Advertise
    Chester, VT
    For Sale
    • For Sale
    • For Lease
    • Recently Sold
    • Property Lookup
    • Brokers
    Property Types
    • Retail
    • Office
    • Residential Income
    • Restaurants
    • Industrial
    • Warehouse
    • Mixed-Use
    • Hospitality
    • Health Care
    • Sports & Entertainment
    • Land
    • Agricultural
    • Parking & Garage
    • Specialty
    Price
    Price
    $
    $

    Chester, VT Commercial Real Estate for Sale

    Notify Me
    List
    Map
    Grafton, VT Springfield, VT Rockingham, VT
    8 listings
    Triplex with Roadside Parking
    $295,000
    2,702 SF
    Triplex with Roadside Parking

    41 VT Route 103 S, Chester, VT 05143

    Triplex on busy Route 103 with good road frontage and flexibility for an owner-occupied business office.
    • Wood frame building with shingle roof and natural gas heating
    • Built in 1900 and served by public water; cable available
    • Three existing units: live/work with one unit for an office and rent the other two apartments
    • Located on Chester’s busy Main Street (Route 103 and Route 11) with good road frontage
    • Situated between the Jiffy Mart and the General Dollar store
    Updated: Nov 19, 2025
    View details
    Iconic Fullerton Inn For Sale
    $1,495,000
    18,896 SF
    Iconic Fullerton Inn For Sale

    40 The Common, Chester, VT 5143

    Southern Vermont hospitality landmark in historic downtown Chester.
    • Iconic, fully established turnkey inn business in historic downtown Chester.
    • Prime location on 2.28 acres with Williams River access.
    • 20 guest rooms/suites plus two owner/manager apartments.
    • Multiple dining areas (main dining room, secondary dining area, tavern/bar) and large rear deck.
    • Professional commercial kitchen for full restaurant operation and catered events.
    Updated: Apr 26
    View details
    Renovated Mixed-Use Property
    $650,000
    5,324 SF
    Renovated Mixed-Use Property

    Completely renovated two-unit residence plus a two-story commercial space, offering flexible options for occupancy or leasing.

    3630 Vt Route 103 N, Chester, VT 5143

    View details
    Open Meadow Agricultural Land Parcel
    $159,000
    5.00 Acres
    Open Meadow Agricultural Land Parcel

    Five-acre parcel with an open meadow, town road access, power nearby, and a WWW permit already issued.

    Contro Road, Chester, VT 05143

    View details
    Mountain View Agricultural Land Parcel
    $249,000
    84.00 Acres
    Mountain View Agricultural Land Parcel

    84+ acres with over 3,000 feet of road frontage, mountain views, and utilities access for agricultural or recreation use.

    Green Mountain Turnpike, Chester, VT 05143

    View details
    Vermont Land with Mountain Views
    $249,000
    84.00 Acres
    Vermont Land with Mountain Views

    84 acres of Vermont land with development potential.

    000 Green Mountain Turnpike, Chester, VT 5143

    View details
    Flexible Retail or Workshop Building
    $164,000
    2,400 SF
    Flexible Retail or Workshop Building

    A former Grange building with open interior, kitchen and bathroom, and wheelchair accessibility along a well-traveled road.

    3553 Vt Route 103 N, Chester, VT 5143

    View details
    Commercial Property with Rail Siding
    $425,000
    6,656 SF
    Commercial Property with Rail Siding

    Versatile commercial property featuring office, garage, and rail access.

    134 Gold River Extension Unit 1A1, Chester, VT 05143

    View details
    Based on your search, we've compiled 76 Potential Opportunities for your consideration. Besides 8 Active listings in Chester, VT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 64 Off-Market properties to explore as potential leads

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Gambrel-Style Multi-Family Property
    $800,000
    4,733 SF
    Gambrel-Style Multi-Family Property

    Spacious gambrel-style home with an additional rented modular unit, set on 9.55 acres in Springfield, Vermont.

    107-109 Baker Road, Springfield, VT 05156

    View details
    Historic Schoolhouse with Modern Potential
    $699,000
    3.70 Acres
    Historic Schoolhouse with Modern Potential

    1862 schoolhouse reimagined for commercial or residential use.

    66 Duttonsville School Drive, Cavendish, VT 05142

    View details
    Historic Firehouse Live-Work Space
    $125,000
    Historic Firehouse Live-Work Space

    Historic firehouse offers flexible space for business, living quarters, or both near the Proctorsville Green.

    406 Main Street, Cavendish, VT 5142

    View details
    Glamping Campground with Farm Buildings
    $985,000
    10.00 Acres
    Glamping Campground with Farm Buildings

    Fully permitted glamping grounds on 10 acres with a restored farmhouse, bath house, and multiple on-site structures.

