369 Jackson Hill Rd, Middlefield, CT 06455
Property image
Property image
OFF MARKET

$464,300

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

369 Jackson Hill Rd, Middlefield, CT 06455

Est. Refi. Payment $3,182/mo*
Refinance Your Home
Currently Off Market - Sold May 30, 2019 for $285,000

Home Value

Trulia Estimate
$464K
Since last month
Decreased$2K (-0.5%)
Since last year
Increased$21K (+4.8%)
Since last sale
Increased$179K (+62.7%)
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 +80% in the last 10 years
MonthEstimated value
2026
August 2026$464K
July 2026$466K
June 2026$470K
May 2026$464K
April 2026$453K
March 2026$449K
February 2026$427K
January 2026$427K
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
11 Burt Dr, Middlefield, CT
0.44
Single-Family Home
$248,000
07/30/26
4
2.5
1,900
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
341 Main Street, Rockfall, CT
0.30
Single-Family Home
$500,000
06/12/26
3
3
1,838
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
1,483
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

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
385 Jackson Hill Road, Middlefield, CT 06455
0.06
$416,200
3
2
1,337
Off Market
20 Mack Road, Middlefield, CT 06455
0.07
$537,500
4
3.5
2,776
Off Market
51 Mack Road, Middlefield, CT 06455
0.23
$472,300
4
2
1,946
Off Market
66 Burt Drive, Middlefield, CT 06455
0.24
$370,000
3
1
1,303
Off Market
341 Main Street, Rockfall, CT 06455
0.30
$500,000
3
3
1,838
Recently Sold
74 Burt Drive, Middlefield, CT 06455
0.29
$418,300
2
1
1,618
Off Market
31 Toad Ridge Road, Middlefield, CT 06455
0.31
$446,000
3
2.5
2,296
Off Market
10 Esther Drive, Middlefield, CT 06455
0.33
$493,000
3
2.5
2,793
Off Market
17 Esther Drive, Middlefield, CT 06455
0.36
$465,528
3
2.5
2,152
Recently Sold
17 Dwight Road, Middlefield, CT 06455
0.39
$419,000
3
1.5
1,604
Off Market
30 Dwight Road, Middlefield, CT 06455
0.39
$438,400
3
1.5
1,960
Off Market
76 Cider Mill Road, Rockfall, CT 06481
0.44
$651,200
5
3
3,742
Off Market

Local Information

  • Map ViewExplore the area around 369 Jackson Hill Rd.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1940
Lot Size
0.36 acres
Living Area
2,271 sqft
Price/Sqft
$204
Parking
Garage

About this House

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!
369 Jackson Hill Rd, Middlefield, CT 06455 is a 4 bedroom, 3 bathroom, 2,271 sqft single-family home built in 1940. It last sold for $285,000 on May 30, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $464,300, with a rent estimate of $3,465/month.

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 and Tax history

DateEventPrice
May 30, 2019
Source: Smart MLS #170116542
Sold
$285,000
May 24, 2019
Source: Agent Provided
Pending
$299,900
Nov 29, 2018
Source: Agent Provided
PendingToActive
$299,900
Nov 21, 2018
Source: Agent Provided
Pending
$299,900
Nov 9, 2018
Source: Agent Provided
PriceChange
$299,900
Price decreased by 8%

Market trends in Middlefield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
9
4MoM

Around this home

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 369 Jackson Hill Rd

  • What is 369 Jackson Hill Rd estimated to be worth?
    Trulia's estimated value for 369 Jackson Hill Rd in Middlefield, CT is $464,300.
  • What is the price history for 369 Jackson Hill Rd?
    369 Jackson Hill Rd in Middlefield, CT last sold for $285,000 in May 2019.
  • Is Middlefield a buyer's or seller's market?
    Middlefield is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Middlefield?
    Residents describe Middlefield, CT as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Middlefield, CT.
  • How big is the lot at 369 Jackson Hill Rd?
    The lot at 369 Jackson Hill Rd in Middlefield, CT is about 0.36 acres (15,682 sq ft).
  • Does 369 Jackson Hill Rd have a garage?
    Yes, 369 Jackson Hill Rd in Middlefield, CT has a garage.

Apartments for Rent

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Off Market Homes Near 369 Jackson Hill Rd

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