38 Highland Ave, Redding, CT 06896
Property image
Property image
OFF MARKET

38 Highland Ave
Redding, CT 06896

  • 3 Beds
  • 2.5 Baths
  • 2,478 sqft (on 0.46 acres)

$776,600

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $5,059/mo*

$776,600

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $5,059/mo*
3 Beds
2.5 Baths
2,478 sqft
(on 0.46 acres)

Local Information

  • Map ViewExplore the area around 38 Highland Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Travel back in time to experience this impeccably restored, updated and maintained 1929 Arts and Crafts bungalow. Rare and beautiful, this distinctive home has been lovingly cared for by just three families since its inception. Marvel at the period architecture and interior design which has been meticulously restored to its original splendor while modern amenities have been âquietlyâ added to meet todayâs needs. Current owner has painstakingly added exceptional touches such as copper half-round gutters, Arroyo Craftsman light fixtures, hand-hammered copper farmhouse sink, hand-blown glass cabinet hardware and a large wine cellar. Special features include beautifully restored original wood floors and window, door and baseboard moldings, newer kitchen cabinets, granite counters and stainless appliances. Plus, a Butlerâs Pantry that was designed to serve as a âBakerâs Pantry.â Gorgeous stone fireplace in the spacious yet cozy living room. Three generously sized bedrooms, 2.5 baths, and a finished basement (additional square feet) round off this architecturally significant home. Perched atop a small hill, nestled at the end of a quiet cul-de-sac this property feels like a vacation hideaway yet itâs just a 3-minute walk to the ever-popular Georgetown area with fabulous restaurants and shops. For commuters, itâs less than a mile to Rt. 7 and only 1.7 miles to the Branchville train station (Metro North). A perfect home for your year-round retreat or your weekend escape.
38 Highland Ave, Redding, CT 06896 is a 3 bedroom, 3 bathroom, 2,478 sqft single-family home built in 1929. It last sold for $480,000 on Jan 11, 2021. It is currently off market. The Trulia Estimate is $776,600, with a rent estimate of $4,442/month.

Home Highlights

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

Home Details for 38 Highland Ave

Interior Features

Heating & Cooling
Heating: Baseboard, OilHeating Fuel: Baseboard
Interior Details
Number of Rooms: 6
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigerator
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1929
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price History for 38 Highland Ave

DatePriceEventSource
01/11/2021$480,000Sold
Smart MLS #170350389
11/11/2020$440,000PendingAgent Provided
11/06/2020$440,000Listed For SaleAgent Provided
08/16/1999$297,000Sold
Smart MLS #98045340
06/28/1993$162,500Sold
Smart MLS #93130555

Market trends in Redding

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
49
20
MoM
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Property Tax and Assessment

Year2025
Tax$9,825
Assessment$332,600
Home facts updated by county records

Comparable Sales for 38 Highland Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.29
Single-Family Home
$639,000
08/20/25
4
1.5
1,938
0.41
Single-Family Home
$549,000
05/01/26
2
2
1,952
0.32
Single-Family Home
$505,000
01/30/26
2
2
1,544
0.50
Single-Family Home
$600,000
10/06/25
3
2
1,314
0.36
Single-Family Home
$1,040,000
12/05/25
4
3
2,854
0.13
Single-Family Home
$790,000
08/06/25
3
2.5
2,022
0.52
Single-Family Home
$625,000
07/17/25
2
1.5
1,406
0.67
Single-Family Home
$820,000
07/11/25
3
3.5
2,500
0.49
Single-Family Home
$700,000
12/02/25
3
2
1,840
0.35
Single-Family Home
$1,261,000
06/26/26
4
3.5
3,631

Nearby homes

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Assigned Schools

These are the assigned schools for 38 Highland Ave.
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 Redding

At least 41 Trulia users voted on each feature.
  • 96 % Say there's wildlife

  • 91 % Say parking is easy

  • 88 % Say car is needed

  • 87 % Say there's holiday spirit

  • 86 % Say it's dog friendly

  • 84 % Say it's quiet

  • 76 % Say yards are well-kept

  • 71 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 63 % Say there are community events

  • 59 % Say people would walk alone at night

  • 42 % Say kids play outside

  • 33 % Say it's walkable to restaurants

  • 12 % Say it's walkable to grocery stores

  • 12 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Drewluca
    "Many families; safe; lots of space. Great place to live and raise kids. Friendly and close enough to everything to make it pleasant. "
  • Helga P.
    "We work from home. Therefore, we do not have a commute unless we have outside business meetings or other work related engagements. "
  • Betsy M.
    "We have potlucks and cookouts on our lane, and spontaneous get-togethers for cocktails. People always Everyone on our lane pitches in to help one another whenever needed. I wouldn’t say that’s the case for Redding as a whole, but definitely true on our lane!"
  • Agustahalla
    "A great place for small children. We work from home. This is a very peaceful place without being too remote. I love living here. ;-)"
  • Agustahalla
    "Quiet. Relatively safe for children. Great things to do outdoors near by. The town has organized great camps for kids through the summertime."
  • Jenbain23
    "My commute varies as I work at different locations. Fairfield County in general is horrible for rush hour traffic but when traveling North it could be less congested. "
  • Jenbain23
    "Love the neighborhood, but I don’t love the amount of people in town who have little awareness of appropriate fiscal responsibility with town finances."
  • Deidreyw
    "Nice small town, with plenty to do nearby. Great schools, many stores/shopping areas in surrounding towns and safe areas."
  • Deidreyw
    "It’s a nice small town with great schools, a lot of parks, and things to do in the area if you have little ones. Also, really nice restaurants in the area, so you don’t need to go far. There is a train station nearby and close to lots of shopping, highways and New York City!"
  • einarulfsson
    "Redding is the best Value in Fairfield County, amazing Schools, parks and recreation available."
  • Janeausten
    "Fabulous town full of wonderful parks and hiking trails. Town library started by Mark Twain and a hub of activity. Summer Concerts on the Green gather young and old to enjoy music and fun together. Excellent schools- always in top 10. "
  • Pdunay
    "Live and work here. Beautiful and peaceful country life. Great schools and very safe. "
  • rtklarsfeld
    "Part of prestigious Farview Farm Association with pool club and tennis courts. Completely updated in 2013. Custom gourmet kitchen of your dreams with double European dishwashers, Wolf 6 burner range, double ovens, warming drawer, Sub-Zero All Refrigerator and All Freezer . 3 car garage. Finished lower level 785 sq/ft for a total of 4,422 sq/ft."

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Homes for sale near 38 Highland Ave

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Off Market Homes Near 38 Highland Ave

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