$384,999 $141 per sq.ft. Winchester NH Home »

Price Change! Reduced by $65,001 down 17% on June 10th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2736  |  Acres: 0.19
Thursday Apr 23, 2026
Description: Beautifully renovated while still full of warmth and character, this Winchester home offers the perfect blend of modern updates and timeless charm. Completely rebuilt and thoughtfully redesigned, this property features new framing, new insulation, new plumbing, a new furnace, new roof, new siding, new windows, all new appliances, and new 200 amp electrical service with a second-floor subpanel for added convenience and future flexibility. Giving buyers peace of mind for years to come. Fully inspected and granted its Certificate of Occupancy, this home is truly move-in ready. Inside, you'll find a bright open concept first floor ideal for entertaining, filled with natural light from the many windows throughout the home. The handcrafted pine staircases add warmth and unique character, while the deep well upstairs windows create the perfect sun filled space for plant lovers. Offering 4 bedrooms and 3 bathrooms, the layout provides both comfort and functionality for everyday living. Located in a welcoming neighborhood just off the main road, this home is conveniently close to local shops, walking paths, and everyday amenities while still feeling comfortably tucked away. Motivated Sellers Agent related to seller See MLS Property & Listing Details & 41 images.

$459,900 $204 per sq.ft. Winchester NH Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2252  |  Acres: 0.61
Monday May 4, 2026
Description: A Beautiful and tastefully renovated home is what you will find when you view this lovely property!! This 2.5 story New Englander is situated on over half an acre with lovely landscaping throughout the yard, 2 decks for relaxing and summer BBQs, detached garage, room to garden and close to town and all amenities in a quiet and charming neighborhood. As you step inside you will take in all of the natural light throughout the home. Exceptional and fully applianced, functional kitchen boasts an abundance of cabinetry, granite countertops and lovely tiled backsplash, ceramic tile floors, double oven for those baking days, stainless steel appliances and a separate pantry. Charming breakfast room with views to the backyard, formal dining room, living room with large bay window and access to the foyer, large enclosed and heated sun porch for year round use and an attractive half bathroom complete the first floor of this home. The second floor boasts 4 spacious bedrooms with plenty of closet and storage space, an aesthetically pleasing 3/4 bathroom with tiled shower and glass enclosure, 2nd floor craft or utility room with laundry area as well as access to the 2nd floor deck and barn. The third floor of this spacious home provides room for all of your storage needs in the attic area which could easily be finished should one like to do so. This home is ready for you to move in and offers so much opportunity to live and grow in an absolutely exquisite property! Do not miss this one; it is a true gem! See MLS Property & Listing Details & 60 images.

$4,250,000 $1,207 per sq.ft. Winchester NH Home »

4 Beds | 6 Baths |   Total Sq. Ft. 5120  |  Acres: 141
Monday May 4, 2026
Description: 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. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$250,000 $166 per sq.ft. Windham VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 1504  |  Acres: 2.6
Tuesday Dec 17, 2024
Description: Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor. Home is ready for your improvements. Close to ski resorts! See MLS Property & Listing Details & 18 images.

$695,000 $290 per sq.ft. Windham VT Home »

Price Change! Reduced by $94,000 down 14% on May 26th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2400  |  Acres: 1.86
Friday Aug 22, 2025
Description: Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances. The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious additional bedrooms and a well-appointed shared bathroom. An attached two-car garage provides easy access and ample storage. Enjoy the outdoors from your covered front porch or in the nicely sized backyard. Perfectly situated for year-round enjoyment, you're minutes from Magic, Stratton, Bromley, and Okemo ski resorts, Lowell Lake plus charming towns like Weston, Grafton, Chester, and Manchester for dining and entertainment. New construction is rare - seize this special opportunity! Call today for a private tour. See MLS Property & Listing Details & 38 images. Includes a Virtual Tour

$799,000 $300 per sq.ft. Windham VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3992  |  Acres: 17.1
Friday May 1, 2026
Description: Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A dedicated entry drop zone keeps gear organized after long days outdoors. The layout offers strong separation of space across three levels, including an en-suite primary, additional bedrooms, and a top-floor loft ideal for overflow sleeping or a recreation zone. The lower level adds a second living area with a wood-burning stove, plus guest accommodations. Outdoor living is equally dialed in, with an upper deck featuring a brand-new hot tub, a newly built firepit, and a natural landscape that includes meadow, stream, and wooded acreage. A three-car garage adds practical year-round convenience. Located within a 20-minute drive to Stratton, Magic, and Bromley, and directly adjacent to the VAST snowmobile trail system, this property offers immediate access to Vermont's top winter and summer activities. See MLS Property & Listing Details & 51 images. Includes a Virtual Tour

