Cheshire, NH Homes

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  /45

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 2,210 Sq Ft

  61 Orchard Rd, Chesterfield, NH 03443

  Continue the legacy of owning the oldest home in Chesterfield with its rich history, bucolic setting of woods, fields, pond and orchard. Well maintained features include beamed ceilings, wide pine floors, slate roof and center chimney. The Custom kitchen has stainless steel appliances, cherry cabinetry and CaesarStone counters. White oak flooring was installed with programmable radiant

  Timothy Keating BHG Masiello Keene

  61 Orchard Rd, Chesterfield, NH 03443
• 

  

  

  /16

  $6,700 per month

  • 4 Beds
  • 2.5 Baths
  • 4,823 Sq Ft
  • House for Rent

  18 Namaschaug Landing, Spofford, NH 03462

  A RENTAL LIKE NO OTHER!!! WELCOME TO THE LAKE! You're going to absolutely love this stunning “Lake Life Dream Home”. This executive level, meticulously maintained home overlooks gorgeous Spofford Lake, in Chesterfield, N.H. You’ll have over 100 ft. of incredible lakefront to enjoy all your favorite summer watersport activities, expansive deck, stone patio, lake front gazebo, dock, included. The

  Todd Bassler Greenwald Realty Group

  18 Namaschaug Landing, Spofford, NH 03462
• 

  

  

  /22

  $365,000 Sold Aug 01, 2025

  • 543 Sq Ft
  • $672/SF
  • 3 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1998

  263 Welcome Hill Rd, Chesterfield, NH 03466

  Nestled away from the hustle and bustle of city life, there lies a breathtaking piece of land, a sanctuary of natural beauty spanning 108 acres. This recreational haven features a charming, seasonal cabin that offers a nice mix of rustic charm for those seeking privacy. You'll be in awe as you walk in this 1 bedroom private get-a-way. And yes, it offers a full kitchen, 3/4 bath, living room, and

  Todd Bassler Greenwald Realty Group

  263 Welcome Hill Rd, Chesterfield, NH 03466
• 

  

  

  /20

  Est $597,028 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,704 Sq Ft

  193 Valley Park Dr, Spofford, NH 03462

  193 Valley Park Dr, Spofford, NH 03462
• 

  

  

  /49

  $925,000

  • 4 Beds
  • 2.5 Baths
  • 4,116 Sq Ft

  125 Stage Rd, West Chesterfield, NH 03466

  19+ acres of ultimate privacy surround this spectacular home with timeless details and stunning views, offering a perfect blend of comfort & sophistication. The contractor/owner exquisitely built and maintained the property and thought of everything, starting with the welcoming foyer adorned with Spanish marble. The chef’s kitchen features granite counters, a downdraft gas stove, mesquite

  Ben Prentice Keller Williams Realty Metro-Keene

  125 Stage Rd, West Chesterfield, NH 03466
• 

  

  /4

  $164,500 Sold Jul 14, 2025

  • Land
  • 108 Acres
  • $1,527 per Acre

  • 12 Days On Market

  0 Stones Mill Rd Unit 5045865, Chesterfield, NH 03443

  A surveyed 107.7-acre tract of land abutting the 13,000+acre Pisgah State Park is an ideal location for anyone looking to enjoy the outdoors whether for hunting, hiking or camping. Streams and a nearby pond offer wildlife viewing year-round. The serene setting offers a natural escape from the everyday hustle and bustle of the city as you reconnect with nature and everything it has to offer.

