You are viewing Windsor Area VT Homes between $0 and $30000000 dollars.
New Listing!
$1,345,000 $233 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
7 Beds | 6 Baths | Total Sq. Ft. 5774 | Acres: 5.51Listed on Wednesday Jun 3, 2026
Description: Set against sweeping views of Mount Ascutney, this distinctive property offers the kind of Vermont escape buyers rarely find--private, spacious, and designed for gathering. Thoughtfully expanded over time, the home seamlessly blends two living spaces, creating an ideal setting for hosting extended family and friends while still offering comfort and privacy for all. The newer portion of the home is centered around light and connection, with an open-concept living, dining, and kitchen area anchored by a custom stone fireplace and framed by floor-to-ceiling windows that capture the mountain views. Step out onto the sun-drenched deck--perfect for morning coffee, après-ski evenings, or summer entertaining. The primary suite offers a peaceful retreat with its own private deck, ensuite bath, walk-in closet, and dedicated office space. The original wing of the home provides additional room for guests, featuring four bedrooms, kitchen and its own living area, as well as direct access to a second deck overlooking the surrounding landscape--creating a natural separation that makes hosting effortless. Whether used as a single expansive home or configured to offer private guest accommodations, the layout supports a range of lifestyles--from weekend retreats to extended stays. Located in the heart of Brownsville, just moments from the trails and outdoor recreation of Mount Ascutney, this property offers four-season appeal. Enjoy easy access to the charm of nearby Woodstock, as well as skiing at Okemo and Killington, and the cultural and dining destinations of the Upper Valley. A rare opportunity to create a true Vermont getaway--designed for connection, relaxation, and year-round enjoyment. See Listing Details & 32 images. Includes a Virtual Tour
Under Contract
$930,000 $395 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
Waterfront on Pond _Unnamed4 Beds | 3 Baths | Total Sq. Ft. 2352 | Acres: 80
Listed on Wednesday Apr 15, 2026
Description: Discover a truly rare opportunity to own an extraordinary piece of Vermont countryside. This 4-bedroom, 3-bath home is set on 80 acres of pristine woodland with nearly a full mile of road frontage for exceptional accessibility and future potential. Lovingly held by the same family for over 60 years, the property is rich in history, with classic stone wall boundary lines that echo its past. This charming raised ranch blends comfort and space, perfectly positioned to take in breathtaking views of Mount Ascutney. Surrounded by natural beauty and abundant wildlife, outdoor enthusiasts will appreciate the close proximity to the VAST Trail System and Mount Ascutney Ski Area, offering year-round recreation right at your doorstep. Ideally situated less than 15 minutes from the Green Mountain Horse Association, under 2 hours from Manchester-Boston Regional Airport, and just under 2.5 hours from Boston, Massachusetts. Whether envisioned as a private retreat, a legacy estate, or an investment with room to grow, this remarkable property seamlessly blends heritage, scenery, and endless possibility. See Listing Details & 59 images. Includes a Virtual Tour
Under Contract
$548,000 $229 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
3 Beds | 4 Baths | Total Sq. Ft. 2391 | Acres: 1.49Listed on Friday May 15, 2026
Description: Views of Mt. Ascutney from this well cared for contemporary home that has only been used as a second home for the original owners. The house takes advantage of the southwest exposure to be able to bring the outside in with the use of large palladium windows and multiple French doors. Some of the interior features include 3 woodburning fireplaces ,wide pine floors ,vaulted ceilings ,and skylights. The floor plan has an easy flow. The charming kitchen leads into a spacious dining room with fireplace. The living room with stunning fireplace leads out to a large deck for outdoor dining. Off of the living room the cozy family room features a wall of built-in bookcases. The downstairs bedroom complete with private bath opens onto the spacious screened in porch. The primary bedroom is upstairs. It features a built in king sized bed with drawers for extra storage, walk in closets ,and full bath. also on the second floor is another bedroom and bath with walk in shower. The grounds of mature gardens, antique apple trees , blueberry, raspberry bushes ,and original stone walls that border the north and east boundaries create a magical setting. There is ample land to add a garage. Easy access to the Upper Valley with all of the amenities including shopping , Dartmouth College , and world class Dartmouth Medical Center. Woodstock, named by many magazines one of the prettiest small towns in America is less than 25 minutes away.5 hrs to NYC 2 hrs to Boston. See Listing Details & 55 images.
