37 Pilgrim Drive
Windsor, Connecticut 06095
- Beds
- 4
- Baths
- 2
- SqFt
- 1,886
- Acres
- 0.80
- Year Built
- 1959
- Property Type
- Single Family

Matt Caiola
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About This Home
Discover the timeless appeal of this inviting Cape-style residence, ideally situated in a sought-after neighborhood known for its welcoming character. Offering four bedrooms and two full bathrooms, this home combines classic charm with thoughtful improvements and versatile living spaces designed to accommodate today's lifestyle. Step inside to a warm and comfortable interior where beautifully restored hardwood floors add a sense of craftsmanship and character throughout much of the home. The family room provides a cozy retreat, highlighted by a wood-burning stove that sets the perfect mood for quiet nights and gatherings with family and friends. A generous living area flows naturally into the formal dining space, where hardwood floors and a glass slider create an effortless connection to the outdoors. Whether hosting a festive holiday meal or enjoying a relaxed evening at home, this space offers an inviting setting for every occasion. The kitchen is both functional and welcoming, featuring plentiful storage, a casual dining area, and freshly installed flooring. The first floor also includes two bedrooms with hardwood floors, offering exceptional flexibility for guests, a home office, or those seeking convenient single-floor accommodations. A full bathroom with tile flooring completes this level.
Key Facts
- City/Town
- Windsor
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1959
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,886 sq ft
- Lot Size
- 0.80 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $6,986 / Annually
Market Snapshot
The Windsor Market
Single Family · trailing 12 months
Active Listings
23
42 under contract
Median List Price
$439,900
23 active listings
Median Closed Price
$381,000
258 sales
Median Days on Market
16
23 active listings
Median $ / Sq Ft
$230
23 active listings
Sale-to-List Ratio
103.1%
258 sales
How this home compares
List Price
$455,000
vs $439,900 median
In line with median
Price / Sq Ft
$241
vs $230 median
In line with median
Days on Market
0 days
vs 16 days median
16 days fresher than median
Based on 23 active and 258 closed sales (trailing 12 mo) of single family in Windsor. Source: SmartMLS · As of August 16, 2026.
Location
37 Pilgrim Drive, Windsor, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$2,342
- Property Taxes$582
- Insurance$152
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windsor
- Neighborhood
- N/A
- County
- Hartford
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1959
- New Construction
- No/Resale
- Living Area
- 1,886 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Electric RangeConvection RangeMicrowaveRefrigeratorDishwasher
- Basement
- FullUnfinishedInterior AccessConcrete FloorFull With Hatchway
- Additional Rooms
- Sitting Room
Exterior & Lot
- Lot Size
- 0.80 acres
- Zoning
- RES-AA
- Garage / Parking
- 2 garage spaces4 total parking spacesAttached GarageOff Street ParkingDrivewayPrivatePavedAsphalt
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Aluminum
- Color
- WHITE
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Fruit TreesGuttersGarden AreaPatio
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $6,986 / Annually
- Days on Market
- 0
- MLS #
- 24197082
- MLS Status
- Active
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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 8/16/2026. 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 8/16/2026 at 12:05 AM UTC.