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    Woodstock, NY Short Term Rental Properties for Sale

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    Saugerties, NY Bearsville, NY Kingston, NY
    Woodstock Cottages: Investment Opportunity
    $1,995,000
    4,331 SF
    Woodstock Cottages: Investment Opportunity

    2465 Glasco Turnpike, Woodstock, NY 12498

    Five unique cottages on six wooded acres near Woodstock Village.
    • 5‑cottage property on 6 acres with a mix of short- and long‑term tenants, with the option to rent all five or live in one and rent the others
    • Short‑term rental license conveys; 2025 cap rate with all cottages rented was 7, and 2024 cap rate was closer to 10
    • Cottage 2 (1 bed/1 bath) was fully renovated in 2024
    • Cottage 4 (1 bed/2 baths) is wheelchair‑accessible, with an accessible approach with a ramp
    • Heating/cooling includes radiant floor and ductless systems; ENERGY STAR qualified appliances and ENERGY STAR qualified equipment are included
    Updated: May 18
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    Turnkey Woodstock Mixed-Use Investment
    $3,900,000
    8,325 SF
    Turnkey Woodstock Mixed-Use Investment

    5-9 Rock City Road, Woodstock, NY 12498

    High-income mixed-use building in the heart of Woodstock, NY.
    • Turnkey, high‑income mixed‑use building in the heart of Woodstock, NY.
    • Immediate cash flow from 12 units (8 residential, 4 retail) with existing leases.
    • Licensed for Short Term Rentals and zoned to operate as a boutique hotel.
    • Value‑add opportunity to convert existing leased residential units to Short Term Rentals.
    • Includes a separate cottage, currently used as retail, with the option to convert to a residential unit.
    Updated: Feb 16
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    Woodstock Cottages Investment Opportunity
    $2,295,000
    6.00 Acres
    Woodstock Cottages Investment Opportunity

    Five unique cottages on six wooded acres near Woodstock.

    2465 Glasco Turnpike, Woodstock, NY 12498

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    Woodstock Cabins with Rental Freedom
    $2,500,000
    Woodstock Cabins with Rental Freedom

    Five renovated cabins on 6 acres with proven rental income.

    2465 Glasco Turnpike, Woodstock, NY 12498

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    Based on your search, we've compiled 8 Potential Opportunities for your consideration. Besides 4 Active listings in Woodstock, NY, 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.

    Tannersville Multi-Unit Investment Opportunity
    $799,000
    2,842 SF
    Tannersville Multi-Unit Investment Opportunity

    Two residences on one property, ideal for rental income.

    98 Spruce St, Tannersville, NY 12485

    View details
    Updated Home with Flexible Living
    $399,000
    1,776 SF
    Updated Home with Flexible Living

    Updated home perfect for Airbnb, homeowner, or investor.

    95-97 Livingston Street, Saugerties, NY 12477

    View details
    Two Homes in Tannersville, NY
    $329,900
    1,754 SF
    Two Homes in Tannersville, NY

    Two homes on half acre near Hunter Mountain.

    534-538 Platte Clove Road, Tannersville, NY 12485

    View details
    Updated Home with Flexible Living
    $425,000
    1,776 SF
    Updated Home with Flexible Living

    Updated home offers flexible living as a single-family or two-unit.

    95-97 Livingston Street, Saugerties, NY 12477

    View details

    Woodstock, NY Short Term Rental Properties Market Trends and Statistics

    Explore 4 short term rental properties for sale in Woodstock, NY, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 12,656 square feet of properties for sale, with an estimated market value of $5,895,000.

    Sale prices for short term rental properties in Woodstock, NY start at $1,995,000, averaging $2,947,500, and reaching up to $3,900,000 — 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

    Duplexes 7
    Short term rental properties 4
    Apartment buildings 1

    Demographics Overview

    Population 4,530
    Population Growth (5Y) -9.5%
    Median Household Income $80,221
    College Educated 91.3%

    High-Yield Neighborhoods for Investment

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

    Neighborhood Average Price
    12498 $2.7M

    Listings Trend

    New vs delisted commercial listings in Ulster County

    New Delisted

    Total CRE Inventory on Market (SF)

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