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$3,000 Total Monthly Price

43 Pennywise Ln, Old Saybrook, CT 06475

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What This House Offers

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.

Unit

  • $3,000 Total Monthly Price
  • 2 Beds
  • 2 Baths
  • Available Now

Home Features

  • Air Conditioning
  • Hardwood Floors
  • Refrigerator
  • Tile Floors

Community Features

  • Controlled Access
  • Laundry Facilities
  • Package Service

43 Pennywise Ln is a single-family home for rent in Old Saybrook, CT

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What's nearby 43 Pennywise Ln

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Get In Touch

Property Address:
43 Pennywise Ln,
Old Saybrook, CT 06475
Listed by
Phoebe Schreiner | William Pitt Sotheby's International Realty
More Information:
View Property Website

Area Scores

Walkability

Fairly walkable40 / 100

Transit

Limited public transit30 / 100

Driveability

Exceptionally drivable100 / 100

Bikeability

Fairly bikeable50 / 100

Scores provided by

Soundscore

Active78 / 100

Scores provided by
HowLoud

Travel and Transit

Commuter Rail
2 min Drive
Commuter Rail
8 min Drive
Airport
Tweed/New Haven
38 min Drive
Tweed-New Haven

Local Education

Primary and Secondary Schools

6 rating

Kathleen E. Goodwin School

Grades PK-5

Public

8 rating

Old Saybrook Middle School

Grades K-8

Public

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St John School

Grades PK-8

Private

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Joshua Center Shoreline CDT

Grades 9-12

Private

8 rating

Old Saybrook Senior High School

Grades 9-12

Public

Data provided by GreatSchools.org © 2026. All rights reserved.

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Discover Southern Middlesex County, Old Saybrook, CT

Shopping Centers

Shoppers will appreciate 43 Pennywise Ln proximity to 785 Boston Post Rd, 196-210 Main Street, and 880 Boston Post Road Strip Center. 785 Boston Post Rd is 0.5 miles away, and 196-210 Main Street is within a 9 minute walk.

Commuting

With a TransitScore of 30, 43 Pennywise Ln has limited public transit, including 5 transit stops within 45.9 miles. Transit options include Old Saybrook and Westbrook.

Airports

Living in Southern Middlesex County provides easy access to Tweed/New Haven, located just 39 minutes from 43 Pennywise Ln.

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