Cheshire County NH 2-Story Homes for Sale

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  /22

  $997,000

  • 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 you step

  

  Zack LeRoy

  BHG Masiello Keene

  (844) 855-1450

  13 Harkness Rd, Jaffrey, NH 03452
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  /41

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,592 Sq Ft

  9 Rogers St, Walpole, NH 03608

  Charming Walpole, NH Village Home with Room to GrowWelcome to this spacious and inviting home, perfect for those seeking character, light filled rooms in living spaces, and located in easy walking distance to town amenities.The first floor offers a large living room with a cozy wood stove corner, a generous dining room, a kitchen with laundry with a breakfast nook around the corner. A

  

  Robin Sanctuary

  Traditions Real Estate LLC

  (844) 410-5220

  9 Rogers St, Walpole, NH 03608
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  /55

  $375,000

  • 4 Beds
  • 2.5 Baths
  • 2,135 Sq Ft

  161 Main St, Marlborough, NH 03455

  Energy-efficient historic charm defines this classic Greek Revival/New Englander. Major upgrades include new energy-efficient windows installed Feb–March 2026, a new side door, and refurbishment of the main door and seals (March 2026), enhancing comfort and helping reduce heating costs. The home’s symmetrical façade, window pediments, and columned open porch create a striking first impression.

  Paul Rodenhauser BHG Masiello Keene

  161 Main St, Marlborough, NH 03455
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  /50

  $529,000 Open Sat 10AM - 1PM

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  529 N Shore Rd, Chesterfield, NH 03462

  Don't miss this rare opportunity! You'll be pleasantly surprised when you see the charm and details of this Classic New England home. "And YES, it also has Income Potential." Walk inside and discover masterful craftsmanship, stunning wide plank flooring, hand hued beams, and expansive modern kitchen, with large island. This cute Cape also features an exquisite and peaceful sunroom, which has a

  Todd Bassler Greenwald Realty Group

  529 N Shore Rd, Chesterfield, NH 03462
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  /36

  $430,000

  • 3 Beds
  • 2.5 Baths
  • 1,477 Sq Ft

  10 Hillside Ave, Swanzey, NH 03446

  This beautifully remodeled home has been thoughtfully updated from top to bottom, offering peace of mind with a new roof, insulation, plumbing, heating system, electrical service, and stylishly renovated bathrooms and kitchen featuring modern fixtures. The first floor boasts a flexible layout with a convenient primary bedroom, a full bath, and a walk-in closet. Just off the kitchen, you’ll find a

  Anna Schierioth HKS Associates, Inc.

  10 Hillside Ave, Swanzey, NH 03446
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  /56

  $354,900

  • 4 Beds
  • 2.5 Baths
  • 2,054 Sq Ft

  66 Beech St, Keene, NH 03431

  Charming 1910 home with an updated look and the perfect mix of character and modern comfort. The spacious kitchen is made for gathering, featuring a farmhouse sink, stainless steel appliances, quartz countertops, recessed lighting, a large center island, and a walk-in pantry. A generous mudroom offers extra living space and could easily serve as a cozy sitting area with the gas fireplace stove.

  Robin Smith BHG Masiello Keene

  66 Beech St, Keene, NH 03431
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  /60

  $487,500 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,079 Sq Ft

  29 Grant St, Keene, NH 03431

  This beautifully maintained Keene home, walkable to downtown and Robin Hood Park, has a renovated, well-appointed kitchen with a convenient butler's pantry and a sizable office/eat-in combination space. The kitchen also has quartz countertops and a granite-topped island with nooks and crannies for all sorts of supplies. Surrounding it are two sitting rooms, a dining room, porch, mudroom and half

  Donna Moxley Keller Williams Realty Metro-Keene

  29 Grant St, Keene, NH 03431
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  /29

  $525,000

  • 10 Beds
  • 4 Baths
  • 3,647 Sq Ft

  116 Roxbury St, Keene, NH 03431

  Excellent 4 unit Multi-Family property in Keene. Consistently has been a money maker. Located only feet from Downtown Keene, well maintainedunits, excellent Tenant history that are long term, good storage. All systems well maintained. Newer hot air heating systems and on demand hot water. Consists of a 4 bedroom, 3 bedroom, 2 bedroom and anamazing 1 bedroom apartment over garage with

  Josh Greenwald Greenwald Realty Group

  116 Roxbury St, Keene, NH 03431
• 

  

