323 Main St

Old Saybrook, CT 06475

$775,000
Last Sold Price
—
Beds
2,616 Sq. Ft.
$296 / Sq. Ft.
2,616
Sq. Ft.
$296
per Sq. Ft.
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Closed 5/4/26
Closed 5/4/26
a front view of residential houses

Description

A significant price reduction! Don't miss this great opportunity to be the next owner of this exquisite antique property in the historic district of beautiful Old Saybrook, Connecticut. Completely restored in keeping with circa 1790 yet with all the modern conveniences. This is a multi use investment property with retail space on the main level currently equipped for a restaurant or cafe. The 2nd floor use has 3 units each with a full and remodeled bath. The main floor also has living space with...A significant price reduction! Don't miss this great opportunity to be the next owner of this exquisite antique property in the historic district of beautiful Old Saybrook, Connecticut. Completely restored in keeping with circa 1790 yet with all the modern conveniences. This is a multi use investment property with retail space on the main level currently equipped for a restaurant or cafe. The 2nd floor use has 3 units each with a full and remodeled bath. The main floor also has living space with a full bath. Walk to downtown with its' awesome restaurants, cafes, wonderful boutique shops and the world renowned Katherine Hepburn Performing Art Center. A bike ride away to the public town beaches and the gorgeous Saybrook Point Resort & Marina. Enjoy all that the pretty Connecticut shoreline town has to offer to include the stunning waterfront on the Fenwick Golf Course. Old Saybrook is a quintessential New England town that is a highly regarded destination for visitors from all over the world. An easy and no fuss destination for travelers coming from NYC and Boston by train. Visitors explore the Connecticut shoreline rich in history and culture with Mystic Seaport 30 minutes away. This B&B is notably called the James Pharmacy Bed & Breakfast for the historic significance of the first female pharmacist to own and operate a pharmacy in Connecticut. Prior to it being a pharmacy, the building dates back to 1790 when it was first built and was used a general store.
  1. Listed by Meg R Goodrich • William Raveis Real Estate
    P: (860)-518-3066 C: (860)-518-3066 meg.goodrich@raveis.com

Property Details for 323 Main Street

Location
Downtown, Historic Area, Retail Corridor
Neighborhood
N/A
Garage Parking Info
Paved, Off Street Parking
LISTING UPDATED: 05/05/2026 12:41 AM

Property Details for 323 Main Street

StatusClosed
MLS #24160108
Days on Market29
Taxes$5,340 / year
HOA Fees-
Condo/Co-op Fees-
Property Type-
MLS Type-
Year Built1790
Lot Size0.25 AC / 10,890 SF
CountyMiddlesex County
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Location

Listing Courtesy of William Raveis Real Estate, Meg R Goodrich

Sold By Re/Max Valley Shore, Craig Milton

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Building Information for 323 Main Street

Stories-Residences2Year Built1790Lot Size0.25 AC / 10,890 SF

Payment Calculator

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$4,307 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,862

Property Taxes

$445

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 323 Main Street

Summary
Property and Location
  • Directions: Main Street . The cross street is Pennywise
  • Latitude: 41.286167
  • Longitude: -72.37575
  • State: Connecticut
Parking
  • Parking Total Spaces: 10
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $5,340
Interior and Exterior Features
Interior Features
  • Cooling System: Central Air, Zoned
  • Heat Type: Steam
  • Flooring: Concrete, Tile, Wood
  • Rooms Total: 0
Room 5
  • Listing Key: 4D2ACAFC47DA85E4E063E201100A642B
Property
Property and Assessments
  • Construction Description: Frame, Stone, Concrete
  • Present Use: Restaurant and bed & breakfast
  • Road Frontage Description: Municipal Street, Paved Road
  • Roof: Asphalt Shingle
  • Sq Ft Source: Owner
  • Year Built: 1790
  • Bank Owned Property: No
Lot Information
  • Documents Available: Lead Disclosure
  • Lot Description: Level Lot
  • Parcel Number: 1026687
  • Sq Ft Total: 2616.0
  • Zoning: A
Utilities
  • Heat Fuel Type: Electric, Oil
  • Sewage System: Septic
  • Sewer Assess Description: new septic system installed 2017
  • Utilities Available: Electric, Cable
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Tenant
  • Total Number of Units: 2
Building Details
  • Number of Restrooms: 5
Unit 1
  • Unit Average Sq Ft: 3
  • Unit Entry Order: 3
  • Unit Full Baths: 1
  • Unit Modified Date: 03-19-2026
  • Unit Number Of: 3
  • Unit Type: 1 Bedroom
Unit 2
  • Unit Average Sq Ft: 350
  • Unit Entry Order: 1
  • Unit Full Baths: 1
  • Unit Modified Date: 03-19-2026
  • Unit Number Of: 3
  • Unit Type: 1 Bedroom
Unit 3
  • Unit Average Sq Ft: 350
  • Unit Entry Order: 2
  • Unit Full Baths: 1
  • Unit Modified Date: 03-19-2026
  • Unit Number Of: 3
  • Unit Type: 1 Bedroom
Unit 4
  • Unit Average Sq Ft: 500
  • Unit Entry Order: 4
  • Unit Full Baths: 1
  • Unit Modified Date: 03-19-2026
  • Unit Type: Efficiency
Unit 5
  • Unit Entry Order: 5
  • Unit Half Baths: 2
  • Unit Modified Date: 03-19-2026
  • Unit Num Vacant: 1
  • Unit Type: Retail

Property History for 323 Main Street

DateEvent & SourcePriceAppreciation
Oct 20, 2016

Closed (Public Record)

Public Record #582147344

$360,000

+2.1% / yr

Aug 28, 2000

Closed (Public Record)

Public Record #92097760

$257,500

+8.2% / yr

Feb 12, 1996

Closed (Public Record)

Public Record #92089291

$180,000—
DateEvent & SourcePrice
10/20/2016

Closed (Public Record)

Public Record #582147344

$360,000

+2.1% / yr

08/28/2000

Closed (Public Record)

Public Record #92097760

$257,500

+8.2% / yr

02/12/1996

Closed (Public Record)

Public Record #92089291

$180,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 323 Main Street

Taxable ValueLand$106,900Additions$237,600Total$344,500
Tax Record2024$5,340 ($445 / month)
Home Facts
Baths5Total Finished SqFt3,029 SqFtAbove Grade Finished SqFt3,029 SqFtUnfinished Basement SqFt1,266 SqFtStories2Lot Size10,890 SqFtStyleMiscellaneous CommercialYear Built1790ZoningACountyLOWER CONNECTICUT RIVERAPNOSAY M:030 B:003 L:

Schools near 323 Main Street

This home is within Old Saybrook School District.
Rating
School
Type
Grades
Distance
Kathleen E. Goodwin School
Public - PK to 4
Old Saybrook Middle School
Public - 5 to 8
Old Saybrook Senior High School
Public - 9 to 12
St John School
Private - PK to 8
Rating
School
Distance
Kathleen E. Goodwin School
PublicPK to 4

Old Saybrook Middle School
Public5 to 8

Old Saybrook Senior High School
Public9 to 12

St John School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of William Raveis Real Estate, Meg R Goodrich

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.