29 Old Post Road Old Saybrook, CT $ 745,000
29 Old Post Road
$ 745,000
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29 Old Post Road

Old Saybrook, CT, 06475
$ 745,000
Bedrooms3 Baths2.1 Sq 1,604

Monthly Estimate*

$ 4,587

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Single Family Home for sale in Old Saybrook, CT

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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Single Family Active

Price

$ 745,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 6,817

Style

Lot Size

0.23

Year Built

1850

Town/City

Old Saybrook

MLS | Web ID

24181692

Features
General
Zoning 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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Interior
Cooling System Central Air
Total Rooms 7
Basement Description Partial
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Exterior
Water Source Private Well
Lot Description Some Wetlands Additional Land Avail. Borders Open Space Water View
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* Excluded Features
List By
Michael Barnes

Listing Agent

Silver And Oak Realty

Broker

michaelbarnessells@gmail.com

Email

Affordability Calculator

$5,155
Per Month
89%
11%
0%
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.
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Nearby
3042242 Elementary School
900669 Middle School
Old Saybrook High School High School
Pricing History
DatePricePrice ChangeDescription
6/6/2026$745,000 Listed Price

Map


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29 Old Post Road, Old Saybrook, CT, 06475 is a Single Family Home for sale at $745,000 with 1,604 sqft and a lot size of 0.23. 29 Old Post Road has 3 bedrooms, 2.1 baths, and was built in 1850. The property's zip code is 06475 which is in Old Saybrook, CT