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    Windsor County, VT Specialty Properties for Sale

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    6 properties
    Historic Bed & Breakfast Estate
    Updated: Jul 31
    Historic Bed & Breakfast Estate

    1589 Main Street, Cavendish, VT 05142

    $1,400,000
    2.40 AC lot
    2.4+/- landscaped acres in Cavendish, Vermont
    10‑bedroom mansion dating to 1860
    Five bedrooms with ensuite baths plus a private owner’s apartment
    Renovated 3,000‑square‑foot barn for events of up to 125 guests
    Listed on the National Historic Register
    View details
    Historic Bed And Breakfast Estate
    Updated: Aug 8
    Historic Bed And Breakfast Estate

    1589 Main St, Cavendish, VT 05142

    $1,400,000
    5,500 sqft 2.40 AC lot
    10‑bedroom mansion on 2.4± landscaped acres, listed on the National Historic Register
    Five bedrooms include ensuite baths; owner’s apartment provides a separate private living area
    Renovated 3,000‑square‑foot barn accommodates events for up to 125 guests
    Fully equipped chef’s kitchen designed for restaurant‑scale culinary preparation
    Lower‑level English‑style pub with full bar and pool table
    View details
    Specialty Property For Sale
    Specialty Property For Sale

    1 Depot St, Hartford, VT 05088

    $999,500
    0.50 AC lot

    Specialty property available for sale.

    View details
    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    Chester VT Specialty Property
    Chester VT Specialty Property

    3630 Vt Route 103 N, Chester, VT 05143

    $650,000
    2.00 AC lot

    Specialty property for sale in Chester, Vermont.

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    Hartford, VT Property For Sale
    Hartford, VT Property For Sale

    40 Union St, Hartford, VT 05001

    $329,000
    0.20 AC lot

    Property for sale in Hartford, Vermont.

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    Hartland Specialty Property For Sale
    Hartland Specialty Property For Sale

    282 Skunk Hollow Rd, Hartland, VT 05048

    $452,600
    1.00 AC lot

    Specialty property available for purchase in Hartland, Vermont.

    View details
    Based on your search, we've compiled 23 Potential Opportunities for your consideration. Besides 6 Active listings in Windsor County, VT, we suggest exploring several alternatives: similar 16 Off-Market properties to explore as potential leads, plus 1 Land Listings that present a potential for development.

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Five Acre Lot Near Trail
    Five Acre Lot Near Trail

    275 Mica Mine Rd, Claremont, NH 03743

    Contact for pricing
    5.00 AC lot

    Five acre lot abutting Unity Mountain Trail Conservation Area.

    View details

    Off-Market Properties in Windsor County, VT

    Consider similar Off-Market properties in Windsor County, 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.

    2326 Us Rte 5th N
    VETERINARY, ANIMAL HOSPITAL

    2326 Us Rte 5th N, Windsor, VT 05089-9061

    Estimated value:
    $315,000
    5,766 sqft 0.81 AC lot
    View details
    35 Depot St
    FUNERAL HOME

    35 Depot St, Chester, VT 05143

    Estimated value:
    $75,000
    5,270 sqft 0.50 AC lot
    View details
    20 Cmn St
    CHARITABLE ORGANIZATION

    20 Cmn St, Chester, VT 05143

    Estimated value:
    $255,000
    3,961 sqft 0.10 AC lot
    View details
    319 Main St
    VETERINARY, ANIMAL HOSPITAL

    319 Main St, Chester, VT 05143-0018

    Estimated value:
    $510,000
    3,864 sqft 8.76 AC lot
    View details
    4 Dunham Ave
    CHARITABLE ORGANIZATION

    4 Dunham Ave, Windsor, VT 05089-1510

    Estimated value:
    $270,000
    6,398 sqft 0.80 AC lot
    View details
    20 Brg St
    DAY CARE, PRE-SCHOOL

    20 Brg St, Windsor, VT 05089-1419

    Estimated value:
    $270,000
    2,968 sqft 0.56 AC lot
    View details
    65 Ascutney St
    FUNERAL HOME

    65 Ascutney St, Windsor, VT 05089-1720

    Estimated value:
    $275,000
    3,644 sqft
    View details
    40 Summer St
    CHARITABLE ORGANIZATION

    40 Summer St, Springfield, VT 05156-3737

    Estimated value:
    $225,000
    1.00 AC lot
    View details
    5 Brg St
    CHARITABLE ORGANIZATION

    5 Brg St, South Royalton, VT 05068

    Estimated value:
    $250,000
    880 sqft 0.50 AC lot
    View details
    7137 Us Rte 4 Rte
    Land

    7137 Us Rte 4 Rte, Bridgewater, VT 05034

    Estimated value:
    by Request
    View details
    982 Rte 100
    CHARITABLE ORGANIZATION

    982 Rte 100, Weston, VT 05161-5414

    Estimated value:
    by Request
    2,640 sqft 2.60 AC lot
    View details
    Riv St
    CHARITABLE ORGANIZATION

    Riv St, Springfield, VT 05156

    Estimated value:
    $230,000
    6.00 AC lot
    View details
    30 Pleasant St
    CHARITABLE ORGANIZATION

    30 Pleasant St, Springfield, VT 05156-2614

    Estimated value:
    $180,000
    1.00 AC lot
    View details
    Trailside Rd
    PROFESSIONAL CLUBS/ASSOCIATIONS

    Trailside Rd, Ludlow, VT 05149

    Estimated value:
    $355,000
    11.75 AC lot
    View details
    32 Rose Hl Rd
    FUNERAL HOME

    32 Rose Hl Rd, Woodstock, VT 05091-1083

    Estimated value:
    $295,000
    4,648 sqft 1.25 AC lot
    View details
    129 Vt Rte 100a
    CHARITABLE ORGANIZATION

    129 Vt Rte 100a, Bridgewater, VT 05034

    Estimated value:
    $255,000
    3,917 sqft 0.25 AC lot
    View details

    Windsor County, VT Specialty Properties Market Trends and Statistics

    Explore 22 specialty properties for sale in Windsor County, VT, showcased through 6 active listings on our real estate platform. These investment opportunities span a total of 5,500 square feet of properties for sale, with an estimated market value of $5,231,100.

    Sale prices for properties in Windsor County, VT start at $329,000, averaging $871,850, and reaching up to $1,400,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Featured Windsor County Real Estate Agencies

    Realmo connects you with licensed Windsor County CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Dunrovin Real Estate
    PO Box 450 Royalton, VT 05068
    Phone: 18027637177
    dunrovincountryvermont.com
    Snyder Donegan Real Estate Group
    PO Box 161, 5 The Green West Woodstock, VT 05091
    Phone: 18024572600
    www.snyderdonegan.com
    Bassette Real Estate Group
    611 Route 12 Hartland, VT 05048
    Phone: 18024572244
    www.vermontcountryrealestate.com

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