$1,275,000 $227 per sq.ft. West Rutland VT Home »

Waterfront on Pond
6 Beds | 6 Baths |   Total Sq. Ft. 5616  |  Acres: 105.7
Wednesday Jul 8, 2026
Description: Set on approximately 105 acres of picturesque Vermont countryside, this extraordinary property offers exceptional privacy, natural beauty, and the rare advantage of two separate homes--perfectly suited for a primary residence with an entertaining guest house, multi-generational living, or short-term rental opportunity. This one-of-a-kind offering provides space, comfort, and endless four-season recreational potential. The main home is filled with natural light, highlighted by expansive windows that frame the surrounding landscape. Thoughtfully designed for both everyday living and hosting, it features two bedrooms, two and a half baths, and a dedicated office space ideal for remote work. Two inviting living rooms create flexible gathering spaces, while the fully equipped kitchen serves as the heart of the home. Rooftop access offers a unique vantage point to take in sweeping countryside views, and central air ensures year-round comfort. The second home functions beautifully as an entertaining guest house, offering four bedrooms, two and a half baths, an additional kitchen and living room designed for hosting family and friends. A bonus room provides even more versatility for recreation, a game room, gym, or studio. Below the homes, a substantial four-bay garage offers abundant storage for vehicles, outdoor equipment, and seasonal gear. The land itself is a private playground, complete with a pond and expansive acreage to create trails for hiking, snowshoeing, or ATV riding. Enjoy sledding in winter, wildlife watching, and peaceful seclusion in every season. Ideally located near Pico Mountain, Killington Resort, and Okemo Mountain Resort, as well as the charming town of Manchester, the property is approximately three hours to Boston and four and a half hours to New York City. A rare opportunity to own a truly special Vermont retreat offering both lifestyle and investment appeal. See MLS Property & Listing Details & 59 images.

$589,000 $276 per sq.ft. West Windsor VT Home »

Price Change! Reduced by $56,000 down 10% on July 30th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2515  |  Acres: 10.27
Thursday Jul 9, 2026
Description: Quietly sited off a private secluded road, sits a finely hand-crafted family home and outbuildings on 10.27 acres. The lot features an open yard, gardens, stone walls, woodland trails & nearby brooks. The main house features post and beam construction with sweeping cathedral ceilings, 2 bedrooms, 1.5 baths, a loft, finished lower level, and many custom-built features. The kitchen is well appointed with custom cabinetry and stone counters. A stand-out bonus feature comprises a detached 2 bedroom in-law or rental apartment above an 1150 sq. foot office/woodworking shop prefect for hobbies or a commercial home business. This property is perfectly sited in close proximity to State Forest for hiking, biking trails on Mt Ascutney, easy access to Interstate 91, Woodstock VT, Hanover NH, Dartmouth, and all recreation. See MLS Property & Listing Details & 35 images.

$699,500 $331 per sq.ft. West Windsor VT Home »

Price Change! Reduced by $50,000 down 7% on August 20th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2112  |  Acres: 5.01
Wednesday Jul 29, 2026
Description: Welcome to The Rock House! A beautiful hillside retreat set on a private, lush landscape with captivating views of Mount Ascutney. The home's spectacular great room is the heart of the property, featuring soaring cathedral ceilings, rich hardwood floors, a dramatic floor to ceiling stone fireplace, and walls of windows that flood the space with natural light while showcasing the breathtaking mountain vistas. Thoughtfully designed for both comfortable everyday living and effortless entertaining, this inviting gathering space perfectly captures the warmth, character, and natural beauty that make the Rock House so special. The beautifully updated kitchen features quartz countertops, quality cabinetry, and an efficient layout that makes meal preparation both functional and enjoyable. The spacious main-level primary suite offers a peaceful retreat, complete with an attached sunroom featuring radiant floor heat, an ideal spot to relax year-round while taking in the surrounding landscape. Two additional bedrooms and a three-quarter bath complete the main level, providing comfortable accommodations for family and guests. Privately tucked away on the upper level, an additional ensuite bedroom offers flexibility as a guest suite, home office, or secluded retreat. The exterior is landscaped with two stone patios and level lawn area with fire pit seating area perfect for relaxing and entertaining. Modern comforts and energy efficiency abound with mini-splits, new furnace, solar array, tesla battery, and heated two car garage. Combining timeless architectural appeal with thoughtful updates and an exceptional setting, The Rock House offers a rare opportunity to enjoy Vermont living at its finest.Take in multi-seasonal recreation and the arts just minutes away at Ascutney Outdoors and Brownsville Butcher & Pantry for some terrific local dining. Easy access to Woodstock, Killington and Okemo. Showings to begin at the See MLS Property & Listing Details & 37 images.