  Fred Blais Blais & Associates, Realtors

  0 Stones Mill Rd Unit 5045865, Chesterfield, NH 03443
• 

  

  /36

  Est $323,683 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,667 Sq Ft

  35 Pierce Rd, Chesterfield, NH 03462

  35 Pierce Rd, Chesterfield, NH 03462
• 

  

  /51

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,498 Sq Ft

  46 N Shore Rd, Chesterfield, NH 03462

  Ultimate Lakeside Living at Spofford Lake. Experience luxury and comfort in this meticulously renovated, turn-key home on the prestigious Spofford Lake. Professionally Designed for year-round enjoyment, every detail has been carefully considered so you can move in and start making memories from day one. Full interior and exterior painting delivers a modern, cohesive look. All floors have been

  Nancy Proctor BHG Masiello Keene

  46 N Shore Rd, Chesterfield, NH 03462
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  /45

  $401,000 Sold Jul 01, 2025

  • 4,981 Sq Ft
  • $81/SF
  • 5 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1839

  108 Westmoreland Rd, Spofford, NH 03462

  Nestled on 21 sprawling acres, this estate, formerly known as "The Maples- Bed & Breakfast" offers a unique blend of historical charm and modern luxury. This large property has a true New England feel and features multiple screened-in porches, perfect for enjoying the natural surroundings. The first floor is designed for seamless living, boasting a large open living room, primary bedroom suite, a

  Todd Bassler Greenwald Realty Group

  108 Westmoreland Rd, Spofford, NH 03462
• 

  

  /40

  Est $676,774 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,752 Sq Ft

  30 White Birch Dr, Chesterfield, NH 03443

  30 White Birch Dr, Chesterfield, NH 03443
• 

  

  /55

  $1,495,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,927 Sq Ft

  40 N Shore Rd, Spofford, NH 03462

  A rare opportunity to own an absolutely charming cottage on Spofford Lake. It checks so many of the boxes that buyers are looking for....private, lovely flat landscaped lot, with everything you need on the first floor. It has a large dining room with a brick fireplace, the large living room has a cathedral ceiling and glass wall over looking the lake. The kitchen has an eat-in island, double

  Tere Clarkson RE/MAX Town & Country

  40 N Shore Rd, Spofford, NH 03462
• 

  

  /28

  $514,500 Sold Jun 30, 2025

  • 2,676 Sq Ft
  • $192/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1888

  2 Streeter Hill Rd, West Chesterfield, NH 03466

  Located in West Chesterfield, this 1888 farmhouse is beautifully maintained and designed for modern comforts - it could be the perfect place to build your future! Settled on a hilltop corner, this property is ideally positioned between both Brattleboro, VT and Keene, NH in a peaceful country setting. The 1.6 acre lot offers a sprawling front yard with lush garden beds and a fully-enclosed private

  Megan Manley North New England Real Estate Group

  2 Streeter Hill Rd, West Chesterfield, NH 03466
• 

  

  /40

  Est $605,625 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,928 Sq Ft

  25 Pine Tree Cir, Spofford, NH 03462

  25 Pine Tree Cir, Spofford, NH 03462
• 

  

  /57

  $1,150,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,290 Sq Ft

  53 Lorenz Rd, West Chesterfield, NH 03466

  Welcome to your private sanctuary nestled on 37.74 acres of beautifully landscaped grounds in one of the most desirable locations in West Chesterfield. Farmhouse style Colonial built in 1990 with breathtaking views of Vermont, rolling fields, and a serene pond perfect for fishing or quiet reflection, this extraordinary property offers the ideal balance of luxury, space, and tranquility. The

  Josh Greenwald Greenwald Realty Group

  53 Lorenz Rd, West Chesterfield, NH 03466
• 

  

  /60

  $610,470 Sold Jun 24, 2025

  • 3,282 Sq Ft
  • $186/SF
  • 0 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1995

  36 Split Oak Cir, Chesterfield, NH 03443

  Welcome to your dream log home, where rustic charm meets modern luxury! Nestled on a picturesque 1.34-acre lot, this stunning Crockett Log home promises to be your ultimate escape. From the moment you step inside, the soaring cathedral ceilings and open-concept living space will take your breath away. Whether you're hosting dinner or preparing a quiet meal, the kitchen’s elegant granite

