$479,000 $316 per sq.ft. Pittsfield VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1518  |  Acres: 1.8
Sunday Aug 16, 2026
Description: Nestled among the woods of Pittsfield's coveted Townsend Brook area, this beautifully maintained and thoughtfully updated chalet captures the essence of the quintessential Vermont mountain getaway. Designed in the tradition of a European alpine chalet, the main living level occupies the second floor, maximizing natural light and creating a warm, inviting space for après-ski gatherings or quiet evenings by the fire. Recent improvements include an upper-level bump-out with a charming reading nook and convenient powder room, beautiful maple hardwood floors, modern lighting and ceiling fans, and beautifully remodeled bathrooms. An enclosed former storage shed has been transformed into a generous mudroom and first-floor laundry, complete with a wall of built-in cabinetry for skis, bikes, boots, and outdoor gear. A spacious wraparound deck extends the living space outdoors, offering both sunny and shaded spots for morning coffee, al fresco dining, or gathering with friends. Surrounded by the Green Mountains, miles of mountain biking and snowmobile trails are practically at your doorstep, while world-class skiing at Killington and Pico is just minutes away. With easy access from Montreal, Boston, and New York City, this turnkey retreat offers an appealing combination of comfort, recreation, and value - equally suited to weekend escapes, investment income, or year-round living. See MLS Property & Listing Details & 39 images. Includes a Virtual Tour

$745,000 $366 per sq.ft. Pittsfield VT Home »

Waterfront on Pond
3 Beds | 2 Baths |   Total Sq. Ft. 2034  |  Acres: 54.4
Friday Jun 26, 2026
Description: Tucked away at the end of Upper Michigan Road on 54.4 private acres bordering the Green Mountain National Forest, this remarkable 1825 Vermont farmhouse offers breathtaking long-range mountain views in an unforgettable setting. Rich in authentic character, the home showcases rustic knotty pine walls, exposed hand-hewn beams, wide plank floors, and a fieldstone fireplace hearth. The home's low ceilings and gently uneven floors are not imperfections -- they are reminders of a time when homes were built by hand and meant to last. A thoughtfully designed addition in 1996 blends seamlessly with the original home, providing modern comfort with a spacious primary bedroom featuring 10-foot ceilings and custom built-ins, a guest bedroom, and a beautifully updated full bath. The expansive living area offers inviting spaces to gather around the woodstove, enjoy movie nights, or relax with family and friends. The vintage-inspired kitchen and dining area, with vaulted ceilings, warm pine finishes, and a picnic-style dining table, is ideal for casual entertaining. Upstairs, two additional guest bedrooms and a powder room provide comfortable accommodations. Outside, more than 30 acres of managed woodland extend along both sides of the town road, complemented by open lawns, mature perennial gardens, and endless opportunities to enjoy the spectacular southern views. A detached two-car garage with overhead storage provides ample space for vehicles and outdoor gear. Snowmobiling, ATV riding, hiking, mountain biking, and snowshoeing are all accessible directly from the property. A state wastewater permit for an additional three-bedroom home offers exceptional flexibility for future expansion or a family compound. This is a rare opportunity to own a legacy Vermont property where history, privacy, recreation, and extraordinary natural beauty come together. See MLS Property & Listing Details & 55 images. Includes a Virtual Tour

$899,900 $336 per sq.ft. Pittsfield VT Home »

