Skip main navigation
Off market
  • $527,100

    43 Pennywise Ln, Old Saybrook, CT 06475

    2beds
    1,438sqft
    Single Family Residence
    Built in ----
    -- sqft lot
    $527,100 Zestimate®
    $367/sqft
    $3,254 Estimated rent

    Home value

    $527,100

    $485,000 - $580,000

    $3,254/mo

    Zestimate® history
    Loading
    Loading...

    Owner options

    List your home for rent

    $3,254/mo

    Rent Zestimate®

    Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.

    Learn more

    $3,254/mo

    Rent Zestimate®

    Refinance and save

    $3,658/mo

    Est. payment

    Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.

    See today's rates

    $3,658/mo

    Est. payment

    Explore your selling options

    Work with a Zillow partner agent

    Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.

    Get started

    List with your own agent

    Get your home in front of millions of buyers by listing it on Zillow.

    Learn how to do it

    Sell it yourself

    Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).

    List your home

    What's special

    Office spaceSun filled napping cornerGleaming wood countersFire pitReading nookBeautiful decorative fireplaceEat-in kitchen

    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" and unplug for the season! Available Dec 15, 2025 - May 31, 2026. Negotiable. Available December 15, 2025 - May 31, 2026.

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Zillow last checked:

    Listing updated:

    Source: Zillow Rentals

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 2
    • Full bathrooms: 2
    Heating
    • Baseboard
    Cooling
    • Window Unit
    Appliances
    • Included: Dishwasher, Dryer, Freezer, Microwave, Oven, Refrigerator, Washer
    • Laundry: In Unit
    Features
    • Flooring: Hardwood
    • Furnished: Yes
    Interior area
    • Total interior livable area: 1,438 sqft

    Property

    Parking
    • Parking features: Off Street
    • Details: Contact manager
    Features
    • Exterior features: Heating system: Baseboard
    Details
    • Parcel number: OSAYM030B016L

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence

    Community & neighborhood

    Location
    • Region: Old Saybrook

    HOA & financial

    Other fees
    • Deposit fee: $3,000

    Other

    Other facts
    • Available date: 12/15/2025

    Price history

    DateEventPrice
    1/1/2026Listing removed$3,000$2/sqft
    Source: Zillow Rentals Report a problem
    11/20/2025Listed for rent$3,000+81.8%$2/sqft
    Source: Zillow Rentals Report a problem
    6/9/2020Sold$260,000+25%$181/sqft
    Source: Public Record Report a problem
    3/7/2020Listing removed$1,650$1/sqft
    Source: William Pitt Sotheby's International Realty #170268225 Report a problem
    2/3/2020Listed for rent$1,650$1/sqft
    Source: William Pitt Sotheby's International Realty #170268225 Report a problem
    7/20/2018Sold$208,000-9.5%$145/sqft
    Source: Smart MLS #170064795 Report a problem
    6/20/2018Pending sale$229,900$160/sqft
    Source: Berkshire Hathaway HomeServices New England Properties #170064795 Report a problem
    5/7/2018Price change$229,900-2.1%$160/sqft
    Source: Berkshire Hathaway HomeServices New England Properties #170064795 Report a problem
    3/25/2018Listed for sale$234,9000%$163/sqft
    Source: Berkshire Hathaway HomeServices New England Properties #170064795 Report a problem
    2/20/2018Listing removed$235,000$163/sqft
    Source: REMAX Valley Shore Genovali RE #N10176909 Report a problem
    10/21/2016Price change$235,000-1.6%$163/sqft
    Source: REMAX Valley Shore Genovali Realty #N10176909 Report a problem
    9/5/2016Price change$238,900-2.4%$166/sqft
    Source: William Raveis Real Estate #N10125126 Report a problem
    5/23/2016Listed for sale$244,900+226.5%$170/sqft
    Source: William Raveis Real Estate #N10125126 Report a problem
    1/26/2009Sold$75,000-42.3%$52/sqft
    Source: Public Record Report a problem
    7/26/2000Sold$130,000$90/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$4,199 +2%$270,900
    2024$4,118 +27.6%$270,900 +71.7%
    2023$3,227 +1.8%$157,800
    2022$3,169 +0.2%$157,800
    2021$3,164 $157,800
    2020$3,164 +1.4%$157,800 -0.1%
    2019$3,119 +6.8%$157,900 +6%
    2018$2,920 -0.3%$149,000
    2017$2,929 +2.1%$149,000
    2016$2,870 +2.4%$149,000
    2015$2,803 +1.7%$149,000
    2014$2,757 +7.9%$149,000 -11.3%
    2013$2,554 +4%$168,000
    2012$2,456 +4%$168,000
    2011$2,362 +4.6%$168,000
    2009$2,258 +13.6%$168,000 +33.9%
    2007$1,988 +8.5%$125,500
    2005$1,832 +5.8%$125,500
    2004$1,732 -25.9%$125,500 +15.9%
    2003$2,336 +9.1%$108,300
    2001$2,141 +42.9%$108,300 +6%
    1995$1,498 $102,200

    Find assessor info on the county website

    Neighborhood: Old Saybrook Center

    Nearby schools

    GreatSchools rating
    Get pre-qualified for a loan
    At Zillow Home Loans, we can pre-qualify you in as little as 5 minutes with no impact to your credit score.

    An equal housing lender. NMLS #10287.

    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
    $527,100
    2% more
    +$10,542
    With Zillow Showcase(estimated)
    $537,642