442 Cherry Hill Rd, Middlefield, CT 06455
Property image
Property image
OFF MARKET

442 Cherry Hill Rd
Middlefield, CT 06455

  • 3 Beds
  • 2 Baths
  • 1,693 sqft (on 5 acres)

$544,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $3,665/mo*
Refinance Your Home

$544,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $3,665/mo*
Refinance Your Home
3 Beds
2 Baths
1,693 sqft
(on 5 acres)

Local Information

  • Map ViewExplore the area around 442 Cherry Hill Rd.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

5 Private Beautiful Level Acs with huge barn perfect for horses or livestock. Updated kitchen, both bathrooms, open concept living room; new septic. Natural brook runs through the back of the property. Bordered by town open space on the left
442 Cherry Hill Rd, Middlefield, CT 06455 is a 3 bedroom, 2 bathroom, 1,693 sqft single-family home built in 1957. It last sold for $270,000 on Aug 26, 2009. It is currently off market. The Trulia Estimate is $544,600, with a rent estimate of $3,214/month.

Home Highlights

Parking
Garage
Outdoor
Deck, Pool
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 442 Cherry Hill Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6Types of Rooms: Dining Room, Family RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, Other, Stove, Oil, Wood PelletHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylGardenLawn
Pool
Pool
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1957
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 5.00 acres

Price History for 442 Cherry Hill Rd

DatePriceEventSource
08/26/2009$270,000Sold
Smart MLS #G528093
05/14/2009$299,900Listed For SaleAgent Provided

Market trends in Middlefield

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
5
1MoM
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Property Tax and Assessment

Year2025
Tax$7,328
Assessment$245,900
Home facts updated by county records

Comparable Sales for 442 Cherry Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
48 Industrial Park Access Rd, Middlefield, CT
0.14
Single-Family Home
$530,000
04/16/26
3
2
1,698
41 Day School Drive, Middlefield, CT
0.51
Single-Family Home
$645,000
01/12/26
3
2.5
2,949
45 Snell Road, Middlefield, CT
0.47
Single-Family Home
$900,000
09/10/25
4
3.5
4,458
123 Round Hill Road, Middletown, CT
1.38
Single-Family Home
$600,000
06/26/26
3
2
2,064
11 Pond Meadow Place, Middlefield, CT
0.68
Single-Family Home
$711,000
11/07/25
4
3.5
3,363
107 Main St, Middlefield, CT
1.00
Single-Family Home
$382,500
06/01/26
3
2
1,200
68 Brittany Drive, Durham, CT
1.18
Single-Family Home
$658,000
05/28/26
3
3
3,108
385 Main Street, Durham, CT
1.00
Single-Family Home
$290,000
06/16/26
2
1.5
948
2332 South Main Street, Middletown, CT
0.83
Single-Family Home
$217,500
11/21/25
3
1
758
43 Woodland Drive, Durham, CT
1.08
Single-Family Home
$315,000
09/19/25
4
1
1,529

Nearby homes

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Assigned Schools

These are the assigned schools for 442 Cherry Hill Rd.
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 Middlefield

At least 15 Trulia users voted on each feature.

  • 100 % Say there's holiday spirit

  • 100 % Say car is needed

  • 93 % Say yards are well-kept

  • 90 % Say it's dog friendly

  • 84 % Say parking is easy

  • 83 % Say people would walk alone at night

  • 81 % Say there's wildlife

  • 76 % Say kids play outside

  • 75 % Say it's quiet

  • 63 % Say neighbors are friendly

  • 58 % Say they plan to stay for at least 5 years

  • 50 % Say there are community events

  • 39 % Say it's walkable to restaurants

  • 19 % Say streets are well-lit

  • 12 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Christina
    "Great area to walk dogs and meet other dogs. We have a dog park as well and lots of walking and hiking trails "
    0
    Flag
  • Kelican8621
    "Lived here for 7-8 years. Elementary through high school years actually. Great place to grow up and raise a family. The park in the center of town is well maintained and continually is adding additional activities for the community "
    1
    Flag
  • Mazie123b
    "Middlefield is a great town. Everyone is very friendly and neighborly and it is overall a safe place to live. "
    1
    Flag
  • Beannbeann
    "Great neighborhood. Every one is friendly. Nice area to take walks. No car traffic. And only a few miles from shopping. "
    1
    Flag
  • Beannbeann
    "Great area to walk your dog around and there’s a dog park within two miles from this area by the lake"
    0
    Flag
  • Beannbeann
    "Great small town to raise children. Close to shopping and highways but far enough away that you feel your living in the country. "
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  • Beannbeann
    "I’ve lived in this neighborhood for 18 years now and it’s great. Friendly neighbors. Houses are close enough to walk from house to house but most properties are at least a half acre or more. Great area for kids to grow up in. "
    0
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  • Mazie B.
    "People are constantly walking their dogs around the neighborhood. There are no sidewalks, but there are plenty of nice, quiet, open streets. "
    0
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  • Debi W.
    "Lived here almost all my life - love small-town living! You can always count on your neighbors to be there for you. Quiet and tranquil - but close to big cities!"
    3
    Flag
  • Lisareed2018
    "My family has lived in this town for more than 100 years. I love this little town. Good schools, great homeownership ratio, nice homes with good sized yards, skiing, recreation, nestled in the country, but close enough to cities, too! "
    0
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Apartments for Rent

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Homes for sale near 442 Cherry Hill Rd

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Off Market Homes Near 442 Cherry Hill Rd

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