$775,000 $245 per sq.ft. West Windsor VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3168  |  Acres: 2.5
Tuesday Jul 7, 2026
Description: Located in the heart of Sheddsville-West Windsor's earliest settlement, this lovingly stewarded historic Greek Revival Farmhouse imbues the true character of the Vermont vernacular. Improved over the centuries to accommodate modern living, all while preserving the the period detail and charm with original pine plank floors, 6/6 sash windows and hewn beams. The home was well built of solid and sound plank construction, providing insulation throughout. The beautiful Great Room addition is anchored by a handsome wood burning fireplace with custom cherry mantel, and connects to the exterior spaces through French doors stepping out to a covered porch and a spacious deck overlooking a sweeping level lawn, mature maple trees, established perennial beds, and a firepit at the edge of a four-season stream. Open concept eat in kitchen with farmer sink and butcher block counters, formal dining room, library- TV room, study with a half bathroom. Two mudrooms complete the main level. Moving upstairs, there's a generous primary bedroom ensuite with a wood stove, a laundry room, three additional bedrooms and a shared bathroom. Leased Tesla back up battery provides peace of mind in the event of a power outage. The ample three-bay barn can be used as parking, equipment storage, workshop, or for farm animals. Extensive dirt road, and trail systems (ideal for equine interests, hiking, cycling) are just out side your door. Easy access to all recreation, Interstate, Woodstock, Hanover NH. 2.25 Hours to Boston. 4.5 hours to NYC. Showings begin with an Open House on Saturday July 11 from 11:00 to 12:30 See MLS Property & Listing Details & 42 images. Includes a Virtual Tour

$1,295,000 $255 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »

Price Change! Reduced by $50,000 down 4% on August 6th 2026
7 Beds | 6 Baths |   Total Sq. Ft. 5774  |  Acres: 5.51
Wednesday Jun 3, 2026
Description: With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone. The newer addition features an open concept kitchen, dining, and living area anchored by a custom stone fireplace and dramatic floor to ceiling windows framing the mountain views. A sun-filled deck invites morning coffee, summer entertaining, or cozy après ski evenings. The primary suite is a private retreat with its own deck, ensuite bath, walk in closet, and dedicated office. The original wing offers four additional bedrooms, a kitchen, living area, and its own deck, creating an ideal space for guests or extended family. Whether enjoyed as one expansive residence, configured for private guest accommodations, or explored for its income-producing rental potential, the flexible layout adapts to a variety of lifestyles. Located in the heart of Brownsville. Just minutes from Mount Ascutney's trails and outdoor recreation, and within easy reach of Woodstock, Okemo, Killington, and the Upper Valley, this is a rare opportunity to own a true Vermont retreat where unforgettable memories are made all year long, with the added flexibility of potential rental income when you're away. See MLS Property & Listing Details & 32 images. Includes a Virtual Tour

$1,325,000 $519 per sq.ft. West Windsor VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2554  |  Acres: 26.72
Wednesday Apr 29, 2026
Description: Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows--often even double rainbows--across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms--two conveniently located on the first floor. Wide pine and maple floors run throughout, adding classic farmhouse character. The equestrian amenities are outstanding: a 3,024-square-foot stable with seven spacious stalls, a heated tack room, wash stall, bathroom, and laundry area. The 100' x 200' riding arena features a state-of-the-art, eco-friendly footing made from recycled sneakers, offering outstanding drainage, low dust, and excellent footing. Outdoor facilities also included are a round pen, four grass paddocks, and one dirt paddock. Quiet gravel roads invite walking and riding, with access to the Green Mountain Horse Association trail system. A stream winds along the property's West border, while apple and pear trees provide seasonal bounty. High-speed internet ensures fast connectivity. Ascutney Outdoors, with 40 miles of trails for horseback riding, mountain biking, skiing, and hiking, is nearby, and the popular Brownsville Butcher and Pantry is less than two miles away. (Horses not included) See MLS Property & Listing Details & 46 images. Includes a Virtual Tour

