29 Old Post Road
Old Saybrook, CT, 06475 $ 745,000
Bedrooms3 Baths2.1 Sq 1,604 Monthly Estimate*
$ 4,587
for $745,000 with 3 bedrooms and 2 full baths, 1 half bath. This 1,604 square foot home was built in 1850 on a lot size of 0.23.
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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FeaturesGeneralZoning A
Neighborhood Oyster River
County Middlesex
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 0.23
Directions RTE 1 to Old Post Road to Number 29 on Right
High School Old Saybrook
City Old Saybrook
Elementary School Per Board of Ed
Sq Ft Total 1604
DOM 1
Year Built 1850
Style Cape Cod
Year Built Source Public Records
Handicap Features Raised Toilet
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InteriorCooling System Central Air
Total Rooms 7
Basement Description Partial
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ExteriorWater Source Private Well
Lot Description Some Wetlands Additional Land Avail. Borders Open Space Water View
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* Excluded FeaturesList ByMichael BarnesListing Agent
Silver And Oak RealtyBroker
michaelbarnessells@gmail.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $4,587
- Monthly Property Taxes
- $568
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Old Saybrook, CT
Average List Price $1,489,585
Percent of Sale Price 100%
About Old Saybrook, CT 10,363 Population
0% Since 2002
$ 77,346 Median Income
53.19 Median Age
22% Households with Children
Trends Information provided by ATTOM Data Solutions.
3042242 Elementary School
900669 Middle School
Old Saybrook High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 6/6/2026 | $745,000 | | Listed Price |