Winchester, New Hampshire

One of Cheshire County's southern border towns, Winchester, New Hampshire, is a blue-collar community of just under 4500 residents.  Located in the southwestern corner of the Granite State, Winchester has a strong commercial and industrial presence lending to a relatively low unemployment rate in town.  Families that call Winchester “home” enjoy the natural beauty and quiet country air that this part of the state is so well known for, while visitors absorb the sights and sounds within the rolling hills of the breathtaking mountainous Monadnock Region.

The area to become Winchester was first granted to Colonel Josiah Willard, a military leader who desired a large plot of land on the eastern banks of the Connecticut River.  This was granted to him by the Colonial Massachusetts Government who, at the time, had full control of New Hampshire.  Known by locals as The Arlington Plantation, the settlement was incorporated as a nameless town in 1739.  For unknown reasons, some folks started calling it Winchester, so Willard petitioned the recently-formed New Hampshire government to incorporate the town as such in 1750, but failed.  His second attempt, in 1753, was a success and the town has been known as Winchester ever since.  It is possible that the name of Winchester comes from Charles Paulet, Marquis of Winchester, but as yet cannot be verified.

Winchester has enough small stores in town to meet most of the community’s needs, but if there’s something you need and Winchester doesn’t have it, Keene is just a ten-minute drive north, or Brattleboro, Vermont, is the same distance northwest.  However, since New Hampshire is a sales tax-free state, most Winchester residents prefer to shop within the state’s confines.  Finding things to do in Winchester is easy – the Pisgah Wilderness State Park is a stone’s throw from your front door and offers hiking, wilderness tours, mountain biking, fishing and snowmobiling during those cold winter months.  For other winter activities, you don’t need to travel far at all.  There are several ski resorts within twenty-five miles of Winchester as well as sledding hills that stretch for what seems like miles.  Summertime brings with it more fishing, boating, swimming, and pitching tents at the many campgrounds that dot the landscape of southwestern New Hampshire.  It’s all about the outdoors in this great state.

Winchester is a part of SAU #38.  The Winchester School educates resident children from kindergarten through the eighth grade.  High school age children in Winchester attend the Keene High School, in nearby Keene, NH.  There are no current plans to construct a high school in Winchester.

If you’re looking to buy a home in rural New Hampshire, look no further than Winchester.  Great location and great people are but two of the reasons you should consider purchasing your new home in Winchester.  If the southwestern part of the state isn’t what you’re looking for, perhaps you’d be interested in something closer to the seacoast or nearer to the White Mountains?  Wherever you’re considering, the first step in bringing your plans to fruition is to call Jim Miller Bean Group at (603) 801-3987.  Jim is here for you and you alone, from answering your NH questions to finding you the perfect home.  Call right now and find out just how quickly the dream can become reality.

Winchester School (k-8)
603-239-4721

Keene High School (9-12)
(603) 352-0640

Current Winchester New Hampshire Real Estate MLS Listings for Single Family Homes

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $500,000 - $600,000
31 Properties Found. Page 1 of 2

This Distinctive Country Estate Is Located In S...

REDUCED 5% Photo of Listing #4752974

$549,900 Active

  • 3 Beds
  • 3 Baths
  • 115.4 Acres
  • 4,191 ft²

Residential

435 Scofield Mountain Rd, Winchester, New Hampshire

MLS® #4752974

This Distinctive Country Estate Is Located In Southwestern Nh In A Magnificent Private Setting. Situated On Over 115 Acres On A Hillside With Well Appointed Outdoor Gathering Places. Start The Day Off Right In The Comfort Of Your Own Spa, A 12x35 Separate R...

An Exciting Property In An Exquisite Setting Of...

Photo of Listing #4779402

$399,000 Active

  • 3 Beds
  • 2 Baths
  • 0.82 Acres
  • 1,541 ft²

Residential

93 Lake Shore Dr, Winchester, New Hampshire

MLS® #4779402

An Exciting Property In An Exquisite Setting Offering The Best In Lakeside Living With An End Of Road Private Location And 100 Feet Of Waterfront. The Home Is Sited Perfectly To Take In Lake Views From The Main Living Areas As Well As The Master Bedroom. Th...

For Sale And/or Lease Easily Accessible To Mas...

