27 Jonathan Cir, Windsor, CT 06095
Property image
Property image
OFF MARKET

27 Jonathan Cir
Windsor, CT 06095

  • 4 Beds
  • 2.5 Baths
  • 1,794 sqft (on 0.46 acres)

$442,900

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $3,140/mo*
Refinance Your Home

$442,900

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $3,140/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,794 sqft
(on 0.46 acres)

Home Value

Trulia Estimate
$443K
Since last month
Increased$3K (+0.6%)
Since last year
Increased$9K (+2.1%)
Since last sale
Increased$94K (+26.9%)
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 +120% in the last 10 years
MonthEstimated value
2026
August 2026$444K
July 2026$441K
June 2026$449K
May 2026$451K
April 2026$440K
March 2026$434K
February 2026$416K
January 2026$416K
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
28 Sunnyfield Drive, Windsor, CT
0.15
Single-Family Home
$399,000
11/21/25
4
2
1,603
32 Sunnyfield Drive, Windsor, CT
0.14
Single-Family Home
$332,000
12/19/25
3
1.5
1,946
33 Nod Road, Windsor, CT
0.16
Single-Family Home
$370,000
10/17/25
3
2.5
1,664
107 Sunnyfield Drive, Windsor, CT
0.25
Single-Family Home
$337,000
12/09/25
3
2.5
1,352
60 Nod Road, Windsor, CT
0.16
Single-Family Home
$345,900
05/01/26
3
2
2,128
911 Matianuck Avenue, Windsor, CT
0.32
Single-Family Home
$310,000
09/02/25
3
2
1,684
41 Hale Drive, Windsor, CT
0.27
Single-Family Home
$368,500
12/15/25
3
1.5
1,558
819 Matianuck Avenue, Windsor, CT
0.38
Single-Family Home
$315,000
01/30/26
2
1.5
1,866
29 Quail Hollow Drive, Windsor, CT
0.47
Single-Family Home
$445,900
01/09/26
3
2
1,850
40 Gloria St, Windsor, CT
0.33
Single-Family Home
$262,500
12/18/25
3
2
1,202

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
82 Robin Road, Windsor, CT 06095
0.08
$502,900
4
2.5
2,372
Off Market
39 Sunnyfield Drive, Windsor, CT 06095
0.11
$473,500
3
1.5
2,284
Off Market
74 Robin Road, Windsor, CT 06095
0.08
$460,800
3
2.5
1,857
Off Market
21 Diana Lane, Windsor, CT 06095
0.09
$482,400
4
2.5
2,444
Off Market
62 Robin Road, Windsor, CT 06095
0.10
$415,100
3
2.5
1,566
Off Market
32 Sunnyfield Drive, Windsor, CT 06095
0.14
$332,000
3
1.5
1,946
Recently Sold
40 Sunnyfield Drive, Windsor, CT 06095
0.15
$413,800
4
2
1,846
Off Market
28 Sunnyfield Drive, Windsor, CT 06095
0.15
$399,000
4
2
1,603
Recently Sold
8 Penncross Drive, Windsor, CT 06095
0.16
$434,900
3
2.5
2,046
Off Market
56 Robin Road, Windsor, CT 06095
0.13
$446,600
3
2
1,465
Off Market
411 Park Avenue, Windsor, CT 06095
0.14
$337,500
2
1
1,123
Off Market
60 Nod Road, Windsor, CT 06095
0.16
$345,900
3
2
2,128
Recently Sold

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1959
Lot Size
0.46 acres
Living Area
1,794 sqft
Price/Sqft
$247

About this House

Location, Location, Location! This home has EVERYTHING! This beautiful 4 bedroom, 2.1 bath home has been lovingly maintained and restored, and it is just awaiting its new owner. There is so much space! Enter and find beautiful hardwood floors in the LR and DR going up to and through the bedrooms. There is a gorgeous statement wall surrounding the wood-burning fireplace in the sun drenched Formal Living Room. The Family Room has new carpeting and everything has been freshly painted. There are new vanities in the primary and half baths; there is a step-in shower in the primary suite and a tub in the hall bath. The bedrooms are large with good closet space. There are ample outlets in all the rooms, rare for a home of this age - and so useful! Connecticut in the Winter screams for warm wool clothes - store them in the CEDAR CLOSET in the basement! Need a home office? One is waiting for you down there as well! There is also space and lots of shelving to meet your storage needs. The attached 2 car garage opens into the family room. The gorgeous yard features mature fruit trees and lovely landscaping. There is space for a pool, playscape or fire pit - whatever you'd like to use to enjoy the outdoors! I hear that there was once a tree house here as well! This spectacular home has it all, including a PRIME location on a cul-de-sac in a quiet neighborhood.
27 Jonathan Cir, Windsor, CT 06095 is a 4 bedroom, 3 bathroom, 1,794 sqft single-family home built in 1959. It last sold for $350,000 on Oct 14, 2022. It is currently off market. The Trulia Estimate is $442,900, with a rent estimate of $3,241/month.

Home Details for 27 Jonathan Cir

Interior Features

Heating & Cooling
Heating: Baseboard, OilAir ConditioningHeating Fuel: Baseboard
Interior Details
Number of Rooms: 8
Appliances & Utilities
Washer
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Oct 14, 2022
Source: Smart MLS #170519680
Sold
$350,000
Sep 16, 2022
Source: Smart MLS #170519680
Contingent
$332,990
Sep 9, 2022
Source: Smart MLS #170519680
Listed For Sale
$332,990

Market trends in Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$343K
$7.33KMoM
Sale-to-List Price
102.7%
Price per sq ft
$211
$3MoM
Available listings
44
16MoM

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
    Flag
  • 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
    Flag
  • 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 "
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  • Amy C.
    "Windsor is a town with strong resources and traditions. It has reasonable housing prices and lots of diversity. "
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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."
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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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LGBTQ Local Legal Protections

Frequently asked questions about 27 Jonathan Cir

  • What is 27 Jonathan Cir estimated to be worth?
    Trulia's estimated value for 27 Jonathan Cir in Windsor, CT is $442,900.
  • What is the price history for 27 Jonathan Cir?
    27 Jonathan Cir in Windsor, CT last sold for $350,000 in October 2022.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Windsor?
    The median sale price in Windsor is $343K. That is up $7.33K from the prior month.
  • How big is the lot at 27 Jonathan Cir?
    The lot at 27 Jonathan Cir in Windsor, CT is about 0.46 acres (20,038 sq ft).
  • Does 27 Jonathan Cir have parking?
    Yes, 27 Jonathan Cir in Windsor, CT has on-site parking.

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