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$1,495,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,425 Sq. Ft.
  • 3 Car Garage
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See This Home
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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!

Full Property Details for 66 Pennywise Ln

General

  • Sold For: $1,495,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24128259
  • Added to Site: 142 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Exercise Room, Steam/Sauna, Workshop
  • Interior Features: Cable - Pre-wired, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 5
  • Appliances: Gas Range, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Remodeled, Bedroom Suite, Fireplace, Main
  • Bedroom 1: Bedroom - Remodeled, Bedroom Suite, Fireplace, Full Bath, Upper
  • Bedroom 2: Bedroom - Remodeled, Fireplace, Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Remodeled, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Remodeled, Beams, Fireplace, Main
  • Dining Room: Dining Room, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Barn, Lighting, Guest House, Patio, Underground Utilities, Sidewalk, Awnings, Porch, Garden Area
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 8
  • Parking: Barn, Detached Garage, Paved, Driveway

Location

  • County: Middlesex
  • Neighborhood: Saybrook Point
  • Driving Directions: Main Street to Pennywise Lane

School Information

  • Elementary School: Kathleen E. Goodwin
  • Middle School: Old Saybrook
  • Intermediate School: Per Board of Ed
  • High School: Old Saybrook

Community

  • Community Name: Saybrook Point

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial, Antique
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,425
  • Above Ground: 2,425 Sq. Ft.
  • Year Built: 1790

Lot Features

  • Lot Size (Acres): 0.46
  • Driveway/Sidewalk: Paved
  • Zoning: A
  • Lot Description: Professionally Landscaped, Open Lot

Financial Considerations

  • Assessment Amount: $636,400
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1026609

Meet the listing agent

Meet the listing agent
— 66 Pennywise Ln —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 66 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 & Sales History for 66 Pennywise Ln

Date
Details
Price
Change
Source
12/01/2025
Sold
$1,495,000
7.17%
MLS
9/26/2025
Listed
$1,395,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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66 Pennywise Lane, Old Saybrook, CT 06475 (MLS# 24128259) is a Single Family property that was sold at $1,495,000 on December 01, 2025. This property was listed by Joel Lucas from our Madison Office.Want to learn more about 66 Pennywise Lane? Do you have questions about finding other Single Family real estate for sale in Old Saybrook? You can browse all Old Saybrook real estate or contact a Coldwell Banker agent to request more information.