20 Highmark Rd, Litchfield, CT 06759
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Property image
OFF MARKET

20 Highmark Rd
Litchfield, CT 06759

  • 4 Beds
  • 2.5 Baths
  • 2,876 sqft (on 2.80 acres)

$859,600

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $5,792/mo*
Refinance Your Home

$859,600

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $5,792/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,876 sqft
(on 2.80 acres)

Local Information

  • Map ViewExplore the area around 20 Highmark Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2003
Lot Size
2.8 acres
Living Area
2,876 sqft
Price/Sqft
$299
Parking
Garage

About this House

Situated on a quiet cul-de-sac on almost three glorious acres, this splendid, custom-built colonial is move-in ready and features a spacious eating space kitchen that is open to the family room with wood burning fireplace. Generous formal living room and dining room with hardwood flooring on the main level. The extended screened-in porch with mahogany flooring provides lovely views of the vineyard and is a fine place to relax or entertain guests. The mud room and half bath complete the main level along with the attached two-car garage for easy access to the kitchen. The upper level features a master bedroom suite with wall to wall carpeting and updated master bath. Three comfortable bedrooms with carpeting, an updated full bath and bonus room complete the upper level. Mechanical features include an oil furnace, ductless cooling & heating units, and portable generator. The yard is nicely landscaped, a portion of the backyard has a wood fence and is accented with the stonewall. Just minutes to Litchfield Green. Easy commuting to Routes 118, 63 and 8.
20 Highmark Rd, Litchfield, CT 06759 is a 4 bedroom, 3 bathroom, 2,876 sqft single-family home built in 2003. It last sold for $430,000 on Jul 15, 2019. It is currently off market. The Trulia Estimate is $859,600, with a rent estimate of $4,628/month.

Home Details for 20 Highmark Rd

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherGarden
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.80 acres

Price History for 20 Highmark Rd

DatePriceEventSource
07/15/2019$430,000Sold
Smart MLS #170078765
05/13/2019$479,900PendingAgent Provided
05/10/2019$479,900PendingToActiveAgent Provided
04/26/2019$479,900PendingAgent Provided
04/15/2019$479,900PriceChange
Agent Provided
02/26/2019$484,900PriceChange
Agent Provided
09/25/2018$489,900PriceChange
Agent Provided
08/24/2018$499,900PriceChange
Agent Provided
07/06/2018$515,000PriceChange
Agent Provided
06/30/2018$525,000Listed For SaleAgent Provided

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
2MoM
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Property Tax and Assessment

Year2025
Tax$11,556
Assessment$577,790
Home facts updated by county records

Comparable Sales for 20 Highmark Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21 Camp Dutton Road, Litchfield, CT
0.61
Single-Family Home
$575,000
11/07/25
3
2
1,448
365 South Street, Litchfield, CT
0.87
Single-Family Home
$785,000
08/11/25
3
3
2,220
265 South St, Litchfield, CT
1.01
Single-Family Home
$308,000
05/11/26
3
3
3,336
137 Old South Road, Litchfield, CT
0.96
Single-Family Home
$770,000
03/20/26
4
2.5
2,702
28 West Chestnut Hill Road, Litchfield, CT
1.01
Single-Family Home
$1,250,000
01/12/26
3
3.5
4,068
11 West Chestnut Hill Road, Litchfield, CT
1.15
Single-Family Home
$765,000
05/01/26
5
3.5
3,328
645 South Plains Road, Litchfield, CT
1.00
Single-Family Home
$500,000
10/21/25
3
2.5
1,232
93 Northfield Road, Litchfield, CT
0.83
Single-Family Home
$1,700,000
12/29/25
4
4
4,182
144 Meadow Street, Litchfield, CT
1.34
Single-Family Home
$533,200
11/21/25
3
2
2,244
42 Chestnut Hill Rd, Litchfield, CT
0.86
Single-Family Home
$1,500,000
06/23/26
7
4
5,578

Nearby homes

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Assigned Schools

These are the assigned schools for 20 Highmark 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 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.
  • Rptcl
    "People are always walking dogs here it is a wonderful place to live. Quiet and peanut and beautiful. "
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  • Lucascridland
    "Litchfield hills 10k. Superb restaurants in the area. Wonderful nature walks. Connecticut at its finest."
    0
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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. "
    0
    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
    Flag
  • 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"
    0
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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."
    0
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