$329,000 $154 per sq.ft. Windsor VT Home »

Price Change! Reduced by $10,000 down 3% on April 29th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2142  |  Acres: 0.25
Friday Apr 3, 2026
Description: Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living and entertaining. A main-level bedroom and full bath, along with convenient first-floor laundry, offer ideal single-level living options or guest accommodations. Upstairs, you'll find three generously sized bedrooms, providing plenty of space for family, guests, or a home office setup. Set on a quarter-acre lot, the property offers ample parking and a detached one-car garage, perfect for storage, hobbies, or a workshop. Centrally located and easy access to town, grab your morning coffee just a short walk away or head to the nearby pond for a relaxing swim. A wonderful opportunity to own a well-located home with space, charm, and versatility in Windsor! See MLS Property & Listing Details & 25 images.

$413,900 $143 per sq.ft. Windsor VT Home »

Price Change! Reduced by $10,100 down 2% on April 28th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2888  |  Acres: 1.22
Tuesday Mar 24, 2026
Description: Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship -- and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of mind of updated electrical and heating systems, and the curb appeal of a classic standing seam roof and fresh paint throughout. Recent windows flood the interior with natural light while preserving the home's timeless character. Whether you're drawn by the historic details or the practical updates, this property is move-in ready from day one. The kitchen is showstopping with a seamless blend repurposed materials. It exudes character and charm. The attached 1 car garage -- complete with a dedicated storage room/workshop area and a massive open attic accessible from both levels -- offers flexible space for a workshop, studio, or expansion. A property of this age rarely offers this much functional square footage. Positioned conveniently off Exit 9, commuting to the Upper Valley and beyond is effortless. The commercial zoning potential makes this an exceptional opportunity for buyers seeking a live-work arrangement, professional office space, or a savvy investment in one of Vermont's most storied small towns. Historic character. Modern comfort. Extraordinary potential. See MLS Property & Listing Details & 38 images.

$515,000 $104 per sq.ft. Windsor VT Home »

Price Change! Reduced by $20,000 down 4% on June 11th 2026
6 Beds | 4 Baths |   Total Sq. Ft. 4933  |  Acres: 0.48
Wednesday May 13, 2026
Description: Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch or enjoy the private yard and great family room that overlook the nearby pond providing a peaceful retreat at the end of a long day! See MLS Property & Listing Details & 36 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.

$575,000 $479 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2400  |  Acres: 4.48
Wednesday Mar 11, 2026
Description: Perched to capture breathtaking long-range views, this striking ski home offers an unforgettable vantage point of Magic Mountain and Stratton, with Bromley visible to the northwest--a daily reminder that some of Southern Vermont's best skiing and outdoor adventure are just minutes away. With its cool, modern vibe and classic alpine character, the home perfectly blends style, comfort, and mountain living. The main living area is designed to showcase the spectacular scenery, with large windows that frame the surrounding mountains and fill the space with natural light. A wood-burning fireplace anchors the living room, creating the perfect spot to gather after a day on the slopes. Clean architectural lines, warm materials, and thoughtful updates give the home a contemporary yet welcoming feel throughout. Several upgrades and renovations provide comfort and efficiency for years to come. The property also includes a carport, providing convenient covered parking so you won't have to clear snow off your car after a Vermont snowfall, along with space for skis and all the gear that comes with an active mountain lifestyle. Perfectly located just minutes from Bromley Mountain and a short drive to Stratton Resort, this home is ideally positioned for year-round recreation--from skiing and snowboarding in winter to hiking, biking, and golf in the warmer months. An added benefit of this property, if you opt to join, is that a Bromley Bond is available, providing driveway plowing, and garbage pickup services. Whether you are seeking a full-time residence or a retreat, this unique mountain home offers style, views, and an unbeatable Southern Vermont location. Closing to occur on or after June 15. The buyer may elect to close earlier and allow the seller to rent the property back until June 15. This property will transfer unfurnished. See MLS Property & Listing Details & 37 images.

$729,000 $355 per sq.ft. Winhall VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2055  |  Acres: 1.02
Monday May 4, 2026
Description: Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont! This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just minutes away and a weekend/holiday shuttle to the mountain, your getaway is as convenient as it is memorable. But the fun doesnt stop when the snow melts! During the warmer months, guests can enjoy a variety of outdoor activities at the nearby recreation area , including tennis, pickleball, a swimming pond, picnic tables, and grills perfect for summer cookouts. Whether you're hitting the slopes, hiking trails, or enjoying a sunny afternoon by the pond, Gone Ski Inn is your ideal year-round escape for family, friends, and unforgettable memories. Make this your Vermont Home! See MLS Property & Listing Details & 28 images. Includes a Virtual Tour

$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.