369 Jackson Hill Rd, Middlefield, CT 06455
OFF MARKET

369 Jackson Hill Rd
Middlefield, CT 06455

  • 4 Beds
  • 3 Baths
  • 2,271 sqft (on 0.36 acres)

$462,300

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $3,113/mo*
Refinance Your Home

$462,300

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $3,113/mo*
Refinance Your Home
4 Beds
3 Baths
2,271 sqft
(on 0.36 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Beautifully situated on a large lot with oversized 2-car garage, this property has newer windows and siding, new A/C condensers, new furnace and hot water heater, and new septic system (tank & leach fields). Inside you will find gleaming hardwoods, a versatile floorplan, enormous master suite with separate sitting room/study, optional first floor master/guest suite, three full modern stone baths, family room, office, and sophisticated kitchen with stainless steel appliances. The solar panels are a fantastic money saver as well! Minutes from Lyman Orchards, Lyman Golf Course, Powder Ridge, Wesleyan, and Wadsworth Falls, this property is everything you could ask for. Motivated seller!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 369 Jackson Hill Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Interior Details
Number of Rooms: 9
Appliances & Utilities
DishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.36 acres

Price History for 369 Jackson Hill Rd

DatePriceEventSource
05/30/2019$285,000Sold
Smart MLS #170116542
05/24/2019$299,900PendingAgent Provided
11/29/2018$299,900PendingToActiveAgent Provided
11/21/2018$299,900PendingAgent Provided
11/09/2018$299,900PriceChange
Agent Provided
09/26/2018$324,900PriceChange
Agent Provided
08/28/2018$339,900PriceChange
Agent Provided
08/17/2018$349,900Listed For SaleAgent Provided
03/14/2018$175,626Sold
N/A
10/31/2017$199,900PriceChange
Agent Provided
08/23/2017$219,900Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$5,984
Assessment$200,800
Home facts updated by county records

Comparable Sales for 369 Jackson Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20 Mack Road, Middlefield, CT
0.07
Single-Family Home
$415,000
09/30/25
4
3.5
2,776
30 Dwight Road, Middlefield, CT
0.39
Single-Family Home
$409,500
09/03/25
3
1.5
1,960
17 Esther Drive, Middlefield, CT
0.36
Single-Family Home
$465,528
04/30/26
3
2.5
2,152
45 Dwight Road, Middlefield, CT
0.47
Single-Family Home
$475,000
04/27/26
3
1.5
1,554
53 Maryland Dr, Middlefield, CT
0.82
Single-Family Home
$437,150
02/05/26
4
3
2,231
25 Aresco Drive, Rockfall, CT
0.77
Single-Family Home
$440,000
09/26/25
3
2
1,843
4 Aresco Drive, Rockfall, CT
0.76
Single-Family Home
$340,000
06/20/25
2
1
1,468
18 Rosemary Court, Middlefield, CT
0.93
Single-Family Home
$365,000
10/31/25
3
1
2,330
35 Kickapoo Rd, Middlefield, CT
0.27
Single-Family Home
$240,000
09/02/25
2
1
608
38 High Street, Middlefield, CT
0.71
Single-Family Home
$375,000
07/25/25
3
2
2,576

Nearby homes

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Assigned Schools

These are the assigned schools for 369 Jackson 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. "
    0
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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. "
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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 369 Jackson Hill Rd

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Off Market Homes Near 369 Jackson Hill Rd

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Homes for rent near 369 Jackson Hill Rd

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369 Jackson Hill Rd, Middlefield, CT 06455 is a 4 bedroom, 3 bathroom, 2,271 sqft single-family home built in 1940. This property is not currently available for sale. 369 Jackson Hill Rd was last sold on May 30, 2019 for $285,000. The current Trulia Estimate for 369 Jackson Hill Rd is $462,300.