$3,150,000 $981 per sq.ft. West Windsor VT Home »

Price Change! Reduced by $200,000 down 6% on August 12th 2026
Waterfront on Pond _Unnamed
5 Beds | 5 Baths |   Total Sq. Ft. 3212  |  Acres: 98
Wednesday Apr 15, 2026
Description: Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartzite island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroom with slate floor, more than an entry it's a nice transitional space to enjoy, 3 BR/3 BA and a Sitting area on the 2nd floor with a tranquil view of the back fields. 2 additional BRs and a half bath on the 3rd floor. All new wiring, plumbing, new Bosch propane furnace supplies radiant heat, triple pane, Anderson low-E4 windows, sheetrock, DaVinci slate-like rubber roof & cherry floors. Fully insulated, extremely efficient. Custom built trim, wide baseboards, wainscoting & cabinets. 200+ year old pine boards from the house were used to craft bathroom vanities, 3rd floor stairs & beautiful doors. Outdoor amenities include in ground pool, gardens & lovely stone patio. A large-3600 sq ft former dairy barn with new wiring & FHA furnace & oil tank. Now used as a garage, workshop & abundant storage space offers ENDLESS possibilities! See MLS Property & Listing Details & 60 images.

$498,750 $153 per sq.ft. Westminster VT Home »

Price Change! Reduced by $46,250 down 9% on July 31st 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3263  |  Acres: 1.3
Friday May 8, 2026
Description: Welcome to this spacious contemporary home located on the desirable Hartley Hill Road, conveniently situated near Saxtons River, Bellows Falls, Putney, and I-91. Built in 2008, this well-maintained home offers quality craftsmanship including a brand new roof installed April 2026, high-end utilities, and modern comforts throughout. The finished, walk-out lower level features radiant heat, abundant natural light, and exterior access from three sides of the home. This floor is home to the spacious primary suite including a luxurious ensuite bathroom complete with a soaking tub, dual sinks, a beautiful walk-in shower, separate toilet room, and a large walk-in closet. This level also offers a generous bonus room, laundry room, and utility room. Upstairs, enter through the back deck into a welcoming entryway leading to the expansive modern kitchen, featuring granite countertops, a large center island with pendant lighting, and plenty of space for entertaining. The open-concept kitchen, dining, and living area is centered around a striking staircase that ties the space together beautifully. This level also includes an additional bedroom and a convenient half bath. The upper floor offers two more spacious bedrooms and a full bathroom with dual sinks and a walk-in shower. Outside, relax on the deck overlooking the pool while enjoying the privacy and tranquility of the surrounding rural countryside. See MLS Property & Listing Details & 54 images.

$579,000 $279 per sq.ft. Weston VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2077  |  Acres: 0.66
Sunday Jun 7, 2026
Description: 639 Main Street, Weston, Vermont Offered at $579,000 A rare opportunity to own a turnkey home in the heart of picturesque Weston Village. This beautifully renovated four-bedroom, two-bath residence offers the perfect blend of walkable village living, natural surroundings, and timeless Vermont charm. Built in 1952, this thoughtfully updated 2,077-square-foot home sits on 0.66 acres on an elevated village lot overlooking the woods, with the soothing sounds of the nearby West River. The property offers the best of both worlds: a peaceful, scenic setting just steps from Weston's beloved restaurants, cafés, theater, country store, and charming village shops. Inside, the home has been extensively renovated, seamlessly blending classic Vermont character with modern comfort. A stunning open-concept kitchen featuring StoneHill Cabinetry serves as the centerpiece of the main living area. A cozy breakfast nook overlooking the backyard provides the perfect spot to enjoy your morning coffee. Additional updates include two fully renovated bathrooms, newly installed oak hardwood flooring throughout the first floor, custom blinds, fresh interior paint, and all-new trim details. The redesigned mudroom adds both style and functionality. An additional 1,349 square feet of dry, usable basement space offers a laundry area, abundant storage, and convenient walkout access to the parking area, providing exceptional flexibility for hobbies, recreation, or future expansion. Outdoor living is equally inviting, with beautifully maintained flower beds surrounding the home and a newly installed bluestone patio creating an ideal space for relaxation and entertaining. Whether you are seeking a full-time residence or a Vermont getaway, 639 Main Street offers turnkey living in one of Southern Vermont's most desirable historic villages. See MLS Property & Listing Details & 48 images.