  Josh Greenwald Greenwald Realty Group

  36 Split Oak Cir, Chesterfield, NH 03443
• 

  

  /29

  Est $291,606 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft

  1739 Route 9, Spofford, NH 03462

  1739 Route 9, Spofford, NH 03462
• 

  

  /60

  $634,500

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft

  23 Bittersweet Ln, Chesterfield, NH 03466

  Escape the day to day at this picturesque waterfront Cape! Down your private publicly-maintained deadend road, beside the hillside and quaint horse fence, awaits majestic views to envelop you at this park-like setting on the Connecticut River. Your private 3-acre property has over 500’ of riverfront and views with your own beach area and naturally-formed rock jetty. While you’re near to many

  Mary M. Belle Isle EXP Realty

  23 Bittersweet Ln, Chesterfield, NH 03466
• 

  

  /55

  $400,000 Sold Jun 20, 2025

  • 1,837 Sq Ft
  • $218/SF
  • 63 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1974

  121 Pond Brook Rd Unit 4-A001, West Chesterfield, NH 03466

  Versatile cape, on a beautiful 6 acre lot w/a greenhouse & south facing 3 season sunroom. Very special land, tended for over 40 years, now filled w/herb gardens, garden beds, blueberry patch & fruit trees. Custom built stone walkways & walls compliment the peaceful setting. New windows & natural woodwork. Livingroom w/hardwood flooring, chair rail, picture window & mini-split. KIT & Dining area

  Connie Joyce RE/MAX Town & Country

  121 Pond Brook Rd Unit 4-A001, West Chesterfield, NH 03466
• 

  

  /23

  Est $329,125 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,414 Sq Ft

  1596 Route 9, Spofford, NH 03462

  1596 Route 9, Spofford, NH 03462
• 

  

  /3

  $150,000

  • Land
  • 3.86 Acres
  • $38,860 per Acre

  00 Orchard Rd, Chesterfield, NH 03443

  A rare find in Chesterfield. 4+/- acres of mostly open land situated on a quiet country road. Long road frontage assures privacy and allows for your choice of driveway access. Located about 3 miles from Rt 9 and close to Chesterfield Elementary, this spot provides convenience to Keene, Brattleboro and Hinsdale. And is close to Spofford Lake and Pisgah Park.

  Timothy Keating BHG Masiello Keene

  00 Orchard Rd, Chesterfield, NH 03443
• 

  

  /55

  $427,000 Sold May 30, 2025

  • 4,140 Sq Ft
  • $103/SF
  • 6 Days On Market

  • 8 Beds
  • 4 Baths
  • Built 1850

  73 Main St, Chesterfield, NH 03466

  Step into a rare opportunity to own a piece of Chesterfield's rich history. Located in the heart of town, this beautifully preserved building sits directly on the scenic Catsbane Brook, offering tranquil water views, a peaceful back yard and a large deck. With its generous layout, high ceilings, and large windows that fill the space with natural light, this one-of-a-kind building is perfect for

  Kelsey Malloy Keller Williams Realty Metro-Keene

  73 Main St, Chesterfield, NH 03466
• 

  

  /23

  Est $262,135 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft

  395 Pond Brook Rd, West Chesterfield, NH 03466

  395 Pond Brook Rd, West Chesterfield, NH 03466
• 

  

  /32

  $374,900

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

  995 Route 9, West Chesterfield, NH 03466

  Tucked away on 5 serene acres, this charming 2-bedroom, 1.5-bath ranch offers a perfect blend of privacy and convenience. Enjoy seamless access to both Brattleboro and Keene while coming home to your own peaceful retreat. The renovated kitchen and full bath bring modern style and comfort, complemented by a spacious full basement for storage or expansion potential. Step outside to a large private

  Cynthia Westover Galloway Real Estate LLC

  995 Route 9, West Chesterfield, NH 03466
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  /38

  $420,000 Sold May 23, 2025

  • 1,908 Sq Ft
  • $220/SF
  • 37 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1973

