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For sale
  • $745,000

    29 Old Post Road, Old Saybrook, CT 06475

    3beds
    1,604sqft
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    Single Family Residence
    Built in 1850
    10,018 Square Feet Lot
    $-- Zestimate®
    $464/sqft
    $-- HOA

    What's special

    Massive private dockPrivate waterfront enclave
    Welcome to Crow's Nest, where classic New England country living meets direct waterfront luxury on the scenic Oyster River. Steeped in history, this enchanting historic farmhouse Circa 1850, is perfectly positioned along the west banks of the Oyster River, offering breathtaking water views from almost every single room. The character-rich interior features 3 bedrooms & 2.5 baths, offering cozy, sun-drenched spaces primed for your personal touch. For those with a vision, these charming spaces are ready to expand, with incredible potential to further enhance the elevated river vistas with slight modifications. A Rare, Multi-Parcel Investment Opportunity Uniquely spanning two separate parcels, this property offers unmatched flexibility and value. The home sits on one parcel, while the spectacular waterfront assets sit on a separate deeded parcel, meaning the dock parcel possesses the rare capability of being sold separately in the future if desired. The Crown Jewel: A fully permitted 325-foot private dock-standing proud as one of the absolute largest private docks in all of Old Saybrook. Bring your boats, jet skis, and kayaks! The Boathouse: An oversized 2-car detached garage offers the ultimate storage solution for all your water toys and gear. Enjoy close proximity to downtown Old Saybrook, yet remain tucked away in your own private waterfront enclave. Sit on your massive private dock, watch the wildlife pass you by & experience the pure freedom of waterfront. Important Property & Investment Note: The Two-Parcel Advantage This unique offering consists of two separate, deeded parcels being sold together, providing an unmatched real estate investment structure and exit strategy in Old Saybrook. Asset Separation: Legally, the property is comprised of two distinct lots on town land records. Parcel A features the historic 1850 farmhouse, while Parcel B holds the direct waterfront and the fully permitted, record-setting 325-ft private dock. Independent Resale Capability: Because these are two distinct parcels, the value of the dock is not permanently tied to the house. The next owner retains the legal right to split the deeds and sell the waterfront dock parcel entirely separate from the residential home parcel in the future. Unmatched Investment Value: Fully permitted, large-scale docks are nearly impossible to replicate today. This dual-parcel setup offers a rare opportunity for savvy buyers to hold a highly coveted coastal asset, maximize their portfolio, or execute a lucrative future subdivision strategy. Strategic Opportunity: Perfect for buyers who want to keep the premium waterfront property and dock for themselves to compliment another non-waterfront home in the area, while retaining the freedom to sell off the residential parcel.
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    Zillow last checked:

    Listing updated:

    Listed by:

    Michael P. Barnes (860)304-0125,

    Silver and Oak Realty 860-372-4666

    Source: Smart MLS,MLS#: 24181692MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Dining room
      • Level: Main
      Living room
      • Level: Main
      Heating
      • Forced Air, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Oven/Range, Refrigerator, Freezer, Water Heater
      • Laundry: Main Level
      Features
      • Basement: Partial
      • Attic: None
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 1,604
      • Total interior livable area: 1,604 sqft
      • Finished area above ground: 1,604

      Property

      Parking
      • Total spaces: 8
      • Parking features: Detached, Driveway, Off Street, Private, Gravel
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: Raised Toilet
      Features
      • Patio & porch: Deck
      • Exterior features: Rain Gutters
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Waterfront features: Waterfront, Walk to Water, Dock or Mooring, Access
      Lot
      • Size: 10,018 Square Feet
      • Features: Wetlands, Additional Land Avail., Borders Open Space, In Flood Zone
      Details
      • Parcel number: 1026422
      • Zoning: A

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Stone
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1850

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Near Public Transport, Golf, Park, Tennis Court(s)
      • Subdivision: Oyster River
      HOA
      • Has HOA: No
      Location
      • Region: Old Saybrook

      Financial & listing details

      • Price per square foot: $464/sqft
      • Tax assessed value: $439,800
      • Annual tax amount: $6,817
      • Date on market: 6/6/2026
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/6/2026Listed for sale$745,000+181.1%$464/sqft
        Source: Smart MLS #24181692 Report a problem
        11/15/2000Sold$265,000$165/sqft
        Source: Smart MLS #E108482 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$6,817 +2%$439,800
        2024$6,685 +24%$439,800 +66.9%
        2023$5,389 +1.9%$263,500
        2022$5,291 +0.2%$263,500
        2021$5,283 $263,500
        2020$5,283 +1.5%$263,500
        2019$5,204 -1.8%$263,500 -2.5%
        2018$5,298 -0.3%$270,300
        2017$5,314 +2.1%$270,300
        2016$5,206 +2.4%$270,300
        2015$5,084 +1.7%$270,300
        2014$5,001 -7.8%$270,300 -24.2%
        2013$5,423 +4%$356,800
        2012$5,216 +4%$356,800
        2011$5,017 +4.6%$356,800
        2009$4,795 +18.8%$356,800 +40%
        2007$4,036 $254,800

        Find assessor info on the county website

        Monthly payment

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          Payment breakdown

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          All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
          HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
          Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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          Climate risks

          Neighborhood: Saybrook Manor

          Getting around

          48 / 100
          Car-Dependent
          42 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • High: Old Saybrook

          Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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