You are viewing Windsor Area VT Homes between $0 and $30000000 dollars.
$275,000 $122 per sq.ft. Village of Ascutney in Town of Weathersfield VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 2250 | Acres: 0.6Listed on Thursday May 1, 2025
Description: Open floor plan with soaring ceilings and wood flooring throughout. The structure includes a full bathroom, a partial kitchen, and the framework for two bedrooms--ideal for conversion into a spacious single-family home or potentially a duplex. New hot air heating oil system install fall 2024 The building was officially approved for residential use in 2023. Recent upgrades enhance the property's appeal, including a new hot-air oil furnace, full foam insulation, new windows and doors (2018), anew electrical system (2018), and a handicap-accessible ramp to the front entrance. The full, walk-out concrete basement features high ceilings, multiple entry points(including a secondary "dog house" access), and offers excellent additional space for storage or further development. Septic system includes a 1,500-gallon tank and a pump chamber (installed in 2018), connected to a shared septic field rated for 700 gallons/day. The property provides ample parking for at least four vehicles. With flexible zoning, ample space, and key infrastructure already in place, this unique building presents a rare opportunity for creative redevelopment. Conversion to a duplex may be possible with appropriate permitting. Subject to right of first refusal by abutter. Agent has ownership interest. See Listing Details & 19 images.
$1,665,000 $288 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
Price Change! Reduced by $60,000 down 4% on April 22nd 2025
7 Beds | 6 Baths | Total Sq. Ft. 5774 | Acres: 5.51
Listed on Wednesday Oct 16, 2024
Description: Unique Two-Home Property with Stunning Mountain Views. Discover this exceptional property featuring two connected homes, seamlessly blending contemporary design with functionality. Originally built in 1975 and expanded in 2000, this unique residence offers a total of 7 bedrooms, perfect for multi-generational living or as a rental opportunity. The newer side of the home showcases beautiful hardwood floors, an expansive open floor plan, and a large primary suite complete with an ensuite bath, walk-in closet, office and a private deck. The spacious kitchen, dining, and living area boasts a custom stone fireplace, floor-to-ceiling windows, and sliders that lead to a renovated deck with breathtaking views of Ascutney Mountain. The original section of the home includes 4 bedrooms, another open living space, and access to an additional deck with serene views. Both sections can function independently, offering the flexibility of a secondary guest house, in-law living or rental possibilities. Located in the heart of Brownsville, this home is just a short distance from Ascutney Mountain and a short drive from I-91 and the Upper Valley, with convenient access to top Vermont attractions, including the historic and charming town of Woodstock only 30 minutes away, Okemo Mountain (30 minutes) and Killington Resort (45 minutes). Hanover and Lebanon, NH less than 30 minutes away, Mount and Lake Sunapee NH (45 minutes) making this property a perfect retreat. See Listing Details & 46 images. Includes a Virtual Tour
New Listing!
$669,000 $280 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 Wednesday Jun 18, 2025
Description: This well cared for contemporary home 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. Ascutney Mt. is near by with many year round sporting activities. 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.
New Listing!
$549,000 $371 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 Tuesday Jun 10, 2025
Description: Adorable & Turn-key 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. Be part of the action at Ascutney Outdoors; walk to hiking & mountain biking, skiing & tubing just outside your door! All appliances except portable a/c units will convey with sale. See Listing Details & 30 images.
New Listing!
$635,000 $437 per sq.ft. Windsor VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 1452 | Acres: 10.18Listed on Monday Jun 16, 2025
Description: 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 cedar shingles on the entire house, garage 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. See Listing Details & 39 images.
$350,000 $252 per sq.ft. Windsor VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 1391 | Acres: 0.29Listed on Sunday Jun 8, 2025
Description: 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. See Listing Details & 21 images.
$325,000 $133 per sq.ft. Windsor VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2452 | Acres: 0.75Listed on Thursday Jun 5, 2025
Description: 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! See Listing Details & 36 images.
New Listing!
$299,000 $224 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1332 | Acres: 22Listed on Wednesday Jun 18, 2025
Description: Here's a hidden gem for you in the heart of Vermont's magical, tranquil and picturesque countryside. Situated on 22 acres of forest and field sits a modest ranch home that is simplistic in style but overflowing with warmth and contentment. Loved for 40k+ years, it will be hard to turn over to its next denizen. The home is a time capsule of 70's charm and with some updating, can be enhanced with a new timeless country feel. Bring your creativity to this lovely setting. The property is completed with Hubbard Brook meandering through along with parcels that might be subdivided off should you desire for others to set up their homestead. Showings are delayed until open house on Sunday, June 22nd from 10:30am until 1:30pm. NO DRIVE BYS. HOUSE CAN NOT BE SEEN FROM ROAD. See Listing Details & 30 images.
$289,900 $132 per sq.ft. Windsor VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 2196 | Acres: 1.14Listed on Tuesday Jun 3, 2025
Description: 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". See Listing Details & 25 images.
Under Contract
$255,000 $253 per sq.ft. Windsor VT Home »
4 Beds | 1 Baths | Total Sq. Ft. 1008 | Acres: 0.33Listed on Tuesday Apr 1, 2025
Description: 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. See Listing Details & 23 images.
$255,000 $146 per sq.ft. Windsor VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1743 | Acres: 0.08Listed on Saturday May 24, 2025
Description: 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. See Listing Details & 18 images.
$195,000 $49 per sq.ft. Windsor VT Home »
5 Beds | 4 Baths | Total Sq. Ft. 4011 | Acres: 0.34Listed on Tuesday May 23, 2023
Description: 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. See Listing Details & 4 images.
Under Contract
$94,900 $144 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 660 | Acres: 0.18Listed on Friday May 16, 2025
Description: "Highest & Best Offer" deadline for submission is 10am EDT, Friday 5/23. This property is eligible under the Freddie Mac First Look Initiative through 06/15/2025. This property is offered 'as is'. Seller has not occupied property therefore there are no 'disclosures' offered. Interior ceiling damage(s) caused by roof 'failure' but half of roof was covered with corrugated metal by previous owner. Mold/damaged sheetrock & insulation already removed. House 'froze' & was defrosted, no water damage, winterized & that is current condition of plumbing/HVAC. Garage is salvageable but will require framing/etc. repairs. See Listing Details & 26 images.
