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37 Pilgrim Drive

Windsor, Connecticut 06095

ACTIVE - NEW$455,000
Beds
4
Baths
2
SqFt
1,886
Acres
0.80
Year Built
1959
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,076

per 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

Similar Properties

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Listed By

Andrea Rodriguez

(860) 331-5156

Eagle Eye Realty PLLC

(860) 263-9102

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.