385 Brookside Dr

Fairfield, CT 06824

$1,500,000
Last Sold Price
4
Beds
3,040 Sq. Ft.
$493 / Sq. Ft.
3,040
Sq. Ft.
$493
per Sq. Ft.
Closed 8/15/25
Closed 8/15/25

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...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!
  1. Listed by Lara Hoey • William Raveis Real Estate
    P: (203)-814-7427 C: (203)-814-7427 laraphoey@gmail.com

Property Details for 385 Brookside Drive

Basement Description
Partial, Unfinished, Sump Pump, Interior Access, Concrete Floor, Partial With Walk-Out
Direct Waterfront
No
Expected Active Date
05-01-2025
Garages Number
2
Neighborhood
Greenfield Hill
Style
Colonial, Antique
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 08/15/2025 08:32 PM

Property Details for 385 Brookside Drive

StatusClosed
MLS #24090062
Days on Market9
Taxes$14,257 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1784
Lot Size1.14 AC / 49,658 SF
CountyFairfield County

Location

Listing Courtesy of William Raveis Real Estate, Lara Hoey

Sold By Century 21 AllPoints Realty, Alex Kniffin

Add your commute

Building Information for 385 Brookside Drive

Stories-Year Built1784Building Size-Lot Size1.14 AC / 49,658 SF

Payment Calculator

$8,499 per month

30 year fixed, 6.15% Interest

Principal and Interest

$7,311

Property Taxes

$1,188

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 385 Brookside Drive

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: North Benson or Pansy to Brookside Drive, home on private road adjacent to (and considered) Brookside Drive.
  • Elementary School: Osborn Hill
  • Flood Zone: No
  • High School: Fairfield Ludlowe
  • Latitude: 41.180301
  • Longitude: -73.260462
  • Middle Jr High School: Fairfield Woods
  • Neighborhood Amenities: Golf Course, Lake, Library, Medical Facilities, Paddle Tennis, Park, Playground/Tot Lot, Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $14,257
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Gutters, Garden Area, Lighting, French Doors, Patio
  • Pool Description: Concrete, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Cooktop, Gas Range, Oven/Range, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air, Radiant, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 5
  • Interior Features: Audio System, Open Floor Plan
  • Laundry Room Info: Main Level
  • Laundry Room Location: First Floor
  • Rooms Additional: Bonus Room, Laundry Room, Mud Room
  • Rooms Total: 11
Room 1
  • Room Entry Order: 1
  • Room Features: Beams,Built-Ins,Fireplace,French Doors,Hardwood Floor,Wide Board Floor
  • Room Length: 27.8
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.1
Room 2
  • Room Entry Order: 10
  • Room Features: Skylight,Double-Sink,Hydro-Tub,Stall Shower,Marble Floor
  • Room Length: 15.6
  • Room Level: Upper
  • Room Type: Primary Bath
  • Room Width: 9.1
Room 3
  • Room Entry Order: 11
  • Room Features: Beams,Walk-In Closet,Hardwood Floor,Wide Board Floor
  • Room Length: 14.1
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.7
Room 4
  • Room Entry Order: 12
  • Room Features: Beams,Book Shelves,Fireplace,Hardwood Floor
  • Room Length: 16.7
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.1
Room 5
  • Listing Key: 3361ED3B9C923F09E063D501100A90A9
  • Room Entry Order: 13
  • Room Features: Beams,Wall/Wall Carpet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Other
Room 6
  • Room Entry Order: 14
  • Room Features: Skylight,Vaulted Ceiling,Built-Ins,Double-Sink,Tub w/Shower,Tile Floor
  • Room Length: 9.1
  • Room Level: Upper
  • Room Type: Full Bath
  • Room Width: 8.1
Room 7
  • Room Entry Order: 15
  • Room Features: Fireplace,Wall/Wall Carpet,Hardwood Floor
  • Room Length: 12.6
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 8.1
Room 8
  • Room Entry Order: 2
  • Room Features: Beams,Built-Ins,Fireplace,Hardwood Floor
  • Room Length: 15.5
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 14.2
Room 9
  • Listing Key: 3361ED3B9C923F09E063D501100A90A9
  • Room Entry Order: 3
  • Room Features: Beams,Dining Area,Wet Bar,Island,Pantry,Tile Floor
  • Room Length: 24.1
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 15.7
Room 10
  • Room Entry Order: 4
  • Room Features: Beams,Built-Ins,Fireplace,Hardwood Floor,Wide Board Floor
  • Room Length: 14.5
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 13.9
Room 11
  • Room Entry Order: 5
  • Room Features: Granite Counters,Tile Floor
  • Room Length: 5.6
  • Room Level: Main
  • Room Type: Half Bath
  • Room Width: 4.7
Room 12
  • Room Entry Order: 6
  • Room Features: Book Shelves,Built-Ins,Entertainment Center,Hardwood Floor,Wide Board Floor
  • Room Length: 14.5
  • Room Level: Main
  • Room Type: Office
  • Room Width: 11.1
Room 13
  • Room Entry Order: 7
  • Room Features: Full Bath,Composite Floor
  • Room Length: 23.11
  • Room Level: Main
  • Room Type: Rec/Play Room
  • Room Width: 22.11
Room 14
  • Room Entry Order: 8
  • Room Features: Quartz Counters,Tub w/Shower,Tile Floor
  • Room Level: Main
  • Room Type: Full Bath
Room 15
  • Room Entry Order: 9
  • Room Features: Vaulted Ceiling,Beams,Built-Ins,Full Bath,Walk-In Closet,Wide Board Floor
  • Room Length: 30.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 21.0
Property
Property and Assessments
  • Color: Gray
  • Construction Description: Frame
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Concrete, Stone
  • Fuel Tank Location: Above Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1784
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor, Separate Entry
  • In Law Apartment: Possible
  • Sq Ft Est Heated Below Grade: 0
  • Living Area SQFT Per Public Records: 3040
Lot Information
  • Lot Description: Fence - Partial, Fence - Privacy, Some Wetlands, Treed, Level Lot, Rolling
  • Parcel Number: 125366
  • Sq Ft Est Heated Above Grade: 3040.0
  • Sq Ft Total: 3040.0
  • Zoning: A
Utilities
  • Heat Fuel Type: Propane
  • Hot Water Description: Other
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 385 Brookside Drive

