 03452
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  /27

  $316,000 Sold Aug 15, 2025

  • 1,152 Sq Ft
  • $274/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1967

  17 Hathorn Rd, Jaffrey, NH 03452

  Welcome to your next opportunity in scenic Jaffrey, NH! This classic ranch-style home sits on an open and sun-filled 2-acre lot, offering the perfect setting for gardening, play, or simply enjoying the outdoors. Featuring three bedrooms and one full bathroom, this home provides a smart layout and just the right amount of space for comfortable living. The full basement is ready for your finishing

  Samuel Abbott III Duston Leddy Real Estate

  17 Hathorn Rd, Jaffrey, NH 03452
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  /8

  Not Listed For Sale

  63 Turner Rd, Jaffrey, NH 03452

  63 Turner Rd, Jaffrey, NH 03452
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  /60

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,910 Sq Ft

  175 Hadley Rd, Jaffrey, NH 03452

  SIMPLY SPECIAL! Please come see this immaculate 2,910 sf Colonial being sold by it’s original owner. Enter into a gracious center hall, which has handsome hardwood floors as does most of the first level. To the right through French doors, is the sunny living room and to the left, a good-sized formal dining room accessing the lovely kitchen complete with a center island, full appliances and plenty

  

  Marc Tieger

  Tieger Realty Co. Inc.

  (855) 606-3931

  175 Hadley Rd, Jaffrey, NH 03452
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  /20

  $1,450 - $1,500 per month

  Jaffwood Apartments

  1 - 2 Beds

  142 Main St, Jaffrey, NH 03452

  Offering one and two bedroom units, our Jaffwood Apartments are a convenient and comfortable place to call home in Jaffrey. Conveniently located close to a main road and near to the center of town, the apartments are set back slightly in the woods to cut back on noise and increase privacy.

  142 Main St, Jaffrey, NH 03452
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  /47

  $525,000 Sold Aug 15, 2025

  • 1,878 Sq Ft
  • $280/SF
  • 2 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1962

  156 Bryant Rd, Jaffrey, NH 03452

  Hidden on 11.31 acres of serene woodland, sits an exceptional dormered cape style home which offers exceptional privacy, views of Mount Monadnock, and an unmatched connection to nature. This meticulously maintained 3 bedroom, 3 bath home features double-thick exterior walls for superior energy efficiency and year-round comfort. Inside, you'll find a warm and inviting layout that reflects pride of

  Dean Deschenes Arris Realty

  156 Bryant Rd, Jaffrey, NH 03452
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  /28

  Est $663,530 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  90 Overview Dr, Jaffrey, NH 03452

  90 Overview Dr, Jaffrey, NH 03452
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  /36

  $395,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  31 Letourneau Dr, Jaffrey, NH 03452

  Welcome to this beautifully maintained 3-bedroom, 2-bath ranch—offering the perfect blend of comfort, style, and low-maintenance living. Whether you're a first-time homebuyer or looking to downsize, this charming home provides everything you need in a manageable and inviting space. Step inside to find gleaming hardwood floors, pellet stove, and an open-concept layout that enhances the sense of

  Sherre Dubis Redfin Corporation

  31 Letourneau Dr, Jaffrey, NH 03452
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  /60

  $763,000 Sold Aug 15, 2025

  • 3,105 Sq Ft
  • $246/SF
  • 39 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1790

  236 Main St, Jaffrey, NH 03452

  Plan to stay a while when you come to visit this stately and gracious home, there are many details to absorb. Built to last with the superior construction of yesteryear, the grand front entrance boasts a wide hallway and elegant staircase, as you would expect in a home of this vintage. Clearly built for the "upper crust" of the time, the ceilings are high and the rooms very generously sized,

