$269,000 $108 per sq.ft. Bennington VT »

Number of Units 1   Total Sq. Ft. 2500  |  Acres: 0.04
Under Contract List Date Monday Sep 15, 2025
Description: Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a prime spot to establish or expand your business. Upstairs, you'll find a generously sized 2-3 bedroom, 1 bathroom apartment spanning approximately 1,250 square feet. Whether you choose to live above your business or rent it out for additional income, the upper-level unit offers comfort and flexibility with plenty of natural light and charm. This property is perfect for an entrepreneur looking to live and work in the same location or an investor seeking strong rental potential in a vibrant downtown setting. See MLS Property & Listing Details & 15 images.

$399,000 $77 per sq.ft. Bennington VT »

Price Change! Reduced by $16,000 down 4% on March 9th 2026
Number of Units 4   Total Sq. Ft. 5208  |  Acres: 0.63
Under Contract List Date Friday Oct 3, 2025
Description: Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property's historic character, while modern updates support comfortable living and reliable income potential. Situated on a 0.63-acre lot with ample parking and room for future expansion or additional development. A rare opportunity to own a piece of Bennington's history with strong rental appeal and endless versatility. Ideally located within walking distance of Bennington's vibrant downtown shops, restaurants and community services--offering exceptional convenience for residents and strong visibility for commercial tenants. See MLS Property & Listing Details & 29 images.

$399,999 $305 per sq.ft. Addison VT »

Price Change! Reduced by $50,001 down 13% on March 31st 2026
3 Beds | 1 Baths |   Total Sq. Ft. 1312  |  Acres: 10.2
List Date Wednesday Jan 7, 2026
Description: Newly renovated log cabin set on over 10 private acres, offering exceptional peace, privacy, and natural beauty. Tucked away in a serene country setting and bordering state and agricultural land, this beautifully updated lodge-style home provides a rare blend of tranquility and modern comfort. Recent improvements include all new flooring throughout, updated bedrooms and closets, a fully renovated bathroom with new vanity, and a custom kitchen and dining area featuring bamboo cabinetry, countertops, and a built-in bar. Interior log walls have been professionally sanded and sealed, while the exterior logs have been freshly stained and sealed for long-lasting protection. Additional upgrades include a new window in the primary bedroom, a maintained roof with aluminum coating, and efficient year-round comfort provided by a Mr. Cool mini-split heat pump paired with a Harman pellet stove. Outside, enjoy a large detached garage/workshop, ideal for hobbies, storage, or a small business, along with a serene front porch perfect for relaxing and taking in the surrounding nature. Whether you're seeking a peaceful getaway, a private homestead, or a full-time residence, this move-in-ready property offers endless possibilities See MLS Property & Listing Details & 17 images.

$449,000 $135 per sq.ft. Brandon VT »

Number of Units 3   Total Sq. Ft. 3323  |  Acres: 2.04
List Date Thursday Jan 22, 2026
Description: Well-located mixed-use investment property along the Route 7 corridor, equidistant between Middlebury and Rutland and just minutes from downtown Brandon. The main building features a street-level commercial space currently operating as a successful yoga/pilates studio (with specialized heating for hot yoga), offering excellent visibility and ample on-site parking. Residential components include a two-bedroom apartment (7 total rooms) in the main building and a detached garage with a one-bedroom studio apartment above, providing multiple income streams and flexible use options. The property offers sunset views and a peaceful setting with a cemetery across the street, while remaining conveniently close to Brandon's shops, dining, and community amenities. Ideal for investors seeking a combination of commercial and residential income in a central Vermont location or an owner-occupied property with help carrying the costs by supplementing with rental income. Maybe you're looking for a recreational get-away? A property that allows you a home-away-from-home with easy access to places like Killington/Pico, Okemo, Stowe, Rikert Touring Center or miles of paved and gravel roads nearby for biking and plenty of peaks to climb! Room and bathroom counts, as well as square footage totals on this listing are for all three units. Main Apt: 2 bedrooms (one is on main floor) and an office with a closet, 3/4 bath, full bath, kitchen, living, dining and family room. Studio: studio space, body work room, entry, changing rooms, shower stall is separate from the 1/2 bath. Garage studio apt above 2 bay heated garage: kitchen, living area, bedroom area and 3/4 bath. Rents are currently below fair market rent but the residential tenants will be moving soon so there is opportunity to increase cash flow. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$295,000 $146 per sq.ft. Bennington VT »

Number of Units 2   Total Sq. Ft. 2022  |  Acres: 0.56
List Date Wednesday Apr 1, 2026
Description: Don't miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups--perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With a level lot just over half-acre, off-street parking, and 1 car garage/barn with additional storage, plus a prime location near downtown shops and restaurants, this is an ideal opportunity for both investors and owner-occupants! See MLS Property & Listing Details & 13 images.

$289,000 $115 per sq.ft. Bennington VT »

Number of Units 2   Total Sq. Ft. 2520  |  Acres: 0.2
List Date Thursday Apr 2, 2026
Description: Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout. Both units benefit from separate utilities, dedicated basement and attic storage, and four off-street parking spaces--rare and valuable amenities that enhance everyday livability and long-term investment performance. Ideally located just minutes from downtown Bennington, enjoy convenient access to local shops, dining, and community amenities. Commuters will appreciate being approximately one hour to Albany Airport and 3 hours to NYC and Boston. A turnkey, low-maintenance asset with strong fundamentals, flexibility, and future upside--this is a standout opportunity in today's market. See MLS Property & Listing Details & 40 images.

$275,000 $164 per sq.ft. Bennington VT »

Number of Units 2   Total Sq. Ft. 1680  |  Acres: 0.12
List Date Monday Jan 5, 2026
Description: Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a wide range of commercial uses including retail, food and beverage, office, studio, and personal services. The second-floor apartment, renovated by a prior owner approximately 10 years ago, provides comfortable living space ideal for an owner-occupant or steady rental income. The first floor and basement, formerly home to a long-standing florist shop, now offer a bright, open layout with the removal of the walk-in cooler--making the space feel larger and more adaptable than ever. Recent updates include fresh paint, new flooring, LED lighting, and a convenient half bath. For investors or those seeking a full residential conversion, the layout and separate entrances offer a clear opportunity to reconfigure the first floor into a second living unit, establishing a true duplex. The basement adds valuable storage with built-in shelving, while the walk-up attic offers additional storage or future expansion potential. Additional features include separate electric meters, shared boiler and oil tank (both replaced in 2020), vinyl siding and windows, architectural shingle roof, town water and sewer, and high-speed internet. Off-street parking for both units enhances functionality. Situated along one of North Street's most traveled corridors, the property benefits from excellent visibility, signage potential, and proximity to established neighbors like Blue Benn Diner, Wassick's Tire Service, and the Vermont Veterans Home. Whether you're looking for an investment property, live/work setup, or a redevelopment opportunity, this flexible property is ready to meet your vision. See MLS Property & Listing Details & 32 images.