  129 Farr Rd, West Chesterfield, NH 03466

  Welcome to 129 Farr Road, Chesterfield, NH!Country setting with 2 well landscaped and usable acres in a highly desirable neighborhood. Offering 1,912 sq ft of living space, this home blends charm and country character.Step inside to find hardwood floors and a nicely done kitchen featuring soapstone countertops, a spacious butcher block island. The cozy living room highlighted by a wood stove on a

  Shane Lampinen Broadvest Real Estate Group

  129 Farr Rd, West Chesterfield, NH 03466
• 

  

  /39

  Est $425,438 Not Listed For Sale

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

  11 High St, Chesterfield, NH 03462

  11 High St, Chesterfield, NH 03462
• 

  

  /12

  $300,000

  • Land
  • 0.68 Acre
  • $441,176 per Acre

  36 Canal St, Spofford, NH 03462

  Build Your Dream Retreat in the Heart of the Spofford Lake District! Welcome to 36 Canal Street, a picturesque and buildable 0.68-acre lot with existing well, perched above the scenic Partridge Brook, fed by Spofford Lake. This rare offering is tucked into one of the region’s most sought-after lake communities—just minutes from the town beach, boat launch, and all the recreational fun

  Kelsey Malloy Keller Williams Realty Metro-Keene

  36 Canal St, Spofford, NH 03462
• 

  

  /46

  $453,500 Sold May 02, 2025

  • 2,256 Sq Ft
  • $201/SF
  • 37 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1980

  93 Pinnacle Springs Rd, Chesterfield, NH 03443

  Located between Keene and Brattleboro in a developed neighborhood tucked in off the road is this three bedroom home. Direct entry from the two car garage into the laundry and entry area. The open kitchen and eating area have views of the back yard with a sliding door to the back deck for grilling. The front entry has great storage and leads you to the dining room, step down living room, half bath

  Sandy Cormier Greenwald Realty Group

  93 Pinnacle Springs Rd, Chesterfield, NH 03443
• 

  

  /26

  Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,278 Sq Ft

  52 Church St, Chesterfield, NH 03462

  52 Church St, Chesterfield, NH 03462
• 

  

  /53

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 2,157 Sq Ft

  132 Poocham Rd, West Chesterfield, NH 03466

  Wonderful log home in low tax, and very convenient, Chesterfield! Set in a private and pretty country setting on over 5 acres, this lovely home is just minutes from either Keene or Brattleboro. Walk onto the very well built front porch you get a sense of what awaits you inside. Step inside into the cathedral ceiling great room you will immediately feel at home. Open concept, wood floors, a large

  Bert Inman RE/MAX Town & Country

  132 Poocham Rd, West Chesterfield, NH 03466
• 

  

  /57

  $580,000 Sold Apr 22, 2025

  • 2,016 Sq Ft
  • $288/SF
  • 100 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  18 Meadowview Rd, West Chesterfield, NH 03466

  PRICE REDUCTION. Conveniently located between Keene and Brattleboro in an established cul-de-sac neighborhood, great for walking your pet, running and biking. The open, level yard around the house is about 3 acres with an additional 5 wooded acres that sits below grade off the back yard. Four bedroom colonial home has a covered front porch and sits back off the road. The home has hardwood and

  Sandy Cormier Greenwald Realty Group

  18 Meadowview Rd, West Chesterfield, NH 03466
• 

  

  /32

  Est $517,307 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,368 Sq Ft

  253 Pond Brook Rd, West Chesterfield, NH 03466

  253 Pond Brook Rd, West Chesterfield, NH 03466
• 

  

  /13

  $330,000

  • Land
  • 2.01 Acres
  • $164,179 per Acre

  0 Stow Dr Unit 12-A001-021 2.33 Ac, Chesterfield, NH 03466

  Great level commercial lot with easy access to Route 9 close to Brattleboro and Keene. Many options for its use.