    481 Parker Hill Rd, Springfield, VT 5156

    View details

    Off-Market Properties in Chester, VT

    Consider similar Off-Market properties in Chester, VT. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    136 Main St
    COMMERCIAL (GENERAL)
    Lot: 0.66 Acres

    136 Main St, Chester, VT 05143

    View details
    26 Main St
    OFFICE (GENERAL)
    2,562 SF Lot: 0.75 Acres
    Value Estimation by Request

    26 Main St, Chester, VT 05143-9357

    View details
    2739 Vt Rte 11th E
    COMMERCIAL (GENERAL)
    800 SF Lot: 3.50 Acres
    Value Estimation by Request

    2739 Vt Rte 11th E, Chester, VT 05143

    View details
    15 Depot St
    COMMERCIAL (GENERAL)
    4,493 SF Lot: 0.12 Acres
    Estimated value
    $535,000

    15 Depot St, Chester, VT 05143

    View details
    2350 Vt Rte 10
    OFFICE/RESIDENTIAL (MIXED USE)
    1,876 SF Lot: 10.90 Acres
    Value Estimation by Request

    2350 Vt Rte 10, Chester, VT 05143-9636

    View details
    472 Main St
    COMMERCIAL (GENERAL)
    5,546 SF Lot: 1.00 Acre
    Value Estimation by Request

    472 Main St, Chester, VT 05143-9361

    View details
    442 Elm St
    COMMERCIAL (GENERAL)
    1,488 SF Lot: 0.25 Acres
    Value Estimation by Request

    442 Elm St, Chester, VT 05143-9290

    View details
    117 Main St
    OFFICE/RESIDENTIAL (MIXED USE)
    2,008 SF Lot: 0.75 Acres
    Value Estimation by Request

    117 Main St, Chester, VT 05143-9620

    View details
    6802 Popple Dungeon Rd
    SHOW ROOM, WAREHOUSE
    Lot: 105.26 Acres
    Estimated value
    $560,000

    6802 Popple Dungeon Rd, Chester, VT 05143-9825

    View details
    12 Cmn St
    STORE/OFFICE (MIXED USE)
    4,060 SF Lot: 0.25 Acres
    Value Estimation by Request

    12 Cmn St, Chester, VT 05143

    View details
    173 Horsenail Hl Rd
    COMMERCIAL (GENERAL)
    Lot: 36.25 Acres
    Value Estimation by Request

    173 Horsenail Hl Rd, Chester, VT 05143

    View details
    665 Vt Rte 10
    COMMERCIAL (GENERAL)
    4,674 SF Lot: 10.25 Acres
    Estimated value
    $585,000

    665 Vt Rte 10, Chester, VT 05143-9656

    View details
    Grafton St
    INDUSTRIAL (GENERAL)
    Lot: 3.29 Acres
    Value Estimation by Request

    Grafton St, Chester, VT 05143

    View details
    Taylor Hl
    INDUSTRIAL (GENERAL)
    Lot: 64.00 Acres
    Value Estimation by Request

    Taylor Hl, Chester, VT 05143

    View details
    2490 Flamstead Rd
    INDUSTRIAL (GENERAL)
    Lot: 4.00 Acres
    Value Estimation by Request

    2490 Flamstead Rd, Chester, VT 05143-8889

    View details
    81 Gold Riv Ext
    COMMERCIAL (GENERAL)
    Lot: 1.95 Acres
    Value Estimation by Request

    81 Gold Riv Ext, Chester, VT 05143-0017

    View details

    Chester, VT Commercial Real Estate Market Trends and Statistics

    Explore 72 commercial real estate for sale in Chester, VT, showcased through 8 active listings on our real estate platform. These investment opportunities span a total of 35,978 square feet of properties for sale, with an estimated market value of $3,029,000.

    Sale prices for business properties in Chester, VT start at $164,000, averaging $605,800, and reaching up to $1,495,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

    List
    Map

    Demographics Overview

    Population 4,916
    Population Growth (5Y) +12.0%
    Median Household Income $73,438
    College Educated 24.4%

    High-Yield Neighborhoods for Investment

    Identify Chester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

    Neighborhood Average Price
    05143 $479.5K

    Taxes & Financing

    Tax Rate (average for all types) 2.38%
    Property Tax per SF $59.56 per SF
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Windsor County

    New Delisted

    Total CRE Inventory on Market (SF)

    Need Help?

    Reach out if you need assistance with Realmo tools or have questions about your listings

    Contact Us

    Browse Commercial real estate for Sale Near Chester, VT

    Popular Searches in Chester, VT

    Popular Categories

    Most Searched ZIP Codes in Chester, VT

    • 05143

    Select Neighborhood

    Google sign-in failed. Please try again or use another login method.
    Sign Up Successful!
    You now have access to more from Realmo!