Photo of Listing #4744408

$375,000 Active

  • 5 Acres

Commercial

20 Snow Rd, Winchester, New Hampshire

MLS® #4744408

For Sale And/or Lease Easily Accessible To Massachusetts And Vermont Via Nh Routes 10, 78 And 119. Zoned Commercial/industrial. Several Buildings Suitable For Storage, Manufacturing, Distribution, Automotive Repair, Automotive Dealership 14,500 Sq Ft...

Build A Life You Never Have To Take A Vacation ...

Photo of Listing #4773852

$339,000 Active

  • 3 Beds
  • 2 Baths
  • 0.14 Acres
  • 2,168 ft²

Residential

23 Headlands Rd, Winchester, New Hampshire

MLS® #4773852

Build A Life You Never Have To Take A Vacation From! Beautiful Lake House Warm And Inviting. Plenty Of Room To Invite Family And Friends, Enjoy The Lake Activities, Or Curl Up With A Book In Your Expansive Master Suite And Enjoy Your View! You Decide.

Great Development Potential With Approximately ...

Photo of Listing #4728780

$336,000 Active

  • 224 Acres

Land

Old Spofford Rd, Winchester, New Hampshire

MLS® #4728780

Great Development Potential With Approximately 1,985 Feet Of Road Frontage, 200' Required For Building Lot. Potential Views With Selective Cutting. Part Of Property Is Located Across From Pisgah Park.

Located Between Keene And Roads Leading To Rte....

REDUCED 3% Photo of Listing #4748238

$319,000 Active

  • 3 Beds
  • 2 Baths
  • 11.01 Acres
  • 1,400 ft²

Residential

967 Keene Rd, Winchester, New Hampshire

MLS® #4748238

Located Between Keene And Roads Leading To Rte. 91 Via Northfield, Ma. This '48 X 58'.. Almost 3000 Sqft. ..armstrong Steel Building On An Alaskan Slab Comes With Its Own Carefully And Comfortably Renovated Three Level Home. If The Steel Building Fulfills...

Wake Up On The Water! Rare Opportunity For Wate...

Photo of Listing #4750739

$318,500 Active

  • 3 Beds
  • 3 Baths
  • 0.19 Acres
  • 1,664 ft²

Residential

11 Hemlock Ave, Winchester, New Hampshire

MLS® #4750739

Wake Up On The Water! Rare Opportunity For Waterfront Property On The Crystal Clear Waters Of Forest Lake. New Construction To Replace Old Camp In Need Of Tearing Down. Reward Yourself By Making This Your Waterfront Retreat And Enjoy A Future Beautiful Suns...

Nice In Town 5 Unit Building. Great Location F...

Photo of Listing #4770829

$299,900 Active

  • 0.38 Acres
  • 3,978 ft²

Multi-Family

77 Richmond Rd, Winchester, New Hampshire

MLS® #4770829

Nice In Town 5 Unit Building. Great Location For Walking To Town. Ample Paved Parking. Vinyl Siding, City Water And Sewer. Nice Yard On A Corner Lot, Detached Barn/garage For Storage. Appealing Farmers Porch. Easy To Rent And Strong Cash Flow Investm...

If You Are Looking For One Of The Best Lake And...

Photo of Listing #4770179

$289,900 Active

  • 2 Beds
  • 1 Baths
  • 0.18 Acres
  • 1,560 ft²

Residential

29 Town Beach Rd, Winchester, New Hampshire

MLS® #4770179

If You Are Looking For One Of The Best Lake And Mountain Views, This Is The Home For You. This Immaculate 2 Bedroom, 1 Bath, Four Season Log Home Boasts A Massive Great Room With Cathedral Ceiling, 3 Levels Of Outdoor Entertaining, And 58 Feet Of Water Fron...

Beautifully Updated Center Chimney Colonial Loc...

Photo of Listing #4774875

$274,900 Active

  • 3 Beds
  • 2 Baths
  • 3.2 Acres
  • 2,619 ft²

Residential

369 Back Ashuelot Rd, Winchester, New Hampshire

MLS® #4774875

Beautifully Updated Center Chimney Colonial Located In An Extremely Pastoral Setting In The Charming Ashuelot District Of Winchester. Many, Many Antique Features Set The Tone For This Classic Property. 5 Fireplaces, All Said To Be Working. Beautiful Panelin...

Great 5-unit Investment Opportunity In Southwes...

