Properties Near 2 Pine Street Windsor, VT

This is one of those homes you simply have to experience in person. The views alone are worth the visit. Perched above the valley with commanding, panoramic views of Mount Ascutney, this exceptional custom-built home offers a front-row seat to some of Vermont's most breathtaking scenery. From sunrise over the mountains to spectacular evening sunsets, every window showcases a landscape that changes beautifully with the seasons. Designed for comfortable everyday living and effortless entertaining, this thoughtfully crafted four-bedroom, three-bath home features the convenience of a first-floor primary suite, while three spacious upstairs bedrooms provide room for family, guests, or dedicated home office space. The finished walkout lower level adds even more flexibility with a bonus bedroom, expansive recreation room, and the potential for an in-law suite, guest quarters, or private workspace with its own entrance. Step outside onto the impressive 900-square-foot deck, where you'll enjoy outdoor dining, morning coffee, and unforgettable gatherings overlooking the mountains and valley below. The spacious yard offers plenty of room for gardening, recreation, or simply enjoying Vermont's abundant wildlife. A charming, well-built chicken coop adds a touch of country living and farmhouse appeal. Built with efficiency in mind, the home's passive solar greenhouse roof system captures and stores natural heat, helping reduce energy costs while embracing sustainable Vermont living. Located in the highly desirable West Windsor community, you'll enjoy easy access to Mount Ascutney, Ascutney Outdoors, miles of hiking and biking trails, the renowned VAST snowmobile trail system, and world-class skiing at Okemo and Killington. The villages of Woodstock, Brownsville, and the Upper Valley are all within easy reach, making this an ideal year-round residence or Vermont getaway. Custom homes with this level of craftsmanship, flexible living space, and truly unforgettable views are rare.

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 living room that overlook the nearby pond providing a peaceful retreat at the end of a long day!

Adorable partially furnished 3 bedroom, 2 bath home on landscaped 1.53 acres corner lot in the heart of Ascutney Mt Resort! Many upgrades including Bosch High Efficiency Propane Boiler, Mitsubishi heat pump/AC, Rinnai on demand hot water heater, new well tank & centrifuge filtration system, new fireplace & chimney with Woodstock soapstone woodstove flanked by custom cabinets on each side. Decks, extensive perennial gardens, pond, vegetable garden area & fruit trees. Outbuildings for various storage needs. Automatic/timed lighting on granite posts line the driveway. At Ascutney Outdoors; walk to hiking & mountain biking, skiing & tubing just outside your door! Selling due to job situation. Ascutney Mountain has protective covenants including rights of 1st refusal.

Open House Sunday July 26th 10a.m. - 12 p.m.! Single Family or Duplex! Live in it as a spacious 3 bedroom, 2 bath single family home, or take advantage of the current setup as two separate 1 bedroom units, each with its own utilities. That kind of flexibility is hard to find, whether you're thinking multigenerational living, rental income, or just extra breathing room. And then there's the view. Gorgeous lake views greet you from inside this home, the kind that make you stop and appreciate where you live every single day. This is a true Victorian, full of the character and detail that newer homes just can't replicate. The full basement includes a bonus room, perfect for a home office, workshop, or extra storage. A detached garage adds even more convenience for parking and yard equipment. Tucked into charming Windsor, you're close to 91 and just minutes from local shops and restaurants downtown. Homes with this much versatility and this kind of view don't come along often.

Motivated Seller - Price Improved! Own a remarkable piece of Vermont history in the heart of Windsor. Built circa 1790, this beautifully preserved brick-and-frame Colonial blends timeless New England character with the modern updates today's buyers appreciate. Rich in craftsmanship and architectural detail, this one-of-a-kind home offers the perfect balance of historic charm, everyday comfort, and exciting future potential. Inside, you'll find wide-plank hardwood and softwood floors, abundant natural light from updated windows, fresh interior paint, and thoughtfully updated electrical and heating systems. A classic standing seam roof enhances both the home's historic appeal and long-term durability. At the heart of the home is a truly unforgettable kitchen, where carefully repurposed materials create a warm, inviting space full of personality and Vermont character. The attached one-car garage features a dedicated workshop and storage area, while the expansive attic—accessible from both levels—offers incredible flexibility for a studio, workshop, additional storage, or future finished living space. Located just moments from Artisans Park, downtown Windsor, and Interstate 91 (Exit 9), this property provides convenient access to the Upper Valley, DHMC, Dartmouth College, and nearby NH communities. Whether you're commuting, working remotely, or looking for a centrally located Vermont home, you'll appreciate the convenience without sacrificing small-town charm. With commercial zoning potential, this property presents a rare opportunity for entrepreneurs, professionals, investors, or anyone seeking a live-work lifestyle. Imagine a boutique office, gallery, creative studio, or small business operating from one of Windsor's historic homes while enjoying all the comforts of a private residence. Whether you're searching for a historic Vermont home, a unique investment property, or a place where your home and business can thrive, stop scrolling and come see.