3808 Redding Road, Fairfield, CT 06824
Property image
Property image
UNDER CONTRACT
16.76 ACRES

$2,275,000

  • 4 Beds
  • 4.5 Baths
  • 5,376 sqft (on 16.76 acres)

3808 Redding Road, Fairfield, CT 06824

Est. Mortgage $15,449/mo*
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Home Highlights

Single-Family Home
Built in 1769
16.76 acre lot
$423/sqft
2 Car Garage

Local Information

  • Map ViewExplore the area around 3808 Redding Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original beams and centuries-old floors remain at the core, while refreshed interiors and natural light bring a sense of clarity and renewal throughout. A rare three-fireplace hearth anchors the main living spaces, creating a natural center point for gathering. Four bedrooms and four and a half baths offer both comfort and flexibility, including a primary suite with a private balcony overlooking the property as it comes alive in the spring. The land is expansive, yet entirely manageable. Nearly eighteen acres unfold into open fields, budding orchards, and wooded edges - offering the option to embrace the full scale of the property or maintain a more modest footprint. Whether for gardening, recreation, or quiet enjoyment, the setting adapts easily. A historic barn, carriage house, and chicken coop add character and versatility. Privately set yet just minutes from town, this is a property that delivers both space and convenience. 3808 Redding Road offers a sense of history, a renewed perspective, and the flexibility to live as you choose. Barn sold as is
Last check for updates: about 4 hours ago
Listing courtesy of Cindy Raney, (203) 625-1820
Coldwell Banker Realty, (203) 625-1820
Source: Smart MLS, MLS#24171406
Also Listed on Smart MLS.

Home Details for 3808 Redding Road

Interior Features

Interior Details
Basement: Full,Unfinished,Storage Space,Interior EntryNumber of Rooms: 14Types of Rooms: Master Bedroom, Bedroom, Bathroom, Den, Dining Room, Kitchen, Living Room, Media Room, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5376 Square Feet
Appliances & Utilities
Appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Tankless Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Wood/Coal Stove,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltOther Structures: Shed(s), Barn(s), Guest HouseExterior: Fruit Trees, GardenFoundation: Concrete PerimeterGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Frontage
Waterfront: Beach AccessNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Farm & Range
Allowed to Raise Horses
Finished Area
Finished Area (above surface): 5376 Square Feet

Days on Market

Days on Market: 145

Property Information

Year Built
Year Built: 1769
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shingle Siding, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: see inclusions/excusionsParcel Number: 129845

Price & Status

Price
List Price: $2,275,000Price Per Sqft: $423
Status Change & Dates
Off Market Date: Fri Aug 28 2026Possession Timing: Negotiable

Active Status

MLS Status: Under Contract

Location

Direction & Address
City: FairfieldCommunity: Greenfield Hill
School Information
Elementary School: BurrJr High / Middle School: TomlinsonHigh School: Fairfield Warde

Agent Information

Listing Agent
Listing ID: 24171406

Building

Building Area
Building Area: 5376 Square Feet

Community

Community Features: Golf, Playground, Near Public Transport, Stables/Riding, Tennis Court(s)
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 16.76 Acres

Miscellaneous

BasementMls Number: 24171406Zillow Contingency Status: Under ContractAttic: Walk-upAttribution Contact: (203) 625-1820Above Grade Unfinished Area: 5376

Additional Information

GolfPlaygroundNear Public TransportStables/RidingTennis Court(s)

Around this home

What Locals Say about Fairfield

At least 343 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 87 % Say car is needed

  • 85 % Say parking is easy

  • 82 % Say yards are well-kept

  • 79 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 71 % Say kids play outside

  • 66 % Say they plan to stay for at least 5 years

  • 66 % Say it's quiet

  • 64 % Say there's wildlife

  • 61 % Say neighbors are friendly

  • 61 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 57 % Say it's walkable to restaurants

