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 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. 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 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 5022365

• Residential Single Family
• Full Bath 2
• Address 18 County Road
• Construction Existing
• Bedrooms 3

Enjoy all the conveniences of Village life, with a tranquil view of rolling green horse pastures right from your window. This absolutely-charming antique New Englander has one of the best locations in town. Just outside your back door you'll enter the 200 AC Paradise Park nature trail network, complete with ponds, waterfalls, vernal pools and wildlife. The house is tidy, efficient, and lovingly stewarded. Enter the rear mudroom with direct access to the bright kitchen and open concept dining room, with sliders to the spacious deck overlooking established perennial beds, fruit trees, mature plantings, and a huge flat yard for gardening and recreation. Livingroom, one bedroom and bathroom further complete the first floor. The second level has two more bedrooms, and a second bathroom with plenty of storage. The oversized 2-car garage barn has an enormous heated upper level (perfect for your studio or workshop). Showings begin Sunday @ Open House from 1-3.

Listed by Danny Kogut and Scott Monahan of Williamson Group Sothebys Intl. Realty

MLS Number 4999035

• Multifamily
• Address 12-14 State Street
• Units 4
• Acreage 0.03
• Square Feet 2,430

Rare Opportunity in the heart of Windsor, Vermont. This building contains 3 residential rental units and 1 additional unit that has been used as office space but can be converted into an additional residential unit with a permit. This originally balloon built property has had its foundation restabilized, new insulation, and almost 100% siding replaced. The first floor contains the office rental, Unit 1, Unit 2 access, and a common area/mailroom. Unit 1 contains a mudroom, kitchen/living room, bedroom, and bathroom. Unit 2, on the second floor, contains a kitchen, living room, bathroom, and two bedrooms. Unit 2 has high ceilings making the space feel open and spacious, with upgraded electrical throughout most of the building. Unit 3 is accessed by covered outdoor stairs to the third floor. This unit contains a small mudroom, kitchen/dining room, bathroom, and two bedrooms. Office space is currently an open office room with a private bathroom. Basement is dry and spacious, plenty of space for storage and/or laundry room. Seller has Lead Paint Certification. The location is right downtown! Café across the street and walking distance to shops, parking, laundry mat, school, and public transportation. Delayed showings until Thursday June 13th!

Listed by Cheryl Herrmann and Kelsey Herrmann-Satnzel of RE/MAX Group One Realtors

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 5015596

• Residential Single Family
• Full Bath 1
• Address 17 Dewey Avenue
• Construction Existing
• Bedrooms 3

Nicely located just walking distance to the school and town amenities. Nice level lot with home just waiting for you to make it your own. Three bedrooms and spacious main level.

Listed by Dorothy Griswold of The Clerkin Agency,P.C.

MLS Number 4998415

• Multifamily
• Address 153 Main Street
• Units 3
• Bathroom 3
• Acreage 0.14

As-Is Sale Only. Updated interior pics added.

Listed by Robert Balewicz of Evergreen Realty of Vermont

MLS Number 4985204

• CommercialLease
• Lease 3500
• Square Feet 2,450
• Year Built 1997
• Acreage 0.48

This Former McDonald's Restaurant is a Great Property for your Business. Situated Adjacent to a Plaza with Price Chopper, Aubuchon Hardware and Dollar General and Sited on Busy US Rte 5 only Minutes from Historic Windsor Means You Have Many Free Benefits. Being Well Maintained and with a Drive Thru Window, 14 Ft Ansul System Range Hood, Open Concept, and 2 ADA Rest Rooms Equates to an "Easy to Start Your Operations Property". Close to I-91 Access, Ski Areas, Golf Course, and Local Hospital and 20 Minutes to Hanover/Lebanon and Extra Benefits So Don't Wait on thie Unique Opportunity.

Listed by Brian Whipple of Coldwell Banker Homes Unlimited

MLS Number 5022787

• CommercialLease
• Lease 14

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