255 Second Hill Rd, Bridgewater, CT 06752
OFF MARKET

255 Second Hill Rd
Bridgewater, CT 06752

  • 3 Beds
  • 2 Baths
  • 1,773 sqft (on 9.48 acres)

$740,800

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $4,869/mo*
Refinance Your Home

$740,800

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $4,869/mo*
Refinance Your Home
3 Beds
2 Baths
1,773 sqft
(on 9.48 acres)

Local Information

Map showing home location
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Description

This single-family home is located at 255 Second Hill Rd, Bridgewater, CT. 255 Second Hill Rd is in Bridgewater, CT and in ZIP code 06752. This property has 3 bedrooms, 2 bathrooms and approximately 1,773 sqft of floor space. This property has a lot size of 9.48 acres and was built in 2000.
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
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 255 Second Hill Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 9.48 acres

Price History for 255 Second Hill Rd

DatePriceEventSource
03/02/2001$120,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$8,038
Assessment$423,030
Home facts updated by county records

Comparable Sales for 255 Second Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5 Monroe Drive, New Milford, CT
0.23
Single-Family Home
$480,000
01/16/26
3
2.5
1,854
7 Jefferson Drive, New Milford, CT
0.27
Single-Family Home
$485,000
02/20/26
4
1.5
1,662
6 Revere Road, New Milford, CT
0.13
Single-Family Home
$455,000
08/27/25
4
2.5
1,456
8 Revere Road, New Milford, CT
0.13
Single-Family Home
$560,000
12/03/25
4
3
2,379
12 Jefferson Drive, New Milford, CT
0.38
Single-Family Home
$545,000
06/23/25
3
2.5
2,168
9 Monroe Drive, New Milford, CT
0.28
Single-Family Home
$530,000
08/19/25
4
2.5
2,376
79 Ben Whitney Lane, Bridgewater, CT
0.89
Single-Family Home
$710,000
10/31/25
3
2
3,136
5 Richconn Drive, New Milford, CT
0.34
Single-Family Home
$550,000
06/25/25
4
2.5
2,152
8 Winston Way, New Milford, CT
0.28
Single-Family Home
$650,000
09/04/25
4
2.5
3,048
8 Standish Road, New Milford, CT
0.33
Single-Family Home
$595,000
06/02/25
4
2.5
2,627

Nearby homes

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Assigned Schools

These are the assigned schools for 255 Second 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 New Milford

At least 189 Trulia users voted on each feature.