Price Change! Reduced by $50,100 down 6% on August 30th 2026
3 Beds | 4 Baths |   Total Sq. Ft. 3807  |  Acres: 3.82
Tuesday Jun 2, 2026
Description: Located just minutes from the Killington Access Road, 91 Bombadil Path offers the perfect blend of convenience, quality, square footage and comfort. This one owner, well maintained home offers easy access to the VAST trail. Situated on 3.84 acres this Cape presents easy to maintain gardens with mature perennial plants and a patio great for entertaining around the firepit. Park your vehicles in the attached, oversized garage which also includes overhead storage. Enter the home into a dedicated mudroom. If cooking is your thing you will love the natural light in the open concept kitchen featuring stainless steel appliances. Enjoy coffee or apres in the 3 season sun porch. Relax in the spacious living room by the gas fireplace offering calming ambience. The generously sized primary suite complete with walk in closet, a 2 sink countertop, soaking tub and seperate shower is the perfect place to retreat to at the end of an adventurous day. The laundry room consists of a full sized washer and dryer, built in wall ironing board and wash sink, making laundry a breeze. Upstairs you will find 2 large bedrooms (one with a huge walk-in closet) and a full bathroom. Both bedrooms offer plenty of space to work or study from home. Downstairs you will find a finished oasis offering a living room, bathroom, bar and an additional sleeping space. This area has its own entrance making it a perfect in-law suite or rental apartment. Downstairs you will also find a craft room, tool/ski tuning room, and plenty of storage space. Located just minutes to Killington, Pittsfield offers their students school choice, making this home even more desirable. Store your equipment, whether it is for gardening, snowmobiling or skiing in one of the 2 sheds. With plenty of parking, this home is perfect for a primary residence, a vacation home or an investment opportunity. Located on a cul-de-sac, this home offers beautiful winter mountain views. Near skiing, snowmobiling and hiking. Paradise awaits. See MLS Property & Listing Details & 60 images.

$249,500 $152 per sq.ft. Pittsford VT Home »

Price Change! Reduced by $10,000 down 4% on August 10th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1640  |  Acres: 0.38
Tuesday Jun 30, 2026
Description: Classic Vermont charm meets everyday comfort in this inviting Pittsford Village home, where original character, thoughtful updates, and a spacious backyard come together at an exceptional value. A welcoming covered front porch offers the perfect place to enjoy your morning coffee or unwind after a busy day. Step inside to discover original hardwood floors that add warmth and timeless appeal throughout much of the home. The comfortable living room is centered around a cozy wood stove, creating an inviting atmosphere during Vermont's colder months. The eat-in kitchen and formal dining room provide flexibility for both everyday living and entertaining, while a full bath with first-floor laundry adds convenience. Upstairs, three comfortable bedrooms and a second full bath offer space for family, guests, or a home office. The .38-acre lot features a spacious backyard with room for gardening, pets, play, or outdoor gatherings. Replacement windows, low-maintenance vinyl siding, and a standing-seam metal roof provide lasting durability and reduced maintenance. A detached garage and ample driveway parking complete the property. Ideally located in the heart of Pittsford Village, you'll enjoy walking to the Pittsford Recreation Area and Lothrop Elementary School, with local shops and amenities just minutes away. Rutland is only 15 minutes away, and Burlington International Airport is less than 90 minutes from home. Blending character, functionality, and value, this home offers an opportunity that's becoming increasingly difficult to find in today's market. Sale is subject to the sellers securing suitable housing. Relocation options have been identified, and a flexible closing timeline is available. See MLS Property & Listing Details & 28 images.

$262,000 $173 per sq.ft. Pittsford VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1512  |  Acres: 1.2
Wednesday Jul 15, 2026
Description: Come see 5190 Whipple Hollow Road and discover your opportunity to own a beautiful Vermont country retreat at an attractive price. If you've been waiting for the right home, the time to see this one is now! Open House: Saturday, September 5th, 2026 from 12pm-1pm. Set on a picturesque country lot, this inviting, move-in-ready property offers the perfect blend of comfort, privacy, and Vermont charm. The open and airy floor plan is filled with natural light, while the updated kitchen flows seamlessly into the dining and living areas--perfect for entertaining or simply enjoying everyday life. Step outside onto the wrap-around deck overlooking the beautiful yard, an ideal setting for morning coffee, summer gatherings, and relaxing evenings surrounded by nature. All improvements made since 2023 include a brand new kitchen, plus both the primary and secondary bathrooms, updated light fixtures, new appliances, updated exterior doors, fresh paint, new flooring, and a new septic tank replaced in August, 2026. A new oil tank, plus all mechanics of the home have 2026 annual service tags. Whether you're searching for your first home, a peaceful getaway, or a place to enjoy everything Vermont has to offer, this property delivers country living with convenient access to Rutland, skiing, golf, lakes, hiking, and year-round outdoor recreation. OPEN HOUSE -- COME TAKE A LOOK BEFORE IT'S GONE! With an attractive price and so many recent updates, this is an opportunity you won't want to miss. Come see it, fall in love with the setting, make your offer, and move in before the last of the foliage falls! See MLS Property & Listing Details & 55 images. Includes a Virtual Tour

