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    Chester, CT Short Term Rental Properties for Sale

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    Deep River, CT Essex, CT Clinton, CT
    Mixed-Use Building in Downtown Chester
    $1,200,000
    3,000 SF

    Mixed-Use Building in Downtown Chester

    21 Main Street, Chester, CT 6412

    Prime mixed-use property in the heart of downtown Chester.

    • Prime downtown Chester location with high visibility and foot traffic.
    • Successful street‑level art gallery with 17 years of operation.
    • Profitable, fully furnished upper‑level short‑term rental.
    • Flexible mixed‑use zoning (retail, gallery, studio, office, live‑work).
    • Historic 1830 building with unique charm.
    Updated: Jan 1
    View details
    Based on your search, we've compiled 5 Potential Opportunities for your consideration. Besides 1 Active listings in Chester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Opportunities in Nearby Cities

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

    East Haddam Mixed-Use Opportunity
    $450,000

    East Haddam Mixed-Use Opportunity

    Unique mixed-use property in East Haddam Village near local attractions.

    5 Norwich Rd, East Haddam, CT 6423
    View details
    East Haddam Mixed-Use Property
    Contact for pricing
    3,708 SF

    East Haddam Mixed-Use Property

    Unique mixed-use property in East Haddam Village with income potential.

    5 Norwich Road, East Haddam, CT 6423
    View details
    Montauk Manor Condotel with Views
    $845,000
    745 SF

    Montauk Manor Condotel with Views

    One-bedroom duplex with water views and rental income potential.

    236 Edgemere Street, Montauk, NY 11954
    View details
    Montauk Manor Corner Suite
    $375,000
    626 SF

    Montauk Manor Corner Suite

    Corner one-bedroom suite with resort amenities and ocean views.

    236 Edgemere Street, Montauk, NY 11954
    View details

    Chester, CT Short Term Rental Properties Investment Opportunities Market Analysis

    Explore 1 short term rental properties for sale in Chester, CT on our real estate platform. These investment opportunities span a total of 3,000 square feet of properties for sale, with an estimated market value of $1,200,000.

    Sale prices for short term rental properties in Chester, CT start at $1,200,000, averaging $1,200,000, and reaching up to $1,200,000 — 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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    Operating Costs & Financing

    Average Loan-to-Value is 65.0%.

    Effective Property Tax $57.50 per sq ft
    Tax Rate (average for all types) 2.95%
    Avg Loan-to-Value 65.0%

    New Listings Trend, 12 Mo

    Number of new listings by month over the past year in Chester.

    Leading Commercial Asset Segments

    Short term rental properties 1

    Chester Demographics Overview

    Population 3,786
    Population Growth (5Y) -11.3%
    Median Household Income $94,570
    College Educated 64.1%

    Top Neighborhoods for Investment

    Discover the areas of Chester with the highest concentration of for-sale assets and compare their average market prices.

    Neighborhood Price Range Average Price
    06412 $975K - 4.2M $2.6M

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