  • 88 % Say car is needed

  • 85 % Say parking is easy

  • 78 % Say yards are well-kept

  • 74 % Say it's dog friendly

  • 73 % Say there's holiday spirit

  • 72 % Say there's wildlife

  • 67 % Say it's quiet

  • 66 % Say people would walk alone at night

  • 56 % Say kids play outside

  • 55 % Say neighbors are friendly

  • 52 % Say they plan to stay for at least 5 years

  • 36 % Say it's walkable to restaurants

  • 35 % Say streets are well-lit

  • 30 % Say there are community events

  • 26 % Say there are sidewalks

  • 24 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Alexandra
    "Love it here. Friendly safe, small town feel with privacy. Farmers market and local farm stands as well as creameries and other small businesses make it feel like a special place to live. "
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  • Bernice.guerra
    "It is an amazing Comunity! People is very social, schools are very accessible and teacher very professionals, new Milford it is a Comunity very safe! "
    0
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  • Lanabsn
    "I’ve lived in this neighborhood for about ten years and not only do I find it gorgeous, I also find that it’s friendly, safe and welcoming. I came from a beach community in California where the ocean was my front yard. I never, for even a moment, would have believed that a small town on the east coast would bring me so much happiness! From neighbors who live next door to the business owners you see every week, I’ve gotten to know them all and I can honestly say I’ve never felt more comfortable and happy in any other place I’ve lived. And yes, I’ve lived in many other cities and states!"
    0
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  • Luis Rojas
    "I have been living in this neighborhood for almost 3 years. Lost of space and privacy to grow your family in a safer area. "
    0
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  • Luis Rojas
    "Very nice town and quiet. Not a lot to do around, but it’s very nice to grow a family as you have space. Nice small businesses around. "
    0
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  • Meadlaura98
    "theres a dog park in this area and people enjoy others company when they visit it. plus its bog and kept very nice"
    0
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  • Meadlaura98
    "Very nice area easy to get around lots of people In area and easy access to where u need to go .. nice area"
    0
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  • Meadlaura98
    "Nice well outside maintained. lots of different landlords around…. Seems very friendly here!!! Can live in area nicely"
    0
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  • Trulia User
    "This is a great neighborhood for dogs, but there are wild animals (bears, fox, coyotes). There are no street lights or sidewalks."
    0
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  • Luis Rojas
    "It’s gorgeous and peaceful family oriented neighborhood. A lot of activities.farms,restaurants and amazing views close to Danbury where everything is."
    0
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  • Trulia User
    "It is a secluded neighborhood. Everyone is friendly and looks out for each other. It is close to every thing. A five minute drive "
    0
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  • Trulia User
    "Feels like a great community. I feel like I am apart of community events and everyone is included. People are super friendly "
    0
    Flag
  • Sam P.
    "Ive lived here for most of my life and have found the people to be generally nice. There’s a v quaint and pleasant vibe to the town. "
    0
    Flag
  • Darlene C.
    "Everything is right here. Walking distance and safe. A beautiful quaint little village . There are. Parks and restaurants and a bus line I take since I don’t have a car "
    5
    Flag
  • Nstat42
    "It is easy to get around and traffic is rarely an issue. The center of town can get hectic at times such as the PM rush hour and some early weekend afternoons"
    1
    Flag
  • Megrochford
    "Schools are good, town is cute, and people are friendly. For a large town it is common to run into people you know"
    1
    Flag
  • Richlbair
    "many families with dogs on the neighborhood. Very dog and pet friendly. light traffic for dog walking."
    3
    Flag
  • Mjbestpainting
    "I like the country side that’s why new Milford suit for me perfectly it’s quite and people are friendly "
    0
    Flag
  • Monique Sloane
    "every one is friendly in the neighborhood. it's like one big family thepeople are very neighborly and they are the type to share what they have with each other. the kis are wonderful too they play with each other and look out for one another."
    3
    Flag
  • Bjmag01
    "I’ve lived here on and off in this area of New Milford for 38 years and from the beginning it was a Happy carful neighborhood and over the years it has changed to disgusting of how people do not take care of their property, storing of stuff that is not suitable to be on the road,neighborhood has gone the drain, "
    0
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  • Pamela F
    "it's a great town but Willow Springs needs updating. The property is well maintained outside but needs updating inside. "
    0
    Flag
  • Lulusampa1
    "Events at the green. Nice restaurants. Lots of stores. Lots of hiking stops. Rocky rivers, trails, lakes for swimming and boating. Beautiful views, lots of mountains . Quick ride to anywhere. 25 minutes from the Danbury fair mall ."
    0
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  • Conor G.
    "Extremely walkable with plenty of natural space + wildlife. Good schools with NYC train just minutes away in Danbury/Brewster (NY). Southern New England at its best."
    0
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  • Aerlinnwen
    "New Milford has lots of community spirit! There are also a variety of activities and events that take place throughout the year."
    1
    Flag
  • Ellaraeismysunshine
    "Great community especially for family’s. Always something to do for the kids. Beautiful green and downtown area love this town!"
    1
    Flag
  • Rob.elings
    "Enough dog lovers. Enough space for dogs to play. Many dogs to meet....................................... "
    0
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  • Dominica S.
    "New Milford is a great town. You can have a city setting or a country setting. The high school is too large with way too many kids. It’s hard for kids to fit in... I love the sports. They have a great football team wether it be for the h.s. Or pop warner. "
    2
    Flag
  • Cbknyc
    "Historical society. Merwinsville Hotel. 1 room school house. Browns forge. Husettaniv river. Streams. "
    0
    Flag
  • Jhendrix03
    "Village Fair Days, farmers market, 4th of July fireworks, Memorial Day parade, Summer Thursday’s, movies on the green"
    1
    Flag
  • Forel B.
    "many people walk their dogs in the neighborhood as there is not much vehicle traffic and plenty of open land to run your dog"
    0
    Flag
  • Wisdomsherry
    "Great quite family neighborhood. Route 7 and High School close by.Wonderful area to run walk. Borders the town of Brookfield. "
    0
    Flag
  • Susan F.
    "I love this town. It reminds me of some of the towns in Vermont. It is big area wise and it is a late booming town. "
    0
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255 Second Hill Rd, Bridgewater, CT 06752 is a 3 bedroom, 2 bathroom, 1,773 sqft single-family home built in 2000. This property is not currently available for sale. 255 Second Hill Rd was last sold on Mar 2, 2001 for $120,000. The current Trulia Estimate for 255 Second Hill Rd is $740,800.