106 Cobblestone Way, Windsor, CT 06095
Property image
Property image
UNDER CONTRACT
0.93 ACRES

$399,900

  • 3 Beds
  • 3 Baths
  • 2,722 sqft (on 0.93 acres)

106 Cobblestone Way, Windsor, CT 06095

Est. Mortgage $2,934/mo*
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Home Highlights

Single-Family Home
Built in 1940
0.93 acre lot
$147/sqft
4 Car Garage

Local Information

  • Map ViewExplore the area around 106 Cobblestone Way.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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. Windsor is one of Connecticut's oldest towns-it was the state's first English settlement-and today it blends historic New England charm with parks, local restaurants, and easy access to major commuter routes and Bradley International airport. Windsor features amazing nature resources for all to enjoy. Northwest Park - Nature Center is the town's signature destination, featuring nearly 500 acres, 12 miles of hiking trails, a nature center, heritage farm animals, gardens, and seasonal events like concerts and educational programs. In winter, you can even rent cross-country skis and snowshoes. Windsor Meadows State Park offers access to the Connecticut River for walking, birdwatching, and kayaking. Windsor Center River Trail is a pleasant paved trail for walking or biking. Mill Brook Open Space provides quieter nature walks. History is a major part of Windsor's identity. The downtown area around the Windsor Town Green hosts community events throughout the year.
Last check for updates: about 14 hours ago
Listing courtesy of John Waters, (860) 985-4729
Berkshire Hathaway NE Prop., (860) 985-4729
Cheryl Bouchard, (860) 212-1018
Berkshire Hathaway NE Prop., (860) 688-7531
Source: Smart MLS, MLS#24201236
Also Listed on Smart MLS, Berkshire Hathaway HomeServices New England Properties.

Home Details for 106 Cobblestone Way

Interior Features

Interior Details
Basement: Full,Storage Space,Interior Entry,ConcreteNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Sun Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2722 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Ceiling Fan(s),Window Unit(s)Has HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Enclosed, Porch, Deck, PatioExterior: Rain Gutters, GardenFoundation: Block, Concrete PerimeterGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 8Parking: Attached,Detached,Paved,Driveway,Asphalt
Pool
Pool: Concrete, Fenced, In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2722 Square Feet

Days on Market

Days on Market: 27

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Farm House
Building
Construction Materials: Clapboard, CedarNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 777642

Price & Status

Price
List Price: $399,900Price Per Sqft: $147
Status Change & Dates
Off Market Date: Sun Aug 30 2026Possession Timing: Negotiable

Active Status

MLS Status: Under Contract

Location

Direction & Address
City: Windsor
School Information
Elementary School: Per Board of EdJr High / Middle School: Sage ParkHigh School: Windsor

Agent Information

Listing Agent
Listing ID: 24201236

Building

Building Area
Building Area: 2722 Square Feet

Community

Community Features: Library, Park, Playground, Public Rec Facilities, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 0.93 acres

Energy

Energy Efficiency Features: Windows

Miscellaneous

BasementMls Number: 24201236Zillow Contingency Status: Under ContractAttic: NoneAttribution Contact: (860) 985-4729Above Grade Unfinished Area: 2722

Additional Information

LibraryParkPlaygroundPublic Rec FacilitiesShopping/Mall

Around this home

What Locals Say about Windsor

At least 159 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 88 % Say parking is easy

  • 87 % Say it's dog friendly

  • 78 % Say streets are well-lit

  • 77 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 70 % Say there's holiday spirit

  • 69 % Say there's wildlife

  • 69 % Say it's quiet

  • 67 % Say there are sidewalks

  • 65 % Say kids play outside

  • 55 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 46 % Say it's walkable to restaurants

