404 Main St, Old Saybrook, CT 06475
Property image
Property image
OFF MARKET

404 Main St
Old Saybrook, CT 06475

Old Saybrook Center
  • 3 Beds
  • 2 Baths
  • 1,898 sqft (on 0.76 acres)

$733,900

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $4,913/mo*
Refinance Your Home

$733,900

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $4,913/mo*
Refinance Your Home
3 Beds
2 Baths
1,898 sqft
(on 0.76 acres)

Local Information

  • Map ViewExplore the area around 404 Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Walk to town or Saybrook Point from this Circa 1697 barrel vault center chimney Cape. The historic John Shipman house enjoys 4 fireplaces with a beehive oven in kitchen. Borders North Cove with distant marsh views. New roof and freshly painted.
404 Main St, Old Saybrook, CT 06475 is a 3 bedroom, 2 bathroom, 1,898 sqft single-family home in Old Saybrook Center, built in 1697. It last sold for $296,500 on Aug 4, 2010. It is currently off market. The Trulia Estimate is $733,900, with a rent estimate of $3,399/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 404 Main St

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1697
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.76 acres

Price History for 404 Main St

DatePriceEventSource
08/04/2010$296,500Sold
Smart MLS #M9119056
06/02/2010$324,900PriceChange
Agent Provided
03/31/2010$349,900PriceChange
Agent Provided
01/18/2010$374,900PriceChange
Agent Provided
12/26/2009$399,500PriceChange
Agent Provided
12/15/2009$415,000PriceChange
Agent Provided
10/28/2009$399,500PriceChange
Agent Provided
10/10/2009$415,000PriceChange
Agent Provided
06/07/2009$465,000PriceChange
Agent Provided
04/11/2009$499,000PriceChange
Agent Provided
03/24/2009$549,000Listed For SaleAgent Provided

Market trends in Old Saybrook

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
45
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Property Tax and Assessment

Year2025
Tax$6,532
Assessment$421,400
Home facts updated by county records

Comparable Sales for 404 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
355 Main Street, Old Saybrook, CT
0.07
Single-Family Home
$707,500
12/19/25
3
1.5
2,194
3 Glen Drive, Old Saybrook, CT
0.29
Single-Family Home
$625,000
09/19/25
3
1.5
1,915
17 Willard Street, Old Saybrook, CT
0.20
Single-Family Home
$656,000
06/22/26
3
3
1,683
71 Maple Avenue, Old Saybrook, CT
0.42
Single-Family Home
$750,000
06/15/26
2
2
2,069
10 Cricket Court, Old Saybrook, CT
0.50
Single-Family Home
$941,500
01/22/26
3
1.5
1,740
14 Ruth Dr, Old Saybrook, CT
0.57
Single-Family Home
$600,000
07/23/25
3
2
1,496
18 Quarry Street, Old Saybrook, CT
0.59
Single-Family Home
$510,000
05/07/26
4
2
1,760
99 Maple Avenue, Old Saybrook, CT
0.55
Single-Family Home
$675,000
02/20/26
3
1.5
1,170
16 Howard Street, Old Saybrook, CT
0.32
Single-Family Home
$742,900
10/31/25
3
2
1,404
103 Maple Avenue, Old Saybrook, CT
0.57
Single-Family Home
$645,000
04/21/26
2
2
1,744

Nearby homes

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Assigned Schools

These are the assigned schools for 404 Main St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Old Saybrook Center
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Old Saybrook Center

At least 10 Trulia users voted on each feature.

  • 100 % Say there's holiday spirit

  • 91 % Say streets are well-lit

  • 87 % Say parking is easy

  • 86 % Say yards are well-kept

  • 85 % Say it's walkable to restaurants

  • 82 % Say they plan to stay for at least 5 years

  • 81 % Say there are sidewalks

  • 80 % Say it's dog friendly

  • 79 % Say car is needed

  • 76 % Say people would walk alone at night

  • 67 % Say kids play outside

  • 63 % Say neighbors are friendly

  • 58 % Say there's wildlife

  • 54 % Say it's walkable to grocery stores

  • 54 % Say there are community events

  • 47 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.
  • Diva For Life
    "I think is great to live here I think it safe for family and I hope I can move here with my family soon "
    0
    Flag
  • Trulia User
    "It’s a safe town, good schools. A lot of different activities and programs available for kids from toddlers to high school. The schools are located in convenient safe areas of the town. Lower traffic areas. Pedestrians are plentiful and kids riding bikes to and from school. Several beaches that are great for family gatherings as well as private time to yourself. Everything you need to bring your family up in a quiet shoreline community. Public transportation is available with a trolly during the months of spring and summer. The library is conveniently located next to the elementary school. Plenty of in town shopping available and plenty of great restaurants. Ice cream as well. "
    1
    Flag
  • Tony
    "I've lived in the area for over 12 years. Everything (shopping, dining, etc.) are all within walking distance, with plenty of sidewalks. most neighbors are friendly, and willing to lend a hand when needed."
    5
    Flag
  • Ali F.
    "No sidewalks. Some neighbors let dogs walk off the leash. There are Coyotes or coy dogs that are found to live around the marsh areas. I have had squirrels in my attic three times even after sealing. "
    6
    Flag
  • Ali F.
    "Love our neighborhood. Close walking to center of town. Neighbors are friendly. Birds, rabbits and squirrels. Sometimes can see coyote or deer. "
    0
    Flag
  • Karen E. d.
    "Train station is within walking distance with newly installed sidewalks and street lighting. I95 is easily accessible for commutes to New York or north. Personally, I am able to walk to my job in the downtown area. "
    0
    Flag
  • Karen E. d.
    "Lots of friendly dogs in area. Most on leashes or in fenced yards. Some of the Main St. businesses put water out for our four legged friends. "
    1
    Flag
  • Bean_laura
    "Lots of other dogs. Dog parks. Pet stores. Fire hydrants. Pet friendly restaurants and bars. Pet friendly shopping."
    1
    Flag

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Apartments for Rent

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Explore by feature - Garage

11 rentals with a garage in Old Saybrook, CT

Explore by feature - Air Conditioning

16 rentals with air conditioning in Old Saybrook, CT

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19 rentals with a washer/dryer in Old Saybrook, CT

Homes for sale near 404 Main St

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Off Market Homes Near 404 Main St

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