65 Trailside Drive
Monroe, Connecticut 06468
Reduced from $1,199,900
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 5,304
- Acres
- 2.00
- Year Built
- 2003
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Located on a desirable cul de sac in one of Monroe's most sought after neighborhoods, this exceptional Colonial is set on two beautifully usable acres and offers an impressive blend of scale, sophistication, and versatility. Thoughtfully designed for today's lifestyle, the residence features five spacious bedrooms and four full and one half baths, delivering both comfort and refined living in a premier setting. A full main level in law apartment provides private, self contained living ideal for multigenerational households, extended guests, or long term flexibility without compromise. The main level is enhanced by gleaming hardwood flooring throughout and offers a seamless flow between formal and informal spaces, creating an inviting environment for both everyday living and elegant entertaining. Upstairs, the primary suite serves as a true retreat. The brand new primary bath has been beautifully renovated with elevated finishes and a sophisticated, spa inspired design. Three additional bedrooms, including one with en suite bath, complete the upper level with style and functionality. The finished lower level is designed for entertainment, featuring a dedicated movie room and an impressive bar area perfect for hosting gatherings or enjoying relaxed evenings at home. A three car garage offers generous storage and convenience, while a large deck overlooks the expansive, level backyard, providing privacy and endless possibilities for outdoor living. Schedule your showing today!
Key Facts
- City/Town
- Monroe
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2003
- Days on Market
- 146 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 5,304 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $19,584 / Annually
Market Snapshot
The Monroe Market
Single Family · trailing 12 months
Active Listings
44
35 under contract
Median List Price
$757,000
44 active listings
Median Closed Price
$685,000
180 sales
Median Days on Market
41
44 active listings
Median $ / Sq Ft
$259
44 active listings
Sale-to-List Ratio
100.0%
180 sales
How this home compares
List Price
$1.17M
vs $757,000 median
55.2% above median
Price / Sq Ft
$222
vs $259 median
14.3% below median
Days on Market
146 days
vs 41 days median
105 days longer than median
Based on 44 active and 180 closed sales (trailing 12 mo) of single family in Monroe. Source: SmartMLS · As of July 28, 2026.
Location
65 Trailside Drive, Monroe, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,990
- Property Taxes$1,632
- Insurance$392
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Monroe
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2003
- New Construction
- No/Resale
- Living Area
- 5,304 sq ft
- Below Grade
- 1,374 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Masuk
Interior
- Heating
- Hydro Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullFully Finished
- In-Law Apartment
- YesFirst Floor
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- RF2
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level LotOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $19,584 / Annually
- Days on Market
- 146
- MLS #
- 24156537
- MLS Status
- Active
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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 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.