1338 Brookside Dr, Fairfield, CT 06824
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Property image
OFF MARKET

1338 Brookside Dr
Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 5,167 sqft (on 2.76 acres)

$2,102,500

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $13,778/mo*
Refinance Your Home

$2,102,500

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $13,778/mo*
Refinance Your Home
4 Beds
3.5 Baths
5,167 sqft
(on 2.76 acres)

Home Value

Trulia Estimate
$2.1M
Since last month
Decreased$7K (-0.3%)
Since last year
Increased$199K (+10.3%)
Since last sale
Increased$519K (+32.4%)
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
August 2026$2.12M
July 2026$2.13M
June 2026$2.13M
May 2026$2.08M
April 2026$2.04M
March 2026$2.07M
February 2026$1.96M
January 2026$1.95M
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
1218 Brookside Dr, Fairfield, CT
0.13
Single-Family Home
$2,995,000
07/06/26
4
4
3,847
40 Hill Brook Lane, Fairfield, CT
0.15
Single-Family Home
$2,995,000
07/02/26
4
4
3,847
39 Campbell Road, Fairfield, CT
0.45
Single-Family Home
$1,600,000
08/27/25
5
3.5
4,033
254 Sherwood Farm Road, Fairfield, CT
0.57
Single-Family Home
$1,850,000
12/15/25
4
4.5
4,515
820 Hillside Road, Fairfield, CT
0.57
Single-Family Home
$2,215,000
06/10/26
3
2.5
3,594
218 Lower Farm Rd, Fairfield, CT
0.38
Single-Family Home
$2,150,000
04/01/26
4
4
3,438
218 Lower Farm Road, Fairfield, CT
0.46
Single-Family Home
$2,150,000
03/31/26
4
4
4,152
93 Millspaugh Drive, Fairfield, CT
0.34
Single-Family Home
$1,940,000
11/06/25
5
5
4,440
338 Orchard Hill Lane, Fairfield, CT
0.59
Single-Family Home
$1,750,000
01/13/26
4
2.5
3,867
175 Alma Drive, Fairfield, CT
0.41
Single-Family Home
$1,450,000
10/30/25
4
3
2,794

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
1321 Brookside Drive, Fairfield, CT 06824
0.11
$1,765,000
4
2
1,740
Off Market
40 Hill Brook Lane, Fairfield, CT 06824
0.15
$2,995,000
4
4
3,847
Recently Sold
118 Mill River Road, Fairfield, CT 06824
0.17
$1,463,300
4
2.5
1,944
Off Market
1100 Brookside Drive, Fairfield, CT 06824
0.22
$1,754,400
4
3
3,730
Off Market
100 Mine Hill Road, Fairfield, CT 06824
0.21
$3,489,600
4
3.5
6,279
Off Market
1569 Brookside Drive, Fairfield, CT 06824
0.22
$1,247,500
3
2.5
2,202
Off Market
79 Cynthia Drive, Fairfield, CT 06824
0.25
$1,076,800
3
2.5
2,093
Off Market
200 Mine Hill Road, Fairfield, CT 06824
0.24
$3,030,900
5
6
5,601
Off Market
51 Cynthia Drive, Fairfield, CT 06824
0.26
$954,300
3
2
2,856
Off Market
153 Dudley Drive, Fairfield, CT 06824
0.27
$1,369,000
4
2.5
2,897
Off Market
337 Hill Brook Lane, Fairfield, CT 06824
0.31
$2,153,900
4
5
5,086
Off Market
2465 Mill Plain Road, Fairfield, CT 06824
0.29
$974,000
3
1.5
1,906
Recently Sold

Local Information

  • Map ViewExplore the area around 1338 Brookside Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1984
Lot Size
2.76 acres
Living Area
5,167 sqft
Price/Sqft
$407
Parking
Garage

About this House

Sited behind stone pillars, on almost 3 acres of beauty in lower Greenfield Hill, you'll find a picturesque home that offers something on everyones wishlist w/ 5000+ sqft on 3 levels & a floor plan designed for everyday living & entertaining. The foyer is flanked by the home office & formal living room warmed by a fireplace. Hardwoods guide you into the dining rooma traditional space that opens to the EIK. The kitchen offers a desk area, tons of cabinets, pantry, & access to the deck - ideal for dining al fresco. The family room will WOW you w/ soaring ceilings, walls of windows, fireplace & a full wet bar, creating perfection for cozy nights relaxing by the fire & parties. Interior French doors lead you into the four seasons room. Finishing the 1st floor is the laundry, full bath w/ shower, & powder room. Upstairs has four nicely sized bedrms & two full baths, incl. the primary suite. A true retreat w/ a cathedral ceiling, his /her closets, walk-in closet, bath, & a private balcony overlooking the lush grounds & pool. The bathroom is stunning w/ a large shower & marble double vanity. The lower level has a den, game room w/ bar, wine cellar & mudroom. There is truly a space for everyone. Outside provides an every day vacation w/ an in-ground pool & a patio & deck. You'll love BBQs or quiet days outside soaking in your own oasis. A perfect combination of convenience & country yet minutes to downtown, train, beaches, eateries, & more! Once home, you'll never want to leave.
1338 Brookside Dr, Fairfield, CT 06824 is a 4 bedroom, 4 bathroom, 5,167 sqft single-family home built in 1984. It last sold for $1,600,000 on Aug 23, 2022. It is currently off market. The Trulia Estimate is $2,102,500, with a rent estimate of $7,897/month.

Home Details for 1338 Brookside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.76 acres

Price and Tax history

DateEventPrice
Aug 23, 2022
Source: Smart MLS #170474365
Sold
$1,600,000
May 12, 2022
Source: Smart MLS #170474365
Contingent
$1,499,000
Apr 7, 2022
Source: William Raveis Real Estate, Mortgage & Insurance #170474365
Pending
$1,499,000
Apr 1, 2022
Source: Smart MLS #170474365
Listed For Sale
$1,499,000
Jul 30, 2015
Source: Smart MLS #99097029
Sold
$1,087,500

Market trends in Fairfield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$957K
$29.79KMoM
Sale-to-List Price
103.7%
0.4%MoM
Price per sq ft
$477
$5MoM
Available listings
162
16MoM

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
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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
    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

LGBTQ Local Legal Protections

Frequently asked questions about 1338 Brookside Dr

  • What is 1338 Brookside Dr estimated to be worth?
    Trulia's estimated value for 1338 Brookside Dr in Fairfield, CT is $2,102,500.
  • What is the price history for 1338 Brookside Dr?
    1338 Brookside Dr in Fairfield, CT last sold for $1,600,000 in August 2022.
  • Is Fairfield a buyer's or seller's market?
    Fairfield is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Fairfield?
    The median sale price in Fairfield is $957K. That is down $29.79K from the prior month.
  • Does 1338 Brookside Dr have air conditioning?
    Yes, 1338 Brookside Dr in Fairfield, CT has air conditioning.
  • Does 1338 Brookside Dr have a pool?
    Yes, 1338 Brookside Dr in Fairfield, CT has a pool.

Explore by feature - Pet Friendly

24 pet-friendly rentals in Fairfield, CT

Explore by feature - Garage

42 rentals with a garage in Fairfield, CT

Explore by feature - Air Conditioning

88 rentals with air conditioning in Fairfield, CT

Explore by feature - Pool

11 rentals with a pool in Fairfield, CT

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112 rentals with a washer/dryer in Fairfield, CT

Explore by feature - Outdoor Space

26 rentals with an outdoor space in Fairfield, CT

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Off Market Homes Near 1338 Brookside Dr

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