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106 Cobblestone Way

Windsor, Connecticut 06095

ACTIVE - NEW$399,900
Beds
3
Baths
3
SqFt
2,722
Acres
0.93
Year Built
1940
Matt Caiola

Matt Caiola

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Pool4-Car Garage

About This Home

Welcome to this 2700 Sq. Ft. Colonial Farmhouse that is nestled on a level .93 acre parcel. This home features an abundnace of character and charm and is ideal for those who love to entertain. The expansive outdoor living area boasts a 20' x 40' inground pool with a new safety fence, newer pump, filter and patio. A large level yard offers privacy and is perfect for summer time activities. The first level floor plan offers a 16' x 18' family room that flows off of the kitchen. A formal dining room and living room feature hardwood floors. There is a cozy sunroom that can also accomodate a home office. The first level is completed by a beautifully remodeled full bathroom featuring a claw foot tub, double sink vanity and a custom walkin tile shower. You will enjoy the luxury and convenience of the first floor laundry and mudroom. On the second level there are three bedrooms and two additional full baths. The 15' x 20' primary bedroom features a private full bath, vaulted ceiling and a large walkin closet. Relax on the upper deck off of the primary bedroom that overlooks the inground pool and yard. There are a total of four garage bays offering more than ample storage for the car or power equipment enthusiast. The enclosed porch offers great space to relax and enjoy the cool summer evening breeze. This quiet low traffic location is in a desiable neighborhood, yet still offers a private setting.

Key Facts

City/Town
Windsor
Neighborhood
N/A
Property / Style
Single Family · Colonial,Farm House
Year Built
1940
Days on Market
0 days
Beds
3
Baths
3 full
Living Area
2,722 sq ft
Lot Size
0.93 acres
Garage / Parking
4 garage · 8 total
Property Taxes
$7,120 / Annually

Market Snapshot

The Windsor Market

Single Family · trailing 12 months

Median Days on Market

25

25 active listings

Median $ / Sq Ft

$227

25 active listings

Sale-to-List Ratio

102.9%

258 sales

How this home compares

List Price

$399,900

vs $399,900 median

In line with median

Price / Sq Ft

$147

vs $227 median

35.2% below median

Days on Market

0 days

vs 25 days median

25 days fresher than median

Based on 25 active and 258 closed sales (trailing 12 mo) of single family in Windsor. Source: SmartMLS · As of August 25, 2026.

Location

106 Cobblestone Way, Windsor, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,780

per month

  • Principal & Interest$2,054
  • Property Taxes$593
  • Insurance$133
  • 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
Colonial,Farm House
Year Built
1940
New Construction
No/Resale
Living Area
2,722 sq ft

Schools

Elementary
Per Board of Ed
High
Windsor

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Ceiling FansWindow Unit
Laundry
Main Level
Appliances
Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullStorageInterior AccessConcrete FloorFull With Hatchway
Interior Features
Cable - Available
Additional Rooms
Mud Room

Exterior & Lot

Lot Size
0.93 acres
Zoning
Res-AA
Garage / Parking
4 garage spaces8 total parking spacesAttached GarageDetached GaragePavedDrivewayPavedAsphalt
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Pool
ConcreteSafety FenceIn Ground Pool
Construction
ClapboardCedar
Roof
Asphalt Shingle
Foundation
BlockConcrete
Exterior Features
Porch-EnclosedPorchDeckGuttersGarden AreaPatio
Lot Description
Lightly WoodedLevel Lot

Listing & Financials

Property Taxes
$7,120 / Annually
Days on Market
0
MLS #
24201236
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

John Waters

(860) 985-4729

Berkshire Hathaway NE Prop.

(860) 688-7531

Co-Listed By

Cheryl Bouchard

Berkshire Hathaway NE Prop.

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/25/2026. 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 8/25/2026 at 4:10 AM UTC.