108 Pilgrim Drive
Windsor, Connecticut 06095
- Beds
- 3
- Baths
- 3
- SqFt
- 1,791
- Acres
- 0.72
- Year Built
- 1962
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to this charming and classic, three bedroom, three full bath, Colonial nestled on a beautiful and level .72 acre lot in Pilgrim Village. The kitchen boasts an abundance of cabinetry and countertops, tile flooring and a pantry. While adding architectural dimension, the breezeway also offers entry from the front and backyard and access to the two car garage which provides additional attic storage space. Enjoy entertaining in the living room featuring hardwood flooring and a wood burning fireplace. The dining room, with hardwood flooring, is perfect for hosting holiday dinners. The heart of this home is in the expansive family room boasting a cathedral ceiling and a picture window. A full bath on the first level ensures convenience for the homeowner as well as for guests. At the end of your day, retreat to the second level to unwind in the spacious Primary bedroom featuring hardwood flooring, a newer skylight and its own designated full bath. There are also two additional bedrooms with beautiful hardwood flooring as well as a third full bath. Tremendous value is found in a newer roof (2022), an interior that has been professionally painted with a neutral and modern palette, newly refinished hardwood flooring and updated 200 amp electric. Moments away are popular destinations including the Farmington River where many locals enjoy kayaking, canoeing and fishing. Also nearby is Northwest Park with 473 acres of forest and walking trails. Come on...Let's take a look inside!
Key Facts
- City/Town
- Windsor
- Property / Style
- Single Family · Colonial
- Year Built
- 1962
- Days on Market
- 987 days
- Beds
- 3
- Baths
- 3 full
- Living Area
- 1,791 sq ft
- Lot Size
- 0.72 acres
- Property Taxes
- Not on file from MLS
Market Snapshot
The Windsor Market
Single Family · trailing 12 months
Active Listings
19
40 under contract
Median List Price
$439,900
19 active listings
Median Closed Price
$381,000
256 sales
Median Days on Market
40
19 active listings
Median $ / Sq Ft
$215
19 active listings
Sale-to-List Ratio
103.2%
256 sales
How this home compares
List Price
$339,900
vs $439,900 median
22.7% below median
Price / Sq Ft
$190
vs $215 median
11.6% below median
Days on Market
987 days
vs 40 days median
947 days longer than median
Based on 19 active and 256 closed sales (trailing 12 mo) of single family in Windsor. Source: SmartMLS · As of July 29, 2026.
Location
108 Pilgrim Drive, Windsor, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,733
- Property Taxes$0
- Insurance$113
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windsor
- County
- Hartford
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1962
- Living Area
- 1,791 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Windsor
Interior
- Heating
- BaseboardZoned
- Cooling
- Ceiling FansWhole House FanWindow Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Interior Features
- Auto Garage Door OpenerCable - Available
Exterior & Lot
- Lot Size
- 0.72 acres
- Garage / Parking
- Attached Garage
- Waterfront Details
- Not Applicable
- Construction
- Vinyl SidingAluminum
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGutters
- Lot Description
- Level LotLightly Wooded
Listing & Financials
- Days on Market
- 987
- MLS #
- 170596821
- MLS Status
- Under Contract
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/29/2026 at 12:00 PM UTC.