39 E Chestnut Hill Rd, Litchfield, CT 06759
OFF MARKET

39 E Chestnut Hill Rd
Litchfield, CT 06759

  • 4 Beds
  • 5 Baths
  • 6,253 sqft (on 10 acres)

$1,785,000

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $11,683/mo*
Refinance Your Home

$1,785,000

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $11,683/mo*
Refinance Your Home
4 Beds
5 Baths
6,253 sqft
(on 10 acres)

Local Information

  • Map ViewExplore the area around 39 E Chestnut Hill Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 39 E Chestnut Hill Rd, Litchfield, CT. 39 E Chestnut Hill Rd is in Litchfield, CT and in ZIP code 06759. This property has 4 bedrooms, 5 bathrooms and approximately 6,253 sqft of floor space. This property has a lot size of 10.00 acres and was built in 2009.
39 E Chestnut Hill Rd, Litchfield, CT 06759 is a 4 bedroom, 5 bathroom, 6,253 sqft single-family home built in 2009. It is currently off market. The Trulia Estimate is $1,785,000, with a rent estimate of $7,991/month.

Home Highlights

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

Home Details for 39 E Chestnut Hill Rd

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 2009
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 10.00 acres

Market trends in Litchfield

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
21
2MoM
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Property Tax and Assessment

Year2025
Tax$20,023
Assessment$1,001,170
Home facts updated by county records

Comparable Sales for 39 E Chestnut Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
93 Northfield Road, Litchfield, CT
0.19
Single-Family Home
$1,700,000
12/29/25
4
4
4,182
28 West Chestnut Hill Road, Litchfield, CT
0.66
Single-Family Home
$1,250,000
01/12/26
3
3.5
4,068
39 Fern Avenue, Litchfield, CT
0.88
Single-Family Home
$1,356,000
10/01/25
3
4
4,765
11 West Chestnut Hill Road, Litchfield, CT
0.79
Single-Family Home
$765,000
05/01/26
5
3.5
3,328
182 East Litchfield Road, Litchfield, CT
1.27
Single-Family Home
$775,000
12/03/25
4
3.5
3,327
137 Buell Road, Litchfield, CT
0.93
Single-Family Home
$760,000
08/29/25
3
2.5
2,600
180 South St, Litchfield, CT
1.25
Single-Family Home
$1,825,000
10/02/25
6
6.5
5,521
265 South St, Litchfield, CT
1.12
Single-Family Home
$308,000
05/11/26
3
3
3,336
44 South Street, Litchfield, CT
1.39
Single-Family Home
$2,188,000
04/15/26
5
5.5
5,448
148 Buell Rd, Litchfield, CT
0.86
Single-Family Home
$243,333
04/15/26
3
1
1,288

Nearby homes

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Assigned Schools

These are the assigned schools for 39 E Chestnut 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 Litchfield

At least 27 Trulia users voted on each feature.

  • 97 % Say car is needed

  • 92 % Say yards are well-kept

  • 91 % Say it's dog friendly

  • 83 % Say parking is easy

  • 76 % Say there's holiday spirit

  • 75 % Say people would walk alone at night

  • 73 % Say it's quiet

  • 71 % Say there's wildlife

  • 70 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 56 % Say kids play outside

  • 52 % Say there are community events

  • 45 % Say it's walkable to restaurants

  • 37 % Say there are sidewalks

  • 33 % Say it's walkable to grocery stores

  • 25 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Lucascridland
    "Litchfield hills 10k. Superb restaurants in the area. Wonderful nature walks. Connecticut at its finest."
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  • Rptcl
    "This is a beautiful town. Quaint, southern New England town with great architecture. The people are friendly and helpful. It has been our home for 43 years. I love my town. "
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    Flag
  • Mackr16
    "Very animal friendly as it is a rural community. Plenty of dog owners throughout the borough. Given the White Memorial Nature Preserve and ample public land, great place to be a dog"
    1
    Flag
  • Alix M.
    "Lots of people have dogs and all the various trails, green spaces, parks and public areas welcome them. Sadly, because a lot of streets are not high traffic, people allow their dogs to poop and don’t pick up (or they think it’s ok because they are walking in front of a farm). There are a couple of funky pet supply stores and almost every store has a dish of water outside. All the FedEx, UPS and USPS carriers have treats and know the dogs. Being an agricultural area, there is an abundance of vets!"
    1
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  • Lindsay.murphy108
    "Walk to town. Lots of kids for mine to run around with. Feels safe and friendly. I would recommend to anyone. "
    2
    Flag
  • Natalie M.
    "It’s a great place to live and I definitely highly recommend it for anyone. But a place, grow old in it, do it here. But only if you have the money to afford it because it’s expensive. But lots of history here so do it"
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  • Natalie M.
    "It’s woodsy and quiet. Nobody bother anyone and it’s primarily the safest place you could live. Highly recommend if you can afford it"
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  • Elizabeth C.
    "I have lived in this neighborhood for over a year and i love it! It is well kept, the neighborhood is nice, as well as the neighbors."
    3
    Flag
  • Wildirishrose
    "Lots of character—New England charm. A popular spot for tourists and retirees from NYC. Lots of great restaurants and cafes, low key bars. Shopping but it mostly comes at a premium. A great sense of community especially surrounding holidays and school events."
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  • juneglenn
    "Chestnut Hill is a very historic and beautiful location in Litchfield. One hundred year old maple trees line the road, along with beautiful stone walls. Hiking trails to the White Memorial Foundation are accessible from this location."
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  • sagetbarrows
    "Litchfield is a wonderful town full of history, activities and community involvement. There are many top notch restaurants, businesses and places to go. White Memorial, Tops mead State Park, Bantam Lake, skiing..The Warner Theatre are all here or within a 15 minute drive. The schools are rated high and are small enough so the kids all know each other or of each other. People from out of town are willing to pay a lot of money to spend weekends here. There are a lot of weekend homes but we are lucky to be able to live here everyday!"
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  • Ppnthr1
    "Quiet streets, relatively flat, good walking or cycling. Very private and quiet."
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Apartments for Rent

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Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Litchfield, CT

Homes for sale near 39 E Chestnut Hill Rd

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Off Market Homes Near 39 E Chestnut Hill Rd

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