  Sandy Cormier Greenwald Realty Group

  0 Stow Dr Unit 12-A001-021 2.33 Ac, Chesterfield, NH 03466
• 

  

  /26

  $335,000 Sold Apr 10, 2025

  • 1,512 Sq Ft
  • $222/SF
  • 12 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1999

  16 Morts Rd, Chesterfield, NH 03466

  Perfect location! Nestled between Brattleboro and Keene with easy access to Mass, this sweet, modern cape is just perfect for your new lifestyle. Enjoy the beautiful lawn with stone wall accents providing landscape artistry and lots of plantings! A surprise feature is your own pond, filled with wildlife including a heron, duck families and birds galore... attracted by the open water surrounded

  Christine Lewis Brattleboro Area Realty

  16 Morts Rd, Chesterfield, NH 03466
• 

  

  /25

  Est $490,531 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,345 Sq Ft

  21 Cobleigh Estates Rd, West Chesterfield, NH 03466

  21 Cobleigh Estates Rd, West Chesterfield, NH 03466
• 

  

  /45

  $400,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,027 Sq Ft

  247 N Shore Rd, Spofford, NH 03462

  Two bedroom cottage with shared lake access set off the road with a great floor plan. The front windows wrap around the sides to provide great natural lignt and fresh air. You are welcomed with an open deck, covered entry and deck for extended living. The kitchen has a portable island, great storage and counter space that is open to the living area. The dining area has a passthrough from the

  Sandy Cormier Greenwald Realty Group

  247 N Shore Rd, Spofford, NH 03462
• 

  

  /27

  $278,000 Sold Apr 02, 2025

  • 846 Sq Ft
  • $329/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1983

  1720B Route 9, Spofford, NH 03462

  Charming and Affordable Living - Ready for Immediate Occupancy!This delightful 2-bedroom, 1-bathroom home is the perfect blend of comfort and convenience. Featuring beautiful hardwood floors in the bedrooms and tile flooring in the bathroom, this cozy property is move-in ready. The home also boasts a spacious walk-out basement, offering plenty of storage or additional potential for

  Patricia Paquette BHG Masiello Keene

  1720B Route 9, Spofford, NH 03462
• 

  

  /38

  Est $793,129 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  187 N Shore Rd, Spofford, NH 03462

  187 N Shore Rd, Spofford, NH 03462
• 

  

  /43

  $350,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,359 Sq Ft

  663 Gulf Rd, West Chesterfield, NH 03466

  Welcome to 663 Gulf Road — Where Nature, Privacy, and Convenience Come Together. Tucked away on one of West Chesterfield’s most scenic dirt roads, 663 Gulf Road offers a rare blend of privacy, natural beauty, and accessibility. Surrounded by peaceful woods and just steps from year-round waterfalls and walking trails, this property invites you to slow down and enjoy the outdoors every day. Just

  Kelsey Malloy Keller Williams Realty Metro-Keene

  663 Gulf Rd, West Chesterfield, NH 03466
• 

  

  /52

  $409,000 Sold Feb 28, 2025

  • 1,735 Sq Ft
  • $236/SF
  • 6 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  69 Forestview Dr, Spofford, NH 03462

  OFFER DEADLINE TUES 1/28 @ 10AM. Tucked away among the trees on just over 2 acres in sought-after Chesterfield Heights, this unique contemporary 2-bedroom home offers privacy and charm. The property features a new deck, a fenced-in backyard, and an attached 1-car garage. Inside, hardwood floors flow throughout, and large windows invite an abundance of natural light. A cozy woodstove adds warmth

  Rochelle Bunton Greenwald Realty Group

  69 Forestview Dr, Spofford, NH 03462
• 

  

  /20

  Est $466,290 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,828 Sq Ft

  101 Crowningshield Rd, Chesterfield, NH 03443

  101 Crowningshield Rd, Chesterfield, NH 03443

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