  • 46 % Say it's walkable to grocery stores

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Keyonna
    "Quiet and everyone keeps to themselves. Only a little noisy during the summer time due to motorcycles."
    0
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  • Zonoui Smith Jr.
    "I see dogs walked all the time. Some people don’t pick up after them. Also some people let their dogs walk to far into residence yards to use the bathroom "
    0
    Flag
  • Fenn.nathaniel
    "I've lived in this neighbourhood for about 15 years in love that is close to everything and far away from the hustles and bustles of the city."
    10
    Flag
  • Sherianne10315
    "Windsor has a small town feel. People help each other and come together when others are in need. Local farms and shop owners are friendly."
    0
    Flag
  • Kimberlydbigelow
    "I have lived in Windsor for 5 years. It has been the perfect location! I work in downtown Hartford and I take the bus into the city from a commuter lot in my town. It’s a relaxing 15min ride into and out of Hartford and as close as I am to the capital, Windsor is cute with lots of farms and the small, quaint town feel I was looking for. I’m loving it!"
    1
    Flag
  • Unspecified
    "Lots of town activities! Stuff on the green, local businesses, small town feel! Diverse community and polite town members"
    1
    Flag
  • Unspecified
    "There are Town green events all the time! Numerous walking trails filled with people. Strong sense of community. Working with locals is the norm in terms of hiring services."
    0
    Flag
  • Ashley W.
    "Los of people outside walking and a very quiet area very close to the highway. Good sense of community very safe and friendly neighborhood. Can walk to gas or food and close to the center of town and a lot of schools too!"
    0
    Flag
  • G.girardin
    "It’s a friendly and diversified neighborhood. Great walking neighborhood even at night. We’ve lived in Windsor for 35 years and feel very safe here. This is our third neighborhood . We’ve never had any issues. "
    0
    Flag
  • Sarah L.
    "Poquonock school is a wonderful community all the parks are very safe and the parks & rec programs are great"
    0
    Flag
  • Sam B.
    "Great place to stay and bring up a family great school system whatever they are ranked now you have Amazon JCP and others job market is good Parks swimming pools library good shop name it and you have it"
    0
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  • Sam B.
    "Great place to live grow work Bus and Uber available Mixed crowd Friendly people Great schools Parks pools Best library "
    0
    Flag
  • Sam B.
    "Great place to raise a family schools transport parks people are all great Town have a lot of activity like Shad Derby"
    0
    Flag
  • Shyra E.
    "My neighborhood is amazing it has good transit access and wonderful restaurants and parks hope this helps"
    0
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  • Carol J. M.
    "I live in this area for 1 year in a 55 and over community and love it! Lots of traffic on 91 and 291 that I do not like."
    1
    Flag
  • Nbjackson
    "Usually on the town green, farmers market, summer outdoor concerts, parades, Halloween event, holiday events, craft fairs"
    0
    Flag
  • Bonny E.
    "Yes dogs are always being walked in this area. They are great here. Kids always playing too. Neighbors helping neighbors. People look out for each other"
    0
    Flag
  • Jeffery I.
    "There are many events and good parks in town. however, you need the spend time finding them. unless you have lived hear for a long time or are active in town it can be hard to find stuff to do."
    0
    Flag
  • Me
    "my neighborhood is awesome, quiet, clean, with sidewalks, and walking trails. The HOA takes care of all the grounds maintenance and all snow removal"
    1
    Flag
  • Angie R.
    "recreation Dept has great programs parks are well maintained school system is getting back on track great family friendly town"
    0
    Flag
  • Me
    "Windsor is a small town. Although there are some rough areas but overall its quiet and safe. Schools are subpart.and taxes are high"
    1
    Flag
  • Wendy S.
    "during the summer they have concerts on the green down town. nice place tp live. quite contry living"
    0
    Flag
  • Me
    "I have lived here for 12 and I am very happy. the neighborhood is quiet and safe the streets are clean and well light"
    0
    Flag
  • ReginaJ
    "Live in the harvest Lane neighborhood for the last 9 years. One of the best places to live in the state. A very sort after neighborhood to live. Took us a while to get a house, because no one moves from it. Unless they are retiring and moving to Florida. The trails that are connected off the street that leads to Northwest Park and the reservoir for hiking are incredible. The family atmosphere is that of an extended family. The kids, the parents even the pets all know each other. We can’t ask for more from such a tranquil place we live in with so much harmony and love. #HarvestLane4Life "
    0
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  • Amy C.
    "Windsor is a town with strong resources and traditions. It has reasonable housing prices and lots of diversity. "
    0
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  • Carol J. M.
    "We have coffee 9am - 11am once a month and other social events. Dog friendly. Neighbors are very friendly."
    0
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  • Shanyelle.hamilton
    "Public transportation is easily accessible and downtown Hartford is 15 minutes from Wilson and 30 minutes from the town center by bus or car."
    0
    Flag
  • Shanyelle.hamilton
    "There are plenty of family friendly events in Windsor or the surrounding area. Every Halloween we have Nightmare on Broad Street for kids of all ages to have safe fun."
    0
    Flag
  • Lisanickersondouglas
    "Great schools / diverse community. Easy highway access. Lots of parks and trails for walking. Many annual events for kids and families. "
    0
    Flag
  • Amani R.
    "We have a yearly block party at each of the local parks. They are usually well attended and snacks are provided. "
    0
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  • Gchekas
    "Short commute, less than five minutes to work. Lot of industry on Day Hill Road, plenty of work for manufacturing industry. "
    0
    Flag

