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44 Gunn Mountain Rd, Winchester
$349,900
4 Beds ⋅ 2 Baths ⋅ 5112930 MLS
When you look for a good family home, I hope you're lucky enough to find one like this! Same owners for the past 35yrs, mountains of updates and improvements, and investment! From the plumbing, heating system, 200A electrical, hot water, appliances, siding and so much more! (see the disclosures) The icing on the cake is the 24x36' garage with two full stories! You'll walk into a large sunroom, then step into a big family kitchen, with doorways to the office and living room. A full ADA bath on the first floor has a large step in shower, whirlpool tub and laundry! Beautiful floors throughout, replacement windows and tall ceilings will make you feel right at home. The garage is absolutely amazing, has dedicated electrical service, GOBS of storage or hobby space! (Garage was $75k) This is an affordable family home in a quiet setting that you can move into with confidence and pride.

44 Gunn Mountain Rd, Winchester

35 Old Spofford Rd, Winchester
$389,900
2 Beds ⋅ 2 Baths ⋅ 5112269 MLS
Nestled on 5 private acres in Winchester, you’ll find this charming ranch style home offering the perfect combination of one-level living, privacy, and outdoor recreation! Upon entering, you’ll be greeted by a large and inviting living room/kitchen with plenty of space to relax and entertain. This home offers a primary bedroom with a 1/2 bath, another generously sized bedroom, a laundry room, and a full bath on the main level. The finished basement provides even more livable space and features a pellet stove, making it a great spot for a recreation room, hobby area, or additional entertaining space. Step outside and enjoy the expansive wrap-around deck, where you can take in the peaceful views and beautiful private surroundings. The property directly abuts the Ashuelot Rail Trail, offering easy access to walking, biking, and other outdoor activities right from your own backyard! There is also plenty of room for all your toys, tools, and equipment with 2 sheds, a detached 1 car garage, and a metal carport. A detached ground-mounted solar panel system and generator hook up add to the functionality of this property. Located just 20 minutes from Keene, this home offers the privacy and tranquility of country living while still being conveniently close to shopping, restaurants, schools, medical facilities, and other amenities. Whether you’re looking for a full-time residence, weekend getaway, or simply a place to enjoy the peace and beauty of southwestern New Hampshire, this property has so much to offer! Schedule your private showing today!

35 Old Spofford Rd, Winchester

4 Elderberry Ln, Winchester
$299,000
3 Beds ⋅ 2 Baths ⋅ 5112014 MLS
Welcome to a charming 1885 historic home nestled on a private 0.77 acre lot in Ashuelot (Winchester), NH. Tucked back from the road, this character rich residence seamlessly combines classic New England architecture with practical modern updates. Inside, you will find beautiful hardwood floors and an abundance of custom built ins and clever storage solutions throughout. The kitchen features sleek stainless steel appliances, opening gracefully into inviting living spaces bathed in natural light. Upstairs, the home offers three comfortable bedrooms, perfect for family, guests, or a dedicated home office setup. Major mechanical upgrades provide complete peace of mind, including a newer furnace, water heater, and oil tank, alongside a full home generator that ensures uninterrupted power year-round. An attached one car garage adds convenience and extra storage. Outdoors, the expansive front and back yards create a quiet haven for leisure, outdoor dining, or cultivating your dream garden. Nature enthusiasts will love being just minutes away from local rail trails and the vast Pisgah State Park for year-round outdoor recreation. Enjoy the tranquility of a spacious, private setting while remaining close to nearby routes and amenities. This charming property is ready to welcome you home!

4 Elderberry Ln, Winchester

366 Keene Rd, Winchester
$449,000
3 Beds ⋅ 2 Baths ⋅ 5108720 MLS
Price Improvement!!!! Welcome HOME and move right in to this lovely 3 year old 2 story Colonial home!!! New Englander style featuring 3 bedrooms, 2 bathrooms and room for everyone! Enter into the home from your charming farmer's porch into a spacious living room; room for entertaining, movie or game nights and so much more!!! Expansive open concept kitchen and dining boasts fully applianced kitchen, granite countertops, large kitchen island and pantry. Sliders to your 16x12 deck off the dining room lead you to your level back yard where BBQs, yard games and gardening can take place. On the second level of the home you will find your spacious primary bedroom with walk in closet and large full bathroom. 2 additional ample sized bedrooms and laundry area complete the second floor. Close to town and amenities, walk to the town beach and boat launch, easy commute to Keene, Brattleboro and I91. This home is efficient, well built and ready for you. Don't miss the opportunity to make this wonderful home yours!!!

