Refine Search
Sort by
398 Scofield Mountain Rd, Winchester
$3,995,000
4 Beds ⋅ 6 Baths ⋅ 5086956 MLS
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 top grade building components seamlessly blending industrial design with high-end finishes. This unparalleled estate has a private gated entrance that welcomes you, and leads you past a pond with water feature, & basketball court. This private sanctuary presents endless possibilities—luxury residence, event venue, or yoga retreat. Each floor of the residence was thoughtfully designed; the first floor offers seamless indoor/outdoor, open concept living with a chef’s kitchen, living room, guest suite, & mudroom. A floating staircase leads you to the second floor which is counter-leveled creating two 16x10 balconies at the rear of the home, & a 10x8 balcony above the front patio. Enjoy a serene primary suite, two additional en-suite bedrooms, & an office with glass door. The lower level includes a family room, wine room with built-ins, bunk space, full bath, & 4-car tandem garage. A 50x45 raised patio with outdoor kitchen creates effortless entertaining. Every detail was designed to balance function & beauty for all ages & lifestyles. Just 2 hours to Boston, the Seacoast, & Lakes Region. Home being sold fully furnished. Floor Plans and Video available.

398 Scofield Mountain Rd, Winchester

484 Scofield Mountain 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

49 Keene Rd, Winchester
$589,000
5114050 MLS
Welcome to this brand new, turn-key two-family home, offering the perfect opportunity for investors or owner-occupants looking to offset their mortgage! Each side of this modern duplex features an identical, spacious layout boasting 3 bedrooms and 1.5 bathrooms. Built from the ground up with contemporary living in mind, both units come with fully applianced kitchens equipped with brand-new refrigerators, stoves, microwaves, and dishwashers. Side-by-side design means no neighbors above or below you, maximizing peace and privacy. Enjoy complete independence and low maintenance with fully separate utilities for each unit, including individual meters for electricity, gas, and water. Each unit has a full basement with plenty of space for all of your needs. Whether you are an investor looking to add a premium, low-maintenance asset to your portfolio, or a homeowner looking to live in one side and let the tenant pay your mortgage, this property is a rare find.

49 Keene 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

366 Keene Rd, Winchester
$435,000
3 Beds ⋅ 2 Baths ⋅ 5108720 MLS
Welcome home to this stunning, three-year-old Colonial featuring 3 bedrooms and 2 bathrooms. Perfectly blending classic architectural charm with modern design, this home offers bright, spacious rooms and an open floor plan designed for effortless everyday living and entertaining. At the heart of the home is a chef-inspired kitchen equipped with a large center island, premium granite countertops, sleek cabinetry, and stainless steel appliances. The main level flows seamlessly from the kitchen into the inviting living and dining areas, creating a warm and connected atmosphere. Upstairs, you will find a generous primary suite with an en-suite bath, alongside two additional well-proportioned bedrooms and laundry area for your convenience. Step outside through the dining area to your private back deck, perfect for morning coffee or weekend barbecues. The deck overlooks a beautiful, level yard that offers plenty of space for outdoor activities, gardening, or relaxing in your own peaceful retreat. With all the benefits of recent construction, this home is entirely move-in ready.

366 Keene 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

156 Forest Lake Rd, Winchester
$377,000
4 Beds ⋅ 1 Baths ⋅ 5113915 MLS
Discover the possibilities at this inviting property set on 1.23 private acres in Winchester, New Hampshire! Offering 4 bedrooms, 1 full bath, and a versatile bonus room, this home provides plenty of space to make it your own. Whether you're looking for room to spread out, space for hobbies, or an opportunity to create a home that reflects your personal style, there's plenty of potential here. The bonus room offers flexibility for a home office, hobby space, playroom, or additional living area, depending on your needs. A 2-car garage provides valuable space for vehicles, storage, tools, or recreational equipment. Enjoy the privacy and breathing room of a generous lot while taking advantage of all that southwestern New Hampshire has to offer. If you've been searching for a property with four bedrooms, a garage, and room to make your vision a reality, 156 Forest Lake Road is worth a closer look. Bring your ideas and explore the possibilities!

156 Forest Lake Rd, Winchester

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

000 Burt Hill Rd, Winchester
$339,000
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

235 Ashuelot St, Winchester
$315,000
2 Beds ⋅ 1 Baths ⋅ 5114398 MLS
If you love spending time outdoors and entertaining, this is one you'll want to see! Welcome to 235 Ashuelot Street in Winchester, NH, where comfortable living meets an awesome backyard setup! Inside, you'll find two bedrooms, a full bathroom, and a comfortable, functional layout with living and dining spaces on the main floor. Downstairs, the partially finished basement offers a bonus room and plenty of additional space to make your own! Whether you're looking to create a family room, home office, workout area, or even add a second bathroom, there's plenty of potential to customize the space to fit your needs. But wait until you see the outdoor space! The covered pavilion takes outdoor entertaining to another level, complete with a mounted TV, ambient perimeter lighting, and plenty of room for comfortable seating. Whether you're catching the big game, hosting friends for a summer cookout, or relaxing with your favorite show on a warm evening, this space is designed to be enjoyed. Rain or shine, this is a space you'll want to use! Beyond the expansive deck, the spacious 0.69-acre lot offers plenty of room for outdoor activities, while the oversized shed provides tons of clean, dry storage space for all your tools, equipment, and seasonal items. As an added bonus, solar panels help keep energy costs down, allowing you to spend less on utilities and more on the things you enjoy! *Showings begin at the OPEN HOUSE 10/17/26 from 11AM-1PM!*

235 Ashuelot St, 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

Old Swanzey Road, Winchester
$65,000
5114283 MLS
Your opportunity to build in the beautiful Monadnock Region awaits! Situated in Winchester, NH, this 2.64-acre residentially zoned parcel offers an inviting country setting with the convenience of nearby amenities. Whether you're envisioning a cozy New England retreat or a custom-built home, this property provides an opportunity to bring your plans to life. Previously perc tested, the parcel is located in a rural area where you can enjoy the charm of small-town living without feeling far removed from everyday conveniences. Winchester offers a welcoming community atmosphere, outdoor recreation, and access to the natural beauty that makes southwestern New Hampshire such a desirable place to call home. Enjoy the best of both worlds with a peaceful setting and convenient access to Keene, neighboring communities, and the Massachusetts and Vermont borders. Bring your vision and explore the possibilities of making this property your own!

Old Swanzey Road, Winchester

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .

How much is your home worth?

Get instant property value now!