Properties Near 66 Union Street Windsor, VT

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!

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.

PRICE JUST IMPROVED! 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.

OWN FOR LESS THAN YOU CAN RENT!! Spacious and bright end unit condo on Ascutney Mountain. Fireplaced living room, dining area with balcony, kitchen and even an entry enclave. 3 bedrooms with 3 full baths. 1 bed/bath on 1st floor. 2 bedrooms, 2 baths, multiple closets and a sitting area on the upper level. The advantage of the 3rd floor is that you get the loft area, cathedral ceilings and some much light! Outside abounds with nature with walking trails, biking, rafting, kayaking,winter tubing and skiing within sight. Ascutney State Park is within a stones throw, yet main roads and easy access to the Upper Valley! Available for immediate occupancy.

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 tubing hill and take in all the action just outside your door! 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. 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!

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the years, the house was purchased by Historic Windsor, Inc. in 2008. Recognizing its historic significance along with much original fabric intact, Historic Windsor, Inc. engaged in a massive cleanup, extensive documentation and a complete paint job with some sections reroofed with standing seam. The residence is now ready for the next phase of its life as a single family residence, up to 4 residential apartments, owner occupied business or a cultural center. All of the necessary as built architectural plans, documentation of existing materials and fabric and proposed Feasibility Plans are available. The project will require all new systems and rehab working with the extensive original fabric including interior shutters, period flooring and window and door detailing. Many original doors. The residences rich history with Stephen Jacob and its architectural significance will regain its prominence in Historic Windsor upon completion.

Discover this pleasant multi-level condominium offering a comfortable and versatile layout in a desirable Mt. Ascutney location. The home features a spacious open-concept living and dining area with soaring cathedral ceilings, and access to a covered porch—perfect for relaxing and taking in the surroundings. With 2 bedrooms, 2 full baths, and a versatile loft (not approved for sleeping per Fire Marshal), there's room for work, hobbies, or guests. Additional highlights include a ground-level mudroom and a convenient first-floor laundry area, and did we mention that it's being offered furnished. Enjoy access to Ascutney's outdoor lifestyle—hiking and mountain biking trails right out your door. Plus, community-run T-bar and tubing area, as well as ample backcountry skiing terrain, adds a unique winter recreational touch. With easy access to the Upper Valley, this well-maintained condo is a must-see! **Right of first refusal applies.

Single-Level Home in the Heart of Windsor! Welcome to this inviting 3-bedroom, 2-bath home nestled on a quiet street in historic Windsor, Vermont. This well-maintained, single-level property offers the perfect blend of comfort, convenience, and New England charm. Step inside to discover a bright and open living space with warm hardwood floors, plenty of natural light, and a cozy atmosphere that makes you feel right at home. The kitchen features ample cabinet space and a functional layout, ideal for everyday living or entertaining. Each of the three bedrooms is generously sized with closet space and pleasant views of the surrounding neighborhood. A full basement offers extra storage or the potential for a workshop or hobby area. The Fairgrounds is right across the street, complete with dog park, skate park, basketball courts, tennis courts, ball fields, and a playground, and let's not forget the trail system. Located just minutes from local shops, schools, parks, and the picturesque Connecticut River, this home offers small-town charm with easy access to I-91 for commuting. Whether you're a first-time buyer, looking to downsize, or searching for a peaceful retreat, this property is a must-see.