Cheshire, NH Homes

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  /25

  $389,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  37 Town Beach Rd, Winchester, NH 03470

  Experience year-round lakefront living in this charming five-room, two-bedroom, one-bath bungalow on the serene shores of Forest Lake. With 49 feet of waterfront, a private sandy beach, and a dock, this retreat is perfect for relaxing or entertaining.Enjoy stunning southeast views of the 85-acre lake from one of two spacious decks. Inside, the first floor features a well-appointed kitchen

  

  Laurie Mack

  BHG Masiello Keene

  (603) 865-1035

  37 Town Beach Rd, Winchester, NH 03470
• 

  

  

  /22

  $2,500 per month

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Townhouse for Rent

  2 Ashuelot Main St, Winchester, NH 03441

  This renovated and furnished 18th century farmhouse exudes charm. Built in 1769, The Ashuelot River Bridge House abuts the NH Covered Bridge #1, has great views and 1,000+ feet of river frontage. There are three bedrooms, one queen, one full, and one with two twin beds. The house has beautifully refinished wood floors. The walls are original - refinished horsehair plaster. In keeping with a

  2 Ashuelot Main St, Winchester, NH 03441
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  /43

  $218,500 Sold Aug 01, 2025

  • 3,603 Sq Ft
  • $61/SF
  • 101 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1860

  102 Keene Rd, Winchester, NH 03470

  Opportunity Awaits at the Historic Publik House – Live, Work, and Create!Are you searching for a unique property with endless potential? This charming 3-bedroom, 1-bath Victorian Cape offers a rare opportunity to combine residential living with business possibilities. Situated along well-traveled Route 10 in Winchester and nestled against a peaceful river backdrop, this versatile property

  Denise Thomas BHG Masiello Keene

  102 Keene Rd, Winchester, NH 03470
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  /27

  Not Listed For Sale

  • 3 Beds
  • 946 Sq Ft

  217 Warwick Rd, Winchester, NH 03470

  217 Warwick Rd, Winchester, NH 03470
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  /18

  $174,700

  • 3 Beds
  • 1 Bath
  • 789 Sq Ft

  142 Back Ashuelot Rd, Winchester, NH 03470

  142 Back Ashuelot Road is a modest yet well-maintained manufactured home on a spacious, slightly elevated lot situated in the rural portion of Winchester, near the Ashuelot village area. Winchester offers access to outdoor recreation, including Pisgah State Park—the state's largest at ~13,300 acres—great for hiking, biking, and water activities. The property is surrounded by beautiful mature

  

  Laurie Mack

  BHG Masiello Keene

  (888) 519-3078

  142 Back Ashuelot Rd, Winchester, NH 03470
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  /10

  $1,490 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  66 Richmond Rd Unit A, Winchester, NH 03470

  1 bedroom apartment with flex room. Newly updated. Large living room. Convenient to town and amenities. Available immediately. Must have proof of prior rental history being current as well as proof of income. Rental application required. First and security due at signing of lease.

  Emily Lagerberg R.H. Thackston & Company

  66 Richmond Rd Unit A, Winchester, NH 03470
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  /11

  $55,000 Sold Jul 31, 2025

  • Land
  • 2.64 Acres
  • $20,833 per Acre

  • 91 Days On Market

  0 Old Swanzey Rd, Winchester, NH 03470

  Come build your new home!!!! 2.64 acres awaits you!!! Country setting, rural area, yet minutes from town!! Perc tested.

  Emily Lagerberg R.H. Thackston & Company

  0 Old Swanzey Rd, Winchester, NH 03470
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  /14

  Est $217,891 Not Listed For Sale

  • Studio
  • 2 Baths
  • 2,000 Sq Ft

  9 Mechanic St, Winchester, NH 03470

  9 Mechanic St, Winchester, NH 03470
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  /24

  $435,000

  • 1 Bed
  • 1 Bath
  • 756 Sq Ft

  25 Headlands Rd, Winchester, NH 03470

  Wonderful Waterfront Cottage! Situated on pristine Forest Lake, this charming and renovated 1 BR + Loft home is a perfect get-away spot for summer enjoyment. As a year-round home, winter activities such as x-country skiing, snowmobiling and ice fishing can be enjoyed. Modern appliances, mini split heating and cooling, laminated hardwood flooring and a renovated bath enhance this property. The

  Vincent Dolan RE/MAX Town & Country

  25 Headlands Rd, Winchester, NH 03470
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  /12

  $1,295 per month

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

  9 Elm St Unit C, Winchester, NH 03470

  $1295 per month includes Heat & Hotwater tenant pays own electric. 2 room Efficency Eat-In Kitchen 3/4 bath. Off street parking

