116 Headquarters Rd, Litchfield, CT 06759
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Property image
OFF MARKET

116 Headquarters Rd
Litchfield, CT 06759

  • 4 Beds
  • 3.5 Baths
  • 3,531 sqft (on 3.79 acres)

$1,716,700

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $11,220/mo*

$1,716,700

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $11,220/mo*
4 Beds
3.5 Baths
3,531 sqft
(on 3.79 acres)

Local Information

  • Map ViewExplore the area around 116 Headquarters Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Serene and sought after riverfront setting in desirable Milton. Fully and completely renovated light filled home with legal guest apartment done with great style and taste. In characteristic understated Milton fashion, a peastone driveway leads you to private haven, past the frog pond, stone walls and gorgeous landscaping. Practically speaking there is carefully planned parking. A pergola covered front entrance welcomes you and you are in the country home of your dreams. Open and cheerful, you are transformed. The world goes away. From every living space take in the river below. Centrally located fireplace for dining or living space. Kitchen is open with plenty of storage, a bertazzoni range, a true cookhouse. Family room with raised hearth fireplace is spectacular yet cozy. Every detail thought out and every inch has been updated within 4-5 years. Baths are gorgeous marble yet simple and clean. The legal apartment is a beautifully appointed flat for your own guests. Square footage in listing does not reflect the additional sq ftg of apartment. This is a property you should not miss. Bear in mind, rarely does one find privacy and river frontage in quiet setting- nearly 200 ft along the East Branch of the Shepaug River with protected land across - paradise found.
116 Headquarters Rd, Litchfield, CT 06759 is a 4 bedroom, 4 bathroom, 3,531 sqft single-family home built in 1984. It last sold for $1,420,000 on Nov 23, 2020. It is currently off market. The Trulia Estimate is $1,716,700, with a rent estimate of $4,765/month.

Home Highlights

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

Home Details for 116 Headquarters Rd

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 9Types of Rooms: Laundry Room
Heating & Cooling
Heating: Forced Air, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Concrete
Appliances & Utilities
DisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 2

Lot Information

Lot Area: 3.79 acres

Price History for 116 Headquarters Rd

DatePriceEventSource
11/23/2020$1,420,000Sold
N/A
09/24/2020$1,495,000PendingAgent Provided
09/20/2020$1,495,000PriceChange
Agent Provided
08/03/2020$1,595,000Listed For SaleAgent Provided
01/30/2015$655,000Sold
Smart MLS #L150526

Market trends in Litchfield

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
19
2
MoM
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Property Tax and Assessment

Year2025
Tax$12,375
Assessment$618,760
Home facts updated by county records

Comparable Sales for 116 Headquarters Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.59
Single-Family Home
$1,275,000
06/30/26
4
2.5
3,192
1.05
Single-Family Home
$1,300,000
05/04/26
4
4
2,880
0.84
Single-Family Home
$355,000
02/24/26
3
2
2,392
0.87
Single-Family Home
$327,500
07/18/25
3
1.5
1,061
1.36
Single-Family Home
$638,000
11/03/25
3
1.5
1,680
1.70
Single-Family Home
$654,000
11/24/25
4
2.5
3,087
2.02
Single-Family Home
$1,225,500
09/19/25
4
2.5
2,740
1.85
Single-Family Home
$806,500
12/19/25
3
2.5
2,521
2.00
Single-Family Home
$1,163,000
08/07/25
3
2.5
3,449
1.91
Single-Family Home
$600,000
08/18/25
3
1.5
1,633

Nearby homes

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Assigned Schools

These are the assigned schools for 116 Headquarters Rd.
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."
  • 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. "
  • 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"
  • 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!"
  • Lindsay.murphy108
    "Walk to town. Lots of kids for mine to run around with. Feels safe and friendly. I would recommend to anyone. "
  • 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"
  • 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"
  • 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."
  • 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."
  • 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."
  • 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!"
  • Ppnthr1
    "Quiet streets, relatively flat, good walking or cycling. Very private and quiet."

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