  • 50 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • teddyabby
    "It’s safe and pretty and everyone looks out for one another. There is a bunch of cute parks and a nice walkable downtown."
    0
    Flag
  • Bnsdkbr225
    "Friendly and beautiful. Close to Lake Mohegan and parks. Lake rights to Lake Hill’s association . "
    0
    Flag
  • Kevin.cohen318
    "Great place to raise a family, incredibly safe and has all the amenities you could want on a year round basis."
    0
    Flag
  • Alexande.pappas
    "Yes walking miking kids walking to school we have public beaches lake’s plenty of restaurants churches"
    0
    Flag
  • Samuel Rivera
    "Great town for families with kids. Fairfield offers great schools, good supermarkets, tons of restaurants and entertainment "
    0
    Flag
  • Timothy Moss
    "Very family friendly. Great place to live for people of any age. I’ve lived here for 10 years now….."
    0
    Flag
  • Kevin.cohen318
    "5 minutes to either I-95, the Merritt Parkway or metro north, train to NYC is just over an hour each way. Great town that’s close to everything but not too close to anything."
    1
    Flag
  • Trulia User
    "My neighbor is safe and friendly and very clean as well. I've lived in this neighborhood over 18 years and absolutely love it. Thank you "
    3
    Flag
  • Trulia User
    "A very well maintained area . Homes streets ,business ,beaches schools ,library’s ( 3 ) . So much to offer !"
    0
    Flag
  • Sauerh
    "My neighborhood is family-oriented with distinct yet harmonious homes with well- kept yards. We are a short trip from Bridgeport, Norwalk, and Stamford with excellent connections via Metro North and I-95."
    5
    Flag
  • Isabellecj
    "Great neighborhood , good schools, close to town and railway station and beach . Very safe and quiet , properties well maintained and kids friendly . Love my neighborhood!"
    3
    Flag
  • Collin M.
    "Tons of events. Parties. Free concerts etc. there is so much fun things to do and see here. Beaches are amazing!"
    0
    Flag
  • Ab h
    "Walk to absolutely everything from hop on the train to yankee stadium or going to your dentist. Beautiful beaches and parks at your fingertips and children’s activities galore."
    0
    Flag
  • Juan G.
    "Quiet, clean and a good place to raise your kids. The school system it’s awesome and you know your kids are in good hands. "
    1
    Flag
  • Imeiers
    "We have neighbourhood block parties, the best trick or treating in town and a wonderful community spirit. Easily one of the best neighbourhoods in Fairfield. "
    5
    Flag
  • Troy P.
    "I work in Fairfield and it’s a wonderful town. The drive from New Haven is pretty easy with 2 route options either 95 or the merit parkway. "
    0
    Flag
  • Juan G.
    "Best in Connecticut, I have lived here for 6 years and my kids love it. If you want a place to raise your kids this it is the place "
    0
    Flag
  • Sar K.
    "Block parties, neighborhood watch, strong neighbor community, varying ages, active community, holiday celebrations: memorial parade, pancake breakfast, Christmas tree lighting, movies at the beach, music on the green, amazing local restaurants, 4th of July fireworks and much more"
    3
    Flag
  • DE
    "Very safe and relatively diverse. Great schools and decent restaurants. The beach is close by and some good golf courses."
    1
    Flag
  • Raquel.noi
    "Would love it, plenty of space for the dogs to run. Walking trails, beautiful neighborhoods to got for a walk. You will love it here!!"
    0
    Flag
  • Raquel
    "Great place, great community environment! It is such nice to go for walks and feel safe. We love that we found our home here!"
    0
    Flag
  • Raquel
    "Great family environment, lots of parks. Neighbors are friendly and welcoming. A lot of activities for kids. "
    0
    Flag
  • Lisalberts
    "It’s friendly and easy to walk or ride bikes around. The schools are wonderful. A real community feel."
    0
    Flag
  • Alek M.
    "Great town to raise a family, good schools and safe neighborhoods for your kids. Friendly people and clean area all around."
    1
    Flag
  • Fortress.management
    "Excellent schools, great town amenities makes it a great area to raise a family. Commuting to NYC is a little over an hour. Vibrant restaurant scene."
    0
    Flag
  • John S. W. J.
    "A great family oriented town. We love the parks the beaches and the community atmosphere. We couldn’t imagine living anywhere else"
    0
    Flag
  • Blythe A. B.
    "Driving to the train station is easy but parking passes are hard to come by unless you find street parking. waiting list is 18 months. "
    0
    Flag
  • Blythe A. B.
    "Everyone walks their dogs. sidewalks are well maintained. there are plenty of parks as well, both dog parks and free space parks. it is well kept by all dog owners, and it’s expected that you pick up after them!"
    0
    Flag
  • Bellaamore99
    "Close to parks, Wholefoods , Homedepo, shopping and metronorth train. Great neighbores . And feel very safe. "
    5
    Flag
  • Mjcejbart
    "Dog walking Mecca at lake Mohegan. All dogs welcome. Very dog friendly. Nice lake and trails to enjoy with or without a dog. "
    0
    Flag
  • Cheetah4455
    "Christmas walk around in Toilsome Hill. Meet the neighbors and everyone brings a different plate of food"
    1
    Flag
  • al .P
    "Lots of dogs on leaches . Not having your dog on a leach is not a good idea . You know your dog but the other does not know your dog "
    1
    Flag
  • Nour Y.
    "One dog can annoy a lot of families since homes are close to each other so multiple dogs barking is even worse"
    5
    Flag
  • Bassickrachel
    "I do see dogs frequently. People seem friendly, neighbors are quiet. I love airfield for the commute and small Town atmosphere."
    1
    Flag
  • Bassickrachel
    "Excellent I am 5 minutes from I-95 and Fairfield Metro Train Station. It is close to grocery stores and it is quite with friendly people."
    0
    Flag
  • Dennis
    "Many dogs that are very pleasant. Owners stop and chat while dogs play. Great way to meet your neighbors."
    0
    Flag
  • Larry
    "Moved here from Dallas and absolutely love it. I commute to downtown New Haven by car and it’s about 30-35 minutes."
    0
    Flag

Market trends in Fairfield

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$986K
$28.33KMoM
Sale-to-List Price
103.8%
0.2%MoM
Price per sq ft
$473
$1MoM
Available listings
129
33MoM