$670,000 $144 per sq.ft. Weston VT Home »

Price Change! Reduced by $29,000 down 4% on August 27th 2026
7 Beds | 6 Baths |   Total Sq. Ft. 4642  |  Acres: 0.15
Monday Jul 6, 2026
Description: Perfectly situated in the heart of one of Southern Vermont's most picturesque villages. Just a short drive from Stratton Mountain, Okemo Mountain Resort, Bromley Mountain, and Magic Mountain, this beautifully preserved property offers the ideal combination of historic character and modern comfort. Thoughtfully maintained, the home showcases classic New England architecture with warm pine floors, reclaimed barn wood accents, and abundant natural light throughout. Spacious living and gathering areas make entertaining effortless, while intimate sitting spaces provide the perfect setting to relax after a day of skiing, hiking, or exploring Vermont's scenic countryside. The expansive primary suite is a private retreat featuring tranquil river views, a walk-in closet, dressing room, and a beautifully appointed en-suite bath. Each additional bedroom offers its own dedicated bathroom, creating comfort and privacy for family and guests alike. Outside, enjoy mornings on the front patio overlooking the sounds of the river or spend evenings around the backyard fire pit. Located just a short walk from the Village Green, charming shops, dining, and the acclaimed Weston Playhouse, you'll experience the best of village living while remaining close to Southern Vermont's premier ski resorts, golf courses, hiking trails, and outdoor recreation. This property is a timeless treasure, ready to be cherished by generations to come. See for yourself! See MLS Property & Listing Details & 47 images. Includes a Virtual Tour

$1,199,000 $274 per sq.ft. Weston VT Home »

Price Change! Reduced by $100,000 down 8% on August 10th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 4372  |  Acres: 15.1
Monday May 11, 2026
Description: Sunday 8/16 Open House is being CANCELED! Experience the very best of Vermont living in the charming village of Weston, where every season offers something to enjoy. Spend winter days skiing at nearby Stratton, Magic, Bromley, or Okemo, and warmer months hiking scenic trails, horseback riding, swimming in lakes and ponds, or taking in a performance at the Weston Theater Company. Explore local shops, galleries, and restaurants while enjoying the beauty of one of Southern Vermont's most beloved communities. Whether you're seeking outdoor adventure, a vibrant arts community, or simply the peace and beauty of Vermont, this exceptional property places it all within easy reach. Thoughtfully built and impeccably maintained, this 4 bedroom, 3 bath home reflects exceptional pride of ownership with thoughtful upgrades throughout. Set on a beautifully landscaped property with a private swimming pond, it offers the perfect balance of comfort, privacy, and year round recreation. Designed for gathering, the home features a spacious open kitchen and dining area, inviting living and family rooms, and a generous mudroom ready for skis, hiking boots, and outdoor gear. A first floor den with an adjacent full bath offers flexibility as a guest room or first floor bedroom. Upstairs are four comfortable bedrooms, a dedicated office, and a spacious laundry room. The primary suite is a true retreat with a large walk in closet, oversized bath, soaking tub, and mountain views. A full basement with bulkhead access provides excellent storage and endless potential for a fitness room, workshop, or future finished space. Outside, mature perennial gardens frame the home, while a covered front porch and sun-filled back deck with a hot tub provide the perfect setting to relax and enjoy the mountain views. The private swimming pond completes this exceptional Vermont retreat. See MLS Property & Listing Details & 42 images.

$325,000 $147 per sq.ft. Weybridge VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2214  |  Acres: 1.5
Tuesday Jul 14, 2026
Description: Located at the end of the road, an affordable home with a welcoming front porch and garage awaits. Wood floors in the living areas and a propane stove in the living room for chilly nights. A first-floor office could serve as a bedroom, and a bath with laundry is convenient. Upstairs are four bedrooms and two bathrooms. The one-car garage is extra deep, with a back space for great storage. Located just 4.5 miles from downtown Middlebury for all of the conveniences of town. Close to the trail around Middlebury for great walking and biking trails. Being sold as is. Offer deadline is Friday, July 17th at 3pm. See MLS Property & Listing Details & 32 images.

