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

$796,000

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 2,710 sqft (on 0.35 acres)

381 Main St, Old Saybrook, CT 06475

Est. Refi. Payment $5,444/mo*
Refinance Your Home
Currently Off Market - Sold Oct 31, 2014 for $345,000

Home Value

Trulia Estimate
$796K
Since last month
Decreased$4K (-0.5%)
Since last year
Increased$69K (+9.5%)
Since last sale
Increased$449K (+130.2%)
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 +94% in the last 10 years
MonthEstimated value
2026
August 2026$794K
August 2026$793K
July 2026$798K
June 2026$809K
May 2026$808K
April 2026$750K
March 2026$766K
February 2026$731K
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
46 Maple Avenue, Old Saybrook, CT
0.23
Multi-Family Home
$530,000
12/05/25
4
2
3,190
94 Waldron Drive, Westbrook, CT
2.61
Multi-Family Home
$900,000
09/30/25
6
5.5
4,940
143 Sandy Point Rd, Old Saybrook, CT
2.23
Multi-Family Home
$550,000
11/21/25
2
2.5
1,600
1286 Boston Post Road, Westbrook, CT
3.75
Multi-Family Home
$600,000
11/14/25
7
4
2,646
9 Essex Road, Westbrook, CT
3.93
Multi-Family Home
$385,000
09/05/25
3
2.5
2,376
33 Salt Island Rd, Westbrook, CT
3.76
Multi-Family Home
$400,000
09/29/25
3
2
1,246
41 South Main Street, Westbrook, CT
4.04
Multi-Family Home
$490,000
10/10/25
5
2.5
2,379
1110 Old Clinton Road, Westbrook, CT
4.42
Multi-Family Home
$672,000
01/26/26
4
3
2,428
912 Boston Post Road, Westbrook, CT
4.36
Multi-Family Home
$493,000
12/31/25
3
2
1,977
11 North Main Street, Essex, CT
4.96
Multi-Family Home
$1,150,000
07/16/26
4
4
3,036

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
367 Main Street #B32, Old Saybrook, CT 06475
0.03
$485,200
2
2
1,237
Off Market
367 Main Street #E-6, Old Saybrook, CT 06475
0.03
$542,400
2
2.5
1,358
Off Market
367 Main Street, Old Saybrook, CT 06475
0.03
$555,000
2
2
1,042
Off Market
367 Main Street #15, Old Saybrook, CT 06475
0.05
$800,600
3
2
1,558
Off Market
367 Main Street #12, Old Saybrook, CT 06475
0.03
$706,100
2
2
1,234
Off Market
367 Main Street #34, Old Saybrook, CT 06475
0.03
$863,500
3
2
1,477
Off Market
367 Main Street #38, Old Saybrook, CT 06475
0.03
$880,100
3
2
1,477
Off Market
367 Main Street #47, Old Saybrook, CT 06475
0.03
$727,700
3
2
1,477
Off Market
367 Main Street #30, Old Saybrook, CT 06475
0.03
$629,900
2
2
1,042
Off Market
367 Main Street #4, Old Saybrook, CT 06475
0.03
$601,400
2
2
1,042
Off Market
12 Maple Avenue, Old Saybrook, CT 06475
0.09
$474,300
2
1
772
Off Market
7 North Street, Old Saybrook, CT 06475
0.11
$508,000
3
1
864
Off Market

Local Information

  • Map ViewExplore the area around 381 Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1860
0.35 acre lot
2,710 sqft
$294/sqft

About this House

Hard to find 3 family home on Main Street. Great investment opportunity. Wonderful location?close to town center shops, restaurants, library etc. 1st flr, 2BR owner's unit is vacant, 2 - 2nd flr, 1 BR units rented. Nice yard, lots of parking. OSWWM area
381 Main St, Old Saybrook, CT 06475 is a 4 bedroom, 5 bathroom, 2,710 sqft multi-family built in 1860. It last sold for $345,000 on Oct 31, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $796,000, with a rent estimate of $2,544/month.

Home Details for 381 Main St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 12Ceiling Fan
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable Ready

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodLawnPatioPorch
Parking & Garage
Parking: Off Street, On Street

Property Information

Year Built
Year Built: 1860
Property Type / Style
Property Type: Multi FamilyArchitecture: Queen Anne / Victorian

Community

Units in Building: 3

Lot Information

Lot Area: 0.35 acres

Price and Tax history

DateEventPrice
Oct 31, 2014
Source: Smart MLS #M9149313
Sold
$345,000
Jul 22, 2014
Source: Agent Provided
Listed For Sale
$374,900
Aug 2, 1988
Source: N/A
Sold
$264,000

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

Frequently asked questions about 381 Main St

  • What is 381 Main St estimated to be worth?
    Trulia's estimated value for 381 Main St in Old Saybrook, CT is $796,000.
  • What is the price history for 381 Main St?
    381 Main St in Old Saybrook, CT last sold for $345,000 in October 2014.
  • 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 381 Main St have parking?
    Yes, 381 Main St in Old Saybrook, CT has on-site parking.

Explore by feature - Pet Friendly

9 pet-friendly rentals in Old Saybrook, CT

Explore by feature - Garage

11 rentals with a garage in Old Saybrook, CT

Explore by feature - Air Conditioning

17 rentals with air conditioning in Old Saybrook, CT

Explore by feature - Washer/dryer

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

Explore by feature - Outdoor Space

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 381 Main St

Skip to last item
Skip to first item

Homes for sale near 381 Main St

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item