355 Main Street, Old Saybrook, CT 06475
SOLD
DEC 19, 2025

355 Main Street
Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 2,194 sqft (on 0.51 acres)

$707,500

Last Sold: Dec 19, 2025
0% below list $710K
$322/sqft
Est. Refi. Payment $3,661/mo*
Refinance Your Home

$707,500

Last Sold: Dec 19, 2025
0% below list $710K
$322/sqft
Est. Refi. Payment $3,661/mo*
Refinance Your Home
3 Beds
1.5 Baths
2,194 sqft
(on 0.51 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

In the heart of Old Saybrook! This home was built in 1919 and is called a New Englander. This Main Street house offers a walkable location to Main Street which has all the local flair! Stroll to the Katherine Hepburn theater which offers many events thru out the year. Main Street has shopping and restaurants or just a beautiful walk. Walking distance to Kathleen Goodwin school, Main Street school the library and Farmers Market in warmer weather. This is walkable to the Amtrack Train Station and local pickelball courts. With charm and a beautiful level yard. A two car detached garage and .51 acre. Updates and new carpet installed on front porch.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from December 21, 2025

Home Highlights

Parking
Open Parking
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$322/sqft
Listed
180+ days ago

Home Details for 355 Main Street

Interior Features

Interior Details
Basement: FullNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Kitchen, Living Room, Office, Study, Sun Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2194 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: None,Driveway,Private
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2194 Square Feet

Property Information

Year Built
Year Built: 1919
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Other
Building
Construction Materials: Shingle SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1025883

Price & Status

Price
List Price: $709,900Price Per Sqft: $322/sqft
Status Change & Dates
Off Market Date: Sat Nov 15 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Old Saybrook
School Information
Elementary School: Kathleen E. GoodwinJr High / Middle School: Per Board of EdHigh School: Old Saybrook

Building

Building Area
Building Area: 2194 Square Feet

Community

Community Features: Golf, Health Club, Library, Medical Facilities, Playground, Private School(s), Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.51 acres

Miscellaneous

BasementMls Number: 24100965Attic: Walk-upAttribution Contact: (860) 575-5559Above Grade Unfinished Area: 2194Activation Date: Sat Jun 14 2025

Additional Information

GolfHealth ClubLibraryMedical FacilitiesPlaygroundPrivate School(s)Shopping/Mall
Last check for updates: about 6 hours ago
Listed by Paula Stuart, (860) 575-5559
Berkshire Hathaway NE Prop., (860) 388-3411
Bought with: Kristen Leo, (860) 227-8685, William Raveis Real Estate, (860) 536-2600
Source: Smart MLS, MLS#24100965

Price History for 355 Main Street

DatePriceEventSource
12/21/2025$709,900ListingRemovedBerkshire Hathaway HomeServices New England Properties #24100965
12/21/2025$709,900PendingSmart MLS #24100965
12/19/2025$707,500Sold
Smart MLS #24100965
11/17/2025$709,900ContingentBerkshire Hathaway HomeServices New England Properties #24100965
11/07/2025$709,900PriceChange
Smart MLS #24100965
09/13/2025$729,000Listed For SaleSmart MLS #24100965
08/08/2025$749,000ListingRemovedSmart MLS #24100965
07/24/2025$749,000ContingentBerkshire Hathaway HomeServices New England Properties #24100965
07/01/2025$749,000PendingToActiveBerkshire Hathaway HomeServices New England Properties #24100965
06/30/2025$749,000ContingentBerkshire Hathaway HomeServices New England Properties #24100965
06/14/2025$749,000Listed For SaleSmart MLS #24100965
09/17/2015$515,000Sold
Smart MLS #N10068835
06/30/2015$549,000PendingToActiveAgent Provided
06/27/2015$549,000PendingAgent Provided
01/15/2015$549,000PriceChange
Agent Provided
08/11/2014$579,000Listed For SaleAgent Provided
09/28/2012$370,000Sold
Smart MLS #M9135066
07/24/2012$399,900PriceChange
Agent Provided
07/10/2012$450,000PriceChange
Agent Provided
06/09/2012$499,900Listed For SaleAgent Provided
11/23/2011$435,000Sold
N/A
05/21/2011$450,000Listed For SaleAgent Provided
11/19/2010$489,900ListingRemovedAgent Provided
08/22/2010$489,900Listed For SaleAgent Provided
08/19/1999$237,000Sold
N/A

