Properties Near 358 US Route 5 Windsor, VT

Welcome to this inviting 2-bedroom, 1.5-bath ranch-style home located just a short distance from Main Street in Windsor, VT. Set on a manageable and sunny .29-acre lot, this home offers convenient single-level living with a bright, open-concept kitchen and living area—perfect for relaxing or entertaining. A spacious back enclosed porch extends your living space, ideal for enjoying Vermont’s changing seasons. The kitchen has been updated, the floors meticulously maintained, and the bedrooms are ample sized, with the ability to function as a 3 bedroom home. The basement is also partially finished and could add that bonus space you seek.The one-car attached garage adds extra ease for daily living. Enjoy the benefits of being close to town amenities, schools, and recreation while still having your own private yard.

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!

Beautiful Fully Furnished Home with a Solid Airbnb Rental History. This charming VT townhouse features 3 bedrooms, 2.5 baths and has a wonderful flow for gathering. Bright and cheerfully decorated, it is currently designed to sleep eight. The mudroom entryway has natural light and a coat closet and upon entering you will be greeted by a well-appointed living space with every familiar comfort. The living room offers a warm place for gathering and includes both a wood burning fireplace as well as a balcony covered-porch that opens out to fresh air. The kitchen has a drop-in double sink and Corian countertops, and the 1/2 bath on the main level opens into a utility room with stackable washer & dryer. The master suite includes a walkout covered patio with a grill, and an en-suite full bathroom. Moving downstairs there is a cozy family room, 3/4 bath, and two additional bedrooms, both with natural light. Ample closet space (with private owners closet) and warm carpeting throughout. Excellent location at the foot of Ascutney Outdoors Center (hiking and biking) and Mnt. Ascutney is a decades-old Ski mountain resort. Just a mile away you will find the Brownsville Butcher & Pantry and the Windsor or Brownsville Trail can take you to breathtaking summit views at the top of Mt. Ascutney. You'll be within 30 miles of DHMC, West Lebanon shopping, Okemo Mountain Resort, and close to Woodstock and Hanover NH. Water bill of $480/yr. The Special Assessment of $528/qtr expires at end of 2025.

Beautiful Fully Furnished Home with a Solid Airbnb Rental History. This charming VT townhouse features 3 bedrooms, 2.5 baths and has a wonderful flow for gathering. Bright and cheerfully decorated, it is currently designed to sleep eight. The mudroom entryway has natural light and a coat closet and upon entering you will be greeted by a well-appointed living space with every familiar comfort. The living room offers a warm place for gathering and includes both a wood burning fireplace as well as a balcony covered-porch that opens out to fresh air. The kitchen has a drop-in double sink and Corian countertops, and the 1/2 bath on the main level opens into a utility room with stackable washer & dryer. The master suite includes a walkout covered patio with a grill, and an en-suite full bathroom. Moving downstairs there is a cozy family room, 3/4 bath, and two additional bedrooms, both with natural light. Ample closet space (with private owners closet) and warm carpeting throughout. Excellent location at the foot of Ascutney Outdoors Center (hiking and biking) and Mnt. Ascutney is a decades-old Ski mountain resort. Just a mile away you will find the Brownsville Butcher & Pantry and the Windsor or Brownsville Trail can take you to breathtaking summit views at the top of Mt. Ascutney. You'll be within 30 miles of DHMC, West Lebanon shopping, Okemo Mountain Resort, and close to Woodstock and Hanover NH. Water bill of $480/yr. The Special Assessment of $528/qtr expires at end of 2025.

Nestled in a peaceful rural setting, this roomy 4-bedroom, 3-bathroom home offers incredible potential for those looking to create their dream country home. While the property is in need of some work, it features a generous layout and sits on a little over an acre, which allows for plenty of space to enjoy the beautiful setting. The home features hardwood floors, vinyl windows, a pellet stove, as well as nicely appointed kitchen and granite countertops. Whether you're an investor or a homeowner with a vision, this fixer upper is a rare opportunity to craft a customized living space in a serene countryside location. Showing requires 24-hour notice due to tenants, property is being sold "as is".

Attractive two bedroom, 1 bath ranch style home on a serene 1.08-acre parcel nestled along scenic Rush Meadow Road in West Windsor. Right in the heart of Horse Country! The kitchen has upgraded cabinetry and there is overflow third bedroom space in the lower level that can be turned into home office or den usage. This gently sloping lot offers a harmonious blend of open lawn and pleasant woodland, providing both privacy and picturesque views. Attractive hardwood floors grace the Living Room and the exterior deck will give good western sunsets. The lower level walkout could be heated with wood if you want to provide a woodstove. Home comes with some practical equipment if desired - newer lawn tractor, push mower, snow blower, etc. Situated just minutes from the charming village of Brownsville, the property enjoys a tranquil setting with convenient access to local amenities. Outdoor enthusiasts will appreciate the proximity to Mount Ascutney, a prominent peak rising to 3,144 feet, offering a variety of recreational activities including hiking, mountain biking, and backcountry skiing. The nearby Ascutney Trails network provides extensive routes for all skill levels, while the adjacent Ascutney State Park offers additional hiking and camping opportunities. Whether you’re envisioning a private retreat or a year-round residence, 1084 Rush Meadow Road offers the perfect opportunity to own a slice of Vermont paradise.

Great Location! Well-Maintained! 4BR's Cape Full Basement with work bench, Many recent updates in the last three years, Rear deck, Garden area and Private backyard.

Welcome to this beautifully maintained New Englander nestled in the historic town of Windsor — Vermont's first capital and a gem of the Upper Valley. This classic 3-bedroom, 2-bath home blends timeless charm with thoughtful updates, offering a perfect retreat in a vibrant, small-town setting. Located within walking distance to Windsor’s shops, restaurants, schools, and the picturesque Connecticut River — and just minutes from I-91 — this home combines small-town charm with accessibility.