445 Main St, Middlefield, CT 06455
OFF MARKET

445 Main St
Middlefield, CT 06455

  • 3 Beds
  • 3 Baths
  • 1,959 sqft (on 1.42 acres)

$494,400

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $3,324/mo*
Refinance Your Home

$494,400

Trulia Estimate
as of Jun 2, 2026
Est. Refi. Payment $3,324/mo*
Refinance Your Home
3 Beds
3 Baths
1,959 sqft
(on 1.42 acres)

Local Information

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

Description

The Henry W. Skinner House is a Greek Revival style home built in 1860. Its façade features floor to ceiling windows on the first floor, evidence that supports a local tradition that this structure housed a store in the 19th century. The house displays typical Greek Revival features including a fully pedimented triangular gable with a four pane rectangular window. The open one story porch which spans the front is enclosed as it wraps around the east side of the house. This stately home is the essence of a time gone by yet with updated amenities. It includes three bedrooms on the upper level along with two full baths. The main level has a formal living and dining areas along with a kitchen and den/office and full bath. This home is set back from the road in a beautiful setting on 1.42 well maintained and manicured acres. There is plenty of open space/yard for all your outdoor entertaining needs. It includes a 40x20 in ground pool with an attached screen-in cabana complete with a changing room and space to entertain. Attached to the cabana is a two car garage and oversized shed. Take the time to view this lovely 19th century gem. Make an appointment today for your private showing.
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
No Info
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 445 Main St

Interior Features

Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
AtticNumber of Rooms: 7

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood

Property Information

Year Built
Year Built: 1860
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.42 acres

Price History for 445 Main St

DatePriceEventSource
10/14/2016$271,000Sold
Smart MLS #P10162123
09/08/2016$284,900PendingAgent Provided
08/22/2016$284,900Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$6,565
Assessment$220,300
Home facts updated by county records

Comparable Sales for 445 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
20 Mack Road, Middlefield, CT
0.31
Single-Family Home
$415,000
09/30/25
4
3.5
2,776
17 Esther Drive, Middlefield, CT
0.41
Single-Family Home
$465,528
04/30/26
3
2.5
2,152
30 Dwight Road, Middlefield, CT
0.44
Single-Family Home
$409,500
09/03/25
3
1.5
1,960
38 High Street, Middlefield, CT
0.64
Single-Family Home
$375,000
07/25/25
3
2
2,576
45 Dwight Road, Middlefield, CT
0.47
Single-Family Home
$475,000
04/27/26
3
1.5
1,554
32 Powder Hill Road, Middlefield, CT
0.75
Single-Family Home
$550,000
08/28/25
3
2.5
2,812
5 Race Track Hollow, Middlefield, CT
0.58
Single-Family Home
$705,000
04/24/26
4
3.5
2,806
35 Kickapoo Rd, Middlefield, CT
0.07
Single-Family Home
$240,000
09/02/25
2
1
608
130 Cherry Hill Road, Middlefield, CT
0.86
Single-Family Home
$357,500
07/25/25
3
1.5
1,142
11 Pond Meadow Place, Middlefield, CT
0.87
Single-Family Home
$711,000
11/07/25
4
3.5
3,363

Nearby homes

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Assigned Schools

These are the assigned schools for 445 Main St.
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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
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  • 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. "
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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
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  • 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 445 Main St

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Off Market Homes Near 445 Main St

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Homes for rent near 445 Main St

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445 Main St, Middlefield, CT 06455 is a 3 bedroom, 3 bathroom, 1,959 sqft single-family home built in 1860. This property is not currently available for sale. 445 Main St was last sold on Oct 14, 2016 for $271,000. The current Trulia Estimate for 445 Main St is $494,400.