Photo of Listing #4772273

$249,900 Active

  • 1 Acres
  • 7,305 ft²

Multi-Family

11 Ashuelot Main St, Winchester, New Hampshire

MLS® #4772273

Great 5-unit Investment Opportunity In Southwest Nh. All Units Leased. Three 2 Bedrooms And Two 3 Bedrooms Which Are In High Demand. All Electric And Heating Systems Have Been Updated. Fully Renovated. Situated On An Acre Of Land, Close To Town And With Amp...

Three Bedroom Home On Level Sloping Lot With Wa...

Photo of Listing #4776427

$235,000 Active

  • 3 Beds
  • 2 Baths
  • 1.9 Acres
  • 2,028 ft²

Residential

893 Old Westport Rd, Winchester, New Hampshire

MLS® #4776427

Three Bedroom Home On Level Sloping Lot With Water Frontage On The River And A Dock Ready To Launch Your Small Boat Or Enjoy Fishing From The Waters Edge. The Property Provides Many Possibilities For Extended Living By Relaxing On The Front Covered Porch, C...

Three Bedroom Two Story Home On 6 +/- Acres In ...

Photo of Listing #4764883

$225,000 Active

  • 3 Beds
  • 2 Baths
  • 6.8 Acres
  • 1,464 ft²

Residential

420 Burt Hill Rd, Winchester, New Hampshire

MLS® #4764883

Three Bedroom Two Story Home On 6 +/- Acres In Great Country Location. This Well Built Home Is Located On Quite Country Road Only Minutes From Keene, Brattelboro Or Mass. The Home Offers Hardwood Floors In The Dining Room And Foyer. Front To Back Living Roo...

Calling All Wind Power, Mountain Bike, Hiker An...

REDUCED 10% Photo of Listing #4692214

$224,000 Active

  • 230 Acres

Land

995 Keene Rd, Winchester, New Hampshire

MLS® #4692214

Calling All Wind Power, Mountain Bike, Hiker And Quiet Seeking Enthusiast To Look At This Gorgeous Interesting Parcel Being Offered For Sale. 230 Acres Of Real Nh Land, With Ledge Outcroppings, Enough Timber For A Lifetime Or To Build A Home(s) Of A Lifetim...

Water Front With Dock And Diving Platform. Cut...

Photo of Listing #4755884

$219,900 Active

  • 1 Beds
  • 1 Baths
  • 0.66 Acres
  • 944 ft²

Residential

15 Headlands Rd, Winchester, New Hampshire

MLS® #4755884

Water Front With Dock And Diving Platform. Cute As A Button 1 Bedroom Home. Enjoy The Family Room That Looks Right Out Onto The Lake. This Features A Living Room/dining Room And A Kitchen With A Woodstove. Neat & Clean Just Come Spend Your Summer Right O...

Located On The East Side Of Route 10 With 1407'...

Photo of Listing #4738222

$199,000 Active

  • 64.1 Acres

Land

Keene Rd, Winchester, New Hampshire

MLS® #4738222

Located On The East Side Of Route 10 With 1407' Road Frontage, Zoned Commercial To A Depth Of 500' With Remaining Land Zoned Agricultural. Electric Runs Right In Front Of Lot. The Lot Offers A Nice Cleared Area For Development.

Step Back In Time In This 4 Bedroom, 2 Bath 186...

REDUCED 3% Photo of Listing #4752743

$179,900 Active

  • 4 Beds
  • 2 Baths
  • 0.36 Acres
  • 2,152 ft²

Residential

31 Parker St, Winchester, New Hampshire

MLS® #4752743

Step Back In Time In This 4 Bedroom, 2 Bath 1860's Home In This Quaint New England Town. Take Advantage Of Many Upgrades, Including A Brand New Kitchen Floor, New Tub/shower, Painting Of The 3 Story Barn, New Stainless Refrigerator And Updated Outdoor De...

Affordable, Flexible, Comfort On An Acre Plus L...

REDUCED 7% Photo of Listing #4758356

$139,900 Active

  • 3 Beds
  • 2 Baths
  • 1.5 Acres
  • 1,943 ft²

Residential

21 Mechanic St, Winchester, New Hampshire

MLS® #4758356

Affordable, Flexible, Comfort On An Acre Plus Lot Make This Traditional New England Home A Great Opportunity. The Home Is A Single Family With An In-law Apartment On The 2nd Floor. The Current Owners Use The Three Bedrooms, Country Kitchen And Living Room O...

