Windsor Vermont Real Estate

Spacious and affordable 3-story dwelling in desirable Windsor. Buy it as a starter home, or take the opportunity for renovation and rental or resale. Pleasant stone landscaping in the yard. A kitchenette is found in the 3rd floor apartment (perhaps a rental unit or an in-law suite?) There's proximity to shopping (including a fine glass store, brewery, distillery, and jam shop), Amtrak, Mount Ascutney Hospital, and across the street from the Connecticut River!

Come check out this very cute diamond in the rough! This home offers 2 good sized bedrooms with huge closets and a primary with a deck off the bedroom, as well as potential for a en suite bathroom....Several possibilities for the downstairs as well....Along with a 2 car garage with possible furnace hook up and its own electrical panel. This property is convenient to in town amenities and all that Windsor has to offer!

Amazing opportunity to easily convert this 6 bedroom duplex into a single family home! Or, have a perfect in-law apartment. Great location across the street from Windsor High School and backing to Lake Runnemede! The yard has mature shade trees. With a little clearing, you may be able to have views of Lake Runnemede which is just down the hill from the house. There is a narrow strip of park land between the house and the lake. This home has strong bones, feels solid, and has level flooring which is rare for homes of this age. It is a tremendous value with so much potential - it just needs some cosmetic work to bring it up to date. There are hardwood floors under all carpeting with the exception of the 17' bedroom over the garage which is an addition. Deeded access to shared driveway. Downtown shops and restaurants are just a short .3 mile walk on sidewalks. Convenient location just 20 miles to both Lebanon and Hanover, NH. Mt. Ascutney Hospital is less than a mile. Nature enthusiasts will love easy access to the 5 miles of trails at Paradise Park just a half mile away. Neighboring Lake Runnemede is a birding hotspot with over 215 species of birds sighted and beautiful Mill Pond is just 1 mile. So many amenities for such a low price!

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.

Let this rooming house be your next great investment. 10 rooms, and a 2 bedroom apartment. Some long term renters. Rooms still available, and new boiler just installed.

OPEN HOUSE Saturday, June 15th 10-12 PM! Nestled on the edge of Windsor Village, this charming cape-style home has a well-maintained allure and picturesque appeal, inviting new homeowners to make it their own. A cobblestone chimney accents the exterior and a welcoming split rail fence adds to its quaint charm. Many new upgrades and features include a circular driveway, all new vinyl siding, new windows, and a private back patio deck. The driveway offers easy access to pull in & out, and ample parking space as well. The mudroom seamlessly connects to the kitchen, convenient for unloading your groceries, and unwind in the spacious and open concept living/dining room filled with natural light through large bay windows. Enjoy hardwood floors throughout and a classic stone fireplace could be revived for cozy evenings by the fire. The functional eat-in kitchen offers extra counter space, while a bonus room provides versatility as a den or office area. A front and back staircase ascend to four large bedrooms on the second floor, ensuring plenty of space for everyone. Outside, a large flat yard invites creativity, perfect for creating your ideal outdoor oasis, whether it's building a firepit for gatherings, playing or gardening. Walk to school, the Windsor Swim Area at Mill Pond, or explore the Windsor Fairgrounds and Paradise Park. With a short commute to Hanover, Lebanon, DHMC, and Dartmouth College, this move-in ready home offers great accessibility in one desirable package.

Now is your opportunity to own this renovated, well-cared-for 3-bedroom, 2-bathroom home on a spacious 1+ acre lot in a desirable cul-de-sac neighborhood. This home provides a split master bedroom from its secondary bedrooms, an open floor plan, and a secluded back patio to enjoy pleasant Vermont evenings outside. Renovations include - new vanities, appliances, toilets, and flooring, as well as fresh paint throughout. It also provides a large, unfinished basement, a blank canvas for your imagination, that can be used for storage or finished for even more square footage. This home is conveniently located minutes from shopping, dining, grocery, John P. Larkin Country Club/Golf Course, and Mt. Ascutney Hospital, to name a few. Don’t let this one pass you by. Schedule your private tour today!

