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

$987,500

Trulia Estimate
  • 5 Beds
  • 1.5 Baths
  • 2,381 sqft (on 0.60 acres)

385 Main St, Old Saybrook, CT 06475

Est. Refi. Payment $6,863/mo*
Refinance Your Home
Currently Off Market - Sold Sep 11, 2017 for $341,900

Home Value

Trulia Estimate
$988K
Since last month
Decreased$2K (-0.2%)
Since last year
Increased$139K (+16.4%)
Since last sale
Increased$644K (+188.4%)
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 +102% in the last 10 years
MonthEstimated value
2026
August 2026$986K
August 2026$984K
July 2026$988K
June 2026$1.01M
May 2026$1.02M
April 2026$922K
March 2026$916K
February 2026$858K
January 2026$857K
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
0.10
Single-Family Home
$707,500
12/19/25
3
1.5
2,194
17 Willard Street, Old Saybrook, CT
0.11
Single-Family Home
$656,000
06/22/26
3
3
1,683
71 Maple Avenue, Old Saybrook, CT
0.32
Single-Family Home
$750,000
06/15/26
2
2
2,069
3 Glen Drive, Old Saybrook, CT
0.37
Single-Family Home
$625,000
09/19/25
3
1.5
1,915
10 Cricket Court, Old Saybrook, CT
0.42
Single-Family Home
$941,500
01/22/26
3
1.5
1,740
18 Quarry Street, Old Saybrook, CT
0.67
Single-Family Home
$510,000
05/07/26
4
2
1,760
99 Maple Avenue, Old Saybrook, CT
0.45
Single-Family Home
$675,000
02/20/26
3
1.5
1,170
103 Maple Avenue, Old Saybrook, CT
0.47
Single-Family Home
$645,000
04/21/26
2
2
1,744
20 Hill Street, Old Saybrook, CT
0.20
Single-Family Home
$700,000
01/07/26
2
2
1,432
24 Cottage Place, Old Saybrook, CT
0.63
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
367 Main Street #B32, Old Saybrook, CT 06475
0.04
$485,200
2
2
1,237
Off Market
367 Main Street #E-6, Old Saybrook, CT 06475
0.04
$542,400
2
2.5
1,358
Off Market
367 Main Street, Old Saybrook, CT 06475
0.04
$555,000
2
2
1,042
Off Market
367 Main Street #15, Old Saybrook, CT 06475
0.06
$800,600
3
2
1,558
Off Market
367 Main Street #12, Old Saybrook, CT 06475
0.05
$706,100
2
2
1,234
Off Market
367 Main Street #34, Old Saybrook, CT 06475
0.05
$863,500
3
2
1,477
Off Market
367 Main Street #38, Old Saybrook, CT 06475
0.05
$880,100
3
2
1,477
Off Market
367 Main Street #47, Old Saybrook, CT 06475
0.05
$727,700
3
2
1,477
Off Market
367 Main Street #30, Old Saybrook, CT 06475
0.05
$629,900
2
2
1,042
Off Market
367 Main Street #4, Old Saybrook, CT 06475
0.05
$601,400
2
2
1,042
Off Market
12 Maple Avenue, Old Saybrook, CT 06475
0.08
$474,300
2
1
772
Off Market
7 North Street, Old Saybrook, CT 06475
0.09
$508,000
3
1
864
Off Market

Local Information

  • Map ViewExplore the area around 385 Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1883
0.6 acre lot
2,381 sqft
$415/sqft

About this House

ANTIQUE COLONIAL BUILT IN 1883 IS REGISTERED WITH THE NATIONAL HISTORIC REGISTER OF HISTORIC PLACES. HOME HAS GREAT CHARACTER. FIRST FLOOR FEATURES OPEN FRONT PORCH, FRONT LIVING ROOM W/ FP, LIVING ROOM WITH FIREPLACE, GENEROUS EAT-IN KITCHEN, DEN/FAMILY ROOM W/FIREPLACE. MORNING STAIRCASE AND HALF BATH COMPLETE THE FIRST FLOOR. CURVED STAIRWAY TO THE SECOND FLOOR INCLUDES MASTER BEDROOM , 2 ADDITIONAL BEDROOMS AND FULL BATH. AN ADDITIONAL 2 BEDROOMS ON THE THIRD FLOOR COULD EASILY BE A GREAT ARTIST STUDIO IF 5 BEDROOMS WERE NOT NEEDED. THIRD FLOOR HAS A FLOORED WALK-IN ATTIC WITH PLENTY OF ROOM FOR STORAGE. MANY ORIGINAL FEATURES IN GOOD CONDITION. OIL HEAT W/ STEAM RADIATORS. NEWER SEPTIC SYSTEM W/RECENT WPC SEPTIC SYSTEM UPGRADE. ELECTRICAL AND FURNACE IN GOOD CONDITION. HOME DOES NEED SOME REPAIRS BUT IS PRICED RIGHT BELOW ASSESSED VALUE. GREAT CURB APPEAL. WONDERFUL OPPORTUNITY TO OWN ONE OF OLD SAYBROOK ORIGINAL MAIN STREET PROPERTIES. GREAT LEVEL BACKYARD AND GARDENS JUST WAITING TO BE RESTORED. WALKING DISTANCE TO TOWN CENTER AND SAYBROOK POINT. EASY ACCESS TO INTERSTATE 95 AND RTE 9 AND THE AMTRAK TRAIN STATION.
385 Main St, Old Saybrook, CT 06475 is a 5 bedroom, 2 bathroom, 2,381 sqft single-family home built in 1883. It last sold for $341,900 on Sep 11, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $987,500, with a rent estimate of $3,853/month.

Home Details for 385 Main St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1883
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.60 acres

Price and Tax history

DateEventPrice
Sep 11, 2017
Source: Smart MLS #P10239121
Sold
$341,900
Jul 24, 2017
Source: Agent Provided
Listed For Sale
$329,900
Sep 3, 1997
Source: N/A
Sold
$265,000

Market trends in Old Saybrook

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
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 385 Main St

  • What is 385 Main St estimated to be worth?
    Trulia's estimated value for 385 Main St in Old Saybrook, CT is $987,500.
  • What is the price history for 385 Main St?
    385 Main St in Old Saybrook, CT last sold for $341,900 in September 2017.
  • 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.
  • How big is the lot at 385 Main St?
    The lot at 385 Main St in Old Saybrook, CT is about 0.60 acres (26,136 sq ft).

Explore by feature - Pet Friendly

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