Market trends in Old Saybrook

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
45
10MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$7,060
Assessment$455,500
Home facts updated by county records

Comparable Sales for 355 Main Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Glen Drive, Old Saybrook, CT
0.27
Single-Family Home
$625,000
09/19/25
3
1.5
1,915
10 Cricket Court, Old Saybrook, CT
0.44
Single-Family Home
$941,500
01/22/26
3
1.5
1,740
99 Maple Avenue, Old Saybrook, CT
0.50
Single-Family Home
$675,000
02/20/26
3
1.5
1,170
19 Lynde Street, Old Saybrook, CT
0.44
Single-Family Home
$935,000
12/16/25
3
2.5
2,396
16 Howard Street, Old Saybrook, CT
0.27
Single-Family Home
$742,900
10/31/25
3
2
1,404
103 Maple Avenue, Old Saybrook, CT
0.51
Single-Family Home
$645,000
04/21/26
2
2
1,744
24 Lynde Street, Old Saybrook, CT
0.45
Single-Family Home
$799,900
07/31/25
4
2.5
2,756

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 355 Main Street.
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.

What Locals Say about Old Saybrook

At least 42 Trulia users voted on each feature.

  • 88 % Say yards are well-kept

  • 88 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 84 % Say parking is easy

  • 78 % Say car is needed

  • 75 % Say people would walk alone at night

  • 66 % Say they plan to stay for at least 5 years

  • 61 % Say neighbors are friendly

  • 61 % Say kids play outside

  • 60 % Say there's wildlife

  • 58 % Say it's quiet

  • 57 % Say streets are well-lit

  • 56 % Say it's walkable to restaurants

  • 52 % Say there are sidewalks

  • 51 % Say there are community events

  • 44 % Say it's walkable to grocery stores

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
  • Jocelynne B. .
    "It’s a safe place to live and the school system is very good. Small class rooms and everyone knows everyone. "
    0
    Flag
  • Tyfinkbus
    "I have lived in Old Saybrook for 15 years and the people are very friendly. The area is peaceful and very well maintained."
    0
    Flag
  • John D.
    "I commute by my car, motorcycle, scooter, or bicycle. I do not use public transportation. I also walk to the beach or downtown. "
    1
    Flag
  • J Jenkins
    "I lived in this neighborhood for 40 yrs, I love it here, we have had our children here and now have there own homes close by. We are only 1.1 miles from I-95, 1.5 to the supermarket, 2 miles to main St and 3 miles to the beach. A great area."
    0
    Flag
  • Svasmatics
    "I moved to Old Saybrook because I work in town. It is close to I-95 and Route9. The town itself and traffic is very different from winter to summer. Summer brings a lot of snow birds and visitors. Stores, traffic, commotion in general is heavier in the summer months. Food prices also go up in the summer."
    2
    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
  • Annette M.
    "Wonderful beach community for families and singles. I rent here but most people own and the community is very tight knit and supportive."
    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
  • Jocelynne B.
    "It’s a quiet neighborhood with no issues. Saybrook is safe and the school system is excellent. I enjoyed growing up and living in Saybrook. It’s a very friendly community."
    0
    Flag
  • Kearney j.
    "I've lived here for 25 years. it is a safe and welcoming community. pride I. home and property is prevalent everywhere. neighbors are friendly and supportive."
    0
    Flag
  • Rose H. M.
    "Fenwood beach is one of the most desirable areas along the shore, with a private beach, bordering Fenwick golf course, with views of the Saybrook lighthouses from the shore. The residents have lots of social activities, such as the summer lobster bake on the beach. Residents often ride golf carts around the neighborhood and to the beach. Fenwood beach is also a short drive into the quaint town center and to Saybrook Point. "
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature

Homes for sale near 355 Main Street

Skip to last item
Skip to first item

Off Market Homes Near 355 Main Street

Skip to last item
Skip to first item
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Homes for rent near 355 Main Street

Skip to last item
  • Results are loading
Skip to first item
355 Main Street, Old Saybrook, CT 06475 is a 3 bedroom, 2 bathroom, 2,194 sqft single-family home built in 1919. This property is not currently available for sale. 355 Main Street was last sold on Dec 19, 2025 for $707,500 (0% lower than the asking price of $709,900). The current Trulia Estimate for 355 Main Street is $729,600.