106 Cobblestone Way
Windsor, Connecticut 06095
- Beds
- 3
- Baths
- 3
- SqFt
- 2,722
- Acres
- 0.93
- Year Built
- 1940
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
25
42 under contract
Median List Price
$399,900
25 active listings
Median Closed Price
$385,000
258 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per 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
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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.