Home Value

Trulia Estimate
$2.15M
Since last month
Decreased$4K (-0.2%)
Since last year
Decreased$201K (-8.5%)
Since last sale
Increased$550K (+34.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +100% in the last 10 years
MonthEstimated value
2026
September 2026$2.15M
August 2026$2.15M
July 2026$2.15M
June 2026$2.32M
May 2026$2.37M
April 2026$2.52M
February 2026$2.44M
January 2026$2.39M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3725 Redding Road, Fairfield, CT
0.08
Single-Family Home
$1,300,000
06/15/26
4
3.5
4,070
4041 Redding Road, Fairfield, CT
0.22
Single-Family Home
$1,400,000
08/03/26
5
4
4,202
3233 North Street, Fairfield, CT
0.35
Single-Family Home
$1,850,000
08/18/26
5
4.5
5,700
2775 North St, Fairfield, CT
0.24
Single-Family Home
$2,350,000
01/15/26
5
7
5,978
301 Redding Road, Easton, CT
0.27
Single-Family Home
$1,199,000
07/30/26
3
3.5
2,598
223 Mistywood Lane, Fairfield, CT
0.37
Single-Family Home
$1,380,000
06/25/26
4
2.5
3,039
100 East Common Road, Easton, CT
0.57
Single-Family Home
$1,000,000
12/19/25
4
5
6,056
116 Mile Common, Easton, CT
0.71
Single-Family Home
$1,266,000
08/12/26
4
3
4,734
140 Mile Common Road, Easton, CT
0.59
Single-Family Home
$1,501,000
04/15/26
3
3.5
3,452

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
3901 Redding Road, Fairfield, CT 06824
0.09
$1,495,000
5
3.5
2,866
For Sale
3920 Redding Road, Fairfield, CT 06430
0.11
$2,040,200
4
4
6,000
Off Market
3725 Redding Road, Fairfield, CT 06824
0.08
$1,300,000
4
3.5
4,070
Recently Sold
3781 Redding Road, Fairfield, CT 06824
0.11
$1,322,700
4
2.5
2,640
Off Market
4041 Redding Road, Fairfield, CT 06824
0.22
$1,400,000
5
4
4,202
Recently Sold
240B Foggwood Road, Fairfield, CT 06430
0.22
$1,756,600
4
4
4,500
Off Market
3659 Redding Road, Fairfield, CT 06824
0.18
$1,790,700
4
3.5
4,056
Off Market
301 Redding Road, Easton, CT 06612
0.27
$1,199,000
3
3.5
2,598
Recently Sold
2775 North St, Fairfield, CT 06824
0.24
$2,350,000
5
7
5,978
Recently Sold
53 Leslie Lane, Fairfield, CT 06824
0.30
$1,701,200
4
3.5
3,500
Off Market
285 Redding Road, Easton, CT 06612
0.34
$2,341,900
5
4.5
3,900
Off Market
3233 North Street, Fairfield, CT 06824
0.35
$1,850,000
5
4.5
5,700
Recently Sold

Price and Tax history

DateEventPrice
Aug 29, 2026
Source: Smart MLS #24171406
Pending
$2,275,000
Jul 9, 2026
Source: Smart MLS #24171406
PriceChange
$2,275,000
Price decreased by 7%
May 13, 2026
Source: Smart MLS #24171406
PriceChange
$2,450,000
Price decreased by 6%
Apr 30, 2026
Source: Smart MLS #24171406
Listed For Sale
$2,595,000
Apr 29, 2026
Source: Smart MLS #24160945
ListingRemoved
$2,595,000

LGBTQ Local Legal Protections

Cindy Raney, Coldwell Banker Realty, (203) 625-1820
Agent Phone: (203) 625-1820
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 3808 Redding Road

  • What is the estimated monthly payment for 3808 Redding Road?
    Based on a $2,275,000 list price with 20% down at today's rates, the estimated monthly payment for 3808 Redding Road in Fairfield, CT is approximately $15,635 (about $12,356 principal & interest, $3,204 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 3808 Redding Road compare to homes in Fairfield?
    3808 Redding Road in Fairfield, CT is listed at $2,275,000, about 131% above the $986K median sale price in Fairfield.
  • What do residents say about Fairfield?
    Residents describe Fairfield, CT as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Fairfield, CT.
  • What are the closest schools to 3808 Redding Road?
    The closest schools to 3808 Redding Road in Fairfield, CT are Burr Elementary School (rated 8/10), Fairfield Warde High School (rated 9/10), Tomlinson Middle School (rated 8/10).
  • Does 3808 Redding Road have air conditioning?
    Yes, 3808 Redding Road in Fairfield, CT has air conditioning.
  • Does 3808 Redding Road have laundry facilities?
    Yes, 3808 Redding Road in Fairfield, CT has in-unit laundry.
3808 Redding Road, Fairfield, CT 06824 is a 4 bedroom, 5 bathroom, 5,376 sqft single-family home built in 1769. This property is currently available for sale and was listed by Smart MLS on Apr 30, 2026. The MLS # for this home is MLS# 24171406.