Winchester Real Estate

Welcome to Winchester, New Hampshire—a charming town nestled in the heart of Cheshire County. With its picturesque landscapes and rich history, Winchester offers a unique blend of small-town charm and natural beauty, making it an ideal place to call home.

Winchester is renowned for its serene environment, characterized by rolling hills, lush forests, and tranquil lakes. The town is bordered by the stunning Connecticut River, providing ample opportunities for outdoor enthusiasts to engage in activities such as fishing, kayaking, and hiking. The nearby Pisgah State Park, with its expansive trails and diverse wildlife, is perfect for those who appreciate nature’s wonders.

The town’s historical roots run deep, with many well-preserved buildings that tell the story of its founding in the early 18th century. The Winchester Historical Society offers a glimpse into the past, showcasing artifacts and documents that highlight the town's rich heritage. Community events, such as the annual Winchester Old Home Day, foster a strong sense of belonging among residents and celebrate the town’s vibrant culture.

Winchester’s friendly atmosphere is complemented by a close-knit community. Local shops, farmers' markets, and cozy eateries provide a warm welcome, while schools in the area prioritize education and personal growth, making it an excellent place for families.

Whether you’re looking for a peaceful retreat or a place to raise a family, Winchester, NH, offers a delightful blend of history, community, and natural beauty. Explore the charm of this hidden gem and discover why so many are proud to call it home!

Newest Listings in Winchester

$99,000

4 Beds ⋅ 2 Baths ⋅ 5107063 MLS

Opportunity awaits on this .30 acre lot. Currently home to a double wide mobile home that has been completely gutted inside, this property is a blank canvas ready for extensive rehabilitation. Bring your vision and make it your own. A wide variety of possibilities exist here, making it a fantastic option for investors or anyone looking to take on a rewarding project. Location is everything, and this one delivers. Directly across the street, the Ashuelot River offers great kayaking right at your doorstep. The property also backs up to Pisgah State Park, home to thousands of miles of trails across both private and state managed lands, perfect for hiking, biking, and exploring right from your backyard. Outdoor recreation enthusiasts will also love the convenience of the OHRV staging area just down the street, offering easy access for off road adventures. property has a shared well with neighboring property. Seller has never occupied the property. Property is being sold AS IS. This property includes a camper and pickup truck, along with various items left on site, all to be conveyed with the sale at no additional cost. Buyer assumes full responsibility for removal and disposal of these items, which are included strictly on as is basis. no warranties expressed or implied. Buyers are responsible for conducting their own due diligence regarding zoning,shared well, and all other aspects of the property. Don't miss this chance to create something special in a location that offers unbeatable access to nature and recreation.

357 Ashuolet Main St, Winchester

$650,000

2 Beds ⋅ 2 Baths ⋅ 5106346 MLS

Bring your dreams to life on this sprawling 17.8-acre Winchester property, offering endless opportunities to create the homestead you’ve been waiting for! The 1.75-story log cabin features two bedrooms, two full baths, and a bonus room that could serve as a third bedroom. Vaulted ceilings and a stone fireplace create a warm and inviting living space, while multiple porches spanning three sides of the home provide plenty of room to relax and enjoy the peaceful surroundings. The updated kitchen and first-floor bathroom, first-floor laundry, and full basement are additional features of this well-maintained home. This property offers so much more than just a home. A three-car garage (24x28) with a rear lean-to provides additional storage, while the six-bay shop (22x36) offers plenty of room for vehicles, equipment, and projects, complete with workbench areas and more rear lean-to storage. The two-story barn (30x52) features water and electricity, stalls, and a tack room. Outside, fruit trees are scattered on the front lawn and gardens can be found across landscaped grounds. Up on a knoll behind the house, you’ll find a self-proclaimed “campground,” complete with an RV pole barn (20x36), water access, and multiple electrical hookups. A screen house, wood shed, and fire pit create a perfect gathering space overlooking the field and pond. Whether you’re looking for space for your hobbies, animals, equipment, family, or a private place to make your own, this property offers the space and flexibility to do so. Conveniently located in Winchester, NH, just 20 minutes from Keene, 30 minutes from Brattleboro, VT, and 10 minutes from the Massachusetts border. Realtor is a relative of the seller. Seller has never occupied the property. Buyers to do their own due diligence. Please do not access the property without being accompanied by a licensed agent.