  Dick Thackston R.H. Thackston & Company

  9 Elm St Unit C, Winchester, NH 03470
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  /45

  $700,000 Sold Jul 25, 2025

  • 4,316 Sq Ft
  • $162/SF
  • 58 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1985

  168 Bolton Rd, Winchester, NH 03470

  Privacy galore with home positioned well and surrounded by 40+ acres! Potential horse property with one outbuilding could hold a couple horses. This 1985 unique build was an absolute labor of love. Painstaking detail was taken over the 3 year build of a gorgeous Gambrel home. A 2 bedroom apartment is rented out above the garage for added income. The listing is comprised of 3 adjacent lots all

  Don Goudreau EXP Realty

  168 Bolton Rd, Winchester, NH 03470
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  /5

  Not Listed For Sale

  159 Ashuelot Main St, Ashuelot, NH 03441

  159 Ashuelot Main St, Ashuelot, NH 03441
• 

  

  /9

  $395,900 New Construction

  • 3 Beds
  • 2 Baths
  • 3,536 Sq Ft

  143 Richmond Rd, Winchester, NH 03470

  New 1768 Square feet Home Featuring 3 bedrooms with 2 full baths close to schools and down town. This newly constructed features a full walkout basement with a 12'x'16 deck on the back. Kitchen Features Black Stainless appliances with white Shaker style cabinets and Granite counter tops. First floor laundry as you enter the mudroom with large living room. Home features Propane hot water and heat

  Ralph Harvey Listwithfreedom.com

  143 Richmond Rd, Winchester, NH 03470
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  /14

  $144,900 Sold Jul 18, 2025

  • 1,188 Sq Ft
  • $122/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  49 Kapper Dr, Winchester, NH 03470

  Just compare before you buy ! She is ready to move into now ! Vacant can close anytime. A great country lot with private yard. The lot to the right is vacant for even more privacy. All new appliances, bathrooms, flooring, faucets, sinks, kitchen cabinets and sinks . The fireplace and the glass sliding door leading out to a great deck over viewing a tree line just adds to the beauty. Don't

  Donald Gingras Donald Gingras Realty Co

  49 Kapper Dr, Winchester, NH 03470
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  /14

  Est $270,000 Not Listed For Sale

  • Studio
  • 4,525 Sq Ft

  77 Richmond Rd, Winchester, NH 03470

  77 Richmond Rd, Winchester, NH 03470
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  /41

  $439,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft

  72 Watson Rd, Winchester, NH 03470

  Back on the market due to buyer financing! Your chance to own 14+ private acres in beautiful Winchester, NH! Tucked away in a peaceful natural setting, this stunning home offers the perfect blend of rustic charm and modern comfort. You'll enjoy ultimate seclusion with a seasonal brook, walking trails, and an abundance of natural beauty just outside your door. Inside, the open-concept first floor

  Kristin Reyes REAL Broker NH, LLC

  72 Watson Rd, Winchester, NH 03470
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  /57

  $264,900 Sold Jun 13, 2025

  • 1,512 Sq Ft
  • $175/SF
  • 3 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2003

  84 Warwick Rd, Winchester, NH 03470

  Spacious 4 bedroom, 2 bath, double wide modular home on 4.8 acres of level land. Master Bathroom soaking tub, vaulted ceilings, a great room. Numerous outbuildings and chicken coops. Come see!

  Thomas Travers Great Beginnings Real Estate Services, LLC

  84 Warwick Rd, Winchester, NH 03470
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  /6

  Not Listed For Sale

  0 Old Westport Rd, Winchester, NH 03470

  0 Old Westport Rd, Winchester, NH 03470
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  /15

  $499,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,470 Sq Ft

  63 Prospect Hill Rd, Richmond, NH 03470

  This private enclave is an opportunity for investors or for family and friends looking for property for a family compound. It could also have hook ups for seasonal RV use. All of the dwellings and 38+/_ acres are in Richmond and 23.5 acres are in Fitzwilliam, across private, Prospect Hill Road. the main cabin, has been recently renovted. One single wide manufactured home is in very good

  Heather Peterson Four Seasons Sotheby's International Realty

  63 Prospect Hill Rd, Richmond, NH 03470
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  /16

  $73,500 Sold Jun 10, 2025

  • 924 Sq Ft
  • $80/SF
  • 27 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  14 Redwood Dr, Winchester, NH 03470

  Low maintenance, one level living!!!! Well maintained 3 bedroom, 2 bathroom manufactured home in a co-op. Open concept eat in kitchen and living space, tons of cabinets and a breakfast bar!! Master bedroom with spacious closet and private bathroom on one end and 2 additional bedrooms and full bathroom on the other. Fenced in yard and an 8x10 metal shed.