$290,000 $164 per sq.ft. Pittsford VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1764  |  Acres: 0.73
Wednesday Jul 22, 2026
Description: This private and serene three bedroom, furnished country get-away is located in Pittsford but just minutes to the Chittenden Reservoir and Killington/Pico down hill skiing. The open living room with a dining area greets you at the front door. There is an efficient kitchen with ample counterspace and oak cabinets conveniently located just off the dining area. The first floor has a charming step-down sunroom that provides extra living space for family and friends with a sliding glass door for extra sun light and easy access to the garden. There is a full bathroom and laundry/mudroom area with a door leading to the large covered back porch. From here you can entertain in style or just relax while listening to the babbling brook that passes between the house and back garden paths. The stairway to the second level has a generous landing area with three bedrooms off of it. The primary bedroom has a full bathroom with a dressing room that is currently being used as an office. From here you have the luxury of sitting on the second story partially covered porch with an open balcony for sunbathing in the summer and warmer winter days! There is a yard with a patio and paths with bridges to cross the brook as you make your way to the separate parcel of .27 acres of land behind the house. A peaceful location just minutes to recreation, the Mountain Top Inn and Rutland shopping. See MLS Property & Listing Details & 47 images.

$350,000 $306 per sq.ft. Pittsford VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2288  |  Acres: 5.7
Tuesday Aug 4, 2026
Description: Set on 5.7 acres with mountain views, this well-maintained home sits nicely above the sprawling property, with a terrific front deck that's the perfect spot to sit back, take it all in, and enjoy the sunsets. Inside, you'll find hardwood floors, a comfortable living room with fireplace, and the convenience of an attached garage. A 16' x 32' shed with electricity makes a great workshop or provides plenty of additional storage. There's ample room for gardening, with established gardens in place, while the basement offers additional space for a rec room, storage, or casual hangout area. Two separate portions of the property offer frontage along Route 7, with potential for subdivision. Just up the road from Proctor-Pittsford Golf Course and Pico & Killington Ski Areas, with Rutland less than 15 minutes to the south and Brandon just minutes to the north! See MLS Property & Listing Details & 59 images.

$524,600 $244 per sq.ft. Pittsford VT Home »

Price Change! Reduced by $24,400 down 5% on July 14th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2148  |  Acres: 1.3
Wednesday Jun 17, 2026
Description: Set along desirable Orchard Hill in Pittsford, this distinctive Tudor-inspired home offers timeless curb appeal, comfortable living space, and a beautiful 1.3-acre setting. The exterior blends brick, stucco-style accents, dark trim, mature landscaping, and a welcoming front entry, creating a property with warmth and character from the moment you arrive. Inside, the home features an inviting kitchen with abundant cabinetry, generous counter space, stainless appliances, a gas range, and a charming windowed sink area overlooking the backyard. The floor plan provides comfortable everyday living, with 3 bedrooms, 3 baths, and approximately 2,070 sq. ft. of space. The expansive primary bedroom boast a large sitting area that would be great space for a quite sitting area, an exercise space or an office and an enormous walk-in closet. Add to that a bath which offers dual vanities, an oversized walk-in tiled shower and a relaxing jetted shower panel. Outside, you will enjoy both a sun-drenched side porch that extends the already spacious living room as well as a rear deck with access to the back yard and fenced in area. This space is ideal for relaxing, entertaining, pets, or gardening. An attached 2-car garage adds convenience, while the Pittsford location offers a peaceful residential feel with easy access to Rutland, Brandon, area recreation, schools, and local amenities. A wonderful opportunity to own a character-filled Vermont home in a well-established neighborhood. Welcome home! See MLS Property & Listing Details & 42 images. Includes a Virtual Tour

$425,000 $316 per sq.ft. Plainfield VT Home »

