27 Kennedy Road, Windsor, CT 06095
OFF MARKET

27 Kennedy Road
Windsor, CT 06095

  • 4 Beds
  • 2.5 Baths
  • 1,920 sqft (on 0.70 acres)

$508,100

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $3,602/mo*
Refinance Your Home

$508,100

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $3,602/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,920 sqft
(on 0.70 acres)

Local Information

  • Map ViewExplore the area around 27 Kennedy Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1978
Lot Size
0.7 acres
Living Area
1,920 sqft
Price/Sqft
$265
Parking
2 Car Garage

About this House

[Deadline for offers is Monday, 5/20 by 5pm] Stop the car! This could be the one! Not only will it become your permanent Staycation home with a beautifully maintained in-ground pool (new cover ($3k) & pool pump & filter, on .70 acre, current owner has made many improvements in the last few years including adding 2nd Floor CENTRAL AIR($11k) and split a/c downstairs ($4k), gorgeous ROSEWOOD hardwood floors and new carpeting ($10k), Kloter Farms shed ($8k) gazebo ($4k), converted f/p to gas ($6k) and a new GARAGE ($10k)in back for car enthusiasts or landscape business equipment. The home also boasts u/g sprinkler for the best yard in town, a 8kw Generac generator for when Mother Nature plays tricks on us. The floor plan is that of a traditional Colonial with the formal living room in the front of the home which flows into the dining room facing the back of the home and then through to the kitchen followed by the gas fireplaced family room. The half bath is off the front foyer. Upstairs, you will find four bedrooms with a full bathroom. The primary bedroom also has its own full bathroom. Washer and dryer are included and conveniently located on first floor. The home is nestled within a close-knit neighborhood and just 1/8 mile from historic Windsor's Palisado Avenue Just a short distance to Windsor's downtown area where you can enjoy shopping, dining, festivals, summer concerts and Farmers Market or head toward the highway (2 miles) to more grocery shopping, Target, HomeGoods & more dining options and so convenient for those commuting to Springfield or Hartford or those needing to hop the Amtrak train in the center for a quick trip to NYC. This home is waiting for you to open up the pool for your first pool party
27 Kennedy Road, Windsor, CT 06095 is a 4 bedroom, 3 bathroom, 1,920 sqft single-family home built in 1978. It last sold for $449,500 on Jun 18, 2024 (3% above the $434,700 asking price). It is currently off market. The Trulia Estimate is $508,100, with a rent estimate of $3,235/month.

Home Details for 27 Kennedy Road

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1920 Square Feet
Appliances & Utilities
Appliances: Electric Range, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Natural GasHas CoolingAir Conditioning: Central Air,DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PatioOther Structures: Shed(s), GazeboExterior: Underground SprinklerFoundation: Concrete PerimeterHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Garage Door Opener
Pool
Pool: In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1920 Square Feet

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 780761

Price & Status

Price
List Price: $434,700
Status Change & Dates
Off Market Date: Tue May 21 2024Possession Timing: Immediately

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Windsor
School Information
Elementary School: Oliver EllsworthJr High / Middle School: Sage ParkHigh School: Windsor

Building

Building Area
Building Area: 1920 Square Feet

Community

Community Features: Private School(s), Shopping/Mall

HOA

No HOA

Lot Information

Lot Area: 0.70 acres

Energy

Energy Efficiency Features: Thermostat, Windows

Miscellaneous

BasementMls Number: 24014618Attic: Access Via HatchAbove Grade Unfinished Area: 1920

Additional Information

Private School(s)Shopping/Mall
Last check for updates: about 4 hours ago
Listed by Mary Beth Welsh, (860) 249-1798
Century 21 AllPoints Realty, (860) 521-0021
Bought with: Barbara Clerice, (860) 833-0820, Elite Legacy Realty LLC, (860) 833-0820
Source: Smart MLS, MLS#24014618

Price History for 27 Kennedy Road

DatePriceEventSource
06/18/2024$449,500Sold
Smart MLS #24014618
06/03/2024$434,700PendingSmart MLS #24014618
05/10/2024$434,700Listed For SaleSmart MLS #24014618
05/31/2019$273,900Sold
Smart MLS #170168924
04/03/2019$274,900PendingAgent Provided
03/03/2019$274,900Listed For SaleAgent Provided

Market trends in Windsor

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$336K
$27.63KMoM
Sale-to-List Price
—
Price per sq ft
$214
$3MoM
Available listings
60
3MoM
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Property Tax and Assessment

Year2025
Tax$7,086
Assessment$249,060
Home facts updated by county records

Comparable Sales for 27 Kennedy Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
15 Kennedy Road, Windsor, CT
0.04
Single-Family Home
$430,000
07/10/26
3
2.5
1,764
428 Palisado Avenue, Windsor, CT
0.22
Single-Family Home
$450,000
07/01/26
3
2
2,246
36 Pilgrim Drive, Windsor, CT
0.52
Single-Family Home
$410,000
05/28/26
4
2
1,526
15 Pilgrim Drive, Windsor, CT
0.52
Single-Family Home
$310,000
09/22/25
4
2
1,981
39 Old Kennedy Road, Windsor, CT
0.19
Single-Family Home
$246,000
04/30/26
3
1.5
1,168
55 Foster Lane, Windsor, CT
0.29
Single-Family Home
$325,000
01/16/26
2
1.5
1,836
37 Pilgrim Drive, Windsor, CT
0.56
Single-Family Home
$335,000
06/11/26
4
2
1,886

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Kennedy Road.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
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  • 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
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  • Sarah L.
    "Poquonock school is a wonderful community all the parks are very safe and the parks & rec programs are great"
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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 "
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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
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  • 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
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  • Lisanickersondouglas
    "Great schools / diverse community. Easy highway access. Lots of parks and trails for walking. Many annual events for kids and families. "
    0
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  • 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
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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.