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

Enjoy privacy and lovely views from this well executed contemporary home overlooking copious gardens and mature plantings to a spectacular pond with an arched footbridge (spotlights highlight the bridge after dark) to access your own little island. Beautiful updates throughout the home include new maintenance-free manufactured cedar-tone shingles on the entire house and workshop shed. The kitchen features custom oak cabinetry, granite counters and updated appliances. The living room has sweeping cathedral ceilings, hardwood walls, oversized windows, and a wood burning fireplace. There is a primary Bedroom ensuite, and a guest powder room off of the foyer mudroom complete with slate floors. Step out to a private iron balcony with Trex decking and spiral stairway accessing a stone terrace below complete with fire pit, water feature and screened gazebo. Upper level has a spacious loft area, and a second bedroom. The walk out lower level includes a third bedroom, studio/rec room (could accommodate overflow guests) and laundry, plus a wine or root cellar. Oversized two car garage with plenty of storage above. Located just minutes from I 91. Easy access to Upper Valley, DHMC, Woodstock, skiing and all recreation.

“The Hideaway House”. . . An Oasis of Tranquility. Nestled away in a bowl of woods & set back over 200 feet from the road, this 3-bedroom, 3-full-bath home with attached 2-car garage & extremely high-speed fiber optic Internet offers sanctuary-like privacy situated on 5.52 hillside acres in fashionable West Windsor, VT. This welcoming residence is secluded serenity at its best & is located in such an ultra-quiet setting that you’ll feel you’re living on your own private carriage road. Ceramic-tiled floor kitchen & adjoining dining area has a handsome raised-hearth fireplace that adds warmth & ambiance to your meals. The tasteful living room has an inviting fireplace & fir flooring. The 1st-floor primary bedroom can be used as a sunny den & has a French door to the back lawn. Upstairs is a large alternative primary bedroom with cathedral ceilings, a cozy fireplace, & oak flooring. The 3rd bedroom has a cathedral ceiling & 18' x 5' storage loft. Each of the 3 bedrooms has a full-sized en-suite bathroom & double closet. “The Hideaway House” is a serene wooded retreat that combines peaceful privacy with proximity to multiple conveniences. Located in a quintessential Vermont community, this property is just minutes from I-91, horse country, & Mt. Ascutney’s hiking, mountain biking, & skiing. Enjoy nearby Hanover, NH’s restaurants, shops, & Dartmouth College events; easy access to Dartmouth Medical Center; the charming village of Woodstock; & famed Killington & Okemo ski mountains.

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. This is what a true turnkey home looks like; new roof, windows, siding, decking, electrical, flooring, whole house generator, and beautiful new baths and kitchen complete with granite countertops. Boiler was replaced just before these owners purchased in 2016. Even the basement has potential to be fully finished if you need more living space or to have a workshop or home studio. 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.

Escape to the charm of Brownsville, Vermont, where this 2-bedroom, 1.5-bath home sits at the base of majestic Ascutney Mountain. A welcoming living room highlights floor-to-ceiling windows that frame sweeping mountain views, creating a serene backdrop year-round. The updated kitchen features stainless steel appliances, a tile backsplash, ample counter space, and a convenient pantry, while the adjoining dining area offers continued vistas and access to a spacious rear deck, perfect for outdoor dining and entertaining. Upstairs you’ll find two tranquil bedrooms and a full bath. The attic adds a flexible bonus space, ideal for a reading nook, office, or playroom. A partially finished basement expands the living options with a half bath, laundry, and versatile family room, guest, or recreation area. From here, enjoy direct access to the attached two-car garage, providing easy winter parking and plenty of storage for outdoor gear. Set in a desirable location, this property offers the perfect blend of comfort, convenience, and natural beauty, an ideal retreat in the heart of Vermont.

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