  /22

  $340,000

  • 3 Beds
  • 1.5 Baths
  • 1,402 Sq Ft

  28 Stonehouse Ln, Keene, NH 03431

  Rich in warmth, comfort and ease, this home is your effortless choice when seeking the simplicity of condominium living and low maintenance life. Meticulously maintained throughout, the first-floor features maple hardwood flooring in the Kitchen, Great Room, stairs, and upstairs landing; all newer appliances; fresh interiors; and sunlit rooms. This home has been completed for you with

  Christine Lewis Brattleboro Area Realty

  28 Stonehouse Ln, Keene, NH 03431
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  /28

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,278 Sq Ft

  515 Washington St, Keene, NH 03431

  Charming 3-bedroom home with thoughtful upgrades and a flexible layout! The renovated kitchen is a standout, featuring a new stove, new sink, updated plumbing, new masonry work, and a brand-new island with prep sink—perfect for cooking and entertaining. The cabinet-packed space with stainless steel appliances opens to a cozy dining area with a wood stove and access to the two-tier back deck

  Kerryann Murphy Lamacchia Realty, Inc.

  515 Washington St, Keene, NH 03431
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  /10

  $300,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  82 Howard St, Winchester, NH 03470

  OPEN HOUSE SATURDAY 4/4 12-2PM Tasteful updates nearing completion to include an updated kitchen with new appliances, updated bathrooms, new floors, new paint throughout, public water, and sewer! A total refresh with zero headaches for years to come. Awesome value and quality uncommon in the market today for only $300,000. Home is currently almost complete with only weeks left grab this before

  Tyler Richer AmeraBay

  82 Howard St, Winchester, NH 03470
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  /29

  $490,000

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

  143 Arch St, Keene, NH 03431

  Ideally located in West Keene, this beautifully maintained home offers the perfect blend of comfort and convenience with tasteful upgrades . This desirable location includes easy access to local schools, downtown Keene, the hospital, major highways, and recreational opportunities. Some of the newly added features of this meticulously cared for home are hardwood floors throughout, a cozy propane

  Gerry Leo BHG Masiello Keene

  143 Arch St, Keene, NH 03431
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  /42

  $389,900

  • 3 Beds
  • 1.5 Baths
  • 1,784 Sq Ft

  136 George St, Keene, NH 03431

  Beautiful farmhouse with wrap around covered farmer's porch, solarium, 2 story barn on oversized lot in convenient location. This home has been loved, and lovingly maintained by the current owners for 57 years. Home interior features, the back room ( den office mudroom gathering area ) this area has a 1/2 bath and first floor laundry area, beautiful tile & oak kitchen w/corian tops, upgraded

  Chris Evans BHHS Verani Bedford

  136 George St, Keene, NH 03431
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  /49

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  452 Middle Winchendon Rd, Rindge, NH 03461

  Welcome Home! Set on a private and beautifully landscaped 2-acre lot, this exceptional new colonial offers the perfect blend of elegance, comfort, and modern design in a peaceful yet commuter-friendly location close to shopping, dining, and everyday conveniences. Step inside to a bright and welcoming open floor plan designed for both relaxed living and effortless entertaining. The dramatic great

  Erin Dinsmoor Keller Williams Realty-Metropolitan

  452 Middle Winchendon Rd, Rindge, NH 03461
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  /34

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft

  386 Old Chesham Rd, Marlborough, NH 03455

  Set gracefully along a quiet country road, this inviting home captures the essence of rural New England living, highlighted by sweeping views of Mount Monadnock. Horses occasionally pass along the road, adding to the timeless charm and peaceful atmosphere that define this special setting.Just a short drive from Keene, the property offers a thoughtful balance of privacy and convenience. The

  Alexa Thayer Four Seasons Sotheby's International Realty

  386 Old Chesham Rd, Marlborough, NH 03455
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  /21

  $400,000

  • 6 Beds
  • 3 Baths
  • 2,184 Sq Ft

  139 Squantum Rd, Jaffrey, NH 03452

  Located just a short walk from the town beach on Contoocook Lake, this spacious 6-bedroom, 3-bath home offers the opportunity to enjoy a relaxed lifestyle close to water, nature, and town conveniences. Set on a level 1.05-acre lot with generous yard space, there’s plenty of room for outdoor gatherings, gardening, or simply enjoying the open space. Originally a single-story home, the property was

