Properties Near 74 Union Street Windsor, VT

A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of mind of updated electrical and heating systems, and the curb appeal of a classic standing seam roof and fresh paint throughout. Recent windows flood the interior with natural light while preserving the home's timeless character. Whether you're drawn by the historic details or the practical updates, this property is move-in ready from day one. The kitchen is showstopping with a seamless blend repurposed materials. It exudes character and charm. The attached 1 car garage — complete with a dedicated storage room/workshop area and a massive open attic accessible from both levels — offers flexible space for a workshop, studio, or expansion. A property of this age rarely offers this much functional square footage. Positioned conveniently off Exit 9, commuting to the Upper Valley and beyond is effortless. The commercial zoning potential makes this an exceptional opportunity for buyers seeking a live-work arrangement, professional office space, or a savvy investment in one of Vermont's most storied small towns. Historic character. Modern comfort. Extraordinary potential.

Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living and entertaining. A main-level bedroom and full bath, along with convenient first-floor laundry, offer ideal single-level living options or guest accommodations. Upstairs, you’ll find three generously sized bedrooms, providing plenty of space for family, guests, or a home office setup. Set on a quarter-acre lot, the property offers ample parking and a detached one-car garage, perfect for storage, hobbies, or a workshop. Centrally located and easy access to town, grab your morning coffee just a short walk away or head to the nearby pond for a relaxing swim. A wonderful opportunity to own a well-located home with space, charm, and versatility in Windsor!

Privately sited at the end of a quiet dead end road on beautiful Mt. Ascutney, this cozy 2 BR, 2 BA Chalet style home is an ideal-low maintenance vacation home, or an efficient starter. LR/DR with cathedral ceiling anchored by a sweeping fieldstone fireplace, with woodstove insert; and a spiral staircase leading to a loft-perfect for your home office. Kitchen with built ins, and updated appliances. A 3/4 BA further completes the main level. Two bedrooms, full bath and laundry on walk out lower level. Miles of trails for hiking and biking just outside your door, and a short stroll to the year round recreation and festivities at Ascutney Outdoors. This sweet Chalet is a great opportunity! Most furnishings available, with a few exceptions. Off peak electric radiators provide heat. Subject to standard ROFR.

This inviting condo offers the perfect blend of comfort, convenience, and year-round outdoor access. Step right outside your back door to enjoy scenic hiking and biking trails, while world-class skiing and snowboarding are just moments away. This unique home features two separate floors, ideal for flexible living. The first floor offers its own private entrance, along with dedicated bedrooms and a full bathroom—perfect for guests, extended family, or potential rental opportunities. Upstairs, the main living space is designed for easy living, with a functional layout that makes relaxing after a day on the slopes effortless. Enjoy a low-maintenance lifestyle with minimal upkeep required, making this property ideal as a primary residence, vacation getaway, or investment property.

Tucked away from the other buildings, this unique three-bedroom, three-bath condominium offers a peaceful setting with wooded views from all three private balconies. Thoughtfully remodeled, the home features newer hardwood flooring, updated carpeting, and tastefully renovated bathrooms. The open-concept main level includes a comfortable kitchen with a breakfast bar, a dedicated dining area, and an inviting living room with a wood-burning fireplace and access to a balcony, perfect for relaxing or entertaining. This level also offers a full bath, in-unit laundry, and a bright, airy bedroom with its own private balcony. Upstairs, you’ll find two spacious bedrooms, each with en-suite baths, along with an additional balcony that enhances the home’s connection to its natural surroundings. Whether you’re looking for a year-round residence or a weekend retreat, this property offers the perfect opportunity to enjoy nearby amenities in every season.

Immaculate end-unit condominium offering the ease of single-floor living at its finest. Thoughtfully maintained and move-in ready, this home impresses from the moment you walk in- tasteful finishes throughout create a polished, welcoming atmosphere. Newer windows flood the space with natural light, and a new heating system ensures year-round comfort. The primary suite features a beautifully updated walk-in tiled shower. The walkout lower level hosts two additional bedrooms, is exceptionally bright, and offers a family room for all to enjoy. Positioned in the most desirable spot in the complex — the closest unit to the brand-new rope tow — this is a skier's dream. Incredible recreational trails and exciting new developments continue to elevate Ascutney. The seller has cherished this location and speaks highly of both the management company and board of directors- a well-run association that shows in every detail of this community. Priced to reflect its superior condition and unbeatable location, one visit will make it clear, this one is worth every penny.