2 Pennywise Ln, Old Saybrook, CT 06475
OFF MARKET

2 Pennywise Ln
Old Saybrook, CT 06475

  • 4 Beds
  • 4.5 Baths
  • 2,616 sqft (on 0.25 acres)

$929,800

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $6,180/mo*
Refinance Your Home

$929,800

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $6,180/mo*
Refinance Your Home
4 Beds
4.5 Baths
2,616 sqft
(on 0.25 acres)

Local Information

Map showing home location
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Commute Destination

Description

This single-family home is located at 2 Pennywise Ln, Old Saybrook, CT. 2 Pennywise Ln is in Old Saybrook, CT and in ZIP code 06475. This property has 4 bedrooms, 5 bathrooms and approximately 2,616 sqft of floor space. This property has a lot size of 10890 sqft and was built in 1790.
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.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 2 Pennywise Ln

Interior Features

Heating & Cooling
Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Floors: Other

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other

Property Information

Year Built
Year Built: 1790
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 10890 sqft

Price History for 2 Pennywise Ln

DatePriceEventSource
10/21/2016$360,000Sold
Smart MLS #N10163556
09/01/2016$399,900Listed For SaleAgent Provided

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
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Comparable Sales for 2 Pennywise Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
66 Pennywise Lane, Old Saybrook, CT
0.22
Single-Family Home
$1,495,000
12/01/25
4
3.5
2,425
3 Glen Drive, Old Saybrook, CT
0.18
Single-Family Home
$625,000
09/19/25
3
1.5
1,915
355 Main Street, Old Saybrook, CT
0.12
Single-Family Home
$707,500
12/19/25
3
1.5
2,194
24 Lynde Street, Old Saybrook, CT
0.34
Single-Family Home
$799,900
07/31/25
4
2.5
2,756
21 Cottage Place, Old Saybrook, CT
0.43
Single-Family Home
$650,000
12/02/25
3
3
1,720
19 Lynde Street, Old Saybrook, CT
0.33
Single-Family Home
$935,000
12/16/25
3
2.5
2,396
62 Lynde Street, Old Saybrook, CT
0.51
Single-Family Home
$600,000
07/18/25
4
2
1,830
18 Quarry Street, Old Saybrook, CT
0.48
Single-Family Home
$510,000
05/07/26
4
2
1,760
41 Farview Avenue, Old Saybrook, CT
0.48
Single-Family Home
$630,000
05/29/26
4
1.5
1,400
7 Willard St, Old Saybrook, CT
0.29
Single-Family Home
$425,000
06/11/25
3
1
1,215

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Pennywise Ln.
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

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2 Pennywise Ln, Old Saybrook, CT 06475 is a 4 bedroom, 5 bathroom, 2,616 sqft single-family home built in 1790. This property is not currently available for sale. 2 Pennywise Ln was last sold on Oct 21, 2016 for $360,000. The current Trulia Estimate for 2 Pennywise Ln is $929,800.