Winchester Homes under $500,000

Welcome to Winchester, New Hampshire—a hidden gem nestled in the picturesque Cheshire County. This charming town is a delightful blend of natural beauty and small-town warmth, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle away from the hustle and bustle of city life.

Winchester boasts a rich history, with roots dating back to the early 18th century. The town is surrounded by stunning landscapes, including lush forests and serene lakes, perfect for outdoor enthusiasts. Enjoy hiking, fishing, or simply taking in the breathtaking views that this beautiful region has to offer. The community is tight-knit, with friendly locals who take pride in their town's heritage and vibrant culture.

For those looking to settle down in Winchester, you’ll be pleased to discover that there are numerous homes available for under $500,000. Whether you’re in search of a cozy cottage, a charming colonial, or a spacious family home, Winchester has a variety of options to suit your needs and budget. These homes often feature beautiful yards, modern amenities, and easy access to local schools and parks, making them perfect for families or those looking to downsize.

With its affordable housing market, welcoming atmosphere, and stunning natural surroundings, Winchester is a fantastic choice for anyone looking to make a fresh start. Come explore the beauty and charm of this enchanting town, and find your dream home in Winchester today!

Newest Winchester Homes under $500,000

$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

$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

$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

$269,900

1 Beds ⋅ 1 Baths ⋅ 5111797 MLS

Located just off the beaten path yet close to amenities and major routes sits this one level home waiting for you. Open concept kitchen and living room, ample sized bedroom and 2 additional rooms in the lower level that could be used for whatever you wish; office, spare bedroom, home gym, anything! Fully functional kitchen, fully applianced and plenty of storage; including multiple lazy susans in the cabinets for convenience. Forced hot air heat as well as a wood stove for a secondary heat source. 1.71 acres, private area and ready for immediate occupancy!! Don't miss this one!

1 Oak Cir, Winchester

$425,000

5110811 MLS

Large two family home!!! In town location. Close to schools, shopping and amenities. Many original features; staircase and lovely banister in entrance hall, moldings, fireplace surround as well as turret and alcove windows. Large units; one 2 bedroom and one 3 bedroom. All separate utilities. Well maintained property ready for you to take ownership!

42 Parker St, 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

$310,000

3 Beds ⋅ 1 Baths ⋅ 5107206 MLS

Price Reduction, Motivated Seller. Welcome to this beautifully renovated single-family home featuring 3 bedrooms and thoughtful new updates throughout. This move-in-ready property offers a comfortable and inviting layout, making it an excellent choice for a first-time homebuyer or anyone looking for a great starter home. With its fresh updates and welcoming atmosphere, this home is ready for its next owner to make it their own. Situated across the road from the Ashuelot River come take a look for yourself.

73 Ashuelot Main St, 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

$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

$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

$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

$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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