385 Brookside Drive
Fairfield, CT 06824
- 4 Beds
- 2.5 Baths
- 3,040 sqft (on 1.14 acres)
4 Beds
2.5 Baths
3,040 sqft
(on 1.14 acres)
Local Information
-- mins to
Description
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 $1,588,700, with a rent estimate of $6,741/month.
Home Highlights
Parking
2 Car Garage
Outdoor
Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 385 Brookside Drive
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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 |
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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 |
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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 |
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Price List Price: $1,399,000 |
Status Change & Dates Off Market Date: Thu Jun 12 2025Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: FairfieldCommunity: Greenfield Hill |
School Information Elementary School: Osborn HillJr High / Middle School: Fairfield WoodsHigh School: Fairfield Ludlowe |
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Building Area Building Area: 3040 Square Feet |
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Community Features: Golf, Lake, Library, Medical Facilities, Paddle Tennis, Park, Playground, Shopping/Mall |
Other Playground |
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No HOA |
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Lot Area: 1.14 Acres |
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BasementMls Number: 24090062Attic: Storage, Pull Down StairsAbove Grade Unfinished Area: 3040 |
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GolfLakeLibraryMedical FacilitiesPaddle TennisParkPlaygroundShopping/Mall |
Last check for updates: about 1 hour 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

Price History for 385 Brookside Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 08/15/2025 | $1,500,000 | Sold | Smart MLS #24090062 |
| 06/12/2025 | $1,399,000 | PendingToActive | William Raveis Real Estate, Mortgage & Insurance #24090062 |
| 05/10/2025 | $1,399,000 | Pending | William Raveis Real Estate, Mortgage & Insurance #24090062 |
| 05/01/2025 | $1,399,000 | Listed For Sale | Smart MLS #24090062 |
| 11/30/2017 | $850,000 | ListingRemoved | Agent Provided |
| 09/27/2017 | $850,000 | Listed For Sale | Agent Provided |
| 11/14/2012 | $490,000 | Sold | Smart MLS #98541338 |
| 07/25/2012 | $450,000 | ListingRemoved | Agent Provided |
| 06/02/2012 | $450,000 | Listed For Sale | Agent Provided |
| 08/16/1995 | $239,000 | Sold | Smart MLS #95018355 |
Market trends in Fairfield
Last updated May 2026
Avg. sale price
$921K
$34.17KMoM
Sale-to-List Price
102.7%
0.5%MoM
Price per sq ft
$498
$23MoM
Available listings
168
38MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $14,257 |
| Assessment | $502,180 |
Home facts updated by county records
Comparable Sales for 385 Brookside Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.20 | Single-Family Home | $1,200,000 | 08/27/25 | 4 | 3.5 | 3,266 | |
0.22 | Single-Family Home | $1,280,000 | 08/11/25 | 4 | 2.5 | 3,050 | |
0.18 | Single-Family Home | $1,705,000 | 08/05/25 | 4 | 3 | 4,176 | |
0.17 | Single-Family Home | $1,830,000 | 11/07/25 | 4 | 3.5 | 3,200 | |
0.32 | Single-Family Home | $1,180,000 | 02/12/26 | 4 | 2.5 | 2,068 | |
0.43 | Single-Family Home | $1,325,000 | 01/08/26 | 4 | 2.5 | 2,704 | |
0.11 | Single-Family Home | $834,000 | 05/15/26 | 4 | 2 | 2,045 | |
0.19 | Single-Family Home | $1,699,000 | 11/14/25 | 4 | 4.5 | 3,200 | |
0.42 | Single-Family Home | $1,415,000 | 12/10/25 | 3 | 3.5 | 2,849 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 385 Brookside Drive.
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.
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