  Jillian Exel BHG Masiello Keene

  139 Squantum Rd, Jaffrey, NH 03452
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  /34

  $360,000

  • 2 Beds
  • 1 Bath
  • 1,448 Sq Ft

  646 Court St, Keene, NH 03431

  Tucked into a convenient Keene location just minutes from downtown shops, restaurants and everyday amenities, this charming Cape offers warmth, character and a peaceful backyard setting with views of the Ashuelot river. Set on .46 acres, the property features a fully fenced backyard with a paver patio-perfect for relaxing, entertaining, or enjoying the natural beauty of the river just beyond,

  Kathryn Beam Galloway Real Estate LLC

  646 Court St, Keene, NH 03431
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  /42

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  549 West St, Keene, NH 03431

  Welcome to this charming circa 1929 Craftsman-style bungalow ideally situated in West Keene, close to schools, parks, and neighborhood amenities. This solidly built home showcases timeless architectural character including gleaming hardwood floors, a board & batten living room ceiling, wide wood trim, classic built-ins, and a cozy fireplace that anchors the spacious living area. The updated

  Tere Clarkson RE/MAX Town & Country

  549 West St, Keene, NH 03431
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  /21

  $339,900

  • 4 Beds
  • 1.5 Baths
  • 1,379 Sq Ft

  131 Marlboro St, Keene, NH 03431

  Step into timeless charm with this classic Four Square home set on a spacious corner lot, complete with a rare three-car detached garage. A welcoming front porch offers the perfect place to relax and enjoy warm New England days. Inside, character abounds with tin ceilings, rich hardwood floors, and beautiful natural woodwork throughout. The main level features a generously sized living room and

  Robin Smith BHG Masiello Keene

  131 Marlboro St, Keene, NH 03431
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  /46

  $649,999

  • 6 Beds
  • 4 Baths
  • 4,100 Sq Ft

  89 Butler Ave, Hinsdale, NH 03451

  Tucked away on a quiet hilltop, this charming home offers the perfect escape with views over the Connecticut river and mountains afar. A 900-foot private driveway welcomes you home with many opportunities any spacious parking. Designed with true first floor living, the main residence offers everyday functionality without compromise. Expansive windows flood the home with natural light. The open

  Katelyn Heaney Greenwald Realty Group

  89 Butler Ave, Hinsdale, NH 03451
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  /14

  $275,000

  • 2,904 Sq Ft

  68 Brattleboro Rd, Hinsdale, NH 03451

  Former Medical Office Building being sold as a multi-family property. First floor has excellent potential as a 2 bedroom apartment or 2 studio/1 bedroom units. There is plenty of plumbing in place to accommodate kitchens and bathrooms.The second floor is a large 2 Bedroom apartment with hardwood floors. There is a 2 car garage with a large great room above that has more potential as living

  Vincent Dolan RE/MAX Town & Country

  68 Brattleboro Rd, Hinsdale, NH 03451
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  /56

  $530,000

  • 3 Beds
  • 3.5 Baths
  • 2,742 Sq Ft

  411 Alstead Center Rd, Alstead, NH 03602

  Your Dream Country Escape Awaits!Welcome to this lovingly maintained 4-bedroom, 3.5-bath farmhouse, beautifully set on 5 picturesque acres of scenic farmland. Blending timeless charm with modern comfort, this property offers endless possibilities for country living at its finest. The outdoor amenities truly shine, featuring a spacious barn for storage, a 3-stall horse barn, a detached one-car

  Kerryann Murphy Lamacchia Realty, Inc.

  411 Alstead Center Rd, Alstead, NH 03602
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  /45

  $355,000

  • 3 Beds
  • 2 Baths
  • 2,020 Sq Ft

  20 Gates Rd Unit 11, Marlborough, NH 03455

  Exceptionally well cared for 3-bedroom, 2-bath townhouse condominium offering true easy living and extensive updates throughout. The home has been thoughtfully renovated and meticulously maintained, with most improvements completed within the last 8 years. Highlights include a fully renovated kitchen with new windows, cabinetry, counters, and appliances, along with two completely remodeled

  Michelle Carter Four Seasons Sotheby's International Realty

  20 Gates Rd Unit 11, Marlborough, NH 03455
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  /58

  $799,000

  • 6 Beds
  • 5.5 Baths
  • 5,600 Sq Ft

  360 Jaffrey Rd, Marlborough, NH 03455

  Country Estate located in the heart of the picturesque Monadnock Region with over 15 acres of pasture, woods and a year round pond. This property offers a unique blend of historical charm, timeless elegance and modern serenity. Equestrian property, a boutique vineyard, a small-scale organic farm or comfortable living with multi-generational flexibility ... live as you always imagined. Private in

