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    Chester, VT Residential Income Properties for Sale

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    Grafton, VT Springfield, VT Rockingham, VT
    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
    Renovated Mixed-Use Property
    $650,000
    5,324 SF
    Renovated Mixed-Use Property

    3630 Vt Route 103 N, Chester, VT 5143

    Completely renovated two-unit residence plus a two-story commercial space, offering flexible options for occupancy or leasing.
    • Year built 1830, completely renovated property in Chester, VT
    • Two residential units with high‑quality upgrades throughout
    • New electrical, plumbing, insulation, and energy‑efficient windows
    • Two‑story commercial area included, currently occupied by an established business
    • Residential kitchens and bathrooms feature reclaimed materials in the renovations
    Updated: Jun 12
    View details
    Based on your search, we've compiled 20 Potential Opportunities for your consideration. Besides 2 Active listings in Chester, VT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 10 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    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
    Duplex with Barn and Flex Loft
    $525,000
    2,304 SF
    Duplex with Barn and Flex Loft

    Renovated 5-bedroom structure that can operate as two rental units, with an unfinished third floor and attached barn.

    81 High Street, Cavendish, VT 05142

    View details
    Multi-Family with Carriage House
    $249,000
    3,312 SF
    Multi-Family with Carriage House

    Residential income property with three 2-bedroom units plus a separate 2-bedroom carriage house.

    715-717 Giddings Street, Springfield, VT 05150

    View details
    Duplex with Barn and Third-Floor Potential
    $525,000
    2,304 SF
    Duplex with Barn and Third-Floor Potential

    Converted for flexible rental use with two units, plus an unfinished third floor and attached barn for storage.

    81 High Street, Cavendish, VT 5142

    View details

    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.

    Vermont Land with Building Potential
    $74,500
    16.24 Acres
    Vermont Land with Building Potential

    16.24 acre lot in Chester, VT, wooded and private.

    Farrar Road, Chester, VT 05143

    View details
    Vermont Land with Mountain Views
    $229,000
    27.80 Acres
    Vermont Land with Mountain Views

    27.8 acre Chester, VT parcel with approved wastewater permit.

    Quarry Road, Chester, VT 05143

    View details
    Vermont Land with Mountain Views
    $229,000
    27.80 Acres
    Vermont Land with Mountain Views

    27.8 acre Chester, Vermont parcel with approved wastewater permit.

    00 Quarry 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

    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.

    418 Howard Hl Rd
    CAMPGROUND, RV PARK
    Lot: 1.40 Acres
    Value Estimation by Request

    418 Howard Hl Rd, Chester, VT 05143-4474

    View details
    982 High St
    CAMPGROUND, RV PARK
    952 SF Lot: 115.59 Acres
    Value Estimation by Request

    982 High St, Chester, VT 05143

    View details
    Andover Rd
    CAMPGROUND, RV PARK
    Lot: 6.62 Acres
    Value Estimation by Request

    Andover Rd, Chester, VT 05143

    View details
    Potash Brk Rd
    CAMPGROUND, RV PARK
    Lot: 10.50 Acres
    Value Estimation by Request

    Potash Brk Rd, Chester, VT 05143

    View details
    6558 Popple Dungeon Rd
    CAMPGROUND, RV PARK
    Lot: 0.23 Acres
    Value Estimation by Request

    6558 Popple Dungeon Rd, Chester, VT 05143

    View details
    Whitmore Brk Rd
    Farms
    Lot: 18.54 Acres
    Value Estimation by Request
    Whitmore Brk Rd

    0 Whitmore Brk Rd, Chester, VT 05143

    View details
    Howard Hill Rd
    Land
    Lot: 200.27 Acres
    Value Estimation by Request
    Howard Hill Rd

    0 Howard Hill Rd, Chester, VT 05143

    View details
    173 Horse Hl Rd
    Farms
    Lot: 534.04 Acres
    Value Estimation by Request

    173 Horse Hl Rd, Chester, VT 05143

    View details
    270200 Old Shincracker
    CAMPGROUND, RV PARK
    Lot: 47.00 Acres
    Value Estimation by Request

    270200 Old Shincracker, Chester, VT 05143

    View details
    17 Pond Rd
    CAMPGROUND, RV PARK
    Lot: 1.67 Acres
    Value Estimation by Request

    17 Pond Rd, Chester, VT 05143

    View details

    Chester, VT Residential Income Properties Investment Opportunities Market Analysis

    Explore 12 residential income properties for sale in Chester, VT on our real estate platform. These investment opportunities span a total of 2,702 square feet of properties for sale, with an estimated market value of $295,000.

    Sale prices for residential income properties in Chester, VT start at $295,000, averaging $295,000, and reaching up to $295,000 — 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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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Multifamily properties 4
    Duplexes 3
    Triplexes 1

    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 $295K

    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)

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