Price Change! Reduced by $25,000 down 6% on August 13th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2044  |  Acres: 1.83
Thursday Jul 2, 2026
Description: The long distance mountain and sunset views from this home are truly extraordinary. Sit on your deck and watch the weather come across the valley as the sun sets over Camel's Hump. 3 bedroom ranch with 2 car attached, insulated garage and walk-out basement with separate exterior entry and partial kitchen that could be rental or in-law apartment. Owned Solar Photovoltaic array brings electric bill down to close to zero. Hardwood floors throughout main floor. Primary bedroom with en-suite bath and walk-in closet. Wood stove in LR serves as supplemental or primary heat source. Paved level driveway and car parking with basketball hoop set up. Oversized insulated 2 car garage was previously used as blacksmith shop with additional car port attached. High speed internet from Spectrum. Lot is very private and on a quiet country road yet located only 2 minutes to Plainfield village and 20 minutes to Montpelier or Barre. Come take a look at this country ranch home with incredible mountain views. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$599,900 $244 per sq.ft. Plainfield VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2457  |  Acres: 10.1
Tuesday Jul 14, 2026
Description: Quintessential Vermont Farmhouse on 10.1 Acres with sweeping pastoral and mountain views. Blending historic character with modern flexibility, this exceptional property offers ample space, 3 bedrooms, 2½ baths, and a floor plan designed to adapt to the way you live. At the heart of the home is a spacious open-concept Kitchen/dining area that flows effortlessly for everyday living and entertaining, including a full bathroom with sauna. Spacious living room and office open to a back patio. Apart from the main living area is a semi-finished light and bright multi-use space, perfect as an artist's studio, gathering space, or recreation room. The home's flexible layout includes two separate living suites. A second kitchen has been converted to an office. The configuration also offers the potential to convert back to two residential units if desired. Outside, the property is a dream for hobby farmers, equestrians, entrepreneurs, and anyone seeking space to create. Multiple barns provide incredible versatility. The studio barn features garage parking below with finished studio or office space above. A second barn with direct access to pasture is perfectly suited for horses, livestock, or other farm animals. Across the road, the historic main barn built with English Tyne joinery offers exceptional space for entertaining, events, workshops, agricultural ventures, or storage. Frost-free farm and barn water spigots throughout the property. Whether you're dreaming of a working farm, equestrian property, family homestead, artist's retreat, or simply a peaceful Vermont escape surrounded by spectacular scenery, this remarkable property offers the rare combination of historic charm, functional outbuildings, flexible living spaces, and boundless potential. Here, Vermont's iconic landscape becomes your everyday view, and the possibilities are limited only by your imagination. See MLS Property & Listing Details & 60 images.

$450,000 $611 per sq.ft. Plymouth VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1276  |  Acres: 1.73
Thursday Jul 30, 2026
Description: Tucked away on a quiet road in Hawk Resort, this charming 3-bedroom, 2-bath mountain retreat offers privacy, warmth, and easy access to Vermont's best four-season recreation. Just under 1,300 square feet, the home is thoughtfully designed to make the most of its inviting spaces, with random-width pine floors, a classic fieldstone fireplace, and abundant windows that bring in natural light and views of the surrounding woods. The open living area flows to a spacious deck, creating the perfect setting for morning coffee, evening gatherings, or simply enjoying the peaceful natural surroundings. Ideally located halfway between Killington Resort and Okemo Mountain Resort, you'll enjoy convenient access to skiing, golf, hiking, mountain biking, and endless outdoor adventure. Nearby lakes offer swimming, kayaking, and fishing, while the charming village of Woodstock is just 30 minutes away for shopping, dining, and exploring. Showings start 8/4. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$475,000 $363 per sq.ft. Plymouth VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1308  |  Acres: 1.09
Friday Jun 12, 2026
Description: Tucked within the Hawk community, this charming mountain retreat offers the perfect blend of privacy, recreation, and convenience. Set within a private 1.09-acre wooded lot, owners are also able to enjoy access to Hawk's common land with room to explore, including trails ideal for snowshoeing, hiking, and cross-country skiing. Perfectly positioned between Killington and Okemo Mountain, and just minutes to area lakes and scenic Route 100, this location is ideal for year-round Vermont living and exploring. Inside, the open kitchen, dining, and living area is filled with natural light from large windows that frame the peaceful wooded setting. A beautiful stone fireplace with a wood stove insert creates a warm and inviting focal point, perfect after a day on the slopes or trails. The dining area opens to a spacious deck, offering an easy transition to outdoor living and quiet moments surrounded by nature. The lower level features three bedrooms, including charming built-in storage and built-in bunks that make this a fun and functional escape for younger guests. Whether used as a vacation getaway, ski retreat, or four-season home base, this Hawk property captures the relaxed mountain lifestyle in a setting that feels wonderfully private while remaining close to everything the Okemo Valley and Killington region have to offer. Visit the Okemo real estate community today. Taxes are based on current town assessment. See MLS Property & Listing Details & 56 images.

