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

