20 Bear Path Ct, Cheshire, CT 06410
Property image
Property image
OFF MARKET

20 Bear Path Ct
Cheshire, CT 06410

  • 4 Beds
  • 3 Baths
  • 2,134 sqft (on 0.47 acres)

$544,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $3,828/mo*
Refinance Your Home

$544,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $3,828/mo*
Refinance Your Home
4 Beds
3 Baths
2,134 sqft
(on 0.47 acres)

Home Value

Trulia Estimate
$545K
Since last month
Decreased$5K (-0.9%)
Since last year
Increased$13K (+2.4%)
Since last sale
Increased$192K (+54.1%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$547K
July 2026$552K
June 2026$555K
May 2026$545K
April 2026$537K
March 2026$523K
February 2026$509K
January 2026$522K
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
54 Hemlock Ridge, Cheshire, CT
0.06
Single-Family Home
$451,000
08/17/26
3
1.5
1,673
745 Rustic Lane, Cheshire, CT
0.24
Single-Family Home
$530,000
11/06/25
4
2.5
1,854
634 Cornwall Avenue, Cheshire, CT
0.30
Single-Family Home
$446,000
01/06/26
4
3
1,456
751 Rustic Lane, Cheshire, CT
0.24
Single-Family Home
$610,000
10/17/25
4
2.5
1,854
258 Argyle Road, Cheshire, CT
0.27
Single-Family Home
$515,000
12/01/25
3
2.5
2,322
791 Ives Row, Cheshire, CT
0.41
Single-Family Home
$520,000
11/12/25
4
3
2,236
754 Rustic Lane, Cheshire, CT
0.20
Single-Family Home
$651,000
07/31/26
3
2.5
2,410
48 Willow Street, Cheshire, CT
0.35
Single-Family Home
$647,250
12/30/25
4
2.5
2,494
288 Argyle Road, Cheshire, CT
0.25
Single-Family Home
$686,000
10/31/25
4
2.5
2,566
772 Rustic Ln, Cheshire, CT
0.20
Single-Family Home
$330,000
09/17/25
3
2
1,536

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
54 Hemlock Ridge, Cheshire, CT 06410
0.06
$451,000
3
1.5
1,673
Recently Sold
60 Holly Road, Cheshire, CT 06410
0.14
$496,200
3
1.5
2,798
Off Market
50 Ives Hill Court #50, Cheshire, CT 06410
0.17
$355,100
3
2.5
1,486
Off Market
30 Frances Court, Cheshire, CT 06410
0.16
$718,700
4
3
2,972
Off Market
37 Ives Hill Court #37, Cheshire, CT 06410
0.19
$299,950
2
2.5
1,686
Recently Sold
267 Oak Avenue, Cheshire, CT 06410
0.19
$534,800
3
2
2,624
Off Market
272 Oak Avenue, Cheshire, CT 06410
0.20
$523,800
3
2
1,621
Off Market
754 Rustic Lane, Cheshire, CT 06410
0.20
$651,000
3
2.5
2,410
Recently Sold
25 Ives Hill Court #25, Cheshire, CT 06410
0.25
$343,300
3
2.5
1,486
Off Market
745 Rustic Lane, Cheshire, CT 06410
0.24
$530,000
4
2.5
1,854
Recently Sold
751 Rustic Lane, Cheshire, CT 06410
0.24
$629,500
4
2.5
1,854
Off Market
288 Argyle Road, Cheshire, CT 06410
0.25
$686,000
4
2.5
2,566
Recently Sold

Local Information

  • Map ViewExplore the area around 20 Bear Path Ct.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1977
Lot Size
0.47 acres
Living Area
2,134 sqft
Price/Sqft
$255
Parking
Garage

