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

$824,600

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,265 sqft (on 0.62 acres)

442 Main St, Old Saybrook, CT 06475

Old Saybrook Center
Refinance Your Home
Currently Off Market - Sold Nov 17, 2020 for $475,000

Home Value

Trulia Estimate
$825K
Since last month
Decreased$15K (-1.8%)
Since last year
Increased$76K (+10.1%)
Since last sale
Increased$349K (+73.4%)
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 +114% in the last 10 years
MonthEstimated value
2026
August 2026$824K
August 2026$821K
July 2026$839K
June 2026$849K
May 2026$839K
April 2026$786K
March 2026$786K
February 2026$738K
January 2026$731K
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
355 Main Street, Old Saybrook, CT
0.13
Single-Family Home
$707,500
12/19/25
3
1.5
2,194
17 Willard Street, Old Saybrook, CT
0.18
Single-Family Home
$656,000
06/22/26
3
3
1,683
1 Lighthouse Lane, Old Saybrook, CT
0.48
Single-Family Home
$860,000
01/15/26
3
2.5
3,286
3 Glen Drive, Old Saybrook, CT
0.39
Single-Family Home
$625,000
09/19/25
3
1.5
1,915
71 Maple Avenue, Old Saybrook, CT
0.38
Single-Family Home
$750,000
06/15/26
2
2
2,069
5 Cove Landing, Old Saybrook, CT
0.37
Single-Family Home
$1,648,000
09/04/26
3
2.5
2,787
19 Lynde Street, Old Saybrook, CT
0.54
Single-Family Home
$935,000
12/16/25
3
2.5
2,396
45 Farview Avenue, Old Saybrook, CT
0.60
Single-Family Home
$925,000
09/22/25
3
2.5
2,791
10 Cricket Court, Old Saybrook, CT
0.49
Single-Family Home
$941,500
01/22/26
3
1.5
1,740
24 Cottage Place, Old Saybrook, CT
0.64
Single-Family Home
$935,000
06/15/26
4
3
2,516

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
7 North Street, Old Saybrook, CT 06475
0.11
$508,000
3
1
864
Off Market
5 East Street, Old Saybrook, CT 06475
0.12
$420,400
2
1
625
Off Market
12 Maple Avenue, Old Saybrook, CT 06475
0.12
$474,300
2
1
772
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
6 West Street, Old Saybrook, CT 06475
0.13
$441,900
2
1
826
Off Market
8 East Street, Old Saybrook, CT 06475
0.13
$740,900
4
2.5
2,170
Off Market
367 Main Street #15, Old Saybrook, CT 06475
0.09
$800,600
3
2
1,558
Off Market
367 Main Street #12, Old Saybrook, CT 06475
0.10
$706,100
2
2
1,234
Off Market
367 Main Street #34, Old Saybrook, CT 06475
0.10
$863,500
3
2
1,477
Off Market
367 Main Street #38, Old Saybrook, CT 06475
0.10
$880,100
3
2
1,477
Off Market

Local Information

  • Map ViewExplore the area around 442 Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1955
0.62 acre lot
2,265 sqft
$364/sqft
Garage

About this House

Walk to everything Old Saybrook has to offer from this updated lovely large 2300 sq ft ranch!!! You will enjoy the spacious rooms, central air, 3 bedrooms, 3 full bathrooms, 2 car garage, gas fireplace in Combination living room / dining room. New roof, 3 years old. A wonderful breezy 3 season room overlooks the beautiful back yard with specimen plantings which include holly and a Copper Beech tree. The location doesn't get any better, walk to shops and restaurants one way, Saybrook Point the other. Minutes to beach and Fenwick Golf. Low taxes of $5060. Low transferable FEMA flood insurance. In law possibility if needed with separate entrance. Professional photos to come. Field card shows 2 bedrooms, but home has 3 large bedrooms.
442 Main St, Old Saybrook, CT 06475 is a 3 bedroom, 3 bathroom, 2,265 sqft single-family home in Old Saybrook Center, built in 1955. It last sold for $475,000 on Nov 17, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $824,600, with a rent estimate of $4,418/month.

Home Details for 442 Main St

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Shingle Not WoodPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.62 acres

Price and Tax history

DateEventPrice
Nov 17, 2020
Source: Smart MLS #170332683
Sold
$475,000
Sep 6, 2020
Source: Agent Provided
Pending
$497,000
Sep 2, 2020
Source: Agent Provided
Listed For Sale
$497,000
May 26, 2005
Source: Smart MLS #M9087519
Sold
$425,000
Jul 11, 2003
Source: Smart MLS #M9073537
Sold
$397,500

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

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

LGBTQ Local Legal Protections

Frequently asked questions about 442 Main St

  • What is 442 Main St estimated to be worth?
    Trulia's estimated value for 442 Main St in Old Saybrook, CT is $824,600.
  • What is the price history for 442 Main St?
    442 Main St in Old Saybrook, CT last sold for $475,000 in November 2020.
  • 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 the Old Saybrook Center neighborhood?
    Residents describe the Old Saybrook Center neighborhood in Old Saybrook, CT as easy to park in, well-kept, and walkable to restaurants. See recently sold homes in Old Saybrook Center, Old Saybrook.
  • Does 442 Main St have air conditioning?
    Yes, 442 Main St in Old Saybrook, CT has air conditioning.
  • Does 442 Main St have laundry facilities?
    Yes, 442 Main St in Old Saybrook, CT has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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

Explore by feature - Outdoor Space

Apartments for Rent

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Off Market Homes Near 442 Main St

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