$695,000 $182 per sq.ft. Weybridge VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 3827  |  Acres: 5.25
Friday Jul 3, 2026
Description: Set on 5.25 picturesque acres offering access to 1,200 acres of Snake Mountain Wildlife Management Area, this beautifully restored farmhouse offers exceptional privacy, timeless character, and breathtaking Green Mountain views. Extensively renovated while preserving its historic charm, the home seamlessly blends classic Vermont architecture with modern comfort. The welcoming foyer opens to sun-filled living spaces featuring hardwood floors, exposed beams, original woodwork, and oversized windows framing spectacular vistas. The updated kitchen is designed for everyday living and entertaining with granite countertops, stainless steel appliances, abundant cabinetry, and an adjoining breakfast area. Multiple gathering spaces provide flexibility for formal entertaining, relaxed evenings, or working from home. The spacious primary suite is a peaceful retreat, while four additional bedrooms offer room for family and guests. Updated baths combine fresh finishes with farmhouse style. A finished lower-level recreation room with wood stove creates the perfect place to gather after hiking, skiing, or exploring the surrounding countryside. Outside, enjoy expansive lawns, mature trees, gardens, and direct access to miles of nearby trails. Whether relaxing on the porch with morning coffee or taking in unforgettable sunsets over the Adirondacks and Green Mountains, every season offers a stunning backdrop. Located just minutes from Middlebury, this remarkable property provides convenient access to shopping, dining, Middlebury College, and area recreation while maintaining the serenity of a private country setting. Rarely does a home offer this combination of acreage, restored character, modern updates, extraordinary views, and immediate access to Vermont's natural beauty. Experience the best of country living in one unforgettable property. Greenhouse included. 1,300 sq ft in-law apartment vaulted ceiling, separate entrance, rentable for income. This is Vermont living at its finest. See MLS Property & Listing Details & 17 images.

$2,875,000 $572 per sq.ft. Weybridge VT Home »

Waterfront on Pond _Unnamed
5 Beds | 5 Baths |   Total Sq. Ft. 5687  |  Acres: 11.5
Wednesday Aug 12, 2026
Description: The Drake House is a rare Vermont landmark, nearly two centuries in the making and thoughtfully carried forward by generations of careful stewards. Built in 1825 by Asaph Drake and his wife, this distinguished brick Federal home has long held an important place in the Middlebury area, with later connections to the Morgan Horse Farm, ownership by a Middlebury College president, and listing on the National Register of Historic Places. Most recently purchased in 2023, the 5,030-square-foot home has been meticulously modernized for contemporary living while preserving the character, craftsmanship, and soul that make it irreplaceable. Light-drenched interiors feature original pumpkin pine floors, historic brickwork, marble accents, reclaimed oak flooring, a restored archway, and elevated updates throughout, including a custom kitchen with coffered ceilings, walnut island, Fisher & Paykel dishwasher, and black enamel AGA propane range. Surrounded by approximately 650 acres of conserved land just five minutes from Middlebury village, the property feels deeply private while remaining closely connected to the landscape, with gardens, a pond, outdoor living spaces, and access to the MALT system's 18-mile trail network. Inside, gracious gathering spaces, a parlor with fireplace and beehive/pizza oven, a serene primary wing with office and cedar sauna, and a wine cellar create a home that is both historic and deeply livable. A post-and-beam barn/garage with guest apartment, additional barn, and second driveway complete this beautifully renewed Federal-era retreat, ready for its next chapter. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$299,000 $117 per sq.ft. Wheelock VT Home »

Waterfront on River Miller Run
4 Beds | 3 Baths |   Total Sq. Ft. 2559  |  Acres: 4
Tuesday May 5, 2026
Description: This lush and level four acre compound along Miller's Run River in Wheelock has more going for it than most properties twice the size. The 2020 Commodore mobile home is the primary residence, with serious mudroom and bedroom additions built for the way Vermonters actually live. With 3 bedrooms and 2 full bathrooms the home feels spacious and full of natural light. Next door a one bedroom guesthouse handles family and friends, or generates rental income with ease. Both homes come simply and elegantly furnished. The newly built 17x32 barn is ready for equipment, livestock, or whatever the next owner has in mind. The insulated 20x42 Quonset hut has power, water, and has previously seen commercial use as a take-out restaurant. Permits are also in place for a third dwelling utilizing existing water and septic. And then there's Miller's Run itself, bordering the entire property with a small rocky cascade before pooling into a deep cold swimming hole that will be the centerpiece of every summer. See MLS Property & Listing Details & 60 images.