  Judy Ilomaki BHG Masiello Hollis

  360 Jaffrey Rd, Marlborough, NH 03455
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  /24

  $329,900

  • 4 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  35 Foster St, Keene, NH 03431

  Welcome to this Fabulous 4-bedroom, 1.5-bath home ideally located just steps from downtown, Keene State College, shopping, schools, and parks. Inside, you’ll find beautiful hardwood floors, an updated open kitchen, vinyl windows, and a fresh, neutral paint palette throughout. The first floor offers flexible living with a sunny updated kitchen and living room, a convenient half bath(updated), a

  Robin Smith BHG Masiello Keene

  35 Foster St, Keene, NH 03431
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  /34

  $375,000

  • 2 Beds
  • 1 Bath
  • 1,404 Sq Ft

  11 Walnut St, Keene, NH 03431

  This fully renovated home offers quality finishes and thoughtful updates throughout, creating a fresh, move-in-ready space. The layout is both practical and comfortable, designed for easy everyday living. A spacious backyard—already 3⁄4 fenced—provides the perfect setting for outdoor gatherings, gardening, or simply enjoying your own space. Complete the enclosure for added privacy or to

  Christine Houston Greenwald Realty Group

  11 Walnut St, Keene, NH 03431
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  /54

  $719,900

  • 3 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  171 Dublin Rd, Harrisville, NH 03450

  Welcome to 171 Dublin Road in Harrisville, NH — a beautifully crafted 1,900 sq ft Colonial built in 2026. This quality-built new construction home blends modern efficiency with classic New England charm, set on a peaceful lot that abuts town land and offers slight views of Lake Shatutakee. A welcoming farmer’s porch sets the tone as you enter the bright, open first floor featuring luxury vinyl

  Larry Alvarez Tieger Realty Co. Inc.

  171 Dublin Rd, Harrisville, NH 03450
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  /43

  $899,999

  • 4 Baths
  • 3,108 Sq Ft

  60 Dearborn Cir, Walpole, NH 03608

  This mixed-use property features a spacious, dedicated office which comprises the complete first floor, ideal for remote work or running a home-based business. The office offers ample room for multiple workstations, built-in storage, and abundant natural light, creating a productive and comfortable environment. The 7-room office has reception area, large conference room, 3 private offices and a

  Cynthia Westover Galloway Real Estate LLC

  60 Dearborn Cir, Walpole, NH 03608
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  /48

  $835,000

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

  78 Colburn Ln, Rindge, NH 03461

  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 parade and the Monomonac Lake

  Denise Thomas BHG Masiello Keene

  78 Colburn Ln, Rindge, NH 03461
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  /45

  $295,000

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

  14 Hammann Dr, Marlow, NH 03456

  Welcome to 14 Hammann Drive in Marlow, NH. A peaceful wooded property with tons of potential. This 3-bedroom, 1.5-bath ranch offers a functional layout, hardwood floors, and warm wood accents throughout. The home does need updating and TLC, but the bones are solid and it’s a great opportunity for renovation or investment. Large windows bring in plenty of natural light, and the surrounding pines

  Shane Moynihan Realty One Group Next Level

  14 Hammann Dr, Marlow, NH 03456
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  /59

  $1,200,000

  • 10 Beds
  • 6 Baths
  • 3,984 Sq Ft

  85 Pierce Rd, Fitzwilliam, NH 03447

  The possibilities with this remarkable property are truly endless! Set on 78+ acres of open fields and forest, 85 Pierce Road offers exceptional privacy, flexibility, and opportunity in a beautiful rural setting. This unique estate features a spacious primary residence and a large dormitory-style building with expansive common areas, providing incredible versatility for creative residential or

  Jesse Gadarowski Eric W Callahan

  85 Pierce Rd, Fitzwilliam, NH 03447
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  /60

  $849,900

  • 3 Beds
  • 2 Baths
  • 3,472 Sq Ft

  259 Bolton Rd, Winchester, NH 03470

  Stunning & modern unique True Timber Frame home has it all with incredible CT River views an easy commute to MA, VT or Keene. The property welcomes you with well-lit custom retaining walls, expansive perennial gardens, two-car garage, and barn on just under 2 acres. Enjoy outdoor life under the covered patio, relax on one of the many private decks or fire pits. Dual RV hook up with water disposal

