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    34 properties
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    Converted Duplex on Private Acreage
    Updated: Apr 22
    Converted Duplex on Private Acreage

    32 Old Route 199, Red Hook, NY 12571

    $899,000
    3,500 sqft 4.00 AC lot
    Converted into 2 units with just one wall separating them; can be returned to a single‑family layout
    Unit 1: four bedrooms and three bathrooms, plus finished basement; currently generating steady long‑term rental income
    Unit 2: two bedrooms and two bathrooms; successful Airbnb track record
    Wood‑burning fireplace and an additional wood stove for both residences
    Set on four acres with mature trees and vibrant gardens, plus expansive decks and porches
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    This listing looks promising.

    Here's a quick look at some key insights for

    32 Old Route 199, Red Hook, NY 12571

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    • Est. Cap Rate

      7.2%
      Above avg (5.9%)

    • Est. NOI

      $65K
      Annual

    • Price @ 7% Cap

      $928K
      Above asking

    • Property Type

      Duplex
      Built 1976
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    Renovated Duplex with Private Outdoor Space
    Updated: Jun 21
    Renovated Duplex with Private Outdoor Space

    133 N Smith Road, Lagrangeville, NY 12540

    $650,000
    1.23 AC lot
    Duplex built in 1985 on 1.23 private acres, with mature trees and landscaped, level grounds
    Main residence: 3 bedrooms, 2 bathrooms, with granite/quartz counters and access to a second‑floor deck
    Second unit: 2 bedrooms, 1 bathroom, includes a sunroom with direct access to the backyard
    Renovations include updated flooring plus updated cabinetry and appliances in both units
    Additional improvements: newer roof, whole‑house generator, and water filtration system
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    Historic Corner-Lot 2-Family Home
    Historic Corner-Lot 2-Family Home

    21 Leonard Street, Beacon, NY 12508

    $819,000
    0.17 AC lot

    Legal 2-family with a walk-out basement, large attic, free-standing garage, and off-street parking on a quiet corner lot.

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    Renovated Two-Family Residential Income
    Renovated Two-Family Residential Income

    17 Carroll Street, Poughkeepsie, NY 12601

    $500,000
    0.07 AC lot

    Turnkey renovated two-family with both units leased and a shared backyard, designed for low-maintenance living.

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    Ranch-Style Duplex with Outbuildings
    Ranch-Style Duplex with Outbuildings

    32 Old Route 199, Red Hook, NY 12571

    $899,000
    4.00 AC lot

    Two residential units sit on four acres with decks and porches, plus a studio cottage and former sheep barn storage.

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    Updated Two-Family Cape Cod Home
    Updated Two-Family Cape Cod Home

    26 Old Hollow Road, Clinton Corners, NY 12514

    $449,900
    0.98 AC lot

    Completely renovated duplex with two two-bedroom units, new roof, updated kitchens and baths, plus recent furnace and septic.

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    Two-Family Property Near Colleges
    Two-Family Property Near Colleges

    2 Poplar Street, Poughkeepsie, NY 12601

    $349,000
    1,512 sqft 0.11 AC lot

    Two-family property with strong rental income near colleges and transportation.

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    Ranch Duplex for Renovation
    Ranch Duplex for Renovation

    646 Oak Summit Road, Millbrook, NY 12545

    $374,900
    1.70 AC lot

    Two separate residences in a ranch-style duplex on a corner lot with outdoor spaces, ready for updates and customization.

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    Two-Family Colonial Residence
    Two-Family Colonial Residence

    680 Vassar Road, Poughkeepsie, NY 12603

    $550,000
    0.68 AC lot

    Two-family center-hall Colonial with an updated one-bedroom rental apartment accessed by a separate entrance.

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    Spacious Two-Family Home in Hyde Park
    Spacious Two-Family Home in Hyde Park

    18 W Market Street, Hyde Park, NY 12538

    $375,000
    0.30 AC lot

    Two-family home with two kitchens, large backyard, and two-car garage.

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    Fully Occupied Income Duplex
    Fully Occupied Income Duplex

    33 Manitou Avenue, Poughkeepsie, NY 12601

    $449,999
    0.08 AC lot

    Well-maintained duplex with two units, fully occupied and producing rental income in Poughkeepsie.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    65 N Clinton Street, Poughkeepsie, NY 12601

    $379,000
    0.12 AC lot

    Fully vacant two-family with one- and two-bedroom units plus a partially completed third-floor space.

