285 Redding Road, Redding, CT 06896
OFF MARKET

285 Redding Road
Redding, CT 06896

  • 3 Beds
  • 3.5 Baths
  • 3,726 sqft (on 7.31 acres)

$1,746,500

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $11,074/mo*

$1,746,500

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $11,074/mo*
3 Beds
3.5 Baths
3,726 sqft
(on 7.31 acres)

Homes for sale near 285 Redding Road

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Apartments for Rent

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Local Information

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

Description

Hawk's Nest - extraordinary country retreat on 7.31 acres w/gated private entry including the ca 1800 historic converted barn w/modern glass & stone addition; heated gunite pool; gambrel-roofed barn w/4 stalls, hayloft, garage/workshop & cupola; greenhouse; root cellar; detached 3 bay garage; plus over 7 acres of gently sloping meadows/woodlands, bounded by split-rail fencing, stone walls, & scenic pond. Owned by Frank M. Hawks in the 1930s, one of America's leading aviation pioneers, this storied home was originally a barn that was moved back from the main road, & parts of the interior were constructed of beams & brick salvaged from Mark Twain's nearby "Stormfield" after it burned. Architect Roger Pitt Witcomb artfully designed the modern conversion of the original barn incorporating the spectacular "garden room" addition w/ two story wall of windows & glorious waterfall w/native stone backdrop. A circular staircase climbs to the 2nd floor FR w/large stone fireplace & curved balcony overlook. This truly one of a kind residence offers stunning brick & wide board floors; timbered ceilings/exposed beams; 3 stone fireplaces + wood burning stove; gracious DR w/adjoining wine bar/cellar; & 3 finished levels. Total 3,726sf, 3 BR & 3/1 baths including primary suite w/full bath, dressing room & sleeping porch, plus 2 more ensuite BRs on the 3rd floor w/vltd ceilings, beams & one w/sleeping loft. Glorious private retreat yet convenient West Redding location, only 63 miles to Midtown.
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. This description is from October 20, 2023

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 285 Redding Road

Interior Features

Interior Details
Basement: NoneNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Family Room, Great Room, Kitchen, Living Room, Loft, Other
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3726 Square Feet
Appliances & Utilities
Appliances: Gas Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: Patio, PorchFencing: PrivacyOther Structures: Barn(s), Shed(s)Exterior: Fruit Trees, Lighting, Stone WallFoundation: StoneHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Detached,Private
Pool
Pool: In Ground, Pool/Spa Combo, Heated, GunitePool
Frontage
WaterfrontWaterfront: Waterfront, PondOn Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3726 Square Feet

Property Information

Year Built
Year Built: 1800
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Antique,Modern
Building
Construction Materials: Shingle Siding, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 270680

Price & Status

Price
List Price: $1,495,000
Status Change & Dates
Off Market Date: Fri Oct 13 2023Possession Timing: Immediate

Active Status

MLS Status: Closed

Location

Direction & Address
City: ReddingCommunity: West Redding
School Information
Elementary School: ReddingJr High / Middle School: John ReadHigh School: Joel Barlow

Building

Building Area
Building Area: 3726 Square Feet

HOA

No HOA

Lot Information

Lot Area: 7.31 Acres

Miscellaneous

Mls Number: 170588980Attic: NoneAbove Grade Unfinished Area: 3726
Last check for updates: about 13 hours ago
Listed by Laura Ancona, (203) 733-7053
William Pitt Sotheby's Int'l, (203) 438-9531
Bought with: Laura Ancona, (203) 733-7053, William Pitt Sotheby's Int'l, (203) 438-9531
Source: Smart MLS, MLS#170588980

Price History for 285 Redding Road

DatePriceEventSource
10/19/2023$1,550,000Sold
Smart MLS #170588980
08/04/2023$1,495,000Listed For SaleSmart MLS #170588980
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Property Tax and Assessment

Year2025
Tax$18,787
Assessment$636,000
Home facts updated by county records

Comparable Sales for 285 Redding Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.12
Single-Family Home
$939,000
02/17/26
4
3.5
4,641
0.22
Single-Family Home
$1,150,000
06/30/25
4
3
3,020
0.34
Single-Family Home
$767,000
11/03/25
4
2.5
2,958
0.45
Single-Family Home
$940,000
03/30/26
4
3.5
3,578
0.58
Single-Family Home
$1,160,000
09/18/25
4
3.5
3,156
0.85
Single-Family Home
$1,600,000
10/02/25
6
4.5
3,573
0.53
Single-Family Home
$942,000
07/15/25
4
3
2,619
0.81
Single-Family Home
$798,000
07/10/25
3
2.5
2,909
0.66
Single-Family Home
$1,799,000
01/13/26
5
4
2,452
0.59
Single-Family Home
$725,000
12/03/25
4
2.5
1,678

Assigned Schools

These are the assigned schools for 285 Redding Road.
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."

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Homes for rent near 285 Redding Road

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Off Market Homes Near 285 Redding Road

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285 Redding Road, Redding, CT 06896 is a 3 bedroom, 4 bathroom, 3,726 sqft single-family home built in 1800. This property is not currently available for sale. 285 Redding Road was last sold on Oct 19, 2023 for $1,550,000 (4% higher than the asking price of $1,495,000). The current Trulia Estimate for 285 Redding Road is $1,746,500.