Windsor, VT Real Estate

MLS Number 4946823

• Commercial
• Address 26 Depot Street
• Year Built 1900
• Square Feet 2,888
• Acreage 0.31

Historic Masterpiece built in 1900. Windsor Station remained an active train station until the mid-sixties when the building was shuttered. In the mid-1970's a team leased the building from Central Vermont Railway and converted it into a restaurant. The restaurant changed hands in 1976 and was successfully run by the same family for 35 years. After changing hands again, the building was then abandoned in October of 2010. In April 2013 the current owner/operators rescued the then derelict property and made extensive renovations and added period decorations. Along with providing excellent food and service, they have turned the property into a thriving and successful operation. Amtrak service continues with the newly built platform alongside the building. The “Vermonter Train” runs from Washington D.C. to St. Albans-Burlington, VT passing through Baltimore, NYC, Philadelphia along the way. The Southbound train stops at Windsor Station around noon and the Northbound stops around 6pm to the delight of the diners. Step inside this epic station and it will take you back to a different era. Windsor Station Restaurant is the pulse of the Town. Excellent growth potential with lunch and brunch services. Currently in construction is a beautiful 4 acre park across the tracks and a 35 unit apt building up the street. Buyers will be asked to fill out a Prospect Package before receiving the financials. Numbers support the price. Owners are only interested in talking with Qualified Buyers.

Listed by Dick Palmer of Hospitality Consultants,LLC

MLS Number 5018205

• Residential Single Family
• Full Bath 3
• Address 30 Union Street
• Construction Existing
• Bedrooms 4

Step into timeless elegance with this grand Victorian home, beautifully situated on a charming in-town lot. This stately residence showcases stunning hardwood floors throughout, preserving its classic heritage while offering modern comforts. The spacious first-floor bedroom features an en suite bath, providing both luxury and convenience. A cozy fireplace adds warmth and character to the main living space, perfect for relaxing evenings. The 2nd floor has more ensuite bedoom options, a second living room and even a wet bar, or send your food up in the dumbwaiter. The home boasts a generously-sized walk-in pantry, ideal for storage and organization. An added bonus is the potential separate apartment, offering endless possibilities for rental income, guest accommodations, or an in-law suite. Completing the property is a two-car detached garage, providing ample storage and parking. This house will suit a buyer who hopes to fill it's halls, expand, or be a welcome haven for a family compound. Minutes into downtown Windsor, an easy jaunt to the K-12 school, and a stones throw away from the Recreation Center makes for flexibility if transportation is an issue. Or...let's consider the potential for a home business or commercial opportunity with a change of use permit. 6 additional spaces in the back, add ample parking. 2-3 office spaces and a 1/2 on main level and excellent street visibility. Property is located in the CENTRAL BUSINESS DISTRICT. Come make this one your own!

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

MLS Number 5028181

• Multifamily
• Address 102-104 State Street
• Units 4
• Bathroom 4
• Acreage 0.38

INVESTMENT PROPERTY. 4 UNITS, 1 1-bedroom unit & 3 2-bedroom units. Separate basement for each unit. Recent improvement includes, new roof, replaced plywood, foam board and membrane, at a cost of $70,600.00. Heat is separate pellet stoves for each unit, also an oil-fired steam system if needed for backup. Electric is separate, tenants pay electric. Landlord pays heat. Minimum of 48-hour required notice to give tenants notice to show.

Listed by Don Chabot of Town and Country Realty

MLS Number 5000223

• Condo
• Square Feet 2,052
• Bedrooms 3
• New Contruction Existing
• Complex Old Mill Pond

Old Mill Pond Condominiums offer an idyllic haven in the heart of Windsor. Imagine enjoying mountain views, pond access, and amenities such as an in-ground pool and tennis courts. This unit features vaulted ceilings and unique architectural elements often missing in typical condominiums. Guests can relax by the cozy fireplace or on the spacious deck with mountain views, depending on the season. Year-round convenience is assured with an attached garage, ample storage, and a functional layout. The unit includes three bedrooms, each with an ensuite bath-one of which includes a delightful jacuzzi tub. Includes an additional 4th sleeping space with a 3/4 bath and kitchenette space. For those seeking easy living, this move-in ready unit within an impeccably maintained condo association is hard to beat!

Listed by Julie Davis of KW Vermont Woodstock

MLS Number 5032968

• Residential Single Family
• Full Bath 1
• Address 42 Elm Street
• Construction Existing
• Bedrooms 3

OFFER DEADLINE: 3/27/2025 at 2pm. Nestled in the heart of Windsor, VT, this delightful 3-bedroom, 2-bathroom home offers classic New England charm with many recent renovations. Situated in a desirable in-town location, this two-story home boasts a welcoming front porch, perfect for relaxing with your morning coffee. Inside, you'll find a warm and inviting layout. The entry way provides a place for pantry items, outdoor gear, extra appliances, and a newly renovated 3/4 bath. The kitchen is new and bright and offers a nice work area. There is formal dining which leads into an open living room that connects to the front enclosed porch. Upstairs, you'll find 3 bedrooms and a full bath. A one-car garage provides convenient parking and storage. With easy access to local shops, dining, and amenities, this home is a fantastic opportunity for those seeking a blend of small-town living and modern comfort. Don't miss your chance to make this Windsor gem your own! Open House Sunday 3/23/25 10-12noon.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

MLS Number 5030090

• Residential Single Family
• Full Bath 1
• Address 43 River Street
• Construction Existing
• Bedrooms 4

Charming & spacious home with timeless character. Step into a home where classic charm meets modern convenience! From the moment you enter, you'll be captivated by the warmth of the hardwood floors, wide trim, built-ins, and soaring ceilings that create an inviting and spacious atmosphere. The generously sized rooms effortlessly accommodate daily life, while the enclosed three-season porch beckons for cozy gatherings, a quiet morning coffee, or peaceful relaxation with a Spring breeze blowing in. This home offers endless possibilities with an unfinished bonus space-perfect for creating a home office, studio, or additional living area tailored to your needs. Upstairs, three spacious bedrooms and a full bath are complemented by second-floor laundry for added convenience. And just wait until you see the attic space that adds even more potential to this already impressive home. With many great upgrades since 2014 and two large outbuildings, there's no shortage of storage or workspace. Don't miss your chance to own this one-of-a-kind property-schedule your showing today! Showings begin Tuesday 2/25/2025.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

MLS Number 4953869

• Residential Single Family
• Full Bath 3
• Address 70-74 State Street
• Construction Existing
• Bedrooms 5

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.

Listed by Wade Treadway of Wade I Treadway Real Estate

MLS Number 5022787

• CommercialLease
• Lease 14
• Address 105 Main Street

3,858 sq. ft. of prime office space above Mascoma Bank with double sided elevator service. Includes the entire second floor and is divided for 2 separate private office areas that include several private offices, and open workspace areas. 2 baths, large conference room. Front and rear entrances and exits. Ample parking. Heat and rubbish removal included in rent. July 1, 2025 occupancy.

Listed by Don Chabot of Town and Country Realty