385 Brookside Drive, Fairfield, CT 06824
OFF MARKET

385 Brookside Drive
Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 3,040 sqft (on 1.14 acres)

$1,595,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $10,483/mo*
Refinance Your Home

$1,595,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $10,483/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,040 sqft
(on 1.14 acres)

Home Value

Trulia Estimate
$1.6M
Since last month
Decreased$3K (-0.2%)
Since last year
Increased$90K (+6%)
Since last sale
Increased$92K (+6.2%)
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 +162% in the last 10 years
MonthEstimated value
2026
August 2026$1.59M
July 2026$1.6M
June 2026$1.59M
May 2026$1.57M
April 2026$1.55M
March 2026$1.54M
February 2026$1.54M
January 2026$1.52M
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
47 Trillium Circle, Fairfield, CT
0.20
Single-Family Home
$1,200,000
08/27/25
4
3.5
3,266
1185 Stillson Road, Fairfield, CT
0.47
Single-Family Home
$1,360,000
08/17/26
3
2.5
2,788
242 Valleyview Road, Fairfield, CT
0.17
Single-Family Home
$1,830,000
11/07/25
4
3.5
3,200
845 Mountain Laurel Road, Fairfield, CT
0.32
Single-Family Home
$1,180,000
02/12/26
4
2.5
2,068
274 Valleyview Road, Fairfield, CT
0.20
Single-Family Home
$1,350,000
07/16/26
3
2.5
2,562
1165 Stillson Road, Fairfield, CT
0.43
Single-Family Home
$1,325,000
01/08/26
4
2.5
2,704
692 Stillson Road, Fairfield, CT
0.33
Single-Family Home
$1,599,000
07/13/26
4
2.5
2,962
385 Samp Mortar Drive, Fairfield, CT
0.11
Single-Family Home
$834,000
05/15/26
4
2
2,045
34 Ridgedale Road, Fairfield, CT
0.19
Single-Family Home
$1,699,000
11/14/25
4
4.5
3,200

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
321 Brookside Drive, Fairfield, CT 06824
0.05
$1,677,800
4
3.5
3,468
Off Market
273 Pansy Road, Fairfield, CT 06430
0.12
$1,034,300
3
2.5
1,950
Off Market
2470 North Benson Road, Fairfield, CT 06824
0.11
$1,999,600
5
4.5
4,032
Off Market
42 Valley View Road, Fairfield, CT 06824
0.13
$943,600
3
2
1,523
Off Market
516 Brookside Drive, Fairfield, CT 06430
0.09
$1,390,500
4
2.5
3,200
Off Market
385 Samp Mortar Drive, Fairfield, CT 06824
0.11
$834,000
4
2
2,045
Recently Sold
11 Abbey Road, Fairfield, CT 06824
0.12
$1,516,900
3
2.5
2,933
Off Market
242 Valleyview Road, Fairfield, CT 06824
0.17
$1,830,000
4
3.5
3,200
Recently Sold
210 Pansy Road, Fairfield, CT 06824
0.18
$1,910,000
5
3.5
3,780
Recently Sold
260 Pansy Road, Fairfield, CT 06824
0.18
$1,899,900
5
3.5
3,730
Recently Sold
54 Ridgedale Road, Fairfield, CT 06824
0.17
$775,000
3
1
1,202
Recently Sold

Local Information

  • Map ViewExplore the area around 385 Brookside Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1784
Lot Size
1.14 acres
Living Area
3,040 sqft
Price/Sqft
$525
Parking
2 Car Garage

