Properties Near 3 Cherry Street Windsor, VT

Classic Vermont character meets everyday convenience in this sweet in-town New Englander. Set in the heart of Windsor, this three-bedroom, one-bath home puts you steps from local shops, dining, and all the charm of one of Vermont's most historic villages. Inside, a fireplace anchors the living space, offering the kind of warmth that makes a New England winter something to look forward to. The thoughtful layout makes the most of every square foot, with comfortable bedrooms and a functional flow throughout. Outside, a detached garage provides coveted covered parking and additional storage — a true Vermont essential. The in-town location means walkability without sacrificing the quiet, neighborly feel that defines life in the Upper Valley. Whether you're a first-time buyer, looking to downsize, or searching for a Vermont retreat, this is a home that delivers on all the right things: location, character, and comfort.

Welcome to this nicely maintained 2-bedroom + loft condo offering direct access to the renowned Ascutney Trails—perfect for mountain biking, skiing, hiking, and trail running. Enjoy stunning mountain views from the spacious living room, which features two large sliding glass doors that flood the space with natural light. The open loft above the living area offers even more scenic vistas and flexible living space. Both bedrooms feature charming exposed beams, adding warmth and character. Peaceful and private, yet just a short walk to village amenities and minutes from I-91, this home combines tranquility with convenience. With in-unit laundry and strong rental potential, this is an ideal primary home, weekend getaway, or investment opportunity!

This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the property. This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including mountain biking, hiking, cross-country skiing, snowshoeing, and affordable alpine skiing on natural snow. *Fees include utilities!! 1726.00 quarterly for association fee and a variable 1163.00 quarterly fee for electric, heat, sewer, trash, water Perfectly situated, you're about 30 minutes from Woodstock, Ludlow, and Okemo, with Killington, Bromley, and Magic Mountain just a bit farther. The Green Mountain Horse Association is only 20 minutes away, and both Boston and Hartford are reachable in about 2.5 hours. Enjoy delicious dining just a short stroll away at the Hotel’s restaurant or the beloved Brownsville Butcher & Pantry. Subject to Covenants and Right of First Refusal. Experience mountain living with a thriving volunteer-driven community at Ascutney Outdoors and a hub for year-round adventure!