259 Second Hill Rd, Bridgewater, CT 06752
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Property image
OFF MARKET

259 Second Hill Rd
Bridgewater, CT 06752

  • 4 Beds
  • 5 Baths
  • 4,512 sqft (on 5.99 acres)

$1,335,500

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $8,746/mo*
Refinance Your Home

$1,335,500

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $8,746/mo*
Refinance Your Home
4 Beds
5 Baths
4,512 sqft
(on 5.99 acres)

Local Information

  • Map ViewExplore the area around 259 Second Hill Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Beautiful modern Litchfield County home outfitted with top of the line finishes on a quiet street yet convenient to everything. Modern kitchen open to eating area and living room perfect for entertaining or relaxing. Viking & Miele SS appliances. Gas fp in LR, with sliders to the glass enclosed deck which sits above the beautiful rolling back yard and the pool. In addition to the MBR suite there are three bedrooms served by two full bathrooms on the second floor. The lower level great room is finished with seating and an exercise area, with walkout access to the rear yard & hot tub. Located on six private acres.

Tenant pays for yard maintenance, snow plowing, all utilities, tenant's insurance, heat and trash service
259 Second Hill Rd, Bridgewater, CT 06752 is a 4 bedroom, 5 bathroom, 4,512 sqft single-family home built in 2000. It last sold for $1,000,000 on Jul 14, 2021. More recently, it was listed as a rental in March 2023 with an asking price of $6,000 per month. That rental listing was removed on March 31, 2023. It is currently off market. The Trulia Estimate is $1,335,500, with a rent estimate of $6,923/month.

Home Highlights

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

Home Details for 259 Second Hill Rd

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, Workshop, Solarium Atrium, Sun RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: Asphalt, Other, Shake ShingleDeckExterior: Stone, WoodLawnPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 1

Lot Information

Lot Area: 5.99 acres

Price History for 259 Second Hill Rd

DatePriceEventSource
03/31/2023ListingRemovedZillow Rentals
03/16/2023$6,000Listed For RentZillow Rentals
07/14/2021$1,000,000Sold
Smart MLS #170343128
04/07/2021ListingRemovedWilliam Pitt and Julia B. Fee Sotheby's International Realty
11/12/2020$1,174,000PriceChange
Agent Provided
10/07/2020$1,199,000Listed For SaleAgent Provided
10/17/2006$1,050,000Sold
N/A
04/08/2002$550,000Sold
N/A

Market trends in New Milford

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$445K
$13.33KMoM
Sale-to-List Price
99.2%
Price per sq ft
$261
$11MoM
Available listings
107
1MoM
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Property Tax and Assessment

Year2025
Tax$12,977
Assessment$683,000
Home facts updated by county records

Comparable Sales for 259 Second Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2 Famja Lane, New Milford, CT
0.30
Single-Family Home
$625,000
09/08/25
4
3
3,373
18 Eastern Lane, New Milford, CT
0.48
Single-Family Home
$840,000
07/11/25
5
3.5
5,828
8 Winston Way, New Milford, CT
0.28
Single-Family Home
$650,000
09/04/25
4
2.5
3,048
8 Revere Road, New Milford, CT
0.13
Single-Family Home
$560,000
12/03/25
4
3
2,379
6 High Meadow Road, New Milford, CT
0.67
Single-Family Home
$650,000
10/24/25
5
3.5
5,676
25 Jefferson Drive, New Milford, CT
0.50
Single-Family Home
$665,000
10/21/25
5
4
4,797
9 Monroe Drive, New Milford, CT
0.28
Single-Family Home
$530,000
08/19/25
4
2.5
2,376
6 Revere Road, New Milford, CT
0.13
Single-Family Home
$455,000
08/27/25
4
2.5
1,456
63 Old Ridge Road, New Milford, CT
0.53
Single-Family Home
$425,000
04/30/26
4
3.5
2,842
14 Cambridge Circle, New Milford, CT
0.50
Single-Family Home
$490,000
01/30/26
4
2.5
2,603

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Assigned Schools

These are the assigned schools for 259 Second Hill Rd.
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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 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Ellaraeismysunshine
    "Great community especially for family’s. Always something to do for the kids. Beautiful green and downtown area love this town!"
    1
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  • 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
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  • Cbknyc
    "Historical society. Merwinsville Hotel. 1 room school house. Browns forge. Husettaniv river. Streams. "
    0
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  • Jhendrix03
    "Village Fair Days, farmers market, 4th of July fireworks, Memorial Day parade, Summer Thursday’s, movies on the green"
    1
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  • 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
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  • Wisdomsherry
    "Great quite family neighborhood. Route 7 and High School close by.Wonderful area to run walk. Borders the town of Brookfield. "
    0
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  • 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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13 rentals with air conditioning in Bridgewater, CT

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Homes for sale near 259 Second Hill Rd

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Off Market Homes Near 259 Second Hill Rd

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