Welcome to this well-maintained ranch located in the highly sought-after Juniper Terrace neighborhood. This delightful home features 3 cozy bedrooms and 1 full bath, perfect for comfortable living. The inviting living area is complemented by a pellet stove, providing warmth and ambiance during the cooler months. The highlight of this home is the finished basement, offering additional living space that can be customized to suit your needs—be it a family room, home office, or recreation area. The exterior is equally impressive with a well-manicured lawn and charming curb appeal. Don't miss the opportunity to make this lovely home yours. Schedule a showing today and experience the best of Juniper Terrace living! Open House Sunday June 23, 10-12noon

Price Just Improved! Discover your dream home nestled in a serene neighborhood! This charming 3-bedroom Cape Cod-style house sits on a spacious 1.15-acre lot adorned with delightful perennial gardens. Step inside to experience a cozy, yet spacious interior that seamlessly blends classic charm with modern comfort. The home features a thoughtfully designed layout, ideal for both relaxation and entertaining. Enjoy gatherings in the generous living areas, enclosed porch and expansive deck or retreat to the tranquil bedrooms for peace and quiet, complete with endless closet space. Convenience meets lifestyle with a one-car garage providing ample storage and parking space. Located just minutes from I-91, commuting is a breeze, while easy access to town amenities ensures you're never far from shopping, dining, and entertainment options. Don't miss your chance to own this exceptional property in a sought-after neighborhood. Schedule your private tour today and envision the possibilities of calling this house your new home.

Built in 1796, the historic Trask House is located on beautiful Main St. in the heart of downtown Windsor. The center hall Federal sits on just under 1/2 acre and has an attached barn/garage in the back with plenty of storage. There is a private brick patio surrounded by a white picket fence and lovely landscaping. Inside, you are greeted by large open rooms with hardwood floors, high ceilings, and multiple fireplaces. The updated kitchen is open to the dining room with a wood burning stove centered between the two rooms. The dining room leads to the stunning living room with picturesque alcoves and original Federal style millwork and mantels. Across the hall are the family room and a quaint library which ultimately connects back to the kitchen. A grand center hall stair case leads upstairs to 4 good sized bedrooms, a full bath and the laundry room. The Trask House is in an ideal location just minutes from Lake Runnemede, restaurants and stores, and Mt. Ascutney Hospital. Woodstock, Hanover, and the Upper Valley are approximately 25 minutes away. The Trask House is in the National Registry of Historic Homes and has been featured in numerous books on historic homes of New England. Come take a look!

Welcome to this exquisite four-bedroom, two-bathroom Colonial home, built in 1801, nestled on a sprawling 10.4-acre lot in Windsor, Vermont. This charming residence boasts maple and bamboo floors as well as original wide pine flooring, spacious bedrooms, and tiled bathrooms. The property includes a two-bedroom, one-bathroom ADU, perfect for generating rental income or accommodating guests. Enjoy the serene rural setting with level land ideal for animals, fenced pastures, and extensive perennial gardens. Outdoor amenities include a glamping site over the barn, RV hookups, an in-ground pool, and a tranquil majestic pond surround by natural iris that bloom every spring. Recent updates blend historic charm with modern appointments, maintaining the home beautifully for 30 years under the same owner. Located close to local amenities, this home offers both seclusion and convenience. Additional features include outbuildings and an animal barn, providing ample storage and versatile use. Don't miss this unique opportunity to own a piece of Vermont history with endless potential.

Fox Penny Farm, an established horse farm on 62 acres of open fields, trails, and woods on the Windsor/West Windsor line with westerly views of Mt Ascutney, is now offered for sale. Offering an expansive 3-bedroom 2.5 baths colonial with light-filled spaces, hardwood floors, spacious kitchen, dining room & propane fireplaced living room. Upstairs provides three large bedrooms with a primary ensuite. The lower level offers a partially finished living area with a wood stove and French doors leading to a private deck. Complete with 36x50 5-stall barn, 1000 bale hay storage heated tack room, and wash stall. Multiple run-in sheds, fenced paddocks, 100’ x 200 outdoor arena, equipment shed, and workshop with woodstove, all on open flat land. Fully wired generator servicing the house, barn, and outbuildings. Easily adaptable for farming pursuits. Prime location for hiking, biking, and skiing. Easily accessible to Woodstock & the Upper Valley. A special property that must be seen to appreciate all the possibilities.