About this House

Magnificent University Circa 1784 colonial farmhouse w updates & renovations galore filled to the brim with charm & character! Original details impeccably preserved, modern updates abound. Gorgeous EIK w over-sized island, gas stove, newer appliances, apron sink, wet bar, butler's pantry & large eating area opens to family room w show-stopping original fireplace, beams & stunning mill work. Spacious living w beams, built-ins & original fireplace. Large sundrenched dining room w built-ins, paneling & fireplace. Home office w custom built-ins, separate entrance. 1st floor Laundry w custom cabinetry. Vast luxury primary suite w large sitting area & marble spa-like bath inclusive of glass stall shower, soaking tub, dual vanity & radiant floors, huge WIC, cedar closet. 3 add'l BRs up all w different personalities share hall bath. 5th BR on 1st floor w exposed brick fireplace. Expansive 576 sq ft bonus room w full bath & separate french door entrance offers endless options for 2nd family room, 1st floor primary, au pair suite. Private 1+ acre oasis w large deck, outdoor shower, magnificent in-ground pool, oversized stone patio & custom outdoor fireplace ideal for entertaining. Charming front porch w swing. Original & reclaimed hardwood floors everywhere. Beams, mill work, paneling, trim & detail exquisite! Newer mechanicals, electric & 4 zoned systems. Propane heat/top of line HVAC. Walk to Osborn, close to Merritt & 95. A very special unique property. Welcome Home! All plumbing in house was replaced in 2012 as were all vents as home was fitted for 4 zone systems. 5 fireplaces in the home, 2 are working, the other 3 are aesthetically charming but remain non-functioning. The finished bonus rooms brings total sq footage to 3616. Hatch in floor of bonus room opens to staircase for interior garage access. Property edge has picture-perfect babbling brook on other side of fence. Office & bonus room both have separate entrances. University/Lower Greenfield Hill
385 Brookside Drive, Fairfield, CT 06824 is a 4 bedroom, 3 bathroom, 3,040 sqft single-family home built in 1784. It last sold for $1,500,000 on Aug 15, 2025 (7% above the $1,399,000 asking price). It is currently off market. The Trulia Estimate is $1,595,700, with a rent estimate of $6,461/month.
Last check for updates: about 8 hours ago
Listed by Lara Hoey, (203) 814-7427
William Raveis Real Estate, (203) 255-6841
Bought with: Alex Kniffin, (203) 295-4338, Century 21 AllPoints Realty, (203) 327-0021
Source: Smart MLS, MLS#24090062

Home Details for 385 Brookside Drive

Interior Features

Interior Details
Basement: Partial,Unfinished,Sump Pump,Interior Entry,ConcreteNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room, Office, Other, Rec Play Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3040 Square Feet
Appliances & Utilities
Appliances: Gas Cooktop, Gas Range, Oven/Range, Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main Level,Mud RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Radiant,Zoned,PropaneHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 5Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PatioFencing: Partial, PrivacyExterior: Rain Gutters, Garden, LightingFoundation: Concrete Perimeter, StoneGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Pool
Pool: Concrete, In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3040 Square Feet

Property Information

Year Built
Year Built: 1784
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Antique
Building
Construction Materials: Clapboard, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 125366

Price & Status

Price
List Price: $1,399,000
Status Change & Dates
Off Market Date: Thu Jun 12 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: FairfieldCommunity: Greenfield Hill
School Information
Elementary School: Osborn HillJr High / Middle School: Fairfield WoodsHigh School: Fairfield Ludlowe

Building

Building Area
Building Area: 3040 Square Feet

Community

Community Features: Golf, Lake, Library, Medical Facilities, Paddle Tennis, Park, Playground, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 1.14 Acres

Miscellaneous

BasementMls Number: 24090062Attic: Storage, Pull Down StairsAbove Grade Unfinished Area: 3040

Additional Information

GolfLakeLibraryMedical FacilitiesPaddle TennisParkPlaygroundShopping/Mall

Price and Tax history

DateEventPrice
Aug 15, 2025
Source: Smart MLS #24090062
Sold
$1,500,000
Jun 12, 2025
Source: William Raveis Real Estate, Mortgage & Insurance #24090062
PendingToActive
$1,399,000
May 10, 2025
Source: William Raveis Real Estate, Mortgage & Insurance #24090062
Pending
$1,399,000
May 1, 2025
Source: Smart MLS #24090062
Listed For Sale
$1,399,000
Nov 30, 2017
Source: Agent Provided
ListingRemoved
$850,000

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
    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

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Frequently asked questions about 385 Brookside Drive

  • What is 385 Brookside Drive estimated to be worth?
    Trulia's estimated value for 385 Brookside Drive in Fairfield, CT is $1,595,700.
  • What is the price history for 385 Brookside Drive?
    385 Brookside Drive in Fairfield, CT last sold for $1,500,000 in August 2025.
  • 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 385 Brookside Drive have air conditioning?
    Yes, 385 Brookside Drive in Fairfield, CT has air conditioning.
  • Does 385 Brookside Drive have a pool?
    Yes, 385 Brookside Drive in Fairfield, CT has a pool.

Explore by feature - Pet Friendly

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