33 Chamberlain Ct, Cheshire, CT 06410
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OFF MARKET

33 Chamberlain Ct
Cheshire, CT 06410

  • 5 Beds
  • 6 Baths
  • 6,660 sqft (on 5.03 acres)

$1,689,600

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $11,724/mo*
Refinance Your Home

$1,689,600

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $11,724/mo*
Refinance Your Home
5 Beds
6 Baths
6,660 sqft
(on 5.03 acres)

Home Value

Trulia Estimate
$1.69M
Since last month
Increased$4K (+0.2%)
Since last year
Increased$87K (+5.4%)
Since last sale
Increased$401K (+30.9%)
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 +86% in the last 10 years
MonthEstimated value
2026
August 2026$1.7M
July 2026$1.7M
June 2026$1.72M
May 2026$1.67M
April 2026$1.65M
March 2026$1.63M
February 2026$1.61M
January 2026$1.59M
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
40 Whispering Hollow Court, Cheshire, CT
0.52
Single-Family Home
$1,500,000
01/14/26
4
5
6,781
776 Bethany Mountain Road, Cheshire, CT
0.52
Single-Family Home
$947,500
04/29/26
4
2.5
3,300
50 Abrams Road, Cheshire, CT
0.51
Single-Family Home
$1,500,000
10/23/25
4
2.5
4,981
85 Inverness Court, Cheshire, CT
0.87
Single-Family Home
$850,000
06/26/26
5
3.5
3,919
15 Shire Court, Cheshire, CT
0.54
Single-Family Home
$1,125,000
07/02/26
4
2.5
4,437
25 Winding Trail, Cheshire, CT
0.42
Single-Family Home
$892,000
08/14/26
4
3
3,773
876 South Brooksvale Road, Cheshire, CT
0.26
Single-Family Home
$720,000
08/26/25
4
2.5
2,762
921 Bethany Mountain Road, Cheshire, CT
0.73
Single-Family Home
$820,000
08/17/26
5
3.5
3,455
440 Mount Sanford Road, Cheshire, CT
0.62
Single-Family Home
$710,000
01/08/26
4
4
3,816
25 Mountain Brook Drive, Cheshire, CT
0.56
Single-Family Home
$500,000
02/24/26
4
2.5
4,630

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
120 Rockview Drive, Cheshire, CT 06410
0.21
$474,500
3
1.5
1,496
Off Market
876 South Brooksvale Road, Cheshire, CT 06410
0.26
$745,100
4
2.5
2,762
Off Market
143 Rockview Drive, Cheshire, CT 06410
0.25
$444,200
3
1
1,416
Off Market
165 Rockview Drive, Cheshire, CT 06410
0.27
$465,200
3
1.5
1,334
Off Market
44 Roslyn Drive, Cheshire, CT 06410
0.29
$450,000
3
2
1,412
Recently Sold
31 Roslyn Drive, Cheshire, CT 06410
0.30
$517,300
3
2
1,556
Off Market
181 Crescent Circle, Cheshire, CT 06410
0.32
$501,000
3
1
1,601
Recently Sold
158 Crescent Circle, Cheshire, CT 06410
0.37
$424,000
3
1
1,236
Off Market
644 South Brooksvale Road, Cheshire, CT 06410
0.40
$1,662,500
4
4.5
6,361
For Sale
136 Crescent Circle, Cheshire, CT 06410
0.37
$465,200
3
1.5
1,706
Off Market
764 Bethany Mountain Road, Cheshire, CT 06410
0.39
$1,864,800
4
3.5
7,762
Off Market
32 Rockview Drive, Cheshire, CT 06410
0.39
$468,000
3
1
1,576
Off Market

Local Information

  • Map ViewExplore the area around 33 Chamberlain Ct.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2000
Lot Size
5.03 acres
Living Area
6,660 sqft
Price/Sqft
$254
Parking
Garage

About this House

Magnificent custom-built home with attention to every detail! So many incredible features! Drive down the pristine Cul-de-sac to the pillared driveway. The home is dramatically set back for privacy and the best use of the property. Meticulously maintained five acres. The foyer is stunning without being overwhelming and is also well utilized. The living spaces are spacious and well designed with the flow of a professionally designed home. Main level master suite with views of the unite pool, pool house, outdoor kitchen and covered outdoor entertainment area with stone fireplace and pizza oven. The second level features three spacious bedrooms with multiple dedicated bathrooms and the library. We are not donethe lower level has even more entertainment space with the state-of-the-art theater room, playroom & kitchen. Oversized three car garage. There is so much more to enjoyyou will love to call this home! Be sure to watch to video!
33 Chamberlain Ct, Cheshire, CT 06410 is a 5 bedroom, 5 bathroom, 6,660 sqft single-family home built in 2000. It last sold for $1,300,000 on Nov 16, 2021. It is currently off market. The Trulia Estimate is $1,689,600, with a rent estimate of $7,515/month.

Home Details for 33 Chamberlain Ct

Interior Features

Interior Details
BasementAtticNumber of Rooms: 13Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, Pantry, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: BrickGardenLawnPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2000Year Updated: 2021
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 5.03 acres

Additional Information

Intercom

Price and Tax history

DateEventPrice
Nov 16, 2021
Source: Smart MLS #170414739
Sold
$1,300,000
Oct 23, 2021
Source: Smart MLS #170414739
Contingent
$1,399,000
Aug 23, 2021
Source: RE/MAX International #170414739
Pending
$1,399,000
Jul 9, 2021
Source: Smart MLS #170414739
Listed For Sale
$1,399,000
Jun 30, 2008
Source: Smart MLS #N275106
Sold
$1,270,000

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
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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

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Explore by feature - Pet Friendly

9 pet-friendly rentals in Cheshire, CT

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Homes for sale near 33 Chamberlain Ct

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Off Market Homes Near 33 Chamberlain Ct

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Frequently asked questions about 33 Chamberlain Ct

  • What is 33 Chamberlain Ct estimated to be worth?
    Trulia's estimated value for 33 Chamberlain Ct in Cheshire, CT is $1,689,600.
  • What is the price history for 33 Chamberlain Ct?
    33 Chamberlain Ct in Cheshire, CT last sold for $1,300,000 in November 2021.
  • 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.
  • Does 33 Chamberlain Ct have air conditioning?
    Yes, 33 Chamberlain Ct in Cheshire, CT has air conditioning.
  • Does 33 Chamberlain Ct have a pool?
    Yes, 33 Chamberlain Ct in Cheshire, CT has a pool.