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66 Pennywise Lane, 
Old Saybrook, CT 06475

$1,395,000


4

Beds


4

Baths


2,425

Sq Ft


Single Family

Pending

Listed by

Joel Lucas

Last updated:

November 11, 2025, 08:32 AM

MLS#

24128259

Source:

CT

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About This Home

66 Pennywise Lane

In the heart of Saybrook Village, this completely restored and remodeled vintage home blends modern convenience with timeless character, ideal for the discerning over-55 buyer who values both history and comfort or multi-generational buyers. The gourmet eat-in kitchen is a showpiece, with exposed beams, custom cabinetry, granite counters, a large island and vaulted ceilings, flowing seamlessly into the inviting living and den areas. French doors open from the living room to a private rear sitting porch, while a wood-burning fireplace enhances its warmth. Two gracious primary bedroom suites-one on the first floor-each feature fireplaces, elegant full baths and abundant closet space, providing flexibility and privacy. The upper level offers two additional bedrooms, one with its own fireplace, a full bath, and a balcony overlooking the main stairway. Throughout the home, wide-plank hickory hardwood floors, five fireplaces, and custom millwork highlight its craftsmanship. Modern upgrades include new Andersen windows, Therma-Tru doors, spray foam insulation, a high-efficiency 5-zone hydro-air system, on-demand hot water, natural gas service, and a new 1500-gallon septic system. A spacious mudroom with exterior access, dual laundry areas, and thoughtful design make daily living easy. Completing this exceptional property is a newly built oversized barn garage with workshop and finished living space, offering endless possibilities. Not in flood zone. Professional Photos to come!

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1790

Price Summary

1,395,000

$575 per Sq. Ft.

MLS #:

24128259

Last Updated:

November 11, 2025, 08:32 AM

Added:

1 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

2,425 Sq. Ft.


Structure

Structure

Architectural Style:

Antique, Colonial

Building Area:

2,425 Sq. Ft.

Year Built:

1790


Lot

Lot Size (Sq. Ft):

20,037


Finances & Disclosures

Finances

Price:

$1,395,000

Price per Sq. Ft:

$575 per Sq. Ft.

66 Pennywise Lane
Source:CT
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