  Matthew Cabana EXP Realty

  236 Main St, Jaffrey, NH 03452
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  /13

  Not Listed For Sale

  • 9 Beds
  • 7 Baths
  • 4,139 Sq Ft

  101 Main St, Jaffrey, NH 03452

  101 Main St, Jaffrey, NH 03452
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  /33

  $549,900

  • 4 Beds
  • 3 Baths
  • 2,462 Sq Ft

  16 Harriet Ln, Jaffrey, NH 03452

  Just a short 2-minute walk to scenic Lake Contoocook with deeded beach and lake access, this modern home offers the perfect blend of comfort, convenience, and recreation. The sun-filled living room with gleaming hardwood floors flows seamlessly into the open-concept kitchen and dining area, ideal for entertaining. A spacious first-floor primary suite features a walk-in closet and private en suite

  Minghua Li Redfin Corporation

  16 Harriet Ln, Jaffrey, NH 03452
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  /58

  $500,000 Sold Aug 13, 2025

  • 2,552 Sq Ft
  • $196/SF
  • 62 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1792

  278 Great Rd, Jaffrey, NH 03452

  Gorgeous post & beam antique colonial, with addition for the 1st floor primary suite with cathedral ceiling, walk-in closet and full bath and sliders facing the view of grand Mt Monadnock! Amazing location with 12 acres +/- with about half of the lot being rolling open field and pasture. Sunlight pours through and showcases the beautiful historical woodwork, floors, exposed beams and massive

  Ryan Goodell EXP Realty

  278 Great Rd, Jaffrey, NH 03452
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  /33

  Est $337,654 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,710 Sq Ft

  9 Webster St, Jaffrey, NH 03452

  9 Webster St, Jaffrey, NH 03452
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  /52

  $749,900

  • 5 Beds
  • 4 Baths
  • 3,872 Sq Ft

  24 Red Gate Rd, Jaffrey, NH 03452

  SUITABLE FOR YOUR LIFESTYLE! Are you looking for a beautiful country home w/mountain view? Maybe a home office or possible Accessory Dwelling Unit? Whichever you would like, it's here! Situated on 4+ private acres w/pastoral view of Gap Mountain, about 1/2 hour from Keene, the quality is evident in every aspect of this lovely custom built home. To the left as you enter the gracious center hall is

  Marc Tieger Tieger Realty Co. Inc.

  24 Red Gate Rd, Jaffrey, NH 03452
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  /24

  $683,242 Sold Aug 11, 2025

  • 2,011 Sq Ft
  • $340/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  0 Roberts Dr Unit 22 5040179, Jaffrey, NH 03452

  The "Paxton" is a 3-bedroom 3-bathroom farmhouse colonial. The combination of farmhouse style and colonial architecture offers a timeless charm, and a floorplan that versatile enough to accommodate different lifestyles, from entertaining guests to working from home. The setting at the foot of Mount Monadnock and Stony Brook meandering through the development provide a truly unique

  Denise Whitney BHG Masiello Peterborough

  0 Roberts Dr Unit 22 5040179, Jaffrey, NH 03452
• 

  

  /23

  Est $442,851 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  715 Gilmore Pond Rd, Jaffrey, NH 03452

  715 Gilmore Pond Rd, Jaffrey, NH 03452
• 

  

  /57

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 3,388 Sq Ft

  75 Main St, Jaffrey, NH 03452

  Historic POOLE House with new paint, roof, solar power and boiler on 8+ acres in-town near the library, churches, Park Theater, art, restaurants, schools, & town hall. Excellent workmanship: built-ins, window seats, moulding, glass curtained or solid panelled doors, hardwood floors throughout. Front entry with two coat closets opens to a lovely foyer and sweeping bridal staircase. Right is large

  Heather Peterson Four Seasons Sotheby's International Realty

  75 Main St, Jaffrey, NH 03452
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  /59

  $515,000 Sold Aug 11, 2025

  • 2,623 Sq Ft
  • $196/SF
  • 160 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1904

  69 Main St, Jaffrey, NH 03452

  Step back in time and fall in love with this stunning 1904 antique Colonial located in the heart of Jaffrey, NH. This in-town treasure combines the best of historic charm and modern living. Original woodwork, elegant pocket doors, and dazzling stained-glass windows set the tone for a warm and inviting atmosphere. High 9 foot and 8 foot ceilings and period lighting fixtures create a sense of

