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$2,900

  • Sold
  • Closed
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,436 Sq. Ft.
  • Updated 5 days ago
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See This Home
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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.

Full Property Details for 43 Pennywise Ln

General

  • Rent: $2,900
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24141368
  • Added to Site: 57 day(s) ago

Rental Information

  • Rental Type: Winter Furnished, Month-to-Month Furnished, Short Te
  • Lease Terms: Per Month
  • Short Term: Yes

Interior

  • Number of Rooms: 4
  • Appliances: Oven/Range, Microwave, Refrigerator, Freezer, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2
  • Primary Bedroom: Primary Bedroom - Remodeled, Beams, Full Bath, Hardwood Floor, Main
  • Bedroom 1: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Family Room: Family Room - Beams, Book Shelves, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Beams, Hardwood Floor, Main
  • Laundry: Lower Level

Exterior

  • Color: Grey

Location

  • County: Middlesex
  • Driving Directions: Old Boston Post Road to Pennywise or Main Street to Pennywise.

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Aluminum
  • Basement Desc.: Partial
  • Square Feet: 1,436
  • Above Ground: 1,436 Sq. Ft.
  • Year Built: 1800

Lot Features

  • Lot Size (Acres): 0.23
  • Zoning: A
  • Lot Description: Level Lot, Cleared

Financial Considerations

  • Tenant Pays: Credit Check, Electricity, Heat, Water

Disclosures and Reports

  • Property ID: 1026701

Listed by William Pitt Sotheby's Int'l, Phoebe Finch
Sold by Unrepresented Buyer, Unrepresent Buyer/Tenant

Listing agent

— 43 Pennywise Ln —

  • Phoebe Finch

    William Pitt Sotheby's Int'l

Agent Contact: (617) 645-3907 Office Contact: (203) 245-6700

Schools serving 43 Pennywise Ln

School District:Old Saybrook School District
NameGradesDistance
Kathleen E. Goodwin School
80 Old Boston Post Road, Old Saybrook, CT 06475
PK-30.2 mi
Old Saybrook Middle School
60 Sheffield Street, Old Saybrook, CT 06475
4-80.4 mi
Old Saybrook Senior High School
1111 Boston Post Road, Old Saybrook, CT 06475
9-120.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price History for 43 Pennywise Ln

Date
Details
Price
Change
Source
1/10/2026
Sold
$2,900
-3.33%
MLS
11/20/2025
Listed
$3,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by William Pitt Sotheby's Int'l, Phoebe Finch
Sold by Unrepresented Buyer, Unrepresent Buyer/Tenant

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43 Pennywise Lane, Old Saybrook, CT 06475 (MLS# 24141368) is a Single Family property that was sold at $2,900 on January 10, 2026. Want to learn more about 43 Pennywise Lane? Do you have questions about finding other real estate for sale or rent in Old Saybrook? You can browse all Old Saybrook rentals or contact a Coldwell Banker agent to request more information.