Market trends in Windsor

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
55
11MoM

Home Value

Trulia Estimate
$421K
Since last month
Increased$10K (+2.5%)
Since last year
Decreased$21K (-4.7%)
Since last sale
Increased$160K (+61.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +67% in the last 10 years
MonthEstimated value
2026
September 2026$420K
August 2026$410K
July 2026$453K
June 2026$458K
May 2026$457K
April 2026$450K
March 2026$448K
February 2026$426K
January 2026$429K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
621 Kennedy Road, Windsor, CT
0.14
Single-Family Home
$260,000
08/14/26
3
1.5
1,826
17 Box Turtle Lane, Windsor, CT
0.09
Single-Family Home
$500,000
12/30/25
4
2.5
2,095
501 Kennedy Road, Windsor, CT
0.17
Single-Family Home
$486,000
12/12/25
3
2.5
1,644
608 Kennedy Road, Windsor, CT
0.13
Single-Family Home
$426,000
03/31/26
4
2
1,399
40 Alden Road, Windsor, CT
0.49
Single-Family Home
$340,000
02/20/26
4
3
2,110
65 Alden Road, Windsor, CT
0.54
Single-Family Home
$350,000
09/15/26
4
2.5
2,159
61 Winthrop Road, Windsor, CT
0.41
Single-Family Home
$470,000
12/29/25
4
2.5
2,036
680 Kennedy Road, Windsor, CT
0.28
Single-Family Home
$412,000
01/23/26
4
2
1,848
14 Alden Road, Windsor, CT
0.42
Single-Family Home
$410,000
10/15/25
4
1.5
2,515

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
591 Kennedy Road, Windsor, CT 06095
0.07
$379,800
3
2
1,294
Off Market
17 Box Turtle Lane, Windsor, CT 06095
0.09
$500,000
4
2.5
2,095
Recently Sold
608 Kennedy Road, Windsor, CT 06095
0.13
$426,000
4
2
1,399
Recently Sold
621 Kennedy Road, Windsor, CT 06095
0.14
$260,000
3
1.5
1,826
Recently Sold
501 Kennedy Road, Windsor, CT 06095
0.17
$486,000
3
2.5
1,644
Recently Sold
122 Pilgrim Drive, Windsor, CT 06095
0.23
$421,400
3
2.5
1,982
Off Market
108 Pilgrim Drive, Windsor, CT 06095
0.24
$467,100
3
3
2,037
Off Market
468 Kennedy Road, Windsor, CT 06095
0.24
$421,900
5
2
2,114
Off Market
86 Glenwood Drive, Windsor, CT 06095
0.27
$391,400
3
1.5
1,591
Off Market
680 Kennedy Road, Windsor, CT 06095
0.28
$412,000
4
2
1,848
Recently Sold
83 Glenwood Drive, Windsor, CT 06095
0.28
$433,200
3
1.5
1,328
Off Market
32 Bradford Drive, Windsor, CT 06095
0.33
$470,400
4
2
1,766
Off Market

Price and Tax history

DateEventPrice
Aug 31, 2026
Source: Smart MLS #24201236
Pending
$399,900
Aug 24, 2026
Source: Smart MLS #24201236
Listed For Sale
$399,900
Feb 27, 2006
Source: Smart MLS #G405927
Sold
$260,000
Dec 12, 2005
Source: N/A
Sold
$269,900
Jan 22, 2002
Source: N/A
Sold
$157,000

LGBTQ Local Legal Protections

John Waters, Berkshire Hathaway NE Prop., (860) 985-4729
Agent Phone: (860) 985-4729
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 106 Cobblestone Way

  • What is the estimated monthly payment for 106 Cobblestone Way?
    Based on a $399,900 list price with 20% down at today's rates, the estimated monthly payment for 106 Cobblestone Way in Windsor, CT is approximately $2,973 (about $2,178 principal & interest, $720 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Windsor?
    Residents describe Windsor, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Windsor, CT.
  • What are the closest schools to 106 Cobblestone Way?
    The closest schools to 106 Cobblestone Way in Windsor, CT are John F. Kennedy School (Elementary, rated 4/10), Oliver Ellsworth School (Pre-K/Elementary), Sage Park Middle School (rated 6/10).
  • What is 106 Cobblestone Way estimated to be worth?
    Trulia's estimated value for 106 Cobblestone Way in Windsor, CT is $421,400.
  • Does 106 Cobblestone Way have air conditioning?
    Yes, 106 Cobblestone Way in Windsor, CT has air conditioning.
  • Does 106 Cobblestone Way have a pool?
    Yes, 106 Cobblestone Way in Windsor, CT has a pool.
106 Cobblestone Way, Windsor, CT 06095 is a 3 bedroom, 3 bathroom, 2,722 sqft single-family home built in 1940. This property is currently available for sale and was listed by Smart MLS on Aug 24, 2026. The MLS # for this home is MLS# 24201236.