Windsor Vermont Real Estate

Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th.
"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.
Welcome to 517 Back Mountain Rd., Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th.
Welcome to 32 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th.
Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th.
Welcome to 84 Cubb Court, , Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-66 model manufactured home offers 3 bedrooms, 2 bathrooms, and 880 sq. ft. (13'4"x66) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient construction, modern appliances, and low-maintenance materials, making it perfect for easy living. Located in a peaceful and well-maintained community, this home is ideal for those looking for a move-in-ready option in a convenient location. Don’t miss out on this opportunity! Contact us today for more details or to schedule a tour. The interior is approximately 90% complete. Interior showings will be available beginning August 15th.
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.
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.
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.
Discover classic Vermont charm in this 3-bedroom, 1.5-bathroom home located on a quiet, tree-lined street just steps from downtown Windsor. This home is perfect for those who appreciate historic charm and are ready to make it their own. Inside, you’ll find a welcoming layout and abundant natural light. The first floor features a full bathroom, laundry, spacious living and dining areas, and an efficient kitchen ready for your personal touch. Upstairs, you’ll find three comfortable bedrooms and a convenient half bath. Enjoy mornings on the covered front, screened in porch and peaceful afternoons in the private side yard — perfect for a garden, play area, or simply relaxing in the shade. Located within walking distance to local shops, restaurants, schools, and parks, this property offers the best of Windsor’s vibrant community with easy access to I-91 and nearby Upper Valley amenities. Don’t miss your chance to make this inviting home your own!
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".
Welcome to this rejuvenated home with one car garage with recent updates including fresh paint and flooring, new kitchen counter tops and cabinets and light fixtures. There’s good interior space with a living room, dining room, family room, second floor laundry and 3 bedrooms upstairs as well as an enclosed front porch for evening relaxing. This is a great opportunity and should be on your short list!
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!
Extremely well maintained 3 bedroom / 2 bath ranch style home located in the Juniper Terrace neighborhood. The home offers a Buderus boiler, radiant floors, open floor plan with natural wood trim, wood floors in the main living area and a 2 flue chimney for woodstove hookup. Cooks will love the kitchen with its cherry cabinets, granite counters, stainless steel appliances, pantry and 5 burner propane stove. The dining area is open to the large living room and has a nice size slider that opens to the 10’ x 20’ deck with a power awning. The main bedroom has a private bath while the other two share a hallway bath equipped with both a shower and stackable washer / dryer. The oversized 2 car garage is just the ticket and offers direct access to the basement. While currently unfinished, the basement offers plenty of space for those who may want to finish in the future. Situated towards the back of the neighborhood, the property is more privately situated, level, nicely landscaped, spacious for kids and dogs to play or even put in a garden or two. Did we mention the 12’ x 13’ shed as well as a 21’ above ground pool? While currently not in use, the pool could be just the place to cool off on those warm sunny days. Located less than 4 miles from I-91, it is an easy commute to the Upper Valley. A great property and perfect for those looking for one level living. With its neighborhood setting, you will find it ideal for daily walks with the dog or just to get out and take a stroll.
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.
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 maintenance-free manufactured cedar-tone shingles on the entire house 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.

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