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!
Sold for $1,495,000
$1,495,000
66 Pennywise Lane, Old Saybrook, CT 06475
4beds
2,425sqft
Single Family Residence
Built in 1790
0.46 Acres Lot
$1,547,700 Zestimate®
$616/sqft
$6,172 Estimated rent
Home value
$1,547,700
$1.42M - $1.67M
$6,172/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Joel Lucas (860)304-9150,
Coldwell Banker Realty 203-245-4700
Bought with:
Heather Dacey, REB.0793752
William Raveis Real Estate
Source: Smart MLS,MLS#: 24128259
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Remodeled, Bedroom Suite, Fireplace
- Level: Main
Bedroom
- Features: Remodeled, Bedroom Suite, Fireplace, Full Bath
- Level: Upper
Bedroom
- Features: Remodeled, Hardwood Floor
- Level: Upper
Bedroom
- Features: Remodeled, Fireplace, Hardwood Floor
- Level: Upper
Dining room
- Level: Main
Living room
- Features: Remodeled, Beamed Ceilings, Fireplace
- Level: Main
Heating
- Forced Air, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Range, Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Gas Water Heater, Tankless Water Heater
- Laundry: Main Level
Features
- Wired for Data, Open Floorplan
- Basement: Full
- Attic: Crawl Space,Access Via Hatch
- Number of fireplaces: 5
Interior area
- Total structure area: 2,425
- Total interior livable area: 2,425 sqft
- Finished area above ground: 2,425
Property
Parking
- Total spaces: 8
- Parking features: Barn, Detached, Paved, Driveway
- Garage spaces: 3
- Has uncovered spaces: Yes
Features
- Patio & porch: Patio, Porch
- Exterior features: Lighting, Sidewalk, Awning(s), Garden
Lot
- Size: 0.46 Acres
- Features: Landscaped, Open Lot
Details
- Additional structures: Barn(s), Guest House
- Parcel number: 1026609
- Zoning: A
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Antique
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter, Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1790
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Underground Utilities
Community & neighborhood
Community
- Community features: Near Public Transport, Golf, Health Club, Library, Private School(s), Public Rec Facilities, Shopping/Mall
Location
- Region: Old Saybrook
- Subdivision: Saybrook Point
Price history
| Date | Event | Price |
|---|---|---|
| 12/1/2025 | Sold | $1,495,000+7.2%$616/sqft |
Source:  Smart MLS #24128259 Report a problem | ||
| 9/28/2025 | Pending sale | $1,395,000$575/sqft |
Source: Smart MLS #24128259 Report a problem | ||
| 9/26/2025 | Listed for sale | $1,395,000+91.1%$575/sqft |
Source: Smart MLS #24128259 Report a problem | ||
| 4/27/2018 | Sold | $730,000-5.1%$301/sqft |
Source: Smart MLS #170053312 Report a problem | ||
| 3/8/2018 | Pending sale | $769,500$317/sqft |
Source: Executive Real Estate Inc. #170053312 Report a problem | ||
| 2/17/2018 | Listed for sale | $769,500+284.8%$317/sqft |
Source: Executive Real Estate Inc. #170053312 Report a problem | ||
| 11/6/2014 | Sold | $200,000-12.9%$82/sqft |
Source: Smart MLS #N354870 Report a problem | ||
| 9/15/2014 | Listed for sale | $229,500+53%$95/sqft |
Source: RE/MAX Valley-Shore #N354870 Report a problem | ||
| 2/10/1992 | Sold | $150,000$62/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $9,864 +2% | $636,400 |
| 2024 | $9,673 -19.1% | $636,400 +8.8% |
| 2023 | $11,959 +1.8% | $584,800 |
| 2022 | $11,743 +0.2% | $584,800 |
| 2021 | $11,725 +28.1% | $584,800 +28.1% |
| 2020 | $9,155 +1.5% | $456,600 +0% |
| 2019 | $9,016 +44.3% | $456,500 +43.1% |
| 2018 | $6,250 +2.6% | $318,900 +2.9% |
| 2017 | $6,091 +23.2% | $309,800 +20.6% |
| 2016 | $4,946 +2.4% | $256,800 |
| 2015 | $4,830 -23.6% | $256,800 -24.8% |
| 2014 | $6,320 +4.7% | $341,600 -14% |
| 2013 | $6,036 +4% | $397,100 |
| 2012 | $5,806 +4% | $397,100 |
| 2011 | $5,583 +4.6% | $397,100 |
| 2009 | $5,337 +10.7% | $397,100 +30.5% |
| 2007 | $4,822 +8.5% | $304,400 |
| 2005 | $4,444 +5.8% | $304,400 |
| 2004 | $4,201 -3.6% | $304,400 +50.7% |
| 2003 | $4,357 +9.1% | $202,000 |
| 2001 | $3,994 +35.9% | $202,000 +0.8% |
| 1995 | $2,938 | $200,410 |
Find assessor info on the county website
Neighborhood: 06475
Nearby schools
GreatSchools rating
- 6/10Kathleen E. Goodwin SchoolGrades: PK-4Distance: 0.2 mi
- 8/10Old Saybrook Middle SchoolGrades: 5-8Distance: 0.4 mi
- 8/10Old Saybrook Senior High SchoolGrades: 9-12Distance: 0.9 mi
Schools provided by the listing agent
- Elementary: Kathleen E. Goodwin
- High: Old Saybrook
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Middlesex County
- Old Saybrook
- 06475
- 66 Pennywise Lane
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