366 Keene Rd, Winchester

10 Burt Hill Rd, Winchester
$357,900
3 Beds ⋅ 2 Baths ⋅ 5105670 MLS
Generous price improvement!! Step inside this comfortable updated ranch. With 3 bedrooms, including the primary with en suite, 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, features newer flooring throughout, and 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 or tackle projects, the basement workshop provides a dedicated workspace as well as storage. This home offers low-maintenance living at its best. A home where you can spend less time on upkeep and more time enjoying life. Interior paint needs refreshing.

10 Burt Hill Rd, Winchester

71 Headlands 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

253 Back Ashuelot Rd, Winchester
$425,000
1 Beds ⋅ 1 Baths ⋅ 5095024 MLS
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. Recent work done to the ext. logs.. There has been a property flood evaluation done here & these homes are NOT in a flood zone less than a half hour to Keene and to Brattleboro.

253 Back Ashuelot Rd, Winchester

190 Ashuelot St, 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

305 Richmond Rd, Winchester
$475,000
5093431 MLS
ATTENTION INVESTORS! Through no fault of the Seller, this property is back on the market. The next Buyer will benefit from the July general and septic inspections. The bank ordered appraisal in excess of asking price is also available for review. This well-maintained multi-family property is located near the Massachusetts border, offering convenient access for commuters and tenants from both states. The property includes four residential units that are currently 100% occupied with reliable long-term tenants. It also features two separate income-producing workshop/garage spaces that provide additional revenue streams and enhance overall cash flow. Recent major capital improvements include a brand new roof, newly replaced rear stairs and decking, a fully replaced leach field, and septic connections to the two 1,000-gallon tanks that were serviced and replaced where needed. These updates ensure the property is in excellent condition and reduce future maintenance costs for the new owner. Tenants pay their own heat, hot water, and electricity, which keeps operating expenses low. This property has consistently delivered positive cash flow to the current owner, and keeping it occupied has never been an issue thanks to strong local demand. Current rents are below market rate and the leases are expiring, creating an immediate upside opportunity for a new owner to implement market-rate increases and boost net operating income right away. Whether you are an experienced investor looking to add a turnkey, low-maintenance asset to your portfolio or a buyer seeking a solid, cash-flowing property with built-in equity through recent upgrades, 305 Richmond Road is worth serious consideration. Priced to attract serious investors schedule your showing today and see the value for yourself. This property is not going to last long!

305 Richmond Rd, Winchester

166 Keene Rd, Winchester
$429,900
3 Beds ⋅ 2 Baths ⋅ 5092617 MLS
Welcome to 166 Keene Road in Winchester, a charming 3-bedroom, 1.5-bath New Englander that combines classic character with thoughtful modern updates. This inviting home offers comfortable living spaces, abundant natural light, and a warm atmosphere that immediately feels like home. Recent improvements include an updated roof, solar panels for enhanced energy efficiency, a spacious back deck ideal for entertaining and outdoor enjoyment, fresh paint throughout the interior, updated light fixtures, and a new dishwasher, allowing the next owner to move in with confidence. The functional floor plan provides flexibility for everyday living, whether you're gathering with family, working from home, or hosting friends. Outside, enjoy the benefits of outdoor living from the rear deck or wrap around front porch, perfect for summer barbecues, morning coffee, or simply relaxing while taking in the surroundings. The solar system helps reduce energy costs while adding long-term value and sustainability. 465' of frontage on Ashuelot River. Conveniently located with easy access to local amenities, schools, shopping, dining, and recreational opportunities, this property offers the perfect balance of small-town New Hampshire living and modern convenience. Easy commute to Keene, Mass, Brattleboro and Interstate 91.

166 Keene Rd, Winchester

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