About this House

Four bedroom colonial, perfectly situated on a small cul-de-sac in a wonderful neighborhood!Kitchen w/ corian countertops opens into family room onto deck and lower deck w/ hottub!Extra finished area in basement for office/2nd family room. Roof, windows, siding all new w/in the past few years. Truly enjoyed by the sellers, this home is ready for the next owners. Located in a popular neighborhood, close to schools, linear park, and plenty of activity. Affordable electric heat w/ propane water heater and stove top, including a pellet stove, make this an advantage in fuel costs! Perennial plantings in and around the yard will be prevalent in the coming months. Come see this home soon! Owners would prefer a June closing.
20 Bear Path Ct, Cheshire, CT 06410 is a 4 bedroom, 3 bathroom, 2,134 sqft single-family home built in 1977. It last sold for $355,000 on Jul 7, 2008. It is currently off market. The Trulia Estimate is $544,700, with a rent estimate of $3,860/month.

Home Details for 20 Bear Path Ct

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Baseboard, GasHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1977Year Updated: 1993
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.47 acres

Price and Tax history

DateEventPrice
Jul 7, 2008
Source: Smart MLS #N274699
Sold
$355,000
Aug 8, 1991
Source: N/A
Sold
$200,000

Market trends in Cheshire

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$522K
$55KMoM
Sale-to-List Price
102.5%
1.2%MoM
Price per sq ft
$266
$5MoM
Available listings
58
3MoM

Around this home

What Locals Say about Cheshire

At least 102 Trulia users voted on each feature.

