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

$749,900

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

355 Main Street, Old Saybrook, CT 06475

Est. Refi. Payment $5,125/mo*
Refinance Your Home
Currently Off Market - Sold Dec 19, 2025 for $707,500 (0% below list price)

Home Value

Trulia Estimate
$750K
Since last month
Decreased$12K (-1.5%)
Since last year
Increased$22K (+3%)
Since last sale
Increased$44K (+6.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +47% in the last 10 years
MonthEstimated value
2026
August 2026$751K
August 2026$750K
July 2026$763K
June 2026$740K
May 2026$731K
April 2026$733K
March 2026$731K
February 2026$727K
January 2026$721K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
71 Maple Avenue, Old Saybrook, CT
0.37
Single-Family Home
$750,000
06/15/26
2
2
2,069
17 Willard Street, Old Saybrook, CT
0.15
Single-Family Home
$656,000
06/22/26
3
3
1,683
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
20 Hill Street, Old Saybrook, CT
0.30
Single-Family Home
$700,000
01/07/26
2
2
1,432

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
341 Main Street, Old Saybrook, CT 06475
0.06
$1,378,500
5
4
3,897
Off Market
11 Shepard Street, Old Saybrook, CT 06475
0.09
$859,500
3
2
2,400
Off Market
367 Main Street #15, Old Saybrook, CT 06475
0.05
$800,600
3
2
1,558
Off Market
367 Main Street #B32, Old Saybrook, CT 06475
0.07
$485,200
2
2
1,237
Off Market
367 Main Street #E-6, Old Saybrook, CT 06475
0.07
$542,400
2
2.5
1,358
Off Market
367 Main Street, Old Saybrook, CT 06475
0.07
$555,000
2
2
1,042
Off Market
367 Main Street #12, Old Saybrook, CT 06475
0.07
$706,100
2
2
1,234
Off Market
367 Main Street #34, Old Saybrook, CT 06475
0.07
$863,500
3
2
1,477
Off Market
367 Main Street #38, Old Saybrook, CT 06475
0.07
$880,100
3
2
1,477
Off Market
367 Main Street #47, Old Saybrook, CT 06475
0.07
$727,700
3
2
1,477
Off Market
367 Main Street #30, Old Saybrook, CT 06475
0.07
$629,900
2
2
1,042
Off Market

Local Information

  • Map ViewExplore the area around 355 Main Street.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1919
Lot Size
0.51 acres
Living Area
2,194 sqft
Price/Sqft
$322/sqft
Parking
Open Parking

About this House

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.
355 Main Street, Old Saybrook, CT 06475 is a 3 bedroom, 2 bathroom, 2,194 sqft single-family home built in 1919. It last sold for the $709,900 asking price on Dec 19, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $749,900, with a rent estimate of $3,628/month.
Last check for updates: about 10 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

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

Price and Tax history

DateEventPrice
Dec 21, 2025
Source: Berkshire Hathaway HomeServices New England Properties #24100965
ListingRemoved
$709,900
Dec 21, 2025
Source: Smart MLS #24100965
Pending
$709,900
Dec 19, 2025
Source: Smart MLS #24100965
Sold
$707,500
Nov 17, 2025
Source: Berkshire Hathaway HomeServices New England Properties #24100965
Contingent
$709,900
Nov 7, 2025
Source: Smart MLS #24100965
PriceChange
$709,900
Price decreased by 3%

Market trends in Old Saybrook

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
55
4MoM

Around this home

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

  • 43 % 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

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Frequently asked questions about 355 Main Street

  • What is 355 Main Street estimated to be worth?
    Trulia's estimated value for 355 Main Street in Old Saybrook, CT is $749,900.
  • What is the price history for 355 Main Street?
    355 Main Street in Old Saybrook, CT last sold for $707,500 in December 2025.
  • Is Old Saybrook a buyer's or seller's market?
    Old Saybrook is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Old Saybrook?
    Residents describe Old Saybrook, CT as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Old Saybrook, CT.
  • Does 355 Main Street have air conditioning?
    Yes, 355 Main Street in Old Saybrook, CT has air conditioning.
  • Does 355 Main Street have laundry facilities?
    Yes, 355 Main Street in Old Saybrook, CT has in-unit laundry.

Explore by feature - Pet Friendly

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