60 Forest Lake Rd, Winchester

$369,900

3 Beds ⋅ 2 Baths ⋅ 5105670 MLS

Step inside this comfortable and thoughtfully updated ranch. With 3 bedrooms, including the primary suite, and 2 baths, this home is designed for easy, enjoyable living with space for all. Enjoy the outdoors from the huge screened-in porch, perfect for relaxing, entertaining, or simply taking in the peaceful surroundings. An additional enclosed porch provides even more flexible living space. The home has been modified for added accessibility, and features newer flooring throughout, along with central A/C for year-round comfort. Peace of mind comes easy with an automatic standby generator, while the vinyl siding and metal roof provide durable, low-maintenance exterior protection. The fenced-in backyard offers a great space for pets, gardening, recreation, or simply enjoying the outdoors. For those who like to tinker, create, or tackle projects, the basement workshop provides valuable dedicated workspace and storage. With its accessible features, comfortable living spaces, durable improvements, and outdoor amenities, this is low-maintenance living at its best. A home where you can spend less time on upkeep and more time enjoying life. Refresh the interior with your own paint colors. Schedule your showing now or visit at your convenience, one of our upcoming open houses 8/22/26 and 8/23/26 from 11:00 A.M. to 2:00 P.M.

10 Burt Hill Rd, Winchester

$349,900

3 Beds ⋅ 2 Baths ⋅ 5105078 MLS

Set along a tranquil road with seamless access to Route 91, Vermont, Massachusetts, and Keene, this inviting single-story ranch rests on an expansive lot, offering an ideal setup for first-time buyers or anyone seeking an easier, simplified lifestyle. Inside, sun-drenched living areas feature classic hardwood floors, rich pine paneling, and broad windows that fill the space with warmth and pleasant scenery. The spacious kitchen is well-equipped with abundant cabinetry, two bright windows, and a multi-functional island peninsula featuring extra prep space on one side and casual seating on the other, while the adjacent dining nook includes a cozy window seat perfect for dining or relaxing with a book. A generously sized full bathroom thoughtfully incorporates laundry facilities alongside custom built-in drawers and storage. For seasonal outdoor enjoyment, the home extends out to a screened porch and a private patio enclosed by brick and stone walls that evoke a hidden garden retreat. Complete with a wood stove connection, an attached two-car garage, and a paved driveway, this charming home is a wonderful opportunity!

88 Back Ashuelot Rd, Winchester

$499,900

2 Beds ⋅ 2 Baths ⋅ 5101659 MLS

Set back from the road at the end of a well-maintained driveway sits this adorable waterfront home with gorgeous views over Forest Lake! The property features an open concept kitchen/dining/living area overlooking the water, a large deck, screened in porch, 2 ample sized bedrooms plus a full bath to complete the first level. Downstairs offers a bonus bunk room, sitting area, plus bath and laundry. Add in the handy storage shed, plenty of available parking spaces, large .40 acre lot, private dock and beach area on your 103 feet of lake frontage, and you have the total package!

418 Forest Lake Rd, Winchester

$599,000

3 Beds ⋅ 2 Baths ⋅ 5101558 MLS

Rustic charm, warm wood accents and lovely beam ceilings make this true log house feel like HOME. The outdoor space is a dream; situated on 6.32 acres, this property features a charming front porch, large back deck to relax on warm summer nights, spacious yard with fire pit for cold winter nights & smores, walking and ATV trails and your very own Christmas trees growing! Well landscaped with many perennials to enjoy throughout all of the seasons. Inside timeless log home charm meets all of the modern updates and amenities throughout. This 3 bedroom home has so much to offer; the main floor living boasts a spacious living room featuring a stunning fireplace, wide plank pine floors and wood beam ceilings; fully applianced kitchen with brand new appliances, woodburning Crawford cookstove as well as gas stove, plenty of cabinets and a breakfast bar. A first floor office or bedroom, lovely tiled full bathroom and a large sunroom displaying tiled floors and woodstove offer access to the expansive yard through the sliding glass doors. Enjoy access to the attached two car garage complete with a large bonus room; perfect for guests, a game or movie room and so much more! On the second story of the home you will find the primary bedroom presenting a walk in closet and tiled bathroom with walk in shower. Additionally there are 2 more bedrooms that complete the upstairs. Fine quality throughout and attention to detail make this home a true retreat!! Private yet minutes to amenities!

484 Scofield Mountain Rd, Winchester

$380,000

5100318 MLS

An extraordinary opportunity awaits on Burt Hill Road in Winchester, New Hampshire. Spanning a massive 118 +/- contiguous acres, this expansive wooded parcel offers an unbeatable blend of privacy, natural beauty, and strategic location. Situated directly at New Hampshire’s southwestern border, the property provides the ultimate tax-friendly NH lifestyle while remaining exceptionally accessible for Massachusetts commuters and weekenders alike. The land features a beautiful tapestry of rolling hills and mature forest. With a bit of clearing, the high elevations yield the potential for absolutely breathtaking, panoramic views of the surrounding Monadnock region. For the immediate investor or homesteader, the property holds significant timber value that could be harvested to offset initial costs or create custom clearings for your dream estate and 1 acre has been set out for building in the current use plan so no additional tax for buyer on that. Whether you are looking to build a private family compound, establish an off-grid sanctuary, or explore a larger project, the canvas is yours. With town approvals, this substantial acreage holds excellent potential for the future. Don't miss out on one of the largest available tracts in the area.