  Michelle Carter Four Seasons Sotheby's International Realty

  69 Main St, Jaffrey, NH 03452
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  /31

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  155 River St, Jaffrey, NH 03452

  155 River St, Jaffrey, NH 03452
• 

  

  /50

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 3,207 Sq Ft

  158 Great Rd, Jaffrey, NH 03452

  Welcome to 158 Great Road, a spacious and beautifully updated 4-bedroom, 2.5-bath Colonial set on 5 private, landscaped acres in desirable Cheshire County. With over 3,200 sq ft of finished living space, this home blends timeless design with thoughtful, high-quality updates.The heart of the home is the renovated kitchen, featuring new cabinetry, counters are quartz with a custom walnut

  Sadie Halliday EXP Realty

  158 Great Rd, Jaffrey, NH 03452
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  /6

  $40,000 Sold Jul 31, 2025

  • 732 Sq Ft
  • $55/SF
  • 38 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1972

  47 Delta Dr, Jaffrey, NH 03452

  Affordable Living Near Contoocook Lake & Mount Monadnock!Enjoy the charm of Jaffrey in this 1972 manufactured home, ideally situated just minutes from outdoor recreation and scenic views. The home offers a practical layout with a bedroom on each end, a full bath, and convenient laundry area next to the primary bedroom. The spacious living room flows directly from the kitchen, and a covered

  Alissa DelTufo East Key Realty

  47 Delta Dr, Jaffrey, NH 03452
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  /35

  Est $383,157 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  25 Annette Rd, Jaffrey, NH 03452

  25 Annette Rd, Jaffrey, NH 03452
• 

  

  /59

  $599,000

  • 5 Beds
  • 2.5 Baths
  • 2,906 Sq Ft

  29 Dean Farm Rd, Jaffrey, NH 03452

  Welcome to 29 Dean Farm Road, a beautifully maintained home set in the heart of New Hampshire’s scenic Monadnock Region. This spacious 5-bedroom, 2.5-bath residence offers a timeless blend of warmth, comfort, and functionality. Gleaming hardwood floors run throughout the home, complementing generously sized bedrooms and a flexible floor plan that includes a first-floor office or study. The sun

  Dean Deschenes Arris Realty

  29 Dean Farm Rd, Jaffrey, NH 03452
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  /38

  $365,000 Sold Jul 29, 2025

  • 1,776 Sq Ft
  • $206/SF
  • 3 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1935

  70 River St, Jaffrey, NH 03452

  Welcome home to River Street! Conveniently located near Jaffrey center and famous Mount Monadnock this IS the home you've been looking for. Situated on a level lot with ample parking, enjoy the large fenced in backyard for relaxation and outdoor play. The backyard features a patio with a stone fire pit and an outdoor power supply for all your entertaining needs. Upon entering the home you'll find

  Kenny Laughters East Key Realty

  70 River St, Jaffrey, NH 03452
• 

  

  /35

  Est $434,442 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft

  7 Beth Cir, Jaffrey, NH 03452

  7 Beth Cir, Jaffrey, NH 03452
• 

  

  /59

  $619,900

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

  137 Prescott Rd, Jaffrey, NH 03452

  Steeped in history and timeless charm, this distinguished Colonial home, built circa 1830, offers a rare glimpse into the past while providing endless possibilities for modern living. A true treasure for history enthusiasts, the home proudly showcases original murals by the renowned artist Rufus Porter (1792–1884), whose work has been celebrated in museums and historic homes throughout New

  Dean Deschenes Arris Realty

  137 Prescott Rd, Jaffrey, NH 03452
• 

  

  /23

  $100,000 Sold Jul 22, 2025

  • 990 Sq Ft
  • $101/SF
  • 5 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1900

