271 Redding Rd, Redding, CT 06896
OFF MARKET

271 Redding Rd
Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 3,495 sqft (on 3.31 acres)

$1,111,200

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $7,073/mo*

$1,111,200

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $7,073/mo*
4 Beds
3 Baths
3,495 sqft
(on 3.31 acres)

Homes for sale near 271 Redding Rd

Skip to last item
Skip to first item

Apartments for Rent

Skip to last item
Skip to first item

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Own a piece of American history outfitted for the modern buyer. The John Lee House, c.1773 has been preserved with so many original features and yet transformed. One of the oldest known homes in the picturesque Redding. Initially this home started as a farm, later a boy's school and then back to the stunning homestead sitting on bucolic 3.3 acres. Original features include, but not limited to, 5 fireplaces, hand-hewn beams, wide board chestnut floors, an original dumbwaiter. Modern kitchen with two story family room opens to the massive two-tier bluestone patio. Entertain your guests from the stunning dinning room with enormous fireplace and french doors leading to your patio as well. As you can imagine so many improvements have been made to this 4BR, 3BA home but none so much as with this current owner. Recent Improvements include, asphalt roof replaced with period correct cedar shakes (2018), Entire heating system revamped to Triangle tube 95% efficient propane gas fired boiler and hot water heater (2019) Central Air added (2021) New 400' well (2020) Bluestone Patio spans the entire back of the home complete with 2' seating wall (2019) Whole house Kohler 20kw LP/NG Generator (2020), the list goes on and on!
Wait until you see this property! Stunning acreage, a huge two story barn with electricity sitting on a gravel horseshoe shaped driveway. POOL SITE has recently been identified (near firepit) for future consideration. Exterior Painting in progress.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 271 Redding Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: WoodPatio
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1773
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 3.31 acres

Price History for 271 Redding Rd

DatePriceEventSource
06/30/2021$790,000Sold
Smart MLS #170397901
05/20/2021$750,000ContingentSmart MLS #170397901
05/16/2021$750,000Listed For SaleSmart MLS #170397901
07/05/2016$580,000Sold
Smart MLS #99137008
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$16,232
Assessment$549,500
Home facts updated by county records

Comparable Sales for 271 Redding Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.29
Single-Family Home
$767,000
11/03/25
4
2.5
2,958
0.15
Single-Family Home
$939,000
02/17/26
4
3.5
4,641
0.25
Single-Family Home
$1,150,000
06/30/25
4
3
3,020
0.40
Single-Family Home
$940,000
03/30/26
4
3.5
3,578
0.51
Single-Family Home
$942,000
07/15/25
4
3
2,619
0.74
Single-Family Home
$798,000
07/10/25
3
2.5
2,909
0.60
Single-Family Home
$725,000
12/03/25
4
2.5
1,678
0.55
Single-Family Home
$1,160,000
09/18/25
4
3.5
3,156
0.35
Single-Family Home
$730,000
06/17/25
3
2
1,769
0.91
Single-Family Home
$900,000
10/16/25
4
2.5
3,270

Assigned Schools

These are the assigned schools for 271 Redding 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 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

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."

LGBTQ Local Legal Protections

Homes for rent near 271 Redding Rd

Skip to last item
Skip to first item

Off Market Homes Near 271 Redding Rd

Skip to last item
Skip to first item
271 Redding Rd, Redding, CT 06896 is a 4 bedroom, 3 bathroom, 3,495 sqft single-family home built in 1773. This property is not currently available for sale. 271 Redding Rd was last sold on Jun 30, 2021 for $790,000. The current Trulia Estimate for 271 Redding Rd is $1,111,200.