Skip main navigation
House for rent
  • Accepts Zillow applications
    $3,000/mo

    43 Pennywise Ln, Old Saybrook, CT 06475

    2beds
    1,438sqft

    This listing now includes required monthly fees in the total price. Learn more

    Fast & easy Zillow application.

    This property accepts Zillow applications. Click 'Apply now' to fill out the online form once and apply to as many participating properties as you want. Just $35 for 30 days.

    Single family residence
    Available Mon Dec 15 2025
    No pets
    Window unit
    In unit laundry
    Off street parking
    Baseboard

    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.
    3 days
    |
    --
    |
    --
    |
    Travel times

    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 & HOA

    Location
    • Region: Old Saybrook

    Financial & listing details

    • Lease term: 6 Month

    Price history

    DateEventPrice
    11/20/2025Listed for rent$3,000+81.8%$2/sqft
    Source: Zillow Rentals
    6/9/2020Sold$260,000+25%$181/sqft
    Source: Public Record
    3/7/2020Listing removed$1,650$1/sqft
    Source: William Pitt Sotheby's International Realty #170268225
    2/3/2020Listed for rent$1,650$1/sqft
    Source: William Pitt Sotheby's International Realty #170268225
    7/20/2018Sold$208,000-9.5%$145/sqft
    Source: Smart MLS #170064795

    Neighborhood: Old Saybrook Center