  31 North St, Jaffrey, NH 03452

  The major updates are already complete—now it's just down to your finishing touches! This in-town home features a newer roof, aluminum siding, and updated windows. The electrical panel and boiler have also been upgraded, offering peace of mind and a solid foundation for your cosmetic improvements. Located on a manageable lot with sidewalks leading straight to downtown Jaffrey, this property

  Matthew Despres Keller Williams Realty-Metropolitan

  31 North St, Jaffrey, NH 03452
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  /37

  Est $419,890 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft

  275 Hadley Rd, Jaffrey, NH 03452

  275 Hadley Rd, Jaffrey, NH 03452
• 

  

  /24

  $759,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,011 Sq Ft

  0 Roberts Dr Unit 24 5041429, Jaffrey, NH 03452

  The "Paxton" is a 3-bedroom 3-bathroom farmhouse colonial. The combination of farmhouse style and colonial architecture offers a timeless charm, and a floorplan that versatile enough to accommodate different lifestyles, from entertaining guests to working from home. The setting at the foot of Mount Monadnock and Stony Brook meandering through the development provide a truly unique

  Denise Whitney BHG Masiello Peterborough

  0 Roberts Dr Unit 24 5041429, Jaffrey, NH 03452
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  /25

  $365,000 Sold Jul 21, 2025

  • Land
  • 12 Acres
  • $31,277 per Acre

  • 23 Days On Market

  420 Peterborough St, Jaffrey, NH 03452

  Beautiful 11.67-Acre Building Lot – Ready to Build!Discover the perfect blend of privacy and convenience on this stunning 11.67-acre lot. Perched up in a peaceful setting with its own babbling brook, this property is ready for your dream home with a driveway already roughed in, power on site, and a state-approved 4-bedroom septic design in hand.Enjoy the serenity of nature with plenty of

  Dean Deschenes Arris Realty

  420 Peterborough St, Jaffrey, NH 03452
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  /36

  Est $386,925 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,480 Sq Ft

  12 Evergreen Ln, Jaffrey, NH 03452

  12 Evergreen Ln, Jaffrey, NH 03452
• 

  

  /31

  $784,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,059 Sq Ft

  0 Roberts Dr Unit 5 5030097, Jaffrey, NH 03452

  The Hudson is a 4-bedroom 3-bathroom home with a stunning view of Grand Monadnock! The combination of farmhouse style and colonial architecture offers a timeless charm, and a floorplan that versatile enough to accommodate different lifestyles, from entertaining guests to working from home. The setting at the foot of Mount Monadnock and Stony Brook meandering through the development provide a

  Denise Whitney BHG Masiello Peterborough

  0 Roberts Dr Unit 5 5030097, Jaffrey, NH 03452
• 

  

  /25

  $400,000 Sold Jul 14, 2025

  • 1,512 Sq Ft
  • $265/SF
  • 39 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  353 North St, Jaffrey, NH 03452

  MULTIPLE OFFERS. HIGHEST & BEST DEADLINE 9 AM ON 06/12/25. Tucked away on a long, scenic driveway, this home's elevated location, along with underground utilities, creates an unobstructed view of the yard. The multi-level deck offers ample opportunities to enjoy the surrounding nature, including a thoughtfully designed rock garden/retaining wall, and the sounds of a stream. Inside, the living

  Anna Schierioth HKS Associates, Inc.

  353 North St, Jaffrey, NH 03452
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  /38

  Est $538,526 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

  11 Sherwood Ln, Jaffrey, NH 03452

  11 Sherwood Ln, Jaffrey, NH 03452
• 

  

  /38

  $589,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,788 Sq Ft

  19 Lord View Dr, Jaffrey, NH 03452

  Be the first to own this beautifully designed 3-bedroom, 2.5 bath Cape Style home, offering 1,788 square feet of modern comfort and timeless charm. The clean white exterior, welcoming covered front porch, and attached 2-car garage create an inviting first impression.Step inside to a bright, open concept layout highlighted by a gorgeous kitchen featuring two-toned cabinetry, quartz countertops

  Andre Aho EXP Realty

  19 Lord View Dr, Jaffrey, NH 03452

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