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324 Fellows Rd, Pittsfield

Set within 210 acres of unspoiled forestland spanning Killington and Pittsfield, Vermont, The Tweed River Estate is a truly one-of-a-kind property, a private sanctuary where nature and craftsmanship meet. Designed by a renowned architect, the bespoke home is a masterwork in its own right, with exposed beams, high-end custom woodwork, and windows throughout that fill every room with light. Every detail, from the stonework to the finest materials, reflects the artistry of master stonemasons and skilled craftsmen. The house is perched above the Jimmy Dean Brook and the Tweed River, where the sound of running water settles peacefully over the property. Enveloped by forest on all sides, the stone, concrete, and timber structure sits on its mountain top setting so naturally that it feels less built than grown from the land itself, as if it had always been there. Large windows, stone patios and a second-floor porch frame views down the valley to the northeast and out across the surrounding woodland. On mornings when fog fills the valley below, the houses, elevated location gives the sensation of floating above the world on a cloud, a true private retreat. The property spans 210 acres across two contiguous parcels, the majority of which is untouched private forest in Pittsfield, with development potential on the 89-acre Killington parcel. Combining privacy, character, and genuine architectural originality, the estate remains just minutes from an impressive range of amenities, ski resorts, shops, and dining, making this a rare chance to own a home and landscape unlike any other in Vermont.

4 Beds ⋅ 4 Baths ⋅ 5110057 MLS

Set within 210 acres of unspoiled forestland spanning Killington and Pittsfield, Vermont, The Tweed River Estate is a truly one-of-a-kind property, a private sanctuary where nature and craftsmanship meet. Designed by a renowned architect, the bespoke home is a masterwork in its own right, with exposed beams, high-end custom woodwork, and windows throughout that fill every room with light. Every detail, from the stonework to the finest materials, reflects the artistry of master stonemasons and skilled craftsmen. The house is perched above the Jimmy Dean Brook and the Tweed River, where the sound of running water settles peacefully over the property. Enveloped by forest on all sides, the stone, concrete, and timber structure sits on its mountain top setting so naturally that it feels less built than grown from the land itself, as if it had always been there. Large windows, stone patios and a second-floor porch frame views down the valley to the northeast and out across the surrounding woodland. On mornings when fog fills the valley below, the houses, elevated location gives the sensation of floating above the world on a cloud, a true private retreat. The property spans 210 acres across two contiguous parcels, the majority of which is untouched private forest in Pittsfield, with development potential on the 89-acre Killington parcel. Combining privacy, character, and genuine architectural originality, the estate remains just minutes from an impressive range of amenities, ski resorts, shops, and dining, making this a rare chance to own a home and landscape unlike any other in Vermont.

324 Fellows Rd, Pittsfield

253 Lookout Rd, Pittsfield

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.

3 Beds ⋅ 3 Baths ⋅ 5105259 MLS

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.

253 Lookout Rd, Pittsfield

89 Townsend Brook Rd, Pittsfield

Located in the heart of central Vermont, this fully furnished and equipped five-bedroom home provides convenient access to Killington Resort and nearby snowmobile trails, making it an ideal choice for skiers, mountain bikers, hikers, golfers, and outdoor enthusiasts alike. With an established rental history, it also presents an excellent opportunity as a vacation home with income potential. Inside, the home has a warm and welcoming atmosphere, with a cozy propane fireplace serving as the centerpiece for relaxing after a day outdoors. The comfortable kitchen and living area create an inviting space to gather with family and friends, while the five-bedroom layout offers plenty of room for guests, multiple families, or a dedicated home office. After a day on the slopes or the trails, unwind in the hot tub or head into the charming town of Woodstock to enjoy local restaurants, shopping, and classic Vermont character. Whether you're looking for outdoor adventure, a peaceful weekend getaway, or an investment property, this home provides easy access to many of the region's most popular attractions. With its flexible layout, proven rental appeal, and prime location in the Green Mountains, 89 Townsend Brook Road is ready for its next chapter. Call today for more details or to schedule a private showing.

5 Beds ⋅ 3 Baths ⋅ 5099518 MLS

Located in the heart of central Vermont, this fully furnished and equipped five-bedroom home provides convenient access to Killington Resort and nearby snowmobile trails, making it an ideal choice for skiers, mountain bikers, hikers, golfers, and outdoor enthusiasts alike. With an established rental history, it also presents an excellent opportunity as a vacation home with income potential. Inside, the home has a warm and welcoming atmosphere, with a cozy propane fireplace serving as the centerpiece for relaxing after a day outdoors. The comfortable kitchen and living area create an inviting space to gather with family and friends, while the five-bedroom layout offers plenty of room for guests, multiple families, or a dedicated home office. After a day on the slopes or the trails, unwind in the hot tub or head into the charming town of Woodstock to enjoy local restaurants, shopping, and classic Vermont character. Whether you're looking for outdoor adventure, a peaceful weekend getaway, or an investment property, this home provides easy access to many of the region's most popular attractions. With its flexible layout, proven rental appeal, and prime location in the Green Mountains, 89 Townsend Brook Road is ready for its next chapter. Call today for more details or to schedule a private showing.

89 Townsend Brook Rd, Pittsfield

91 Bombadil Path, Pittsfield

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.

3 Beds ⋅ 4 Baths ⋅ 5092220 MLS

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.

91 Bombadil Path, Pittsfield

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