$479,000 $394 per sq.ft. Plymouth VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1824  |  Acres: 2.43
Thursday Aug 20, 2026
Description: Nestled in the woods of Hawk Resort, this inviting three-bedroom, two-bath home offers privacy, comfort, and easy access to everything the Okemo Valley has to offer. The cozy main-level living area features a fireplace and direct access to a private deck, while the spacious dining area captures peaceful wooded views. The nicely appointed kitchen provides plenty of cabinet and counter space. The private ensuite primary bedroom features a mini-split and an updated bath. A second bedroom, also with a mini-split, is located on the mid-level with an adjoining updated 3/4 bath. The lower level offers a versatile entertaining space with endless possibilities, family room, game room, office, or additional gathering space, along with a third bedroom perfect for guests or kids. Additional features include a newer stackable washer/dryer and plenty of room to relax and enjoy the surrounding woods. Ideally located along Scenic Route 100 between Okemo and Killington Ski Resorts, this is a wonderful four-season Vermont getaway or year-round home. See MLS Property & Listing Details & 47 images.

$299,000 $150 per sq.ft. Pomfret VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1988  |  Acres: 8
Tuesday Aug 25, 2026
Description: Charming One-Level Living on 8 Acres Near Woodstock Tucked just off a paved road above the White River, this single-level home offers an ideal location with easy access to the entire Upper Valley. You're minutes from Saskadena Six ski area (formerly Suicide Six), the farm-to-table dining at Cloudland Farm, and the classic Teago General Store in South Pomfret with the picturesque Village of Woodstock just a short drive away. Inside, original hardwood floors and abundant natural light give the home warmth and character. The spacious family room centers around a wood-burning brick fireplace, while the formal dining room features a cozy gas stove, perfect for chilly Vermont evenings. The eat-in kitchen makes everyday living easy, and a generous deck extends your living space outdoors, ready for summer entertaining. Downstairs, the walk-out lower level offers exciting potential: finish it as a home office, workshop, or studio to suit your needs. All of this on 8 acres of Vermont countryside, in a location that puts the best of the region within easy reach: skiing and mountain biking, swimming and fishing on the White River, the shops and restaurants of Woodstock Village, Billings Farm & Museum, and the trails of Marsh-Billings-Rockefeller National Historical Park. Hanover, Dartmouth Health, and I-89 are all within an easy commute. See MLS Property & Listing Details & 17 images.

$518,900 $315 per sq.ft. Pomfret VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1648  |  Acres: 2
Monday Aug 10, 2026
Description: Set along scenic Pomfret Road, 8133 Pomfret Road offers the charm and character of a classic Vermont farmhouse in the heart of Pomfret. This 3-bedroom, 2-bath home, originally built in 1875, is situated on approximately 2 acres and features exposed beams, wood floors, and a woodstove that adds warmth and character to the living space. A screened-in porch steps out to a beautiful stone patio with a propane fire table, creating an inviting place to relax, entertain, and enjoy the peaceful Vermont surroundings. Outside, thoughtful landscaping, established gardens, fruit trees, maple trees, and a chicken coop offer a touch of Vermont homesteading, with the opportunity to tap your own trees and enjoy making maple syrup for family and friends. A workshop provides valuable space for projects, hobbies, or additional storage, while the attached garage adds everyday convenience. Membership in a community solar array and efficiency upgrades brings an energy-conscious element to this historic property. Blending period character with comfortable living spaces, inviting outdoor areas, and opportunities for gardening and homesteading, the property is well suited for year-round living or a Vermont country retreat in one of the area's most picturesque communities. See MLS Property & Listing Details & 33 images.