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    Two-Home Residential Income Property
    Two-Home Residential Income Property

    37 Glen Avenue, Dover Plains, NY 12522

    $375,000
    0.99 AC lot

    Two residences with separate electrical meters offer income potential and contractor-friendly renovation scope.

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    Multi-Home Property with Income Potential
    Multi-Home Property with Income Potential

    596-598 Freedom Plains Road, Poughkeepsie, NY 12603

    $499,000
    1.06 AC lot

    Two homes on one property with expansion opportunity.

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    Poughkeepsie Multifamily Investment Opportunity
    Poughkeepsie Multifamily Investment Opportunity

    161 Union Street, Poughkeepsie, NY 12601

    $399,000
    0.08 AC lot

    Two-unit property near transportation and amenities with strong rental income.

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    Duplex with Fenced Yard Parking
    Duplex with Fenced Yard Parking

    361 Church Street, Poughkeepsie, NY 12601

    $454,930
    0.14 AC lot

    Two-unit duplex with separate utilities, updated roof and electric, plus a fenced backyard and ample parking.

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    Two-Family Investment Property with Garage
    Two-Family Investment Property with Garage

    2574-2576 South Avenue, Wappingers Falls, NY 12590

    $560,000
    0.50 AC lot

    Two-family property in Wappingers Falls with a detached three-car garage.

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    Two-Family Residential Income Property
    Two-Family Residential Income Property

    63 Thompson Street, Poughkeepsie, NY 12601

    $409,000
    0.22 AC lot

    Well-maintained two-family home on 0.22 acres with off-street parking for six cars.

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    Two-Family Home with Detached Garage
    Two-Family Home with Detached Garage

    51 Lincoln Avenue, Poughkeepsie, NY 12601

    $429,900
    0.18 AC lot

    A two-unit property with separate utilities, central air on the first floor, and a detached two-car garage.

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    Poughkeepsie Multifamily Investment Opportunity
    Poughkeepsie Multifamily Investment Opportunity

    83 Albany Street, Poughkeepsie, NY 12601

    $365,000
    0.17 AC lot

    Two-unit property near train, waterfront, and Walkway over the Hudson.

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    Two-Unit Duplex with Bonus Space
    Two-Unit Duplex with Bonus Space

    7 Gray, Poughkeepsie, NY 12603

    $445,000

    Duplex with two 2-bedroom units and additional flexible bonus space, suited for owner-occupancy or rental use.

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    Two-Family Ranch Income Property
    Two-Family Ranch Income Property

    245 Hicks Hill Road, Pine Plains, NY 12581

    $164,900
    2.40 AC lot

    Two-family ranch on 2.4 acres featuring 4 bedrooms and 2.5 bathrooms, sold as-is in Pine Plains.

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    Two-Family Fixer-Upper
    Two-Family Fixer-Upper

    1 Gifford Avenue, Poughkeepsie, NY 12601

    $150,000
    0.18 AC lot

    Two-unit residential property with 2BR/2BA layouts, partially gutted and offered as-is for renovation financing or cash.

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    Two-Unit Residential Income Property
    Two-Unit Residential Income Property

    6 Zimmer Avenue, Poughkeepsie, NY 12601

    $310,000
    0.07 AC lot

    Fully occupied two-family home with separate entrances and tenant-paid separate utilities.

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    Dutchess County, NY Duplexes Market Trends and Statistics

    Explore 34 duplexes for sale in Dutchess County, NY, showcased through 34 active listings on our real estate platform. These investment opportunities span a total of 6,524 square feet of properties for sale, with an estimated market value of $1,597,000.

    Sale prices for duplexes in Dutchess County, NY start at $349,000, averaging $532,333, and reaching up to $899,000 — 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 Dutchess County Real Estate Agencies

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

    Swan Realty of The Hudson Valley
    94 Mill Road #12 Red Hook, NY 12572
    Phone: 18458498315
    swanrealtyhv.com
    MONDELLO UPSTATE PROPERTIES LLC
    37 WEST MARKET ST POB 75 Red Hook, NY
    RBR Real Estate Solutions LLC
    Fishkill, NY 12524

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