  Don Goudreau EXP Realty

  259 Bolton Rd, Winchester, NH 03470
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  /60

  $795,000

  • 4 Beds
  • 2 Baths
  • 3,492 Sq Ft

  849 Route 10, Gilsum, NH 03448

  Quintessential New England charm meets endless possibility in this inviting farmhouse just beyond the picturesque village of Gilsum. Set on a gently sloping 3-acre lot with a peaceful stream along the northern edge, this property offers the perfect balance of privacy, space, and natural beauty.Inside, the 4-bedroom, 2-bath home is designed for both comfort and flexibility. A finished attic

  Bill Hutwelker SVN The Masiello Group- Keene

  849 Route 10, Gilsum, NH 03448
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  /59

  $725,000

  • 4 Beds
  • 2 Baths
  • 3,492 Sq Ft

  849 Route 10, Gilsum, NH 03448

  Quintessential New England charm meets endless possibility in this inviting farmhouse just beyond the picturesque village of Gilsum. Set on a gently sloping 3-acre lot with a peaceful stream along the northern edge, this property offers the perfect balance of privacy, space, and natural beauty.Inside, the 4-bedroom, 2-bath home is designed for both comfort and flexibility. A finished attic

  Bill Hutwelker SVN The Masiello Group- Keene

  849 Route 10, Gilsum, NH 03448
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  /47

  $450,000

  • 4 Beds
  • 4 Baths
  • 2,713 Sq Ft

  658 Main St, Marlborough, NH 03455

  Step into the timeless character of this 1875 New Englander farmhouse, where classic charm meets modern comfort. Just waiting for your imagination to make this gem shine again. Set on 5 full acres with established garden space and sweeping mountain views, this property offers the perfect blend of history, beauty, and New Hampshire living. Inside, you’ll find amazing wood flooring that carries the

  Bruce Murphy Keller Williams Realty Metro-Keene

  658 Main St, Marlborough, NH 03455
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  /54

  $475,000 Open Sat 10AM - 12PM

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

  24 Village Rd, Surry, NH 03431

  Exquisite, fully renovated residence in picturesque Surry Village, proudly held by the same family since its original construction. Thoughtful updates blend seamlessly with the home’s inherent character, creating an inviting and elevated living experience. The expansive, level grounds offer a dedicated garden area, detached garage, and an additional outbuilding ideal for a workshop, studio, or

  Ryan Goodell EXP Realty

  24 Village Rd, Surry, NH 03431
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  /28

  $1,250,000

  • 11,690 Sq Ft

  9 Merchant St, North Walpole, NH 03609

  Excellent 14-Unit Investment Opportunity – North Walpole, NH Discover a solid, income-producing property that checks all the boxes for both stability and future upside! These two side-by-side apartment buildings offer a total of 13 well-maintained units and a 14th unit to be finished. The owners have already completed updates in nearly every apartment, featuring modern kitchens, fresh paint, new

  Bert Inman RE/MAX Town & Country

  9 Merchant St, North Walpole, NH 03609
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  /51

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 1,736 Sq Ft

  178 North Rd, Alstead, NH 03602

  Brand new custom-built home in picturesque, quiet country location approximately 1 mile from Lake Warren in beautiful Alstead NH! Spacious 1st floor primary suite, lovely flow and open concept 1st floor with custom kitchen with stone countertops, open dining and living rooms. 1st floor laundry room and 1/2 bath off the breezeway. 2 bedrooms and another full bath on the 2nd floor provides plenty

  Ryan Goodell EXP Realty

  178 North Rd, Alstead, NH 03602
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  /52

  $695,000

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

  24 Red Gate Rd, Jaffrey, NH 03452

  Here is a charming 5 bedroom home, circa 1999, situated on a low trafficked dead end, town maintained road. There’s plenty of elbow room (3,872 sf), and it offers amenities galore such as the unobstructed view of Gap Mountain, well known for its hiking and blueberry picking. Very well built, it features solid wooden doors, a whole house generator, whole house fan, and handsome hardwood floors and

  Marc Tieger Tieger Realty Co. Inc.

  24 Red Gate Rd, Jaffrey, NH 03452
• 

  

  /47

  $518,900

  • 4 Beds
  • 2 Baths
  • 1,972 Sq Ft

  17 Leahy Rd, Keene, NH 03431

  Charming Move-In Ready 4-Bedroom 2-Bath Home with Year-Round Comfort! Welcome to this inviting and well-maintained 4-bedroom, 2 full bathroom home nestled in a lovely neighborhood! Conveniently located near schools, walking trails, and shopping, this property offers the perfect blend of comfort and accessibility. The heart of the home features a bright kitchen with Corian countertops, skylights,

  Jillian Exel BHG Masiello Keene

  17 Leahy Rd, Keene, NH 03431

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