43 Pennywise Ln

1,436 Sq. Ft.
$25 / Sq. Ft.
1,436
Sq. Ft.
$25
per Sq. Ft.

Description

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first...Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to "hang your hat". Available September 15, 2026 - May 31, 2027. Also July and August at 6K per month.

Property Details for 43 Pennywise Lane

Basement Description
Partial
Direct Waterfront
No
Neighborhood
N/A
Style
Colonial
Swimming Pool
No
LISTING UPDATED: 01/21/2026 02:51 PM

Property Details for 43 Pennywise Lane

StatusActive
MLS #24150290
Days on Market16
Rental Incentives-
Available Date-
Lease Term-
Furnished-
Compass TypeRental
MLS TypeResidential Rental / Single Family Rental
Year Built1800
Lot Size0.23 AC / 10,018 SF
CountyMiddlesex County

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Phoebe V Finch
Add your commute

Building Information for 43 Pennywise Lane

Building/Complex43 Pennywise LnFloor-Stories-Pet Policy-Pet Policy DetailsNoYear Built1800Building Size-Lot Size0.23 AC / 10,018 SF

Property Information for 43 Pennywise Lane

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Old Boston Post Road to Pennywise or Main Street to Pennywise.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.28803
  • Longitude: -72.378426
  • Pets Allowed: No
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Freezer, Washer, Dryer
  • Cooling System: None
  • Heat Type: Hot Water
  • Attic YN: No
  • Fireplaces Total: 0
  • Laundry Room Info: Lower Level
  • Laundry Room Location: In basement
  • Rooms Total: 4
Room 1
  • Room Entry Order: 1
  • Room Features: Beams,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 2
  • Room Entry Order: 2
  • Room Features: Beams,Book Shelves,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 3
  • Room Entry Order: 3
  • Room Features: Remodeled,Beams,Full Bath,Hardwood Floor
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: Grey
  • Exterior Siding: Aluminum
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Smoking Allowed: No
  • Year Built: 1800
  • Year Built Source: Public Records
  • Living Area SQFT Per Public Records: 1436
Lot Information
  • Lot Description: Level Lot, Cleared
  • Parcel Number: 1026701
  • Sq Ft Est Heated Above Grade: 1436.0
  • Sq Ft Total: 1436.0
  • Zoning: A
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner
Rental
Rental
  • Rental Duration: Month-to-Month Furnished, Short Term Furnished, Academic Year Furnished

Schools near 43 Pennywise Lane

This home is within Old Saybrook School District.
Rating
School
Type
Grades
Distance
Public - PK to 4
Public - 5 to 8
Public - 9 to 12
Private - PK to 8
Rating
School
Distance
Kathleen E. Goodwin School
PublicPK to 4

Old Saybrook Middle School
Public5 to 8

Old Saybrook Senior High School
Public9 to 12

St John School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

43 Pennywise Lane is available for rent in Old Saybrook, CT 06475. This property was listed on January 21, 2026 by William Pitt Sotheby's Int'l, it's currently listed at $3,000. This listing's school district is Old Saybrook School District. Nearby schools include Kathleen E. Goodwin School, Old Saybrook Middle School and Old Saybrook Senior High School. 43 Pennywise Lane is a 2-bed, 2-bath, 1,436 sqft a property built in 1800.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Phoebe V Finch

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.