2281 Redding Road, Fairfield, CT 06824
SOLD
FEB 9, 2026

2281 Redding Road
Fairfield, CT 06824

  • 5 Beds
  • 4.5 Baths
  • 4,191 sqft (on 5.03 acres)

$4,700,000

Last Sold: Feb 9, 2026
6% below list $5M
$1,121/sqft
Est. Refi. Payment $30,262/mo*
Refinance Your Home

$4,700,000

Last Sold: Feb 9, 2026
6% below list $5M
$1,121/sqft
Est. Refi. Payment $30,262/mo*
Refinance Your Home
5 Beds
4.5 Baths
4,191 sqft
(on 5.03 acres)

Local Information

  • Map ViewExplore the area around 2281 Redding Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's kitchen opens to elegant dining and living areas, with French doors to a bluestone terrace designed for candlelit dinners under the stars. A first-floor guest suite with a full bath provides flexibility and privacy, while upstairs, four additional bedrooms-including a serene primary suite-offer refined comfort and room to breathe. Beyond the home, the grounds unfold like a private resort. A two-story pool house features a full kitchen, bath, and playful loft. A climate-controlled barn houses a Trackman 4 golf simulator, sauna, and space for training or unwinding. Outdoors, discover a saltwater pool and spa, sport court, vegetable gardens, wildflower meadow with carved walking trails, orchard of apple, cherry, and peach trees, and a cider press-all with a private path leading to the Patterson Club. Whether for weekends or a lifetime, this estate elevates every season and every gathering-minutes from town, yet a world apart.
2281 Redding Road, Fairfield, CT 06824 is a 5 bedroom, 5 bathroom, 4,191 sqft single-family home built in 1941. It last sold for $4,700,000 on Feb 9, 2026 (6% below the $4,995,000 asking price). It is currently off market. The Trulia Estimate is $4,848,900, with a rent estimate of $8,288/month.

Home Highlights

Parking
4 Car Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$1,121/sqft
Listed
180+ days ago

Home Details for 2281 Redding Road

Interior Features

Interior Details
Basement: Full,Sump Pump,Storage Space,Garage Access,Partially Finished,ConcreteNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4191 Square Feet
Appliances & Utilities
Appliances: Gas Range, Convection Oven, Refrigerator, Dishwasher, Washer, Dryer, Wine Cooler, Gas Water Heater, Water Heater, HumidifierDishwasherDryerLaundry: Upper LevelRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural Gas,PropaneHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 4Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane WindowsDoor: French Doors
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: PatioFencing: FullOther Structures: Barn(s), Greenhouse, Pool HouseExterior: Lighting, Tennis Court(s), Fruit Trees, Garden, Stone Wall, Underground SprinklerFoundation: Concrete Perimeter, StoneGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageParking Spaces: 4Parking: Attached,Detached,Garage Door Opener
Pool
Pool: Heated, Pool/Spa Combo, In GroundPool
Frontage
Waterfront: Beach Access, Water CommunityNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3651 Square FeetFinished Area (below surface): 540 Square Feet

Property Information

Year Built
Year Built: 1941
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Stone, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Not Included in Sale: Please see attached inclusions/exclusions addendumParcel Number: 133066

Price & Status

Price
List Price: $4,995,000Price Per Sqft: $1,121/sqft
Status Change & Dates
Off Market Date: Fri Dec 26 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

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

Agent Information

Buyer Agent
Buyer Company Name: VARTULI | JABICK TEAM AT KELLER WILLIAMS REALTY

Building

Building Area
Building Area: 4191 Square Feet

Community

Community Features: Golf, Health Club, Library, Paddle Tennis, Private School(s), Stables/Riding, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 5.03 Acres

Energy

Energy Efficiency Features: Thermostat, Windows

Miscellaneous

BasementMls Number: 24127092Attic: Pull Down StairsAttribution Contact: (203) 257-8320Above Grade Unfinished Area: 3651Activation Date: Sat Sep 27 2025

Additional Information

GolfHealth ClubLibraryPaddle TennisPrivate School(s)Stables/RidingTennis Court(s)
Last check for updates: about 7 hours ago
Listed by Cindy Raney, (203) 257-8320
Coldwell Banker Realty, (203) 227-8424
Bought with: Kim Vartuli, (203) 258-3797, Keller Williams Realty, (203) 429-4020
Source: Smart MLS, MLS#24127092

Price History for 2281 Redding Road

DatePriceEventSource
02/09/2026$4,700,000Sold
Smart MLS #24127092
12/27/2025$4,995,000PendingSmart MLS #24127092
09/27/2025$4,995,000Listed For SaleSmart MLS #24127092
02/28/2014$2,100,000Sold
Smart MLS #98535917
04/19/2012$2,395,000Listed For SaleAgent Provided
11/05/2011$2,395,000ListingRemovedAgent Provided
03/12/2011$2,395,000PriceChange
Agent Provided
07/27/2010$2,950,000Listed For SaleAgent Provided

Market trends in Fairfield

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$987K
$49KMoM
Sale-to-List Price
103.3%
0.6%MoM
Price per sq ft
$483
$16MoM
Available listings
178
10MoM
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Property Tax and Assessment

Year2025
Tax$35,970
Assessment$1,267,000
Home facts updated by county records

Comparable Sales for 2281 Redding Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2787 Redding Road, Fairfield, CT
0.40
Single-Family Home
$2,000,000
08/18/25
4
4.5
4,060
158 Coventry Lane, Fairfield, CT
0.52
Single-Family Home
$2,225,000
03/17/26
4
3.5
4,255
85 Whiting Pond Road, Fairfield, CT
0.40
Single-Family Home
$998,000
07/21/25
4
2.5
4,406
125 Brett Lane, Fairfield, CT
0.63
Single-Family Home
$2,337,000
10/10/25
6
8
7,843
3853 Congress Street, Fairfield, CT
0.64
Single-Family Home
$1,170,000
01/15/26
4
5.5
4,906
215 Paddock Hill Lane, Fairfield, CT
0.66
Single-Family Home
$1,875,000
08/22/25
4
4.5
5,737
101 Brambley Hedge Circle, Fairfield, CT
0.77
Single-Family Home
$1,500,000
02/13/26
5
5
5,136
3810 Congress Street, Fairfield, CT
0.71
Single-Family Home
$1,753,000
05/18/26
4
2.5
4,051

Nearby homes

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Assigned Schools

These are the assigned schools for 2281 Redding Road.
View nearby schools on GreatSchools
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 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

  • 78 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 71 % Say kids play outside

  • 67 % 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

  • 49 % 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
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  • Bnsdkbr225
    "Friendly and beautiful. Close to Lake Mohegan and parks. Lake rights to Lake Hill’s association . "
    0
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  • Kevin.cohen318
    "Great place to raise a family, incredibly safe and has all the amenities you could want on a year round basis."
    0
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  • Alexande.pappas
    "Yes walking miking kids walking to school we have public beaches lake’s plenty of restaurants churches"
    0
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  • Samuel Rivera
    "Great town for families with kids. Fairfield offers great schools, good supermarkets, tons of restaurants and entertainment "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Raquel
    "Great family environment, lots of parks. Neighbors are friendly and welcoming. A lot of activities for kids. "
    0
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  • Lisalberts
    "It’s friendly and easy to walk or ride bikes around. The schools are wonderful. A real community feel."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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Homes for sale near 2281 Redding Road

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Off Market Homes Near 2281 Redding Road

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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.