  Dick Thackston R.H. Thackston & Company

  14 Redwood Dr, Winchester, NH 03470
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  /35

  Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft

  99 Keene Rd, Winchester, NH 03470

  99 Keene Rd, Winchester, NH 03470
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  /33

  $599,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,946 Sq Ft

  679 Warwick Rd, Winchester, NH 03470

  Once-in-a-Lifetime Opportunity – 137 Acres of New England Charm in Winchester, NH & Warwick, MADiscover a rare gem with this extraordinary 137-acre property straddling the picturesque towns of Winchester, NH and Warwick, MA. A harmonious blend of open fields, rolling pastures, and mature woods framed by classic stone walls, this property offers a peaceful pond, meandering stream, and endless

  Nancy Proctor BHG Masiello Keene

  679 Warwick Rd, Winchester, NH 03470
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  /20

  $90,000 Sold Jun 09, 2025

  • 1,454 Sq Ft
  • $62/SF
  • 30 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1979

  22 Jones Rd, Winchester, NH 03470

  Off the beaten path in a country setting is where you will find this home on just over 2 acres!!! Keep the mobile home that is there or build a new home if you wish. Town water and sewer. Possibilities are endless!

  Dick Thackston R.H. Thackston & Company

  22 Jones Rd, Winchester, NH 03470
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  /24

  Not Listed For Sale

  • Studio
  • 2,838 Sq Ft

  51 Mechanic St, Winchester, NH 03470

  51 Mechanic St, Winchester, NH 03470
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  /50

  $425,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,748 Sq Ft

  110 Bolton Rd, Winchester, NH 03470

  This Cedar-clad 1977 Gambrel home was thoughtfully placed on a quiet, wooded lot on the outskirts of Winchester, NH. A brook brings the sounds and sight of fresh water passing through your back yard year-round, providing a peaceful natural setting for this well-kept home. The 7.3 acres provides lots of privacy from neighbors and room to expand. Step into the foyer to kick off your shoes and hang

  Greg Carter Four Seasons Sotheby's International Realty

  110 Bolton Rd, Winchester, NH 03470
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  /26

  $235,000 Sold May 22, 2025

  • 864 Sq Ft
  • $272/SF
  • 25 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1961

  17 Woodard Ave, Winchester, NH 03470

  Looking for a managable size ranch, take a look at this sweet 2 bedroom, 1 bath home in Winchester, NH. Minutes from the Keene, NH, MA border and I91!Hardwood floors through out with tile in kitchen and updated bathroom. Nice sized bedrooms with lots of light. Kitchen is updated while still charming.Large front living room makes for a comfortable space to relax in.Large lot 1.3 acres all level

  Robin Sanctuary Traditions Real Estate LLC

  17 Woodard Ave, Winchester, NH 03470
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  /14

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,409 Sq Ft

  19 Chapel St, Winchester, NH 03470

  19 Chapel St, Winchester, NH 03470
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  /32

  $549,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,930 Sq Ft

  510 Old Westport Rd, Winchester, NH 03470

  MOTIVATED SELLERS!!!!!Welcome to this brand-new construction in the charming town of Winchester, NH! Located just minutes from interstates, shopping, and healthcare, this 3-bedroom, 2-bathroom home offers both convenience and tranquility. Picture yourself enjoying the scenic drive over the historic Old Coombs covered bridge each day, with picturesque views of the Ashuelot River. This

  Kirsten Perkins BHG Masiello Keene

  510 Old Westport Rd, Winchester, NH 03470
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  /18

  $263,000 Sold May 20, 2025

  • 1,405 Sq Ft
  • $187/SF
  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1896

  31 Hildreth St, Winchester, NH 03470

  Convenient to downtown but situated on a quiet dead end street. No traffic going past. Needs some TLC and already has a new roof. This home has a nice flow whether entering from the enclosed side porch or through the attractive front door. The porch opens onto a large rear deck giving the feeling of isolation while enjoying the water view. The yard is spacious and perfect for children to play and

  Elaine Hall BHG Masiello Keene

  31 Hildreth St, Winchester, NH 03470
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  /40

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,484 Sq Ft

  23 Ashuelot St, Winchester, NH 03470

  23 Ashuelot St, Winchester, NH 03470
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  /57

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,526 Sq Ft

  12 Miner Ct, Winchester, NH 03470

  Welcome Home!!! Spacious New Englander within close proximity to town and amenities. This 3 bedroom home sits on just under half an acre and awaits you! Updates throughout! New paint, flooring, kitchen cabinets and countertop, newer heating system and water heater, metal roof, vinyl siding and town water. Come move into this home and make it your own!

