$129,000 $89 per sq.ft. Winchester NH Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1457  |  Acres: 1.4
Thursday Jun 11, 2026
Description: 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. See MLS Property & Listing Details & 13 images.

$499,900 $276 per sq.ft. Winchester NH Home »

465 Ft. of Waterfront on River Ashuelot River
3 Beds | 2 Baths |   Total Sq. Ft. 1808  |  Acres: 4.3
Wednesday Jun 3, 2026
Description: ** OPEN HOUSE SATURDAY, JUNE 6 FROM 11AM-1PM** 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. See MLS Property & Listing Details & 60 images.

$599,000 $392 per sq.ft. Winchester NH Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1528  |  Acres: 1.16
Monday Jun 8, 2026
Description: Brand-new construction offering the perfect blend of modern design, comfort, and future potential. Set on 1.16 acres on a town-maintained dead-end road, this thoughtfully designed 3-bedroom, 2-bath ranch provides easy one-level living with room to grow. Inside, you'll find a bright open-concept layout featuring durable flooring, recessed lighting, and abundant natural light. The spacious kitchen is the heart of the home, complete with an oversized center island, stainless steel appliances, ample cabinetry, and generous counter space. It flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. The primary suite offers a private retreat with a double vanity, step-in shower, and ample closet space. Two additional bedrooms and a second full bath provide flexibility for family, guests, or a home office. A dedicated laundry room with built-in cabinetry adds convenience and extra storage. One of the home's standout features is the expansive covered rear deck, perfect for morning coffee, outdoor dining, entertaining, or simply enjoying the peaceful hillside setting. The attached two-car garage provides direct access and additional storage. The full walkout lower level offers outstanding expansion potential. With excellent ceiling height, natural light, exterior access, and framing already in place, it presents the opportunity to nearly double the home's usable living space. Whether you envision a family room, gym, guest suite, workshop, or recreation area, the possibilities are endless. Modern mechanical systems, quality craftsmanship, and the peace of mind that comes with new construction make this a low-maintenance home for years to come. Whether you're a first-time buyer, seeking one-level living, or looking for future expansion opportunities, this move-in-ready home delivers exceptional value without the wait. See MLS Property & Listing Details & 38 images. Includes a Virtual Tour

$724,900 $479 per sq.ft. Winchester NH Home »

Price Change! Reduced by $25,000 down 3% on June 10th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2671  |  Acres: 37
Friday May 15, 2026
Description: Own your piece of paradise! Rarely does a property offering this much land and a beautifully maintained home become available in Cheshire County, NH. This single-owner Cape-style home features 3 bedrooms, 2 bathrooms, and a finished walk-out lower-level in-law suite, all set on approximately 37± acres with peaceful privacy and stunning natural surroundings. Inside, you'll find a warm and functional layout with custom cherry wood kitchen cabinets, natural wood finishes, a breakfast bar, and formal dining room. The living room is filled with abundant natural light, while mini-split heating and cooling provide year-round comfort. A standing seam metal roof offers added durability and peace of mind, while the 2-flue chimney provides the option for wood or pellet stove hook-up. One of the home's standout features is the 16x16 enclosed sitting porch complete with custom windows, beautiful woodwork, insulation, and a gas stove, creating a perfect year-round retreat. The first-floor primary bedroom offers slider access to a private deck and is conveniently located near a full bath with jacuzzi tub. Upstairs are two additional bedrooms with oversized skylights and windows bringing in exceptional natural light. The finished walk-out lower level includes a full in-law suite with kitchen, bath, washer and dryer, and slider access, ideal for multi-generational living or rental potential. The land is equally impressive, featuring approximately 20± acres of fenced pasture used for horses since 1987, plus additional acreage with trails, timber, streams, a pond, and beautiful views. Outdoor amenities include an above-ground pool, gazebo, koi pond, fruit trees including peach and apple, perennial gardens, garage space, hardscaping, and a versatile barn/shed perfect for animals, hobbies, storage, or workshop use. Enjoy peaceful country living while remaining close to town amenities. A truly special property offering space, functionality, and endless possibilities. See MLS Property & Listing Details & 55 images.