$474,800 $321 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1480 | Acres: 1.53Listed on Thursday Apr 16, 2026
Description: Adorable partially furnished 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. At Ascutney Outdoors; walk to hiking & mountain biking, skiing & tubing just outside your door! Selling due to job situation. Ascutney Mountain has protective covenants including rights of 1st refusal. See Listing Details & 24 images.
$535,000 $108 per sq.ft. Windsor VT Home »
6 Beds | 4 Baths | Total Sq. Ft. 4933 | Acres: 0.48Listed on Wednesday May 13, 2026
Description: Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch or enjoy the private yard and great family room that overlook the nearby pond providing a peaceful retreat at the end of a long day! See Listing Details & 36 images.
$413,900 $143 per sq.ft. Windsor VT Home »
Price Change! Reduced by $10,100 down 2% on April 28th 2026
4 Beds | 3 Baths | Total Sq. Ft. 2888 | Acres: 1.22
Listed on Tuesday Mar 24, 2026
Description: Motivated seller! Price drop! 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. See Listing Details & 38 images.
Under Contract
$329,000 $154 per sq.ft. Windsor VT Home »
Price Change! Reduced by $10,000 down 3% on April 29th 2026
4 Beds | 2 Baths | Total Sq. Ft. 2142 | Acres: 0.25
Listed on Friday Apr 3, 2026
Description: 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! See Listing Details & 25 images.
$229,000 $227 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1008 | Acres: 0.05Listed on Thursday Apr 23, 2026
Description: Experience the rare opportunity to own a BRAND NEW home, located in the heart of Windsor. This home seamlessly blends efficiency with style, featuring a thoughtfully elevated foundation designed to sit securely out of the flood zone for total peace of mind. The interior offers open living on the first level, and generous sized bedrooms upstairs, maximizing all the available space. The exterior offers a charming covered porch perfect for relaxing. Enjoy the convenience of being just steps away from the Amtrak station, short drive to the local hospital, access to public transportation, and sidewalks that lead you right up into town. Whether you are looking for a low-maintenance primary residence or a high-demand rental asset, this property's brand-new construction and proximity to major employers is a win-win. See Listing Details & 13 images.
$229,000 $227 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1008 | Acres: 0.08Listed on Thursday Apr 23, 2026
Description: Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs. You are within walking distance to the Amtrak station and downtown, and our local Moover public transit service is ready to help. The community hospital is just a shore drive as well. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this new construction is a great choice. See Listing Details & 10 images.
Under Contract
$139,000 $181 per sq.ft. Windsor VT Home »
1 Beds | 1 Baths | Total Sq. Ft. 768 | Acres: 0.1Listed on Thursday Apr 23, 2026
Description: In the heart of Windsor, this charming opportunity was fully rebuilt in 2018. During the renovation, the foundation was raised to sit securely out of the flood zone, giving you peace of mind. Inside, the home features a large, over-sized entryway that leads into a comfortable open living space. The open loft adds a lot of character and extra charm to the layout. Enjoy the covered porch and the strip of opportunity to tend to some raised garden beds or entertain company. Within walking distance to the Amtrak station and downtown, and just a short drive to the hospital. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this updated home is a great choice. See Listing Details & 18 images.
$115,000 $479 per sq.ft. Windsor VT Home »
Price Change! Reduced by $4,000 down 3% on May 12th 2026
1 Beds | 1 Baths | Total Sq. Ft. 240 | Acres:
Listed on Monday Mar 16, 2026
Description: This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built deck--perfect for converting in to a sunroom--as well as a screened gazebo and a storage shed included in the sale. Located in a small, quiet park just 4 miles from I-19, this property offers both charm and convenience. If you've ever dreamed of owning a Tiny Home, this is your opportunity! See Listing Details & 26 images.