DateEvent & SourcePriceAppreciation
Aug 15, 2025

Closed (Public Record)

Public Record #1911643049

$1,500,000

+9.2% / yr

Nov 21, 2012

Closed (Public Record)

Public Record #342275574

$490,000

+965.0% / yr

May 9, 2007

Closed (Public Record)

Public Record #327036904

$1

-65.2% / yr

Aug 16, 1995

Closed (Public Record)

Public Record #90966306

$239,000—
DateEvent & SourcePrice
08/15/2025

Closed (Public Record)

Public Record #1911643049

$1,500,000

+9.2% / yr

11/21/2012

Closed (Public Record)

Public Record #342275574

$490,000

+965.0% / yr

05/09/2007

Closed (Public Record)

Public Record #327036904

$1

-65.2% / yr

08/16/1995

Closed (Public Record)

Public Record #90966306

$239,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 385 Brookside Drive

Taxable ValueLand$304,290Additions$197,890Total$502,180
Tax Record2024$14,257 ($1,188 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt3,040 SqFtAbove Grade Finished SqFt3,040 SqFtUnfinished Basement SqFt784 SqFtStories2Lot Size49,658 SqFtStyleSingle Family ResidenceYear Built1784ZoningACountyFAIRFIELDAPNFFLD M:123 B:167

Schools near 385 Brookside Drive

This home is within Fairfield School District.
Rating
School
Type
Grades
Distance
Osborn Hill School
Public - K to 5
Fairfield Woods Middle School
Public - 6 to 8
Fairfield Ludlowe High School
Public - 9 to 12
Rating
School
Distance
Osborn Hill School
PublicK to 5

Fairfield Woods Middle School
Public6 to 8

Fairfield Ludlowe High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of William Raveis Real Estate, Lara Hoey

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.