$395,000 $247 per sq.ft. Windham VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1600  |  Acres: 1.7
Thursday May 28, 2026
Description: Discover your perfect Vermont getaway in this well-maintained 3 BR, 2 BA home. Designed for both relaxation and year-round adventure, this property places you minutes from southern Vermont's best skiing and charming village life. The first level offers ultimate convenience, featuring a roomy, tiled mud room for all your gear, two comfortable BRs, full bath and a private primary suite complete with ensuite bath. The home's upper level is dedicated to spacious, comfortable living. To the right, a bright living area beckons, with a pair of sliding glass doors leading out to your brand new deck--the perfect place to enjoy a quiet cup of coffee, or glass of wine. The layout flows seamlessly into a large dining room, ideal for hosting delicious meals and great conversations with your favorite people. The well-appointed kitchen is ready to inspire your culinary creativity, or simply handle a quick snack. Perfectly nestled on a quiet road, the location is unbeatable for the outdoor enthusiast. You are just 10 minutes to Magic Mountain, a quick 20 minutes to Stratton or Bromley, and under 30 minutes to Okemo. Your four-season mountain adventure starts here. SHOWINGS BEGIN WITH OPEN HOUSE - SATURDAY, 5/30 & SUNDAY, 5/31 2 - 4PM. See MLS Property & Listing Details & 40 images.

$430,000 $517 per sq.ft. Winhall VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 1664  |  Acres: 1
Thursday Jun 11, 2026
Description: The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a delightful retreat. See MLS Property & Listing Details & 22 images.

$449,000 $460 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1460  |  Acres: 0.47
Thursday May 14, 2026
Description: A Sanctuary for Every Season: Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you're here to chase the morning light on the slopes of nearby Stratton Resort or to spend a slow summer afternoon exploring the local swimming holes, this home serves as the perfect basecamp for your Green Mountain adventures. Inside, the vibe is cozy. On crisp autumn evenings, the pellet stove becomes the heart of the home, casting a steady warmth that invites long conversations and board game marathons. When the Vermont summer hits its peak, you'll stay perfectly cool thanks to the modern mini-split system--a rare and welcome comfort in a mountain retreat. The expansive deck is your private outdoor dining room, ideal for long weekend brunches or stargazing after a day of hiking. With four bedrooms and 2.5 baths, there is plenty of space for everyone to find their own corner of peace without feeling crowded. A dedicated storage shed means your paddleboards, skis, canoes, and fishing gear are always organized and ready for the next excursion. You can feel the care that has gone into this property. It has been kept in peak condition so that your only job upon arrival is to drop your bags and head outside. From the gear storage to the effortless climate control, every detail has been managed to make your mountain getaways seamless. The mountains are calling, and this chalet is the perfect place to answer. Contact us today to see this Winhall gem in person and start planning your first weekend away. See MLS Property & Listing Details & 32 images. Includes a Virtual Tour

$495,000 $271 per sq.ft. Winhall VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1824  |  Acres: 0.4
Thursday May 28, 2026
Description: Quintessential Vermont charm meets modern comfort in this beautifully updated New England farmhouse just minutes from Stratton Mountain. Ideally located only 1 mile from the Stratton Mountain Access Road and just 1/10 mile to the VAST snowmobile trail, this 4-bedroom, 2-bath home offers the perfect four-season retreat. Rich with character, the home features exposed beams, warm hardwood floors, and a classic cast iron wood stove that creates the ultimate cozy Vermont atmosphere. Thoughtfully modernized while preserving its historic charm, this inviting property blends timeless farmhouse appeal with everyday comfort. Once a gathering place for legendary folk singer Arlo Guthrie, the home carries a unique sense of history and soul. Enjoy easy access to skiing, snowmobiling, hiking, and The Mountain School at Winhall, embracing the classic placement of historic Vermont farmhouses, originally built close to the road for practical year-round access during harsh New England winters. Today, that timeless design translates into effortless convenience with easy in-and-out access and no long driveway to maintain or plow, all while enjoying the beauty and charm of Vermont living. Whether you're searching for a primary residence, weekend getaway, or investment opportunity, this special property captures the very best of Vermont living. See MLS Property & Listing Details & 39 images.