  Dick Thackston R.H. Thackston & Company

  12 Miner Ct, Winchester, NH 03470
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  /3

  $129,900 Sold May 16, 2025

  • Land
  • 24 Acres
  • $5,481 per Acre

  • 67 Days On Market

  00 Bolton Rd, Winchester, NH 03470

  Discover the perfect blend of privacy and opportunity with this expansive 23.7-acre parcel nestled in the charming town of Winchester, NH. This beautifully wooded property offers a serene setting, surrounded by nature, yet conveniently located near town amenities and major roadways.Key Features:? 23.7 acres of pristine land with mature trees and natural beauty? Potential for subdivision – explore

  Zack LeRoy BHG Masiello Keene

  00 Bolton Rd, Winchester, NH 03470
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  /39

  Not Listed For Sale

  • 6 Beds
  • 2 Baths
  • 3,300 Sq Ft

  27 Ashuelot St, Winchester, NH 03470

  27 Ashuelot St, Winchester, NH 03470
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  /16

  $189,900

  • Land
  • 18 Acres
  • $10,550 per Acre

  0 Old Hinsdale Rd, Winchester, NH 03470

  Located at the very end of the town maintained road is where you will findthis private 18 acre lot building lot. This lot has been selectively cut opening up many nice walking trails including a cleared building site. Town must approve driveway permit to issue building permit as well as improving a portion of the class VI road where driveway would lead to building site. Electricity is at

  Jerry Chandler R.H. Thackston & Company

  0 Old Hinsdale Rd, Winchester, NH 03470
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  /3

  $29,900 Sold May 09, 2025

  • Land
  • 1.42 Acres
  • $21,056 per Acre

  • 85 Days On Market

  0 Old Spofford Rd, Winchester, NH 03470

  Located on a country road. Close to Pisgah State Park, Rail trail and the Ashuelot River. Approximately 3 miles to downtown Winchester, a quick drive to I91, and less than 30 minutes to Keene. Sub-divided, surveyed and perc test completed. Neighboring lot available for sale.

  Anna Schierioth HKS Associates, Inc.

  0 Old Spofford Rd, Winchester, NH 03470
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  /22

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,414 Sq Ft

  19 Ashuelot Main St, Ashuelot, NH 03441

  19 Ashuelot Main St, Ashuelot, NH 03441
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  /60

  $375,000

  • 3 Beds
  • 3.5 Baths
  • 2,688 Sq Ft

  153 Back Ashuelot Rd, Winchester, NH 03470

  Welcome Home—an incredible opportunity to bring your vision to life in the heart of charming Winchester, NH. This antique farmhouse has been thoughtfully framed, plumbed for 3 1/2 bath, offering a blank canvas for your dream home. Whether you're an investor, builder, or homeowner looking for a custom project, the groundwork is already laid for you to create something truly special.Outside of

  Aimpoint Realty Group Keller Williams Realty-Metropolitan

  153 Back Ashuelot Rd, Winchester, NH 03470
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  /12

  $340,000 Sold May 02, 2025

  • 820 Sq Ft
  • $415/SF
  • 118 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  372 Forest Lake Rd, Winchester, NH 03470

  Vacation, Staycation, Investment Opportunity? Discover this charming and beautifully renovated 2 Bedroom, Cape-style cottage in the Forest Lake District of Winchester. Improvements include hardwood flooring, butcher block countertops and updated appliances. The partially finished, walk-out basement has laundry hook-ups. Adjacent to the residence is a shed converted into an office/studio space

  Vincent Dolan RE/MAX Town & Country

  372 Forest Lake Rd, Winchester, NH 03470
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  /28

  Not Listed For Sale

  • 9 Beds
  • 4 Baths
  • 6,802 Sq Ft

  292 Richmond Rd, Winchester, NH 03470

  292 Richmond Rd, Winchester, NH 03470
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  /60

  $5,200,000

  • 4 Beds
  • 5.5 Baths
  • 5,120 Sq Ft

  398 Scofield Mountain Rd, Winchester, NH 03470

  One of New England's most unique & premiere properties, a sprawling sanctuary set on over 140 acres with sweeping views of Vermont, Massachusetts, & New York, it offers the ultimate escape from everyday life. A harmonious architectural masterpiece, calibrated with meticulous care. The home is crafted using an alternative construction method from 15 retrofit steel shipping containers reinforced by

  Susanna Corriveau Coldwell Banker Realty Bedford NH

  398 Scofield Mountain Rd, Winchester, NH 03470

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