  • 95 % Say car is needed

  • 94 % Say parking is easy

  • 85 % Say yards are well-kept

  • 85 % Say it's dog friendly

  • 84 % Say there's wildlife

  • 81 % Say there's holiday spirit

  • 77 % Say it's quiet

  • 73 % Say people would walk alone at night

  • 68 % Say they plan to stay for at least 5 years

  • 68 % Say kids play outside

  • 62 % Say neighbors are friendly

  • 58 % Say there are sidewalks

  • 58 % Say streets are well-lit

  • 41 % Say it's walkable to restaurants

  • 37 % Say there are community events

  • 35 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Beautiful respectful peaceful people and neighborhood grate community. Clean and organized and has such a great atmosphere and very family orientated "
    0
    Flag
  • Joshua Wendell
    "It’s easy to get to the highway. Though in some parts of town it can take time to get through and make your way towards where you’re going. "
    0
    Flag
  • Reneechoquette
    "Great for trick of treating, close to the rail trail for biking, walking, running, or walking the dog! "
    1
    Flag
  • Ctbondlynx
    "Yes dog friendly. Dog parks are near by. And plentiful. Many dogs in the Cheshire neighborhoods. Dogs"
    0
    Flag
  • Reneechoquette
    "Safe, quiet, friendly, and lots of kids in this neighborhood (great for trick or treating!) Thr elementary school and rail trail (for waking and biking) are all in walking distance. "
    0
    Flag
  • Hollie.barclay
    "Amazing school district and great for kids growing up. We drive a vehicle for all our needs and only use a bike for rec purposes. We have walked on a few occasions but not often. "
    1
    Flag
  • Reneechoquette
    "My commute is into Hartford and there is public transportation into the city. The drive otherwise is about 45 min. "
    0
    Flag
  • Taylor D.
    "Lights of hope, relay for life, town sports and community outreach programs. Fairs and festivals in the fall with small business promotion"
    0
    Flag
  • Russell P.
    "about half an hour, I don't work in town. traffic can get pretty bad going south on the highway. back roads offer a good alternative, drivers I. the area tend to be slow though. "
    0
    Flag
  • Sheena N.
    "Cheshire is a nice quiet town. Not too much to do, not many restaurants or shopping centers, but close enough to everything where you don’t really mind. "
    0
    Flag
  • Janemarques08
    "That there are plenty of walking trails and sufficient sidewalks to safely walk your dog, whether it’s early morning or late at night. Totally safe neighborhood. "
    2
    Flag
  • Sheena N.
    "Close to 84 and 691. Not too far from Merritt or 91. Route 10 can be congested at times, but mostly everything is easy to get to"
    0
    Flag
  • Stephanie B. P.
    "Dogs are usually seen walking on leashes. Most are friendly and owners greet each other allowing them to engage. "
    1
    Flag
  • Mary
    "On my neighborhood street almost everyone has well behaved dogs. The neighbors clean up after their dogs. The street is perfect walking dogs- less traffic and extra wide roads. "
    0
    Flag
  • Janemarques08
    "I’ve lived her for two years. I know most of my neighbors. I feel good knowing that my children attend top “A”rated schools and that we live in a safe neighborhood. "
    5
    Flag
  • Nelson_sheena
    "The school system in Cheshire is great. They have tons of fun family activities. The community seems safe as well. Kids ride bikes on the trails and always people are walking their dogs. "
    1
    Flag
  • Nelson_sheena
    "Route 10 can be a little crowded during rush hour, but its not bad. The roads are clear and cleaned. "
    0
    Flag
  • Sjhickok01
    "great safe place, lots of kids, lots of great wildlife. most people walk their dogs 2-3 times a day...almost everyone is friendly. Beautiful area due to all of the different trees and plants. Beautiful holiday lights and halloween is always a favorite. lots of festivals during the spring/summer season."
    0
    Flag
  • janemarques08
    "We have movie night with popcorn near my neighborhood. Lots of group support and activities for the children. "
    1
    Flag
  • Jcasner
    "Safe great schools, best fire department and good police department. Great parks overall one of the best towns in CT. "
    1
    Flag
  • Alyss L.
    "Lots of families with kids and a closed loop street. I also grew up here (1985+) and the town has barely changed. Love that I can raise my kids here now."
    2
    Flag
  • Sara c.
    "My neighborhood is amazing! It is very quiet and and neighbors are friendly. We have easy access to all major highways."
    1
    Flag
  • Nelson_sheena
    "Dogs are always walking all around the neighborhood. Dog friendly for sure. I see more pits and retrievers than any other dog breed"
    1
    Flag
  • Dorothy R.
    "I am retired so I don't have a commute. Family member does and has described it as usually uneventful."
    0
    Flag
  • Emily M. G.
    "Great neighborhood in a great town, I feel safe. I’ve lived and grew up here for 23 years and I would live in cheshire as an adult"
    2
    Flag
  • Nelson_sheena
    "Quiet, farm land, lots to do. Good restaurants and lots to do with the kids. Lots of shops, banks, pretty scenery"
    0
    Flag
  • Emily M. G.
    "It’s a small, nice, and safe neighborhood. I’ve lived in the same house my whole life. It’s right next to mixville, I love walking around my neighborhood, everyone’s very nice."
    0
    Flag
  • Nelson_sheena
    "Cheshire is a quiet well kept town. The condos I live in are quiet and everyone is respectful. Lots of wildlife too"
    0
    Flag
  • adsinsight
    "Live near by, wish I lived here! Great place to raise a family and enjoy life's simple pleasures. Community is very close.. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 20 Bear Path Ct

  • What is 20 Bear Path Ct estimated to be worth?
    Trulia's estimated value for 20 Bear Path Ct in Cheshire, CT is $544,700.
  • What is the price history for 20 Bear Path Ct?
    20 Bear Path Ct in Cheshire, CT last sold for $355,000 in July 2008.
  • Is Cheshire a buyer's or seller's market?
    Cheshire is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Cheshire?
    The median sale price in Cheshire is $522K. That is up $55K from the prior month.
  • How big is the lot at 20 Bear Path Ct?
    The lot at 20 Bear Path Ct in Cheshire, CT is about 0.47 acres (20,473 sq ft).
  • Does 20 Bear Path Ct have a garage?
    Yes, 20 Bear Path Ct in Cheshire, CT has a garage.

Explore by feature - Pet Friendly

9 pet-friendly rentals in Cheshire, CT

Explore by feature - Garage

6 rentals with a garage in Cheshire, CT

Explore by feature - Air Conditioning

14 rentals with air conditioning in Cheshire, CT

Explore by feature - Washer/dryer

16 rentals with a washer/dryer in Cheshire, CT

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