385 Brookside Drive
Fairfield, CT 06824
4 Beds
2.5 Baths
3,040 sqft (on 1.14 acres)
$1,500,000
Last Sold: Aug 15, 2025
7% over list $1.4M
$493/sqft
Est. Refi. Payment $9,740/mo*
$1,500,000
Last Sold: Aug 15, 2025
7% over list $1.4M
$493/sqft
Est. Refi. Payment $9,740/mo*
4 Beds
2.5 Baths
3,040 sqft
(on 1.14 acres)
Local Information
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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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from August 15, 2025
Home Highlights
Parking
2 Car Garage
Outdoor
Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$493/sqft
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: $1,399,000Price Per Sqft: $493/sqft |
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 6 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
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 |
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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 | |
0.69 | Single-Family Home | $1,600,000 | 06/30/25 | 5 | 2.5 | 3,504 |
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Assigned Schools
These are the assigned schools for 385 Brookside Drive.
- Fairfield Woods Middle School
- 6-8
- Public
- 743 Students
8/10GreatSchools RatingParent Rating AverageI LOVE THE PASSION IN THIS SCHOOL. All the teachers and principals are welcoming and they put there hard work in to us and care about what we doOther Review15y ago - Osborn Hill School
- K-5
- Public
- 441 Students
9/10GreatSchools RatingParent Rating AverageBoth of my boys attend OHS and it’s an amazing school! Wonderful teachers and staff and Mr. Hudspeth is wonderful! He is clearly dedicated to staff and students and leads by example each day. On numerous occasions he has gone out of his way to help our family, as well as many others I know. OHS is the best of the best and we are fortunate to to live around the corner. It’s the main reason we chose our home so that we could walk each dayParent Review5y ago - Fairfield Ludlowe High School
- 9-12
- Public
- 1498 Students
9/10GreatSchools RatingParent Rating AverageThey never taught me on how to find a college for students who have autism or a disability. 3. They never taught me on how every college has different academics, Services, sports, clubs, and activities. The auditorium is way too small. You can’t fit everyone in there. Parking was just hell. There wasn’t enough spots for all students and as well they just let people who live close enough to walk drive to school and then people who don’t live close enough to walk won’t get a spot. There’s no baseball field on campus. More facilities on campus will decrease global warming as they don’t have to hire bus transportation and staying on campus burns less fossil fuels. Football season and all other fall sports start too early in the summer time and because of that sometimes people aren’t able to play since they’ll be away. No breakfast is sold at period 2 at all. Sometimes people don’t eat breakfast at all since high school starts at 7:30 pm. Don’t have enough food selections at lunchtime. Senior lounge has doesn’t have enough seats for people to sit next to friends and because of that a lot of the times I sat isolated on the benches in the senior lounge. It doesn’t feel like a new school year, it’s hard to separate others if they’re being too nonsense, not getting along with one another, causing too much trouble, and sometimes one homeroom can become more crowded than another if one student transfers to a different school or if one student transfers to FLHS because you’re locked in the same homeroom all four years of high school.Other Review5y ago 
Check out schools near 385 Brookside Drive.
What Locals Say about Fairfield
At least 342 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
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
58 % Say streets are well-lit
56 % Say it's walkable to restaurants
49 % Say there are community events
47 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Homes for rent near 385 Brookside Drive
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385 Brookside Drive, Fairfield, CT 06824 is a 4 bedroom, 3 bathroom, 3,040 sqft single-family home built in 1784. This property is not currently available for sale. 385 Brookside Drive was last sold on Aug 15, 2025 for $1,500,000 (7% higher than the asking price of $1,399,000). The current Trulia Estimate for 385 Brookside Drive is $1,563,500.