366 Brookside Drive
Fairfield, Connecticut 06824
- Beds
- 3
- Baths
- 2
- SqFt
- 2,135
- Acres
- 0.29
- Year Built
- 1952
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to this beautifully updated home in the desirable Lake Hills Association, where comfortable living comes with lake and beach access. Larger than the typical Cape, this 3 bed, 2 bath home offers a bright, open floor plan with hardwood floors, generous living spaces, and an easy flow for everyday life and entertaining. At the heart of the home is the updated kitchen, featuring white cabinetry, quartz countertops, stainless steel appliances, a tile backsplash, and an oversized island with seating. The kitchen opens to the living and dining areas, creating a spacious gathering space filled with natural light and highlighted by a charming fireplace. Just off the main living area, the screened three-season porch with removable windows offers a peaceful place to relax and enjoy the surrounding greenery. Recent updates include crown molding, hardwood flooring, walk-in showers, and a refreshed lower level. The partially finished basement offers flexible space for a family room, office, gym, or recreation area, while the unfinished portion and oversized attic provide excellent storage. Major improvements include a new furnace, new oil tank, and new blown-in insulation. With its welcoming curb appeal, updated interior, flexible living space, and lake and beach access, this home is ready to enjoy year round.
Key Facts
- City/Town
- Fairfield
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1952
- Days on Market
- 1 day
- Beds
- 3
- Baths
- 2 full
- Living Area
- 2,135 sq ft
- Lot Size
- 0.29 acres
- Garage / Parking
- 4 total
- Property Taxes
- $9,962 / Annually
- HOA Fee
- $550 / Annually
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
94
65 under contract
Median List Price
$1.40M
94 active listings
Median Closed Price
$1.15M
587 sales
Median Days on Market
47
94 active listings
Median $ / Sq Ft
$484
94 active listings
Sale-to-List Ratio
102.3%
587 sales
How this home compares
List Price
$799,000
vs $1.40M median
42.8% below median
Price / Sq Ft
$374
vs $484 median
22.7% below median
Days on Market
1 day
vs 47 days median
46 days fresher than median
Based on 94 active and 587 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of September 16, 2026.
Location
366 Brookside Drive, Fairfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$4,150
- Property Taxes$830
- Insurance$266
- HOA$46
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Fairfield
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1952
- New Construction
- No/Resale
- Living Area
- 2,135 sq ft
- Below Grade
- 500 sq ft
Schools
- Elementary
- Osborn Hill
- High
- Fairfield Ludlowe
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Wall UnitWindow Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullStorageInterior AccessPartially Finished
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 0.29 acres
- Zoning
- A
- Garage / Parking
- 4 total parking spacesDrivewayPaved
- Waterfront Details
- Walk to WaterBeach RightsWater Community
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Wood
- Roof
- Shingle
- Foundation
- Concrete
- Exterior Features
- PorchGuttersPatio
- Lot Description
- Level Lot
HOA / Association
- Fee
- $550 / Annually
Listing & Financials
- Property Taxes
- $9,962 / Annually
- Days on Market
- 1
- MLS #
- 24207176
- MLS Status
- Coming Soon
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/16/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/16/2026 at 5:10 AM UTC.