$799,000 $354 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3078  |  Acres: 1.5
Thursday May 21, 2026
Description: Spacious and light-filled four-bedroom home ideally located in desirable Strattonwald, offering both winter and summer enjoyment in a private, peaceful setting. Enjoy convenient access to the Stratton winter shuttle, as well as summer amenities including a private pond and tennis courts. The home features generous living spaces perfect for gathering and entertaining, including a cozy fireplace and a large lower-level family room. Abundant natural light, ample closet space throughout, and a spacious primary suite with a large walk-in closet add to the home's appeal. Red Brook runs peacefully along the back of the property, enhancing the serene surroundings. An oversized garage includes a large unfinished room above, ready for your personal vision or expansion. The home is equipped with a generator for added peace of mind, and the furnace is just two years old. Sellers have completed a building, chimney, water, septic, and pest inspection, and all reports are available to any interested party. Please note: the indoor hot tub is currently not functioning. See MLS Property & Listing Details & 35 images.

$899,000 $300 per sq.ft. Winhall VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 4000  |  Acres: 1.1
Thursday May 14, 2026
Description: POSTPONED OPENHOUSE Spacious 4,000± sq. ft. contemporary home located in a sought-after ski resort community with convenient winter shuttle bus access to the slopes. Designed for both entertaining and everyday comfort, this property features an open-concept floor plan, abundant natural light, and generous living spaces throughout. The inviting family recreation room with bar offers the perfect setting for gatherings, game nights, or relaxing après-ski evenings. Additional highlights include a screened in porch , heated two-car garage, multiple entertaining areas, expansive deck and a seamless blend of mountain charm and modern design. Additional detached workshop on sight for all your storage needs. Ideal as a primary residence, vacation getaway, or investment property in a premier four-season destination. Stratton Fitness Ctr bond available to purchase. See MLS Property & Listing Details & 59 images.

$1,100,000 $342 per sq.ft. Winhall VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 4453  |  Acres: 1
Thursday May 21, 2026
Description: Tucked into Stratton Mountain Resort's sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering, relaxing, and enjoying all four seasons in Vermont. Recent exterior improvements have significantly enhanced the home's appearance and overall exterior presentation. Extensive work included reconstruction and upgrading of major exterior sections, along with new windows, roofing, trim, upgraded siding, exterior refinishing, and fresh paint. Complemented by a standing seam metal roof and updated exterior detailing, the home now offers a refreshed mountain exterior with a warm and inviting presence. Inside, the layout is exceptionally functional and inviting. The main level features an open kitchen, dining area, and vaulted living room with fireplace, along with a sunroom, screened porch, stone patio, and private primary suite. A mudroom with half bath off the attached two-car garage adds convenience for ski season and everyday living. Upstairs offers three additional bedrooms, a full bath with double vanity, and an airy loft overlook. The finished walkout lower level is built for entertaining and flexible living, featuring a spacious family room with wood stove and sliders, custom bar area, guest bedroom and bath, additional half bath, laundry, utility areas, and wide hallways throughout. Located just minutes from the slopes, golf course, village, and shuttle access, this is a rare opportunity to own a substantial Stratton mountain home with significant exterior improvements already completed, while still offering the chance to bring your own vision and style to the interior spaces. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour

$1,100,000 $450 per sq.ft. Winhall VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 2745  |  Acres: 10.4
Wednesday Jun 10, 2026
Description: Nestled on 10 private acres just off the Stratton Mountain Access Road, 65 Lower Taylor Hill Road offers a rare opportunity to own a beautifully renovated Vermont retreat ideally positioned between Stratton Mountain Resort and the area's endless four-season recreation. Surrounded by mature woodlands and exceptional privacy, this property offers a three-bedroom, three-bath main house along with a charming bunk house. The home combines refined craftsmanship, modern amenities, and timeless mountain charm. The thoughtfully redesigned interior is highlighted by a dramatic entryway featuring soaring ceilings with exposed beams and beautiful sight lines to the original great room and spacious dining area surrounded by spectacular forest views. French doors from the great room flow onto an expansive covered deck providing sweeping views of the gorgeous mountain surroundings - the perfect place to begin or end the day. Grounding the entry are heated slate tile floors and a convenient mudroom. The stunning all-new custom kitchen features hardwood shaker-style cabinetry, crown molding, elegant slate countertops and professional-grade stainless steel Café appliances. The first-floor master suite includes custom wardrobes and large French doors leading to a private deck. The private en-suite bath features heated slate tile floors, walk-in tile shower, and Kohler finishes. Completing the main floor is a full bath with spacious walk-in tile shower and heated floors. The sunny second floor features two large bedrooms and loft area. The full bath also boasts heated slate tile floors as well as a curved basin tub, and Kohler finishes. The finished basement area includes family space and an adjacent laundry room with new full-sized washer and dryer. The "family favorite" bunk house provides a rustic studio-style flex space with kitchen, full bath, living area, and a roomy loft. Beautiful French doors provide treetop views and lead to a private outdoor sitting area. See MLS Property & Listing Details & 60 images.

$1,225,000 $507 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3357  |  Acres: 1.2
Wednesday May 20, 2026
Description: Located in Stratton Resort's sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent renovations include updates to the kitchen and carpeting, creating a move-in ready retreat for all seasons. A spacious wraparound deck with hot tub provides the ideal setting to relax after a day on the slopes. The separate family room, complete with an adjacent full bath, offers excellent flexibility and can easily serve as additional sleeping space for guests. Additional highlights include an attached two-car garage and shuttle service access to Stratton's ski slopes, winter activities, Stratton Village, shopping, and dining. Active Stratton Sport Center Bond. See MLS Property & Listing Details & 47 images.

$1,990,000 $429 per sq.ft. Winhall VT Home »

6 Beds | 7 Baths |   Total Sq. Ft. 5896  |  Acres: 1.49
Thursday Jun 4, 2026
Description: Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower level features a full bar, game room, family room, and wood-burning fireplace, creating an ideal setting for après-ski entertaining. The primary suite serves as a private retreat with a spa-like bath, indoor sauna, hot tub, and oversized shower. Outdoor living is equally impressive. The expansive deck functions as a four-season outdoor kitchen and lounge complete with a covered porch, wood-fired pizza oven, gas grill, and gas fire pit. A landscaped level yard provides additional usable outdoor space, while a second outdoor hot tub extends the home's resort-style amenities. Recent improvements include updated Thermador appliances and a new roof. Additional features include a heated two-car garage and direct access to the Stratton shuttle route. A standout feature is the home's ability to operate as two fully independent residences, each with its own kitchen and laundry. This flexible configuration creates opportunities for personal use, hosting guests, or maximizing rental income throughout the year. See MLS Property & Listing Details & 54 images.

$499,900 $340 per sq.ft. Wolfeboro NH Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1470  |  Acres: 0.21
Friday May 22, 2026
Description: Located just minutes from downtown Wolfeboro and the shores of Crescent Lake, this inviting 2-bedroom, 2-bath home offers year-round water views, direct access to outdoor recreation, and the convenience of in-town living. The open-concept first floor creates a bright and welcoming living space, perfect for entertaining or relaxing after a day on the water. Step outside onto the spacious deck featuring a street-side privacy wall, ideal for outdoor dining and gatherings. Two sets of french doors in the basement open directly to the backyard, which is adjacent to the Cotton Valley Rail Trail, offering easy walking and biking access to nearby Mast Landing Boat Launch. A fenced portion of the yard adds flexibility for pets, gardening, or outdoor enjoyment. Whether you're seeking a year-round residence, vacation getaway, or investment opportunity, this home combines location, recreation, and comfort in one desirable package! See MLS Property & Listing Details & 31 images. Includes a Virtual Tour