000 Burt Hill Rd, Winchester

$324,900

2 Beds ⋅ 1 Baths ⋅ 5098523 MLS

Welcome home to Ashuelot Road! Enjoy your quiet, extremely well-maintained river front home for many years to come. Just steps from the Ashuelot river and rail trail, this home is perfect for anyone seeking rest and relaxation from the busy days life brings. Featuring a brand new metal roof, as well as a brand new composite back deck and front entry way, you will never have to worry about exterior maintenance again. Inside you'll find a bright open concept living room and eat-in kitchen, along with one full bathroom and 2 spacious bedrooms. Many of the windows are also brand new, including the slider that leads to the new back deck. The dry walkout basement and framed walkup attic are ready for your dreams and design, which will allow for easy expansion of the living space in this beautiful cape. Don't miss out on your chance to own a TURN KEY riverfront home today.

229 Back Ashuelot Rd, Winchester

$445,000

3 Beds ⋅ 2 Baths ⋅ 5096976 MLS

This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines comfort, character, and stunning water views. Relax on the enclosed porch or one of several decks while enjoying the peaceful lakeside setting. The open-concept living and dining area features a pellet stove and abundant windows that capture beautiful lake views throughout the seasons. Outdoor living takes center stage, whether you're enjoying your morning coffee on the porch, entertaining on the decks, or spending the day on the water. A separate mobile home that has not been used for some time and could potentially serve as a guest cottage or private accommodation for family and visitors. It includes a living room, kitchen with pantry, bedroom, bathroom, attached shed, its own septic system, and a wood stove ready for hookup. Whether you're seeking a year-round residence, vacation getaway, or a property with space for extended family and guests, this unique waterfront offering provides the perfect blend of tranquility, recreation, and lakeside living.

71 Headlands Rd, Winchester

$150,000

2 Beds ⋅ 1 Baths ⋅ 5096726 MLS

Unique opportunity to get two for the price of one. Sale includes two (2) lots! House and garage are located on 6.3 acres and there's an additional 1 acre lot across the street according to the town records. Located close to town and major routes sits this 1975 mobile home. Two car garage with storage above and large storage shed. Private water and septic. Live in the home as is or build a new one!! Lots of opportunity here! Don't wait and miss your chance.

369 Manning Hill Rd, Winchester

$425,000

1 Beds ⋅ 1 Baths ⋅ 5095024 MLS

Presently a contractor who has experience with caring for log homes is applying a special power wash to the main home here. Are you a company boss, family or a fun loving person or one who just wants to relax and enjoy your own RIVERFRONT? These 2 buildings & the open yard can provide room for MANY to stay overnight & enjoy dinners & indoor & outdoor fun. You have been putting in key words as you search for a special property. "log home, my own river waterfront, kayaking, fishing, privacy, guest house or art studio, garage, garden areas, nearby hiking and snowmobiling,year round fun" ...Well here you are! This delightful log home has an open concept first floor with many windows to the yard , beautiful pine floors, a spacious bathroom with a large shower a large bedroom on the second floor. the water view side of the first floor could be enclosed for a bedroom. It has BBHW oil heat. NH Fish and Game stocks the river with fish. Close by are hiking and snowmobile trails (Ashuelot) bridge . Pisgah Park is nearby. You can kayak to Town from your yard along the Ashuelot River.. Enjoy the pavilion picnic place overlooking the river. Across the lawn is the guest house (cabin or art studio) built in 2012. The first floor is open concept and the second floor has a bathroom, the walls have been insulated, there is electric heat but one might add a mini-split for winter use. You can sit on the deck and relish the river view. The river side front yard gets lots of afternoon sun on a good day. The paved driveway leads to the 2 car garage for vehicles and boat storage, a newer roof and just a few steps to the 8x6 mudroom into the kitchen/living area. If you want privacy but still want a few friendly area neighbors the Back Ashuelot Rd. area is for you! Just off Rte.10 it is a short drive to Rte. 91 and picturesque routes to Eastern Massachusetts, and sbout 30 minutes to Keene,NH or Brattleboro,Vt. less than a half hour to Keene and to Brattleboro.

253 Back Ashuelot Rd, Winchester

$120,000

3 Beds ⋅ 1 Baths ⋅ 5094108 MLS

Calling all renovators, dreamers, and HGTV enthusiasts! If you've been looking for a project with great bones and an even better location, 190 Ashuelot Street might be the one. Nestled on 1.4 acres and directly abutting the Ashuelot Rail Trail, this 3-bedroom, 1 bath home is ready for its next chapter. Inside you'll find a large country kitchen, plenty of space to reimagine, and loads of potential. Outside, mature flowering and fruit trees add charm to the yard, while the detached 2-car garage provides room for vehicles, toys, or your next workshop project. Love the outdoors? Step right onto the Rail Trail for walking, biking, snowmobiling, and year-round adventure. Bring your vision, your toolbox, and a little elbow grease—this diamond in the rough is waiting to shine again! Property is being sold as-is. Cash Buyers Only.

190 Ashuelot St, Winchester

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