Properties Near 58 Morningside Drive Windsor, VT

Welcome to this 3-bedroom, 1-bath farmhouse in the heart of West Windsor, VT! Inside, you’ll find a warm and inviting open-concept layout featuring a main floor bedroom, and mudroom. Perfect for gatherings or quiet evenings. Beyond the farmhouse, the property includes a wonderful collection of outbuildings—a classic barn, a 2-car garage, a workshop with a woodstove, and even a sugarhouse—making it ideal for hobbies, homesteading, or simply enjoying the Vermont lifestyle. There is over 18 acres of wide open field, ready for your animals, and you can even have ample hay for feed. With plenty of space indoors and out, this property offers both charm and practicality in a beautiful rural setting. Open House Saturday August 23rd 10-12noon

Adorable & Turn-key 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. Be part of the action at Ascutney Outdoors; walk to hiking & mountain biking, skiing & tubing just outside your door! All appliances except portable a/c units & 2 freezers, will convey with sale.

OWNERS SAY SELL before Winter. Check out the new PRICE! Nestled on 1.34 picturesque acres in historic Windsor, this classic 4-bedroom Colonial blends timeless charm with comfortable living. Set back from the road, the home offers privacy and space to enjoy Vermont’s natural beauty while being just minutes from town amenities, schools, and I-91. Inside, you'll find a traditional floor plan with spacious living and dining areas, a well-appointed kitchen, and plenty of natural light throughout. With this flexible layout, you can configure bedrooms on 1 or both levels. The basement is dry, and has ample finished space for an extra playroom or family room, including 1/2 bathroom. The expansive yard is ideal for gardening, play, or simply taking in the peaceful surroundings. With room to grow, work from home, or create the lifestyle you've been dreaming of, this Windsor gem is ready to welcome its next chapter.

Welcome to this well-kept ranch home in the heart of Windsor, VT. Offering 3 bedrooms and 1.5 baths, this home provides a comfortable layout, perfect for everyday living. The spacious living room is bright and inviting, opening easily into the eat-in kitchen where there’s plenty of room for family and friends to gather. Enjoy the convenience of a 2-car garage and a level lot that’s ideal for gardening, pets, or outdoor entertaining. Single-level living makes this property easy to maintain, while the location offers quick access to Windsor’s shops, restaurants, and local amenities. Whether you’re looking for your first home, a place to downsize, or a Vermont getaway, this ranch is full of potential and ready for its next chapter.

Open House 10/4/1025 11Am-1Pm. This lovingly maintained Cape-style home, perfectly set on a 0.18-acre corner lot. With 2 bedrooms, 1.5 bathrooms, a welcoming covered porch, and spacious basement, this home blends classic Vermont character with everyday comfort. The home has a standing seam roof and a brand new boiler, with timeless features such as built-in cabinetry, hardwood floors, and ample closet space. Bonus rooms on each floor add to its charm and flexibility. The two-car garage with attic storage offers plenty of room for vehicles, tools, and more. Inside, the traditional layout provides a functional, warm, and inviting flow but leaves room for adding your own personal touches. Enjoy the convenience of being within walking distance to local amenities like Kennedy’s Pond and the Windsor Fairgrounds all while savoring the peace and space of your corner lot, ideal for gardening, play, or quiet relaxation.

Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash flow. Each unit features 2 spacious bedrooms, 1 full bathroom, a bright living area, and a spacious kitchen, making it ideal for tenants or personal use. Separate utilities ensure ease of management and straightforward billing, while continued thoughtful maintenance enhances long-term value and efficiency. Just minutes from local shops, dining, and schools, this property offers small-town charm with big investment potential. Enjoy easy access to I-91 and nearby recreational opportunities including hiking, skiing, and kayaking/fishing. Whether you choose to live in one unit and let the other help pay your mortgage, or fully rent both for reliable income, this duplex is a rare find in a desirable location. Don’t miss your chance to own this flexible and financially smart property in one of Vermont’s most charming towns. Schedule your showing today!

Welcome to this well-maintained 3-bedroom, 3-bathroom condo at Ascutney Mountain Resort, offering year-round enjoyment in a beautiful mountain setting. The inviting living room features a cozy fireplace and access to a deck, perfect for relaxing or entertaining. The main level has a primary suite with access to the trails out your back door, and also 1/2 bath complete with laundry area. The lower level has 2 more bedrooms, 3/4 bath, and family room. Recent updates include new flooring, new hot water boiler system, and new full size washer and dryer. The unit will also be furnished with the exception of a few items, making this truly move in ready! The resort offers something for every season: skiing with a T-bar and rope tow, tubing, and endless mountain biking and hiking trails. For dining, The Maple Kitchen restaurant is conveniently located on the resort grounds, while the Brownsville Butcher & Pantry is just a short drive away, offering a butcher shop, wine selection, groceries, and a cozy café. This condo has been enjoyed in all seasons and is ready for you to create your own memories. Come see why Ascutney Mountain Resort living is so special! Open House Sunday, September 28, 2025 9-11am