Charming And Cozy With An Eye On Efficient, All...

Photo of Listing #4752444

$125,000 Active

  • 3 Beds
  • 1 Baths
  • 0.16 Acres
  • 1,999 ft²

Residential

180 Ashuelot Main St, Winchester, New Hampshire

MLS® #4752444

Charming And Cozy With An Eye On Efficient, All Of The Hard Work Has Already Been Done. Just Needs A Little Elbow Grease To Shine. New Roof, New Vinyl Insulated Windows, New Furnace, New Flooring, New Coat Of Exterior Paint. There’s Even A 3-season Porch, ...

A Winchester Landmark, Deano's Pizzeria Is Avai...

REDUCED 14% Photo of Listing #4747211

$124,900 Active

Commercial

30 Keene Rd, Winchester, New Hampshire

MLS® #4747211

A Winchester Landmark, Deano's Pizzeria Is Available For The First Time Since 1983. Home Of Deano's Famous Pizza And Special Marinara. Includes All Of The Equipment. Lounge Area Can Be Closed Off For Private Functions. Lunch Counter And Booths In The Main S...

Developer And Contractor Dream Looking For Land...

REDUCED 8% Photo of Listing #4744216

$110,000 Active

  • 18.2 Acres

Land

90 Allen Hill Rd, Winchester, New Hampshire

MLS® #4744216

Developer And Contractor Dream Looking For Land But Now You Found Land With A Multifamily On 18.2 Acres Sub Dividable With Town Approval. Built Strong In 1710 Overlooking Beautiful Village Of Ashuelot, Property Has So Much Potential!! Current Building Is Zo...

Developer And Contractor Dream Multifamily On 1...

REDUCED 8% Photo of Listing #4744213

$110,000 Active

  • 18.2 Acres
  • 3,480 ft²

Multi-Family

90 Allen Hill Rd, Winchester, New Hampshire

MLS® #4744213

Developer And Contractor Dream Multifamily On 18.2 Acres Subdividable With Town Approval. Built Strong In 1710 Overlooking Beautiful Village Of Ashuelot, Property Has So Much Potential!! Current Building Is Zoned 2 Family However Has The Potential For More ...

Rare Opportunity For Waterfront Property On The...

Photo of Listing #4687314

$99,500 Active

  • 0.19 Acres

Land

11 Hemlock Ave, Winchester, New Hampshire

MLS® #4687314

Rare Opportunity For Waterfront Property On The Crystal Clear Waters Of Forest Lake. Land Currently Houses And Old Camp In Need Of Tearing Down, But Can Be Rebuilt On The Existing Footprint With Town Approvals. Camp Is Approximately 22’ X 24’. Reward Yourse...

Light And Bright Starter Home At The Top Of The...

REDUCED 2% Photo of Listing #4727377

$97,900 Active

  • 3 Beds
  • 1 Baths
  • 0.54 Acres
  • 1,239 ft²

Residential

53 Michigan St, Winchester, New Hampshire

MLS® #4727377

Light And Bright Starter Home At The Top Of The Hill. Recent Improvements Include New Siding, New Roof On The Storage Shed, Interior Paint, New Kitchen With Maple Cabinets, Newer Appliances, Laminate Flooring, New Bathroom Cabinets, Shower And Efficiency To...

Here Is A Clean Fixer Upper. No Damage To Addre...

Photo of Listing #4776744

$95,000 Active

  • 3 Beds
  • 2 Baths
  • 1 Acres
  • 1,400 ft²

Residential

36 Woodard Ave, Winchester, New Hampshire

MLS® #4776744

Here Is A Clean Fixer Upper. No Damage To Address, Just Finish It. Ample Room Sizes To Accommodate A Family Comfortably On One Level. The Master Has Double Doors To A Deck And With A Bath Vanity And Shower Enclosure It Has An En Suite. The Yard Is Level And...

 

Winchester area communities

Chesterfield

Fitzwilliam

Hinsdale

Jaffrey

Keene

Marlborough

Richmond

Rindge

Roxbury

Swanzey

Troy

Westmoreland

Winchester

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Listing information last updated on October 14th, 2019 at 7:36am EDT.